Why Working Hard Isn’t a Strategy
Lessons from Roger Martin
Every founder believes they can outwork the competition. In the early days, that grit often defines survival. But at some point, hours stop compounding into advantage. What separates the companies that scale from those that stall cannot be effort alone, it’s strategy.
Roger Martin, one of the great minds in modern business thinking, reminds us that strategy is not a plan or a list of goals. In his recently published redefinition he frames strategy as an integrated set of choices that compel desired customer action. It’s not about what you’ll do, but how your decisions interact to create a position that competitors either can’t or won’t match.
Note the focus on compelling desired customer action, the one thing we cannot directly control, only influence.
That sounds obvious. Yet as Martin points out in his essay Why the How-to-Win Strategy Choice is So Hard, the “How to Win” element is the weakest part of most strategic plans. The typical startup deck brims with product features, sales initiatives, and aspirational goals but no coherent theory of why we will win. And the uncomfortable truth is: many teams don’t have one.
The illusion of effort
Martin identifies a common executive delusion: the belief that doing what everyone else does, but harder, will yield superior results. Software CEOs, especially those coming out of founder-led scrappiness, fall squarely into this trap.
You’ve hired smart people, built an impressive roadmap, and you’re pushing to “execute better.” But that’s not a winning strategy. Hard work can extend your runway, but it won’t alter your trajectory.
A true “How to Win” defines why your business will compel customers to choose you, again and again, in ways rivals cannot imitate. That’s a higher bar than “playing in a growing market” or “building great product.” It demands what Martin calls a theory of advantage: a credible, testable belief about how your choices interact to produce superior results.
From pixels to portraits
Martin draws a helpful distinction between a list of initiatives (“pixels”) and a portrait — an integrated picture of how choices reinforce one another. Winning strategies form portraits. They’re cohesive stories, not disjointed checklists.
Most “strategic plans” look more like a bag of good intentions: launch in the enterprise, expand into Europe, release an AI feature, host a customer summit. Each initiative may be sensible, but if the opposite of a choice is “stupid on its face”, for instance, not caring about customers, it isn’t strategy. It’s an operating imperative.
Strategy emerges when the opposite of your choice would be equally plausible to a smart competitor. That’s how you know you’re making a real bet. Choosing simplicity over customization, self-serve over professional services, or openness over lock-in, those are strategic choices because their opposites could also work.
Why the “How to Win” is so hard
If you’ve ever wrestled with the “how” of winning, you’re not alone. Martin highlights four reasons companies struggle:
Vague aspirations. “Be the most innovative company” or “elevate global consciousness” sound inspiring but provide zero direction.
Unlinked choices. Teams pick attractive markets (“Where to Play”) before considering how they could win there. The result: crowded, undifferentiated plays.
The delusion of sameness. Many executives quietly believe they can mirror competitors and simply “execute better.” They can’t.
Lack of external reinforcement. Capital markets and advisors often reward safe sameness over bold differentiation.
To overcome these, Martin urges leaders to explore these three vectors:
Analogy — borrow ideas from unrelated domains.
Tradeoff — refuse false either/or constraints by finding integrative answers.
Anomaly — look for patterns that contradict conventional wisdom.
Each of these requires imagination, something spreadsheets and AI rarely deliver.
Compelling desired customer action
In Revisiting My Definition of Strategy, Martin simplifies decades of thinking into this one statement: an integrated set of choices that compel desired customer action. Which is made up of these three elements:
Choices — what you will and won’t do.
Integrated set — how those choices reinforce each other.
Desired customer action — what they do because of your choices.
That last point is the heart of strategy and the Achilles heel of most startups. You can control your roadmap, pricing, team, and channels, but not your customers. The best you can do is design a system of choices that compels them to act in your favor. That’s the work of strategy: aligning everything you control to influence the one thing you don’t.
The leader’s real job
As a software leader, your job isn’t to outwork competitors, it’s to outthink them. Hard work fuels momentum, but strategy sets direction. Without it, you’re just playing to play.
Ask yourself:
Do we have a theory of advantage, or just a to-do list?
Can we articulate why competitors can’t or won’t replicate our approach?
Are our choices coherent enough to form a portrait, one that compels customer action?
If not, take a step back. Slow down. As Martin reminds us, “How to win is the hardest part of strategy. Help yourself by treating it as such. Impatience isn’t helpful.”
Hard work is admirable. But without the discipline of clear, courageous choices, it’s just motion. And motion without direction isn’t winning, it’s wandering.
Because trying harder only helps if you’re running the right race.
