TL;DR: learn from failures, especially inconsequential. Incorporate what you’ve learnt into your decisions. And be nice to people.

“Lemons represent failures” is a failed metaphor. Lemons are just fine. You need their juice to make tahini. For many years lemon juice was the only way to avoid getting scurvy in the Arctic. Yeah, they are sour. Sure they’re not a staple food. But lemons are actually cool, and sometimes even vital.

Like with the failure of the lemon-as-failure metaphor, failure of all kinds is a pervasive inclusion in most things we do even on a daily basis. The rest of this piece will figuratively argue the case of lemons as a source of vital nutrients.

The Forest Where I Walk

Since I’m doing pretty well overall (and am deeply thankful for that), some people assume failure is a rare occurrence for me. The truth could not be further; here are some examples at various scales:

I refactored some APIs a couple of months ago (a positive thing per se), but introduced a bug in one of the code paths and broke production, not once but twice.
I let at least two projects in the recent couple of years drag on without clear success criteria, which led both to waste time, resources and good will.
A few jobs back I had made what I still regard as an important engineering innovation, but failed to convince why it was necessary, and why I was awesome for doing it, which set me up for a fairly rough ride.
Speaking of which, on that occasion I absolutely failed choosing the right job profile, as a result joined the wrong employer and also failed finding a decent executive sponsor.

Inner work: the praxis of failure as an individual

Only a small fraction of all failures are catastrophic. We need to tune the size of failures that we mind, so that we can practice handling them routinely; that way we can often learn a great deal without actually having had to lose a lot; perhaps we could even avoid some of the catastrophic failures. If I had taken more care of the projects going astray, I would have avoided the need to cancel them traumatically.

Failure never ceases, but as we become more experienced, it becomes rarer. Striving to a zero failure rate is misguided. Zero failures means no risk being taken, which is inconsistent with any form of progress. I will continue writing imperfect code, even though I hope to toil less to make it good enough.

Failure is the beginning of a story. Deliberate change may only begin if there’s a way to describe what went wrong. In turn, the description could be analyzed in order to hatch a plan. Conversely, without a failure to begin with, there’s no room for proactive planning. As an example, my ideas about what went wrong with that employer drove me to reconsider my career, overall in a positive direction.

Team retrospection: steering between the rock and the hard place

A lot of people who successfully grow as individuals fail in inducing organizational improvement. I conjecture that the main cause for that is a taboo on publicly examining failure, which stems from the conflation of failure with blame.

Humans tend to place blame as a part of social power dynamics. A failure is a great cause for a display of power – “I am the boss, and to prove my power, I place blame on people who do badly, lowering their status and raising mine”.

Placing blame is an especially destructive force for tech organizations, due to the fact that tech outcomes depend on entire teams rather than individuals. Very few are the cases in which it’s honest to blame just one or two specific persons. The vast majority of failures are caused by multiple factors, and very often managerial decisions, policies and neglect are a major part of failures.

Given the above, the right call is to work out a culture of tracing back troubles and grievances to their causative factors. To maintain the integrity of such culture over time, it needs to apply to everybody on the team, including the leadership, and be focused on things that can be and are likely to be made better.

Unfortunately instead of doing this right thing, a lot of people and organizations overcorrect and go to the extreme of making all consideration of failure a taboo. While indeed disarming the toxicity of blame culture, tropes like “let bygones be bygone” and “water under the bridge”, become a pretext to refuse to stop and learn. This means that failure is going to continue and compound – because unmanaged failures tend to stand out. And trust me, teams notice such things.

Incorporating retrospection to form a better future

While proper retrospection into the past is crucial to understand what needs improvement (without tearing the team apart by blame), such learning can only be meaningful when we use it to make new decisions.

Assume now you are nearing a new decision point. What do you do now? I suggest conducting a short semi-formal session, perhaps even on one’s own or with a few fellow stakeholders:

Put together a list of potential failures informed by the learnings so far,
If there’s at least one potential failure that is severe and impossible to mitigate, that could be a great flag to change course.
Otherwise, use your domain expertise and previous learnings to propose mitigations for the potential failures.
Prioritize the mitigations by their relative importance, and in a lean fashion, focus only those items that make the most sense.

If the above process has been done properly and thoroughly and communicated concisely, the result is clarity around what to do. Few things compare to how such clarity instills confidence in the team - for it indicates their professional well being is looked after.

Wrapping up

It is impossible to be attempting anything of substance and not fail at this level or other. However, given the austere climate we’re in now, a preventable failure could be one failure too many.

For me the conversion of failures into better choices is the absolute core of my executive responsibility. Learning the ropes of how to do it in a given team is therefore a vital part of my own professional growth.

I strongly believe that an agenda that’s grounded on the past and is well thought-out to balance the risk and the gain is the way to go, as long as the one rule of the road is kept: there are minor failures and major ones, and some bad enough to get someone fired, but no failure justifies being unkind - either to others or to yourself. Go forth and good luck.