For most organizations, the start of a new year signals a time for assessment and planning. Disciplined organizations will do this via a strategic planning retreat. While these are sometimes informal sessions, more often they are conducted in a structured environment away from the office. In this appropriated environment, stakeholders can have a frank, solutions-minded conversation about the issues and opportunities facing the company.

To be productive, these sessions demand a high degree of candor from every participant. That requirement raises the question of the appropriateness and role of the organization’s leader. Should the leader attend the strategic planning retreat? Should he or she be in the room? If so, should the leader direct the conversation or even have a voice in the discussions?

We argue that a leader should be involved in a strategic planning retreat, provided he or she is there as an equal participant and not a facilitator. As with anything, there are pros and cons to this consideration. Weighing them can give you the best sense of what questions and conversations are necessary to set up the session and the leader for success.

Tip Checklist Strategic Planning Retreat Leader

Generally, if the leader is primarily responsible for approving decisions that others will own, it is not necessary for them to be a part of the session. However, that is rare. Leaders usually bear a lot of responsibility for approving strategy and implementing ideas and solutions – making them essential to a strategic planning retreat.

The question then becomes how to ensure they inspire productive discussions and outcomes, rather than inhibiting honesty and squelching creativity. You can employ a very straightforward facilitation technique to encourage the leader to embrace his or her role.


The Facilitation Approach to Preparing a Leader for a Strategy Session

During the pre-session interview with the leader, ask the leader to agree to participate in a specific way as follows. 


During the session, I think it would be very helpful if you would permit your people to state their opinions first before you state your views. On any particular issue, please avoid being the first, second or even the third person to speak.

If you can add support to a position, feel free to state the support and indicate why. If you can add support to multiple positions, this is even better because it encourages the team members to look at all sides. But again, allow others to state their opinions before giving yours. If the group seems to be missing an idea, after several have spoken, please feel free to add your ideas.

The key here is that we want the group to know that you are participating, but not driving. Will this work for you?



It will indeed. I am very interested in seeing who speaks up and who doesn’t.

In most situations where a member of our team has helped an organization to prepare for a strategic planning retreat, laying the groundwork with a simple conversation like this one is positive and offers useful guidance for the leader.

Our team is available to help you prepare for and conduct your strategy sessions. Please Contact Us, chat us, or call us at 1-800-824-2850.