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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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Play back what you heard

Forwarded this email? Subscribe here for more. READ TIME: 6 MINUTES | 27 MAY, 2026 | READ ON PHILHSC.COM I was the newest arrival to my infantry section. A section is one of three teams in a platoon, and on my first field exercise my section commander was delivering his orders to us. Military orders are delivered in a specific format designed for clarity and depending on the exercise or operation, they can range from lengthy and intricate to relatively straightforward. In that moment I was...

Lowering the tone of tension

Forwarded this email? Subscribe here for more. READ TIME: 8 MINUTES | 10 JUNE, 2026 | READ ON PHILHSC.COM The room had been going for forty minutes and nobody was listening anymore. I was there as an observer. The CEO ran a biotechnology company that had two therapies slated for market, and almost none of the pieces sat under one roof. Development in one place. Manufacturing in another. Distribution somewhere else again, inside a partner organisation with its own culture, its own incentives,...

Leading from insight an 'othering' culture

Forwarded this email? Subscribe here for more. READ TIME: 9 MINUTES | 3 JUNE, 2026 | READ ON PHILHSC.COM It doesn’t take long to see ‘us’ and ‘them’ cultures in organisations. It shows up in militaries, emergency services, break rooms and executive team meetings, and it operates whether it’s intended or not. I felt it soon after enlisting in the Army and again in my corporate jobs. I started paying closer attention to it recently. As the worst of COVID passed and the teams I work with began...

Earning the way back

Forwarded this email? Subscribe here for more. READ TIME: 8 MINUTES | 20 MAY, 2026 | READ ON PHILHSC.COM There's a very specific feeling that arrives when you've let someone down who trusted you. It sits in your chest. It’s heavy and it feels somewhere between guilt and shame. I remember feeling it for the first time at scale a decade ago, when I was building a company that could detect anything you heard on a commercial radio station and save it for later. We automatically captured ads,...

Two different contracts

Forwarded this email? Subscribe here for more. READ TIME: 7 MINUTES | 13 MAY, 2026 | READ ON PHILHSC.COM A month ago, during planning for a leadership session, my colleague commented, ‘They don’t seem to find joy in their work.’ I replied, ‘What if they’ve never experienced joy?’ The room went quiet as we thought about the consequence of that being true. The term joy comes up a lot in leadership. We tell people to pursue it and we write it into keynote addresses, but in that moment, one...

How credibility compounds

Forwarded this email? Subscribe here for more. READ TIME: 10 MINUTES | 6 MAY, 2026 | READ ON PHILHSC.COM I was sitting in a boardroom in Sydney with a deck I believed in, a team I was proud of and a company I knew would matter. Drop Bio Health was building something genuinely pioneering, a biological testing platform that could give people a real window into how their body was ageing and critical insight years before a chronic disease could be diagnosed. The science was solid. The vision was...

The Anatomy of Good Decisions

Forwarded this email? Subscribe here for more. READ TIME: 10 MINUTES | 29 APRIL, 2026 | READ ON PHILHSC.COM "Lads, that's the job. Let's talk options. Thoughts?" I was observing from the back of the room. The officer who said it had presented his commander's intent, the what and the why and then he did something most leaders rarely do. He got out of his own way. What followed was one of the most purposeful conversations I've witnessed in any organisation. Articulate disagreement. Humour....

The long hard path

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...

How to avoid being blindsided by detail

Forwarded this email? Subscribe here for more. READ TIME: 7 MINUTES | 15 APRIL, 2026 | READ ON PHILHSC.COM The document was on the table. It was a big deal and close to done. The company had been building toward this for months. The strategic logic was sound and there was in-principal agreement. All that remained was working through the final terms. The call came late one afternoon. The CEO I had been working with for months asked me to look it over because something felt off and she couldn’t...

Deals to be done

Forwarded this email? Subscribe here for more. READ TIME: 8 MINUTES | 8 APRIL, 2026 | READ ON PHILHSC.COM An exciting time is upon us. We are bearing witness to a transition in global power. One that has been building for years, accelerated by a miscalculation at the highest level, where the attempt to weaken an adversary produced a more dangerous one. No country or company is immune. And in that, if you're willing to look for it, lies the opportunity. The crescendo moment is closer than it's...