Bold Bets™ (Strategy Workshop)

Stop carrying a strategy your team won’t carry with you.

You’ve been to strategic planning before. You gather the leaders. You plan. You agree. You leave the room hopeful.

Then the week hits.

Everyone gets “busy.” Decisions stall. Priorities pile up. Managers protect their own initiatives. And you—again—carry the plan alone.

Bold Bets is the strategy workshop that fixes that.

We pressure-test ideas, force real tradeoffs, and lock in a few bold choices your team can actually execute.

Bring your leadership team. Leave with a strategy they can defend and deliver.

The Real Problem: Planning Comes Too Early

Most strategic planning sessions don’t fail because your leaders didn’t work hard.

They fail because the session is built to produce a plan—not a strategy.

So you ask people for data, decks, targets, and projects.

And because everyone is trying to be “helpful,” the output becomes predictable:

More priorities.
More initiatives.
More “strategic” words that mean different things to different people.

When everything is included, nothing is chosen.

That’s why Monday wins.

People slide back to the old ways—because a plan without clear choices can’t survive real life. It can’t settle arguments. It can’t kill distractions. It can’t tell a manager what to stop doing.

Strategic planning works best as Stage 2. But most teams start there.

Bold Bets is Stage 1.

This is where you make the decisions your plan is supposed to serve—so planning becomes simple, and execution becomes possible.

What Bold Bets Does (That Planning Can’t)

Bold Bets doesn’t try to cover everything.

It helps your team choose what matters most.

Because strategy isn’t a list of good ideas. It’s the few decisions you’re willing to protect—especially when the pressure hits, and everyone wants to go back to “business as usual.”

In Bold Bets, we do three things:

1) Clarify what winning means
Not in slogans. In decision-ready language your leaders can use.

2) Cut the noise to a few bold bets
So teams stop competing for attention and start moving in one direction.

3) Give your organization one shared story
So managers stop improvising strategy—and confusing their people.

The result is simple:

Less noise.
Faster decisions.
A strategy your people can actually carry with you.

What Happens in the Room

This isn’t a lecture. It’s a pressure-tested working session.

We don’t reward the loudest voice.
We don’t collect everyone’s initiatives.
We don’t “align” by letting everything live.

We do the work leaders avoid because it feels uncomfortable:

We choose. We make bold bets.

Here’s the flow:

1) Diverge — surface the best ideas and the real issues
2) Converge — group patterns and sharpen options
3) Cut — pressure-test “nice” ideas that can’t win
4) Commit — lock in the few bets worth defending

By the end, your strategy isn’t hiding in a deck.

It’s visible. Speakable. And ready for Monday.

The 5 Bold Choices (Pressure-Tested)

We use Roger L. Martin’s Playing to Win as a guide for one reason: it treats strategy as choices.

But Bold Bets strategy workshop isn’t about the book. It’s about your team making decisions.

You don’t come here to produce a perfect plan.

You come here to build something more powerful: clarity, focus, and shared language—so when the world changes, your team doesn’t panic or scatter.

That’s what makes you agile.

Because when you’ve made the right choices, you can adjust the plan fast… without losing direction.

Here are the five bold choices you will pressure-test and lock in:

1) Winning Aspiration
What does “winning” look like—clear enough to lead decisions?

2) Where to Play
Where will we compete… and where will we stop playing?

3) How to Win
What advantage will make customers choose you—consistently?

4) Must-Have Capabilities
What do we need to build to make these bets winnable?

5) Management Systems
What routines and rules will keep the strategy alive after the workshop?

These aren’t discussion topics.

These are decisions that keep your team aligned when things get messy—so you can move faster, adapt quicker, and still win.

How the Bold Bets Workshop Becomes Real

A strategy workshop only works if the strategy leaves the room.

Because not everyone will be there.

That’s why Bold Bets is designed as an immersive experience with a before and after—so your leaders don’t just decide… they can also explain.

Before (Light Prep, High Clarity)

We ask for a few inputs so the session starts on truth, not guessing:

your current priorities list
your biggest strategic tensions (where you keep getting stuck)
key constraints we need to respect

No heavy homework. Just enough to make the room honest.

During (Immersive, Pressure-Tested)

This is where your team does the hard part:

surface options
debate tradeoffs
cut what can’t win
commit to the few bold bets worth defending

Not a lecture. A decision session.

After (So People Can Actually Follow)

You don’t just leave with decisions.

You leave with a way to communicate them:

a 3-page Strategy Communication Brief your leaders can share
a clear “what we chose / what we’re not doing / what this means for you” message
manager talking points so leaders can cascade the strategy without improvising it

Because a strategy you can’t explain is a strategy you can’t execute.

Who Bold Bets Is For

Bold Bets is for leadership teams who feel the drag of “too many priorities” every single week.

You’re doing a lot. But focus keeps slipping. And decisions keep getting slower.

This is for you if:

Your strategic planning turns into a long list of projects—with no real tradeoffs
Your leaders “align” politely, then go back to protecting their own initiatives
You keep revisiting the same debates because there’s no clear choice to anchor them
Your managers interpret strategy differently—and your people feel the confusion
The market keeps shifting and you need a strategy that helps you adapt without losing direction

If your team can’t answer the same question the same way—start here.

Where We Run Bold Bets Strategy Workshop

Bold Bets is available for leadership teams across the Philippines.

We typically run sessions in Metro Manila, Laguna, Cavite, Batangas, and nearby provinces—and we also deliver it onsite anywhere your team can gather.

Prefer online? We can run Bold Bets virtually for distributed leadership teams.

Tell us your location. We’ll suggest the best format.

FAQs (The Real Questions Leaders Ask)

So… is this strategic planning?

Not in the traditional sense. This comes before planning. Bold Bets Strategy Workshop is where you make the choices first—so planning becomes simpler and faster.

What if our leaders don’t agree?

Good. Disagreement is usually a sign the choices aren’t clear yet. We surface the tensions, pressure-test assumptions, and help the team land on decisions they can defend—not just polite “alignment.”

We already have a strategic plan. Do we still need this?

Many plans are packed with initiatives but light on choices. Bold Bets helps you check: Do we have a strategy inside this plan? If yes, great—you’ll sharpen it. If not, you’ll finally know what to cut and what to commit to.

Will this work in a messy, fast-changing environment?

That’s exactly why it works. Plans change. A clear strategy gives you a stable direction—so when conditions shift, you can adjust quickly without losing focus.

How many people is ideal?

Usually 5–12 decision-makers. Small enough to decide, big enough to represent the real work.

What do we need to prepare?

Light prep: your current priorities list, key constraints, and the few tensions you keep debating. No heavy templates. No long homework.

What do we get after the workshop?

A 3-page Strategy Communication Brief plus key talking points—so leaders can cascade the strategy to people who weren’t in the room, without improvising it.

What happens next, if we want follow-through?

Bold Bets can stand alone. If you want to translate it into a one-year plan and install weekly execution cadence, we can guide the next steps afterward.