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Why Startup Leadership Feels So Lonely
Startup leadership is lonelier than anyone admits. Here’s why it feels that way, and the three supports every leader needs to make it feel lighter.
Dec 9, 2025
9
1
1
Lessons for new leaders
Every new leader wrestles with the same tension: move fast or listen first? Here’s how to get the timing right so people actually follow you.
Dec 2, 2025
26
1
"Disagree and Let’s See"
An alternative to "Disagree and Commit." A practical way to handle decisions you disagree with by treating them as experiments, not battles to be won.
Nov 18, 2025
26
2
3
Letter Bombs
We’ve all been tempted to promise a title or guarantee someone they’ll always be the most senior person -- just to close the candidate. But those…
Sep 3, 2025
15
1
Happy Friction
Happy friction is like a speed bump. It’s something you add on purpose to make people pause. Ideally, not because you’re afraid to delegate, but because…
Jul 15, 2025
14
Work Grief
Work Grief is something we don’t talk about enough. And it is everywhere.
Aug 15, 2024
24
3
Deciding when it's time to fire someone
One of the hardest things to do as a manager is decide to fire someone. Particularly if you're a new manager, you tend to spend a lot of time blaming…
Jul 16, 2024
22
1
Developing high performers
Most managers see high performers and just leave them alone because they are performing well. But I think high performers are where all the potential of…
Nov 1, 2023
26
1
2
Layoff lessons: Four things I wish I knew
Regardless of how the company got into the situation, layoffs are a terrible experience for everyone on all sides – the planners, the leavers, and the…
Aug 15, 2023
21
2
1
Manage the What, Not the How
Controlling how work gets done only makes your company slower. Employees will inevitably do things that make you cringe, take different approaches than…
Jul 25, 2023
41
2
4
Decision-making
A long time ago I was an Instructor at the National Outdoor Leadership School (NOLS). NOLS uses wilderness expeditions as a way to teach leadership…
Jun 27, 2023
37
5
1
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…
Apr 14, 2023
57
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