Category: Strategy
Oct 9, 2025
The Most Powerful Question Leaders Refuse to Ask
"What if?"
Two simple words. Barely a sentence. Yet in my years working both as an air traffic controller and as a CEO, I've come to realize that this might be the most underused, and most powerful, question in business.
Not "What's our quarterly target?" Not "How do we optimize current operations?" Not even "What's working right now?"
But rather: "What if we're completely wrong about everything?"
The Comfort of Certainty (And Why It's Killing Your Business)
Many leaders avoid the "what if" question like the plague.
And I get it. I really do.
When you're steering a company, managing stakeholders, and responsible for people's livelihoods, uncertainty feels like weakness. Confidence feels like leadership. Admitting you might need to pivot, that your current strategy might be built on shifting sand, that feels dangerous.
But you know what's more dangerous? Being so committed to being right that you never prepare for being wrong.
"What if we're wrong?"
"What if the market shifts faster than we expect?"
"What if the next wave of AI isn't hype, but the new baseline?"
These questions don't make you a pessimist. They make you a realist. They make you the kind of leader who survives the storms that sink everyone else.
The Success Trap: When "Good Enough" Becomes Dangerous
Here's the paradox that kills companies: You're most likely to ignore "what if" questions when your business is doing well.
And that's exactly when they matter most.
Think about it. When revenue is up, customers are happy, and the board is pleased, who wants to be the person asking "But what if this all falls apart?"
When you're winning, questioning your strategy feels like self-sabotage. Why fix what isn't broken? Why risk disrupting a good thing? Why create problems where none exist?
I've seen it happen over and over. A company hits its stride. Growth becomes predictable. Processes get optimized. Everyone settles into a comfortable rhythm. And slowly, almost imperceptibly, the organization stops asking hard questions.
Success breeds complacency. And complacency breeds blindness.
When you're doing well, you start attributing your success to brilliance rather than circumstance. You assume your strategy is sound because the results are good. You mistake current performance for future immunity.
But here's what history teaches us: The companies that fail catastrophically rarely see it coming. And when we look back, the warning signs were always there. The market was shifting. Technology was evolving. Customer preferences were changing. Competitors were innovating.
The difference between the companies that survived and those that didn't wasn't information, it was willingness to question success while they still had it.
Blockbuster was profitable when Netflix was just a DVD-by-mail service. Nokia dominated the mobile market when the iPhone launched. Kodak invented the digital camera but couldn't imagine abandoning film. Yep all stories you have heard, but have you considered these examples in your own planning?
They weren't failing when they needed to ask "what if." They were succeeding. And that's precisely why they didn't ask.
Here's what every leader needs to internalize: Financial results are a report card, not a prediction.
Your quarterly earnings tell you how well you executed yesterday's strategy in yesterday's market. They don't tell you whether tomorrow's strategy will work in tomorrow's market.
By the time your financial results turn down, the game has already changed. The customers have already started shifting. The technology has already advanced. The competitor has already gained ground.
If you wait for your numbers to decline before you make a change, it's already too late.
You're not being proactive, you're being reactive. And in a reactive mode, you're not choosing your future; you're desperately trying to salvage your past.
The most dangerous time to stop asking "what if" is when you think you don't need to.
When business is good, "what if" feels like pessimism. But it's not. It's insurance. It's the difference between being proactive and being caught off-guard.
Your competitors aren't resting because you're winning. Markets aren't pausing because your quarter was strong. Technology isn't waiting because you're comfortable.
So if you're reading this and thinking, "Well, things are pretty good right now, maybe I'll worry about this later," that's your answer. That's exactly why you need to ask "what if" today.
The AI Question Nobody Wants to Answer
Let's talk about the elephant in the room, artificial intelligence.
I've watched countless executives treat AI like it's just another tech trend. "We'll wait and see," they say. "Let's not overreact to the hype," they caution. "We need more data before we invest."
But here's the "what if" that should keep you up at night:
What if you're wrong about AI?
What if it isn't a bubble waiting to burst? What if it's not like blockchain or the metaverse or any of the other buzzwords that came and went?
What if AI is the next infrastructure layer of business itself?
Think about that for a moment. Not a tool. Not a feature. Not a nice-to-have. But infrastructure, as fundamental as electricity, the internet, or mobile computing.
What if, in five years, not using AI in your business is like trying to run a company today without email or a website? What if the question isn't "Should we adopt AI?" but rather "How far behind are we already?"
And the really uncomfortable part: What if your competitors are quietly figuring out how to use it right now, while you're still "waiting to see"?
They're not announcing it in press releases. They're not bragging about it on LinkedIn. They're just... doing it. Building it into their operations. Training their teams. Finding the edges that will become competitive moats.
And you? You're gathering more data. Waiting for the perfect moment. Telling yourself you're being prudent.
From 30,000 Feet to the Corner Office: What Air Traffic Control Taught Me About Management
Before I became a CEO, I spent years as an air traffic controller. And if there's one profession that forces you to embrace "what if" thinking, it's that one.
In air traffic control, reactive thinking isn't just bad management, it's catastrophic. By the time you're reacting to a problem, it's already too late. The planes are already too close. The weather has already turned. The system has already failed.
The entire profession is built on one principle: anticipate, don't react.
"What if this flight has an emergency?" "What if the weather deteriorates faster than forecasted?" "What if two planes end up converging on the same point?"
We didn't ask these questions because we were paranoid. We asked them because we were professionals. Because preparation isn't paranoia, it's responsibility.
And yet, when I transitioned into corporate leadership, I was shocked by how many executives operate in purely reactive mode.
They wait for the market to shift, then scramble to respond. They wait for competitors to innovate, then rush to catch up. They wait for technology to mature, then panic when they're years behind.
Reactive management is a path to failure. In air traffic control, we knew that. But in business? Somehow it's become the norm.
The Anatomy of a Better "What If"
Not all "what if" questions are created equal. Some are productive. Others are just anxiety dressed up as strategy.
Here's how to ask better "what if" questions:
1. Make Them Specific
Bad: "What if things change?" Good: "What if our largest customer moves 50% of their business to a competitor who offers solutions because of capabilities only made possible by, in the next 18 months?"
The more specific your "what if," the more actionable your response can be.
2. Attach Them to Signals
Bad: "What if AI takes over everything?" Good: "What if our customer support tickets that could be handled by AI reach 70%? What does that mean for our team structure?"
Look for concrete signals you can monitor. What metrics would tell you the "what if" is becoming reality?
3. Build Plan B Before You Need It
The point of "what if" isn't to predict the future perfectly. It's to have a Plan B ready before the world hands you a Plan C you didn't choose.
When you ask "What if AI capabilities becomes table stakes in our industry?", the next question isn't "Will it happen?" It's "What would we do if it does?"
Then you start preparing. Not committing. Not betting the farm. Just... preparing.
Maybe that means:
Identifying one workflow where AI could be tested
Training a small team on emerging tools
Allocating 5% of your innovation budget to experimentation
Building relationships with AI vendors before you desperately need them
4. Separate Exploration from Commitment
One reason leaders avoid "what if" thinking is they conflate asking the question with making a decision.
They think: "If I ask 'what if AI matters,' then I have to immediately invest millions in AI."
No. You don't.
Asking "what if" creates options. It doesn't force choices. It expands your decision tree so that when the moment comes to decide, you're not starting from zero.
The Questions You Should Be Asking Right Now
Let me give you some "what ifs" that are worth your time in 2025:
About Technology:
What if AI reduces the cost of knowledge work by 80% in the next three years?
What if our customers expect AI-level service speed from all vendors?
What if our product becomes a feature of someone else's AI platform?
About Markets:
What if our core customer demographic shifts their buying behavior faster than our sales cycle can adapt?
What if remote work becomes so accepted that geography becomes irrelevant for talent, making us compete globally for every hire?
What if the economic assumptions we've built our growth model on completely reverse?
About Competition:
What if a well-funded startup enters our space with AI-native operations and 1/10th our cost structure?
What if our biggest competitor isn't another company in our industry, but a platform that makes our service obsolete?
What if the barriers to entry in our market collapse due to new technology?
About Your Organization:
What if our top performers leave because we're not innovating fast enough?
What if the skills we're hiring for today are irrelevant in 24 months?
What if our company culture, built for stability, becomes a liability in a period of rapid change?
These aren't doomsday scenarios. They're strategic considerations. And the difference between a company that thrives and one that merely survives is often just this: which questions did they ask before they were forced to?
From "What If" to "Now What": Building a Proactive Organization
So how do you actually build a culture of proactive "what if" thinking?
Create Permission to Question
First, you have to make it safe for people to ask uncomfortable questions. In most organizations, the person who asks "What if we're wrong about our core strategy?" gets labeled a troublemaker, not a truth-teller.
Change that.
Make "what if" sessions a regular part of your strategic planning. Not just quick brainstorms, but structured time where the goal is to challenge assumptions, not defend them.
Assign "What If" Ownership
Have someone on your leadership team whose explicit job is to play devil's advocate. Not to be negative, but to constantly ask: "What are we not seeing? What could go wrong? What opportunities might we be missing?"
In military planning, they call this "red teaming." In business, we just call it good management.
Build Scenario Plans
Don't just ask "what if, map out what you'd actually do if it happened.
If AI becomes critical infrastructure in your industry, what's your 90-day response plan? Your 1-year plan? Your 3-year plan?
Having these scenarios ready doesn't mean you execute them immediately. It means that when the world shifts, you're not starting from scratch.
Monitor, Don't Just Predict
Finally, set up your early warning system. What metrics would tell you that one of your "what if" scenarios is starting to come true?
Maybe it's:
Customer support ticket volume that could be automated
Competitor announcements in AI
Changes in time-to-hire for key roles
Shifts in customer inquiry topics
The goal isn't to predict the future perfectly. It's to notice change early enough to respond deliberately instead of desperately.
The Cost of Not Asking
Here's what happens when you don't ask "what if":
Someone else does. And they prepare. And when the market shifts, they're ready and you're not.
You end up asking "now what?" instead of "what if?"
And the difference between those two questions is the difference between proactive strategy and reactive panic.
"What if" gives you options. "Now what?" leaves you scrambling.
"What if" is asked in boardrooms with time to think. "Now what?" is asked in emergency meetings at 11 PM.
"What if" is leadership. "Now what?" is crisis management.
The Question That Changes Everything
So let me leave you with this:
What if the thing you're most confident about is the thing you should be questioning most?
What if your core product, your go-to-market strategy, your operational model, or your competitive moat isn't as solid as you think?
What if the reason you haven't disrupted yourself is because you're too comfortable with who you are to imagine who you might need to become?
What if the next three years don't look anything like the last three?
You can dismiss these as paranoid. You can file them away as "good questions for later."
Or you can start asking them now, while you still have time to prepare instead of time to panic.
Start Today
Here's your homework:
Block 90 minutes on your calendar this week. Label it "What If Strategy Session."
Bring your leadership team. No laptops. No phones. Just thinking.
Ask the uncomfortable questions:
What if we're wrong about AI?
What if our market changes faster than we can?
What if our biggest advantage becomes irrelevant?
For each "what if," outline:
What signals would tell us it's happening?
What would our response be?
What can we do now to prepare?
Choose one scenario. Just one. And take one small action this month to prepare for it.
That's it. You don't have to solve everything. You just have to start asking better questions.
Because the most expensive words in business aren't "what if."
They're "I wish we had."
The choice is yours: Keep waiting for certainty in an uncertain world, or start asking "what if" while you still have time to do something about the answers.
After years in the tower and years in the corner office, I can tell you with absolute certainty: the leaders who thrive aren't the ones with all the answers.
They're the ones asking the right questions.
What if you started today?
"What if?"
Two simple words. Barely a sentence. Yet in my years working both as an air traffic controller and as a CEO, I've come to realize that this might be the most underused, and most powerful, question in business.
Not "What's our quarterly target?" Not "How do we optimize current operations?" Not even "What's working right now?"
But rather: "What if we're completely wrong about everything?"
The Comfort of Certainty (And Why It's Killing Your Business)
Many leaders avoid the "what if" question like the plague.
And I get it. I really do.
When you're steering a company, managing stakeholders, and responsible for people's livelihoods, uncertainty feels like weakness. Confidence feels like leadership. Admitting you might need to pivot, that your current strategy might be built on shifting sand, that feels dangerous.
But you know what's more dangerous? Being so committed to being right that you never prepare for being wrong.
"What if we're wrong?"
"What if the market shifts faster than we expect?"
"What if the next wave of AI isn't hype, but the new baseline?"
These questions don't make you a pessimist. They make you a realist. They make you the kind of leader who survives the storms that sink everyone else.
The Success Trap: When "Good Enough" Becomes Dangerous
Here's the paradox that kills companies: You're most likely to ignore "what if" questions when your business is doing well.
And that's exactly when they matter most.
Think about it. When revenue is up, customers are happy, and the board is pleased, who wants to be the person asking "But what if this all falls apart?"
When you're winning, questioning your strategy feels like self-sabotage. Why fix what isn't broken? Why risk disrupting a good thing? Why create problems where none exist?
I've seen it happen over and over. A company hits its stride. Growth becomes predictable. Processes get optimized. Everyone settles into a comfortable rhythm. And slowly, almost imperceptibly, the organization stops asking hard questions.
Success breeds complacency. And complacency breeds blindness.
When you're doing well, you start attributing your success to brilliance rather than circumstance. You assume your strategy is sound because the results are good. You mistake current performance for future immunity.
But here's what history teaches us: The companies that fail catastrophically rarely see it coming. And when we look back, the warning signs were always there. The market was shifting. Technology was evolving. Customer preferences were changing. Competitors were innovating.
The difference between the companies that survived and those that didn't wasn't information, it was willingness to question success while they still had it.
Blockbuster was profitable when Netflix was just a DVD-by-mail service. Nokia dominated the mobile market when the iPhone launched. Kodak invented the digital camera but couldn't imagine abandoning film. Yep all stories you have heard, but have you considered these examples in your own planning?
They weren't failing when they needed to ask "what if." They were succeeding. And that's precisely why they didn't ask.
Here's what every leader needs to internalize: Financial results are a report card, not a prediction.
Your quarterly earnings tell you how well you executed yesterday's strategy in yesterday's market. They don't tell you whether tomorrow's strategy will work in tomorrow's market.
By the time your financial results turn down, the game has already changed. The customers have already started shifting. The technology has already advanced. The competitor has already gained ground.
If you wait for your numbers to decline before you make a change, it's already too late.
You're not being proactive, you're being reactive. And in a reactive mode, you're not choosing your future; you're desperately trying to salvage your past.
The most dangerous time to stop asking "what if" is when you think you don't need to.
When business is good, "what if" feels like pessimism. But it's not. It's insurance. It's the difference between being proactive and being caught off-guard.
Your competitors aren't resting because you're winning. Markets aren't pausing because your quarter was strong. Technology isn't waiting because you're comfortable.
So if you're reading this and thinking, "Well, things are pretty good right now, maybe I'll worry about this later," that's your answer. That's exactly why you need to ask "what if" today.
The AI Question Nobody Wants to Answer
Let's talk about the elephant in the room, artificial intelligence.
I've watched countless executives treat AI like it's just another tech trend. "We'll wait and see," they say. "Let's not overreact to the hype," they caution. "We need more data before we invest."
But here's the "what if" that should keep you up at night:
What if you're wrong about AI?
What if it isn't a bubble waiting to burst? What if it's not like blockchain or the metaverse or any of the other buzzwords that came and went?
What if AI is the next infrastructure layer of business itself?
Think about that for a moment. Not a tool. Not a feature. Not a nice-to-have. But infrastructure, as fundamental as electricity, the internet, or mobile computing.
What if, in five years, not using AI in your business is like trying to run a company today without email or a website? What if the question isn't "Should we adopt AI?" but rather "How far behind are we already?"
And the really uncomfortable part: What if your competitors are quietly figuring out how to use it right now, while you're still "waiting to see"?
They're not announcing it in press releases. They're not bragging about it on LinkedIn. They're just... doing it. Building it into their operations. Training their teams. Finding the edges that will become competitive moats.
And you? You're gathering more data. Waiting for the perfect moment. Telling yourself you're being prudent.
From 30,000 Feet to the Corner Office: What Air Traffic Control Taught Me About Management
Before I became a CEO, I spent years as an air traffic controller. And if there's one profession that forces you to embrace "what if" thinking, it's that one.
In air traffic control, reactive thinking isn't just bad management, it's catastrophic. By the time you're reacting to a problem, it's already too late. The planes are already too close. The weather has already turned. The system has already failed.
The entire profession is built on one principle: anticipate, don't react.
"What if this flight has an emergency?" "What if the weather deteriorates faster than forecasted?" "What if two planes end up converging on the same point?"
We didn't ask these questions because we were paranoid. We asked them because we were professionals. Because preparation isn't paranoia, it's responsibility.
And yet, when I transitioned into corporate leadership, I was shocked by how many executives operate in purely reactive mode.
They wait for the market to shift, then scramble to respond. They wait for competitors to innovate, then rush to catch up. They wait for technology to mature, then panic when they're years behind.
Reactive management is a path to failure. In air traffic control, we knew that. But in business? Somehow it's become the norm.
The Anatomy of a Better "What If"
Not all "what if" questions are created equal. Some are productive. Others are just anxiety dressed up as strategy.
Here's how to ask better "what if" questions:
1. Make Them Specific
Bad: "What if things change?" Good: "What if our largest customer moves 50% of their business to a competitor who offers solutions because of capabilities only made possible by, in the next 18 months?"
The more specific your "what if," the more actionable your response can be.
2. Attach Them to Signals
Bad: "What if AI takes over everything?" Good: "What if our customer support tickets that could be handled by AI reach 70%? What does that mean for our team structure?"
Look for concrete signals you can monitor. What metrics would tell you the "what if" is becoming reality?
3. Build Plan B Before You Need It
The point of "what if" isn't to predict the future perfectly. It's to have a Plan B ready before the world hands you a Plan C you didn't choose.
When you ask "What if AI capabilities becomes table stakes in our industry?", the next question isn't "Will it happen?" It's "What would we do if it does?"
Then you start preparing. Not committing. Not betting the farm. Just... preparing.
Maybe that means:
Identifying one workflow where AI could be tested
Training a small team on emerging tools
Allocating 5% of your innovation budget to experimentation
Building relationships with AI vendors before you desperately need them
4. Separate Exploration from Commitment
One reason leaders avoid "what if" thinking is they conflate asking the question with making a decision.
They think: "If I ask 'what if AI matters,' then I have to immediately invest millions in AI."
No. You don't.
Asking "what if" creates options. It doesn't force choices. It expands your decision tree so that when the moment comes to decide, you're not starting from zero.
The Questions You Should Be Asking Right Now
Let me give you some "what ifs" that are worth your time in 2025:
About Technology:
What if AI reduces the cost of knowledge work by 80% in the next three years?
What if our customers expect AI-level service speed from all vendors?
What if our product becomes a feature of someone else's AI platform?
About Markets:
What if our core customer demographic shifts their buying behavior faster than our sales cycle can adapt?
What if remote work becomes so accepted that geography becomes irrelevant for talent, making us compete globally for every hire?
What if the economic assumptions we've built our growth model on completely reverse?
About Competition:
What if a well-funded startup enters our space with AI-native operations and 1/10th our cost structure?
What if our biggest competitor isn't another company in our industry, but a platform that makes our service obsolete?
What if the barriers to entry in our market collapse due to new technology?
About Your Organization:
What if our top performers leave because we're not innovating fast enough?
What if the skills we're hiring for today are irrelevant in 24 months?
What if our company culture, built for stability, becomes a liability in a period of rapid change?
These aren't doomsday scenarios. They're strategic considerations. And the difference between a company that thrives and one that merely survives is often just this: which questions did they ask before they were forced to?
From "What If" to "Now What": Building a Proactive Organization
So how do you actually build a culture of proactive "what if" thinking?
Create Permission to Question
First, you have to make it safe for people to ask uncomfortable questions. In most organizations, the person who asks "What if we're wrong about our core strategy?" gets labeled a troublemaker, not a truth-teller.
Change that.
Make "what if" sessions a regular part of your strategic planning. Not just quick brainstorms, but structured time where the goal is to challenge assumptions, not defend them.
Assign "What If" Ownership
Have someone on your leadership team whose explicit job is to play devil's advocate. Not to be negative, but to constantly ask: "What are we not seeing? What could go wrong? What opportunities might we be missing?"
In military planning, they call this "red teaming." In business, we just call it good management.
Build Scenario Plans
Don't just ask "what if, map out what you'd actually do if it happened.
If AI becomes critical infrastructure in your industry, what's your 90-day response plan? Your 1-year plan? Your 3-year plan?
Having these scenarios ready doesn't mean you execute them immediately. It means that when the world shifts, you're not starting from scratch.
Monitor, Don't Just Predict
Finally, set up your early warning system. What metrics would tell you that one of your "what if" scenarios is starting to come true?
Maybe it's:
Customer support ticket volume that could be automated
Competitor announcements in AI
Changes in time-to-hire for key roles
Shifts in customer inquiry topics
The goal isn't to predict the future perfectly. It's to notice change early enough to respond deliberately instead of desperately.
The Cost of Not Asking
Here's what happens when you don't ask "what if":
Someone else does. And they prepare. And when the market shifts, they're ready and you're not.
You end up asking "now what?" instead of "what if?"
And the difference between those two questions is the difference between proactive strategy and reactive panic.
"What if" gives you options. "Now what?" leaves you scrambling.
"What if" is asked in boardrooms with time to think. "Now what?" is asked in emergency meetings at 11 PM.
"What if" is leadership. "Now what?" is crisis management.
The Question That Changes Everything
So let me leave you with this:
What if the thing you're most confident about is the thing you should be questioning most?
What if your core product, your go-to-market strategy, your operational model, or your competitive moat isn't as solid as you think?
What if the reason you haven't disrupted yourself is because you're too comfortable with who you are to imagine who you might need to become?
What if the next three years don't look anything like the last three?
You can dismiss these as paranoid. You can file them away as "good questions for later."
Or you can start asking them now, while you still have time to prepare instead of time to panic.
Start Today
Here's your homework:
Block 90 minutes on your calendar this week. Label it "What If Strategy Session."
Bring your leadership team. No laptops. No phones. Just thinking.
Ask the uncomfortable questions:
What if we're wrong about AI?
What if our market changes faster than we can?
What if our biggest advantage becomes irrelevant?
For each "what if," outline:
What signals would tell us it's happening?
What would our response be?
What can we do now to prepare?
Choose one scenario. Just one. And take one small action this month to prepare for it.
That's it. You don't have to solve everything. You just have to start asking better questions.
Because the most expensive words in business aren't "what if."
They're "I wish we had."
The choice is yours: Keep waiting for certainty in an uncertain world, or start asking "what if" while you still have time to do something about the answers.
After years in the tower and years in the corner office, I can tell you with absolute certainty: the leaders who thrive aren't the ones with all the answers.
They're the ones asking the right questions.
What if you started today?
"What if?"
Two simple words. Barely a sentence. Yet in my years working both as an air traffic controller and as a CEO, I've come to realize that this might be the most underused, and most powerful, question in business.
Not "What's our quarterly target?" Not "How do we optimize current operations?" Not even "What's working right now?"
But rather: "What if we're completely wrong about everything?"
The Comfort of Certainty (And Why It's Killing Your Business)
Many leaders avoid the "what if" question like the plague.
And I get it. I really do.
When you're steering a company, managing stakeholders, and responsible for people's livelihoods, uncertainty feels like weakness. Confidence feels like leadership. Admitting you might need to pivot, that your current strategy might be built on shifting sand, that feels dangerous.
But you know what's more dangerous? Being so committed to being right that you never prepare for being wrong.
"What if we're wrong?"
"What if the market shifts faster than we expect?"
"What if the next wave of AI isn't hype, but the new baseline?"
These questions don't make you a pessimist. They make you a realist. They make you the kind of leader who survives the storms that sink everyone else.
The Success Trap: When "Good Enough" Becomes Dangerous
Here's the paradox that kills companies: You're most likely to ignore "what if" questions when your business is doing well.
And that's exactly when they matter most.
Think about it. When revenue is up, customers are happy, and the board is pleased, who wants to be the person asking "But what if this all falls apart?"
When you're winning, questioning your strategy feels like self-sabotage. Why fix what isn't broken? Why risk disrupting a good thing? Why create problems where none exist?
I've seen it happen over and over. A company hits its stride. Growth becomes predictable. Processes get optimized. Everyone settles into a comfortable rhythm. And slowly, almost imperceptibly, the organization stops asking hard questions.
Success breeds complacency. And complacency breeds blindness.
When you're doing well, you start attributing your success to brilliance rather than circumstance. You assume your strategy is sound because the results are good. You mistake current performance for future immunity.
But here's what history teaches us: The companies that fail catastrophically rarely see it coming. And when we look back, the warning signs were always there. The market was shifting. Technology was evolving. Customer preferences were changing. Competitors were innovating.
The difference between the companies that survived and those that didn't wasn't information, it was willingness to question success while they still had it.
Blockbuster was profitable when Netflix was just a DVD-by-mail service. Nokia dominated the mobile market when the iPhone launched. Kodak invented the digital camera but couldn't imagine abandoning film. Yep all stories you have heard, but have you considered these examples in your own planning?
They weren't failing when they needed to ask "what if." They were succeeding. And that's precisely why they didn't ask.
Here's what every leader needs to internalize: Financial results are a report card, not a prediction.
Your quarterly earnings tell you how well you executed yesterday's strategy in yesterday's market. They don't tell you whether tomorrow's strategy will work in tomorrow's market.
By the time your financial results turn down, the game has already changed. The customers have already started shifting. The technology has already advanced. The competitor has already gained ground.
If you wait for your numbers to decline before you make a change, it's already too late.
You're not being proactive, you're being reactive. And in a reactive mode, you're not choosing your future; you're desperately trying to salvage your past.
The most dangerous time to stop asking "what if" is when you think you don't need to.
When business is good, "what if" feels like pessimism. But it's not. It's insurance. It's the difference between being proactive and being caught off-guard.
Your competitors aren't resting because you're winning. Markets aren't pausing because your quarter was strong. Technology isn't waiting because you're comfortable.
So if you're reading this and thinking, "Well, things are pretty good right now, maybe I'll worry about this later," that's your answer. That's exactly why you need to ask "what if" today.
The AI Question Nobody Wants to Answer
Let's talk about the elephant in the room, artificial intelligence.
I've watched countless executives treat AI like it's just another tech trend. "We'll wait and see," they say. "Let's not overreact to the hype," they caution. "We need more data before we invest."
But here's the "what if" that should keep you up at night:
What if you're wrong about AI?
What if it isn't a bubble waiting to burst? What if it's not like blockchain or the metaverse or any of the other buzzwords that came and went?
What if AI is the next infrastructure layer of business itself?
Think about that for a moment. Not a tool. Not a feature. Not a nice-to-have. But infrastructure, as fundamental as electricity, the internet, or mobile computing.
What if, in five years, not using AI in your business is like trying to run a company today without email or a website? What if the question isn't "Should we adopt AI?" but rather "How far behind are we already?"
And the really uncomfortable part: What if your competitors are quietly figuring out how to use it right now, while you're still "waiting to see"?
They're not announcing it in press releases. They're not bragging about it on LinkedIn. They're just... doing it. Building it into their operations. Training their teams. Finding the edges that will become competitive moats.
And you? You're gathering more data. Waiting for the perfect moment. Telling yourself you're being prudent.
From 30,000 Feet to the Corner Office: What Air Traffic Control Taught Me About Management
Before I became a CEO, I spent years as an air traffic controller. And if there's one profession that forces you to embrace "what if" thinking, it's that one.
In air traffic control, reactive thinking isn't just bad management, it's catastrophic. By the time you're reacting to a problem, it's already too late. The planes are already too close. The weather has already turned. The system has already failed.
The entire profession is built on one principle: anticipate, don't react.
"What if this flight has an emergency?" "What if the weather deteriorates faster than forecasted?" "What if two planes end up converging on the same point?"
We didn't ask these questions because we were paranoid. We asked them because we were professionals. Because preparation isn't paranoia, it's responsibility.
And yet, when I transitioned into corporate leadership, I was shocked by how many executives operate in purely reactive mode.
They wait for the market to shift, then scramble to respond. They wait for competitors to innovate, then rush to catch up. They wait for technology to mature, then panic when they're years behind.
Reactive management is a path to failure. In air traffic control, we knew that. But in business? Somehow it's become the norm.
The Anatomy of a Better "What If"
Not all "what if" questions are created equal. Some are productive. Others are just anxiety dressed up as strategy.
Here's how to ask better "what if" questions:
1. Make Them Specific
Bad: "What if things change?" Good: "What if our largest customer moves 50% of their business to a competitor who offers solutions because of capabilities only made possible by, in the next 18 months?"
The more specific your "what if," the more actionable your response can be.
2. Attach Them to Signals
Bad: "What if AI takes over everything?" Good: "What if our customer support tickets that could be handled by AI reach 70%? What does that mean for our team structure?"
Look for concrete signals you can monitor. What metrics would tell you the "what if" is becoming reality?
3. Build Plan B Before You Need It
The point of "what if" isn't to predict the future perfectly. It's to have a Plan B ready before the world hands you a Plan C you didn't choose.
When you ask "What if AI capabilities becomes table stakes in our industry?", the next question isn't "Will it happen?" It's "What would we do if it does?"
Then you start preparing. Not committing. Not betting the farm. Just... preparing.
Maybe that means:
Identifying one workflow where AI could be tested
Training a small team on emerging tools
Allocating 5% of your innovation budget to experimentation
Building relationships with AI vendors before you desperately need them
4. Separate Exploration from Commitment
One reason leaders avoid "what if" thinking is they conflate asking the question with making a decision.
They think: "If I ask 'what if AI matters,' then I have to immediately invest millions in AI."
No. You don't.
Asking "what if" creates options. It doesn't force choices. It expands your decision tree so that when the moment comes to decide, you're not starting from zero.
The Questions You Should Be Asking Right Now
Let me give you some "what ifs" that are worth your time in 2025:
About Technology:
What if AI reduces the cost of knowledge work by 80% in the next three years?
What if our customers expect AI-level service speed from all vendors?
What if our product becomes a feature of someone else's AI platform?
About Markets:
What if our core customer demographic shifts their buying behavior faster than our sales cycle can adapt?
What if remote work becomes so accepted that geography becomes irrelevant for talent, making us compete globally for every hire?
What if the economic assumptions we've built our growth model on completely reverse?
About Competition:
What if a well-funded startup enters our space with AI-native operations and 1/10th our cost structure?
What if our biggest competitor isn't another company in our industry, but a platform that makes our service obsolete?
What if the barriers to entry in our market collapse due to new technology?
About Your Organization:
What if our top performers leave because we're not innovating fast enough?
What if the skills we're hiring for today are irrelevant in 24 months?
What if our company culture, built for stability, becomes a liability in a period of rapid change?
These aren't doomsday scenarios. They're strategic considerations. And the difference between a company that thrives and one that merely survives is often just this: which questions did they ask before they were forced to?
From "What If" to "Now What": Building a Proactive Organization
So how do you actually build a culture of proactive "what if" thinking?
Create Permission to Question
First, you have to make it safe for people to ask uncomfortable questions. In most organizations, the person who asks "What if we're wrong about our core strategy?" gets labeled a troublemaker, not a truth-teller.
Change that.
Make "what if" sessions a regular part of your strategic planning. Not just quick brainstorms, but structured time where the goal is to challenge assumptions, not defend them.
Assign "What If" Ownership
Have someone on your leadership team whose explicit job is to play devil's advocate. Not to be negative, but to constantly ask: "What are we not seeing? What could go wrong? What opportunities might we be missing?"
In military planning, they call this "red teaming." In business, we just call it good management.
Build Scenario Plans
Don't just ask "what if, map out what you'd actually do if it happened.
If AI becomes critical infrastructure in your industry, what's your 90-day response plan? Your 1-year plan? Your 3-year plan?
Having these scenarios ready doesn't mean you execute them immediately. It means that when the world shifts, you're not starting from scratch.
Monitor, Don't Just Predict
Finally, set up your early warning system. What metrics would tell you that one of your "what if" scenarios is starting to come true?
Maybe it's:
Customer support ticket volume that could be automated
Competitor announcements in AI
Changes in time-to-hire for key roles
Shifts in customer inquiry topics
The goal isn't to predict the future perfectly. It's to notice change early enough to respond deliberately instead of desperately.
The Cost of Not Asking
Here's what happens when you don't ask "what if":
Someone else does. And they prepare. And when the market shifts, they're ready and you're not.
You end up asking "now what?" instead of "what if?"
And the difference between those two questions is the difference between proactive strategy and reactive panic.
"What if" gives you options. "Now what?" leaves you scrambling.
"What if" is asked in boardrooms with time to think. "Now what?" is asked in emergency meetings at 11 PM.
"What if" is leadership. "Now what?" is crisis management.
The Question That Changes Everything
So let me leave you with this:
What if the thing you're most confident about is the thing you should be questioning most?
What if your core product, your go-to-market strategy, your operational model, or your competitive moat isn't as solid as you think?
What if the reason you haven't disrupted yourself is because you're too comfortable with who you are to imagine who you might need to become?
What if the next three years don't look anything like the last three?
You can dismiss these as paranoid. You can file them away as "good questions for later."
Or you can start asking them now, while you still have time to prepare instead of time to panic.
Start Today
Here's your homework:
Block 90 minutes on your calendar this week. Label it "What If Strategy Session."
Bring your leadership team. No laptops. No phones. Just thinking.
Ask the uncomfortable questions:
What if we're wrong about AI?
What if our market changes faster than we can?
What if our biggest advantage becomes irrelevant?
For each "what if," outline:
What signals would tell us it's happening?
What would our response be?
What can we do now to prepare?
Choose one scenario. Just one. And take one small action this month to prepare for it.
That's it. You don't have to solve everything. You just have to start asking better questions.
Because the most expensive words in business aren't "what if."
They're "I wish we had."
The choice is yours: Keep waiting for certainty in an uncertain world, or start asking "what if" while you still have time to do something about the answers.
After years in the tower and years in the corner office, I can tell you with absolute certainty: the leaders who thrive aren't the ones with all the answers.
They're the ones asking the right questions.
What if you started today?
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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