Learning To Learn From Failure … as an Experienced CTO

Andrew Weaver
October 6, 2023

“Success is stumbling from failure to failure without any loss of enthusiasm” – Winston Churchill

People who’ve made it to the top in their business, sport or career always seem to make success “relatively” straight forward when of course we all know – or at least those who tread a similar path will know – that’s it been far from easy to get there.

Whether you believe in Gladwell’s 10,000 hour rule or not, we know that success in any discipline is generally a mixture of talent, mindset, application and luck.

But perhaps the one consistent theme that runs through the story of all successful people is their ability to address failure as a learning channel and fundamental to helping you grow the skill set and the instinct to be a success in your chosen path, even if it might not feel like it at the time.

I was reminded of this at home recently when introduced for the first time in my life to the skipping rope!

Getting hit on the head by my Jump rope

Like many others one of my new year resolutions in 2023 was to stay fit and part of that plan included my first attempt at using a skipping or jump rope!  

“How hard would that be?” said I as I pressed “buy now” on Amazon. 
Oh dear, I could not have been more wrong.  

My first few attempts were not only a complete fail but almost always an embarrassing fail.

I was quickly thinking about returning the rope until my 12 year old son picks up the rope and goes straight into a boxers skip as if it were the most natural thing in the world (how many of us suffer similar humbling experiences with our kids?)

That’s all the motivation I needed to persevere.  

Fast forward and I was still absolutely terrible but each time I failed the rope hit my feet, legs or quite often, the back of my head, I felt more determined not to give up, to keep persevering and to watch another 2 hours of YouTube videos on skipping technique. 

So what??

Well this experience inspired this article.  

As the rope hit my head for what felt the Nth time this morning and I let out a small scream of frustration whilst resetting the rope again, I released that learning to jump rope has a lot of synergies to my life at work as a CTO.  

My working environment is (and TBH always has been) about constantly absorbing failures and learning from them… so instead of the rope hitting my head it might be some code failing a unit test for the fifth time, or a document you have spent all week writing being ripped to shreds by your executive team mates.   

What do we, as leaders, do in these times of failure; we stop, take stock of the feedback and quickly adapt based on the learning. As technology  leaders we have got to a place in our careers where we can do much of this naturally and instinctively, and therefore quickly.  We have found our own tools that allow us to remember the context of what we were trying to do, pick apart the feedback (be it from the unit test or the redline/comments in the doc) and then translate that into change or adaptation of what we were trying to do.  

If you’re like me then you still let out a small scream when something hits the buffers, but I have trained myself, through experience, where I can negotiate those negative emotions and small setbacks, transforming them into the energy and processes to move on with what I was trying to do.  

And hopefully muscle memory retains that experience and feedback for next time (though I do recommend sometimes making a note of particular incidents and solutions) to help you avoid or minimise the risk of something similar happening again. The British cycling team once achieved huge global success but making tiny adjustments and improvements they called ‘The Aggregation of Marginal Gains’ – a philosophy I aspire to achieving with my performance and that of my team. 

Personally I love a working environment which uses feedback loops and the ability to learn from mistakes and self improve.  I get a huge kick out of it now.  

I have also been very fortunate in my career to have great leaders and mentors who provided me the feedback and philosophy to take the hits but continue to move forward.  

The effective coaches never shied away from telling me the hard truths and to adopt the growth mindset.  

From past COO’s, CFO’s, NED’s to members of my past and current team, I have got to a place where I try to learn from everyone and everything around me.

Our responsibility as leaders

This then takes me to the role and responsibility we have as tech leaders or managers.  

If what I’ve said is important to you (and hopefully it is) and you find yourself talking to your teams about “failing fast”, “failing forward”, “resilience” etc.  It is your job to provide the systems, process and tools to enable your team with the feedback loops and confidence to learn and improve. 

It doesn’t really matter how big or mature your team may be, as a leader and manager of people we need to set them up to win.  This means that when they fail, we need to be there to help them get up, dusted off and in a position to move on.  

In very early start-ups when you can feel the breath of your colleague in the chair next to you this can be as simple as an arm around the shoulder and a quick round of pair programming.  

But there should be learning for you as well because when things do fail you may need to look at putting in more formal steps to help guide the process

Culture is Key

Create an environment and a culture where everyone feels safe to fail.  Now you have probably heard or read this hundreds of times, but what does it mean?  

Simply make sure your team knows that it’s OK to fail.  

Make sure they truly understand they are not going to get fired or a 10 minute rendition from the urban dictionary flying at them.  

Re-enforce to the team that failing is OK as long as it’s followed up with transparency, honesty and learning  

Culture starts at the top so you need to lead by example. Be open with the team when you fail and what kind of remedy and process you use to learn from it.

I will often publicly detail my failures in our Tech team meeting.  I go through my errors and what I did about it.  

This didn’t happen overnight. I used to think this would show me to be a weak leader but it’s actually the opposite and the team has always appreciated this element of my leadership. 

This is most evident when you get the team putting their hands up on mistakes and watching their teammates swarm the issue… no better feeling as a manager than seeing that swarm.

I also make a point to raise the other failures happening around the business.  I will talk to my team about situations that are happening that they may not be aware of and then show them what as a business we are doing (or did) to address a particular issue. I believe it is super important that your team has visibility of what’s happening elsewhere in the business, particularly if it could have a direct impact on their work and career.

Everything Needs Process

Like every techie I love process and these are 3 simple steps to help support a culture of how to manage the learning process from setbacks;

  1. Pull the Andon cord (https://www.sixsigmadaily.com/what-is-an-andon-cord/).  Create a virtual Andon cord.  Make it OK for the team to stop everyone working and get the help and support they need.  This could be as simple as a message in your team Slack or Teams channel, or a quick phone call to your manager, but raise the issue and get others to go and support the person that needs help
  1. Review incidents and have an incident process.  For many start-ups you will think this is overkill. But by having a very simple process that allows incidents to be managed and communicated will mean your team have a support system to fix an issue and it will mean that management have a way of getting updates on an issue, without sitting on top of the engineer that is trying to fix something
  1. Use the 5 whys process after an issue has occurred (https://buffer.com/resources/5-whys-process/).  It does not matter if the issue was a failure in production, or a problem with a process that creates lots of manual work, running an open and honest 5 whys session will always help you discover some of the underlying issues.  I love this process and I am a huge champion of it, but that does not mean I want to fix everything that we uncover.  Typically at the end of the a 5 whys session, we only look to ‘fix’ 30-40% of what we discover.  This may not sound a lot, but the difference it makes and the ongoing gains you get is huge.

Final thoughts   

Building the culture and resilience where it is OK to fail for you and your team is hard and it takes time.  

Failing is essentially a real time training that helps you become more resilient and effective as a team, but like all training it’s an ongoing process and you will have many ups and downs as a leader to understand the nuances of how, when and where the manage failure.

From my experience the key takeaways …

  1. Be open about failures
  2. Put in systems and process to be the framework as failures occur
  3. Be the support system for your team to learn and move forward
  4. Find your own support system, so you can better help your team
  5. Find a coach for you and key employees, who can provide a sounding board for how to manage this process.

Next for me, is to watch another 2 hours of YouTube videos on jump rope ?

Original Article Written by Sanjay Mistry, CTO and Leadership Coach

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