Why your team isn't taking risks.

Is your team playing it safe? Try this thought experiment.

Every founder struggles to get their teams to take risks and try bold things – a startup cannot succeed without courage and ambition.

You tell everyone that “failure is OK,” but in reality… 

Nobody believes you.

The result? Small ideas. Slow progress. Overthinking. Perfectionism.

It’s incredibly hard to get a team to dream up truly ambitious ideas, pursue them quickly, and embrace failures as learning.

Why previous approaches failed

Why is this so hard for people?

Because we’re hard-wired to want to do a “good job,” (e.g. “straight A’s”). That’s the optimal strategy in school and in "normal" jobs.

You can't change that, it's hard-wired.

What if, instead of fighting human nature, we simply reframed what counts as a 'good job'?

Here’s what I mean. Try this thought experiment… 

1,000 Wrong Turns

We all know that every great startup made plenty of wrong turns. A16Z calls it “the idea maze.” AirBnB took 5 years to get traction, Slack took 7 and Notion needed 10.

How many wrong turns will your business need to make?

For the sake of discussion, let’s say you need to make exactly 1,000. Imagine that after 1,000 failed experiments, attempt 1,001 would catapult you to a million customers.

If you knew that, what would you do differently?

You would start testing stuff like crazy. Every department. Ten tests per week. Per employee. You’d hire data scientists and actual scientists, you’d buy testing software, run competitions and show testing scoreboards in every room.

You’d have one clear goal: Experiment more.

Of course the actual number is not 1,000. We can't know the actual number. 

But what does that change?

If it’s a known number or an unknown number, why would that change your strategy?

You still need to experiment as much as possible.

If your current approaches aren't working, they aren't going to magically start working. You're missing information that can only come from trying new things—things that will probably fail. But that's the point.

Why this works better than “move fast and break things” posters

Instead of just prodding everyone with platitudes, this thought experiment reframes failurefrom "consequence" to "essential currency." The number 1,000 turns an abstract concept into a concrete tangible goal.

(The same way that the best salespeople count each rejection as a step on the path to "yes.")

You get what you measure. When you focus on attempts rather than just wins, your team can still be perfectionists – but with a better definition of perfect. 

I hope this helps!

I share something like this every week – read them all and subscribe here.