Five 10-minute curated insights in a private podcast to help you face CEO pressures. Then, each Wednesday, The Leadership Letter delivers one piece of clear, honest thinking from someone who has spent 20 years in the seat you're sitting in. Practical enough to use. Human enough to matter.
The long hard path
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Forwarded this email? Subscribe here for more. READ TIME: 8 MINUTES | 22 APRIL, 2026 | READ ON PHILHSC.COM 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.
See you next Wednesday, Phil Hayes-St Clair |
The Leadership Letter with Phil Hayes-St Clair
Five 10-minute curated insights in a private podcast to help you face CEO pressures. Then, each Wednesday, The Leadership Letter delivers one piece of clear, honest thinking from someone who has spent 20 years in the seat you're sitting in. Practical enough to use. Human enough to matter.
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