5 Strategy Questions for Leaders Who Play to Win

Weak strategy questions create heavy planning—more slides, more options, and less focus—until your team stays busy but can’t choose. In this article, Jef Menguin shares the 5 Playing to Win strategy questions leaders use to choose a path, not collect opinions. Use one question per week and share it with your leaders so meetings stop reporting and start deciding.

Let me start with a room you already know.

A CEO told me, “We already ask a lot of questions in our planning sessions. But instead of clarity, we end up with more answers, more ideas, more options. It feels heavier every year.”

Maybe you feel that too.

You ask for input. You open the floor. You gather insights. At the end of the day, you have more content, more slides, more lists—but not necessarily more focus.

So I asked him, “When you ask those questions, are you trying to choose—or are you trying to collect?”

He stopped. Then he smiled, a bit tired.

Most leadership teams treat strategy questions like a survey. They use questions to collect everything people know and everything they want.

Leaders who play to win use questions differently. They use questions to choose a path that makes other paths less important.

That’s what this article is about.

Why These Five Questions Matter

I collect strategy books.

Right now, I have 27 books on strategy on my shelf. They come from different schools, different frameworks, different buzzwords. Many of them are useful.

But there’s one set of questions that I keep coming back to, again and again, because it simplifies everything.

These are the five questions from Roger Martin’s Playing to Win work on strategy.

I want to honor him here.

He showed that strategy is not about filling templates. It is about making a few linked choices about how you will win. I’ve seen these questions cut through confusion in companies, schools, LGUs, and NGOs.

With these five questions, you can even make your vision, mission, and values clearer. You can see which words are just decoration and which ones are real choices. I’ll talk more about that in a separate video, but remember this for now:

These five questions can simplify almost everything you do around strategy.

And when you use them as choices—not as a checklist—they help you move faster and amplify results.

In the earlier articles, we already made three important shifts:

In Strategy First, Plan Second, you saw that strategy decides the game, and the plan organizes the work.
In Why Your Team Has Many Plans but Little Focus, you saw that focus comes from tradeoffs, not from adding more priorities.
In How to Ask Better Strategy Questions in Meetings, you saw that changing your questions changes your strategy conversations.

Now we put those ideas in one frame.

These five questions are the core of Playing to Win. They are simple questions. But they are not small questions. Each one is a decision point.

And here is the shift I want you to hold as you read:

Strategy questions are for choosing, not collecting answers.

You don’t ask them to create a longer document. You ask them to find the few answers that accelerate movement and amplify results.

Question 1: What Does Winning Mean for Us?

Most leaders say, “We want to win.” But if you ask ten people what “winning” means, you get ten different answers.

For one leader, winning means hitting a revenue target. For another, it means being number one in customer satisfaction. For someone else, it’s about being known as the “employer of choice.”

If you don’t decide what winning means, your team will chase different wins.

When you ask, “What does winning really mean for us?”, you are not collecting wishes. You are making a choice.

You might decide:

“Winning means being the most trusted partner for mid-sized clients in this region.”
Or, “Winning means becoming the city where young families most want to live.”
Or, “Winning means being the most profitable specialist, not the biggest generalist.”

Here’s how that changes things.

Example – A property developer: If “winning” means “launching more projects than anyone,” you will push volume. If “winning” means “being the most trusted, on-time developer for OFW buyers,” you will design your whole business around trust and delivery—not just volume. Same industry. Very different moves.

Example – A city: If “winning” means “having the longest list of projects,” you’ll spread your budget thin. If “winning” means “being the safest city for children to walk to school,” your priorities change. Streets, lighting, transport, enforcement—these rise. Other projects wait.

The right answer is the one that makes other possible “wins” less important.

Before you move on, ask yourself: “If my top team writes, in one sentence, what winning means for us in the next five years, will they write the same thing?”

If not, this is your first signal.

Question 2: Where Will We Play—and Where Will We Not?

Once you know what winning means, you must choose your playing field.

Many organizations try to play everywhere:

all customer segments,
all regions,
all products,
all issues.

On a slide, it looks impressive. On the ground, it drains energy.

When you ask, “Where will we play?”, you’re choosing:

Which customers you will focus on first.
Which locations you will truly invest in.
Which products or services will sit at the center of your efforts.
Which problems you will solve deeply.

And just as important:

Where you will not play—for now.

Example – A training company: You can try to serve everyone—students, professionals, LGUs, corporates. Or you can say, “For the next three years, we will play in the space of mid-sized Philippine companies who want to shift culture—not just skills.” That choice instantly makes some markets less important. It also helps you say no.

Example – An LGU: A mayor might say, “We will play in tourism, agriculture, and tech.” Sounds strong. But nothing gets enough fuel. Another mayor might say, “For the next three years, we will focus on becoming the weekend destination for families in Metro Manila.” That one choice can direct roads, parks, small businesses, and events. It accelerates movement.

This question uses both what you know (data, experience) and what you don’t know yet (new markets, new partners). You won’t have perfect information. You choose anyway.

Leaders who play to win do not keep expanding the field. They pick the field where winning is both possible and meaningful.

Question 3: How Will We Win There in a Way That Makes Us the Only Real Choice?

This is the core of Playing to Win.

You can define winning. You can choose where to play. But if you don’t decide how you will win in a way that makes you stand out, you are just another option.

When you ask, “How will we win there?”, you are not making a long list of strengths. You are choosing a sharp edge.

Will you win by being faster? Will you win by being more human and caring? Will you win by designing a better experience? Will you win by knowing your customers more deeply? Will you win by solving a problem others ignore?

Example – A bank: “We will win by offering more products than anyone” sounds busy, not sharp. “We will win by being the easiest bank for small business owners to deal with—fast approvals, clear requirements, no surprises.” That sounds like a real edge. It guides product, process, and people.

Example – A city in Bulacan: “We will win by developing industry and tourism” sounds generic. “We will win by becoming the easiest place in Central Luzon for small businesses to start and thrive.” That choice focuses permits, support programs, and infrastructure. It amplifies results because every move points to the same promise.

Here is the trap: leaders often say, “We will win by being faster, cheaper, more innovative, and more excellent in service.”

It sounds strong. But it is vague. It does not force tradeoffs.

The leaders who play to win choose one or two ways of winning that, when done well, make many other things less important. They accept that a sharp edge is better than a long list.

You will never be 100% sure your chosen way of winning will work. That’s okay. You learn by committing, testing, and adjusting—not by staying vague.

Question 4: What Must We Be Very Good At to Win This Way?

Once you choose how you will win, the next question brings you back to earth:

“What must we be very good at to win this way?”

This is where strategy meets capability.

If you want to win on speed, you must be very good at fast approvals, simple processes, and empowered frontliners. If you want to win on deep relationships, you must be very good at listening, follow-through, and long-term account management. If you want to win on unique experiences, you must be very good at journey design, training, and fixing pain points fast.

A hospital: If they decide, “We will win by being the safest and most trusted maternity hospital in this province,” they must be very good at infection control, emergency response, and clear communication with families. Not just marketing. The few capabilities that matter most get the most attention.

A school: If a school decides, “We will win by helping average students become confident communicators,” they must be very good at coaching, feedback, and real-world speaking opportunities. Not just exam prep. They invest in what accelerates that specific kind of win.

You cannot be very good at everything. These questions help you choose the few capabilities that will multiply the effect of your effort.

You will also see gaps.

You might admit, “Right now, we are not good at this.” That’s fine. Strategy is not a brag sheet. It is a guide for where to grow.

Question 5: What Systems and Habits Will Support These Choices Every Day?

This is where many strategies quietly fail.

You can define winning, choose where to play, decide how to win, and name key capabilities. But if your systems and habits stay the same, daily life will drag you back to the old pattern.

So you ask, “What systems and habits will support these choices every day?”

This includes:

How you budget.
How you measure.
How you reward.
How you run meetings.
How you assign people.

A company that wants speed. If they still require five signatures for every small decision, they are lying to themselves. To win on speed, they must change approval flows, redesign meetings, and teach managers to decide with enough information—not perfect information.

An LGU that wants to be investor-friendly. If they still make permits painful, with unclear steps and slow feedback, no slogan will fix that. To win, they must redesign the permit process, train frontliners, and track time from application to approval as a key metric. The habit must match the claim.

This is where Strategy Rhythm matters.

You don’t just set systems and hope. You review them—quarterly, at least. You ask, “Are our habits helping us play to win, or are they pulling us back to playing not to lose?”

You may not know which habit will matter most at the start. That’s okay. You learn by trying, reviewing, and adjusting. The key is this: you do not let your choices float above daily work.

Using These Questions to Speed up and Amplify

You might look at these questions and think, “We’ve seen similar questions before.”

Maybe you have.

The power is not in seeing them. The power is in how you use them.

If you treat them as a checklist, you will:

Fill each question with many words.
Keep every possible answer.
Create a thick document.
Still feel slow.

If you treat them as choice questions, you will:

Compare answers and drop what is nice but not essential.
Keep the few decisions that truly define your game.
Free your team from trying to win everywhere and doing everything.

That’s how you accelerate movement and amplify results.

You take many good options and boil them down to a few powerful moves that fit together.

A Simple Experiment: One Question Per Week

You don’t need a three-day offsite to begin.

Here is one simple way to start.

For the next five weeks, choose one question:

Week 1: What does winning really mean for us?
Week 2: Where will we play—and where will we not?
Week 3: How will we win there?
Week 4: What must we be very good at?
Week 5: What systems and habits will support this?

In your weekly leadership meeting:

Set aside 30–45 minutes for that week’s question.
Ask each leader to write their answer before they come.
Put the answers on the table.
Talk, compare, and simplify.

Your goal is not to capture every idea. Your goal is to leave the room with one clearer, sharper answer than when you walked in.

By the end of five weeks, you will not just have “more input.” You will have a small set of shared choices that your leaders actually remember and use.

If you want to ground this even more, ask them to reread Strategy First, Plan Second before the first session, so nobody confuses these choices with planning activities.

Simple Tools to Make the Questions Stick

You can support this rhythm with a few tools:

An Our Winning Play worksheet with these five questions in plain language, plus space for one agreed answer under each.
A 5 Strategy Questions for Leaders Who Play to Win card that you can keep on your desk or bring into every ExCom meeting.
A short video series—one video per question—where I walk through examples from Philippine companies and LGUs. Your team can watch one video before the monthly discussion.

These tools don’t replace the thinking. They simply hold the thinking together.

When You’re Ready to Go Deeper

You can start this journey with one question, one page, and one meeting.

If you want a guided, deeper experience—where your team not only answers these questions but also links them to decisions, plans, and habits—that’s where my work comes in.

Through the Playing to Win Strategy Experience, I help CEOs, mayors, and leadership teams in the Philippines:

Decide what winning really means for them.
Choose where they will play and how they will win as the obvious choice.
Identify the few capabilities and systems that matter most.

Then we use Game Plan to turn those answers into focused moves, and Strategy Rhythm to review them every quarter.

The goal is not to admire five good questions. The goal is to make a few wise choices that your people can live by.

So before your next planning cycle, you might want to ask yourself:

Are we still collecting answers—or are we finally ready to use these five questions as leaders who truly play to win?