Week of 2023-06-19: The gifts of failure + Gravity and water
Where I share my learnings about contemplating failure and struggle to describe why it is so challenging to do something different within larger organizations.
Also, this newsletter is going on vacation and will be back, all tanned and jetlagged, in a few weeks. “OMG!” it will say, plopping down on the chair next to us. “I need another vacation just to recover from this vacation!” And we’ll all chuckle politely.
The gifts of failure
I may have written about this before. It’s a trick that I’ve learned intuitively over the years, and I’ve found it tremendously helpful. It tends to work best in situations where the outcome is uncertain.
When adventuring forth into the unknown, we usually focus on the thing that we want to achieve. Even if the chances of it happening are slim, we set our eyes on the prize and commit to persevere through whatever challenges are thrown at us.
It is just before this point that I usually pause and spend a bit of time contemplating the gifts of failure. The question I ask myself is simple: “What good can come out of failing in this venture?” There are usually plenty of platitudes about learning from failure and all that wonderful stuff that is talked about incessantly in books about innovation. This is not what I am looking for.
When I ask that question, I am looking for tangible benefits that might arise as a result of the failure. Once we’ve reached the threshold where we definitely know we’ve been defeated – by circumstances, a worthy foe, or our own limitations – what are we left with?
Put differently, when all we have is to pick up the broken pieces of our failed enterprise, how quickly can we repurpose these pieces to start anew?
If we don’t contemplate this question earnestly, the answer is usually “not much”. In such cases, the collapse is dramatic and total. Very little of the effort put into the project is recoverable. If anything good comes of it, it’s sheer luck.
The stepping stones tactic is one way through which we can maximize this luck. In Greatness Cannot Be Planned, the authors argued that small increments just outside of the adjacent possible – the stepping stones! – are what ultimately feeds innovation and big discoveries.
By reflecting on the gifts of failure, we can sketch our path as a series of stepping stones that we create for ourselves. What are the stepping stones will we need to produce anyway as we walk toward our vision? Which ones can take on the life of their own, and serve us even after our initial project has failed? Through this lens, the product of our endeavor will no longer look like a monolithic thing. Instead, it will be a modular construct that can flexibly rearrange itself into something completely different, becoming highly resilient.
As another tactic more useful for smaller projects, I sometimes maintain a small portfolio of secondary benefits that could be promoted as primary. These benefits must be somewhat independent of each other, so that if the initial attempts prove fruitless, there’s another path forward that opens up by refocusing on another potentiality.
Both of these tactics arise from reflecting on the original question. When we accept that in highly uncertain, volatile environments, any exploration is much more likely to fail than to succeed, we stop seeing the target of our adventure as the mythical “end all be all”, and focus on accumulating opportunities and potentialities along the way.
🔗 https://glazkov.com/2023/06/21/the-gifts-of-failure/
Gravity and water
I have been lucky enough to be part of the process of shaping several organizations, yet only uncovered this nugget of insight very recently. Very briefly, it helps to discern the forces of the broader environment that influence us without our awareness.
It is very rare that the leaders of a newly formed organization want it to behave exactly the same as the surrounding environment. If that is the case, we have a distinction without a difference, a label rather than an organization. Teams and organizations are created to do something (even if slightly) different from the rest of the environment. At the same time, they are still in that environment and are influenced by the forces of this environment.
If I want to create a team that innovates daringly while situated within an organization that is designed for keeping an important chunk of infrastructure running. I can speak all I want about inspiring creativity and fearless questing for ideas to my team – but if I don’t account for the fact that most processes around me are designed and incentives are structured for a “keeping” mission, none of that may matter. Implacably, my attempts to encourage innovation will come out shaped like infrastructure improvement projects. It will feel like an invisible force being exerted on the newly born team, veering it off our intended course.
More often than not – especially in larger organizations – such forces are invisible until we start deviating from their direction. These forces are meant to organize, to bring various people’s intentions into alignment in service of the mission. Only when we try to do something different do we start experiencing friction.
Two questions might help you start making these more visible.
The first question is “what is our gravity?” This will take a little bit of self-reflection. We rarely ask ourselves why our feet stick magically to the ground. Similarly, organizations have gravity-like forces that everyone is used to. They tend to hide in structural and cultural bits of the org. If you’d like, use my fourplex of constraints to investigate. Which ones of these do we need to counteract when deviating from the default organization configuration? OKRs are probably my favorite example here. No matter how much we try to overcome it, the language of OKRs inexorably drives us to short-term thinking. If we try to build an organization that thinks in a longer timeframe than the rest of its OKR-driven environment, we will have a difficult time placing ourselves within it. “Wait, these people don’t have OKRs? Do they even do anything?”
The second question is “what is our water?”, echoing the parable presented by David Foster Wallace. What are the things that we take for granted to such a degree that we don’t even notice them anymore? How do these things influence how we think and act? Where are they out of alignment with our intentions? If our team has a strong engineering culture, we will naturally have biases that will filter out less “engineer-ey” ideas – and that might be alright, unless these ideas are essential for making progress toward our intended mission.
The answers to these two questions are nearly always tentative and wrong, at least initially. It is important to keep examining them as the time goes on.
A while back, one of my colleagues was reflecting on their first year on a team at which we both worked at the time: “At first, I thought the hardest part will be to get creativity and inspiration going. Surely, the problem was that we weren’t thinking cleverly enough. Oh, boy was I wrong. It’s exactly the opposite! Everyone here is incredibly smart and is bursting with creative energy. Now I believe that where we struggle the most is in applying all that energy in a way that leads to shared learning that persists.” My colleague’s guess was even more refined and nuanced the next year.
Understanding what is stopping us from where we want to go is key to getting there. If we don’t stop to examine the forces that hold us in place, the best we can hope for is an external shock that jolts us out of our trap.