brainstorming session

After more than two years working remotely, hybrid, or cautiously in-person, some organizations are beginning to think about scheduling an offsite or “retreat.” And while many of these tend to take place in the fall, planning for them begins now, during the summer.

These off-campus gatherings often bring together senior staff with the purpose of thinking strategically and developing ideas and plans for the future. For many organizations, they are an internal affair, handled by current leadership or, sometimes, guided by a facilitator.

At the risk of appearing self-serving (!), I advise against using strictly in-house resources. That’s because a process that is simply “facilitated,” absent an objective (i.e., externally driven) strategic assessment at its foundation, may produce limited success in preparing for an evolving future.

As the late Bruce Henderson (founder of The Boston Consulting Group [BCG]) wrote more than 50 years ago:

“It is rare for any organization to generate sufficient pressure internally from the ranks to produce significant change in direction. To do so is likely to be regarded as a form of dissatisfaction with the organization’s leadership.”

Indeed, plans that come from internally driven exercises are likely to simply reinforce the status quo. Most of the organization is not in a position to see the needs for policy and organizational change until the optimal time for action has long passed.

At that point — when the need is so obvious that the whole organization can recognize it — competitive advantage in flexibility and speed of response have been lost.

The “Outsider” Advantage

A useful and candid analysis is best developed with the guidance of someone who can be solidly objective and even critical of the organization when needed. Otherwise, existing vulnerabilities can be left unaddressed. An internal person may be reluctant to present (assuming they even notice) challenges and weaknesses, lest they be seen as not “part of the team” or disloyal.

It’s important as well to have someone who can act as a filter for ruling out some suggestions that arise through the process — something that must be handled delicately and based on objective reasoning.

For example, just last week I read an account of a university’s internally led planning process. The #1 issue that was surfaced? Parking. I’m sure parking may be an issue of concern for this small-town university, but I highly doubt it rises to the level of strategy in the challenging world of higher education. An external voice would have certainly moved this to the back burner.

Key Steps

To ensure that your offsite or strategy retreat is worthy of the time and resources involved, here are a few suggestions…

Prepare in advance.

When I work with organizations, I always start with individual or small-group interviews that are “not for attribution.” Most are one-on-one, so that everyone is heard and nobody is crowded out by the louder voices that inevitably emerge in a group setting. This degree of anonymity allows for candid and objective observations from a broad range of stakeholders.

Next, I look at internal reporting on critical issues to make sure that objective facts — not anecdotal opinions — are part of the process. (Note: The plural of anecdote is not “data.”) I then round this out with secondary research on the field or industry in question, which helps to understand how others are seeing trends or challenges.

Taken together, this preparation allows for the creation of a briefing document — or sometimes an introductory presentation — to provide context for the discussion.

Identify critical issues.

Never head into an offsite with a blank sheet of paper. Rather, use your prework to identify a few key questions that are core to the business and plan sessions specifically guided to addressing those items.

The more specific you can be in your questions, the better. For example, rather than “How do we grow?” a better starting point is “How do we continue growth in area X which is facing increased competition?” Better questions lead to better discussions and, ultimately, more worthwhile actions.

Allow time for closure and take-aways.

Sometimes, clear decisions can be made at the conclusion of the meetings. That’s fine — there is power to doing just that and informing the attendees.

Other decisions may require further consideration, perhaps even addressing new questions that arose from the discussions. In those cases, use the final session to let the participants know what decisions are being considered, how they will be determined, and how (and when!) you will communicate back to the group.

In general, leave enough time at the end for people to process and consider the ideas brought forward during the discussions.

Communicate a summary and implications.

It’s important to provide follow-up relatively soon after the event (a few days at most). That helps convey that leadership took the sessions seriously and that the matters discussed were important. Let the group know what decisions were made as a result of the sessions.

In cases where you decide not to go in a direction that was raised as a possibility, be sure to acknowledge that fact and provide your rationale. It’s important that group members feel their feedback was considered, even if it is not acted upon. They will be much more amenable to your decisions if they know that their views were heard.


Strategic offsites, whether held in person or virtually, are a very useful tool — but only if you spend the time and effort required to address a focused set of critical questions, preferably led by a well prepared and unbiased outsider.

A candid and objective assessment of the situation — warts and all — is absolutely necessary if you want to produce more than just an extension of the status quo. (Hint: you do!)


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