Stop the Christmas tree strategy. Make bold choices. Win.
A Christmas tree strategy is when every leader adds a “must-do” initiative—until the plan is overloaded and execution collapses.
Jef Menguin facilitates strategy workshops that prevent that:
clear choices, real trade-offs, and the discipline to say no—so the organization can win.
So you don’t leave with a decorated deck. You leave with a strategy your team can actually run.
Who this is for
You’re not here because you need someone to “run a strategic planning process.”
You’re here because you already did that. You already ran the offsite. You already filled the templates. You already produced a plan that looked complete.
Now you want something that goes beyond the document.
You want a strategy workshop that forces choices and trade-offs, because the market won’t wait for your three-year timeline. You want a facilitation experience that helps leaders stop playing safe, stop adding more, and start choosing what will actually help the organization win.
If that’s the kind of workshop you’re looking for, you’re in the right place.
When a “good” plan feels like a loss
I once got invited to deliver an inspirational talk on the last afternoon of a company’s three-day strategic planning. I arrived early, and the department presentations finished faster than expected—almost like everyone wanted to escape the room.
Then the VP, Ramon, walked to the front and took the microphone. He looked tired. He sounded angry. Three months earlier, they had hired five consultants who introduced tools, frameworks, and templates. Ramon reminded everyone of that investment, then asked the question nobody wanted to face: “So where did it go?”
Because what he just heard wasn’t strategy. It was reporting.
Each department showed numbers that were ten percent higher than last year. Nobody challenged the slides. Nobody pushed back. Everyone stayed polite, because polite keeps you safe. But Ramon didn’t come for “better than last year.” He came for choices that would help them win in a market that was already changing.
Have you sat in a room like that?
You want clarity, but you get comfort. You want a path to win, but you get a plan that keeps everyone included. The deck looks complete, yet the organization still plays same-same.
That’s how you end up with a Christmas tree strategy—a plan overloaded with “must-do” initiatives, where everyone adds an ornament and nobody takes one down. It helps teams survive the meeting. It rarely helps the organization win.
If your strategy avoids trade-offs, what are you really doing—planning to win, or planning to stay safe?
Why the usual workshop fails
Most strategy workshops reward completion, not courage.
Leaders follow the steps, use the tools, and fill in the boxes. The session looks organized, so everyone feels productive. But the room never demands the one thing strategy needs: trade-offs.
That’s how planning turns into a parade of department presentations. Each team reports numbers a bit higher than last year, adds a few initiatives, and calls it progress. Leaders don’t challenge the slides because they also don’t want to be challenged. So the safest move is to nod, agree, and move on.
This is where the Christmas tree strategy shows up—and why it’s anti-strategy.
Everyone hangs a “must-do” ornament on the plan. Marketing adds theirs. Operations adds theirs. HR adds theirs. IT adds theirs. The tree looks full, so it feels like alignment. But nobody removes anything, so nothing becomes truly important. The plan gains weight but loses direction.
Strategy should reduce. It should cut. It should choose.
A Christmas tree plan does the opposite. It keeps everything to keep everyone happy. It avoids conflict inside the room, then creates chaos outside it. Execution collapses because the organization tries to do too much, at the same time, with the same people.
And because the strategy has no sharp edges, the frontlines can’t repeat it. They don’t know what to prioritize when trade-offs hit—which means they default to urgency, politics, and habit.
That’s not playing to win.
That’s playing to survive.
Stop building strategy like construction
A Christmas tree strategy happens when leaders treat strategy like construction.
They think, “If we build the plan carefully enough, the organization will follow it.” So they add initiatives the way you add floors to a building—one on top of another—until the structure looks impressive.
Then reality shows up.
In one strategy session I facilitated, we audited the initiatives from two years ago. The room went quiet when we saw the numbers. Some initiatives were used by less than 10% of leaders—and even fewer employees. A few people didn’t even know certain tools existed, even though the company had already paid for them.
Then we looked at subscriptions.
They had services that added friction instead of reducing work. Employees avoided them because they created more steps, more clicks, more overwhelm. But the company kept paying—millions every month—for tools nobody loved and few people used.
That’s not strategy. That’s a construction site you forgot to shut down.
When you treat strategy as “build it once, then implement,” you keep stacking. You rarely remove. You carry yesterday’s initiatives into today’s reality, even when they leak money and no longer support a clear winning aspiration.
A real strategy works like a decision system, not a building plan.
It forces you to ask, repeatedly: What are we keeping? What are we killing? What will we fund because it helps us win—and what will we stop because it doesn’t?
That’s how you move from playing to survive to playing to win.
The 5 questions that force real strategy
Once you stop treating strategy like construction, you need a simpler way to decide.
That’s why Jef Menguin uses the Playing to Win framework. Not because it’s fancy, but because it forces what most workshops avoid: choices and trade-offs.
Here are the five questions we work through—together, in the room:
1) What is our winning aspiration?
What does “winning” actually mean for us—now? Not a slogan. A clear aim.
2) Where will we play?
Which customers, markets, segments, channels, or arenas will we focus on—and which will we stop chasing?
3) How will we win?
What will make us meaningfully better in those arenas? What’s our edge?
4) What capabilities must be in place?
What do we need to build or strengthen so the strategy isn’t just wishful thinking?
5) What management systems do we need?
What rhythms, measures, and decision rules will keep this strategy alive after the workshop?
If you can’t answer these in plain language, you don’t have a strategy yet.
You have a Christmas tree plan—busy, decorated, and heavy.
These five questions cut through that weight and help your leadership team choose how to win.
What happens in the room
Picture a mid-sized Filipino company—let’s call them BayanTech. They’re growing fast, losing good people, and feeling pressure from bigger players. So the leadership team comes into the workshop with a familiar instinct: “We need to do a lot.” Better pay. More perks. A new LMS. A culture program. Another engagement app. Leadership training. Employer branding. Career paths. AI tools. All at once.
On the first hour, you can feel it in the room. Everyone has something they want to protect. Everyone has a slide, a pet initiative, a story about why their idea matters. It’s a Christmas tree waiting to happen.
So we don’t start with presentations.
We start with a wall of reality.
We put up what’s already running: programs, tools, subscriptions, initiatives, “projects that never die.” We ask simple questions that feel slightly uncomfortable: Who uses this? What problem does it solve? What decision does it support? What does it cost—money, time, attention? People usually discover duplicates. Or a tool nobody remembers. Or a subscription that quietly drains cash while employees avoid it because it adds friction.
Then the room shifts. Leaders stop pitching. They start noticing.
Next, we force clarity using the Playing to Win questions, but we do it in a way that makes thinking easier than pretending.
We get specific about the winning aspiration. Not “best employer.” Not “world-class culture.” Something you can actually test in the next 90 days: What kind of people do we want to attract? What kind of people do we refuse to lose? What must become true for them to stay and thrive here?
Then we move to where to play. This is where BayanTech usually pauses. Because “keep the best people” sounds like it applies to everyone—until you ask, Which roles and segments matter most to our win? Suddenly the team sees the trade-off: you can’t build a premium employee experience for everyone at the same level, at the same time, with the same resources.
After that, we make the hardest move: how to win.
Not “more programs.” Not “more benefits.” We ask, What will make us meaningfully better than alternatives for the people we need most? Maybe it’s speed of growth. Maybe it’s quality of managers. Maybe it’s project ownership. Maybe it’s flexibility with standards. Whatever it is, we turn it into choices that can guide decisions.
And then we do the part most strategy sessions avoid: we kill things.
We don’t call it “killing” to be dramatic. We call it freeing capacity. We set a rule in the room: If we add one, we remove one. Leaders put their pet initiatives on the table with everyone watching. They decide what stays, what pauses, what gets redesigned, and what ends. You can almost see shoulders drop when the list gets shorter. Less guilt. More focus.
Finally, we install a strategy rhythm, because strategy collapses when it has no cadence. We define how decisions get revisited, what gets measured, what gets reviewed monthly, and what gets adjusted quarterly—so BayanTech doesn’t fall back into survival mode the moment the workshop ends.
By the end, leaders don’t just “agree.” They can explain the strategy in plain language. They can point to the trade-offs. They can defend what they said no to. And they leave with fewer moving parts—so the organization can actually win with the people they have.
What changes after the workshop
The first change is quiet.
Leaders stop talking about strategy like it’s a document. They start using it like a filter. In meetings, you hear different questions: “Does this help us win?” “What are we trading off?” “If we say yes, what do we stop?” The room gets less polite, but more honest. Decisions get cleaner.
The second change shows up in the work.
The initiative list shrinks. Not because people become lazy, but because leaders finally protect focus. Projects stop competing for attention. Teams stop launching “nice-to-haves” that drain time and morale. People feel relief because the organization stops asking them to do everything at once.
The third change hits the frontlines.
They start hearing strategy in plain language. Not as a long deck, not as abstract “pillars,” but as choices they can repeat: This is where we play. This is how we win. This is what matters this quarter. When trade-offs arrive—as they always do—frontliners don’t freeze. They decide faster because leaders gave them a spine to follow.
And then the most important change: the organization builds a rhythm.
Instead of one big annual planning event, leaders revisit choices regularly. They learn what works, cut what doesn’t, and adjust without panic. That’s when strategy starts compounding—not as a plan you hope survives, but as a practice your leaders actually run.
That’s the difference between playing to survive and playing to win.
What you walk away with
You don’t leave with “workshop notes.” You leave with decision artifacts your leaders can actually use.
You walk out with a clear statement of what winning means for you right now—simple enough to repeat, specific enough to guide choices. You also leave with defined where-to-play boundaries, so the organization stops chasing everything and starts protecting focus.
You get explicit trade-offs in writing: what you will fund, what you will pause, and what you will kill. This is the part that removes the Christmas tree ornaments and frees capacity for the bets that matter.
You also leave with a practical execution bridge: a short list of priorities, the measures that will tell you if you’re winning, and the first 90-day push so the strategy doesn’t wait for “perfect conditions.”
And if you choose Strategy Rhythm, you leave with the operating cadence—agenda templates, review questions, and decision rules—so the strategy stays alive in monthly and quarterly conversations, not just in an annual retreat.
Proof from Strategy Workshops in Manila, Philippines
In many strategy workshops in Manila, I see the same before-and-after shift. Teams walk in with a long list of initiatives and walk out with fewer, clearer bets—because they finally make the trade-offs they avoided in past planning sessions. The best proof isn’t a prettier deck. It’s a shorter list that people can actually execute.
I’ve also watched leadership teams in the Philippines discover hidden leaks during a strategy workshop: tools and programs launched years ago, used by fewer than ten percent, still draining time and subscription fees every month. When leaders can’t link an initiative to a winning aspiration, the room stops defending it. They cut it, free capacity, and reinvest in what helps them win.
The strongest proof shows up after the workshop, not during it. In the next meeting, leaders start asking better questions—“What are we choosing?” “What are we trading off?” “Does this help us win?”—and the strategy becomes clear enough for frontliners to follow.
If you want to run this kind of session internally, I can share the materials leaders use in my strategy workshops in the Philippines—the decision prompts, trade-off worksheets, and strategy rhythm templates that help teams produce clear choices without drowning in frameworks.
Book a Strategy Discovery Call (Manila / Philippines)
If you’re already looking for a strategy workshop facilitator in the Philippines, the fastest way to know if we’re a fit is a short call.
In 20 minutes, we’ll clarify what you’re trying to win, what’s getting in the way, and which kind of strategy work you need right now—Bold Bets, Game Plan, or Strategy Rhythm.
Come as you are. No deck needed. If you already have a plan, bring it. If you don’t, bring the messy reality. We’ll work with what’s real.
And if I’m not the right facilitator for your team, I’ll tell you straight.
Or email: leadership@jefmenguin.com
About Jef Menguin
Jef Menguin is a strategy workshop facilitator in the Philippines who helps leadership teams choose how to win—using the Playing to Win questions as a practical decision tool, not a lecture.
He doesn’t run strategy like a yearly event. He facilitates it as a repeatable practice: clarify the win, make bold choices, expose trade-offs, and remove the Christmas tree ornaments that slow execution.
Jef works with teams in Manila and across the Philippines who want strategy that people can explain, defend, and actually run—especially when the market changes and comfort stops working.
FAQ
Do you facilitate strategy workshops in Manila?
Yes. I facilitate strategy workshops in Manila and work with teams across the Philippines.
How long is the Strategy Discovery Call?
About 20 minutes. Enough to clarify your goal, your current reality, and the best starting point.
Do we need to prepare a deck?
No. If you have existing plans or presentations, bring them. If you don’t, bring the messy reality. We’ll work from what’s true.
Will you teach a strategy course during the workshop?
No. This is not classroom training. The workshop uses exercises and decision prompts that make strategic thinking easier by doing the work in the room.
What should we expect at the end of the workshop?
Clear choices, visible trade-offs, and usable outputs—so leaders can explain the strategy and run it after the session.
What’s the difference between Bold Bets, Game Plan, and Strategy Rhythm?
Bold Bets clarifies the big choices. Game Plan turns choices into a focused execution plan. Strategy Rhythm installs the cadence to review, learn, and adapt.
Can you help us stop initiatives that no longer work?
Yes. Part of good strategy is saying no. We surface initiative overload, identify money/time leaks, and make trade-offs explicit.
Ready to stop playing safe?
If you want a strategy workshop in Manila or anywhere in the Philippines that forces bold choices, real trade-offs, and a strategy your team can actually run, let’s talk.