Hi Reader, A few years ago, I worked with a leadership team at a Series C software company. On paper, they were perfectly aligned. Strategic plans were approved unanimously. Everyone nodded in meetings. Decisions passed without friction. And yet nothing moved. Projects stalled, timelines slipped, and initiatives that everyone had "agreed to" kept getting quietly deprioritized. The CEO was baffled. How could a team that agreed on everything execute on nothing? When we dug in, we found the...
3 days ago • 2 min read
Hi Reader, A few years ago, I worked with the CEO of a fast-growing company. He was deeply committed to his people: Generous with equity, flexible on hours, always available. But his company had a problem. They couldn't kill anything. Every initiative seemed to live forever. Their roadmap was cluttered with half-finished projects. Teams were stretched thin, saying yes to everything and finishing nothing. He kept trying to fix it with reorgs, new prioritization frameworks, or hiring new...
10 days ago • 1 min read
Hi Reader, In our last email, we explored the first pillar: We all want to be part of something exceptional. The desire to contribute, to win together, to be part of something meaningful are all already there in your people. The work is about unlocking that hunger. Let's dive in to the second pillar of fulling leadership: Pillar Two: Where it hurts is where you'll grow We point to this frequently in terms of self-discovery: Your triggers are a gift. They tell you where your unexamined...
17 days ago • 1 min read
Hi Reader, Over the course of 30 years, I’ve worked with hundreds of leaders. And I often hear the same story: “I feel like I’m alone in this.” So many leaders feel like success depends on them. That at the end of the day, they’re the ones truly responsible for everything. So they work longer hours than anyone else, get involved in every decision, and carry the strategy, the culture, the execution. All based on the quiet belief that no one else will do this if I don't. But when you slow down...
24 days ago • 2 min read
The AOA Leadership Newsletter Hi Reader, I''ll be holding a rare Q&A on February 2, exclusive for leaders who are interested in learning more about how we approach leadership and the Council. You'll get the chance to ask questions about the program, as well as ask any strategy questions you may have for Rapid coaching. Reserve your seat here. The Hidden Cost of Self-Reliance Self-reliance began the first time you realized you weren’t going to be taken care of. It was when you learned, often...
about 1 month ago • 2 min read
The AOA Leadership Newsletter Hi Reader, The atomic structure of every company consists of two things Your decisions Your relationships If these two things are high quality, the company will succeed. If they are not, it will fail in the long run. With the Great Decisions Course coming up this January, I was inspired to talk about decision-making in leadership. Today's teaching will be diving deep into the inner mechanisms of decision-making. The Neurology of Decisions You’ve probably been...
2 months ago • 1 min read
The AOA Leadership Newsletter Hi Reader, A founder I worked with years ago told me that he hated selling his team. Board meetings were easy for him. Investor pitches were fine. But the moment he had to “sell” his own team on a new direction, something tightened in him. He’d over-explain, talk too fast, and push too hard for agreement. And the more he pushed, the more the room pulled back. One day, after watching another meeting derail, I asked him what he was trying to avoid. He said, “I...
3 months ago • 1 min read
The AOA Leadership Newsletter Hi Reader, Johannes Landgraf had everything most founders want. His company had just raised $25M, big-name banks were using his product, and over 2 million developers were on his platform. From the outside, it looked like everything was amazing. From the inside, he could see a different reality. The product architecture that got them here couldn’t get them where they needed to go. It created friction for customers and slowed his own team down. Staying the course...
3 months ago • 1 min read
The AOA Leadership Newsletter Hi Reader, An old client of mine was constantly terrified of failing. Every week, she’d bring me a new variation of the same worry: “What if this product doesn’t work?” “What if my investors lose faith in me?” “What if I just… can’t pull it off?” On paper, she was doing great: Her company was growing fast and had just closed a Series A. Like every founder, she ran into some speedbumps here and there. But even when she succeeded, her anxiety never went away. Every...
4 months ago • 2 min read
The AOA Leadership Newsletter Hi Reader, There was a CEO I coached once who couldn’t stop talking about recognition. He’d say things like, “I just want my team to know how much I’m doing behind the scenes.” Or “It feels like no one appreciates how much I’ve built here.” A few weeks later, I went to visit his team during an offsite to see what was happening. What I noticed was that his team actually deeply respected him. Yet, every time praise came up, he dodged it. When employees brought up...
4 months ago • 2 min read
