How I’ve Changed as a Leader

This is my second time leading an endeavor.

The first time, I succeeded two CEOs (Sarah Usdin and Matt Candler) in leading New Schools for New Orleans.

Now I’m working with a great team to coordinate the education investments for two philanthropists.

I’m nearly a year into my new role, and a few recent events have caused me to think about how I’ve changed.

In case it’s of use to others, here’s some thoughts on how I’ve changed.


1. I put less weight on three year strategic plans and more weight on quarterly objectives.

While I still think it’s important to have a long-term theory of change and BHAG – as well as sketch out three year goals – I think most of this can be done in a few paragraphs, a few slides, and a spreadsheet with a few tabs. I used to have a greater belief in the utility of longer-term plans, as well as the detail such plans required.

Now, I think three year and one year goals are useful for vision setting and team alignment, but that when comes to really executing work in fluid environments, you can really only plan (and hold people accountable) for the next 3-4 months of work.

This might be different in more stable industries or organizations.

2. I’m less willful. 

I worry about this, but I do think that I’ve softened a bit in my stubbornness and doggedness. In some sense, this is good, as I’m much more open to pragmatic solutions and compromises, as well as novel ideas that originate from people very different than myself. I also care less about being proven wrong, and am more willing to rapidly adopt solutions that are born out of realizing my errors.

On the other hand, I sometimes wonder if it’s better to be 65% right and 85% obsessed than it is to be 85% right and 65% obsessed.

The world often bends to doggedness.

3. I try to escalate bets.

This is tied to (3), as when you’re sure  you’re right the objective is to go big on what you believe rather than testing what you believe.

Now, I try to find lower stakes ways to test my beliefs before going big.

The risk here, I think, is being less disciplined on what you believe because you’re willing to “fail fast,” as they say.

4. I trust myself less in interviewing candidates.

I try to follow all the best practices in interviewing (top grading, etc.), but ultimately I spend way more time on references than I used to. Ultimately, the math here is simple: I put more weight on the views of people I trust and have known a candidate for years than I do my own views that have been formed after a few hours of interviews.

5. I better understand the connection between my own health and my ability to lead. 

This one I’m crystal clear on: I lead better when I exercise, meditate, and get enough sleep.

When I don’t take care of myself, it is hard to differentiate whether negative thoughts are arising from legitimate work concerns or whether they are arising from a lack of healthiness. It is hard to lead when you can’t tell the difference.


There is one thing that has roughly stayed the same: I lead and execute by harnessing systems level momentum.

Some people build great products, others narrow in on a perfectly tuned strategy.

I don’t think I’ve really ever been able to do either of those things; rather, I think my skill has been in understanding broadly what a system is capable of becoming, and how it might get there. In this sense, I can see the Northstar, and have a decent idea on what levers to pull and what levers to leave alone – but just about everything thing else is a mess that must be worked through via trial and error – sometimes with more error than I would like.

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