Moving From Mystery to Confidence: 4 Ways to Embrace a Strategic Mindset

CEO sitting on top of a mountain, a business woman stealing the flame of strategy

Taking strategy from the top of the mountain. Image via Midjourney.

Practical shifts to make strategy part of your skillset

This piece originally appeared in ILLUMINATION

“Until you make your unconscious choices conscious, they will direct your life and you will call it fate.”

(adapted from Carl Jung)

The Mystery of Strategy

If you close your eyes and think of the word strategy — What images come to mind?

If you’re like many, you may come up with ideas like:

  • It’s only for super-smart people with high IQs
  • High-ranking executives
  • MBAs & PhDs
  • Basically, smarter, more important people create “strategy”
  • And hand off in large, complicated, and hard to understand strategy documents to
  • Lower-level people take it and “execute”

While many intelligent and highly-educated people work with strategy, you may be surprised that it’s not something just for them.

I invite you not to be intimidated by the word “strategy,” because it’s closer than you may think.

You already have a strategy…

Strategy, according to one of the world’s leading strategy experts, Roger L. Martin, is nothing more than a set of choices:

“…strategy is choice. Strategy is not a long planning document; it is a set of interrelated and powerful choices that positions the organization to win.”

Roger L. Martin

…and strategy is what you’re already doing

Another fundamental mindset shift is the understanding that strategy is what you do, not what you say you do.

Which brings us to the point that across every area of your life and work, you already have a strategy — in essence, it’s the set of choices you’ve made in each of those areas.

You may not have a “plan”– a thought-out sequence of how you’re going to organize some activities to create a specific result.

But consciously or unconsciously, you’ve already made a set of choices.

Why did you make those choices?

Those choices have determined where you are now, the results you’re getting, and what you’ll be able to achieve in the future.

If I asked you to take a moment and reflect on the guiding set of choices behind your decision-making process, could you clearly tell me what they are, and why you made them?

Your choices guide what you prioritize, and the decisions you end up making.

Our choices shape our results

For the most part, we’ve made choices based on many factors — our education, upbringing, backgrounds, character, and our cultures at home or at work.

They’re also shaped by the constraints imposed on us.

All of us have made our choices within constraints, and we’ve done the best we could under the circumstances.

Even a CEO has to answer to their board.

But in every case, the main question to ask is:

Are you getting the results you want?

If not, understanding better ways of making choices and shaping strategy can help.

Simplifying Strategy

In a stark contrast to what many believe strategy to be, or who’s supposed to create it, effective strategy boils down to four simple mindset shifts:

1. It’s a problem-solving tool

If our challenges exist because of the choices you’ve made, how might we structure and make better sets of choices so they can help solve problems, instead of creating them?

Everything else about strategy starts from this central problem-solving focus.

2. It’s an integrated set of choices

Roger L. Martin’s “Playing to Win” strategy framework gives us a way to design a conscious, intentional set of strategic choices.

The five choices of the Strategy Choice Cascade. Author image based on the work of Roger L. Martin.

The goal isn’t to answer these prompts to create five ideas that may sound good theoretically or separately.

The key is to have these choices work together and support one another.

  • Have you chosen a “Winning Aspiration” that inspires you, that truly embodies what it means to win in your chosen area?
  • Do your “Where to Play” and “How to Win” choices match?
  • Do you have the “Must-Have Capabilities” to deliver on your “Where to Play” and “How to Win” choices?
  • And finally, do your “Enabling Management Systems” support your “Must-Have Capabilities” so you can continuously deliver on your “Winning Aspiration”?

Instead of trying to create massive and complicated “strategic plans” filled with numbers and graphs, the output of this effort is a set of five choices that fit on a single sheet of paper.

Again, the crucial point is not to go through these steps in order, one-by-one, but to continually go back and forth through them and design them to align with and support each other.

Because achieving your “Winning Aspiration” will require you to imagine a different future.

3. Changing a future you don’t control

Strategy requires us to think creatively on positively influencing something we understand is outside of our control.

This is why client-centricity is such a crucial foundation of effective Product Strategy, and what makes it so different from a Plan.

Amazon’s best products are great examples of designing strategies that work backwards from clear client problems:

  • How can I wirelessly download and read books wherever I am? (Kindle)
  • How can I be guaranteed to quickly get the items I need most? (Prime)

You can’t force customers to do anything

It’s recognizing and accepting you can’t force your clients to do business with you — You can only create amazing experiences, and clients will be delighted to come, hand over their money, and keep buying from you.

And if they love you enough, they’ll be happy to take their own time and effort to do the best possible form of advertising, worth literally millions — convince their friends and family to also buy from you.

Your personal “clients”

Personal Strategy can be a powerful tool in your own work life.

It’s accepting our professional success isn’t entirely within our control, and we can think of our leadership, manager, coworkers, and the people we manage also as our “customers.”

We’re always looking to positively influence someone while accepting we can’t control them.

4. Is fundamentally creative

A key difference between Strategy and Planning is that Planning is always purely focused internally on things you control.

You need to bring an analytical mindset to assess your internal resources, in order to plan efficiently.

But if you’re trying to influence something outside of your control, you need to use a different mindset.

Spending all your time looking at data from the past and only looking internally at the things you control won’t allow you to design a set of choices to create a different future.

This is where people with design and UX backgrounds have an advantage over MBAs in making the mindset shifts behind thinking strategically.

Designers train using the double diamond of Design Thinking to maintain client-centric and creative approaches to problem-solving.

Strategy can’t solve all problems

Regardless of how great our strategy may be, success is never guaranteed.

Part of a strategic mindset is accepting we’re not dealing with “deterministic” systems, like computers and machines, that always give us the same result. Strategy deals with complex factors like people, personalities, and market forces, where things are unpredictable and constantly changing.

All we can do is make the “best argument” for a set of choices that answer the five boxes of the “Strategy Choice Cascade” to improve our odds and increase our probability of success.

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TL:dr; & Takeaways

We can finally take control of our choices and solve problems effectively by understanding that strategy is:

1. A problem-solving tool

2. An integrated set of choices

3. Focused on influencing something that’s inherently out of your control

4. Fundamentally creative

But remember –

  • Because we’re dealing with complex, unpredictable things, Strategy can never guarantee success, but only help improve our odds

Through these mindset shifts and mental models, we can finally take control of our choices and perhaps for the first time, direct our lives and have a hand in deciding what our fate will be.


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