Why Strategic Planning Fails — And What Strategy + Planning Should Look Like

You bring your leadership team to a hotel for strategic planning. The room is cold. The coffee is hot. There’s a nice backdrop with your theme. You sit through presentations, SWOT, breakout groups. You debate targets. You agree on “strategic initiatives.”

Everyone goes home tired, with a deck or binder that looks impressive.

Fast-forward three months.

People are busy. Firefighting is back. The “strategic plan” is somewhere in Google Drive.

And if you’re very honest with yourself, you’ll admit: We did a lot of planning. But did our strategy really change?

Hold that question. We’ll come back to it.

This guide explains planning. But if you’re leading a team and need a winning strategy, go here: strategy

The Hotel Ritual We Call Strategic Planning

I know this ritual very well because I’ve been on both sides of it.

For years, I was hired to facilitate strategic planning workshops for companies, schools, LGUs, and government agencies. We’d go to Tagaytay, Baguio, Batangas—anywhere with good air and a function room.

We followed the usual pattern.

We called it “strategic planning,” but underneath, the mental model was simple:

Strategy = big tasks. Tactics = smaller tasks that support the big tasks.

So we’d define “big strategies” like:

• “Improve customer service”
• “Strengthen our people”
• “Go digital”
• “Increase revenue by 20%”

Then we’d break them down into programs, projects, and activities.

Each year, we’d add a little more. A bit more training. A bit more automation. A bit more expansion.

The plan got bigger every year. But the organization didn’t always get sharper.

That bothered me.

I’d see a CEO who looked happy on Day 3 of the workshop… and then looked exactly the same one year later, saying, “We need another strategic planning, things aren’t moving.”

At first I thought, “Maybe they just don’t execute.” Over time, I realized something else: The way we think about strategic planning is too safe.

It lets us look serious and professional, without forcing us to make the kind of choices that actually change how we play the game.

How My Own Thinking Shifted

The more I watched this pattern, the more uncomfortable I became with my own work.

I started asking myself:

• Are we helping them win, or are we just helping them organize tasks?
• Are we designing strategy, or nicer plans with the word “strategic” on top?

I began studying people like Roger Martin and his work on Playing to Win. His definition of strategy as an integrated set of choices resonated with me.

He wasn’t talking about big tasks. He was talking about where you choose to play and how you choose to win.

That was a turning point.

I stopped seeing strategic planning as a big annual workshop. I started seeing it as something that should sit inside a bigger system:

Strategy (Decide) + Plan (Design) + Execution (Drive) reviewed and adjusted through a Strategy Cycle—usually every quarter.

And because I’m me, I stopped calling what I do “workshops.”

Workshops are the format. What I want is Shift Experiences—sessions designed to create actual shifts in how leaders think, decide, and act.

Strategies must shift. It’s not a list of tasks.

Let’s go deeper into what usually goes wrong.

The Three Hidden Problems with Traditional Strategic Planning

1. Strategy is treated as a list of big tasks.

In most strategic planning sessions, “strategy” is explained as the big things we want to achieve in the next 3–5 years.

It sounds like this:

• “Our strategy is to expand nationwide.”
• “Our strategy is to be customer-centric.”
• “Our strategy is to go digital.”

Then, suddenly, you have “strategies” for everything.

The problem? These are directions, not decisions.

If strategy is just a set of big tasks:

• You never really choose where not to play.
• You never really choose how you will specifically win.
• You can always add more. Walang natatanggal.

Real strategy feels very different. It forces you to say:

• “We will serve these customers first, not everyone.”
• “We will compete this way, even if it means we’re not the cheapest.”
• “We will drop these projects because they dilute our focus.”

That’s not how most strategic planning workshops are structured. They are built to include more, not to choose less.

2. Strategy is treated as fixed, so the plan gets heavier.

Visit a government agency that has gone through strategic planning for years.

You’ll often see a very familiar pattern:

There’s a 5-year plan that lives in a binder or PDF. Every year, they “review” it and then add more:

• New programs to show responsiveness
• New performance indicators
• New committees

The assumption is:

“Our strategy is already set. We just need to improve the plan.”

So no one asks:

• “Should we still serve all these sectors?”
• “Are we spreading ourselves too thin?”
• “Is this still the best way to deliver our mandate?”

They just ask, “What can we add this year?”

The same thing happens in the private sector.

A bank sets a “strategy” to be the “leading bank in X segment.” Each year they add more digital projects, more branches, more campaigns.

But very few people sit down and say:

“Given what we’ve learned from our customers and competitors this year, is this still the smartest game to play?”

Strategy becomes a static label. The plan becomes a heavier backpack.

3. The output is documentation, not decisive moves.

Most strategic planning workshops are designed to produce a report.

There is a closing presentation. There are summary slides. There is an “output.”

But ask this simple question:

“After that workshop, what became non-negotiable and what became off the table?”

If the answer is blurry, what you have is not a strategy. You have a collection of wishes.

A strategy document is useful only if:

• It clarifies the game you’re playing.
• It explains how you intend to win that game.
• It guides what you stop doing, not just what you start doing.

Traditional strategic planning is safer than this. It lets you sound ambitious, without forcing you to disappoint anyone.

Real strategy will always disappoint someone. That’s one way you know it’s real.

A Plan Is Not a Strategy (And That’s Good News)

Here’s the shift that helped me—and my clients—make sense of all this.

I started separating three jobs:

• Strategy is how you decide.
• Planning is how you design.
• Execution is how you drive.

Those three words—decide, design, drive—changed how I run “strategic planning” forever.

Let’s make it concrete with examples.

Strategy: Decide the game you want to win.

Imagine a logistics company serving Luzon, Visayas, and Mindanao.

For years, their “strategy” was: “Serve more customers and grow volume nationwide.”

Every year, they did strategic planning and added projects—more warehouses, more routes, more promos.

When we worked together, we asked a different set of questions:

• “In which region do we win most easily?”
• “What kind of customers value us the most?”
• “If we had to pick one part of the business to dominate for the next three years, which would it be?”

They realized something awkward. They were excellent at serving mid-sized e-commerce sellers in NCR and nearby provinces. They were average or losing money in far-flung routes.

So the strategic choice became:

“For the next 3–5 years, we will play to win with mid-sized e-commerce sellers in Luzon. We will be the fastest and most reliable partner for them.”

That meant saying no to some geographic expansion. It meant designing offers specifically for those sellers.

Same company. Same trucks. Different choices.

That’s strategy.

Now a government example.

A city health office has a mandate to “serve all.” That sounds noble. But practically, they are overwhelmed.

When we asked:

• “Which health problems cause the most suffering here?”
• “Which communities are most at risk?”
• “If we could only move the needle in one area this year, what should it be?”

They chose to focus on:

“Reducing preventable complications in pregnant women and newborns in three high-risk barangays.”

That’s strategy too. It’s not a “big task.” It’s a set of choices about where to focus their limited resources.

Planning: Design the work so people can actually do it.

Once you’ve decided your game, you still need a plan.

Planning is where you answer:

• What do we do first?
• Who does what?
• What does success look like in 12–18 months?
• What will we commit to in just the next 90 days?

Let’s go back to the logistics company.

After deciding to focus on mid-sized e-commerce sellers in Luzon, the planning questions shifted:

• “What 1–3 outcomes must we achieve in the next 12–18 months?” For example: “Be the #1 preferred logistics partner of 200 mid-sized e-commerce sellers in Luzon.”
• “How will we measure that we’re winning?” They chose things like on-time delivery rate for that segment, retention, and share of wallet.
• “What 3–5 initiatives will make this happen?” Not 27. Just a handful—like redesigning their onboarding for new sellers, upgrading tracking for that segment, and re-training frontliners for that specific experience.

Now the city health office.

They chose to focus on pregnant women and newborns in three barangays. Their planning shifted from “let’s have more programs” to “What are the three most important moves for this specific group in the next 12 months?”

The plan became lighter, more focused, more human.

Planning is where you design the work so your people can actually deliver, not drown.

Execution: Drive the work, then listen to reality.

Execution is where we often become unfair. When targets aren’t met, we blame “poor execution.” Sometimes that’s true. Many times, it’s incomplete.

Execution is where reality talks back.

Your logistics company launches its initiatives. Then:

• A competitor drops prices aggressively.
• Fuel costs spike.
• New regulations add delays.

Your city health office runs its focused programs. Then:

• A pandemic hits.
• Funding is delayed.
• Key staff get reassigned.

At this point, the question is not just, “Why didn’t we execute the plan?”

A more powerful question is:

“Given what we now know, is our strategy still the best bet, and is our plan still the best design?”

This is where execution and learning come together.

Which leads to the last piece.

Stop Treating Strategy as a Once-a-Year Event

Most organizations think of strategy only during strategic planning—once a year, maybe once every two.

The rest of the time, they live in:

• Operations reviews
• Problem-solving
• Puting-baga mode

What’s missing is a regular strategy conversation.

Not a long, fancy workshop. A focused Strategy Cycle.

Here’s the simple rhythm I now help teams build:

• Decide the strategy clearly.
• Design a focused plan.
• Drive the work.
• Then every quarter, sit down and ask:

“What did the last 90 days teach us? Are we still playing the right game? What should we bet on next?”

I call these sessions Strategy Shift Experiences.

Yes, they’re still workshops in format. We still meet in rooms. We still use pens and boards and post-its.

But I design them so that something actually shifts:

• A belief about what “strategy” is.
• A decision about where not to play.
• A commitment about what the team will protect for the next 90 days.

The output is not just a document. It’s a team that thinks differently.

From Workshops to Shift Experiences

People still call and say, “Sir Jef, can you run our strategic planning workshop?”

My answer is “Yes, I still do workshops. And I design them as Shift Experiences.”

A workshop is what we do. A Shift Experience is what we expect.

In a Shift Experience, we don’t just fill templates. We challenge assumptions. We don’t just list more tasks. We choose what really matters. We don’t treat strategy as something you fix once. We treat it as something you revisit regularly, with courage.

When we talk about private companies, LGUs, government agencies—iba-iba ang context, but the pattern is the same:

• You cannot afford to treat strategy as a static poster.
• You cannot keep adding to the plan without sharpening the choices.
• You cannot rely on one big annual workshop to carry a whole year of execution.

You need Strategy + Planning + Execution held together by a Strategy Cycle.

So Where Does “Strategic Planning” Fit Now?

I don’t throw away the term.

People still search for strategic planning in the Philippines. Boards still ask for strategic planning sessions. HR still books strategic planning facilitators.

I honor that language. But I change what happens in the room.

When I’m invited to do “strategic planning,” what we actually do is:

• Help you Decide on a real strategy: where to play and how to win.
• Help you Design a simple, focused plan that respects those choices.
• Set you up to Drive execution with a quarterly Strategy Cycle.

You still get your workshop. You still get your documents.

But you walk away with:

• A clearer game.
• Bolder choices.
• A team that knows how to revisit those choices, not just repeat last year’s template.

If You’re Tired of the Same Planning Ritual

If you’ve been doing strategic planning for years and you feel:

• “We’re busy, but not really moving,” or
• “We have plans, but I’m not sure we have a strategy,”

you’re not alone.

The old way of thinking about strategic planning made sense in a slower world. Today, it’s not enough.

You don’t have to abandon planning. You don’t have to burn your old binders.

You just need to put things in the right order:

Decide the strategy. Design the plan. Drive the execution. Review and shift regularly.

That’s the work I do now with leaders in the Philippines— in private companies, schools, and government.

We still meet in rooms. We still write on boards. We still laugh, argue, and get tired after long days.

But when people go home, something in them has shifted.

And that, more than any binder, is what makes strategy worth doing.

Strategy

Updated on 01/04/2026

Shift Experiences

Updated on 12/27/2025