How To Get Good at Strategy
Quick pointers for improving your strategic thinking as a leader
👋 Howdy! Claire here, Founder & CEO of Canopy. In the upcoming week alone, I’m delivering 3 leadership workshops (including one in-person!) on strategic thinking — and so I thought I’d share some thoughts below on the topic, while it’s fresh on my mind ✨
Eager to hear any and all feedback on my writing. And, do consider sharing this piece with a friend or colleague who you think might enjoy as well…
Recently, several leaders have asked me: “How do I get better at strategy?”
“Strategy”— I wince at that word. It’s evolved into one of those all-encompassing buzzwords attached to virtually anything business-related requiring forethought.
Strategic planning. Strategy session. Strategic objectives.
I'm reminded of a CEO who kicked off quarterly “strategy” meetings by distributing 15 projects to his team with 12-week deadlines, and then told them: “Go reach for it!”
But what he issued wasn’t a strategy — it was a to-do list, plus a half-hearted attempt at a motivational pep talk.
A few years later, I learned that the company sadly had filed for bankruptcy. They hadn’t been able to adapt to the changing demands of the market, and their competitors had gained ground. I reflected on the CEO’s to-do list and pep talk that was prepared each quarter: What was touted as a “strategy” hadn’t addressed any of the specifics of the challenges in the market, and most importantly, how to address those challenges. And it cost the company everything.
My hope is this fate isn’t met by other leaders. When we’re tasked with “figuring out the strategy” or “getting good at strategic thinking,” we shouldn’t jump straight to OKR-setting mode or planning tactics or aspirational speeches. Nor should we use the word “strategy” as a broad attempt to justify the goalposts we feel like we need to go after…
Effective strategy dictate what goals, tactics, and messaging we pursue — not the other way around.
With this, I compiled my thoughts. From my research on strategy (see my list of recommended books on strategy below), as well as my own direct experience and what I’ve seen firsthand from leaders I’ve worked with, I wanted to share my observations here:
Centering on a definition
As consultant and scholar Richard Rumelt writes in his seminal book Good Strategy/Bad Strategy: “The core of strategy work is always the same: discovering the critical factors in a situation and designing a way of coordinating and focusing actions to deal with those factors.” This means…
Strategy is:
Identifying the most critical challenge in a situation
Addressing this challenge with some kind of coherent approach
Having coordinating actions focused on overcoming this challenge
Strategy is not:
A catchphrase (“Whatever it takes.”)
A vision (“Helping our customers live happier lives.”)
A mission (“To be the market leader in our industry.”)
A goal (“We'll reduce our costs by 20%.”)
Strategy is a distillation of what the exact challenges are, keying into what is most critical, and then coming up with an approach and set of coordinated actions to address the specific challenges with that approach.
This very definition of strategy actually denotes what is important to do well if you want to be good at strategy…
What to focus on
Single out the specific challenge
A strategy is not just saying you want things to be better. It's about understanding what's going on: Deep observations of the market, the competition, potential driving forces for change. It's about investigating underlying problems and the root-cause of those problems. After all, a strategy is only helpful for a problem if you’re precise about the problem you’re solving.
When Netflix shifted from DVD rentals to streaming, they didn't just identify a vague notion of “digital disruption” as their challenge. They specifically realized their core challenge was: “How do we maintain our customer relationships when physical media becomes obsolete?” This specific identification of the market challenge led them to invest in streaming technology and original content rather than trying to extend the life of their DVD business.
Key question to ask yourself:
“What is the true, critical challenge here that we're looking to solve?”
Inspect the dirty corners of the mirror
It's impossible to actually know the real challenges if you're not honest about all of the factors involved. This means having a desire to look at information that you may not want to hear. To peer at your own self-reflection and/or your company’s reflection when the mirror isn’t quite so pristine. A relentlessness for rooting out information from all crevasses. An openness to hearing things that are not always optimistic.
Consider Kodak's story. Despite inventing the first digital camera in 1975, they avoided confronting how digital photography would impact their profitable film business. This reluctance to face an uncomfortable truth cost them their market leadership and eventually led to bankruptcy when digital photography became mainstream.
Key questions to ask yourself:
“What information or scenario have I been avoiding?”
“What's the one thing I don't want to think about that I should probably think about?”
“Anything I've found myself glossing over, postponing, or ignoring altogether?”
Be hungry for the insight
The most effective strategic leaders are ones who are always looking for some kind of hidden insight. Something that's obvious at first glance, but in reality much more difficult to execute on. Or, the insight is derived from a slight adjustment to the current frame or approach. This hidden insight could also be a practice pulled from another analogous industry or leverage of a certain power and competitive advantage.
Airbnb famously demonstrated this principle well. Their founders spotted an opportunity others missed: During conferences when hotels were fully booked, people would pay to stay in someone's spare room. This insight — that unused living space could be monetized — led to a platform now worth billions. All from a hidden, unlikely insight.
Key questions to ask yourself:
“What's something others are overlooking?”
“Why hasn't this been done before?”
“How do we get leverage here?”
Work with the obstacle, not against it
If a strategy is in fact a set to overcome a specific challenge, then we need some kind of maneuver(s) to go around the obstacles. We can't just butt our heads against it. We must acknowledge the constraints as reality — rather than pretending we can brute force our way, or hope we get there by the strength of our ambition. The obstacle cannot be ignored.
Toyota's development of the Prius illustrates this principle well. In the 1990s, they recognized that while fully electric vehicles were the environmental ideal, significant obstacles existed — battery limitations, costs, and infrastructure. Rather than waiting for these to be solved or just pretending these obstacles didn’t exist, Toyota asked: “What would have to be true to reduce emissions with today's constraints?” Their answer was the hybrid system that became the Prius in 1997 — the first mass-produced hybrid vehicle ever. It was a direct result of working with their obstacle, not against it.
Key question to ask yourself:
“What would have to be true?”
Seek rhythm and coordination
What makes strategy work well, including the execution that flows from it, is if the actions themselves are coordinated. If the actions are connected in some way, and building on each other, they reinforce each other. And if they reinforce each other, that in fact makes the strategy stronger.
Apple exemplifies this principle in how their ecosystem functions. Their hardware (iPhone, iPad, Mac), software (iOS, macOS), and services (iCloud, App Store) all reinforce each other. When they release a new iPhone feature, it typically coordinates with software updates and service enhancements, creating a rhythm where each component makes the others more valuable.
Key question to ask yourself:
“Are the steps we’re looking to take coordinated with one another and work together to accomplish what we want to accomplish?”
Simplicity is key
The best strategies are focused. They're not overwhelming. They're not unwieldy. Effective strategy cuts through complexity to find the essential path forward, making it easier to communicate and execute.
Apple is a perennially, classic example. When Steve Jobs returned to Apple in 1997, he found a company with dozens of overlapping product lines. His first strategic move was radical simplification — cutting the lineup to just four products (two desktops and two laptops). This clarity of focus allowed Apple to concentrate its resources on making those few products exceptional rather than spreading itself thin across many mediocre offerings.
Key question to ask yourself:
“How can I keep things simple?”
Make a choice
The only way to keep things simple is to not do everything. There is real power in saying “no” — it opens up the space, energy, and resources to then concentrate on what you say “yes” to. In your strategy, you’ll want to make sure you’re not saying yes to everything, and actually turning your back on some things.
In-N-Out Burger exemplifies this principle. While competitors constantly expanded their menus with breakfast items, chicken options, and limited-time offerings, In-N-Out has maintained essentially the same simple menu for decades. By saying “no” to menu expansion, they've maintained quality, operational efficiency, and a cult-like customer following that values the consistency and focus (out-of-state friends of mine seek out In-N-Out first thing when they land in California).
Key question to ask yourself:
“What am I / what are we saying 'no' to?”
These principles provide a foundation for effective strategic thinking. However, even with these guidelines, there are common traps that can derail even the best strategic intentions.
Let's examine what to watch out for…
Strategy pitfalls to avoid
Mistaking goals for strategy - Setting targets alone is the equivalent of setting stretch goals. You need a coherent approach for how you’ll achieve those targets, and a clear articulation of the problem you’re addressing that explains why you’re reaching for those targets in the first place. That’s strategy.
Analysis paralysis - Yes, you should gather data to help define the challenge and approach — but be wary of when it becomes the excuse for not yet deciding on what path to move forward on.
Ignoring implementation - Your strategy must meet reality where it’s at — and this includes the execution capacity of your team. Don’t forget this as a factor.
Following trends blindly - Especially in this age of AI, we’re eager to watch and mimic others closely out of fear of being “left behind.” But be prudent to not over-adopt what seems to be working well for others, without considering your own context first.
Refusing to adapt - Things change. And when your market conditions change, your strategy should change with it too.
Have you been following into any of these pitfalls? Here’s a quick self-check you can use to calibrate areas of growth for yourself…
Quick strategy self-assessment
Rate yourself from 1-5 on each of these strategic thinking dimensions:
How well do I identify the core challenge beneath surface problems?
How comfortable am I confronting uncomfortable truths?
How often do I spot insights that others miss?
How effectively do I work within constraints rather than fighting them?
How well do my strategic actions reinforce each other?
Your responses to these questions can highlight where you might focus your development efforts.
But perhaps most importantly, you’ll want to keep in mind the following…
Immersion in the patterns
Above all, I've noticed that leaders who are best at strategy tend to be:
Rigorous in their search for information to inform an insight
Effective at distilling what is most important to form that insight
The ability to do both I wish I could tell you was as easy as just asking ChatGPT or reading this article — but in reality, these powers are only found through broad and deep exposure to frameworks. That is, the most strategic leaders have been receptive to numerous ways of doing something, they've seen the shape of many problems, they've learned about many people's different ways of approaching things and the outcomes. It's an immersion in patterns.
To help increase your exposure to these patterns, here are some further resources you can explore…
Further reading resources
For foundations of strategy:
Good Strategy/Bad Strategy, by Richard Rumelt - Probably my favorite overall primer on strategy.
Playing to Win, by A.G. Lafley and Roger L. Martin - A solid look at another framework for strategy creation.
For strategic thinking development
Deep Dive, by Rich Horwath - A nice read on the specific mechanics of getting good at strategy.
The Opposable Mind, by Roger L. Martin - More of a book on decision-making but still helpful for seeing alternate paths and options.
For competitive advantage building and understanding
7 Powers, by Hamilton Helmer - One of my favorite books on durable business advantages.
The Innovator's Dilemma, by Clayton Christensen - A classic for a reason, I love this as a reminder for one of the most helpful and counterintuitive understandings of innovation.
Returning to you
Remember that CEO who conflated a to-do list with strategy? His company's bankruptcy wasn't inevitable — it was the result of failing to identify and address their core challenge.
True strategy isn't about knowing everything or having perfect foresight. It's about developing the discipline to identify what matters most in your unique situation and coordinating your actions to address it.
As Rumelt reminds us: “Strategy is discovering the critical factors in a situation and designing a way of coordinating and focusing actions to deal with those factors.”
It’s your situation. It’s up to you to discover what is most critical.
You can start today: Take 15 minutes to write down what you believe is the single most important challenge facing your business right now. Not symptoms, not aspirations —the fundamental obstacle. Then ask: “What would have to be true to overcome this?” That question alone will begin to shift your thinking from tactical to strategic.
After all, strategy isn't just for CEOs or consultants — it's for anyone who wants to move beyond reactivity toward purposeful action.
-Claire
If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶
If you’re looking to improve your own or your team’s strategic thinking, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:
📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics that help leaders with communicating clearly, including “Strategic Thinking” and “Strategy Translation.”
🚂 Partner with me to roll-out a leadership training program for your managers to help them coach and keep their top performers.
🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.
🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)
I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚
I suggest reading Ben Gilad’s books on war games and early warnings.
Better take any classes he teaches for ACI.
His nuanced views provided the epiphany to launched my success as a strategist.
i like that you start with a definition. "strategy", as you say, has become a confusing topic because the word has been recklessly and ignorantly used.
i suggest a different definition. but first, consider this.
when we create words it is intended to communicate a thought. we don't usually have two words that mean exactly the same thing. words usually have nuanced differences. but people regularly dismiss nuance and use different words interchangeably (and inaccurately). Example: people say they are jealous when they mean they are envious. Jealousy means the fear of losing something you have. Envy means wanting what someone else has... I hear these misused many times per week.
My point? "Strategy" was meant to mean something different than doctrine, tactic, innovation, etc.
When we know what we want to achieve, but it is complex, we are wise to execute a project using project management concepts (whether waterfall or agile). So, when we engage a contractor to build a home, they should create a project plan. There are still many unknowns like color of the carpet, paint choices, appliance choices, etc. But you don't start building a home without a plan that depicts the size, shape, style, architecture, etc. This requires much certainty.
But, what do we humans do when we are faced with uncertainty about how to achieve an objective?
The condition of uncertainty led to us create the word, "strategy".
Before sharing my definition, here is a view of organizations.
i need to share this because, people don't really understand what an organization is either. They will say, "i knew that". But i have rarely heard this articulated...
AN ORGANIZATION IS a collection of processes that utilize capabilities and assets to achieve a common goal.
With all that pretext, here is my definition of strategy:
STRATEGY IS the method used to deal with an uncertain future that we think could cause our failure (WHY we need strategy); by identifying the capabilities and assets needed to meet our objectives in that uncertain future (WHAT makes strategy different than project management or process engineering or business architecture); by identifying a view of that future, the dynamics we expect will shape success in that future, and the capabilities and assets needed to succeed in that future (HOW to use strategy).
Strategy is all about "uncertainty".
To come to this definition, I read over 100 articles (HBR, SLoan, Stanford, UCLA, more), dozens of business books (including Harvard's “10 Must Reads from HBR On Strategy”), military books, watched untold numbers of videos, and listened to what seemed like a million so called "experts".
Eventually, i had to create my own definition because all these sources promised definitions but instead offered examples or entire chapters to explain "strategy".
Anyway, all this leads to an organization creating what people call "the strategy", which provides a label or the "theme" of change, and an explanation of the capabilities and assets needed for success in that uncertain, but expected future.
Example labels for “the Strategy”: 1.) use AI to modernize insurance operations; 2.) separate our manufacturing processes from our distribution processes; 3.) decentralize our personnel.
Each of these communicates something that needs to be achieved, without the specifics of how it will be achieved.
To get the specifics leads us to "strategic planning" which identifies how we will attain the capabilities and assets we think will enable us to achieve our objectives in that uncertain future.
Both “the Strategy” and the Strategic Plan need periodic monitoring because as we approach that “uncertain” future, some aspects will become certain, or less uncertain, and some things will be dismissed.
Strategic planning uses the same methods as project planning except for how objectives are prioritized... briefly, to get resources allocated to work that is deemed to be "strategic", the sponsor must show that the work leads to the attainment of a capability or asset needed in that uncertain future (as described in "the Strategy"). This is not the same as finding linkage to "the strategy". It is too easy to make operational improvements seem linked to the strategy.
So, my views on strategy. They served me well as the strategist for 4 consecutive CEOs of an F100 company over 25 years...