A Guide for Planning your Next Retreat

A retreat is an opportunity to engender creativity. It is a chance to think about what ought to be and to devise steps to get there. This article shares tips on planning a successful, fun, and results-oriented retreat.

People work hard and want their work to be meaningful. They need to see that what they do each day moves their organization or team in a desired direction. Moreover, people are more productive and motivated when they feel a sense of involvement in establishing their organization’s goals and ideals.

A carefully planned retreat motivates employees by enlisting their creative participation. Effective retreats produce concrete approaches for tackling long-standing and difficult organizational problems.

Whether you are planning a retreat for a very large and complex organization including hundreds of staff, or a team of 12, the following steps will help you have a successful, results-oriented retreat.

Identify and Communicate the Purpose of the Retreat

Think carefully about your retreat purpose because it becomes the foundation for the retreat design. Consult with key leaders when considering possible purposes.

Retreats can be used to:

  • Engage in a planning process.
  • Build a more effective team.
  • Take stock of progress in a project or with organizational change initiatives.
  • Engender creativity and synergy around problems or future directions.
  • Create a degree of shared ownership in key planning issues, or in solutions to organizational problems.
  • Discuss issues at a much deeper and more thoughtful level.
  • Allow people who work remotely the opportunity to connect.

The retreat is one step in a continuing process to establish or sustain an effective organization or team. Retreat processes and results must be carefully planned to fit in with ongoing activities and the normal workload.

Leaders must be persistent in communicating about retreat goals, managing expectations about what the retreat intends to accomplish, and ensuring follow up with key action items. Without this clarity, retreats often fail.  

Select a Facilitator

Choose a leader or outside professional to facilitate the retreat.

The facilitator must:

  • Have experience identifying the significant and appropriate items for discussion.
  • Be an extremely good listener.
  • Be an effective discussion leader, asking open-ended questions and getting a variety of people participating.
  • Help achieve concrete results that fit into a larger organizational process.

If you decide on an outside facilitator, that person should be involved in the early planning stages.

It’s best to consider an outside facilitator when:

  • Getting decisions made or problems solved is harder due to a large group. Specifically, if there are more than 20 participants, the retreat members include more than staff, or if it is unusual for the individuals in the group to meet.
  • The leader wants to participate fully rather than running the meeting.
  • There are warring factions in the group, and part of the purpose is to reduce or manage these conflicts more effectively. Outside help promotes a sense of neutrality.
  • Creating participation is not one of the leader’s strengths.
  • You want help to develop the agenda, facilitate the meeting, and stimulate and assess progress with follow-up activities.

Develop the Agenda

Ways to seek input to inform the development of the agenda:

  • Identify the salient issues and organize them in an order suitable for the time allotted.
  • Survey key people. Use a series of open-ended questions (e.g., “what are the issues with…”), or a series of scaled questions (“rank the following issues on a 1-5scale”).
  • Use a planning committee that includes a cross section of staff. The committee should have 5-8people and a clearly defined role and timeline (e.g., to plan the retreat, give advice on key issues, or react to your plans).
  • Have the facilitator interview a cross-section of people or members of the planning committee.

An experienced facilitator can help to design the agenda by offering guidance on how to mix different methodologies, allocate time, and make sure that different activities build on one another and move the group toward achieving the goals.

Retreats can last anywhere from a half day to three days and include a combination of activities, like small and large group discussions, team games, simulations, or short training components. Learnings from one kind of activity can contribute to other activities. For example, if conflict has been identified as a problem, include a conflict management skill building exercise.

Decide Who to Invite

The purpose and retreat agenda determine who should be invited. If the goal is for the leadership team to reach agreement on the direction for next year, then it might make sense to limit participation to leadership. If the goal is to increase staff input and participation, you’ll need a wider invitation list.

Deciding who comes and who does not come is difficult. Between eight and twenty people is best for a productive retreat. When the numbers get larger than 25, it is a good idea to get some professional facilitation help for the design and delivery.

The decision about who does and does not come, and what message it sends, needs to be carefully considered. You can build in agenda time when all staff participate, and other times when certain groupings participate, given the issues at hand. Generally, it is better to err on the side of too many than to omit someone or some group that may be critical for future team effectiveness.

Share Retreat Expectations

It is better to focus on a few agenda items, and do them well, rather than on many items and address them superficially. Explain how the time will be balanced between producing concrete outcomes that make a difference to the organization on an operational level (e.g., future planning, a change initiative, leadership issues) and reconnecting with one another to influence the capacity to work together (e.g., building a team, increasing participation, having fun). This is especially important as people work more virtually in organizations.

Finalize and communicate these expectations.  

Choose a Site

Having fun at a retreat is important. Choose an environment that allows for a “work hard – play hard” mentality.

Ideally, a retreat site should be away from the "normal" workplace and work pressures. The amount that gets done at an off-site retreat setting is more than at one held in the office. Informal settings encourage people to be open and clear with one another. Social time (e.g., breaks, meals, planned social events) provide time for people to discuss controversial topics and pave the way for subsequent discussions.

If there are budgetary restrictions, find a conference room that is outside the office. Consider hotels, a conference facility, or a local university. If you must stay in the office, use a conference room that you normally do not use. If possible, the conference room should have windows, comfortable chairs, and enough room for smaller groups to work.