Midjourney prompt: tiny fishing boat in an ocean, storm, lightning, dark clouds, big waves.

What Does It Mean to Be Strategic?

The practice of connecting intentions to outcomes

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What does it mean to be strategic? Through my experience of leading engineering organizations at Google, both as a tech lead and manager, the word “strategy” and the need to “be strategic” came up a lot across technical, product, and organizational contexts. Yet clearly defining what either might mean and consistently delivering on both has been challenging.

As I understand it now, being strategic is a sort of practice, a thinking hygiene. Simply put, being strategic means that the outcomes produced by our actions are not at odds with our intentions

A well-known thinker in this area, Richard Rumelt, has done a lot of heavy lifting to unpack what good strategy entails. Building on his work, I’ll connect intentions and outcomes into a five-step cycle:

  1. It all begins with intention. There’s something in our environment that we would like to change. Formulated in terms of motion, this intention emerges as a question of “Where do we intend to go?”
  2. To answer this question, we engage in the diagnosis of the problem, which produces a destination: where we decide to go. The next question that we ask ourselves is, “How will we get there?”
  3. Devising a guiding policy answers this question, allowing us to arrive at the approach. Then, we move onto the next question: “How will we do it?”
  4. At this step, we come up with a coherent set of actions. Finally, something we can do! As we observe ourselves taking these actions, we ask ourselves: “What are the outcomes?”  
  5. It is at this step where we usually encounter our first signals of whether we’re being strategic or not. Do the outcomes match the intention? The “What did we miss?” question is key, allowing us to compare what we see with where we started from—and repeat the cycle.

At every step in the cycle, there’s an opportunity for error that puts our intentions and outcomes at odds with each other. We’re constantly tempted to confuse our understanding of the situation with reality (“it is what we see”), and more often than not, we forget that our diagnosis is more of a hypothesis.

We’re swayed by our organizational habits, norms, practices, and culture (also known as embodied strategy) to choose approaches that are familiar rather than the ones that are called for by our diagnosis, veering us off course. 

Urged to act, we end up making up our set of actions on the fly rather than considering them deliberately.

We’re distracted by the multitude of other things in front of us, failing to execute on what we’ve decided to do.

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Shadman Rahman over 2 years ago

What an amazing read! Highly recommended!

Great article, especially these two passages...

"A strategic bandaid looks suspiciously like an oxymoron."

"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 (it usually looks like a slide deck or a doc) that looks like strategy."

I did my best in attempting to define strategy here: https://wiljr.org/2022/04/25/what-is-strategy/

John Caswell over 2 years ago

Great article! Well observed and clearly properly experienced in the real world!

Jazzy Quest14 about 2 years ago

Great article. I'm going to use this to frame a conversation in the coming week!

Alon Rozen about 2 years ago

Wonderful article - the helicopter view is perfect, the zoom in is great contextualization, the metaphors are memorable and the visuals really help to capture the essential with a minimum of words. Simple, effective, memorable, actionable, what's not to like?!