Jacob Kaplan-Moss


Make Failure A (Safe) Option

A mistake I made a few times earlier in my career was withholding opportunities from people on my team until I felt they were “ready”. Once, I had someone on my team, who I’ll call E—, who very much wanted to move into management. E— asked to take over our team’s budget planning. In many ways it was a perfect delegation opportunity: it was one of my “toys”; it would get them time with our engineering leadership team and with our CFO; it was a way to practice some of the nuts and bolts of management. But I was worried in particular about the CFO: they didn’t handle disagreement particularly well, and neither did E—, so I worried they’d clash. Worried about failure, I said no.

In retrospect, that was a mistake. Giving E— an opportunity to stretch their skills was exactly what they needed. And I had a great relationship with the CFO, so even if things went sideways I could always step in. So failure was low-consequence, and E— could have learned a ton from that failure. Failure is a great teacher: how many of your big failures turned into key lessons for your career? I know many of my biggest moments of growth came shortly after I messed up.

Your gut instinct is probably to wait to delegate some work until you’re fully confident that the person can handle it. This is often a mistake. Recall that one of the purposes of delegation is to help the delegate grow; in that context, you need to let them do work that might be on the edge of their current abilities.

Make failure safe …

So, instead of withholding a delegation opportunity from someone because they might fail, you should instead create a situation where failure will be safe.

There are two parts to creating a situation where failure is safe:

  1. You need to have created trust on your team, and built an environment high in psychological safety. Building trust and creating a safe team is another topic entirely, so for now just this: build trust first, then delegate.

  2. Consider the specific delegation situation, and set things up to allow for failure. Understand the consequences of a failure, and ensure that they’re low. Some consequences are OK – failure is a great teacher – but they should be minor. They should also be temporary. If failure at the work would permanently harm their standing at the company, or be reflected in the size of their bonus or on a performance review, it’s not a great candidate for delegation.

One exception: sometimes you’ll run across high-consequence, risky projects that are nevertheless ideal delegation opportunities (maybe they’re exactly the kind of work the person wants to be doing; maybe they’re very risky but with massive upside; etc.) In these cases, I think it’s OK to ask as long as you’re very clear about the risk and prepared to hear a “no”. I’ll say something like, “this is a bad situation: you might do everything right and still fail. Do you still want to try?”

Overall, you’re trying to create a situation where they own the success, but you own the failure.

… and let failure happen

The last part: once you’ve created a situation where failure is safe … you need to be prepared to let failure happen.

Obviously you’re not hoping for failure, so of course you’ll try as hard as you can to set your delegate up for success. (The next couple of posts in this series will cover how to do this.) But, once you’ve delegated the work it’s time to step back and let the delegate drive. The balance here is a bit delicate: you should still give feedback, and offer guidance if asked1, but you should try to avoid taking control unless it’s truly unavoidable. In general, it’s better to err on the side of “too hands-off” than to pull a fake-out delegation where you pretend to delegate but continue to pull strings.

It can be difficult to watch someone struggle, but try to resist the urge to step in. Again, failure is a wonderful teacher. If you’ve managed the situation well, your delegate can get all the learning that a risky situation provides, without any serious consequences for failure. It’s hard to pull this off, but fantastic when you do.

  1. I once had a manager who would delegate or assign work, and then absolutely refuse to give me advice even if I asked. That’s taking “hands-off” to a ridiculous extreme; don’t do that. ↩︎