WTF is Strategy?!

I do not think that word means what you think it means.

For the last six years, I’ve marketed myself as a “change strategist.” I didn’t think too hard or long about that label. “Change” means we’re trying to evolve your organization or team. “Strategy” means working with senior leaders to define and implement that change. Slap them together, put them on my LinkedIn profile, and move on with my life.

But I have an embarrassing confession: I’m not sure I have an explicit definition of strategy. I’ve encountered so many definitions that I’m not sure anyone does. 

This uncertainty has sent me on a quest to define strategy. It’s an ongoing quest, but I’d like to share what I’ve learned and highlight some thinkers who have influenced me. 

Maybe this post will serve as a snapshot for my future self. I’ll look back with feelings of nostalgia, cringe, or a mix of both. Maybe someone will correct me in the comment section below, saving me a lot of trouble.

Strategic planning has nothing to do with strategy.

Establishing some boundaries first might help identify what makes up a good strategy. So what is not a strategy? 

A comprehensive plan isn’t a strategy. Roger Martin explains this nicely in this HBR video:

This thing called planning has been around for a long, long time. People would plan out activities they’re going to engage in. More recently, there has been a discipline called strategy. People have put those two things together to call something strategic planning. Unfortunately, those things are not the same, strategy and planning. So just putting them together and calling it strategic planning doesn’t help.

Roger elaborates on this, defining plans as activity-centered (what will we do), whereas strategies are outcome-centered (what do we want to have happened). 

Plans satisfy the needs of stakeholders and have manageable risks and controllable costs. 

Strategies, on the other hand, aim to satisfy real customers you don’t control. A good strategy embraces uncertainty, forcing action toward learning and iteration. 

Strategy is much harder to develop and deploy than planning. Because old habits die hard, leaders resort to command-and-control planning shenanigans.  

Abandon magical thinking.

Consultants love a 2x2 matrix. Do a SWOT analysis! Create a PRD or Opportunity Solutions Tree or Lean Canvas or… There are more frameworks than you can shake a stick at. 

Frameworks and the artifacts they produce are not strategies. They might help guide your thinking, but they’re insufficient alone.

Simon Wardley, the eponymous inventor of Wardley Maps, calls out this magical thinking. In his book, he says: 

I started using 2x2s, SWOTS, Porter’s forces and all manner of instruments. Everything felt lacking, nothing satisfied… At that point in time, in mid 2004, I was drowning in uncertainty and an easy mark for any would-be consultant peddling snake oil. I would have gladly bought it. An entire crate of the stuff.

A recurring theme in his book, Simon calls out the belief that following frameworks will somehow mystically lead you to success. Trusting the process has never been my thing, and I don’t recommend it to the people we work with. 

Center your strategy on impactful change.

A good strategy will unambiguously articulate a vision of future impact and the changes that must take place to make this future a reality. 

Change comes in a few different shapes:

• Big problems to be solved: even if it’s a wicked problem that can’t be solved, how are we maneuvering around it or breaking it down to something we can manage? 

• Desired outcomes: what would we like to have happened? 

• Target conditions: what facts and properties of our system would we like to change?

In his book “Good Strategy, Bad Strategy: The Difference and Why It Matters”, Richard Rumelt defines a good strategy as having three essential components:

1. Diagnosis: Identify the critical challenges that need to be addressed. This should provide a clear and insightful interpretation of the situation at hand.

2. Guiding Policy: An overarching approach, principles, and enabling constraints for tackling the identified challenge.

3. Coherent Actions: The coordinated, focused, and complimentary steps for achieving your goals. These steps align and cohere with the guiding policy.

Where do you start? The diagnosis, of course. What’s going wrong, and what does the world look like when the problem is removed or avoided?

Treat strategy as an iterative feedback loop.

Diagnosing big challenges (step 1 of strategy development) carries a stupid amount of risk. After all, first diagnoses are theories, not laws.

I’ve been in planning (again, not strategy) rooms with senior leaders, trying to agree on a strategy. The focus invariably pulls toward analysis and risk. “We can outsmart this problem” seems to be the inner monologue. The goal is to gather the organization's smartest people and consultants to ensure we have tuned and perfected our strategy.

In that room, you’ll also have the change management folks who will take that so-called strategy and deploy it to the masses. They’ll use any number of frameworks, with ADKAR being one that comes up regularly (from Wikipedia):

• Awareness of the need for change

• Desire to participate and support the change

• Knowledge of what to do during and after the change

• Ability to realize or implement the change as required

• Reinforcement to ensure the results of a change continue

Like any framework, it serves a purpose. I’m not here to dunk on the ADKAR model. That said, it’s an implementation model for individuals subject to change. It’s not for testing or validating a strategy.

I’ve observed that some leaders tend to go straight to implementation. They’re doing planning, not strategy. When treated as a linear process, strategy becomes vulnerable to unchecked assumptions made at early stages. Much like waterfall or sequential development, those assumptions can prove costly or fatal down the line.

Simon Wardley provides a better model for strategy development with his Strategy Cycle:

Simon Wardley CC BY-SA 4.0

There’s a lot to unpack there, but we’ll take a speed run through it for now:

1. Act / Purpose - What does winning your particular game mean? What’s motivating the change? What are the stakes?

2. Observe / Landscape & Climate - What does that game board look like? What needs to move? What needs to be created or eliminated? Simon created Wardley Maps to visualize the components of your value chain (landscape) so you can build consensus around what to move, headwinds, and tailwinds (climate).

3. Orient / Doctrine - The good practices and ideas you’ll employ to clarify the map and decide on your next moves.

4. Decide / Leadership  - Taking a stab at the strategy and enrolling the people who will make it happen. 

Rinse and repeat. Every time you go around the loop, you learn some new things. Maybe your purpose becomes clearer if people find it confusing the first time. Or perhaps you choose new methods (doctrines) because you found gaps through the first couple of cycles.

Iterating on strategy leverages learning. Remember: planning is not a strategy. You are working from a position of uncertainty and probably complexity. Learning and experimentation are better than baking and following a plan.

Involve teams and contributors in strategy.

I reject the idea that strategy is reserved for the rarified air of senior leadership—that providence and an MBA qualify certain individuals to “do strategy” or “be strategic.”

Good strategies enroll all players in the process.

How many crappy SAFe or SAFe-inspired Program Increment (PI) sessions have I attended? Too many. Almost all of them fit that description.

These sessions end up as mediocre planning when they could be about negotiating people’s part in fulfilling the strategy. From a Rumelt perspective, use this time to connect the “Guiding Policy” with the “Set of Coherent Actions.” I’ve never seen that in a PI. Not once.

The same goes for OKRs. OKRs aren’t strategies. I’ve seen the practice fail numerous times because it was mistaken for strategy or done without an explicitly stated strategy present. How will you cohere objectives to a strategy that doesn’t exist?

Now, the type of involvement will depend on the leadership style. Some groups will be more creative, collaborative, and consensus-based. They’ll be able to use the wisdom of the crowds to generate objectives that align closely with a clear strategy. Others will require more negotiation or a commander’s intent leadership style. “Here’s what we’re proposing and why. What suggestions or improvements would you make before we lock it in?” 

There’s a spectrum, of course, but on both ends there’s engagement with contributors. Engagement is the best way to enroll people in this strategy. Pushing things down from on high is fraught with so many different failure modes (protective manager being one) that we’ll have to save that for another day and another post.

While the quest continues, progress has been made.

Strategy is like design. There are a thousand definitions of good design, but we all know good design when we see it. And it’s possible to achieve a good design by working through several of those definitions.

The same is true for strategy.

It’s the results that matter, not the plan. That’s where you start. Start with the big problems, desired outcomes, and target conditions. Then construct that guiding policy Richard Rumelt talks about. But don’t hold it as a law. Don’t overbuild on it. Instead, test that sucker in a loop. It’s a best guess. Start small. Roll your learnings—success and failures—into ever-refined guiding policies and enabling constraints. And, as certainty grows, you expand the scope and scale of your strategic efforts, enrolling more people along the way.