READ TIME: 6 MINUTES | 31 DECEMBER, 2025 | READ ON PHILHSC.COM​

Tomorrow is 2026.

We can expect this year to move at pace. AI will continue reshaping industries. Tariffs will shift supply chains. Governments will remain unpredictable.

And I'd like to share with you a different way to make the big calls.

If you're still on a break, consider this an invitation to think differently about the year ahead.

What I've been observing

Over the past two years, I've sat with dozens of CEOs facing genuinely difficult decisions.

The stakes are high. The variables are complex. The consequences of being wrong are real.

They're studying AI because they need to understand how it affects their business. They're modeling tariff scenarios because supply chains are at risk. They're tracking geopolitical instability because it impacts their teams and operations.

This isn't paralysis. It's responsible leadership.

But here's what I've noticed: There's a point where gathering more information stops adding clarity and starts delaying the inevitable.

I've lived this before.

Years ago, I was running a biotech company and we had to choose which underlying diagnostic technology we'd build our entire platform on.

Both options were expensive. Both came with significant drawbacks. Neither was a slam dunk.

And the cost of reversing the decision was considerable.

We'd be locked in for years.

The stakes weren't abstract.

This decision would determine the company’s future.

So I did what felt responsible: I gathered more data. I consulted experts. I ran models. I looked for the certainty that would make the decision obvious.

It never came.

Eventually, I made the call. We picked one. It worked out.

But here's what I realize now: I should have framed it as a bet from the beginning.

Not because it would have made the decision easier, it wouldn't have.

But because it would have acknowledged the reality: This is hard.

The outcome is uncertain. The stakes are high. And it's still worth making the call.

Instead, I treated it like there was a "right answer" I just hadn't found yet. And that belief kept me stuck longer than served the business or my team.

A different way to think about it

So here's what I ask CEOs when they're stuck in this pattern:

What bet are you placing this year?

Not: What's your strategy?

Not: What's your plan?

What bet are you placing?

I've found this reframe changes everything.

First: A bet is a well-informed decision that your team can actually use.

It takes into account what you're good at, the market you're operating in, and why you have the right to win. It's grounded in reality.

But here's the kicker: it's also language people can actually repeat.

I've asked leadership teams how many people in their organisation can recite their company strategy word for word.

Most CEOs can count them on one hand.

But when a team understands the bet their company is taking? They can repeat it. They live it. They make daily decisions aligned with it.

"We're betting the market consolidates in the next 24 months, and we need to be the consolidator."

"We're betting that owning the customer relationship matters more than owning the technology."

"We're betting that AI will displace our current product, so we're building the thing that replaces us."

That's clear. That's actionable. That's something a team can rally behind.

Second: Bets acknowledge what we all know but rarely say out loud - uncertainty is real.

I've sat through enough strategy presentations to know what they're designed to do: create a feeling of certainty. To compel a Board or investors to back a direction.

But we're in a period where certainty is a myth. And as we were taught in the military: No plan survives first contact with the enemy.

Placing a bet, while it may be well-informed, openly acknowledges that the outcome is uncertain.

And that creates something valuable: vigilance.

When a team knows they've placed a bet, they stay alert. They watch for signals. They're ready to adapt when reality doesn't match the model.

Because it won't. It never does.

What we learn in the military

When I was in the Army, we didn't just make one plan. We made backup plans. Contingencies. We created redundancy so the team could continue to achieve its mission even when the primary plan fell apart.

But more importantly, we trained for adaptability. For being crafty. For overcoming adversity with whatever resources we had.

The mission intent was the important ingredient.

The ability to adapt when the plan failed was the essential ingredient.

That's what framing decisions as bets gives you.

Not false certainty. But the clarity to move forward and the flexibility to adapt when you need to.

How to think in bets

Former poker champion Annie Duke has written extensively about this, and she highlights three critical factors:

1. Thinking in Bets

View decisions as wagers on future, uncertain outcomes. This reduces emotional bias and improves objectivity.

You're not trying to be "right." You're trying to make the best decision you can with the information you have, knowing the outcome is uncertain.

2. "Resulting"

Don't judge a decision based solely on whether it had a good or bad outcome. Luck plays a major role.

A good decision can lead to a bad result. A bad decision can lead to a good result. What matters is the quality of the decision at the time it was made.

3. Diverse Truth-Seeking Groups

Collaborate with others to challenge your biases and get a more objective, accurate view of reality.

This isn't about consensus. It's about pressure-testing your thinking with people who will tell you where you're wrong.

What changes when leaders think in bets

When I see CEOs start thinking in bets, two specific shifts happen:

They develop a probabilistic mindset.

Instead of "I'm sure this will work," they start thinking in confidence levels.

"I'm 60% confident this bet will pay off, 40% it won't. Here's what would need to be true for it to succeed."

That simple shift changes how they lead. Because now they're not defending a position. They're testing a hypothesis.

They start using pre-mortems.

Before making the decision, they imagine a negative future. They ask their team: "It's 12 months from now and this bet failed. What happened?"

Then they work backward to identify the pitfalls and either prevent them or build contingencies. Here’s a pre-mortem playbook you can use.

I've watched this exercise save CEOs from catastrophic blind spots.

Two questions to help you succeed

Once you've identified the bet you're placing, I've found there are two questions help:

1. How will I lead through this?

Not: What will I do?

But: How will I show up?

If the bet requires speed, the team needs to see you model decisiveness. If it requires experimentation, they need to see you comfortable with failure. If it requires resilience, they need to see you calm under pressure.

2. How do I need my team to show up?

This is where most CEOs I work with get stuck. Not because they don't know the answer intellectually, but because they haven't done the work to articulate it clearly.

What I've learned is that teams need three things:

1. They need to understand the intent behind the bet
2. They need to help craft it
3. And then they need to get behind it (even if they personally disagree with the specific bet) because they understand the underlying intent and believe it's the best bet for this moment

Most importantly, they need to be able to adapt. To be crafty. To overcome adversity when the plan meets reality and falls apart.

Because it will.

This is the work I do with CEOs in one-to-one coaching: helping clarify the bet, defining how you'll lead through it, and building a team that can adapt when the plan meets reality.

If that resonates, let's talk.

What actually matters

The world isn't going to get less complex. The disruption isn't going to slow down.

AI will continue to reshape how we work. Markets will shift. And you can keep studying the problem or you can place a bet.

A well-informed bet. A bet your team can understand and live. A bet that acknowledges uncertainty and prepares you to adapt when reality doesn't match your model.

Great CEOs aren't the ones who have all the answers.

They're the ones who are willing to make the call, knowing they might be wrong and build the capacity to adapt when they are.

The bottom line

Stop admiring the problem.

The year ahead will be uncertain. The disruption will continue. The decisions will be hard.

But the cost of waiting for certainty is higher than the cost of being wrong.

So here's my question for you: What bet are you placing this year?

Not your strategy. Not your plan.

Your bet.

The thing you're willing to commit to, knowing the outcome is uncertain, because it's the best move you can see from where you're standing right now.

Reply to let me know. I’d love to help where I can.

Thanks for being here, I appreciate you reading today's essay.

THE PARTNERSHIP PLAYBOOK PODCAST

Here are this week’s podcast episodes for your walk, commute or workout.

PARTNERSHIPS MOMENT

EP 128 - 8 min:10 blind spots that GTM leaders actively work on to drive growth. Ever feel like your deals were solid until they weren’t? When Q1 slips, it’s rarely the market’s fault. It’s often the quiet habits inside leadership routines that go unnoticed. In this episode you’ll learn how to: Replace wishful thinking with probability-driven strategy, stop pushing pressure and start enforcing process to drive 2026 growth.Listen on Apple Podcasts | Spotify​

LEADERSHIP MOMENT

EP 144 - 11 min:How CEOs can help develop their leaders. What happens to growth when your business scales faster than the leaders running it? Every CEO eventually feels it. In this episode learn how to identify when your leadership team is stalling, understand the three levers CEOs must pull to accelerate leadership growth and lift your leaders to the next altitude. Listen on Apple Podcasts | Spotify​

CEO INTERVIEW

EP 134 - 1 hr 5 min:Ryan Hawk. Whether you're leading a team, selling under pressure, or building a movement, this episode with Ryan will flip your assumptions. From his journey through sports, sales, podcasting, and publishing, Ryan unpacks how commitment, standards, and relationships drive real results. Listen on Apple Podcasts | Spotify​

See you next Wednesday,

Phil Hayes-St Clair
Executive Coach

​Find me on LinkedIn​

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