10 Ways to Ramp Up Your Strategic Thinking

I was asked recently how you teach strategic thinking. The actual ask went something like this: “You’re a good strategic thinker. How do you do it? And, how do you get others to think like you do?”

To be clear, I’ve taught a lot of things, but never this topic specifically.

So, I thought it was a great prompt to think more about my thinking and my practices – which I admittedly don’t always understand. And, I’m sure some of these are solidly based on proper strategic thinking frameworks I don’t know about, or have read about and forgot I read about them. I do know they are all rooted in how I learned to think and work as an artist, an organizer, and an entrepreneur.

So, here are my 10 tips for getting more strategic in your thinking:

1. Look two steps ahead and one step behind.      
- Two steps ahead: Where could this go? What are the possibilities? What are the probabilities? What are the pitfalls? What are the next questions that will arise as a result? What are the next challenges it will expose?
- One step behind: How did we get here? To the current state? To the current mindset? To the current decision? What is guiding our thinking today? And, back to two steps ahead: is this what should be guiding our thinking into the future?
 
2. Define your assumptions (so you can keep testing them).
This is our business. This is our ideal customer. This is our value proposition. These are our markets. These are our products and services. These are our points of difference. I’ve worked with hundreds of team members from the executive level to the frontline, and it’s rare they can confidently define these much less do so in full alignment with each other. 

3. Be strategic about what your being strategic about.
We can think strategically all day about how to solve a problem or seize an opportunity but if that’s not the right strategic problem or opportunity then we are still not being strategic. We must distinguish between presenting problems and latent problems, today problems and not-today problems, opportunities and the right opportunities. 

4. Align on “The Why”.
If you, your team, and any other stakeholders aren’t aligned on “the why” of whatever it is you are doing, then when it gets hard, things are going to fracture. Back to #2, we must not assume alignment. We should do the work to put “the why” into words so that it can consistently be shared across stakeholders and over time and not morph as a function of memory or interpretation.
 
5. Align on why.
“The Why” is about purpose. Aligning on why is about rationale. Why is this the right move? The right direction? The right investment? The right time? The right team? A good idea is only good in as much as you can provide these answers and convey them to others. 

6. Treat everything as a tradeoff.
Every choice we make to do something is an implicit choice of what we won’t do. We must discuss and make decisions based on both sides.
 
7. Assume you are wrong. Assume they are wrong.
But, be nice about it. It is the opposite of strategic thinking to assume we have it all figured out, we’ve asked all the right questions, and we have all the right data. Poke holes in everything as a matter of strategic process, not judgment. 

8. Stop nodding in agreement at blur words and vague ideas.
I mean, strategy…who disagrees we should be strategic? Everyone nods for respect and teamwork and synergy. I don’t know what any of those mean to you and certainly not to your business. Be wary of too much agreement when you haven’t even made sure you agree on what you’re talking about. 

9. Focus on the system.
What part of the system are we not thinking or talking about? What are we missing? What stakeholders have we not aligned? How does energy, investment, effort, and/or required skill shift within the system if we go this way or that? A system with one underperforming part is an underperforming system. A strategy with one underperforming part is an underperforming strategy.
 
10. Understand your starting point.
Strategy doesn’t matter unless you have the people to execute it. Your teams will determine if your intended strategy becomes your delivered strategy. Be honest about who you have and if they are ready, or what it will take to get them ready. Strategy is useless without execution. 

​