Being Strategicfour days beforeWhat does it mean to be strategic? It is a sort of…What the heck is strategy work?

A strategy and a plan2021A colleague asked me this great question: “What’s the difference between a…The nature of the challenge2021While working on a strategy this week, I realized that one of…I am realizing that I’ve been gabbing on and on about strategy and strategy work, and I have never actually defined what strategy work entails. The word “strategy” evokes a variety of images, and when I say “what is strategy work?”, a few stereotypes show up.

One interpretation is a visage of a wizard: me sitting in an ivory tower, all-seeing, devising the next big artifact that will forever alter the landscape of the industry. This picture implicitly includes a sort of power that no individual possesses, at least in practice.

Doers, Thinkers, and Magicians2023The final ingredient in the early adopter mix are the magicians. The…Another interpretation is that of a magician, whereby I travel from team to team, setting them on the right path as a sort of strategy debugger. This depiction is quite popular in the industry, though I have doubts about the long-term durability of these engagements – a sort of strategic bandaid, which looks suspiciously like an oxymoron.

Yet one more metaphor that I’ve seen used to describe someone engaged in strategy work is a mastermind who is weaving the web of influence across the organization, quietly pulling strings to ensure that all the necessary bits are flowing to their proper destinations.

All of these are a bit cartoonish – and yet all have a grain of truth in them. Strategic work means having a perch to observe what’s happening across a broad perspective and providing a stream of insights. It also means engaging with various teams and helping them wrangle with their strategy challenges. And of course, strategic work is about creating conditions, so yeah, behind-the-scenes influence is most definitely involved.

Being Strategic2022What does it mean to be strategic? It is a sort of…So what the heck is strategy work? At the core, doing strategy works means helping an organization to be strategic. How does one even do that?

Innovation frontier2023First, we need to know what our embodied strategy is. We need…Continuously Integrated Strategy2022Somehow, these amazing ideas don’t seem to extend to strategy. In the…Embodied Strategy2022I was having a great conversation with a colleague about organizational learning…A clarifying insight for me was this: strategy is a team sport. One of the most common mistakes a strategist can make is to presume that they get to “make strategy”. They may produce a sleek artifact that looks like strategy. They may even get the leaders to enthusiastically co-sign it. However, unless this artifact describes what the organization already does, it isn’t the team’s strategy. As a team, we make decisions that influence our team’s future. Every decision we make adds up to the sum vector of where we end up going. We all do strategy work. The strategy we end up with is what emerges from our collective efforts: the embodied strategy.

Generating ideas and strategy coherence2022Here’s the thing. In software engineering (as likely in many technology fields),…Thus, the mission of a strategist is not to set or devise strategy: it is to understand how our strategy emerges and why, then constantly scrutinize and interrogate the process, identifying inconsistencies and nudging the organization to address them. In this way, strategy work is a socratic process: gradually improving the thinking hygiene of the organization.

Archers, Captains, and Strategists2022Imagine a fun medieval-themed board game, where we all draw different cards.…Now that we’ve diagnosed the problem and chose the approach to strategy work, what is the set of the coherent actions that a strategist undertakes to fulfill their mission? To reveal these, I will take our earlier tropes and convert them into healthier roles.

The ODA and OODA stances2023Organizations operating in the OODA stance focus on bettering their mental models.…The wizard evolves into the role of sensing. In a VUCA world, staying deeply engaged with the environment is key – as well as sense-making like there’s no tomorrow. If we are to diagnose problems and understand the outcomes of our actions, we need to have clarity on what is going on. To be sensing means to stay aware of the variety of signals, curating them into a set of legible forces, patterns, and trends. Sensing needs to be both externally-facing and internally-facing: understanding what happens outside of the organization as well as inside. This is where that wizard’s perch comes so handy. To remain unbiased, observing and sense-making needs a bit of detachment from the daily slog.

Vision-oriented and impact-oriented mindsets2022I had this really interesting framing pop out during a chat with…Rigor and shared mental model space2021Alex Komoroske has another great set of new cards on rigor and…We turn the mastermind toward frameworks. The key objective of this role is to ensure that there are rubrics, lenses, and framings in place that help establish and grow the team’s shared mental model space. Shared mental model space helps build shared vocabulary that acts as scaffolding for effective strategic work.

Intention and shared mental model space2021Hamilton Helmer pointed out this amazing connection between intention and shared mental…Tension in Shared Mental Model Space2022This just occurred to me today, so I am writing this down…When a lead brings up the innovator’s dilemma or an invisible asymptote, and nobody else knows what that is, it’s a potential loss of insight: the lens just drops on the floor. It wasn’t part of the shared mental model space. Who has the time to explain and deeply understand the concept? Conversely, in a large shared mental model space, people can talk almost in shorthand and still achieve high strategic rigor.

Jankless2021As we Orient, examining our prediction error and updating our model of…Lenses, framings, and models2022At a meeting this week, I realized that I use the terms…Why will this be hard for us?2021I was working on a strategy and helping review another this week,…Here, mental model hygiene is critical. Broken lenses (like “we should just work harder!” or “I would simply…”) can cripple or doom the team.

Organizational pathology2022I was reading the latest book by Richard Rumelt, The Crux, and…A recently learned lesson for me is that frameworks aren’t processes: the former are the blueprints for the latter. When the operations folks devise and implement a process, they are much better off if there is a framework to help shape it. Otherwise, a process will be informed by the embodied strategy, all of its existing inconsistencies embedded.

Nudging Embodied Strategy2022The whole concept of the cone of embodied strategy is a bit…Finally, the healthy version of the magician trope is practice: the responsibility to keep the collective strategy muscle engaged. Instead of simply running from fire to fire, I want to proactively establish robust strategic thinking practice within my organizations. Such practice can take many forms.

Strategy and FOMO2022In itself, feeling fearful about missed opportunities is not a bad thing.…For example, in my team, we’re currently eyeing scenario planning and systems thinking as strong contenders. Whatever it is, it must be something that spurs team leaders to lift up their heads from the minutiae of execution and shift their minds to think longer and broader.

With the practice in place, engaging with teams across the organization becomes a coaching function, rather than the reactive band-aid.

So really, what this translates to so far is a strategist playing three roles at once: sensing, frameworks, and coaching. This is not an easy task.

Organizing and sensing connections2021Tucked away in a couple of paragraphs of the brilliant paper by…Pace layers of predictability2023One thing that stood out to me was this notion of a…Settled and “not settled yet” framings2021I was working on decision-making frameworks this week and had a pretty…Framework and sensing roles are nearly diametrically opposite in nature. Sensing role implies wholly engaging with the full complexity of the environment, letting it wash over, spotting interesting trends, gardening my collections of known forces and their traits. When in a sensing role, I might spot something very novel and groundbreaking, something that requires a dramatic rethink of everything … and that’s where it runs straight into the framework role’s wall.

The problem understanding framework2022When starting on this adventure, I wanted to construct a framework that…Because the framework role is charged with creating conditions for a shared mental model space across the leadership team, it is naturally conservative. When wearing this hat, I want to ensure that there is a stable foundation of framings and lenses, neatly polished, accessible to all, easy to grasp, like tools in a toolbox. The silly sensing role keeps constantly messing with this toolbox, questioning whether the screwdriver is actually a butterfly … and what if this wasn’t a toolbox, but rather … oh, I don’t know, a sunset?

Dandelion or Elephant?2022The discovery of the dandelion/elephant framing was exciting and my fellow FLUX…Keeping both roles in one head is maddening and requires a lot of practice. This was one of the big lessons for me – time management and calendar-slicing need to keep framework and sensing roles separate from each other. In some sense, it’s like having to apply both dandelion and elephant strategies – I am better off not mixing them. At the same time, I am weary of delegating these to separate individuals: the inherent tension will likely result in friction between them. Something to think about.

Flux budget and predictability footprint2021I’ve been thinking about this idea of the flux budget as a…Speaking of time management… In addition to the need for a regular strategy practice within this team, the practice role is easily the biggest temporal vampire and randomizer of the bunch. The demand to jump in and help out with some strategic thinking ebbs and flows, and It’s simply difficult to know when the next interesting thing happens. Just when I have my framework and sensing hats sorted out, the practice hat barges in and announces that my help is needed. Gotta stay nimble.

Dandelions and Elephants, Illustrated46 days afterOver the holiday break, I made a thing for you to enjoy.…I hope this helps y’all see the shape of strategy work a bit better. Does it resonate? Did I mess it up? Missed something? Let me know.