The long hard path
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The decisions you make as a CEO don't have clean edges.
You know you're the one who has to make the call. You also know that no version of the outcome is going to feel entirely right.
What's harder to see is how they compound because each one is informed by the last. Each one slightly reshapes how you see the next one coming.
You might start to notice the patterns you reach for when you’re under pressure. They’re framings you return to when the team is tired and everyone wants a resolution. And over time, if you’re paying attention, you start to see that your decision-making doesn’t just affect outcomes. It shapes who you’re becoming as a leader.
Last week I spoke with Georgie Holt, CEO of Flight Story, when I asked her to finish the sentence “Leadership is...”
She didn’t hesitate.
‘Making difficult decisions.’
Georgie wasn’t dismissing the rest of it. The vision, the culture, the ability to bring people with you. All of that matters, and she knows it. What she was naming was the part that’s hardest to talk about honestly. Because every leader walking through the door believes they can inspire and build and communicate.
The part that quietly separates good from exceptional, she said, is whether you keep choosing the harder answer. Not once. Consistently, over time, when it would be easier not to.
She went further. The difference between a good idea and a global brand, she told me, is compounding choices. Not one brave bet. A sustained series of difficult ones, taken consistently enough that they accumulate into something real.
This is a critical insight because we conceptually understand that decisions compound. We just rarely give ourselves the time or space to examine how our approach to decision-making is itself evolving.
What patterns do you reach for under pressure?
What conditions would genuinely change your mind on something (and are you seeking those conditions, or looking for an easier path)?
What does your decision-making look like when the company is fatigued, when the board is unsettled, when the options in front of you are all imperfect?
These aren’t abstract questions. They’re the difference between a CEO who gets sharper over time and one who carries more armour and spends more time defending their position.
The role is a compounding series of difficult decisions. Which means your approach to making them compounds too. In whatever direction you take it.
Which brings me to the three questions I use with the CEOs I work with and why so few can answer them cleanly the first time.
Are you evolving?
Georgie talked about her own decision-making in a way I found unexpectedly honest.
On her best days, she said, she’s courageous, dedicated, obsessed.
On her hardest days, she’s controlling.
She doesn’t treat that as a character flaw. She reads it as a signal.
When the controlling tendency appears, something upstream has drifted off course. It could be her schedule, her team’s capacity, a standard she let slide, event the decision to hold on too tight is usually downstream of a dozen smaller decisions that didn’t hold the line.
That’s the compounding effect working in reverse.
Which brings me to three questions I use with every CEO I work with.
Run them honestly against your last five significant decisions and see what you find.
QUESTION 1: What are you actually looking for?
When you’re evaluating a decision (a piece of work, a strategic call, a critical hire), what has to be true before you’ll commit?
Most experienced leaders have a list. They just haven’t written it down. It lives in their gut and gets expressed inconsistently, especially under pressure. And your team is constantly reverse-engineering it.
I suggest giving them the original.
Not as a confession. As a briefing.
Tell them what you’re looking for on a good day and what you retreat to on a hard one.
Tell them what signals matter most to you and which ones you’re prone to over-index on when you’re tired or under pressure. And don’t mistake this vulnerability for weakness. It’s one of the most useful things a leader can do for the people around them.
When your team knows this, they stop spending cognitive energy trying to read the room and start spending it on the work. They can navigate toward what actually matters to you rather than what they think might matter today.
The result is they can support you, not pander to you, because they understand the difference between a standard you hold and a state you’re in.
The CEO who has done this work carries less. Not because the decisions get easier, but because they’re no longer carrying them alone.
QUESTION 2: What would change your mind?
For any decision you’re holding open, there are conditions under which you’d move.
The question is whether those conditions are real or cosmetic.
Are you genuinely open to being wrong, or managing the appearance of openness?
There’s a tell: if you can’t name what would change your mind, you’ve likely already made the decision and you’re just waiting for enough time to pass to announce it.
QUESTION 3: Are you seeking the harder answer?
Georgie put it plainly: fast, cheap, and good don’t come together without significant sacrifice. The leader who names the trade-off out loud, in the room, before the work starts, trains their team to think that way too. The one who lets it slide, even once, trains them in what’s actually acceptable.
Be curious
The decision-making of leaders who compound well share one orientation. They’re curious about their own patterns.
Not defensive or obsessed with them.
Curious.
They treat how they make decisions as something worth understanding, not something to defend.
Georgie framed the destination through self-awareness and agency. High levels of both are what she wants most for every person in her orbit. Awareness is understanding who you are and how you actually operate. Agency is the ability to make real choices about how you lead and where you spend your time.
That’s the compound interest of this work.
And that’s what good coaching accelerates. Not shortcuts. Not a five-step path to easier decisions. An honest look at how you’re making the hard ones. What’s working, what’s becoming a liability, and what the next version of your leadership needs to look like.
The path is still long. But you don’t have to figure out the patterns alone and there’s every reason to enjoy it.
PS If this essay resonated, Episode 190 (FlightStory’s Georgie Holt on leadership, obsession and the long hard path) from my podcast is worthy of your time. Listen to it on Apple Podcasts or Spotify
Work with Phil
CEO Coaching — For CEOs who want to lead with clarity and grow their business without sacrificing what matters most. A tailored 12-session experience across three dimensions: scaling you as a leader, elevating how you lead others, and building conditions for sustainable growth.
I've spent 20+ years leading, building and recovering businesses and coaching CEOs doing the same. I work with a small number of people at a time. If the timing is right, let's talk.
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