Top 10 Mistakes Leaders Make When Convening An Off-Site Meeting or Retreat

Kristin Arnold, one of North America’s most accomplished professional meeting facilitators, is part of CEO Trusted Advisers, a new service from Chief Executive Group connecting CEO-recommended experts in strategy, talent, operations, technology, finance and M&A, family business, personal effectiveness, and more with leaders of mid-sized businesses. Learn More: ceotrustedadvisers.com

Bob, the CEO of a $400 million manufacturing company, decided to bring his leadership team together for a two-day off-site retreat. He determined who needed to attend, what topics they needed to cover, and handed it over to his executive assistant (EA) to arrange the details.

Sounds like a great plan, right? Wrong. Bob is headed for a marginally successful meeting. If he took a bit of time to avoid these ten common mistakes executives make, he could achieve extraordinary results with a high degree of commitment to the resulting plan, course of action, or major decision.

Let’s review these common mistakes and what you can do to avoid them at your next off-site retreat:

Mistake 1. Create a Topical Agenda

Most CEOs like Bob have a general idea of what they want to cover and describe it to the EA, who then puts together a “topical agenda.” Whoa! So, what’s the mistake? We all know that having a clear, concise agenda is the key to more effective meetings. True, having a topical agenda is better than none, but it’s not going to get you the clear, definitive results you and your team are striving for.

Instead, create a results-oriented agenda with clear objectives and deliverables. For example, you can talk about “increasing sales” or you can create a “plan to increase sales 10% in six months.” Huge difference in the focus of the conversation.

Mistake 2. Ratify Your Decision

If you have already made up your mind on the course, direction, outcomes, and plans, don’t ask the team what they think. What happens if they don’t agree with you? Are you willing to change your mind?

If the answer is still no, don’t ask the team to simply ratify your decision. Be transparent by informing the group of your decision. Share the logic and reasons for making that specific decision, what your concerns are, and then ask for their help in implementing it.

Mistake 3. Invite Everyone

It is easy to bring in the entire cast of characters – absolutely everyone who touches the various topics on the agenda. It is much harder to strike the right balance of people. Each person you invite costs the company – in wages, opportunity costs, and increased meeting complexity. While the optimal group size is between 6-13 attendees, executives tend to invite a far greater number “just in case.”

Who absolutely needs to be in the room for the entire meeting? It is probably a core group – your direct reports, people you consider to be your “leadership team,” and other key stakeholders critical to the meeting objectives. Everyone else can be put on “standby” to dial or video in remotely. If you just need them there for a portion of the meeting, coordinate the time frames so they arrive just in time to participate.

Mistake 4. Pick a Bad Day

The date(s) might work for you, but your staff may be closing out the books or frantically trying to meet a deadline. Mondays, Fridays, and holidays are lousy because people are either coming back from or looking forward to the weekend.

It’s tough to find a date that works for everyone, but at least try. For example, you can accommodate your team by starting with lunch on Monday or leaving at lunch on Friday.

Mistake 5. Meet Onsite or a Poor Site

For important, high stakes meetings where you need to leverage the creativity of the group, deepen the team’s relationships, and achieve concrete deliverables, don’t stay in the office or hold the meeting in your facility.

The off-site retreat is an opportunity to be laser focused on the most important aspects of your company – to work “on” vs. “in” your business. By going off site, you are sending a strong signal to cut the ties from day-to-day activities and focus on the big picture.

I continue to be amazed at how much the ambiance of the room contributes (or detracts) from the team’s efficiency, productivity, and creativity. When selecting a venue, make sure the room is conducive to great conversation. It should have a few windows (no mirrors, please!) and a place to step outside to see nature and breathe the fresh air. You may also want to check with the venue as to what other events or company meetings are scheduled at the same time. I was facilitating an event at a hotel with a church revival being held in the next room. Loud and joyous singing and clapping kept erupting through the thin wall separating our rooms. It was hard to focus for those few hours!

Mistake 6. Talk at the Team

With such a small group, the point of an off-site retreat is to have meaningful conversations where everyone participates, and no one dominates. This includes the chief executive and guest speakers who kick off the event. If you are going to bring in a guest speaker, make sure the speaker is engaging and relevant. This person sets the tone for the entire event, so you want it to be inspiring, uplifting, and meaningful – the fewer slides (if any) the better, especially for the kick-off speaker,

Unfortunately, you don’t have time to bring your people up to speed and then have a conversation. Send out the PowerPoint slides, spreadsheets, and other stultifying documents ahead of time. Make it clear that you expect them to read these documents in preparation for the off-site retreat. And when the time comes to discuss them, do NOT punt back to get everyone up to speed. Sure, you might take a few moments to highlight the key points, but then move immediately into discussion. A word of caution: If your audience is used to being spoon-fed information, it might take a few meetings for them to get the message that they need to transform themselves into participants.

Mistake 7. Expect Too Much

One of the great benefits of having an off-site retreat is for everyone to be on the same sheet of music. Just handing out the sheet music and expecting everyone to play brilliantly is expecting too much. Furthermore, many executives stuff three days of work into a one-day off-site retreat and then everyone gets frustrated.

Set reasonable expectations, accounting for the fact that people need to process through and discuss the issues. When you take the time to discuss the 5Ws and the H (why, what, who, when, where, and how), your speed of implementation increases dramatically.

Mistake 8. Wander All Over the Map

Executive teams love to strategize, take a deep dive into the details, wander off into a rabbit trail, and crawl around in the bug dirt – all on the same topic! In fact, you already have a good sense of what could go wrong, so why not try to prevent these problems?

Develop some simple ground rules that make the team’s expectations known to all. My favorite is “All participate…no one dominate.”

Create a process agenda that allows the group to stay focused on the conversation at hand with the desired outcome in mind. A good facilitator can devise a smooth process to help you stay focused and achieve your outcomes and deliverables.

Mistake 9. Abruptly End the Meeting

Because you have crammed too much work into the amount of time allotted and wandered all over the map, you have run out of time. The meeting needs to end, but there is still more to do. People start packing up their belongings and you abruptly end the meeting. Unfortunately, you did not crystallize the next steps.

Retreats are often like Chinese food – it tastes great in the moment, but leaves you feeling hungry hours later. Conclude each topical conversation with a series of “So what? Now what?” questions. Make sure you have clear expectations of who is going to do what and by when. Then, if you have time (and you will because you have been following a realistic, results-oriented agenda), conclude the day with a summary of the work accomplished, along with the next steps to continue the conversation.

Mistake 10. Appoint Action Items

As items are discussed, the CEO may direct one of the attendees to take an item for action. There are two problems with this:

First, the CEO might be having a “sticky bun” moment where he/she is literally saying, “I want sticky buns for breakfast at the off-site retreat,” but what she really means is, “I want breakfast options – like sticky buns – at the off-site retreat.”

Second, the appointee might not be the right person and/or not too thrilled about getting that assignment!

Rather than appoint someone, clarify the action item first. Make sure the entire team understands what the task is – and then ask for a volunteer. Even though you know who should accept this assignment, wait patiently for a volunteer. You will have a greater probability of success if you let someone speak up. It becomes a public declaration not only to you, but to their peers – which is a powerful motivator. If you are unsure of the person’s skill or ability, ask if anyone would like to assist. (Perhaps it can be a developmental opportunity!) Keep that “volunteer” as your point person to ensure the task gets done.

By handing off responsibility for the off-site retreat to the ever-capable EA, the executive distances him/herself from the desired outcomes and typically commits some, if not all, of these common mistakes. Yes, your EA can handle the logistical details, but stay involved in the development of the agenda, selection of site, presenters and facilitator, as well as the process flow of the meeting. You will achieve the desired results with a high degree of commitment to the resulting plan, course of action, or major decision.

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Kristin Arnold is one of Chief Executive Group’s CEO Trusted Advisers topic experts. CEO Trusted Advisers is a service that provides CEOs access to a select group of peer-recommended, thoroughly vetted subject matter experts who can help close skills and information gaps and, ultimately, improve job performance and company profitability. Learn more at ceotrustedadvisers.com or contact managing director Scott Budd: [email protected] / 203-889-4981