• Matthew Lerner

Overthinkers & Underthinkers

Let’s talk about overthinkers and under-thinkers — I suspect most of us are naturally one or the other. And if we're leading a startup, that becomes part of our team’s culture.

Some teams are paralyzed by debates at the expense of execution. (That’s me!)

Others are quick to act without stopping to consider the tradeoffs, which leads to wasted cycles. (Everyone’s busy, but the numbers aren’t moving.)

Do either of these sound familiar?

Teams adopt a culture of overthinking or underthinking — and either one can slow us down. Fortunately, it's an easy fix!

Simple next step

First, just paste this post into Slack and have an honest conversation about your team’s culture. Are you all more likely to overthink or underthink? Just acknowledging this can be helpful.


If your bias towards action is too strong, encourage your team to ask the following questions:

  • If we do this, what are we not doing?

  • How big could this be if it works?

  • Are there other things that make more sense right now? (That’s it, don’t overcomplicate it.)


If you’re inclined to waste time planning and debating what might go wrong, build a habit of ending every conversation with a decision and some next steps. Sometimes it’s just “Pencils down, let’s try it, and see what happens,” or “let’s put it in the backlog for now.”

And in either case, as you’re building your team, look for people who have the opposite inclination, and bring them in to balance things out. Honestly, you’ll probably annoy each other, but it’ll be in a constructive way.

I hope this helps!

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