When a bet on a CEO goes wrong, the cost shows up later: lost years, lost value and sometimes a board bringing back the leader it replaced. But the mistake usually happens much earlier, at the moment everyone in the room felt sure.

Think about how carefully most big decisions are checked. A major acquisition gets months of financial diligence. Lenders model every scenario. Lawyers review every clause. Yet the decision about who will run the company, the one that shapes all the others, too often rests on a few long relationships, a strong interview and references who mostly know each other.

That gap is what this newsletter is about.

What Leadership, Underwritten is

Every two weeks, I’ll take one leadership decision from the news, such as a CEO hire, a firing, a succession or a shared top seat, and look at it the way a diligence team would. What did the decision-makers actually know, and how did they know it?

The goal is not to grade the leaders. It’s to learn from how the decision was made, so the next one is made better.

Why I’m writing it

I spent my career in operating roles across CPG, media, music and tech, many of them in the C-suite: Mondelēz, Sony Music, American Idol through its sale to Apollo, TheBlaze, MediaMath, Garth Brooks’ drive-in concert experience and the venture-backed startup EarBuds. Along the way, I was often one of the people investors and buyers were betting on.

One thing stuck with me: when big money changes hands, a lot of it rides on what people believe about a few leaders. And those beliefs are often built on less evidence than anyone in the room realizes.

Today, through Gannett.Partners, I provide independent diligence on the founders and CEOs a business depends on, for boards, investors, sponsors and family offices. I’m also an Entrepreneur in Residence at Yale Ventures. This newsletter applies the same lens, in public, to the leadership decisions everyone is talking about.

What you can expect

  • A new case every two weeks, built on a current leadership decision and public sources.

  • One idea from my “count the roots, not the voices” diligence method in each issue, such as why familiarity is not independence, or why a shared top seat needs its decisions assigned in writing.

  • Five practical tests you can apply to your own decisions about leaders.

  • A fair reading of every case. No hit pieces, no predictions. Just a clearer way to look at the bets we make on people.

Who it’s for

  • Board members, especially those on nominating, compensation and succession committees

  • PE and venture investors backing founders and management teams

  • Family office principals and allocators who invest in people as much as companies

  • Board counsel and advisors who help clients make these calls

If you’ve ever signed off on a leader, a deal or a contract extension and later wondered what you missed, this is for you.

Start here

The first three issues are already published:

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Subscribe to get each issue as it’s published, by email at leadershipunderwritten.com or on LinkedIn.

And if a leadership decision in the news has you wondering what the board actually knew, send it my way. The best questions may become future issues.

Chris Gannett is the founder and CEO of Gannett.Partners, a nationally recognized, Dallas-based firm that provides independent diligence on the founders and CEOs a business depends on. Boards, investors, sponsors and family offices use that work to price and protect the value they're betting on.