Models and structured reasoningseven days beforeOne of my colleagues quipped recently that instruction tuning might not be…Gravity and water

Organizational cartography2022I’ve been thinking about how to represent the important bits of the…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.

Pace layers of predictability2023One thing that stood out to me was this notion of a…Organizing and sensing connections2021Tucked away in a couple of paragraphs of the brilliant paper by…OODA and Intention2021The ability to make predictions is an astounding quality of retained-mode systems.…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.

Separating cargo from the train2023I’ve been puzzling over a problem that many engineering teams face and…Embodied Strategy2022I was having a great conversation with a colleague about organizational learning…Something will get optimized2021Complex adaptive systems tend to make it difficult to make guesses about…Questing, Scaling, Keeping2021I’ve written a couple of takes on this before, but they didn’t…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.

Nudging Embodied Strategy2022The whole concept of the cone of embodied strategy is a bit…Steady winds, doldrums, and hurricanes2023It just so happened that this year, many of my friends and…Why will this be hard for us?2021I was working on a strategy and helping review another this week,…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.

Enumerating constraints2021The process of inferring a set of constraints with which to communicate…The language frames the story2021Suppose you’ve said to me that “the falling maple leaves whirl in…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?”

Jankless2021As we Orient, examining our prediction error and updating our model of…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.

Being Strategic2022It all begins with intention. There’s something in our environment – the…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.

What the heck is strategy work?2022We turn the mastermind toward frameworks. The key objective of this role…Tension in Shared Mental Model Space2022This just occurred to me today, so I am writing this down…Rubber duck meetings2022When I am looking for new insights, a generative conversation with colleagues…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.

Sometimes you gotta hit the wall2023I’ve probably written about this a few years back, but I still…How to get trapped2022As the first step, you must be aware of the fact that…The gifts of failurethe day afterI may have written about this before. It’s a trick that I’ve…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.