Strategy First, Plan Second

A strategy plan becomes dangerous when people call the document “the strategy,” because teams stay busy while the organization still pulls in many directions. In this article, Jef Menguin explains the clean distinction: strategy chooses how to win, the plan schedules the work. Apply it and share it with your team so managers stop adding projects and start making sharper choices.

Let me start again with what I see in real conversations.

A CEO invites me to talk about leadership development or culture shaping. We sit in a boardroom with the HR head and a few senior managers. They share their strategic plan. It has pillars, values, timelines, and a neat list of projects. It looks serious. It looks complete.

Then I ask a simple question:

“How will this leadership program support your winning aspiration?”

The room pauses.

Someone talks about “engagement.” Another talks about “performance.” Another says “alignment” or “excellence.”

The words are good, but they don’t really answer the question. So I ask again, in plainer language:

“If I am a new manager here, and I ask you, ‘How is this company trying to win in the next three to five years?’ — what would you say?”

This time, I hear different stories.

One leader talks about being number one in customer service. Another talks about expanding abroad. Another talks about becoming a tech-driven company. Another focuses on cutting cost and protecting margin.

All of those can be true. But they are not the same game.

I did not design their strategic planning. I only came in to design leadership and culture experiences. Yet this happens so often that I now expect it.

Maybe you recognize some of this in your own organization.

Why the Old Way Fails CEOs

Let me zoom out for a moment.

The old way taught us to treat “strategy” and “plan” almost as one thing. You say, “We need a strategy.” Your team answers, “Let’s schedule strategic planning.” You come back from an offsite with a document called “Strategic Plan 2026.” From that day on, people call the document “our strategy.”

On the surface, that sounds neat. You asked for strategy. You got a plan. You put it in a folder. Done.

But what happens after?

You see departments creating their own “strategic plans.” You hear managers saying “our strategy” when they mean “our list of projects.” You sense that everyone is busy, yet the organization still feels pulled in many directions.

If this old way worked, your strategic planning would make things simpler, not heavier. You would see clearer choices. You would hear one consistent answer when you ask, “How are we trying to win?”

Is that what you see today?

If not, it’s not because your people are weak. It’s because the words have blurred. We turned strategy into paperwork.

Strategy Decides the Game. The Plan Organizes the Work.

So what needs to change?

Here is the shift I invite you to make:

Strategy decides the game. The plan organizes the work.

Strategy is about how you will win. The plan is about what you will do.

Strategy is a small set of decisions about who you’ll serve, where you’ll play, how you’ll stand out, what you’ll stop doing. It gives you a clear game.

The plan comes after. It translates that game into projects, timelines, budgets, and roles.

When you treat the plan as the strategy, you ask the document to carry meaning it doesn’t have. A list of initiatives cannot replace a shared understanding of the game you’re playing. That’s why people can follow the plan and still feel lost.

But when you put strategy first and plan second, conversations change. You stop asking, “What else should we include in the plan?” and start asking, “What game are we choosing to play—and how will we win it?”

The plan becomes lighter and more focused because it finally serves something clear.

The Game and the Schedule

Let me use a simple picture.

Imagine you coach a basketball team.

Your strategy is the decision to win by speed. You choose to play fast, press on defense, and force turnovers. You recruit players who can run. You accept some mistakes because pace is your edge. That is your game.

Your plan is your schedule. It tells you when you practise, which drills you run, who starts, who comes off the bench, and how you prepare for each opponent.

If you change your strategy—say you now want to win with size and slow control—your plan must change. New drills. New lineups. New routines.

But if you only change the plan—add more practices, reshuffle some sessions—your strategy may still be fuzzy.

In many organizations, leaders are very good at schedules. They know how to list projects, assign owners, and set deadlines. But they don’t always decide the game with the same clarity.

So the team moves. But not always in one direction.

What I Hear in Discovery Sessions

Let me go back to those discovery sessions.

When I design leadership development or culture programs, I always ask:

“How will this intervention support your way of winning?”

I want to see the line from the work we do to the future you want.

Many times, leaders go back to their strategic plan in their minds and pull out phrases. They mention “customer-centric,” “innovative,” “world-class,” “people-first.” These words sound good, but they don’t tell me the game.

So I invite them to try again:

“Imagine you’re talking to a new senior manager. How would you explain, in one simple sentence, how this company is trying to win?”

That’s where the room becomes quiet.

Some leaders suddenly realize that they’ve never had to say it that simply. Others notice that their own picture of “how we win” is not the same as their peers’.

This is not a failure. It’s a mirror. It shows that the plan exists, but the shared strategy may not.

Before we move on, you can try this in your head now. How would you explain your way of winning in one sentence, to a new leader, in plain English?

If it’s hard to say, it’s a useful signal.

Using Your Planning Time Differently

So what can you do about it?

You don’t have to throw away strategic planning. You just have to use that time for what it should really do.

Instead of starting your planning session with, “What are our initiatives for next year?”, start with, “How do we want to win?”

Stay with that question longer than feels comfortable. Ask your leaders to write their answer, in their own words. Put the sentences on the table. Look at them together. Notice where they align and where they don’t.

This is the kind of work we do in Playing to Win.

Playing to Win is a structured conversation around five big questions:

why you want to win,
where you will play,
how you will win in a way that makes you the only real choice for the right customers,
what you must be very good at, and
what systems must support those choices.

We are not filling a plan yet. We are deciding the game.

Once that game is clear, Game Plan becomes much easier. Now the plan has a job. You pick a few focus areas. You name the key projects. You assign clear owners. You remove items that don’t serve the game. Managers can finally see how their work connects to strategy, or not.

Then we build a Strategy Rhythm. Usually that’s a quarterly session where you and your leaders step back and ask, “Are we still playing the game we chose? Is our game plan still helping us win? What needs to start, stop, or change?”

Same time. Same people. Different order. Strategy first. Plan second.

A Small Experiment You Can Try

Let me offer a small, low-risk experiment.

At your next ExCom or senior team meeting:

Give each leader a sheet of paper.
Ask them to answer this question in one simple sentence:“In my own words, this is how our organization is trying to win in the next three to five years.”
Ask them to write it as if they’re speaking to a new manager.
Then invite them to read their sentence.

Just listen.

You don’t have to fix anything in that moment. You don’t have to debate whose wording is “right.”

Just ask one more question: “What does what we’ve heard tell us about our strategy today?”

That conversation may be more valuable than another long slide deck.

Simple Tools to Support the Shift

You can make this shift easier with a few simple tools.

You can share a one-page Strategy vs Plan Guide with your leaders. On that page, you show a few examples of real strategy statements and sample plans that follow. You can talk through it in ten minutes at the start of your next planning cycle.

You can use an Our Winning Play template before anyone opens PowerPoint. One page. Four or five prompts. Who we serve. Where we will play. How we will win. What we will stop. This forces the team to decide the game, not just decorate the plan.

You can record or share a short Strategy First, Plan Second video. Let your managers watch it before your next planning meeting so they start with the same language in mind.

These are not huge investments. But they remind everyone of the same truth: strategy decides the game, the plan organizes the work.

When You’re Ready to Go Deeper

You can start with questions, a page of paper, and a short exercise. Many CEOs do. And just that already changes how they hear their own team.

But what if you want to turn this into a full shift?

That is where I come in.

My work as a strategy consultant is to help leaders make wiser choices.

Through the Playing to Win Strategy Experience, I guide CEOs and leadership teams decide the game they want to play and how they will win it. With Game Plan, we turn those decisions into a clear, usable plan your managers can actually follow. With Strategy Rhythm, we meet quarterly to check your progress, adjust your plan, and make sure you are still playing to win.

The goal is not another heavy document. The goal is clarity, focus, and a living strategy your people can understand and use every day.

So before your next “strategic planning,” you might ask yourself:

Are we about to organize the work again? Or are we ready to decide the game first—and then let the plan follow?