On strategy retreats

Khalil Tarhouni
4 min readOct 13, 2021

Last month, we organized our second strategy retreat with Timsoft Group. In this post, I wanted to share some thoughts and takeaways from this retreat. What is a strategy retreat? Why and when we organize such event? Who are the people that should be involved? What are the good-case practices?

First time I came across the concept of strategy retreats or off-sites was 3 years ago when I was part for Endeavor. I heard several entrepreneurs sharing their experiences when it comes to hosting strategic-level meetings “outside of the building”. I found the concept very interesting, and I thought that it was specific to scale-ups or even startups. But when I joined Timsoft, a 17-year old, Tunisian but international, SME, one of the initiative I wanted to implement as Project Manager (the title doesn’t reflect my job description at that time) and Chief Marketing Officer was a strategy retreat.

Steven Stowell presents it this way:

“A strategy-focused retreat provides a designated time for team members to take a step back from normal activities, call ‘time out’ from putting out fires and responding to crisis, and take a focused look at the team’s direction.”

In this beautiful article on Forbes, the author talks about a:

strategy retreat — pause, breathe, retreat, transform, grow, repeat — is as important as a vacation for the business soul. This is your eat, pray, love moment for your company’s strategic success.”

In more practical terms, it’s a 2 to 3-day-event during which top and sometimes middle-management gather to talk strategy. The number and profiles of participants may vary from a retreat to another depending on the context the company is living. For example, our first retreat reunited the top management, 9 people and our second one extended invitation to 20 people including Business Unit Managers, Delivery Managers and Project Managers.

Thinking of the timing of retreats, they usually take place every year or every six months depending again on the context, the speed at which the company is growing, the changes that are occurring in the internal and external environment. And since the main topic here is strategy, it’s important to leave time for the decisions that were made in these events to bring some results. You don’t need a retreat every month. Speaking of which, strategy retreats are a great opportunity to discuss topics that we don’t have the luxury to touch on in our day-to-day work due to lack of time or focus.

Ideas are flowing and people are sharing thoughts and feedback about the trajectory that the company should take in the upcoming month or even years. Incredible atmosphere!

It goes without saying that — as for every important event — preparation is key. Who’s responsible for the agenda? Who delivers the sessions and facilitate workshops? Who takes care of the logistics? Well, depending on the company’s capacity and available resources. Companies might choose to outsource some components or decide to handle 100% of the event. In our case, I — Chief Growth Officer — was responsible for the agenda and sessions’ dispatching with the help of the CEO and CFO. The 3 years I spent with the students’ organization — AIESEC — taught me a lot about how to plan agendas and run conference. The most important thing — that comes before the agenda — is what we call the “flow”. Having a clear flow helps you structure your agenda. Obviously, the flow is the translation of the event’s objectives and desired outcomes. Once everything — Flow + Agenda — set, you just need to assign a session for the right profile within the team and support them in the preparation. For those who are doing it for the first time, you should work closely with them to ensure that the session outcomes are reached but also that your colleagues enjoy the exercise. One of the secrets to success is dry run. It’s important to do a walk-me-through-your-slides time and advise the responsible accordingly.

During the event, it’s important to set some ground rules related to communication, respect of the timing, respect other ideas, not taking things personally and so on. Notes takers and timekeepers are key to success and an opportunity to keep everyone involved.

Post event is as important as the event itself. Make sure you thank all the participants and consolidate the notes and takeaways in a short report. It is also crucial to deliver on what you promised and keep the feedback loop open. Follow-up, follow-up and follow-up.

Strategy retreat are a great source of energy and motivation for your team and you need to capitalize on this momentum. Participants should share their experience (except sensitive information) and spread this energy and motivation among the whole organization. If you are thinking of organizing a strategy retreat, initiate the conversation ahead of time, plan it and do it. The most important thing is that you start somewhere.