In 2013, I had breakfast with a friend. We were both in our first COO-like roles after Facebook — his at a bigger company, mine at a small start-up. As…

October 2022

Someone sent me an email asking about how I recommend running business reviews (cadence, who attends, format, etc). I jotted down a fast response and…
This is a post about the single most important thing you can do to make it easier, smoother and more fun to scale past 50 employees (and on to hundreds…
If you're a leader in an organization that is going through a lot of change or scaling quickly, chances are that every single member of your team is…
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September 2022

A while ago, I wrote a post about why it get so hard once you scale past 50 employees. Afterwards, someone asked me what I think the most…
“Organizations are horrible at subtraction.” Someone said that to me a couple months ago, and I haven’t been able to stop thinking about it since. It is…
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I was introduced earlier this year to the concept of the Trust Battery and it has rapidly become one of the metaphors that I rely on regularly. I…

July 2022

Thanks for reading Lessons! Subscribe to receive new posts. First of all let me say, I seem to only take jobs that I feel super unqualified for, and the…
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A while ago (feels like 100 years, was actually only 8), I wrote a basic compensation guide for a founder I was helping out who was struggling to manage…
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April 2022

Hi friends! In terms of who I write for, this is one of those posts that is aimed at founder/CEOs but much of it can likely apply to leaders in bigger…
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March 2022

Hi friends! In terms of who I write for, this is one of those posts that is aimed at founder/CEOs but much of it can likely apply to leaders in bigger…
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Hi Friends! Sorry for the radio silence. With everything going on in Ukraine and with my own travels, I have been having trouble finding the right…
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