Is failure the best teacher?

Matt Mower
Activate Capital
Published in
5 min readJan 13, 2017
Photo by Gareth Williams on Flickr

Meeting a lot of people with a strong desire to change the world, either personally or through their business, I am convinced that everyone who wants to achieve anything of significance has a lot to learn. When you are doing something challenging, it is almost certain there’s stuff you don’t know how to do well yet.

What is the best way to learn it?

I’ve known people who have had success, sometimes quite considerable success or multiple successes, and then been shocked to fail in a big way. Continued success was… expected. The conclusion I have drawn is that success teaches a very limited amount, and can often be treated uncritically and this, in turn, can blind us to what is really going on around us.

Thinking about success in strategic terms you create goals, perhaps even SMART goals, and decide which tactics in the short, medium, and long term will advance you towards your goals. But how do you know whether you are on course or not? Deri Llewellyn-Davies — a strategy consultant from whom I have learned a lot — places a strong emphasis on the value of making strategy measurable. His “Strategy on a Page” system is designed to keep the measurement of strategy front & centre in the attention of business leaders.

Some people worry that the numbers make things too ‘mechanistic’, like they will end up taking control. But it’s worth thinking about the numbers measuring your strategy, as sensors inside a machine: they tell you about how it is operating, too fast, too slow, too hot, and so on. But they don’t control it. What’s important about the numbers is what they tell you about reality. Especially when they are telling you that reality is not like you hoped or expected it would be!

However, it wasn’t until I listened to Matthew Syed’s book ‘Black Box Thinking’ (from Audible, brilliantly narrated by Simon Slater) that I began to fully appreciate the role & value of failure, and how we respond to failure, in what we do.

Now, if your goal is not very challenging then… you succeed. Hooray! But it’s probably not a very satisfying success. On the other hand, if your goal is truly challenging then it’s quite likely you’re going to experience failure in some form. Whether & how you learn from that experience of failure is critical to what happens next.

At the start of Syed’s book he contrasts two industries with a very different response to failure: medicine & airlines. When an aircraft crashes, an independent investigations team are quickly on the scene looking for the eponymous black box flight recorders, so they can figure out what happened. Airlines encourage their staff to share their mistakes, openly. High profile crash investigations have led to significant changes in aircraft design and flight operations. Because of this open approach to failure over the years, the number of serious incidents and deaths has dropped so drastically that, in 2015, there were only 4 fatal crashes in over 36 million take-offs.

On the other hand the medical industry, as Syed describes in painful detail, tend to hide and obfuscate their mistakes. Not in a conscious effort to hide the truth, but because of a totally different response to failure. Doctors are expected to be right all the time, and their reputation and career may well depend on them being right. They have a lot at stake. Further, when they fail and injure or kill a patient, it is personally very painful to them. The combination of reputation risk & pain leads to a strong experience of cognitive dissonance, that can make it almost impossible to own up to a mistake. And where there is no admission of failure there can be no learning.

The result is an estimated 7,500 people per year dying in English hospitals due to avoidable medical error. This is equivalent to a Jumbo jet crashing — with the loss of all passengers — every three weeks! But where are the black boxes in hospitals?

Taking a less extreme example: many years ago I worked alongside a salesman in an enterprise software company. For almost a year I watched him make cold calls with little or no success. However, as a sales professional with a great reputation, he kept plugging away. Until one day he simply wasn’t there any more.

When his replacement arrived I’d expected him to start making calls just like his predecessor. Instead, he said “There’s something wrong here,” and we spent some time analysing our proposition top-to-bottom and realised it was fatally flawed. It would never work as it was constructed. That was my first experience of strategic sales & value proposition analysis and a real moment of learning from failure. In fact it led to both of us leaving the company shortly thereafter.

This demonstrates the point: failure taught us something very important about our value proposition and our chances of success. It also illustrates that we had to be open to the failure, to accept it, in order to have the opportunity to learn from it.

Returning to your strategy as a business owner, if you cannot accept that the tactics you are using are not delivering the results you are looking for, then you will never progress to the tactics that will. I’ve experienced this myself in my own resistance to measuring some things that I am not confident about. By not measuring I can “fudge” how well I am doing rather than facing the pain of failure.

This is why it is so important to have an outside perspective on your business, a trusted advisor to help you keep yourself honest and where you can own up to failures in a safe space, take your licks, learn your lessons, and move on to better tactics.

I think failure is the best teacher, but we have to be open to the learning it holds for us. If you are a business owner I would love to hear what you think. When have you failed, and what did you learn from it?

(My thanks to Paolo Valdemarin & Doug Shaw for their help editing this article and for their many suggestions that improved it).

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