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.
Earning the way back
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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, offers, interviews and music without touching your phone while driving. If you've used Shazam, you'll know the experience. We extended it and it worked. A regional radio station came on board to test it. Then a large national network decided to trial it across one of Australia's biggest markets. Our small team moved technical heaven and earth to make it happen. We had sold magic, backed it up with live, real-time data and built a technology from scratch. What we hadn't done was think clearly enough about what that data would mean for their business. For the first time in the history of radio, a network had granular data about who was listening and when. It was powerful information. The problem was they didn't know how to use it with their advertisers. We had given them a capability they weren't ready to monetise. Instead of opening a door, we'd handed them a key with no lock to put it in. They didn't continue the relationship. Our investor-backed business came to a standstill and the company was eventually wound up. Our team was out of a job, our investors lost money and I felt like I had broken trust with people who had placed it with me. Episode 201Last week, I published Episode 201 on the Partnership Playbook podcast (How smart GTM leaders enter markets they don't own) about how partnerships allow companies to borrow existing trust rather than build it from scratch. It resonated more than I expected. That weekend, my good friend Ben messaged me with this question after listening. "But how do you get trust back if you've partnered with another organisation and you've let them down in the delivery?" I nodded as I read it. I've been there. And I've spent a lot of time since that radio company, across the businesses that followed and in my coaching work, thinking about what the path back to trust actually looks like.
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.
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,...
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...
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...