Bad strategy meetings waste hours because leaders ask weak questions, people hide behind updates, and the room leaves without clear next moves. In this article, Jef Menguin shares how to ask better strategy questions in meetings—the kind that force choices, tradeoffs, and direction. Practice these questions and share them with your leadership team so your meetings stop reporting and start deciding.
Let me bring you into a strategy meeting I sat in not too long ago.
A mayor invited me to observe.
We met not in city hall, but in a five-star hotel in Makati. The room was quiet, carpeted, and far from the noise of his city in Bulacan. Around the table were his trusted consultants and a few department heads.
Before the meeting, the mayor told me privately, “It’s so hard to bring out good ideas from my department heads. Even my consultants don’t agree with each other. Maybe you can see what’s wrong.”
So I sat in the back and watched.
The meeting started with a nice slide: “Strategic Direction for the City.” One consultant took the floor and began with numbers and trends. Another consultant added national context. A third spoke about “best practices” in other LGUs.
Then the mayor turned to his department heads.
“So,” he asked, “any reactions? Any ideas?”
Silence.
One department head gave a safe comment about “implementation.” Another asked for more staff. Someone mentioned that “budgets are tight.”
The consultants debated each other’s ideas. The department heads retreated. The mayor looked more tired as the hours passed. After the meeting, he told me, “We talked a lot, but we still don’t know our next moves.”
Have you ever been in a room like that?
Why the Old Way Fails Strategy Meetings
Let’s zoom out for a moment.
Most leaders—including mayors and CEOs—were never really taught how to run a strategy conversation. They were taught how to run update meetings.
So the questions they use sound like:
“Any updates?” “What’s the status?” “Do you agree?” “Any other concerns?”
These questions are safe. They invite reports and polite comments. They do not invite real thinking or real choices.
You see the same pattern in LGUs and companies. People come with slides. They tell you what has been done. They highlight activities. They protect their own projects. When time is almost over, someone asks, “So… are we aligned?” and everyone nods because they want to go home.
If this old way worked, your strategy meetings would regularly produce clearer direction. You would hear sharper priorities, not just longer reports.
Is that happening in your meetings today?
If not, the problem may not be the people in the room. The problem may be the questions you keep asking.
Change the Questions, Clarify the Strategy
Strategy is not only what you write in a document. Strategy is what your leaders talk about and decide, again and again, in meetings.
If your questions invite only updates, people will protect the old way. If your questions invite choices, people will start to see new options.
Questions are not decorations. They are levers.
When a mayor asks, “Any comments?” the easiest answer is silence. When a mayor asks, “Which of these ideas will really help us win the game we chose for this city?” the room has to think.
One kind of question keeps the fog. Another kind of question clears it.
Fog Questions vs Clarity Questions
Think of the questions you hear most often in your own meetings.
Fog questions sound like this:
“Any updates?” “Any reactions?” “Are we okay with this?” “Can we all agree?”
They are vague. They are soft. They are easy to answer without saying anything important.
Clarity questions sound different:
“What are we trying to win here?” “Which of these options gives us the best chance to win the game we chose?” “If we say yes to this project, what will we stop or delay so it can succeed?” “What would we do if we wanted this city to be the first choice for investors in the region?” “If this project succeeds, what will citizens feel that they don’t feel today?”
These questions have a direction. They force tradeoffs. They surface fears. They expose assumptions.
You can feel the difference.
Fog questions make people lean back. Clarity questions make people sit up.
Back to the Mayor
Let’s go back to that hotel meeting.
After two hours of updates and consultant debates, the mayor looked at me and said, “So, Jef, what do you think?”
I didn’t give a long speech. I asked his team one question:
“In one sentence, how will these ideas help your city win in the way you said you wanted to win?”
The consultants looked at each other.
One said, “These projects are aligned with our vision.” Another said, “Other cities are also doing this.” A department head said, “We need to do something, otherwise we will be left behind.”
I followed up gently:
“I understand. But if a citizen asks you, ‘Mayor, how exactly is our city trying to win in the next three to five years?’, what would you say?”
The room became quiet.
The consultants realized they had been arguing about projects without a clear shared picture of the game. The department heads realized they had been reacting, not deciding.
We did not solve everything in that moment. But the mayor saw what was missing: not more reports, but better questions.
How Playing to Win Changes the Questions
This is where Playing to Win becomes useful.
In Playing to Win, we walk leaders through 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 people,
- what you must be very good at, and
- what systems must support those choices.
Those questions do more than create a strategy document. They give you a language for meetings.
After a Playing to Win session, a mayor or CEO can start asking:
“Does this project help us win where we decided to play?” “Is this idea part of our edge, or are we just copying others?” “If we approve this, what will we stop so we can do it well?”
The questions line up with the strategy. And when the questions change, the strategy in practice changes too.
This also shapes Game Plan and Strategy Rhythm. In Game Plan, you ask, “Which few moves will we really back?” In Strategy Rhythm, you ask, every quarter, “Are we still playing to win, or are we drifting back to busy work?”
A Small Experiment for Your Next Meeting
You don’t have to redesign everything at once.
In your next strategy meeting—whether you are a mayor, a CEO, or a department head—try this small experiment.
Before the meeting, look at your agenda. Identify three points where you usually ask things like:
“Any updates?” “Any comments?” “Are we aligned?”
Now replace those with three clarity questions. For example:
“What decision do we need to make about this today?” “How does this proposal help us win the game we chose?” “If we say yes to this, what will we stop or delay so it can succeed?”
Tell the group at the start, “Today, I want us to focus more on decisions than updates.”
Then run the meeting.
Notice what changes.
Where does the room get quiet? Where does it get uncomfortable? Where do you hear something honest that you have not heard before?
At the end, ask, “What changed when we used these questions instead of the usual ones?”
That short reflection can teach your team a lot.
Once you’ve tried that once or twice, you can support your team with a few simple tools.
Simple Tools to Help You Ask Better Questions
You can support this shift with a few simple tools.
You can create a Strategy Question Card. One small card, printed or digital. On it, you list ten good questions like the ones above. You bring it to every meeting. When the room feels stuck, you pick one and ask it.
You can use a Strategy Meeting Agenda template. At the top, you write, “What decisions about our strategy do we need to make today?” Under each topic, you add, “Key questions:” so people come prepared to think, not just report.
You can prepare a short “10 Strategy Questions for Mayors and CEOs” guide. You can send it before planning season or strategy reviews. You can even remind them of the first article, Strategy First, Plan Second, to make sure everyone understands the difference between deciding the game and organizing the work.
These tools are not complicated. But they change the default.
When Questions Become Your Strongest Tool
What happens when you do this again and again?
Strategy meetings stop feeling like long status briefings. People come ready to think. They know you will ask “why,” “how,” and “what will we stop,” not just “what happened.”
You start catching bad ideas earlier, before they eat time and money. You start seeing which projects truly fit your way of winning and which ones only look good on slides.
Most of all, you send a clear signal: “This is not just a place to show work. This is a place to make choices.”
If you want to ground this even more, you can go back to Strategy First, Plan Second. That article explains why strategy must decide the game and the plan must follow. This article adds one more layer:
Your questions are how you protect that game every time you meet.
When You’re Ready to Go Deeper
You can start this change with three new questions in one meeting.
But if you want to build a leadership team—whether in a company or in an LGU—that thinks and decides at a higher level, this is where I can help.
Through the Playing to Win Strategy Experience, I help leaders in the Philippines anchor their strategy on five clear questions they can use in every room. With Game Plan, we turn those answers into a simple plan that guides daily decisions. With Strategy Rhythm, we meet quarterly to ask the right questions about progress, tradeoffs, and next moves.
The goal is not to have clever questions. The goal is to have honest, useful conversations that lead to wiser choices.
So before your next “strategy meeting” in that hotel, boardroom, or city hall, you might want to ask yourself:
Will we spend our time asking for updates—or will we start asking the kind of questions that can actually change how we 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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