← More reflections Weekly reflection 
Michael Greenspan · June 29, 2026
A Leader Doesn't Have to Know
Michael Greenspan · June 29, 2026 Monday mornings, I send you something short to sit with. Not advice or a framework, but a question, and some room to think it through yourself.
Something that comes up with leaders who used to take pride in being the engineer with the answer is how exposed it feels to not know.
You think you’re supposed to be the status expert for your VP, the product expert for your engineers, the prophet for your PM…
A simple “I’m not sure” can feel like a failure.
But it rarely is.
A few questions to ponder:
- What truth have you softened, or risk have you kept to yourself, to avoid looking unsure?
- Setting aside how you’ll look, what does this situation actually need from you?
- Where are you working harder to avoid looking dumb rather than to be useful?
- What would change if your job here wasn’t to have the answer, but to help your team reach theirs?
The reframe: A leader doesn’t need to have all the answers. The job is to stay calm and hold course when the answers aren’t knowable yet.
Have a great week!
— Michael
These weekly reflections aren’t about doing more or fixing yourself. They’re a moment to slow things down and notice what’s actually going on. Because noticing is usually where the change starts.
P.S. These are yours to keep private. But if you’d like to think through this one together, just reply. I read every one.