The Best Way to Have a Strategy Retreat

The best way to have a strategy retreat may be quite different than you think it is. Rather than focusing on actual strategy development, it’s better to treat it as an intense strategy workshop aimed at personal growth and competence development.

Why Conventional Strategy Retreats Don’t Work

Strategy retreats are one of the most common events to create and formulate new strategy. They typically go like this:

Once every year, the leaders of a company go to a nice hotel for a day or so. During that day, they do some serious work in the morning, at least including a SWOT and post-it notes, and in the afternoon, or the next day, there is a fun team-building exercise.

Afterward, participants go home full of energy and optimism. The next day, everyone goes back to work and forgets about the retreat until next year’s retreat comes around.

Of course, I may be sketching too much of a stereotype here, but in too many cases it’s not too far off reality. This means that the common way to do strategy retreats is not effective. Why? For five reasons:

1. It disconnects strategy from everyday business. What is presented as a key strength—that they are held off site—is actually a weakness. It literally disconnects strategy from normal business and thereby makes strategy something extraordinary, which it isn’t, or shouldn’t be.
2. Not everyone who should be can be there. Strategy retreats create a divide between those who are there (the elite) and those who are not (the rest). There is already a big gap between strategy and execution, and by taking one group of people elsewhere to discuss strategy, this gap is enlarged.
3. It is based on an illusion of knowledge. When you think about it, it is pretty absurd to assume that strategy can be made in one or a few days by a select group of people sitting in a room. Effective strategy-making requires constant interaction with the outside world—to listen and see, as well as to experiment and learn.
4. Good ideas don’t just pop up. Offsites are based on the idea that the best ideas come from short brainstorms and pressure-cooker workshops. While inspiring and fun, the best ideas usually don’t come up like that. They gradually build up over time and with experience. They emerge as a side effect of people’s day-to-day work.
5. Strategy is a continuous process, not an event. Offsites suggest that strategy-making is an event, with a clear beginning and end. Strategy is not like that at all. Making sure that your strategy is up-to-date on an ongoing basis, as well as executed effectively, requires a continuous approach to strategy. Retreats don’t provide that.

Bottomline: they can be fun and inspiring, but you can’t do serious strategy development during a retreat. You need a continuous and engaging process that makes strategy second nature to your organization

How to Have an Effective Strategy Retreat

One conclusion could be to avoid strategy retreats altogether. In their conventional form, that would definitely be my recommendation. But the energy generated by such a type of event is valuable, essential even, to get strategy going in an organization. So, what to do instead?

The main change is to change the focus of the retreat from actual strategy development, to a combined energizer, opening, training, and alignment workshop, with four main purposes:

Energizer: Inspirational and energy producing start of the strategy development process

One of the big strengths of a strategy retreat is the potential energy it can produce. By building up anticipation and making it a special day, you can generate the energy that can fuel the rest of the process. It is also your chance to make it evident something important is going to happen.

Opening: Helping people open up their minds and hearts so that they can fully engage in the process

To get a productive strategy and implementation process, you want all participants to open up and give their full selves. Working for an organization is a significant part of people’s lives and people have much more to bring than just do their job. A good strategy retreat acknowledges and leverages this.

Training: Equipping participants with foundational knowledge and tools for strategy development

Competence development is critical for a successful strategy process. The better equipped people are, the better the process—and the outcome. Therefore, you want to spend a significant share of the retreat on training. This should be practice and application-based training, not just theory.

Alignment: Getting everyone on the same page on the strategy development process

Rather than creating alignment on the strategy itself, you want to create alignment on the process of getting there. By outlining the process and way of working, plus the tools that will be used, you create a standardized way of working so that everyone involved knows what to expect and do.

Turn Your Retreat in a Strategy Reinvention Day

At Strategy.Inc we call this type of strategy retreat a Strategy Reinvention Day. It’s a day that serves exactly the four purposes described above: energizer, opening, training, and alignment. Without getting into the nitty-gritty details, we divide into into a morning session and an afternoon session;

Morning: North Star

In the morning, we focus on everyone’s personal North Star. The goal of this is to get everyone’s personal direction and core principles. It is a crucial self-awareness session in which participants discover together what drives them. It covers both developmental discovery (purpose, vision, values) as well as performance discovery (goals, strengths, mindsets, and habits).

If done well, this session excites and opens up all participants. It prepares them for a strategy journey that is not just a business exercise, but that inspires, touches, and moves them. It engages, aligns, and connects participants to fully commit to the strategy process that follows.

Afternoon: Strategy Sketch

In the afternoon, we make the transition from personal direction to the organizations’ direction. The first goal of this is learning to work with the Strategy Sketch, the core tool we always use during the strategy development process. It contains the ten core elements of strategy in a visual structured canvas and can be used both to assess the status quo as well as design new strategy.

The second goal is to kickstart the strategy development process through an intense reinvention session in which participants reinvent the future of their organization. This is not to say that the future should be disruptive, but by focusing on reinvention, participants further open up their minds for change and start seeing the possibility that the future may look very different from the present.

[Retreats] can be fun and inspiring, but you can’t do serious strategy development during a retreat. You need a continuous and engaging process that makes strategy second nature to your organization

What Happens After the Retreat?

By turning your strategy retreat into a Strategy Reinvention Day along these lines, you can truly energize, open up, train and align people. This will serve as a significant kickstart of the strategy and implementation process that follows.

As a standalone event it has its value. But, like any strategy retreat, the value will be limited and the effect will fade out soon. Therefore, it is essential to use the Strategy Reinvention Day as the start of a full strategy and implementation process. This means that the actual development, and thereafter implementation, will follow right after the retreat and have been planned already upfront.

For more information on the Strategy Reinvention Day, click here, DM me here on LinkedIn, or join us in person during the Strategy Reinvented Conference on April 10-11, 2025 in Amsterdam. See here for more information, registration and an early bird discount closing at the end of this month.

Further Reading

• Why Strategy Retreats Don't Work
• The Strategy Sketch
• The 7 main features of a Strategy-Driven Organization
• The 10 Business Elements of Apple
• What is a Good Strategy?