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Lessons from Leaders: Learning from Failure

In our second article from Lessons from Leaders series, we ask some of our team what is the most valuable lesson they’ve learned from failure.

As champions of Agile, we encourage teams to become more comfortable with failure as they test hypotheses, learn new information and iterate on their ideas.

Nathan Nelson – Partner, Managing Director, USA

What I’ve learned over the last 20 years is that there are themes and patterns on what’s been done before. However, every situation has its own unique variables. Thus, getting too prescriptive and being unwilling to accept new information during the process will generally set you up for a less than optimal outcome. I don’t really use the word “fail” unless it’s a situation that I didn’t learn anything from….which is very rare.

Alan Trivedi – Principal, USA

Stories are what motivate and inspire people to try new ways of working. Stories are formed from observations and reflections. I have learned that creating stories based on qualitative and quantitative approaches become catalysts for teams to test and learn more.

For example, interviews with leaders and teams that have demonstrated success by testing and learning create the FOMO (Fear of Missing Out) narrative that inspires others to take on more risk. Observations (like using behaviour markers) help teams understand how their behaviours drive the results they desire. Similarly, retrospectives enable teams to improve in shorter iterations and quickly change what is not working.

These are only some ways to codify experiences in a way that encourages more test and learn behaviours. Simon Sinek also sheds some light on moving away from the term “Fail” and using the term “Fall.”

I especially like this as failing is something we experience in hindsight and cannot be changed in the past, whereas falling happens in real-time, and we can get right back up. Teams that learn to codify their experiences are able to quickly support each other in getting back up in real-time.

Steven Walton – Principal, Australia

I rarely talk about “failures” in Agile, I talk about “learnings”. My biggest “learning” in Agile coaching reinforced to me that everyone has a perspective, including those not directly involved in the work. From this point, I have adopted a more 360-degree view of stakeholder management. Those who I see being truly successful, manage others up, down and to the sides.

Ghaleb El Masri – Managing Director, Canada

I’ve learned to communicate often and in a concise manner. Some failures have come purely about from expectation management – everyone is busy, and if you don’t communicate consistently and remind them what is happening and where it is going, they can easily forget and develop expectations of their own, that are different from reality, even if the reality is by most measures proceeding successfully.

Laura Scott – Project Lead, Australia

I have an example where recently we ran an agile simulation which didn’t resonate with the client as well as we had of hoped, we went back to the key stakeholder and tested another approach with them for the next team, made some simple tweaks and gave the next team immediate benefit from the simulation.

It was a really simple change of topic of simulation but changed the whole mindset of the team and they still reflect on it today. After this small change but big learning we tested everything with the key stakeholder prior to roll out, not from a micromanaging perspective but a test and learn, iterate and improve perspective and we had a really successful outcome.

Andy Koh – Project Lead, Singapore

The most valuable lesson is realising that failure needs to be concluded with a conscious decision to move on. One way I codified it is to ask myself a series of reflective questions:

1. What is the impact of the failure?
2. What do I need to learn from it?
3. Is there anything I want to do about it, now or later?

Going through this mental exercise reduces the emotional barriers that impede progress and integrates learnings from the failure.

To give an example, last year I wanted to lose weight by exercising more. I started to wake up an hour earlier every day to either jog or do some static exercises. After around two weeks I felt like it was not working. What is the impact of the failure? I felt so tired after each exercise session that I became less effective in my work during the day, plus I was not losing any weight and felt bad generally.

What do I need to learn from it? Maybe I cannot exercise every day. Maybe it is not working because I am more of an evening person, and I can feel tired and ineffective without impact to my work in the evenings. Maybe it takes longer than two weeks to lose weight.

Is there anything I want to do about it, now or later? Let me try to change things around and see if it works next week. Exercise after work in the evenings every other day and maintain it for two months.

After the two months, I regained work effectiveness, felt happier and lost three kilograms.

Kayla Cartwright – Project Lead, USA

I started my career as a classroom teacher, where the learning curve was steep and it felt like I was failing frequently. The biggest lessons I have found in failure, from that point on, are:

1. If you use data, you can be more objective and specific about the extent to which you have “failed” and you can better identify the gaps you need to address.

2. The only true failure comes if you do not pause and reflect on what actions and BELIEFS led to the undesirable outcome; if you DO take the time to reflect and reply, then the outcome is in fact not a failure, but a lesson.

Given that my classroom was in rural North Carolina (in “the south” in the US), this learning was codified for me by this southern expression:

“Everything in life is either a blessin’ or a lesson”.

I take this with me each day.


Sławomir Kozioł – Project Lead, Poland

For Agile practitioners, testing and learning is second nature. We often say “when in doubt, test with clients” or “rather than debate, test with clients”. It provides extremely valuable insight, regardless of the outcome. Probably the failure I fear the most is an inconclusive test. Any other outcome is a win. It allows us to learn and move forward. Fast. It’s the early failures that taught me the most.

Most of them occurred because I didn’t dedicate enough time and put enough effort to build common understanding within the team of where we are and where we need to go. To save time, I used “go on gut” – start with assumptions, set the pace to what I felt was right and hoped that the team will adjust. This “time saving” approach, of course, saved no time. We lost half of the team before we even got to the first turn.

We had to come back to get everyone and start over again. To take someone on a successful transformation journey you have to be able to meet them where they are. That means fully understanding their starting point – where they are now, what they know, what they expect, what they fear etc. Not a minute dedicated to this is time wasted.

Only then will they trust you to lead them. You can then agree where you want to go and why and prepare a plan for how to get there. That taught me also that the value of planning lies not in the plan itself (which will likely change many times before you’ve reached your destination) but in the act of planning – building and sharing a vision of how you want to proceed.

That alignment is essential as it also enables trust – a key element of a high performing team. The inception and roadmapping sessions, OKR sprints and even the regular Quarterly Business Reviews are not just exercises in planning, but building a shared understanding of the road ahead, the potential obstacles and ways to handle them.

Especially important if we’re exploring new ground and taking roads less travelled.

Ray Freeman – Project Lead, USA

I have a bit of a challenge with the concept of getting comfortable with failure. I don’t really look at it that way. To me, ‘test and learn’ has nothing to do with success or failure. You run a test, and learn from whatever results you get. I use this concept in my personal life as much as I do in the workplace.

Whether in the midst of corporate chaos or recovering from my darkest days, there is always an important lesson waiting to be learned. As a champion of Agile, one of my personal goals is derived directly from the 5th principle of the Agile Manifesto itself. To “build projects around motivated individuals, give them the environment and support they need, and trust them to get the job done.”

When I think of failure, I think of the times when I did not honor this principle and tried to build projects around people who were NOT motivated, regardless of the environment or support they received. And guess what, they didn’t get the job done.

This taught me that being Agile is so much more than software development or transforming ways of working. It’s a culture.

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