Leadership Off-Site 101: Part II — Early planning questions

This blog post is a part of a larger Facilitation collection that explores the various aspects of crafting and leading successful corporate events.

Part I of the Leadership Off-Site 101 series offers a basic background on the anatomy of leadership off-site design. This post, Part II, covers the topics you should consider at the very beginning of the planning process.

What is the context for the off-site?

Before you jump into execution and start firing out invitations or requesting quotes from meeting venues, pause. It always pays off to take a moment to step back and consider the context within which the off-site (on-site, workshop, retreat, meeting, etc.) is being convened.

Here are six questions I ask when a client is discussing an upcoming management event with me:

  1. Why now? — The answer to this question is often revealing. It invites comments on external and internal developments that prompt the need for a face-to-face meeting.

  2. What’s at stake? — This question clarifies the importance of the event and the degree of effort that is commensurate with what’s at stake.

  3. How urgent? A helpful question when the off-site is still in the idea stage and its timing has not yet been decided.

  4. How does this off-site fit in the overall process? Is this a regular event (e.g., annual strategy planning off-site, quarterly performance review) or a special event (e.g., kickoff of a major initiative)?

  5. What is the group’s experience with off-sites? — Prior experience shapes expectations, and you should be cognizant of those. For example, if every single off-site in the past had a heavy social component with a fun team-building experience, participants may be disappointed if you skip it this time.

  6. What else is happening that should be considered? — This is an open-ended question that often uncovers pragmatic considerations such as budget constraints or opportune timing. The question also allows you to anticipate top-of-mind concerns that may “hijack” the agenda.

What are the objectives of the off-site?

Once you appreciate the context of the leadership off-site, the next most important task is to help the sponsors of the event to articulate — and align on — what success looks like for the off-site.

In some cases, leaders have a very clear and shared vision of the outcomes they seek: what are the objectives of the off-site, what topics should be discussed, what decisions should be made, etc.
(Stay tuned: I will add a separate post with client examples to give you an idea of the breadth of objectives and topics and include a link here.)

More often than not, you need to help leaders advance their own thinking, agree on what the off-site is all about, or both. Guiding questions I find helpful are:

  • What does success look like?

  • What specific outcomes do you want to see?

  • What do you want participants to think, do, say, and feel at the end of the off-site?

  • What would be a good use of everyone’s time?

  • Which topics must be discussed?

  • Which decisions must be made?

  • Are these expectations realistic?

(Stay tuned: I will add a separate post with client examples on how sponsors have clarified their off-site objectives and include a link here.)

How close are we to achieving these objectives?

Conceptually speaking, if the objectives above give us a sense of “Where are we going?” then the next task is to understand “Where are we now?”

Tactically speaking, here I ask 3 broad questions:

  1. What is the current degree of alignment? — Where the desired outcome is a decision or team alignment, it is always useful to understand where the group is today. For example, if people are largely aligned around a specific topic, it makes little sense to allocate a lot of time on the agenda to deliberate it. On the other hand, if there is a contentious topic, then you should design an alignment process leading up to the off-site.

  2. What does this group need to make decisions or move to action? — This looks really different from client to client and requires further investigation:

    2.1. Who makes the decisions and how? — Sometimes, you have a single decision-maker who declares a path forward after consultation with colleagues. Other times, you have a small committee that reaches a decision jointly. And at other times still, you have many equal partners who must get on board.

    2.2. What is the “burden of proof” required to give executives enough conviction to make a call and follow through? — Some teams just scribble on a flip chart based on what they know off the top of their heads and are ready to decide. Others need sophisticated analyses under multiple scenarios.

    2.3. Do we need to equip everyone with a common fact base? — This is important in situations where leaders run fast in their own silos but lack basic insights into other parts of the organizations to be able to make joint decisions.

    2.4. Beyond the facts, how do we convince and energize decision-makers and key stakeholders? — I have had to tell compelling stories, produce videos, design war games, and use creative formats to generate the discussion that is needed for a specific group.

  3. What has already been done/will be done by the time of the off-site? — Obviously, if we need information, recommendations, or anything else for a productive off-site, it is important to understand what is already available or is underway — and what we would need to develop in the preparation process.

What are the basic parameters?

Next, before you delve into the substance of the off-site, it is a good idea to get 6 more general choices out the way:

  1. Location — Where will the event take place? It could be outside of the office (“off-site”) or on the premises (“on-site”). Both options have advantages and disadvantages. If on-site, which office should host the event? Often, there are sensitivities around holding all events at a company's headquarters and event sponsors take extra care to rotate locations across sites.

  2. Timing — When will the event take place?

  3. Duration — How long will the event be?

  4. Participants — Who will join for what part? And — more importantly — why?

  5. Mix of social vs. work use of time — Will there be any team-building activities built into the program?

  6. Event-planning support — Who is in charge of the myriad of logistics planning and on-site event support?

Again, it is helpful to understand what has already been decided on and what is still outstanding.

The next blog post delves into the substance of off-site design.
Disclaimer: While I am listing these questions in a neat linear fashion, in reality, the off-site design process is iterative and the design choices you make are interdependent, so do read ahead.

Explore more blog posts from this Facilitation collection to prepare for, and lead, a fantastic event.

Written by Aneta Key. Last edited March 2019.