The Art of Deliberate Mistakes

It sounds like a contradiction to encourage others to make mistakes, doesn’t it? But if your company doesn’t allow others to do so, how are they going to challenge their assumptions about what works or what could be improved?

No one criticizes a child for falling off a bike when it learns to cycle. It would be foolish to berate someone learning to swim if they couldn’t do perfect laps every time. So, what’s the real fear of making mistakes in  your business? Or how can you design mistakes that show you what you need to see?

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Deliberate Mistakes – Two Kinds

Why make deliberate mistakes?

Think of it as an experiment where you expect to fail and it won’t be worth its cost.

It’s designed to challenge your assumptions. This is very different than most business experiments, which are designed to confirm your assumptions.

Here is an example with email campaigns.

  • Right Mistake – Let’s say you decide to test your email delivery. You send 50% with many graphics and the other in plain text. Which performed best? Then you decide to change the frequency to every day, or maybe twice a day, or three times! You keep refining the process, tinkering here and there until you get the best results. But, you will make mistakes, upset some people, and have a few failure along the way. But what you learn, you can apply to the business.
  • Wrong Mistake – You decide to send emails to people who haven’t signed to your list, or make it very difficult for them to unsubscribe. And even when they do unsubscribe, the ‘fine print’ they agreed to allows you to share their details elsewhere.

Here’s another example about tapping into outside resources you don’t have.

  • Right Mistake – An IT company runs a contest (Google do this quite often) to see who can complete a very difficult task, for example, get a computer on the moon. This allows them to tap into engineers all over the planet. Even if the task fails, they get to see many prototypes, which will spark new ideas in their own team.
  • Wrong Mistake – You enter into a new market to get first mover advantage. The entry costs are huge but you hope it will pay off. It may be smarter to let others test the waters first, see what goes wrong for them, and then come in with a better product. Facebook and Twitter are good examples of this. Neither were first to market but learnt from those who went before… and then struck.

You get the idea, right?

Let’s take another area: design.

  • Microsoft tried to get into Web TV years ago and failed. Was that a mistake? Apple has done the same recently and now gets the kudos. Is the problem the technology, timing or brand perception?
  • Cisco had a runaway success with the Flip cameras… but then closed it down.
  • Apple charged developers a fee to submit their apps to iTunes. Is that a mistake?

It’s hard to know as the circumstances are different for all companies. So, how does this apply to you?

Deliberate Mistakes – Risk and Rewards

One way to get some objectivity about this is to look at risks (what might happen if it goes wrong) versus the rewards in your company.

Ask yourself:

  • Emotional Environment – Am I encouraging others to make mistakes? When they do, what’s my response. Will they make the same mistake again?
  • Stagnation – What’s the risk if we never take a chance? Does the company stagnate?
  • Capital Expenditure – How much am I willing to spend on a new mistake? What’s the hidden cost of not taking risks?

Deliberate Mistakes – Examples, Case Studies, and Best Practices

One of the difficulties I have as a consultant is when I present a new idea (really innovate) and the client says, ‘can you show me a case study of where this worked before?’

It’s a valid question… to a point.

What underlies this may be a fear of protecting oneself and looking for assurances that it can’t fail.

Sometimes there are no precedents. It’s all new territory. Look at Social Media. Where’s the ROI in a Facebook page? It might be there but it’s very hard to analyze as the discipline is so new.


There are some very good reasons to encourage others to make mistakes, not just paying lip service to it. While we develop our careers carefully avoiding making mistakes (or having them noticed), by playing safe all the time, your thinking stagnates. You no longer challenge yourself or your team. In addition, the feedback you get does not challenge what you already know, so you keep making the same mistakes 🙂

How do challenge yourself to make new mistakes?

What contingencies do you put in place or is that under-mining the process?