Top tips and a practical guide to handling failure and mistakes

Hit Leader Hass Culture, Leadership Leave a Comment

When I was young my parents would always say – you are so clever, you are so smart etc. Whilst I felt it was encouraging it made me feel like I could not fail. In fact, I was afraid of failure. I was afraid that if I tripped up and made a mistake that my identity of being smart or clever would no longer be mine and I would be left with plain old me. I had originally got into medical school and my predicted grades were above the minimum requirement – yet I failed to get in because I got a B in biology instead of an A. I failed to get in and I felt absolutely shattered with no idea what I would do, or how I could get back up on my feet. I felt like – what’s the point? I didn’t want to do anything else, I wanted to give up. Fortunately, I was given an opportunity to study Medical Genetics instead. I had a great university experience, met some great people and came to a realisation that medicine actually wasn’t for me. That’s what lead me to study Computer Science and getting my MSc. Failing to get into medicine lead to me to where I am now – I wouldn’t be in a job I love without that failure.

We can all base our identities in success and can feel trapped and paralysed by the fear of failure. We are a manager who has done great things – how will we be perceived if we make a mistake? Who will we be if we fail? Failure is holding us hostage and stops us from taking a risk, from putting ourselves out there and from growth. Often we when we do fail, we focus on the fact that we have failed, that we are a failure rather than anything else. Nothing else matters to us except the fact that we have failed. When we stop to focus in this way, we stop moving forward, we are blinded to the vital information that failure actually carries.

Failure is something that a lot of us have been conditioned to avoid through the expectations that our cultures and societies put on us and the way that our parents raised us. I think this is especially relevant to women, in that our societies and cultures seem to put a large amount of pressure on women to be perfect and to avoid risk and failure. Here is a great TED talk that goes into more detail on this issue:

In an interview I heard recently with Sarah Blakely she described a memory of her dad asking her and her siblings every day after school, “how have you failed today?”. I think this is so refreshing. Her dad was telling her to bring her failures to the light, identify her mistakes because she will have made them and that is OK. Identifying your mistakes and failures and admitting them is only the first step but it is a crucial one that can often take a lot of courage to reach – but once you get there you will really see the fruits of your labour as you really analyse the data around your failure.

Self-compassion: I have my permission to fail

You need to give yourself room to fail and when you do forgive yourself for it. You need to adopt a mindset that says that mistakes and failure are OK – you are only human. Yes, humans can do amazing things but we are not perfect. We can never be perfect and that is OK because you are in the same boat as everyone else.

This research conducted by Kristin Neff, an associate professor in the University of Texas’s department of educational psychology, found that people who practice self-compassion recover more quickly from failure and are more likely to try new things. Forgiving yourself and owning your humanity is the big step in being adept at bouncing back from failure and giving you the confidence to get up and try again.

“Failure is in the eye of the beholder,” says Carol Dweck, Lewis and Virginia Eaton Professor of Psychology at Stanford University and the Author of Mindset: How You Can Fulfil Your Potential. “What for one person is a humiliating failure will be a temporary setback for someone else. Successful people often consider these challenges as steps along the way.”

Failure IS compatible with success. In fact, in a lot of cases, it is a driving force for success. Some of the best CEOs and leaders of our day have faced failure at some point and that failure propelled them to their great heights.

“Among the high net worth individuals surveyed for this report, 59% say that they have experienced career failure, which might include failure to get a promotion or losing a job, while a similar proportion have experienced failure with their investments”, courtesy of Barclays.

Research conducted by Kristin Neff, an associate professor in the University of Texas’s department of educational psychology, found that people who practice self-compassion recover more quickly from failure and are more likely to try new things.

Compassion: You have my permission to fail

Your team will also need to know that it is OK for them to fail – that they are safe to do so otherwise why would they try in the first place? Why would they take any kind of risk that might produce great success for you and your project if they didn’t feel safe to try and fail? Lead by example. Call out your own mistakes and show them how it is dealt with in a healthy way. Encourage the team to bring up their mistakes and discuss them in a valuable and constructive way. Don’t make it about them, make it about the failure or mistake – take them out of the equation. Make it about the team – you win as a team and you fail as a team.

“You must reward people for failing,” says Astro Teller, the scientist behind Google’s ‘moonshot factory’, where engineers can test out their most audacious ideas without fear of reprisals. “If not, they won’t take risks and make breakthroughs. If you don’t reward failure, people will hang on to a doomed idea for fear of the consequences. That wastes time and saps an organisation’s spirit.”

Based on this article, in 2016 Tupperware (a home products business), started using and spreading the message ‘failure is beneficial’ in their workforce. They saw higher levels of self-confidence, increased productivity, innovation levels and degrees of entrepreneurship, greater optimism about life and the future, and increased the likelihood of overcoming workplace challenges. They also saw financial benefits to both individuals and the business overall: those same employees recruited on average 27% more sales representatives and achieved 22% higher sales.

Retrospectives, as described here, are a good tool for bringing in a healthy failure mindset to your teams.

My process around addressing and using failure

To address your failures and mistakes in a healthy way you need to do two things:
1. Identify and Analyse
2. Pivot

Identify and Analyse

Think of everything you do as a delivery mission. You have a starting point, a path you take and the desired destination. The path you take might take you to an undesired destination but if you really think about it you can retrace your steps and make sure you don’t take that path again. Was there anything about this particular wrong path that could have warned you but you didn’t pay attention to? Let’s imagine it had a sign saying “DO NOT ENTER”. You took that path and you failed to get to your desired destination. This destination isn’t quite what you were hoping for, it doesn’t have any of the houses you were expecting to deliver to. Now you have some information to make sure you don’t take a path that says “DO NOT ENTER” again, you know the consequences of taking that road and you know that although the correct path is still out there, the decision you need to make is narrower.

This little illustration tells us we need to identify what went wrong and ask why it was a failure? What was the impact? How did the impact of your failure differ from the desired result? What can you do better next time? How can you prevent this failure happening in the future?

Don’t just rely on your views, ask other people. Was anyone impacted by this? Ask them about it. What did you do wrong? How did it impact them? How did it make them feel? What can you do better? If you hurt someone, you let them down, then asking them these kinds of questions can show them you are looking to improve, do things better and consider their insight valuable in doing that. If we take the analogy of the delivery mission again – you may have not spotted what you did wrong on your journey. However, there will be onlookers, or there may have been people you were leading that have spotted the mistakes you make.


OK, you have identified your mistake and analysed it – you need to now make a decision. The first decision you will need to make is to take a step forward – the decision to continue trying. This is often the most difficult decision because it is easy to give up but know that in making another attempt at this – you are actually more likely to succeed and less likely to fail. This is where the self-compassion comes into play that we talked about earlier. You need to give yourself permission to make mistakes and fail.

Once you have made a decision to move forward you need to choose a direction to move forward in. You now have more information under your belt to make a more informed decision on which is the best way to go. You need to be confident in your choice and at the same time be comfortable with uncertainty and know you may need to come back to the drawing board – but again with more information. In-decision can be paralysing and detrimental in leadership positions. Be informed, be careful, be open to uncertainty but make a decision. Before you decide on a direction it’s useful to articulate why you are choosing a particular route over other options and what the consequences could be if you choose this direction over others.

It’s also worth noting here that if the best decision is to kill the particular thing you are working on or doing – e.g if it is a project – then that is a valid decision. That isn’t you failing or giving up. It is a recognition that there is no better alternative. Sometimes, scrapping a project or product is the best thing you can do. Check out this list of discontinued Google products and services – would you say Google have failed or given up by scrapping those ideas?

Logging my failures

One thing I try to do to maintain a healthy mindset for mistakes and failures is to take a regular log of what I have done wrong and what I could have done better in my work. You can see the entries to date here.


Failure is feedback. Feedback points to a new way forward. Failure and mistakes are compatible with success and in most cases are required to succeed. Failure is just an opportunity to grow and to learn, it isn’t the end of the road. To deal with failure in a healthy way you need to do the following:

  1. Give yourself the permission to fail and make mistakes – you are only human, you will make mistakes and fail from time to time but it isn’t the end of the road.
  2. Give others the permission to fail and make mistakes – lead by example, show them how you deal with failure. If your team know they can fail safely they will be much more likely to succeed.
  3. Identify and analyse your failures and mistakes – why was it a failure? What was the impact? How did the impact of your failure differ from the desired result? What can you do better next time? How can you prevent this failure happening in the future? Get feedback from others.
  4. Pivot – choose a direction and move forward or stop moving at all. Be decisive.
  5. Log your failures. Keep a diary and it will help you establish a good habit around learning from your failures and mistakes.

If you get a chance, read “Mindset: How You Can Fulfil Your Potential” by Dr Carol Dweck. It can really help you establish a healthy mindset for dealing with failure and life in general. Check it out on Amazon UK / Amazon US.

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