Why Most Strategic Planning Retreats Fail (Even When People Enjoy Them)

A few months ago, I was invited to give an “inspirational speech” to a group of skin care executives.

I arrived early, as I usually do, and the organizers let me sit in and watch the presentations of each business unit. This was the final day of their strategic planning retreat. For two days, they had team building, learning sessions, and fun activities. Now it was “presentation time.”

Each group went to the front, showed their slides, and walked everyone through their strategic plan. Forecasts. Targets. Campaign ideas. New numbers for next year.

When the last team finished, the Vice President stood up to give his closing remarks.

No one expected what happened next.

He was clearly frustrated. He told them that three months before, he had given them frameworks and tools they could use to build a solid, defensible strategy. He is an academic by training, so he cares about good thinking. He brought in speakers to talk about new trends in skin care. He made sure they had support.

He expected plans that showed how each unit was going to achieve their targets differently this time. They were aiming for a 10% increase in revenue.

But what he saw on the screen that day felt like a copy-paste.

Most teams simply repeated last year’s plan with slightly higher numbers. Same activities. Same channels. Same ideas. Just better projections.

He told them, in front of everyone, that this had been happening for three years. Every year, they spent time, money, and energy on a planning retreat. Every year, they talked about innovation. Every year, the final plans looked almost the same.

The room changed.

The happy retreat mood vanished. Many of the executives looked like students who just received a failing grade from a strict teacher. They had enjoyed the last two days, and now their “final exam” had gone badly.

Then it was my turn to speak.

I was supposed to give an inspirational talk. But the truth was, most people were not ready to be inspired. They were still shocked. Some were defensive. Others were quietly hurt.

And there was something else I had noticed while watching the presentations.

Most of the time, people weren’t really listening to each other. They were busy polishing their own slides, checking details, or rehearsing in their heads. They wanted their unit to look good.

It was a perfect picture of why many strategic planning retreats fail.

When Planning Becomes a Performance

In many organizations, especially in the Philippines, strategic planning has become a performance.

Teams prepare for weeks, sometimes months. They collect data. They fill up templates. They craft slides. They try to impress senior leaders. They rehearse.

Then they go to a resort or hotel. There are team-building games, inspirational talks, and group pictures. In the end, each unit presents its plan. People clap. Certificates are given.

From the outside, it looks like a serious process.

But inside, something is missing.

The focus is on presenting a plan, not on making real strategic choices.

Just like the skin care company, many teams simply take last year’s plan, adjust the numbers, add a few activities, and call it “strategy.” It feels safer that way. No one is offended. No one’s project is cut. No one’s budget is questioned.

On paper, it looks complete. In reality, very little has changed.

Have you seen this happen in your own organization? Have you ever sat in a planning presentation and thought, “This looks familiar… we did this last year”?

Too Much Data, Not Enough Decisions

Another reason these retreats fail is data overload.

Leaders are asked to bring:

market data,
competitor data,
financial data,
operational data,
customer data.

All of this can be useful, but there is a hidden danger. When leaders are overwhelmed with data, they often react in the wrong way.

Instead of letting go of things that are not working, they add more.

They think, “If I show more numbers, more projects, more activities, it will look like I did my homework.” So they build thicker plans.

The plan becomes a wall of information—but the real questions stay unanswered:

What will we stop doing?
Where will we focus?
How will we win differently this year?

In the end, the plan is heavier, but the strategy is not clearer.

Team Building, But Not Strategy Building

Here in the Philippines, many strategic planning events are mixed with team building and inspirational talks.

I understand why. Leaders want people to feel motivated. They want bonding. They want fun.

The problem is when almost all the energy goes into:

making the event enjoyable, and
preparing nice presentations,

and very little energy goes into:

facing tradeoffs,
saying no, and
deciding how to actually win.

In many organizations, the “strategic planning” is really just the final presentation of work done quietly over the past two months. The big conversations already happened in smaller rooms. The retreat becomes a show.

If that is the case, then we should not be surprised when Monday comes and nothing really changes.

The Real Work of Strategy (That Most Retreats Avoid)

Strategy, in the Playing to Win sense, is not a long plan. It is a set of choices about how you will win.

Those choices include:

What does winning mean for us?
Where will we play?
How will we win there?
What must we be great at?
What systems will we use to keep these choices alive?

Answering these questions honestly and clearly is hard work. It forces you to:

give up some markets, so you can serve others better,
drop some projects, so you can invest more in what matters,
accept that what worked five years ago might not work today.

Most strategic planning retreats fail because they avoid this hard work.

They talk around the questions. They use nice words. They create long lists of projects. But they do not change what leaders are willing to stop, or what they are truly committed to build.

The result? Next year looks almost exactly like the last year—just with higher targets.

A Simple Way to Tell If Your Retreat Is Failing

You don’t need a consultant to tell you if your strategic planning retreat is working or not. You can ask yourself a few simple questions:

After the retreat:

Can your leaders explain, in one or two sentences, how you plan to win?
Can they name specific things you will stop doing to focus on better work?
Can they point to a few key capabilities you are committed to build?
Do your regular meetings and metrics change because of the choices you made?

If the answer to most of these is “no,” then it doesn’t matter how good the food was, how fun the games were, or how nice the slides looked.

You had a planning retreat. But you did not really build a strategy.

Before You Book the Next Retreat, Do This First

The story of the skin care executives stayed with me. They had good people. They had access to good tools. They had new ideas from guest speakers.

But without real choices, the plans stayed the same.

That is why, before I design or guide any strategic planning experience now, I like to start with something very simple and very honest: a Strategy Audit.

I created a Strategy Audit Tool with 25 yes-or-no statements. It helps leaders see where they really are.

It asks questions like:

Do we have a clear and shared idea of what “winning” means for us?
Have we chosen where we will play—and where we will not?
Are we truly different in a way our customers can feel?
Have we actually said no to some projects because they don’t fit our strategy?
Are our capabilities, systems, and meetings aligned with our choices?

It only takes about ten to fifteen minutes to answer. But the conversations that follow can change how you design your next retreat.

Many leadership teams are surprised by their scores. They realize, “We are good at preparing plans and presentations, but not yet good at making and protecting real strategic choices.”

That realization is a good place to start.

Your Next Step

So before you spend on rooms, food, and printed materials for your next strategic planning retreat, I invite you to do one small thing.

Use the Strategy Audit Tool with your leadership team.

Let each leader answer the 25 statements honestly. Count your YES answers. Read the guide that explains what your score means.

Then sit together and discuss:

What did we notice?
Where are we strong?
Where are we pretending?
What needs to change in our next retreat so we actually build strategy, not just another plan?

If you want to see where your organization really stands—and avoid another “copy-paste” planning year—the Strategy Audit Tool is a simple, powerful starting point.

From there, you can design strategic planning retreats that people not only enjoy, but that truly change how you play to win.