When everything is a priority, your strategy collapses into noise—teams pull in different directions, meetings multiply, and execution slows even when people work hard. In this article, Jef Menguin shows why real strategy requires tradeoffs, using stories of leaders who refused to choose and paid the price. Use the shift and share it with your leadership team so you stop collecting priorities and start making clear choices that survive Monday.
About fifteen years ago, I was running what I thought was a solid “strategic planning” session for a company.
Back then, I also believed strategic planning was mostly about planning—setting goals, listing projects, making timelines. So when we started an activity about which customers to keep and which ones to let go, I thought it would be a simple exercise.
It wasn’t.
The finance head came in with numbers. On one page, he showed twenty customers the sales team had acquired in the last two years. On paper, these looked good. New logos. Decent volume. Proof that sales was “doing its job.”
Then he showed the truth behind the numbers.
They were not earning from these twenty customers. These accounts were difficult, slow to pay, and heavy on discounts. Many of them took more time and attention than they were worth.
Next, he showed another line. Sixty percent of their revenue came from four companies. These four paid on time. They were less demanding. They were loyal, stable, and profitable.
Finance said, calmly at first, that they needed to focus on customers like those four. He argued that the company needed the courage to let go of the twenty, or at least reduce activities with them. “We are not earning from them,” he said. “We are burning resources.”
The VP for Sales pushed back hard.
He said they were “planting relationships,” that one day those accounts would be big, and that finance was only looking at money. He reminded everyone how hard his team had worked to win those clients, how many visits, calls, and presentations it took. To him, dropping the twenty accounts felt like throwing away all that effort.
The room turned tense very quickly. Voices rose. Body language changed. This was no longer a calm, rational discussion. This was ego, pride, and identity on the line.
They weren’t just talking about customers. They were talking about their “babies.”
And like many leaders, they could not imagine that strategy might mean letting some of those babies go.
The School That Loved All the Values
I saw the same pattern in a very different setting—a school.
I was working with a group of teachers and their principal on their strategy. The vision was easy. The mission was easy. They knew what kind of school they wanted to be.
Then we moved to values.
They brainstormed and came up with twenty beautiful values. All good. All inspiring. All worthy of a poster.
I then asked a simple question: “If you had to choose your top five—values you are truly willing to live, protect, and be known for—what would you keep?”
Silence.
One teacher said, “But all of them are important.” Heads nodded.
The principal added, “We shouldn’t rank them. Let’s keep all twenty. They all matter.”
They could not let go of any value.
It felt wrong to choose five and leave fifteen behind. It felt like rejecting something good. So instead of focusing, they kept everything.
But that’s the problem. When everything is important, nothing is special. When you have twenty values, no one remembers them. No one knows which ones to defend when things get tough.
The teachers were kind and sincere. They loved their list. But they were trapped in the same thinking:
More is better. Strategy means having more, not less.
Why We Resist Choosing
These two experiences—a company fighting over unprofitable customers and a school refusing to choose core values—taught me something important.
Most leaders are not short on ideas or good intentions. They are short on willingness to choose.
Choosing feels like loss.
If you choose to focus on four profitable customers, you feel you are abandoning the twenty you “planted.” If you choose five core values, you feel you are disrespecting the other fifteen. If you choose three real priorities, you feel you are rejecting the rest of the organization.
So instead of choosing, we keep adding.
We add customers. We add projects. We add programs. We add values.
And we call the whole pile “strategy.”
But deep down, we know what’s happening. We are avoiding tradeoffs. We’re trying to keep everyone happy, including our past selves.
Strategy Is Choosing to Win, Not Collecting More
In the Playing to Win view, strategy is not about having the thickest plan or the longest list. It is something much sharper:
Strategy is a set of choices about how you will win.
That word—choices—always carries a shadow. It means that if you choose this, you are not choosing that.
If you choose a winning aspiration, you are not trying to be all things to all people. If you choose where to play, you are not chasing every possible client. If you choose how to win, you are not copying every competitor’s move.
Real strategy means some customers are not for you. Real strategy means some projects will die, even if you love them. Real strategy means some values, while still good, are not your main banner.
This is where many strategic plans break.
On the surface, they say the right things. They talk about purpose, growth, and innovation. But when the time comes to cut, simplify, and focus, people panic.
So the organization stays in the middle: saying the word “strategy,” but living the word “more.”
Busy Plans, Blurry Strategy
If you look at most strategic plans, they are full of activity.
You will see pages of initiatives, projects, and action items. You will see tables of targets and timelines. You may even see long lists of stakeholders and risks.
What you often will not see is what they are willing to stop.
You rarely see sentences like, “We will no longer serve this type of customer,” or “We will discontinue this program,” or “We will focus on these three values and let the others go.”
Yet those are the kinds of statements that turn planning into strategy.
When everything stays, nothing sharpens. People become busier and busier, but not necessarily more effective. Teams work harder, but they are pulling in many directions.
You can almost feel it: the weight of trying to carry everything from last year while adding more for the coming year.
That is not playing to win. That is playing not to lose face.
A Gentle Check: Where Are You Holding On Too Tightly?
Before we talk about tools, it helps to pause and reflect.
Think about your own organization for a moment.
Is there a customer segment you keep serving simply because you worked hard to win them, even if they drain your margin and energy? Is there a legacy project you keep funding because “we’ve always done it,” even if its impact is now very low? Is there a long list of values, priorities, or initiatives that no one is willing to rank, focus, or cut?
If any of this sounds familiar, you are not alone. This is exactly where many teams struggle.
And this is also where strategy begins: with the courage to see where you are holding on too tightly.
A Simple Tool to See How Strategic You Really Are
Because I kept seeing this pattern—in companies, schools, and government agencies—I created a simple way to help leaders look in the mirror.
I call it the Strategy Audit Tool.
It is not a long survey. It is a short, yes-or-no checklist with twenty-five statements that touch the heart of strategy. You can answer it in ten to fifteen minutes.
It asks questions like:
Do you have a shared idea of what “winning” really means? Have you clearly chosen where you will play and where you will not? Have you actually said no to projects or clients that don’t fit? Do your priorities, values, and meetings show real choices—or just more and more?
When leadership teams use this tool, something interesting happens. The conversation shifts from “We’re busy” to “Are we actually choosing?” From “We have many plans” to “We may not yet have a strategy.”
That shift alone can open the door to better decisions.
From Holding On to Choosing Well
If you see yourself in any of these stories, there is no need to feel guilty.
It simply means you are human. It means you care. It means you worked hard for what you have.
But if you want a real strategy, caring and working hard are not enough. You will need to choose.
A good first step is to use the Strategy Audit Tool with your leadership team.
Answer the twenty-five statements honestly. Count your “yes” answers. Look at the interpretation guide. Then ask each other:
Where are we keeping too much? Where are we afraid to let go? What are we finally willing to stop, so we can give ourselves a real chance to win?
Because if everything is a priority, nothing is a strategy. And the moment you begin to choose, you start to shift from more to better—from holding on to actually playing to win.
If you’re building a business and you are playing to win…
Let’s install one shift that moves metrics.
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