Cindy Alvarez

If you fail to plan to fail, you plan to fail

"If you fail to plan, you plan to fail."   - Benjamin Franklin

If Ben Franklin were running a company today, I think he'd have added a couple words to his quote.

He was a pretty smart guy, and I'm sure he'd recognize that nowadays, planning is not enough.

Planning alone doesn't prevent mistakes or reduce risk -- not in an environment where technology, customer capabilities, customer expectations, and your competition are all constantly changing.

What saves your bacon when everything keeps changing around you, is your ability to recover and adapt. Your ability, in other words, to fail, quickly learn from that experience, adapt, and keep going.

How do teams build that ability to fail-and-recover? By planning small, low-stress opportunities to fail.

Managers, you need to be letting your teams make mistakes. Control the stakes and the resources spent, sure. But don't step in and prevent small failures from happening. Don't be a helicopter boss.

A few weeks ago, I was working with a small team to explore a problem area in our product. We started by digging into the problem, forming hypotheses, and devising an MVP to test that hypothesis. And there I gave them a 2-week deadline and stepped away (conveniently, I had some travel).

A few days into my absence, I realized the team had almost certainly been overly ambitious in the scope of what they wanted to do (all 4 of them were committed to other projects so I knew they wouldn't have much time to dedicate to this one). I almost started firing off messages to point this out and nudge them to rethink scope -- and then I stopped.

At the end of the two weeks, they hadn't finished what they planned to. Hadn't come close, even. But it was a really good opportunity to ask,"Why not?" I emphasized, "I'm not looking to blame anyone, but I'm curious why we didn't come close to what we wanted to get done."

Didn't account for competing priorities. Didn't plan out dependencies. And now that they thought of it, their MVP wasn't actually all that 'M'. Should've thought smaller and nimbler.

I didn't have to provide those answers. And it wouldn't have done much good if I had. Making the mistakes yourself is when they stick.

Somewhat inadvertently, I'd planned a failure -- a small, memorable one that hopefully will innoculate us against bigger time-wastes.