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Lessons

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Time is emphasis: planning your calendar as a leader
As an executive, everything flows from how you spend your time. You set a meeting, everyone rearranges their schedule. Time is emphasis, and your…
11
Founder Mode: A Liar’s Perspective
If you work in tech, there is no doubt you have stumbled into a conversation in the last week about Paul Graham’s article, Founder Mode.
9
10 things I wish I knew about careers when I started
Over my 20 years since college, I’ve become a big believer in the winding path as a powerful way to figure out the highest and best value you can bring…
10
There’s No Such Thing as a Generalist
Generalists vs. specialists — which is better and why? You’ve probably come across at least one think-piece or thread on this topic. It’s everywhere…
7
J-Curves vs Stairs: Two Approaches to Career Growth
A J-Curve is what I call a risky career choice with a potentially big payoff. It’s a choice where you bet that you can transfer the skills you currently…
3
Make It Easy to Draw the Elephant
Great communication is simple if you think about it as “connect the dots”. It isn’t about talking more—it’s about creating clarity and alignment. Your…
Part 1: Compensation for start ups: A leveling matrix that scales
This article is part of a series on compensation for startups.
1
How to take time off and use it well
I’ve been having a bunch of conversations with Glue People about how and whether to take time off between jobs. When I say take time off, I mean leaving…
8
Mapping your company's year: how to sequence the big processes
There are a handful of recurring, company-wide activities that influence how everyone spends their time, including board meetings, business reviews…
2
Captains
Captains is an ownership model that we implemented at Lambda School that is much simpler than models like RAPID or RACI. It is an elegant and simple…
Choosing your next job
Someone asked me to share how I think about choosing jobs and roles particularly once you’re at a point in your career when you have choice (or maybe in…
3
Addition vs Subtraction
“Organizations are horrible at subtraction.” Someone said that to me a couple of months ago, and I haven’t been able to stop thinking about it since. It…
2
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