Planning and Implementing Retreats: A

Leader’s Guide
A retreat is an opportunity to engender creativity -- a time to remove your nose from the
grindstone and look to the hills, a chance to think about what ought to be -- and devise steps
to get there.

Most people work hard in their organizations and want their work to be meaningful — they
want to be involved and work toward an ideal. Even in the face of conflicting demands and
increasing pressures, they need to see that what they do every day moves their organization or
team in a desired direction.

Employees are more productive and motivated when they feel a greater sense of involvement
in establishing their organization’s goals and ideals. A carefully-planned retreat motivates
employees because it enlists their creative participation in setting goals and contributing to
decisions. Just as important, effective retreats produce concrete approaches for tackling long-
standing and difficult organizational problems.

While there is a general sense that retreats can be useful, people have had widely varying
experiences with them. One reason for the mixed reviews is clear: Leaders often
underestimate the complexity of preparing for and conducting a retreat.

This paper will address the various issues and actions you as a leader must address in
planning and carrying out a retreat. Whether you are the leader of a very large and complex
organization including hundreds of staff, or a team leader with 12 team members, we hope it
can help you attain the vision described above, and ensure you that you have a successful,
results-oriented retreat.

Planning a Retreat: Key Steps

1. Identifying and Communicating about the Retreat Purpose(s)

A retreat may have one, two or several purposes. It’s important to think carefully and clearly
about retreat purposes since they become the foundation for the retreat design. In considering
possible retreat purposes, you can as a leader consult with a leadership team or other key
leaders – formal or informal – within your organization or team.

Retreats can be used to:

 engage in a planning process that involves all the major units or contributors
 build a more effective team in an office or organization
 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 than they can in the
“controlled chaos” of the office environment
  allow people who telecommute or who are located in different geographical regions or
who travel a lot the opportunity to re-connect.

No matter what the purpose for the retreat, everyone must understand that the retreat is not an
end in itself. It is simply one step among many 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.

And you as a leader must be very persistent in communicating about retreat goals, managing
expectations, and ensuring follow up with any key retreat action items. The most compelling
reason for retreat failures is the lack clarity about purpose and what the organization or team
is really trying to accomplish by having a retreat. As such, it is critical to share the purposes
with participants and help set expectations about what the retreat intends to accomplish.

2. Deciding on a Retreat Facilitator

You can choose to lead the retreat yourself, appoint a retreat committee, or to bring in an
outside facilitator. If you decide on an outside facilitator, that person should be involved in
the early planning stages.

There are several occasions when it’s best for you to consider outside help. For example:

 It’s difficult to achieve a high level of participation with large groups. Getting
decisions made or problems solved is harder than it might initially appear. An outside
facilitator is helpful if there are 20 or more people involved, if the retreat members
include more than staff, or if it is unusual for the individuals in the group to meet
together.
 A facilitator is useful when you as team or organizational leader want to participate
fully in substantive programmatic or management issues and not worry about running
the meeting. This is especially true if you are going to be taking an advocacy role at
various times of the meeting.
 Enlisting the help of an outsider is appropriate when there are warring factions in the
group, and at least part of the reason for the retreat is to reduce or manage these
conflicts more effectively. Outside help promotes a sense of neutrality that may help
clarify and reduce the conflict. You may, in fact, be neutral in a particular situation,
but people involved may not share that perception.
 You may decide that creating participation is not one of your strengths, and a
facilitator is necessary to get people fully involved. Once the level of participation is
increased during the retreat, you may be able to continue it at an appropriate level
back at the office.
 Facilitators can help develop the agenda, facilitate the meeting, and act as a catalyst
for stimulating and assessing progress with follow-up activities.
 Should you decide to engage a facilitator, what characteristics should you lookfor?
First, a facilitator can be an outside consultant or someone from within your
organization if it is large enough so they do not have much contact with your area, or
they are from a unit that has this as role mandate (some HR units have this). A good
facilitator should be experienced in helping teams deal with complicated issues in a
way that optimizes participation. The person doesn’t need a high level of substantive
experience with or knowledge of your technical Indeed, at times such knowledge may
 actually hinder a facilitator (who may, if not careful, get too involved in the subject of
the discussion).

The facilitator must have sufficient experience to tell which problems are significant and
appropriate for discussion at the retreat. The facilitator must also sense when a problem has
been discussed sufficiently, and to push for closure on it. The person needs to be an
extremely good listener and an effective discussion leader — asking open-ended questions,
and getting a variety of people participating and involved with responses.

Experienced and effective facilitators are bent on helping the organization achieve concrete
results, and they see the retreat as only part of a larger organizational process. If a candidate –
whether from outside or within the organization – does not exhibit this approach when
interviewed, it is perhaps best to seek other facilitators.

Once you decide on the facilitator, the next steps are: developing the agenda, deciding on
who is to attend, creating expectations about the retreat for the team or organization, and
finding a suitable site.

3. Developing the Agenda

There are a variety of ways to seek input that can help inform the development of the agenda:

 You can identify what you think are the salient issues for the retreat, and organize
them in an order suitable for the time allotted.
 Key people or a random sample of staff can be surveyed using a simple and practical
electronic survey This instrument can have a series of open-ended questions (for
example, “what are the issues with…”), or a series of scaled questions (“rank the
following issues on a 1-5 scale”). The agenda can be based on, or at least influenced
by, the data produced through this process.
 You can call for a planning committee, or series of planning committees, that include
a cross-section of staff. Such a committee should have no more than 5-8 people on it,
and should have its role and timeline clearly defined (is it to plan the retreat, give
advice on key issues, or react to your plans). How such a committee actually gets used
is largely a question of leadership
 A cross-section of people can be interviewed by the outside facilitator, or if there is
none, by members of the planning committee (or by some combination).

If you have a smaller organization or team – say 10-15 people – it is not necessary to use all
four methods. Rather, you could do a survey of the team, and use that data to help inform
your choices about the final goals and agenda. Or, if you have engaged a facilitator, you
could have that person interview all or most of the staff, and use the data to help design the
retreat.

On the other hand, if you have a larger organization, the most effective approach is to
modestly combine all four of the agenda-development methods spelled out above.

These methods can provide very useful input and yet be economical, especially if realistic
resource limits are provided. For example, doing an e-survey can give overall good broad
input that can be very useful. Given a good cross-section of participants, it is likely that only
a representative sample need to be interviewed before the important issues become clear. A
planning committee only needs to meet a couple of times to inform the development of the
agenda.

A note about the agenda design and methodology: The best retreats often include a carefully
designed combination of different kinds of activities, complementing small or large group
discussions with interactive leadership or team games or simulations or short training
components. A good agenda usually features a mixture of these kinds of activities to help
keep things active for all participants and, if designed well, learning and discussions from one
kind of activity can contribute greatly to another activity. For example, if conflict has been
identified as a problem during the data gathering work, a part of the retreat might be devoted
to enhancing people’s conflict management skills, either via a short training session or by
using a conflict management simulation. An experienced facilitator can help in the agenda
design process to offer guidance on how best to mix different methodologies, how to allocate
time over the retreat period, and how to make sure that different activities build on one
another and move the group towards achieving the goals.

Whatever process you as leader end up choosing to help inform retreat design, a draft set of
goals and an agenda can be finalized and shared within the team or organization four weeks
or so in advance of the retreat. This process will also be very useful in determining who is to
participate for all or parts of the retreat.

4. Deciding Who Attends

The decision about who to invite to the retreat depends largely on the purposes and retreat
agenda. As part of the data gathering and agenda development process, decisions can be
made about participation. In general, retreat participants can vary from the CEO and senior
staff to all technical staff, or to everyone in the organization or office, or to a team leader and
an intact work team. If the goal is to make sure the leadership team reaches agreement on the
direction for next year, then it might make sense to limit participation to just that group. If the
goal is to increase staff input and participation, then it is logical to extend an invitation to a
greater number of people.

Deciding who should come is often difficult. Some departments or functions are quite large
— how many people can be at the retreat and still have it be productive? Ideally, between
eight and twenty people work best. However, organizations or groups are often larger than
that. If wider participation is desired, retreats can be held with 40 or 50 people, but they have
to be designed very carefully to succeed. Some mixture of small group activities and report-
outs to the large group is necessary here for effective output. When retreat numbers get over
25, it is a good idea to get some professional facilitator help for the design or delivery stage,
or both.

Another difficult aspect of the “who comes” decision should be entitled “who does not
come.” Once you make a decision to have a retreat that includes people beyond the senior
staff, it sometimes becomes difficult to draw the lines — just senior technical leaders? Those
who are termed ‘professional’ staff? What about support staff? There are no right answers
here, but the decision about who does not come, what that implies, what message it sends,
needs to be carefully considered. If there are already tensions between groupings within the
organization, will inviting – or not inviting – make those divisions better or worse? Another
possibility is to build into the agenda times when all staff may be participating, and other
times when certain groupings may 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.

One last note here — participation decisions are often made based on conventional wisdom
or parochial suggestions. For example, the following logic suggested eliminating one office:
“We needn’t invite anyone from that division because they are not interested in marketing
discussions, and they don’t have much to contribute in that area.” Perhaps true, perhaps not.
But the manager in that case needs to consider whether that kind of vision is consistent with
his/her own agenda for the organization. The retreat can be used for consciousness raising, to
create new and different roles for individuals and divisions, and to help people rethink
linkages and interrelationships.

5. Finalizing and Communicating Retreat Expectations

After setting the agenda, it’s important to finalize and communicate expectations for the
organization or team, and there are two key factors to consider here. First, it is important to
be clear to people that it is better to focus on a few agenda items, and do them well, rather
than to focus on many items and address them superficially, or not finish some at all.

Second, it is important to decide on and communicate what you see as the balance during this
retreat between allowing for broad discussions, time for reconnecting (especially if the staff is
not co-located) and discussing specific operational issues. While retreat sessions that
produce concrete outcomes can make a real difference to the organization on an operational
level, the kind of substantive discussions across lines and reconnecting with one another can
engender relationships that influence positively the capacity to work together for months into
the future. This is especially important as people work more virtually in organizations, and
must rely on trust to interpret what is meant in an email or telephone or Skype
conversation. Thus it is important to emphasize that there is to be a balance between content
(for example, future plans, a change initiative, leadership issues for the team or office) and
process (for example, building a team, increasing participation, having fun).

6. Choosing a Site

In general, high performing teams are able to work hard and play hard. Having fun at a retreat
contributes to producing important results. Thoughtfully choosing an appropriate
environment will help ensure that the “work hard – play hard” ethic actually materializes.

Yet, finding a suitable spot is often left to the last minute — almost as an afterthought.
Ideally, a retreat site should be just that — a retreat away from the ‘normal’ workplace to a
place where people are truly free from routine work pressures. The amount of work that gets
done at an off-site retreat setting is significantly more than gets done at one held in the office.

If budgetary restrictions preclude an out-of-town site, then find a conference room that is
outside the office. In most cities, there are ample conference choices available, whether they
are in hotels, a conference facility, an unusual retreat facility (local universities or churches
sometimes have them). If necessary, you can meet in your office but perhaps 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. Another suggestion is to end the first day with some kind of
social event (a reception like gathering, a coffee or tea session, or whatever). All of these
arrangements help to indicate that it is not just business as usual.

Why is the site and environment so important? It’s critical to keep in mind that the informal
aspects of the retreat contribute measurably to work output. Serious issues are often discussed
at breaks, or at lunch, or dinner, or after dinner. The climate — more informal and
participatory — encourages people to be open and clear with one another in ways that the
office environment discourages. Even apparently meaningless social time contributes — for
example, a person will find that discussing something socially over lunch with another person
will help pave the way for a subsequent in-session discussion on a controversial topic.

Implementing the Retreat: Six Essential Elements

As part of the preparation process, you and/or the retreat planners should have identified clear
goals, an agenda, and a rough sense of timing for each agenda item. (Retreats may last
anywhere from a half day to three days.) In addition to the preparation work described above,
there are six essential elements for effective retreat implementation.

1. After introductory getting started activities, you as leader need to begin with a well-
planned opening presentation. In this opening session, you need to articulate a clear
rationale for the retreat — including how the retreat can contribute to the unit or
team’s agenda for the next year or so. You need to stress the importance of the retreat
and that it is but one part of your leadership approach in renewing and sustaining an
effective organization and team. You can then state your expectations of retreat
behaviour (“full participation” or “open exploration of these ideas” or “advice to me
so I can make these particular strategic decisions” or whatever); it also needs to be
stressed that interruptions will be kept to a minimum.
2. After the opening presentation, the retreat leader (you, the outside facilitator, or
planning committee member) needs to share the goals and the agenda for the retreat.
This should include some time for questions and any participant input to the final
agenda. Assuming there has been some data-gathering work done prior to the retreat,
the results should be shared at this time. Ideally, this is the time to communicate how
the issues identified during the pre-retreat data-gathering helped inform the final
retreat goals and agenda.
3. Once the framework and direction for the retreat has been firmly established, then the
agenda will usually include a number of substantive discussions or interactive
activities around clear topics or problems. If the retreat group is small (below 10 or
12), these discussions can be done almost entirely as one group. If the group is larger,
it’s important to combine small group and large group work. In situations like this,
small group work optimizes participation, and gets better, more substantive thinking.
At times, some participants may ask, “Why not just discuss things in the large group,
there are only 25 of us?” At this point, it is extremely important to push ahead with
the small group approach. In large groups usually only the most verbal participate —
the normally quieter people who may need time to think or an invitation to speak or
who do not like to interrupt are generally silent, and this is often a substantive loss to
discussion quality and input. Moreover, very large group discussions tend to hop
around in ways that almost preclude rigorous thought, effective listening and clear
agreements. To make these discussions fruitful, it is important for the retreat leader to
stress participation within time limits, and to provide clear small-group tasks if such a
 method is being used. Also, it is important to assign leaders and reporters, or to ask
the small groups to choose them.
4. The retreat facilitator must guide interactive activities or moderate discussions and
report outs. The facilitator needs to periodically check with the group to see that
things do not become “over-discussed” — he or she must be clear about helping the
group realize when discussion on an item is completed. The facilitator must also make
sure no one person is dominating the discussion, and help everyone who wants to
participate get a chance to do so. To the extent that input into decisions are an
important part of the retreat, you as the leader (whether or not you are also serving as
the facilitator) need to be clear when decisions are to be made, and how you are using
the group in the decision-making arena — to advise, to vote, to reach consensus, or to
provide input to you, who will then make the decisions at some later point.
5. The retreat facilitator must record key agreements as the retreat proceeds. Recording
decisions helps determine (a) whether agreements are real, and (b) that people are
clear about the agreements. It helps to publicly record these items using a laptop or a
flip chart or some other appropriate electronic device. Keeping them in view reminds
people of progress.
6. Near the end of the retreat, the retreat facilitator must review agreements, and — with
either the leader or the group’s input (or both) – prioritize actions that might result. As
part of this process, it is advisable to help the group limit the number of actions to
only those most important as everyone returns to a ‘normal’ workload and extra work
that is not of the highest priority often simply does not get done. Which in turn leads
the group to feel either they have failed or the retreat process failed when in fact it
may have been inadvisably unrealistic from the start.

Where there are high priority action items, the facilitator can help the leader and group assign
responsibility with time deadlines where appropriate. The more specific and trackable these
assignments are, the more likely these things will actually be accomplished after the retreat
ends. As one final check, this list needs to be reviewed, and tested for reality. In this final
review process, it is good to ask questions like the following, “Think of our regular workload
— can we do all these things and still get the work out? Are there things here that should take
priority over some of the regular work? Upon further reflection, should we eliminate or
temporarily shelve any of these items?

The Leader’s Role

There is one final element that needs special emphasis — your role as the leader. You need to
be a role model, and any actions that you take must be consistent with your normal leadership
style. Or, on the contrary, you might use your behaviour at the retreat to signal a slight (or not
so slight) change in leadership style. This obviously needs careful thought.

You may think that your role at the retreat is to be silent and listen. That is indeed part of it,
but you also need to register your views and lead the decision-making process. You must
participate fully, offering opinions without dominating, and sometimes waiting until near the
end of the discussion to contribute. Although it is appropriate to put an emphasis on
listening, if your retreat behaviour is completely out of character, the staff will think
something is wrong, and may view the proceedings as not being “real.” The difficult thing for
you, of course, is to maintain a balance, and share views while encouraging participation
from others.
It is also extremely important for you to avoid trying to indirectly steer the group so they get
“the right answer” or make the “correct” decision. If you know there is only one acceptable
answer on a particular topic, it is far better to state it from the outset, and not waste
everyone’s time creating the illusion of participation. People respect a leader’s own agenda or
“sacred cows,” but not if they feel they are being manipulated to agree. This of course means
you need to think carefully about what is truly open for discussion and what is not, and what
kind of input is needed for which issues.

Ensuring Appropriate Follow-up

To the extent that there are action items that emerge from the retreat, follow-up is very
important. Retreats are hard work, and they represent an important investment. Often,
expectations then get raised about progress, and about organizational change for the better. If
this progress — or at least some of it — does not materialize, people will often get more
disheartened than if the retreat had not happened at all.

A key step in the follow up process is to finalize responsibility and time deadlines for each of
the priority items (assuming some initial agreements during the last retreat sessions). One
way to do this is to meet with the people who volunteered (or were suggested) to carry
forward with particular items. At this meeting, you may decide to put some of the items on
hold, agreeing it is better to choose fewer items and accomplish them than to choose many
and fail.

Your continuing role involves reinforcing the need to accomplish the action items.

When one of the action items is accomplished, that act should be noticed and celebrated. This
is an instance where “cheerleading” is very appropriate. You can look for positive
accomplishments on an ongoing basis, and point out these accomplishments in public forums.

There is one almost foregone conclusion about retreat follow-up: if you do not take an active
role in tracking progress and reinforcing work on key action items, not much progress will
occur. The rush and priorities of everyday business will side-track the intentions of almost
everyone. Thus, your follow-up role is essential.

Summary — A Review of the Critical Steps

If you are an organizational or team leader and you are thinking about undertaking some sort
of retreat activity, this section is meant to be a review and checklist that should help you as
you manage the retreat process.

1. Well in advance (2 months or more) of the retreat dates, decide on the following:
o Identify and communicate about initial retreat purpose
o Decide on retreat facilitator
o Refine retreat purpose and develop the agenda; includes collecting data to
inform the development of the agenda — decide who does it, kinds of data to
be gathered, who on the staff contributes; consider possible use of planning
committee; check how the data collected has influenced goals and agenda;
examine the plans for realism — it is better to do fewer things well than many
superficially, or to leave things unfinished
 o Decide on who participates (which is easier if you are the leader of a relatively
small team) – if not, check your assumptions very carefully here so that
important groups do not unthinkingly get left out.
o Identify site you will use for the retreat; check availability.
o Manage expectations of the whole organization about the retreat.
2. Begin the retreat with a cogent opening statement which includes your sense of how
the retreat and retreat output fits your overall agenda.
3. Help lead (if you are not the facilitator) and participate in the retreat; be a role model;
make or help crystallize agreements as they evolve.
4. Review decisions, action items and responsibilities at the end; spell out plans for
follow-up. Follow-up on high priority action items; be a cheerleader, acknowledge
accomplishments, push when action is not forthcoming.