Why Fail Fast Culture Doesn’t Fly In Most Places

What you can do instead to truly drive value!

Jul 02, 2025

How many times have you heard that you should fail faster?

You’ve probably stumbled upon several variations of the same message.

The faster you fail, the sooner you succeed.

Yet, somehow, that doesn’t fly with most companies.

Linear’s CEO, Karri, gave a keynote at Config about why everything feels so forgettable these days. He covered how the "move fast and break things" mentality killed craft in software. This is worth reading if you've ever felt torn between shipping fast and building something you're proud of.

→ Read here"

Let’s have a sincere conversation about it.

Nobody Likes Failing

If we’re honest with ourselves, failing is one of the things we hate the most.

Failure tastes bitter, we all know that.

How did you feel when you failed an exam as a kid?
In college, how did you feel when a presentation went south?
How do you fail after you fail an interview?

None of the above gives us pleasure.

What makes us think that failing faster will be welcome in business?

I have worked with several dozen organizations, none of which would chase failures. They’d do everything they could to avoid them.

The problem is that talking about failures creates friction before progressing. If there’s something I learned after playing this game for more than 17+ years, it’s that avoiding failures is what people want, not running toward them.

Nobody wants to:

Ship features that fail to delight users
Create products nobody uses
Deliver half-backed solutions

Yet, the above will happen if you fail to learn fast enough.

It’s Not About Failing. It’s About Learning.

The fail fast message aims to accelerate learning, which makes sense. But if you keep talking about failing faster, you will have little chance of making that happen.

The more conservative the culture, the less they want to hear about failures.

I’ve been working in Germany for several years and received considerable support when discussing de-risking ideas. I often use the following approach.

To ensure the idea <X> flies, we need to reduce the risks we have:

Desirability: How do we ensure customers want that?
Viability: How do we collect business value?
Feasibility: How can we deliver it with the constraints we have?
Usability: How do we know users will figure out how to interact with it?

From there, I recommend running experiments to accelerate our learning and reduce the risk of our product ideas.

In Germany, I gain support when I present experiments as part of a process because it makes them easier to understand. In other places, I present them as iterations.

How Do You Accelerate Learning?

First, you need to know what you don’t know.

For example, you probably don’t know if customers need what you aim to build. You may assume you know, but you lack evidence. That’s the starting point.

Name your assumptions. Then, prioritize those that, when proven wrong, your idea becomes irrelevant. From there, run product experiments.

You can start simple:

Survey: Sent out a survey to understand the direction
Interview: Talk to a few customers to learn what matters to them
Dog Food: Use your product to feel the pain
Prototype: Run usability sessions to evaluate your solution

With the above, you reduce the chances of creating something nobody needs. Yet, you need to remain humble to drop ideas that don’t fly. Funny enough, that’s the concept of fail fast, but you will only gain support once you broaden the context.

How Do You Ship Value Beyond Features?

Features are means to an end.

Your objective is to ship value, not features.

With that in mind, you may need to measure the results of features you create continuously.

Here’s what not to do:

Invest months building something without knowing how that drives value
Ship features and ignore results
Release features to everyone at once

The above reduces the odds of thriving and maximizes the chances of creating nonsense.

If you’re serious about creating value, you can benefit from:

Becoming your user. The more you use your product, the more you understand what helps and annoys users.
Release gradually. Start small, and then release to your whole audience.
Try out different solutions. Create multiple features to address the same problem, then compare the results.

Such practices will amplify your chances of success.

An important question: When was the last time you retired a feature?

A great product is the one you have nothing to remove. Not the one you have nothing to add.

Key Takeaways

People want to avoid failures as much as possible. You will have a hard time driving a fail-fast culture.
Focusing on learning to reduce the odds of unbearable failures is your best chance to create space to de-risk product ideas.
Continuously reflect on what you don’t know, so you run product experiments to uncover your blind spots.
Accelerating learning is what enables you to create real value faster.