In times of economic uncertainty, like many startups have been going through, it’s natural to opt for playing it safe. However, deciding to do so can risk your organization forgetting what startups should be about: taking the right risks. Sometimes, the best thing we can do is bang our head against the wall for a bit.

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Suspension of Disbelief

More than a decade ago, I was sitting through an exam for an algorithm and computational complexity course. I finished the entire thing except for a single question that I continued battling for over an hour. Whoever compiled the exam accidentally asked us to find a polynomial time solution for an NP problem. Let me tell you, I never would have understood how to tackle this had I not honestly believed it was possible to solve. After a long while, I was able to articulate the proof showing that if this problem were solvable, it would mean that P=NP, and thus the exam had a mistake. I still remember that all those years later.

I had a similar feeling when I spent over an hour trying to solve a Rubik’s cube, memorizing the algorithms again and again until I did them automatically but still could not solve it. After I finally had enough, I checked online in realized that the cube was faulty! I guess my kids dropped it and some pieces fell off, and they put them back together in an unsolvable way. Again, the frustration also came with a lot of lessons and a deeper understanding of the problem.

And those are cases where the problem was genuinely impossible. The motto of my army unit was ‘anything is possible.’ We’d be asked to refrain from automatically shooting down ideas or suggestions, and consider things with the belief that a solution exists, just not a trivial one.

If You Can’t Fail, You Can’t Win

Now, I’m not claiming assigning impossible tasks regularly should be your new leadership tactic. I can imagine it would become quite frustrating. Nevertheless, there’s something very healthy in not succeeding at everything. When many tech leaders instinctively aim to have all their roadmaps and sprints successful and avoid any mistakes, I find that those who achieve the most ambitious goals regularly fail.

It’s good for teams that want to grow as fast as possible to face stretching tasks rather than always delivering 100% of what’s asked. It’s another example of healthy friction that I see in the top product-engineering teams. As a leader, think about how many things that your team has done in the past quarter or so could genuinely fail. Are you running a feature factory, or is there some healthy innovation and creativity involved?

If you’re not there, making positive progress is easy. Speak to your team about embracing healthy failures. Reduce some buffers from tasks (Parkinson’s law makes buffers just get longer with time). Talk to your Product peers about running some experiments. Hold intermissions/innovation weeks. Spice things up.