Category: General
Oct 14, 2025
Stop Wasting Time in Meetings: The Framework I Wish I'd Had at That Disastrous Offsite
The Offsite That Went Nowhere
It was our annual strategic planning offsite, which, by title alone, implied gravitas. The kind of event where you book a nice hotel, order a buffet lunch that costs more than most people's weekly grocery bill, and convince yourself that being offsite somehow makes the thinking more strategic.
It didn't.
There were no clear objectives. No defined outcomes. Just the words "Annual Strategic Planning" sitting on the agenda like a promise of direction that never arrived, a placeholder for importance we hadn't actually earned.
We gathered in a conference room with a view, laptops open, caffeine flowing, notebooks pristine and ready to capture insights. We were going to "shape the future." The CEO kicked things off with enthusiasm and a confident smile: "Alright, let's talk about next year's strategy."
It didn’t take long before someone said it, the four words that derail more meetings than any others:
"I have an idea."
The idea wasn't bad. Actually, it was pretty good. It involved a partnership with a company that was gaining traction in our space, and it sounded plausible enough that nobody wanted to be the person to shoot it down immediately. Slides came out. Someone pulled up their financial model. Side conversations started about who would own the relationship. And suddenly we were knee-deep in pricing debates, hypothetical org charts, and "what if" scenarios about market positioning.
For twenty minutes, the room hummed with energy. People were engaged. We were doing strategy.
But here's what we weren't doing: answering any coherent question.
The idea stood alone, a shiny object that had hijacked the agenda. It wasn't connected to any declared objective. We hadn't defined what success looked like for the year, or for the meeting, or even for that conversation. We hadn't established whether we were trying to grow revenue, expand market share, enter new segments, or fix operational problems. We were just... talking about an idea because it seemed interesting.
After watching this unfold for long enough that the buffet lunch was getting cold, I finally asked the question that stopped the momentum like a record scratch:
"What's the objective of this meeting? What are we actually trying to achieve?"
Silence.
Then the nervous laughter that says, we probably should've figured that out beforehand.
The CEO looked at the agenda. Someone else looked at their laptop. A few people looked at me like I'd just asked why we breathe oxygen, something so obvious it shouldn't need to be said, yet nobody had an answer.
"Well," someone finally offered, "we're here to plan strategy for next year."
"Right," I said. "But what does that mean? Are we trying to decide between growth options? Identify our biggest risk? Commit to specific initiatives? All of the above? Something else?"
More silence. And that's when it hit me with uncomfortable clarity:
Most so-called strategy sessions fail not because people lack ideas, but because they lack objective-based constraints.
Everyone's rowing hard, but nobody's steering. We had smart people, good intentions, decent ideas, and a beautiful view. What we didn't have was structure.
An objective gives you a path to measure success. It lets you ask, at the end of the meeting, did we achieve what we set out to achieve, or did we just talk about interesting things?
A constraint defines where to focus, the edges of what matters, so the discussion stays useful instead of sprawling into every direction at once.
If our objective had been clear, "Identify two growth levers for next year and assign owners" and our constraint explicit, "Focus on expanding market share in our current market before considering new markets," we'd have known immediately what belonged in the discussion and what didn't.
That partnership idea? Maybe it fit. Maybe it didn't. But we couldn't evaluate it because we had no criteria for evaluation.
Instead, we left the offsite at 4 PM with pages of notes, scattered action items nobody would remember in a week, and no real decisions. It felt like progress because we'd been talking for six hours. It wasn't progress. It was just an expensive way to avoid making hard choices.
I drove home frustrated, and over the next few weeks, that frustration crystallized into something more useful: a framework.
Now, before any meeting begins, especially the important ones, I start with two questions:
What is the objective?
What are the constraints?
Because without those, even the best ideas are just noise. And even the most expensive offsite is just a scenic way to waste time.
Let me show you how this works.
The Hidden Problem: Everyone's Optimizing for Their Own Scoreboard
Before I dive into the framework, I need to address something that took me years to fully understand: why smart, well-intentioned people in the same company can spend hours in a room and make no progress.
It's not just that meetings lack structure. It's that every person at the table is optimizing for a different outcome, often without realizing it.
Think about who shows up to a strategic planning meeting:
Sales wants lower pricing, more features, more products, faster delivery, and whatever else will help them close deals this quarter.
Product wants time to build things right, fewer feature requests, and the freedom to focus on technical debt and user experience.
Finance wants predictable revenue, better margins, and cost control.
Marketing wants budget, creative freedom, and lead generation targets that are actually achievable.
The C-suite wants growth, profitability, market position, and something impressive to tell the board.
Here's the thing: none of these perspectives are wrong. In fact, having different viewpoints at a meeting is often valuable, it's how you spot blind spots, challenge assumptions, and avoid groupthink.
But it's also a massive source of unproductive conflict.
At that offsite I described, when we started discussing the partnership idea, here's what was actually happening under the surface:
The VP of Sales loved it because it would give them a new product to sell and access to the partner's customer base.
The CFO was skeptical because partnerships are notoriously hard to forecast and don't always generate the revenue you think they will.
The Head of Product was worried it would distract from the roadmap and create technical dependencies.
The CEO liked the optics of announcing a high-profile partnership but wasn't sure if it was the highest leverage move.
So we spent a long time debating, but we weren't really debating the same question. Sales was debating "will this help me hit quota?" Finance was debating "will this be profitable?" Product was debating "will this derail our existing plans?" And the CEO was debating "is this the best use of our limited resources?"
Without a clear objective, every person was scoring the idea against their own department's goals, not the company's goals.
This is why meetings spiral. This is why the same arguments happen over and over. This is why you leave feeling like "we just can't get aligned."
It's not that alignment is impossible. It's that you're trying to align people who are playing different games on different fields with different rules.
An objective fixes this. It doesn't eliminate different perspectives, you still want those. But it gives everyone a common scoreboard.
If the objective is "Identify the initiative that will generate the most expansion revenue from existing customers in the next six months," then suddenly:
Sales can't just argue for "more products" without showing how it drives expansion revenue.
Product can't just defend the current roadmap without proving it solves the expansion problem.
Finance can't just focus on margins without acknowledging that expansion revenue is the priority.
The CEO has a clear tiebreaker when opinions conflict.
The objective keeps everyone on the same page, not because it eliminates disagreement, but because it makes the disagreement productive.
You're no longer arguing about whether the idea is good in general. You're arguing about whether it achieves this specific objective. And that's a much more solvable problem.
This was the missing piece at that offsite. We had all the right people in the room, and they all had valid concerns. But we were having five different conversations at once, and none of them were moving us toward a decision.
Now let me show you how the framework I built prevents that from happening.
The Framework I Built From That Failure
What I developed after that disastrous offsite is something I call Objective-Based Constrained Thinking, OBCT for short. It's not complicated. In fact, that's the point. It's a simple, layered approach that transforms vague conversations into structured decisions.
The core idea is this: before you discuss anything, define what you're solving for (your objective) and what boundaries you'll respect (your constraints), in layers that evolve as clarity increases.
Think of it as GPS for meetings. You need a destination, and you need to know which roads are actually available. Without both, you're just driving in circles and burning gas.
Here's how it works, step by step.
Step 1: Declare the Objective
The Question: What are we trying to achieve in this discussion or decision?
This sounds obvious, but as I learned in that conference room with the view, most meetings skip it entirely. They have a topic ("Q4 Planning" or "Product Roadmap" or "Annual Strategic Planning"), but not an objective, a specific outcome they're trying to reach.
Here's the difference:
Topic: "Let's discuss growth."
Objective: "Determine which growth lever to prioritize next quarter."
See how the second one changes everything? It tells you what success looks like. It tells you when you're done. It tells you what kinds of conversations are productive and which ones are distractions.
And critically, it aligns everyone's individual perspectives toward a common goal.
When your VP of Sales walks into a meeting about "growth" without an objective, they're thinking about quota and pipeline. When your CFO walks in, they're thinking about profitability and cash flow. When your Head of Product walks in, they're thinking about roadmap capacity and technical feasibility.
All valid concerns. But they're not the same concern.
When you declare the objective as "Determine which growth lever will generate the most expansion revenue from existing customers in Q1," suddenly everyone knows what game they're playing. Sales can't just advocate for "more leads" if leads don't drive expansion. Finance can't just focus on cutting costs if the goal is expansion revenue. Product can't just protect the roadmap without showing how it drives the objective.
The objective doesn't silence different viewpoints, it channels them toward a common destination.
If I could go back to that offsite, I would have written on the whiteboard before anyone said a word:
Objective: Identify and commit to two specific growth initiatives for next year, with assigned owners and success metrics.
That one sentence would have saved us hours, and would have prevented the Sales team from advocating for "more products" and the CFO from arguing for "better margins" when neither was actually the question we needed to answer.
How to Write a Good Objective
A well-formed objective is:
Specific: Not "improve the product," but "define the core problem our new product feature is solving."
Actionable: It points toward a decision, not just awareness or discussion.
Scoped: It's achievable in the time you've allocated.
Unifying: It gives everyone a common scoreboard to evaluate ideas against.
More examples:
Bad: "Talk about customer retention"
Good: "Decide whether to invest in customer success headcount or automated onboarding for Q1"
Bad: "Review marketing performance"
Good: "Identify the top-performing channel and commit to a 6-month doubling-down strategy"
So now, before any meeting I run starts, I write the objective at the top of the agenda. I say it out loud. I make sure everyone agrees on it. And if they don't? We figure that out before we waste an hour going in different directions.
Because when everyone's rowing toward the same destination, different perspectives become strengths instead of sources of conflict.
Step 2: Establish the First-Order Constraint
The Question: What boundaries define success?
Once you know what you're trying to achieve, you need to narrow the field. This is where constraints come in, and I know "constraint" sounds limiting, but that's exactly the point. Constraints aren't creativity killers; they're focus enablers.
Let's say your objective is: "Grow the business next year."
That's a start, but it's still too open-ended. Growth could mean a thousand things. So you establish a first-order constraint, a strategic lens that filters your options.
Example First-Order Constraints:
Option A: Grow market share (win more customers in your current market)
Option B: Broaden addressable market (enter new segments or geographies)
Option C: Both, if we can prove we have the capacity and differentiation to execute on two fronts
Notice what just happened. You went from "infinite possibilities" to "three paths." That's the power of a well-chosen constraint.
At that offsite I told you about? We never established this. So when someone proposed that partnership idea, we had no way to evaluate it. Did it help us grow market share? Expand to new markets? Improve retention? We didn't know, because we hadn't decided what we were optimizing for.
And because we hadn't set a constraint, each person evaluated the idea through their own lens:
Sales thought: "Will this give me more things to sell?"
Product thought: "Will this distract from my roadmap?"
Finance thought: "Will this be profitable?"
The CEO thought: "Will this look good?"
All reasonable questions. But they weren't the same question, so we couldn't reach a conclusion.
Now, when someone proposes an idea in one of my meetings, I can ask: "Does this help us grow market share, or expand our addressable market, or both?" If the answer is "neither," we table it. If it's "one of them," we evaluate it against that constraint. If it's "both," we dig deeper to see if it's realistic.
This eliminates vague brainstorming and anchors the group in bounded exploration.
You're not shutting down creativity, you're channeling it. Think of it like a river: unbounded water spreads into a swamp, but water within banks becomes a powerful current.
Step 3: Apply Second-Order Constraints
The Question: Within those boundaries, what specific paths exist?
This is where you zoom in. First-order constraints set the strategic direction. Second-order constraints define the tactical options within that direction.
Let's continue the example. You've decided your first-order constraint is "Grow market share" (win more customers in your current market).
Great. Now you need to get specific. How do you actually do that? Your second-order constraints might include:
Complete market "must-haves" — Add the table-stakes features your competitors have that you're missing (you're losing deals because of gaps).
Add or reinforce differentiators — Double down on what makes you unique (you're winning deals, but not enough people know about you).
Improve customer retention — Keep the customers you have (churn is killing your growth before it starts).
Each of these is a valid path, but they require different resources, timelines, and risks. By laying them out as explicit constraints, you force the team to choose, or at least to acknowledge the trade-offs.
Why This Matters
Without second-order constraints, you get analysis paralysis. Everyone agrees on the destination (grow market share), but no one can agree on the route. Some people want to build features. Others want to fix retention. Others want to invest in brand.
All of those might be good ideas, but you can't do everything at once, especially not if you're a startup or a growing company with limited resources. Second-order constraints force prioritization by making the options explicit and comparable.
Each layer defines the next set of valid conversations and automatically filters out noise.
When I think back to that offsite, we debated whether to hire more salespeople or invest in marketing automation. Both reasonable ideas (but not strategic). But we never established whether our constraint was "acquire more customers" or "convert more leads" or "retain existing customers longer." Without that context, we were comparing apples to oranges to airplanes.
And of course, Sales advocated for more headcount (because that's what helps Sales hit quota), while Finance advocated for automation (because that's what helps Finance hit margin targets). Neither was wrong. But neither was answering the right question, because we hadn't defined what the right question was.
Step 4: Navigate Using Constraint Loops
Here's where the framework becomes a living tool, not just a planning exercise.
Meetings drift. It's human nature. Someone raises an interesting tangent, and before you know it, you're debating office perks when you were supposed to be deciding on a product roadmap. (Yes, this has happened to me. More than once.)
The OBCT loop is your guardrail. When the conversation drifts, pause and ask:
"Does this align with our current objective and constraint set?"
If yes, continue. If no, you have two options:
Note it for later — "Great point, but let's table it for now and come back to it after we close this decision."
Redefine the constraint — "This discussion is revealing that our constraint might be wrong. Should we adjust?"
Why Constraints Evolve
Here's the key insight that took me a while to learn: Constraints aren't cages; they're focus tools that evolve with understanding.
Sometimes, the act of exploring within a constraint reveals that the constraint itself was too narrow or aimed at the wrong thing. That's fine. The framework gives you permission to adjust, but it forces you to do so consciously, not accidentally.
For example, you might start with "grow market share" and realize mid-discussion that your real bottleneck is retention, not acquisition. Customer acquisition is actually going great, they're just churning out the back door. At that point, you explicitly reframe: "It sounds like we need to shift our first-order constraint from growth to retention. Does everyone agree?"
Now you're not drifting, you're pivoting with intention. There's a huge difference.
At that offsite, we drifted from partnerships to pricing to org structure to marketing messaging without ever acknowledging we'd changed topics. If we'd been using the OBCT loop, someone could have said, "Hold on, we're now talking about pricing, but our objective was about growth levers. Is pricing a lever we want to evaluate, or are we off track?"
That one question would have saved us.
Step 5: End With Convergence
This is the step most meetings skip, and it's the reason nothing ever gets done.
I've been in so many meetings that end with "Great discussion, let's pick this up next time," and then next time, we start from scratch because nobody remembers what we decided or why.
Every OBCT discussion should end with three things clearly stated and written down:
1. Restated Objective
Did we achieve it? Did we need to reframe it?
"We set out to determine which growth lever to prioritize. We decided it's customer retention through improved onboarding."
2. Final Constraint Set
What's the next boundary for action?
"Our second-order constraints are: (1) automate the first 48 hours of user experience, (2) launch a customer success check-in at day 30."
3. Next Objective
What comes after this decision?
"Next meeting: Define success metrics for the new onboarding flow and assign owners."
That way, each meeting hands the next one a clear runway, no re-hashing, no fog.
You're not just ending the meeting, you're launching the next one. And the next one. And the next one. Each with clarity, each with momentum.
That offsite I mentioned? We left with action items like "explore partnership opportunities" and "think about market expansion." Which is a fancy way of saying we left with homework but no decisions.
If we'd ended with convergence, we would have left with: "We've decided to focus on growing market share before expanding markets. Our next objective is to choose between completing must-have features or improving retention. That decision will be made in two weeks after we review customer churn data."
See the difference?
Why This Framework Works: The Psychology of Bounded Exploration
There's a reason the OBCT framework feels so effective once you start using it: it aligns with how our brains actually make decisions.
Cognitive research shows that humans struggle with unbounded choice. Give someone infinite options, and they freeze. Give them three clear paths, and they can evaluate, compare, and decide. This is why restaurants with 100-item menus are stressful, but prix fixe menus feel luxurious. This is why "let's discuss strategy" makes people anxious, but "choose between option A and option B" makes them feel productive.
OBCT does the same thing for strategic thinking. It doesn't limit creativity, it channels it. It says: "Here's the sandbox. Build anything you want inside it, and if you need a bigger sandbox, we'll talk about that too."
This has a second-order effect that I didn't expect when I first started using the framework: it makes meetings psychologically safer.
When everyone knows what's in scope and what's not, people feel more comfortable contributing. They're not worried about being off-topic or wasting time. They know their idea will either fit within the current constraint (and be evaluated fairly) or get noted for a future discussion. Nobody's idea gets dismissed as "not strategic" without context, it either fits the current objective or it gets its own objective later.
I've noticed that quieter people speak up more in OBCT meetings. Because the structure protects them from being steamrolled by the loudest voice in the room.
And crucially, the framework neutralizes departmental politics.
When Sales pushes for lower pricing or more features, you don't have to argue about whether that's "the right thing to do" in some abstract sense. You just ask: "Does this achieve our stated objective?" If yes, evaluate it. If no, defer it. The objective becomes the referee, not the highest-paid person in the room.
Putting OBCT Into Practice: A Real-World Example
Let me walk you through how this might play out in a real meeting, because I want you to see the contrast between the old way and the new way.
Context: You're a startup planning your product roadmap for the next six months.
Before OBCT (The Old Way):
The meeting starts with "Let's talk about the roadmap." Two hours later, you've debated:
Whether to build a mobile app
Whether to add enterprise features
Whether to redesign the UI
Whether to focus on performance improvements
Whether to integrate with third-party tools
Someone mentions AI because, well, everyone's talking about AI. Someone else brings up a competitor feature. The designer wants to fix the onboarding flow. The engineer wants to refactor the backend.
All valid points. All interesting. None of them clearly more important than the others.
And here's what's happening under the surface:
Sales is pushing for enterprise features because they keep losing deals to competitors who have them
Product is pushing for the UI redesign because they're embarrassed by the current interface
Engineering is pushing for the refactor because the code is becoming unmaintainable
The CEO is pushing for AI features because that's what investors want to hear about
Everyone has a legitimate concern. Everyone's advocating for what makes sense from their seat. And because there's no objective, everyone's pitching ideas that optimize for their own success metrics.
No decision is made. Everyone's frustrated. You schedule a follow-up meeting to "narrow things down." Which will take another two hours and probably also end without a decision.
With OBCT (The New Way):
You start the meeting by writing on the whiteboard:
Objective: "Decide which product direction will most directly impact revenue in the next six months."
Everyone agrees on the objective. Already you've saved fifteen minutes of "wait, what are we doing here?" And more importantly, you've given Sales, Product, Engineering, and the CEO a common scoreboard.
Now when Sales pitches enterprise features, they can't just say "we need these to win deals." They have to show how those features will impact revenue in six months. When Product pitches the UI redesign, they have to connect it to revenue. When Engineering pitches the refactor, same thing.
First-Order Constraint: "We can either (A) deepen value for existing customers to drive expansion revenue, or (B) add features to win new customer segments."
The team discusses both paths. You look at your data. Your sales pipeline is healthy, you're signing new customers at a decent clip. But your expansion revenue is flat. Customers sign on, use the basic tier, and stay there. You're not moving them up-market.
You choose: "Deepen value for existing customers."
Now you're not debating mobile apps vs. enterprise features in a vacuum. You're asking: which one deepens value for existing customers?
Second-Order Constraints: Within that, you have three options:
Add integrations that make the product stickier
Build analytics features that customers are asking for
Improve onboarding so customers reach value faster
Someone proposes the mobile app. You ask: "Does this deepen value for existing customers?"
"Well," they say, "it would make it easier to use the product on the go."
"True," you say, "but is that why expansion revenue is flat? Or is it because customers don't see enough value in the advanced features to upgrade?"
Pause. "Probably the second one."
"Okay. So let's note the mobile app for later, but it doesn't fit our current constraint. We're focused on deepening value to drive expansion."
The idea isn't dismissed. It's deferred. Big difference.
After 45 minutes of focused discussion, you decide: Build the analytics features (highest customer request volume, clearest ROI, most likely to drive upgrades).
Next Objective: "Define what 'analytics features' means in detail and scope the MVP."
You end the meeting with clarity, a decision, and a clear next step. No follow-up needed just to figure out what you were supposed to decide.
Total meeting time: One hour.
This is not hypothetical. I've run this exact meeting. Multiple times. The first time I used OBCT, I was shocked at how much faster we moved, and how much better people felt about the outcome.
Because everyone's concerns were heard. But they were evaluated against a common objective, not against each other's departmental goals.
Common Pitfalls (and How to Avoid Them)
I've been using this framework for a few years now, and I've seen the same mistakes come up over and over. Here are the big ones:
Pitfall #1: Setting Constraints Too Narrow
If your constraint is "We can only do X," you've killed the conversation before it starts. That's not a constraint, that's a foregone conclusion pretending to be a discussion.
Good constraints create a bounded space for exploration, not a single predetermined answer.
Fix: Frame constraints as "either/or" or "these are the paths available" rather than "this is the only option."
Pitfall #2: Skipping the Objective
This is the mistake we made at that offsite. Jumping straight into constraints without a clear objective means you're optimizing for the wrong thing, or for nothing at all.
Fix: Always start with "What are we trying to achieve?" and get explicit agreement before you move forward.
Pitfall #3: Treating Constraints as Permanent
Constraints should evolve as you learn. If the discussion reveals that your constraint is wrong, change it. Don't stubbornly stick to a framework when reality is telling you something different.
Fix: Use the constraint loop, check in regularly and ask if the current framing still makes sense.
Pitfall #4: Not Writing It Down
This seems small, but it's huge. If the objective and constraints aren't visible to everyone in the room, on a whiteboard, on a screen, in the shared notes, people will forget them. And you'll drift.
Fix: Write it down at the start. Keep it visible. Refer back to it.
Pitfall #5: Letting Departmental Goals Masquerade as Objectives
This is subtle but critical. Sometimes what sounds like an objective is actually just one person's departmental goal dressed up as a company objective.
"Increase sales pipeline by 40%" sounds like an objective, but it's really a Sales goal. "Launch three new features" sounds like an objective, but it's really a Product goal.
A real objective transcends departments. "Achieve $10M ARR by year-end" is an objective everyone can rally around, even if it requires different things from different teams.
Fix: Test your objective by asking: "Would every department in this room measure success the same way?" If not, keep refining.
What I Wish I'd Said at That Offsite
If I could go back to that conference room with the mountain view and the cold buffet lunch, here's what I would have done differently.
Before the CEO said "Let's talk about strategy," I would have stood up and said:
"Before we start, can we agree on three things?"
1. The objective for this offsite: "By the end of today, we will have identified two growth levers for next year, assigned owners, and defined success metrics."
2. Our first-order constraint: "We will focus on growth that leverages our existing capabilities and market position, not on entirely new markets or products."
3. How we'll know we succeeded: "We leave with two clear initiatives, documented owners, and a plan to check progress in 30 days."
Then I would have written those three things on the whiteboard in giant letters. And every time the conversation drifted, which it would have, because that's what conversations do, I would have pointed at the board and asked: "Does this align with our objective and constraint?"
And when Sales started pushing for more products and Finance started pushing for better margins and Product started defending the roadmap, I would have said: "All valid concerns. But our objective today is to identify growth levers, not to solve every problem. Let's evaluate each idea against that objective. If it doesn't fit, we'll note it for a future discussion."
We would have still gone out for that nice lunch. We would have still had the beautiful view.
But we wouldn't have left with pages of notes that went nowhere.
We would have left with a plan. And everyone would have been aligned on what we were trying to achieve, not because they all agreed on everything, but because they all agreed on what question we were answering.
The Bottom Line
The OBCT framework isn't magic. It's just structure, but structure is exactly what most strategic conversations lack.
By forcing yourself to answer two simple questions, What are we solving for? and What boundaries will we respect?. You turn vague discussions into focused decisions. You make meetings productive. You make progress visible. You stop confusing activity with achievement.
And you give people with different perspectives a common language to collaborate instead of compete.
Because the truth is, you need those different perspectives. You need Sales to tell you what customers are asking for. You need Finance to tell you what's financially viable. You need Product to tell you what's technically feasible. You need the CEO to tell you what aligns with the company's strategic direction.
But without an objective to unite them, those perspectives become sources of conflict instead of sources of insight.
The OBCT framework doesn't eliminate disagreement. It makes disagreement productive. It turns "Sales wants features and Finance wants margins" into "Given our objective of driving expansion revenue, which investment, features or margins, will get us there faster?"
Same people. Same perspectives. Completely different outcome.
And here's the best part: once you start using OBCT, you'll notice how many conversations around you are stuck because they're missing it. You'll see the drift, the circular arguments, the false consensus that leads nowhere. You'll watch hour-long meetings accomplish what could have taken fifteen minutes if anyone had just asked, "What's the objective here?"
You'll become the person who says, "Before we go further, what are we trying to achieve?"
And everyone in the room will breathe a sigh of relief, because finally, someone's steering the plane.
So here's my challenge to you: In your next important meeting, before anyone says anything else, write three things at the top of the agenda or on the whiteboard:
Objective:
First-Order Constraint:
Decision to Make:
Then see what happens.
I'm willing to bet you'll get more done in 30 minutes than you usually do in two hours.
Because once you know where you're going and which roads are available, the destination becomes inevitable.
And you'll never waste another offsite staring at the view while your strategy goes nowhere.
The Offsite That Went Nowhere
It was our annual strategic planning offsite, which, by title alone, implied gravitas. The kind of event where you book a nice hotel, order a buffet lunch that costs more than most people's weekly grocery bill, and convince yourself that being offsite somehow makes the thinking more strategic.
It didn't.
There were no clear objectives. No defined outcomes. Just the words "Annual Strategic Planning" sitting on the agenda like a promise of direction that never arrived, a placeholder for importance we hadn't actually earned.
We gathered in a conference room with a view, laptops open, caffeine flowing, notebooks pristine and ready to capture insights. We were going to "shape the future." The CEO kicked things off with enthusiasm and a confident smile: "Alright, let's talk about next year's strategy."
It didn’t take long before someone said it, the four words that derail more meetings than any others:
"I have an idea."
The idea wasn't bad. Actually, it was pretty good. It involved a partnership with a company that was gaining traction in our space, and it sounded plausible enough that nobody wanted to be the person to shoot it down immediately. Slides came out. Someone pulled up their financial model. Side conversations started about who would own the relationship. And suddenly we were knee-deep in pricing debates, hypothetical org charts, and "what if" scenarios about market positioning.
For twenty minutes, the room hummed with energy. People were engaged. We were doing strategy.
But here's what we weren't doing: answering any coherent question.
The idea stood alone, a shiny object that had hijacked the agenda. It wasn't connected to any declared objective. We hadn't defined what success looked like for the year, or for the meeting, or even for that conversation. We hadn't established whether we were trying to grow revenue, expand market share, enter new segments, or fix operational problems. We were just... talking about an idea because it seemed interesting.
After watching this unfold for long enough that the buffet lunch was getting cold, I finally asked the question that stopped the momentum like a record scratch:
"What's the objective of this meeting? What are we actually trying to achieve?"
Silence.
Then the nervous laughter that says, we probably should've figured that out beforehand.
The CEO looked at the agenda. Someone else looked at their laptop. A few people looked at me like I'd just asked why we breathe oxygen, something so obvious it shouldn't need to be said, yet nobody had an answer.
"Well," someone finally offered, "we're here to plan strategy for next year."
"Right," I said. "But what does that mean? Are we trying to decide between growth options? Identify our biggest risk? Commit to specific initiatives? All of the above? Something else?"
More silence. And that's when it hit me with uncomfortable clarity:
Most so-called strategy sessions fail not because people lack ideas, but because they lack objective-based constraints.
Everyone's rowing hard, but nobody's steering. We had smart people, good intentions, decent ideas, and a beautiful view. What we didn't have was structure.
An objective gives you a path to measure success. It lets you ask, at the end of the meeting, did we achieve what we set out to achieve, or did we just talk about interesting things?
A constraint defines where to focus, the edges of what matters, so the discussion stays useful instead of sprawling into every direction at once.
If our objective had been clear, "Identify two growth levers for next year and assign owners" and our constraint explicit, "Focus on expanding market share in our current market before considering new markets," we'd have known immediately what belonged in the discussion and what didn't.
That partnership idea? Maybe it fit. Maybe it didn't. But we couldn't evaluate it because we had no criteria for evaluation.
Instead, we left the offsite at 4 PM with pages of notes, scattered action items nobody would remember in a week, and no real decisions. It felt like progress because we'd been talking for six hours. It wasn't progress. It was just an expensive way to avoid making hard choices.
I drove home frustrated, and over the next few weeks, that frustration crystallized into something more useful: a framework.
Now, before any meeting begins, especially the important ones, I start with two questions:
What is the objective?
What are the constraints?
Because without those, even the best ideas are just noise. And even the most expensive offsite is just a scenic way to waste time.
Let me show you how this works.
The Hidden Problem: Everyone's Optimizing for Their Own Scoreboard
Before I dive into the framework, I need to address something that took me years to fully understand: why smart, well-intentioned people in the same company can spend hours in a room and make no progress.
It's not just that meetings lack structure. It's that every person at the table is optimizing for a different outcome, often without realizing it.
Think about who shows up to a strategic planning meeting:
Sales wants lower pricing, more features, more products, faster delivery, and whatever else will help them close deals this quarter.
Product wants time to build things right, fewer feature requests, and the freedom to focus on technical debt and user experience.
Finance wants predictable revenue, better margins, and cost control.
Marketing wants budget, creative freedom, and lead generation targets that are actually achievable.
The C-suite wants growth, profitability, market position, and something impressive to tell the board.
Here's the thing: none of these perspectives are wrong. In fact, having different viewpoints at a meeting is often valuable, it's how you spot blind spots, challenge assumptions, and avoid groupthink.
But it's also a massive source of unproductive conflict.
At that offsite I described, when we started discussing the partnership idea, here's what was actually happening under the surface:
The VP of Sales loved it because it would give them a new product to sell and access to the partner's customer base.
The CFO was skeptical because partnerships are notoriously hard to forecast and don't always generate the revenue you think they will.
The Head of Product was worried it would distract from the roadmap and create technical dependencies.
The CEO liked the optics of announcing a high-profile partnership but wasn't sure if it was the highest leverage move.
So we spent a long time debating, but we weren't really debating the same question. Sales was debating "will this help me hit quota?" Finance was debating "will this be profitable?" Product was debating "will this derail our existing plans?" And the CEO was debating "is this the best use of our limited resources?"
Without a clear objective, every person was scoring the idea against their own department's goals, not the company's goals.
This is why meetings spiral. This is why the same arguments happen over and over. This is why you leave feeling like "we just can't get aligned."
It's not that alignment is impossible. It's that you're trying to align people who are playing different games on different fields with different rules.
An objective fixes this. It doesn't eliminate different perspectives, you still want those. But it gives everyone a common scoreboard.
If the objective is "Identify the initiative that will generate the most expansion revenue from existing customers in the next six months," then suddenly:
Sales can't just argue for "more products" without showing how it drives expansion revenue.
Product can't just defend the current roadmap without proving it solves the expansion problem.
Finance can't just focus on margins without acknowledging that expansion revenue is the priority.
The CEO has a clear tiebreaker when opinions conflict.
The objective keeps everyone on the same page, not because it eliminates disagreement, but because it makes the disagreement productive.
You're no longer arguing about whether the idea is good in general. You're arguing about whether it achieves this specific objective. And that's a much more solvable problem.
This was the missing piece at that offsite. We had all the right people in the room, and they all had valid concerns. But we were having five different conversations at once, and none of them were moving us toward a decision.
Now let me show you how the framework I built prevents that from happening.
The Framework I Built From That Failure
What I developed after that disastrous offsite is something I call Objective-Based Constrained Thinking, OBCT for short. It's not complicated. In fact, that's the point. It's a simple, layered approach that transforms vague conversations into structured decisions.
The core idea is this: before you discuss anything, define what you're solving for (your objective) and what boundaries you'll respect (your constraints), in layers that evolve as clarity increases.
Think of it as GPS for meetings. You need a destination, and you need to know which roads are actually available. Without both, you're just driving in circles and burning gas.
Here's how it works, step by step.
Step 1: Declare the Objective
The Question: What are we trying to achieve in this discussion or decision?
This sounds obvious, but as I learned in that conference room with the view, most meetings skip it entirely. They have a topic ("Q4 Planning" or "Product Roadmap" or "Annual Strategic Planning"), but not an objective, a specific outcome they're trying to reach.
Here's the difference:
Topic: "Let's discuss growth."
Objective: "Determine which growth lever to prioritize next quarter."
See how the second one changes everything? It tells you what success looks like. It tells you when you're done. It tells you what kinds of conversations are productive and which ones are distractions.
And critically, it aligns everyone's individual perspectives toward a common goal.
When your VP of Sales walks into a meeting about "growth" without an objective, they're thinking about quota and pipeline. When your CFO walks in, they're thinking about profitability and cash flow. When your Head of Product walks in, they're thinking about roadmap capacity and technical feasibility.
All valid concerns. But they're not the same concern.
When you declare the objective as "Determine which growth lever will generate the most expansion revenue from existing customers in Q1," suddenly everyone knows what game they're playing. Sales can't just advocate for "more leads" if leads don't drive expansion. Finance can't just focus on cutting costs if the goal is expansion revenue. Product can't just protect the roadmap without showing how it drives the objective.
The objective doesn't silence different viewpoints, it channels them toward a common destination.
If I could go back to that offsite, I would have written on the whiteboard before anyone said a word:
Objective: Identify and commit to two specific growth initiatives for next year, with assigned owners and success metrics.
That one sentence would have saved us hours, and would have prevented the Sales team from advocating for "more products" and the CFO from arguing for "better margins" when neither was actually the question we needed to answer.
How to Write a Good Objective
A well-formed objective is:
Specific: Not "improve the product," but "define the core problem our new product feature is solving."
Actionable: It points toward a decision, not just awareness or discussion.
Scoped: It's achievable in the time you've allocated.
Unifying: It gives everyone a common scoreboard to evaluate ideas against.
More examples:
Bad: "Talk about customer retention"
Good: "Decide whether to invest in customer success headcount or automated onboarding for Q1"
Bad: "Review marketing performance"
Good: "Identify the top-performing channel and commit to a 6-month doubling-down strategy"
So now, before any meeting I run starts, I write the objective at the top of the agenda. I say it out loud. I make sure everyone agrees on it. And if they don't? We figure that out before we waste an hour going in different directions.
Because when everyone's rowing toward the same destination, different perspectives become strengths instead of sources of conflict.
Step 2: Establish the First-Order Constraint
The Question: What boundaries define success?
Once you know what you're trying to achieve, you need to narrow the field. This is where constraints come in, and I know "constraint" sounds limiting, but that's exactly the point. Constraints aren't creativity killers; they're focus enablers.
Let's say your objective is: "Grow the business next year."
That's a start, but it's still too open-ended. Growth could mean a thousand things. So you establish a first-order constraint, a strategic lens that filters your options.
Example First-Order Constraints:
Option A: Grow market share (win more customers in your current market)
Option B: Broaden addressable market (enter new segments or geographies)
Option C: Both, if we can prove we have the capacity and differentiation to execute on two fronts
Notice what just happened. You went from "infinite possibilities" to "three paths." That's the power of a well-chosen constraint.
At that offsite I told you about? We never established this. So when someone proposed that partnership idea, we had no way to evaluate it. Did it help us grow market share? Expand to new markets? Improve retention? We didn't know, because we hadn't decided what we were optimizing for.
And because we hadn't set a constraint, each person evaluated the idea through their own lens:
Sales thought: "Will this give me more things to sell?"
Product thought: "Will this distract from my roadmap?"
Finance thought: "Will this be profitable?"
The CEO thought: "Will this look good?"
All reasonable questions. But they weren't the same question, so we couldn't reach a conclusion.
Now, when someone proposes an idea in one of my meetings, I can ask: "Does this help us grow market share, or expand our addressable market, or both?" If the answer is "neither," we table it. If it's "one of them," we evaluate it against that constraint. If it's "both," we dig deeper to see if it's realistic.
This eliminates vague brainstorming and anchors the group in bounded exploration.
You're not shutting down creativity, you're channeling it. Think of it like a river: unbounded water spreads into a swamp, but water within banks becomes a powerful current.
Step 3: Apply Second-Order Constraints
The Question: Within those boundaries, what specific paths exist?
This is where you zoom in. First-order constraints set the strategic direction. Second-order constraints define the tactical options within that direction.
Let's continue the example. You've decided your first-order constraint is "Grow market share" (win more customers in your current market).
Great. Now you need to get specific. How do you actually do that? Your second-order constraints might include:
Complete market "must-haves" — Add the table-stakes features your competitors have that you're missing (you're losing deals because of gaps).
Add or reinforce differentiators — Double down on what makes you unique (you're winning deals, but not enough people know about you).
Improve customer retention — Keep the customers you have (churn is killing your growth before it starts).
Each of these is a valid path, but they require different resources, timelines, and risks. By laying them out as explicit constraints, you force the team to choose, or at least to acknowledge the trade-offs.
Why This Matters
Without second-order constraints, you get analysis paralysis. Everyone agrees on the destination (grow market share), but no one can agree on the route. Some people want to build features. Others want to fix retention. Others want to invest in brand.
All of those might be good ideas, but you can't do everything at once, especially not if you're a startup or a growing company with limited resources. Second-order constraints force prioritization by making the options explicit and comparable.
Each layer defines the next set of valid conversations and automatically filters out noise.
When I think back to that offsite, we debated whether to hire more salespeople or invest in marketing automation. Both reasonable ideas (but not strategic). But we never established whether our constraint was "acquire more customers" or "convert more leads" or "retain existing customers longer." Without that context, we were comparing apples to oranges to airplanes.
And of course, Sales advocated for more headcount (because that's what helps Sales hit quota), while Finance advocated for automation (because that's what helps Finance hit margin targets). Neither was wrong. But neither was answering the right question, because we hadn't defined what the right question was.
Step 4: Navigate Using Constraint Loops
Here's where the framework becomes a living tool, not just a planning exercise.
Meetings drift. It's human nature. Someone raises an interesting tangent, and before you know it, you're debating office perks when you were supposed to be deciding on a product roadmap. (Yes, this has happened to me. More than once.)
The OBCT loop is your guardrail. When the conversation drifts, pause and ask:
"Does this align with our current objective and constraint set?"
If yes, continue. If no, you have two options:
Note it for later — "Great point, but let's table it for now and come back to it after we close this decision."
Redefine the constraint — "This discussion is revealing that our constraint might be wrong. Should we adjust?"
Why Constraints Evolve
Here's the key insight that took me a while to learn: Constraints aren't cages; they're focus tools that evolve with understanding.
Sometimes, the act of exploring within a constraint reveals that the constraint itself was too narrow or aimed at the wrong thing. That's fine. The framework gives you permission to adjust, but it forces you to do so consciously, not accidentally.
For example, you might start with "grow market share" and realize mid-discussion that your real bottleneck is retention, not acquisition. Customer acquisition is actually going great, they're just churning out the back door. At that point, you explicitly reframe: "It sounds like we need to shift our first-order constraint from growth to retention. Does everyone agree?"
Now you're not drifting, you're pivoting with intention. There's a huge difference.
At that offsite, we drifted from partnerships to pricing to org structure to marketing messaging without ever acknowledging we'd changed topics. If we'd been using the OBCT loop, someone could have said, "Hold on, we're now talking about pricing, but our objective was about growth levers. Is pricing a lever we want to evaluate, or are we off track?"
That one question would have saved us.
Step 5: End With Convergence
This is the step most meetings skip, and it's the reason nothing ever gets done.
I've been in so many meetings that end with "Great discussion, let's pick this up next time," and then next time, we start from scratch because nobody remembers what we decided or why.
Every OBCT discussion should end with three things clearly stated and written down:
1. Restated Objective
Did we achieve it? Did we need to reframe it?
"We set out to determine which growth lever to prioritize. We decided it's customer retention through improved onboarding."
2. Final Constraint Set
What's the next boundary for action?
"Our second-order constraints are: (1) automate the first 48 hours of user experience, (2) launch a customer success check-in at day 30."
3. Next Objective
What comes after this decision?
"Next meeting: Define success metrics for the new onboarding flow and assign owners."
That way, each meeting hands the next one a clear runway, no re-hashing, no fog.
You're not just ending the meeting, you're launching the next one. And the next one. And the next one. Each with clarity, each with momentum.
That offsite I mentioned? We left with action items like "explore partnership opportunities" and "think about market expansion." Which is a fancy way of saying we left with homework but no decisions.
If we'd ended with convergence, we would have left with: "We've decided to focus on growing market share before expanding markets. Our next objective is to choose between completing must-have features or improving retention. That decision will be made in two weeks after we review customer churn data."
See the difference?
Why This Framework Works: The Psychology of Bounded Exploration
There's a reason the OBCT framework feels so effective once you start using it: it aligns with how our brains actually make decisions.
Cognitive research shows that humans struggle with unbounded choice. Give someone infinite options, and they freeze. Give them three clear paths, and they can evaluate, compare, and decide. This is why restaurants with 100-item menus are stressful, but prix fixe menus feel luxurious. This is why "let's discuss strategy" makes people anxious, but "choose between option A and option B" makes them feel productive.
OBCT does the same thing for strategic thinking. It doesn't limit creativity, it channels it. It says: "Here's the sandbox. Build anything you want inside it, and if you need a bigger sandbox, we'll talk about that too."
This has a second-order effect that I didn't expect when I first started using the framework: it makes meetings psychologically safer.
When everyone knows what's in scope and what's not, people feel more comfortable contributing. They're not worried about being off-topic or wasting time. They know their idea will either fit within the current constraint (and be evaluated fairly) or get noted for a future discussion. Nobody's idea gets dismissed as "not strategic" without context, it either fits the current objective or it gets its own objective later.
I've noticed that quieter people speak up more in OBCT meetings. Because the structure protects them from being steamrolled by the loudest voice in the room.
And crucially, the framework neutralizes departmental politics.
When Sales pushes for lower pricing or more features, you don't have to argue about whether that's "the right thing to do" in some abstract sense. You just ask: "Does this achieve our stated objective?" If yes, evaluate it. If no, defer it. The objective becomes the referee, not the highest-paid person in the room.
Putting OBCT Into Practice: A Real-World Example
Let me walk you through how this might play out in a real meeting, because I want you to see the contrast between the old way and the new way.
Context: You're a startup planning your product roadmap for the next six months.
Before OBCT (The Old Way):
The meeting starts with "Let's talk about the roadmap." Two hours later, you've debated:
Whether to build a mobile app
Whether to add enterprise features
Whether to redesign the UI
Whether to focus on performance improvements
Whether to integrate with third-party tools
Someone mentions AI because, well, everyone's talking about AI. Someone else brings up a competitor feature. The designer wants to fix the onboarding flow. The engineer wants to refactor the backend.
All valid points. All interesting. None of them clearly more important than the others.
And here's what's happening under the surface:
Sales is pushing for enterprise features because they keep losing deals to competitors who have them
Product is pushing for the UI redesign because they're embarrassed by the current interface
Engineering is pushing for the refactor because the code is becoming unmaintainable
The CEO is pushing for AI features because that's what investors want to hear about
Everyone has a legitimate concern. Everyone's advocating for what makes sense from their seat. And because there's no objective, everyone's pitching ideas that optimize for their own success metrics.
No decision is made. Everyone's frustrated. You schedule a follow-up meeting to "narrow things down." Which will take another two hours and probably also end without a decision.
With OBCT (The New Way):
You start the meeting by writing on the whiteboard:
Objective: "Decide which product direction will most directly impact revenue in the next six months."
Everyone agrees on the objective. Already you've saved fifteen minutes of "wait, what are we doing here?" And more importantly, you've given Sales, Product, Engineering, and the CEO a common scoreboard.
Now when Sales pitches enterprise features, they can't just say "we need these to win deals." They have to show how those features will impact revenue in six months. When Product pitches the UI redesign, they have to connect it to revenue. When Engineering pitches the refactor, same thing.
First-Order Constraint: "We can either (A) deepen value for existing customers to drive expansion revenue, or (B) add features to win new customer segments."
The team discusses both paths. You look at your data. Your sales pipeline is healthy, you're signing new customers at a decent clip. But your expansion revenue is flat. Customers sign on, use the basic tier, and stay there. You're not moving them up-market.
You choose: "Deepen value for existing customers."
Now you're not debating mobile apps vs. enterprise features in a vacuum. You're asking: which one deepens value for existing customers?
Second-Order Constraints: Within that, you have three options:
Add integrations that make the product stickier
Build analytics features that customers are asking for
Improve onboarding so customers reach value faster
Someone proposes the mobile app. You ask: "Does this deepen value for existing customers?"
"Well," they say, "it would make it easier to use the product on the go."
"True," you say, "but is that why expansion revenue is flat? Or is it because customers don't see enough value in the advanced features to upgrade?"
Pause. "Probably the second one."
"Okay. So let's note the mobile app for later, but it doesn't fit our current constraint. We're focused on deepening value to drive expansion."
The idea isn't dismissed. It's deferred. Big difference.
After 45 minutes of focused discussion, you decide: Build the analytics features (highest customer request volume, clearest ROI, most likely to drive upgrades).
Next Objective: "Define what 'analytics features' means in detail and scope the MVP."
You end the meeting with clarity, a decision, and a clear next step. No follow-up needed just to figure out what you were supposed to decide.
Total meeting time: One hour.
This is not hypothetical. I've run this exact meeting. Multiple times. The first time I used OBCT, I was shocked at how much faster we moved, and how much better people felt about the outcome.
Because everyone's concerns were heard. But they were evaluated against a common objective, not against each other's departmental goals.
Common Pitfalls (and How to Avoid Them)
I've been using this framework for a few years now, and I've seen the same mistakes come up over and over. Here are the big ones:
Pitfall #1: Setting Constraints Too Narrow
If your constraint is "We can only do X," you've killed the conversation before it starts. That's not a constraint, that's a foregone conclusion pretending to be a discussion.
Good constraints create a bounded space for exploration, not a single predetermined answer.
Fix: Frame constraints as "either/or" or "these are the paths available" rather than "this is the only option."
Pitfall #2: Skipping the Objective
This is the mistake we made at that offsite. Jumping straight into constraints without a clear objective means you're optimizing for the wrong thing, or for nothing at all.
Fix: Always start with "What are we trying to achieve?" and get explicit agreement before you move forward.
Pitfall #3: Treating Constraints as Permanent
Constraints should evolve as you learn. If the discussion reveals that your constraint is wrong, change it. Don't stubbornly stick to a framework when reality is telling you something different.
Fix: Use the constraint loop, check in regularly and ask if the current framing still makes sense.
Pitfall #4: Not Writing It Down
This seems small, but it's huge. If the objective and constraints aren't visible to everyone in the room, on a whiteboard, on a screen, in the shared notes, people will forget them. And you'll drift.
Fix: Write it down at the start. Keep it visible. Refer back to it.
Pitfall #5: Letting Departmental Goals Masquerade as Objectives
This is subtle but critical. Sometimes what sounds like an objective is actually just one person's departmental goal dressed up as a company objective.
"Increase sales pipeline by 40%" sounds like an objective, but it's really a Sales goal. "Launch three new features" sounds like an objective, but it's really a Product goal.
A real objective transcends departments. "Achieve $10M ARR by year-end" is an objective everyone can rally around, even if it requires different things from different teams.
Fix: Test your objective by asking: "Would every department in this room measure success the same way?" If not, keep refining.
What I Wish I'd Said at That Offsite
If I could go back to that conference room with the mountain view and the cold buffet lunch, here's what I would have done differently.
Before the CEO said "Let's talk about strategy," I would have stood up and said:
"Before we start, can we agree on three things?"
1. The objective for this offsite: "By the end of today, we will have identified two growth levers for next year, assigned owners, and defined success metrics."
2. Our first-order constraint: "We will focus on growth that leverages our existing capabilities and market position, not on entirely new markets or products."
3. How we'll know we succeeded: "We leave with two clear initiatives, documented owners, and a plan to check progress in 30 days."
Then I would have written those three things on the whiteboard in giant letters. And every time the conversation drifted, which it would have, because that's what conversations do, I would have pointed at the board and asked: "Does this align with our objective and constraint?"
And when Sales started pushing for more products and Finance started pushing for better margins and Product started defending the roadmap, I would have said: "All valid concerns. But our objective today is to identify growth levers, not to solve every problem. Let's evaluate each idea against that objective. If it doesn't fit, we'll note it for a future discussion."
We would have still gone out for that nice lunch. We would have still had the beautiful view.
But we wouldn't have left with pages of notes that went nowhere.
We would have left with a plan. And everyone would have been aligned on what we were trying to achieve, not because they all agreed on everything, but because they all agreed on what question we were answering.
The Bottom Line
The OBCT framework isn't magic. It's just structure, but structure is exactly what most strategic conversations lack.
By forcing yourself to answer two simple questions, What are we solving for? and What boundaries will we respect?. You turn vague discussions into focused decisions. You make meetings productive. You make progress visible. You stop confusing activity with achievement.
And you give people with different perspectives a common language to collaborate instead of compete.
Because the truth is, you need those different perspectives. You need Sales to tell you what customers are asking for. You need Finance to tell you what's financially viable. You need Product to tell you what's technically feasible. You need the CEO to tell you what aligns with the company's strategic direction.
But without an objective to unite them, those perspectives become sources of conflict instead of sources of insight.
The OBCT framework doesn't eliminate disagreement. It makes disagreement productive. It turns "Sales wants features and Finance wants margins" into "Given our objective of driving expansion revenue, which investment, features or margins, will get us there faster?"
Same people. Same perspectives. Completely different outcome.
And here's the best part: once you start using OBCT, you'll notice how many conversations around you are stuck because they're missing it. You'll see the drift, the circular arguments, the false consensus that leads nowhere. You'll watch hour-long meetings accomplish what could have taken fifteen minutes if anyone had just asked, "What's the objective here?"
You'll become the person who says, "Before we go further, what are we trying to achieve?"
And everyone in the room will breathe a sigh of relief, because finally, someone's steering the plane.
So here's my challenge to you: In your next important meeting, before anyone says anything else, write three things at the top of the agenda or on the whiteboard:
Objective:
First-Order Constraint:
Decision to Make:
Then see what happens.
I'm willing to bet you'll get more done in 30 minutes than you usually do in two hours.
Because once you know where you're going and which roads are available, the destination becomes inevitable.
And you'll never waste another offsite staring at the view while your strategy goes nowhere.
The Offsite That Went Nowhere
It was our annual strategic planning offsite, which, by title alone, implied gravitas. The kind of event where you book a nice hotel, order a buffet lunch that costs more than most people's weekly grocery bill, and convince yourself that being offsite somehow makes the thinking more strategic.
It didn't.
There were no clear objectives. No defined outcomes. Just the words "Annual Strategic Planning" sitting on the agenda like a promise of direction that never arrived, a placeholder for importance we hadn't actually earned.
We gathered in a conference room with a view, laptops open, caffeine flowing, notebooks pristine and ready to capture insights. We were going to "shape the future." The CEO kicked things off with enthusiasm and a confident smile: "Alright, let's talk about next year's strategy."
It didn’t take long before someone said it, the four words that derail more meetings than any others:
"I have an idea."
The idea wasn't bad. Actually, it was pretty good. It involved a partnership with a company that was gaining traction in our space, and it sounded plausible enough that nobody wanted to be the person to shoot it down immediately. Slides came out. Someone pulled up their financial model. Side conversations started about who would own the relationship. And suddenly we were knee-deep in pricing debates, hypothetical org charts, and "what if" scenarios about market positioning.
For twenty minutes, the room hummed with energy. People were engaged. We were doing strategy.
But here's what we weren't doing: answering any coherent question.
The idea stood alone, a shiny object that had hijacked the agenda. It wasn't connected to any declared objective. We hadn't defined what success looked like for the year, or for the meeting, or even for that conversation. We hadn't established whether we were trying to grow revenue, expand market share, enter new segments, or fix operational problems. We were just... talking about an idea because it seemed interesting.
After watching this unfold for long enough that the buffet lunch was getting cold, I finally asked the question that stopped the momentum like a record scratch:
"What's the objective of this meeting? What are we actually trying to achieve?"
Silence.
Then the nervous laughter that says, we probably should've figured that out beforehand.
The CEO looked at the agenda. Someone else looked at their laptop. A few people looked at me like I'd just asked why we breathe oxygen, something so obvious it shouldn't need to be said, yet nobody had an answer.
"Well," someone finally offered, "we're here to plan strategy for next year."
"Right," I said. "But what does that mean? Are we trying to decide between growth options? Identify our biggest risk? Commit to specific initiatives? All of the above? Something else?"
More silence. And that's when it hit me with uncomfortable clarity:
Most so-called strategy sessions fail not because people lack ideas, but because they lack objective-based constraints.
Everyone's rowing hard, but nobody's steering. We had smart people, good intentions, decent ideas, and a beautiful view. What we didn't have was structure.
An objective gives you a path to measure success. It lets you ask, at the end of the meeting, did we achieve what we set out to achieve, or did we just talk about interesting things?
A constraint defines where to focus, the edges of what matters, so the discussion stays useful instead of sprawling into every direction at once.
If our objective had been clear, "Identify two growth levers for next year and assign owners" and our constraint explicit, "Focus on expanding market share in our current market before considering new markets," we'd have known immediately what belonged in the discussion and what didn't.
That partnership idea? Maybe it fit. Maybe it didn't. But we couldn't evaluate it because we had no criteria for evaluation.
Instead, we left the offsite at 4 PM with pages of notes, scattered action items nobody would remember in a week, and no real decisions. It felt like progress because we'd been talking for six hours. It wasn't progress. It was just an expensive way to avoid making hard choices.
I drove home frustrated, and over the next few weeks, that frustration crystallized into something more useful: a framework.
Now, before any meeting begins, especially the important ones, I start with two questions:
What is the objective?
What are the constraints?
Because without those, even the best ideas are just noise. And even the most expensive offsite is just a scenic way to waste time.
Let me show you how this works.
The Hidden Problem: Everyone's Optimizing for Their Own Scoreboard
Before I dive into the framework, I need to address something that took me years to fully understand: why smart, well-intentioned people in the same company can spend hours in a room and make no progress.
It's not just that meetings lack structure. It's that every person at the table is optimizing for a different outcome, often without realizing it.
Think about who shows up to a strategic planning meeting:
Sales wants lower pricing, more features, more products, faster delivery, and whatever else will help them close deals this quarter.
Product wants time to build things right, fewer feature requests, and the freedom to focus on technical debt and user experience.
Finance wants predictable revenue, better margins, and cost control.
Marketing wants budget, creative freedom, and lead generation targets that are actually achievable.
The C-suite wants growth, profitability, market position, and something impressive to tell the board.
Here's the thing: none of these perspectives are wrong. In fact, having different viewpoints at a meeting is often valuable, it's how you spot blind spots, challenge assumptions, and avoid groupthink.
But it's also a massive source of unproductive conflict.
At that offsite I described, when we started discussing the partnership idea, here's what was actually happening under the surface:
The VP of Sales loved it because it would give them a new product to sell and access to the partner's customer base.
The CFO was skeptical because partnerships are notoriously hard to forecast and don't always generate the revenue you think they will.
The Head of Product was worried it would distract from the roadmap and create technical dependencies.
The CEO liked the optics of announcing a high-profile partnership but wasn't sure if it was the highest leverage move.
So we spent a long time debating, but we weren't really debating the same question. Sales was debating "will this help me hit quota?" Finance was debating "will this be profitable?" Product was debating "will this derail our existing plans?" And the CEO was debating "is this the best use of our limited resources?"
Without a clear objective, every person was scoring the idea against their own department's goals, not the company's goals.
This is why meetings spiral. This is why the same arguments happen over and over. This is why you leave feeling like "we just can't get aligned."
It's not that alignment is impossible. It's that you're trying to align people who are playing different games on different fields with different rules.
An objective fixes this. It doesn't eliminate different perspectives, you still want those. But it gives everyone a common scoreboard.
If the objective is "Identify the initiative that will generate the most expansion revenue from existing customers in the next six months," then suddenly:
Sales can't just argue for "more products" without showing how it drives expansion revenue.
Product can't just defend the current roadmap without proving it solves the expansion problem.
Finance can't just focus on margins without acknowledging that expansion revenue is the priority.
The CEO has a clear tiebreaker when opinions conflict.
The objective keeps everyone on the same page, not because it eliminates disagreement, but because it makes the disagreement productive.
You're no longer arguing about whether the idea is good in general. You're arguing about whether it achieves this specific objective. And that's a much more solvable problem.
This was the missing piece at that offsite. We had all the right people in the room, and they all had valid concerns. But we were having five different conversations at once, and none of them were moving us toward a decision.
Now let me show you how the framework I built prevents that from happening.
The Framework I Built From That Failure
What I developed after that disastrous offsite is something I call Objective-Based Constrained Thinking, OBCT for short. It's not complicated. In fact, that's the point. It's a simple, layered approach that transforms vague conversations into structured decisions.
The core idea is this: before you discuss anything, define what you're solving for (your objective) and what boundaries you'll respect (your constraints), in layers that evolve as clarity increases.
Think of it as GPS for meetings. You need a destination, and you need to know which roads are actually available. Without both, you're just driving in circles and burning gas.
Here's how it works, step by step.
Step 1: Declare the Objective
The Question: What are we trying to achieve in this discussion or decision?
This sounds obvious, but as I learned in that conference room with the view, most meetings skip it entirely. They have a topic ("Q4 Planning" or "Product Roadmap" or "Annual Strategic Planning"), but not an objective, a specific outcome they're trying to reach.
Here's the difference:
Topic: "Let's discuss growth."
Objective: "Determine which growth lever to prioritize next quarter."
See how the second one changes everything? It tells you what success looks like. It tells you when you're done. It tells you what kinds of conversations are productive and which ones are distractions.
And critically, it aligns everyone's individual perspectives toward a common goal.
When your VP of Sales walks into a meeting about "growth" without an objective, they're thinking about quota and pipeline. When your CFO walks in, they're thinking about profitability and cash flow. When your Head of Product walks in, they're thinking about roadmap capacity and technical feasibility.
All valid concerns. But they're not the same concern.
When you declare the objective as "Determine which growth lever will generate the most expansion revenue from existing customers in Q1," suddenly everyone knows what game they're playing. Sales can't just advocate for "more leads" if leads don't drive expansion. Finance can't just focus on cutting costs if the goal is expansion revenue. Product can't just protect the roadmap without showing how it drives the objective.
The objective doesn't silence different viewpoints, it channels them toward a common destination.
If I could go back to that offsite, I would have written on the whiteboard before anyone said a word:
Objective: Identify and commit to two specific growth initiatives for next year, with assigned owners and success metrics.
That one sentence would have saved us hours, and would have prevented the Sales team from advocating for "more products" and the CFO from arguing for "better margins" when neither was actually the question we needed to answer.
How to Write a Good Objective
A well-formed objective is:
Specific: Not "improve the product," but "define the core problem our new product feature is solving."
Actionable: It points toward a decision, not just awareness or discussion.
Scoped: It's achievable in the time you've allocated.
Unifying: It gives everyone a common scoreboard to evaluate ideas against.
More examples:
Bad: "Talk about customer retention"
Good: "Decide whether to invest in customer success headcount or automated onboarding for Q1"
Bad: "Review marketing performance"
Good: "Identify the top-performing channel and commit to a 6-month doubling-down strategy"
So now, before any meeting I run starts, I write the objective at the top of the agenda. I say it out loud. I make sure everyone agrees on it. And if they don't? We figure that out before we waste an hour going in different directions.
Because when everyone's rowing toward the same destination, different perspectives become strengths instead of sources of conflict.
Step 2: Establish the First-Order Constraint
The Question: What boundaries define success?
Once you know what you're trying to achieve, you need to narrow the field. This is where constraints come in, and I know "constraint" sounds limiting, but that's exactly the point. Constraints aren't creativity killers; they're focus enablers.
Let's say your objective is: "Grow the business next year."
That's a start, but it's still too open-ended. Growth could mean a thousand things. So you establish a first-order constraint, a strategic lens that filters your options.
Example First-Order Constraints:
Option A: Grow market share (win more customers in your current market)
Option B: Broaden addressable market (enter new segments or geographies)
Option C: Both, if we can prove we have the capacity and differentiation to execute on two fronts
Notice what just happened. You went from "infinite possibilities" to "three paths." That's the power of a well-chosen constraint.
At that offsite I told you about? We never established this. So when someone proposed that partnership idea, we had no way to evaluate it. Did it help us grow market share? Expand to new markets? Improve retention? We didn't know, because we hadn't decided what we were optimizing for.
And because we hadn't set a constraint, each person evaluated the idea through their own lens:
Sales thought: "Will this give me more things to sell?"
Product thought: "Will this distract from my roadmap?"
Finance thought: "Will this be profitable?"
The CEO thought: "Will this look good?"
All reasonable questions. But they weren't the same question, so we couldn't reach a conclusion.
Now, when someone proposes an idea in one of my meetings, I can ask: "Does this help us grow market share, or expand our addressable market, or both?" If the answer is "neither," we table it. If it's "one of them," we evaluate it against that constraint. If it's "both," we dig deeper to see if it's realistic.
This eliminates vague brainstorming and anchors the group in bounded exploration.
You're not shutting down creativity, you're channeling it. Think of it like a river: unbounded water spreads into a swamp, but water within banks becomes a powerful current.
Step 3: Apply Second-Order Constraints
The Question: Within those boundaries, what specific paths exist?
This is where you zoom in. First-order constraints set the strategic direction. Second-order constraints define the tactical options within that direction.
Let's continue the example. You've decided your first-order constraint is "Grow market share" (win more customers in your current market).
Great. Now you need to get specific. How do you actually do that? Your second-order constraints might include:
Complete market "must-haves" — Add the table-stakes features your competitors have that you're missing (you're losing deals because of gaps).
Add or reinforce differentiators — Double down on what makes you unique (you're winning deals, but not enough people know about you).
Improve customer retention — Keep the customers you have (churn is killing your growth before it starts).
Each of these is a valid path, but they require different resources, timelines, and risks. By laying them out as explicit constraints, you force the team to choose, or at least to acknowledge the trade-offs.
Why This Matters
Without second-order constraints, you get analysis paralysis. Everyone agrees on the destination (grow market share), but no one can agree on the route. Some people want to build features. Others want to fix retention. Others want to invest in brand.
All of those might be good ideas, but you can't do everything at once, especially not if you're a startup or a growing company with limited resources. Second-order constraints force prioritization by making the options explicit and comparable.
Each layer defines the next set of valid conversations and automatically filters out noise.
When I think back to that offsite, we debated whether to hire more salespeople or invest in marketing automation. Both reasonable ideas (but not strategic). But we never established whether our constraint was "acquire more customers" or "convert more leads" or "retain existing customers longer." Without that context, we were comparing apples to oranges to airplanes.
And of course, Sales advocated for more headcount (because that's what helps Sales hit quota), while Finance advocated for automation (because that's what helps Finance hit margin targets). Neither was wrong. But neither was answering the right question, because we hadn't defined what the right question was.
Step 4: Navigate Using Constraint Loops
Here's where the framework becomes a living tool, not just a planning exercise.
Meetings drift. It's human nature. Someone raises an interesting tangent, and before you know it, you're debating office perks when you were supposed to be deciding on a product roadmap. (Yes, this has happened to me. More than once.)
The OBCT loop is your guardrail. When the conversation drifts, pause and ask:
"Does this align with our current objective and constraint set?"
If yes, continue. If no, you have two options:
Note it for later — "Great point, but let's table it for now and come back to it after we close this decision."
Redefine the constraint — "This discussion is revealing that our constraint might be wrong. Should we adjust?"
Why Constraints Evolve
Here's the key insight that took me a while to learn: Constraints aren't cages; they're focus tools that evolve with understanding.
Sometimes, the act of exploring within a constraint reveals that the constraint itself was too narrow or aimed at the wrong thing. That's fine. The framework gives you permission to adjust, but it forces you to do so consciously, not accidentally.
For example, you might start with "grow market share" and realize mid-discussion that your real bottleneck is retention, not acquisition. Customer acquisition is actually going great, they're just churning out the back door. At that point, you explicitly reframe: "It sounds like we need to shift our first-order constraint from growth to retention. Does everyone agree?"
Now you're not drifting, you're pivoting with intention. There's a huge difference.
At that offsite, we drifted from partnerships to pricing to org structure to marketing messaging without ever acknowledging we'd changed topics. If we'd been using the OBCT loop, someone could have said, "Hold on, we're now talking about pricing, but our objective was about growth levers. Is pricing a lever we want to evaluate, or are we off track?"
That one question would have saved us.
Step 5: End With Convergence
This is the step most meetings skip, and it's the reason nothing ever gets done.
I've been in so many meetings that end with "Great discussion, let's pick this up next time," and then next time, we start from scratch because nobody remembers what we decided or why.
Every OBCT discussion should end with three things clearly stated and written down:
1. Restated Objective
Did we achieve it? Did we need to reframe it?
"We set out to determine which growth lever to prioritize. We decided it's customer retention through improved onboarding."
2. Final Constraint Set
What's the next boundary for action?
"Our second-order constraints are: (1) automate the first 48 hours of user experience, (2) launch a customer success check-in at day 30."
3. Next Objective
What comes after this decision?
"Next meeting: Define success metrics for the new onboarding flow and assign owners."
That way, each meeting hands the next one a clear runway, no re-hashing, no fog.
You're not just ending the meeting, you're launching the next one. And the next one. And the next one. Each with clarity, each with momentum.
That offsite I mentioned? We left with action items like "explore partnership opportunities" and "think about market expansion." Which is a fancy way of saying we left with homework but no decisions.
If we'd ended with convergence, we would have left with: "We've decided to focus on growing market share before expanding markets. Our next objective is to choose between completing must-have features or improving retention. That decision will be made in two weeks after we review customer churn data."
See the difference?
Why This Framework Works: The Psychology of Bounded Exploration
There's a reason the OBCT framework feels so effective once you start using it: it aligns with how our brains actually make decisions.
Cognitive research shows that humans struggle with unbounded choice. Give someone infinite options, and they freeze. Give them three clear paths, and they can evaluate, compare, and decide. This is why restaurants with 100-item menus are stressful, but prix fixe menus feel luxurious. This is why "let's discuss strategy" makes people anxious, but "choose between option A and option B" makes them feel productive.
OBCT does the same thing for strategic thinking. It doesn't limit creativity, it channels it. It says: "Here's the sandbox. Build anything you want inside it, and if you need a bigger sandbox, we'll talk about that too."
This has a second-order effect that I didn't expect when I first started using the framework: it makes meetings psychologically safer.
When everyone knows what's in scope and what's not, people feel more comfortable contributing. They're not worried about being off-topic or wasting time. They know their idea will either fit within the current constraint (and be evaluated fairly) or get noted for a future discussion. Nobody's idea gets dismissed as "not strategic" without context, it either fits the current objective or it gets its own objective later.
I've noticed that quieter people speak up more in OBCT meetings. Because the structure protects them from being steamrolled by the loudest voice in the room.
And crucially, the framework neutralizes departmental politics.
When Sales pushes for lower pricing or more features, you don't have to argue about whether that's "the right thing to do" in some abstract sense. You just ask: "Does this achieve our stated objective?" If yes, evaluate it. If no, defer it. The objective becomes the referee, not the highest-paid person in the room.
Putting OBCT Into Practice: A Real-World Example
Let me walk you through how this might play out in a real meeting, because I want you to see the contrast between the old way and the new way.
Context: You're a startup planning your product roadmap for the next six months.
Before OBCT (The Old Way):
The meeting starts with "Let's talk about the roadmap." Two hours later, you've debated:
Whether to build a mobile app
Whether to add enterprise features
Whether to redesign the UI
Whether to focus on performance improvements
Whether to integrate with third-party tools
Someone mentions AI because, well, everyone's talking about AI. Someone else brings up a competitor feature. The designer wants to fix the onboarding flow. The engineer wants to refactor the backend.
All valid points. All interesting. None of them clearly more important than the others.
And here's what's happening under the surface:
Sales is pushing for enterprise features because they keep losing deals to competitors who have them
Product is pushing for the UI redesign because they're embarrassed by the current interface
Engineering is pushing for the refactor because the code is becoming unmaintainable
The CEO is pushing for AI features because that's what investors want to hear about
Everyone has a legitimate concern. Everyone's advocating for what makes sense from their seat. And because there's no objective, everyone's pitching ideas that optimize for their own success metrics.
No decision is made. Everyone's frustrated. You schedule a follow-up meeting to "narrow things down." Which will take another two hours and probably also end without a decision.
With OBCT (The New Way):
You start the meeting by writing on the whiteboard:
Objective: "Decide which product direction will most directly impact revenue in the next six months."
Everyone agrees on the objective. Already you've saved fifteen minutes of "wait, what are we doing here?" And more importantly, you've given Sales, Product, Engineering, and the CEO a common scoreboard.
Now when Sales pitches enterprise features, they can't just say "we need these to win deals." They have to show how those features will impact revenue in six months. When Product pitches the UI redesign, they have to connect it to revenue. When Engineering pitches the refactor, same thing.
First-Order Constraint: "We can either (A) deepen value for existing customers to drive expansion revenue, or (B) add features to win new customer segments."
The team discusses both paths. You look at your data. Your sales pipeline is healthy, you're signing new customers at a decent clip. But your expansion revenue is flat. Customers sign on, use the basic tier, and stay there. You're not moving them up-market.
You choose: "Deepen value for existing customers."
Now you're not debating mobile apps vs. enterprise features in a vacuum. You're asking: which one deepens value for existing customers?
Second-Order Constraints: Within that, you have three options:
Add integrations that make the product stickier
Build analytics features that customers are asking for
Improve onboarding so customers reach value faster
Someone proposes the mobile app. You ask: "Does this deepen value for existing customers?"
"Well," they say, "it would make it easier to use the product on the go."
"True," you say, "but is that why expansion revenue is flat? Or is it because customers don't see enough value in the advanced features to upgrade?"
Pause. "Probably the second one."
"Okay. So let's note the mobile app for later, but it doesn't fit our current constraint. We're focused on deepening value to drive expansion."
The idea isn't dismissed. It's deferred. Big difference.
After 45 minutes of focused discussion, you decide: Build the analytics features (highest customer request volume, clearest ROI, most likely to drive upgrades).
Next Objective: "Define what 'analytics features' means in detail and scope the MVP."
You end the meeting with clarity, a decision, and a clear next step. No follow-up needed just to figure out what you were supposed to decide.
Total meeting time: One hour.
This is not hypothetical. I've run this exact meeting. Multiple times. The first time I used OBCT, I was shocked at how much faster we moved, and how much better people felt about the outcome.
Because everyone's concerns were heard. But they were evaluated against a common objective, not against each other's departmental goals.
Common Pitfalls (and How to Avoid Them)
I've been using this framework for a few years now, and I've seen the same mistakes come up over and over. Here are the big ones:
Pitfall #1: Setting Constraints Too Narrow
If your constraint is "We can only do X," you've killed the conversation before it starts. That's not a constraint, that's a foregone conclusion pretending to be a discussion.
Good constraints create a bounded space for exploration, not a single predetermined answer.
Fix: Frame constraints as "either/or" or "these are the paths available" rather than "this is the only option."
Pitfall #2: Skipping the Objective
This is the mistake we made at that offsite. Jumping straight into constraints without a clear objective means you're optimizing for the wrong thing, or for nothing at all.
Fix: Always start with "What are we trying to achieve?" and get explicit agreement before you move forward.
Pitfall #3: Treating Constraints as Permanent
Constraints should evolve as you learn. If the discussion reveals that your constraint is wrong, change it. Don't stubbornly stick to a framework when reality is telling you something different.
Fix: Use the constraint loop, check in regularly and ask if the current framing still makes sense.
Pitfall #4: Not Writing It Down
This seems small, but it's huge. If the objective and constraints aren't visible to everyone in the room, on a whiteboard, on a screen, in the shared notes, people will forget them. And you'll drift.
Fix: Write it down at the start. Keep it visible. Refer back to it.
Pitfall #5: Letting Departmental Goals Masquerade as Objectives
This is subtle but critical. Sometimes what sounds like an objective is actually just one person's departmental goal dressed up as a company objective.
"Increase sales pipeline by 40%" sounds like an objective, but it's really a Sales goal. "Launch three new features" sounds like an objective, but it's really a Product goal.
A real objective transcends departments. "Achieve $10M ARR by year-end" is an objective everyone can rally around, even if it requires different things from different teams.
Fix: Test your objective by asking: "Would every department in this room measure success the same way?" If not, keep refining.
What I Wish I'd Said at That Offsite
If I could go back to that conference room with the mountain view and the cold buffet lunch, here's what I would have done differently.
Before the CEO said "Let's talk about strategy," I would have stood up and said:
"Before we start, can we agree on three things?"
1. The objective for this offsite: "By the end of today, we will have identified two growth levers for next year, assigned owners, and defined success metrics."
2. Our first-order constraint: "We will focus on growth that leverages our existing capabilities and market position, not on entirely new markets or products."
3. How we'll know we succeeded: "We leave with two clear initiatives, documented owners, and a plan to check progress in 30 days."
Then I would have written those three things on the whiteboard in giant letters. And every time the conversation drifted, which it would have, because that's what conversations do, I would have pointed at the board and asked: "Does this align with our objective and constraint?"
And when Sales started pushing for more products and Finance started pushing for better margins and Product started defending the roadmap, I would have said: "All valid concerns. But our objective today is to identify growth levers, not to solve every problem. Let's evaluate each idea against that objective. If it doesn't fit, we'll note it for a future discussion."
We would have still gone out for that nice lunch. We would have still had the beautiful view.
But we wouldn't have left with pages of notes that went nowhere.
We would have left with a plan. And everyone would have been aligned on what we were trying to achieve, not because they all agreed on everything, but because they all agreed on what question we were answering.
The Bottom Line
The OBCT framework isn't magic. It's just structure, but structure is exactly what most strategic conversations lack.
By forcing yourself to answer two simple questions, What are we solving for? and What boundaries will we respect?. You turn vague discussions into focused decisions. You make meetings productive. You make progress visible. You stop confusing activity with achievement.
And you give people with different perspectives a common language to collaborate instead of compete.
Because the truth is, you need those different perspectives. You need Sales to tell you what customers are asking for. You need Finance to tell you what's financially viable. You need Product to tell you what's technically feasible. You need the CEO to tell you what aligns with the company's strategic direction.
But without an objective to unite them, those perspectives become sources of conflict instead of sources of insight.
The OBCT framework doesn't eliminate disagreement. It makes disagreement productive. It turns "Sales wants features and Finance wants margins" into "Given our objective of driving expansion revenue, which investment, features or margins, will get us there faster?"
Same people. Same perspectives. Completely different outcome.
And here's the best part: once you start using OBCT, you'll notice how many conversations around you are stuck because they're missing it. You'll see the drift, the circular arguments, the false consensus that leads nowhere. You'll watch hour-long meetings accomplish what could have taken fifteen minutes if anyone had just asked, "What's the objective here?"
You'll become the person who says, "Before we go further, what are we trying to achieve?"
And everyone in the room will breathe a sigh of relief, because finally, someone's steering the plane.
So here's my challenge to you: In your next important meeting, before anyone says anything else, write three things at the top of the agenda or on the whiteboard:
Objective:
First-Order Constraint:
Decision to Make:
Then see what happens.
I'm willing to bet you'll get more done in 30 minutes than you usually do in two hours.
Because once you know where you're going and which roads are available, the destination becomes inevitable.
And you'll never waste another offsite staring at the view while your strategy goes nowhere.
Oct 21, 2025
The Five Things You Actually Need to Run a Business, and the Two That Make You Win
You can run on five, you win on two. Five fundamentals keep the lights on, two ways of thinking compound value for years.
Oct 16, 2025
Stop Wasting Time in Meetings: The Framework I Wish I'd Had at That Disastrous Offsite
Most so-called strategy sessions fail not because people lack ideas, but because they lack objective-based constraints.
Oct 14, 2025
The Great AI Hallucination Misunderstanding: Why LinkedIn's Loudest Critics Are Missing the Point
Every day on LinkedIn, another post surfaces with the same tired revelation: "ChatGPT made up citations!" or "AI hallucinated facts!" These posts, dressed up as serious analysis, are really just intellectual laziness disguised as skepticism.
Oct 21, 2025
The Five Things You Actually Need to Run a Business, and the Two That Make You Win
You can run on five, you win on two. Five fundamentals keep the lights on, two ways of thinking compound value for years.
Oct 16, 2025
Stop Wasting Time in Meetings: The Framework I Wish I'd Had at That Disastrous Offsite
Most so-called strategy sessions fail not because people lack ideas, but because they lack objective-based constraints.
Oct 21, 2025
The Five Things You Actually Need to Run a Business, and the Two That Make You Win
You can run on five, you win on two. Five fundamentals keep the lights on, two ways of thinking compound value for years.
NeWTHISTle Consulting
DELIVERING CLARITY FROM COMPLEXITY
Copyright © 2025 NewThistle Consulting LLC. All Rights Reserved
NeWTHISTle Consulting
DELIVERING CLARITY FROM COMPLEXITY
Copyright © 2025 NewThistle Consulting LLC. All Rights Reserved
NeWTHISTle Consulting
DELIVERING CLARITY FROM COMPLEXITY
Copyright © 2025 NewThistle Consulting LLC. All Rights Reserved