The distortions that produce bad outcomes at the leadership level are rarely dramatic. They accumulate quietly — in the assumptions you stopped questioning, the options you stopped considering, the complexity you kept adding because adding felt like progress. By the time the cost becomes visible, the decision is long past.
Most leaders don’t lack intelligence or experience. They lack a standing outside perspective from someone with no stake in the outcome and a specific focus on the conditions that make good decision-makers go wrong.
That’s what this engagement is.
This is a private, ongoing advisory relationship limited to a small number of founders and senior executives at any given time. We meet for one hour every week or every other week — consistently, over time — to examine the decisions you’re navigating and the environment producing them.
Think of it as having a consigliere — in the classical sense — whose only agenda is the quality of your decisions.
The first 90 days function as a diagnostic. We’re not just working through immediate problems. We’re building a working map of your specific decision architecture — the recurring patterns, the persistent blind spots, the conditions under which your judgment is most likely to be compromised. That 90-day period concludes with a structured debrief: a written summary of what we’ve found and a framework for what to watch going forward.
After 90 days, the engagement continues on an annual basis. The map has been built. The work shifts to early warning — catching the distortions before they produce outcomes you can’t reverse.
Founders and senior executives who make consequential decisions regularly and who suspect — or know — that something in their decision environment isn’t working as well as it should. You don’t need to be in crisis. The value compounds most for people who are functioning well and want to stay that way.
This engagement is not coaching. It’s not consulting. It’s not therapy. If you’re looking for someone to validate your instincts, this isn’t it. If you’re looking for someone to help you see what you can’t see from where you’re sitting, it might be exactly right.
If your instinct is that your decision-making needs minor adjustments, this probably isn’t the right fit. The work we do here operates at a deeper level than process refinement.
If you’re looking for confirmation that your current approach is sound, this isn’t the place to find it. That’s not a criticism — it’s just an honest description of what this engagement is and isn’t.
And if you’re not ready to have your assumptions examined seriously and occasionally challenged directly, the value won’t be there regardless of how capable either of us is.
The people who get the most from this engagement arrive with strong convictions and the genuine willingness to question them. Those two things together are rarer than you’d think.
My career began inside some of the world’s largest global corporations, where I watched decision distortion operate at enormous scale — consequential, recurring, and almost entirely invisible to the people producing it. For the last 20 years, that same work has been focused largely on the entrepreneurial ecosystem — in early and growth stage companies, in the firms that fund them, and in the organizations that serve them. But I have also spent a significant amount of time with credit unions and financial services organizations, where the decision environment carries its own particular pressures and the cost of distortion is rarely visible until it’s already expensive.
What that breadth of experience produces is a framework — not a packaged system to install, but a hard-won structure for recognizing the specific distortions that lead capable people to outcomes they didn’t see coming. It’s the kind of pattern recognition that only develops when you’ve watched the same mistakes made across enough contexts, at enough stages, by enough otherwise exceptional people.