How To “Fail Fast And Often” – The Iterative Mindset For Success

Lissa
Product Coalition
Published in
4 min readFeb 19, 2021

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Fail Fast, Fail Often — this phrase is often used as a mantra. It's a manifest of modern agile philosophy, originated from Silicon Valley's vibrant and fast paced start-up world. Big successful companies embody and exemplify the meaning by having it as an internal motto such as Facebook's "move fast and break things". It all sounds easy - Take quick action instead of talking, fail, learn from it, then go on and repeat. Make your cycles as short as possible to boost your learning rate.

But when it comes to executing I realised that these phrases are not actionable at all. How do I actually implement this mantra in our team? How do I become more daring and bold?

In this post, I would like to share four actionable learnings that worked well for me.

Realise most of your decisions are two-way doors

In a letter addressed to shareholders, Amazon founder Jeff Bezos divides decisions into two different types:

  • One-way doors: Decisions that are hard to reverse. Once you've walked through, you can't turn around and come back. With one-way door decisions, you want to be cautious, gain high certainty and take your time.
  • Two-way doors: Decisions that are easy to reverse. Once you walk through and don't like the other side, you can come back. For two-way door decisions, the fastest way of finding out the answer is to open the damn door.

In order to move fast, your first task is to find out what type of decision is in front of you. Don't let caution creep in and get paralysed by thinking everything is a one-way door - the vast majority of decisions in our lives are revertible. You have a two-way door in front of you? Perfect, open it and see what's behind!

Frame it as an experiment

One way to keep the ball rolling is to think of your decision as an experiment. The wording is important here, because framing it as an experiment allows you to make mistakes. An experiment tests a hypothesis that formulates an expectation about how something works. The outcome can either support or disprove the hypothesis. In other words: Experiments are expected to proof you wrong. As one of the 20th century’s most influential philosophers of science, Karl Popper, once said:

“The universe does not tell us when we are right, only when we are wrong”.

In an experiment, the worst that can happen is that your hypothesis gets invalidated and you gain valuable insights. That doesn’t sound bad at all, does it?

Ask for objections, not opinions

Decision aligning in a team is often done in a somewhat democratic style where you present your view and ask for opinions. But here lies yet another challenge: If the team is passionate about the project, everyone has an opinion. And everyone is eager to share it. This bears the risk of discussing too much without coming to the decision itself and hinders you from learning fast.

Again a slight twist in the wording can lead to a different mindset: Instead of asking for opinions, make a proposal and ask for objections. This way, a lengthly discussion will only take place if someone has strong feelings against it and the goal to make a decision is clear. Keep in mind though that the decision is not your sole responsibility - you are proposing a solution. In other words, you still need to give others the chance to veto. The only thing you’re doing is to accelerate the process by cutting the step where everyone bursts out their personal statements without the goal in mind.

Do retrospectives to ensure learning

Only failing fast and often brings you nowhere. Ensure to learn from your failures or you just find yourself acting reckless. Holding regular retrospectives helps you to keep learning from your mistakes and drives you towards constant improvement.

The word "retrospective" comes from the Latin retrospectare which means to “look back”. It is used to describe a session where you reflect on past events and draw learnings to incorporate improvements. There are many ways to do a retrospective such as the 3L format (liked, learned, lacked) or simply asking what went well and what didn’t. Either way, the important part is to identify successes as well as improvements and to integrate them into your future doing.

The real aim of "fail fast, fail often" is to be iterative. To achieve success by failing, you must reserve some time to reflect about why you failed and what to do better next time.

By making use of these four strategies, I started becoming bolder in making decisions. They helped me in my daily doing to take decisions faster and with more confidence. This accelerated my learning and I hope for you to experience the same.

So, here is a recap for your memory:

  1. Most decisions are revertible, so go for it
  2. Decisions are experiments that are expected to proof you wrong
  3. Make a proposal and ask for objections
  4. Do regular retrospectives to learn from your failures

Once you know how to fail properly, you also understand the positive side of failing. You start becoming less afraid of it and discover the wonderful thrill to open a door not knowing what will be behind. Your curios eyes sparkle, your heartbeat begins to raise a bit and you can’t wait to open another door again!

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Currently: Chief of Staff to the CEO at a software scale up. I fall for good wine, good food and interesting conversations :)