Read this when your strategy meeting ends with a long list—and you already know Tuesday will ignore it. You want your team to play to win, not play to look busy, and that starts with one sharp choice: what does winning actually look like in your game? When you name a real winning aspiration, you stop “prioritizing” and start eliminating, because the win becomes a constraint that earns you the right to say no.
Most strategic planning sessions don’t collapse inside the room.
They collapse right after.
Because the meeting ends with a list, and the list feels like progress. People go home thinking, “At least we have direction.” Then Tuesday shows up, and the list becomes optional.
If you’ve been there, you know the quiet frustration. You worked hard to plan, but you didn’t get the relief that planning promised.
So you try again next quarter.
Same venue. Same energy. Same outcome.
Now let’s name what’s really happening.
You didn’t lack initiative. You lacked a clear win.
That’s why the first question matters more than people think.
What’s our winning aspiration?
Why teams skip it
They skip it because it sounds like vision.
And leaders are tired of vision.
They’ve seen lofty statements that look great in a slide deck but don’t guide decisions in real work. So when someone asks about aspiration, the room gently avoids it. “Too high-level,” someone says. Then everyone runs toward what feels practical—projects, targets, timelines.
That move is understandable.
It’s also the moment the planning session quietly becomes Planning Theater.
Because when you don’t define winning, every idea sounds reasonable. And when every idea sounds reasonable, nobody has the courage to drop anything.
So you “prioritize” without really choosing. You end up funding too many things halfway.
Playing to Win is a good start. But it’s not the finish line.
I like Playing to Win because it puts strategy back where it belongs: in choices, not documents.
It reminds leaders that strategy is a set of choices about how you will win, and it begins with the win you’re aiming for.
But I want to go beyond the definition. I want to help people feel the consequence of that question.
A winning aspiration is not just a statement. It is a Bold Bet.
It is a decision to narrow your game on purpose. And the moment you narrow the game, something else becomes true.
You will have to let go.
Aspiration is not poetry. It’s a constraint.
A useful winning aspiration does two jobs at the same time. It points the team forward, yes. But more importantly, it puts walls around the work.
Those walls are what save you on Tuesday.
Because Tuesday is when temptation arrives. A big client asks for something outside your direction. A senior leader pushes a pet project. A new opportunity shows up and looks shiny. People start saying, “Maybe we can do both.”
Without a constraint, you will. And then you wonder why execution feels heavy.
So here’s a pause worth taking.
If you keep doing strategy the way you’ve been doing it, what will your organization look like one year from now?
More focused?
Or just more tired?
What “winning aspiration” really sounds like
Winning is not “to grow.”
Winning is not “to be world-class.”
Winning is not “to deliver excellence.”
Those are safe sentences. They don’t force a tradeoff. They don’t protect your calendar. They don’t change what gets funded.
Winning is a position.
It is what you want to become known for in a specific game, with specific people, under specific conditions, in a way that makes you the Obvious Choice.
Once that becomes clear, a strange thing happens.
Your list starts shrinking without you trying to shrink it. Because the aspiration begins choosing for you.
Example 1: A resort in Boracay
Imagine you own a resort in Boracay.
The business is okay, but you feel the pressure. Everyone is competing. Everyone is discounting. Everyone claims “great service.” Your team decides to do a planning session, and every department brings a list.
Marketing wants ads. Operations wants renovations. Sales wants partnerships. HR wants training. Someone suggests adding a café. Someone suggests hosting more events. Someone suggests a new tour package. The list grows fast, and the conversation becomes negotiation.
Now watch what happens when you ask the aspiration question first.
Here’s a winning aspiration that makes a Bold Bet:
“We will win by becoming the Obvious Choice for couples who want a quiet, design-forward, adults-only escape in Boracay.”
That one sentence begins trimming the list.
You don’t need projects that attract loud group bookings. You probably shouldn’t chase big barkada packages, even if they fill rooms fast. You don’t need a bigger function hall. You don’t need to say yes to every partnership that brings traffic.
Instead, the “right” work becomes obvious.
Renovations now mean soundproofing, room design, and private spaces. Training now means anticipation and personalization, not generic hospitality scripts. Marketing becomes story and aesthetic, not discounts. Partnerships become aligned with calm, not chaos.
You didn’t “prioritize.” You eliminated.
And elimination is the beginning of strategy.
Example 2: A winning aspiration for an LGU
Now switch contexts.
You’re part of an LGU. You do annual planning. You have the same pain, just with different labels: too many programs, too many requests, too many stakeholders, too many “urgent” needs.
Your strategic plan becomes thick. Your outcomes feel thin.
Now imagine an aspiration that is a Bold Bet:
“We will win by becoming the easiest municipality in our province to start and grow a small business—fast permits, clear rules, no fixer culture, and a government that helps you succeed.”
That aspiration changes the conversation immediately.
You stop measuring success by how many programs you launched. You start measuring success by whether a citizen can start a business without begging, waiting, or guessing.
The big moves become clearer, too.
You build a one-stop process that actually works. You simplify requirements. You standardize timelines. You train frontliners to solve problems instead of redirecting people. You build a simple tracking system so citizens can see progress without chasing.
Then the harder part shows up, and it should.
What do you stop?
You stop launching scattered projects that look good in photos but don’t change citizen experience. You stop adding “new” programs that your team can’t sustain. You stop spreading resources thin just to make everyone feel included.
This is where leadership lives. Because a real aspiration will disappoint someone.
But it will serve many.
The real job of aspiration is to earn the right to say no
Some leaders avoid aspiration because it feels risky.
“What if we miss opportunities?” they ask.
You will miss some.
That’s the point.
Because the bigger risk is not missing opportunities. The bigger risk is missing your future while staying busy.
When you chase too many things, you don’t just get tired. You become average at the few things that could have made you the obvious choice.
In a competitive world, average is expensive.
My own winning aspiration
Let me make this personal.
In the Philippines, there are many strategic planning facilitators. Most of them are sincere. But the traditional approach often leads to outputs that are complicated, confusing, and useless in the messiness of real work.
Teams leave with a thick plan, but not with sharper decisions.
That’s the pattern I’m pushing against.
So here’s my own winning aspiration:
“To become the Obvious Choice for CEOs who want to make Bold Bets—few choices that create focus, force tradeoffs, and build the capabilities to win—so their teams stop planning theater and start choosing.”
That aspiration is also a constraint on me.
It means I won’t run sessions that end in laundry lists. I won’t hide behind complicated frameworks. I won’t deliver a beautiful document that nobody uses on Tuesday.
Because that would make me part of the problem I’m trying to solve.
A quick exercise you can teach: The Aspiration Sprint
You can run this in 30 minutes in a meeting, even without slides.
Start by asking each leader to draft one sentence privately. You want independent thinking before group consensus dilutes it.
Use this simple pattern: “We will win by becoming the Obvious Choice for ___ in ___ because ___.”
After everyone shares, don’t merge the sentences yet. Instead, ask one question that forces clarity.
“Which version, if true, would make it easier to say no?”
Now move to the courage part.
Ask the team to write three sentences that begin with “We will stop…” This is where aspiration becomes a Bold Bet, not a slogan. If nothing can be stopped, the aspiration is still soft.
Then finish with the Tuesday test.
Ask, “What would we say no to next Tuesday because of this?”
If the room can answer, you have something usable.
If the room can’t, don’t rush forward. Stay there. That discomfort is the work.
One last pause
Look at your current plan.
If you removed the logo and title, would a stranger know what game you’re trying to win?
Or would it read like a collection of responsible activities?
If you continue planning the same way, you will continue getting the same result.
More meetings. More lists. More motion.
Less progress.
So start where strategy actually starts.
Ask the question most teams skip.
What’s our winning aspiration?
Then let it constrain you. Because the moment your aspiration becomes a boundary, your strategy stops being a document. It becomes a decision system.
And that’s what you need when Tuesday comes.
