Member preview

How Will You Fail Here?

The Best Interview Question I’ve Been Asked…So Far.

I was recently asked an unusual question during an interview:

“How will you fail here?”

Before opening my mouth, I paused for a few seconds.

Plenty of companies claim they support “failing fast” and learning from failure, but how many actually provide ways in which people can productively fumble?

Thinking back to my past experience, my answer became pretty clear.

I admitted that, at times, I may be a little too eager to execute on ideas and my impatience could end up getting the best of me.

Now I know what you’re thinking:

“Pssh, this is a non-answer! You’re just humblebragging.”

This really can be a weakness of mine.

In an attempt to overcome past perfectionism, I overcorrected and now have a tiny tendency to act before having a fully-developed plan.

Depending on the environment, this can either be an even bigger weakness, or it can act as a strength.

Example 1: Planning the launch of a new book

Okay, so I’m not finished with my first book yet, but I will be eventually. When that time comes, I’ll have to navigate the slippery slopes of publishing and launching a book.

If I were to simply write it and put it out there without having a plan, do you honestly think anyone would read it?

Hell no. It would float out there in the endless void that is the Internet with all of the other half-assed books. In this case, having a detailed plan before, during, and after publishing is key if you want people to actually read your book.

Example 2: Consulting a client who wants to launch an app

We all know someone with an app idea.

The thing is, 99% of those people will never do anything about it. They will let paralysis-by-analysis sink in and someone else will end up launching their app into the world.

In this case, a bias towards action can act as a blowtorch that sculpts that initial app idea into a functioning app — ideally, one that people will actually use.


As you can see in the first scenario, my eagerness to execute would mean ultimate failure for my book. Knowing this, I can approach this project with a little more finesse while creating a comprehensive plan.

However, when it comes to the app idea, getting something out in the world as soon as possible makes all of the difference. In fact, I don’t even need to write a single line of code in order to design a prototype to test with real people.

Thinking about failure is pointless unless you ground it in the world around you. That’s why we need to stop having abstract conversations about “failing fast” and start explaining how we will fail productively.


William Frazier is a designer, writer, founder, and productive fumbler who blogs about making ideas happen at The Imperfectionist. He’s also on Twitter.