Do's and Don'ts for Team Offsite Meetings

Do's and don'ts for offsite meetings

Its offsite season. The year is half finished and we’re starting to get picture of how things are going. Are we on track? Are we going to hit our numbers? Do we need to make changes? Is the team performing as we’d like it? It feels like there is still enough time to make adjustments and revise plans if needed … but not much time.

If your team is doing well, the offsite meeting is a chance to celebrate wins and build on momentum. If your team is struggling, it’s a chance to offer some tough love, make some changes and reset with a positive mindset.

I’ve been to my fair share of lousy offsite meetings. To be honest, I carried a healthy dose of cynicism about them for many years. Endless presentations, awkward team building exercises, forced fun, faux alignment, excessive amounts of coffee and croissants. It all just seemed so contrived to me. So artificial. And more often than not, nothing materially changed as a result of them. I have to admit, for a long time I was a skeptic.

But in recent years, I’ve come to see real value in the team offsite meeting. If … and that’s a big IF … you do them the right way.

The question for today: What are the do’s and don’ts for team offsite meetings?

We’ve all been to team building and team offsite meetings that are truly excruciating. That’s why so many of us – me included – hold so much skepticism towards them. We want them to be everything they promise to be, but we’ve been let down so many times. I get it. My hope for today is that I can share with you my do’s and don’ts for hosting a team offsite so you can regain some of that hope and optimism you had walking into your first offsite.

Here are my favorite Do’s and Don’ts for hosting a team offsite:


1.  Build something as a team

Too many offsite meetings are overly focused on business review and plan sharing. I prefer to use them as an opportunity for the team to build or fix something that has tangible value. Take a tough problem you’re dealing with and spend two hours as a team fixing it. Build an integrated program from start to finish. Do something as a team that has demonstrable value. Something, that if all else fails, you can point to after the offsite as a real win. In my experience, bringing the team together to actually build or fix something sets a great tone for the rest of the year and shows the value of working as a team.

2. Do something philanthropic

This is a more recent one for me, but I like it. Having the team step outside of work for moment to help other people can be very positive for morale. It’s also a great way to gain a little perspective on the issues you’ll tackle together in the rest of the meeting. In my experience, kicking off a meeting with a few hours working with a local charity gets the team in a healthy mindset to take on the business issues that will follow.

3.  Move data review to pre-reading

Many team offsite meetings fail because they overwhelm the participants with data and dense content. The impact is the team members spend so much energy trying to digest information, they are unable to have meaningful dialogue around it. So nothing actually happens. Instead of spending your time collaborating on solutions, you end up focusing your time understanding and assimilating data. My advice is to publish all content at least a few days ahead of time so the team can come prepared to discuss and debate instead of digest.

4.  Establish one core theme

It’s important to know what you’re trying to accomplish before you plan your offsite meeting. That sounds obvious but I’m not sure it’s done effectively in practice. What is the state of your team? What is your biggest issue? If you could only fix one thing, what would it be? For a team I managed recently, our biggest problem was working across functional groups. Each group was solid but projects that spanned multiple groups we not strong. So we designed the entire offsite meeting with the goal of addressing that one issue … and it helped. If you try to take on too many different things or approach the meeting with a generic purpose, you run the risk of accomplishing nothing of substance. My advice is to pick one theme for the meeting aligned with whatever they biggest challenge is you face.

5. Address real problems

There is a tendency in team offsite meetings to gloss over things. We create the illusion of momentum rather than actually making progress. We present a bunch of content, we do some team building exercises, we park a few touchy subjects, and we pat ourselves on the back. But we never actually resolve anything of substance. My advice is to use this precious time with your entire team to make real progress on one or two issues that really matter.

6. Reaffirm the team’s purpose

If your team is anything like mine, it’s always changing. You have new people joining, roles shift, and priorities change. It’s important, in my opinion, to start the offsite meeting by reminding everyone why they are all here in the first place. What is the company trying to do? What are our goals for this year? What kind of team are we trying to build? What are our values? Why are we here? Starting the meeting by reminding everyone of the fundamental purpose of the team and the goals of the company, you get everyone in the optimal mindset to make progress.

7.  Follow up with regular cadence

How many offsite meetings have you been to where everyone leaves full of optimism and energy only to never speak of it again? Offsite ideas have a tendency to die on the vine. We never actually harvest the ideas and adjustments we seem so committed to in the moment. It’s kind of sad actually. But it happens over and over again. It’s no wonder there are so many offsite cynics amongst us. But … it doesn’t have to be this way. My advice is to pull a few key initiatives from the meeting discussions and turn them into projects you actively manage until the next offsite. And then, early in the next offsite agenda, report on the outcome of the projects. Keep the number of initiatives to a minimum – just the big ones.

8. Bring in customers or outside speakers

Teams have a tendency to get insulated from the rest of the company and from the market. We get locked into a way of thinking and we can lose perspective if we’re not careful. I like to use the offsite meeting as an opportunity to disrupt the common perspective. Inviting customers or leaders of other teams to speak at your team offsite is a really good way to get your team thinking differently. For Marketing, Sales, Product and Support teams, I love having customers come in to tell their stories firsthand. For HR, Finance, IT and other operational teams, it’s nice to have other leaders come into speak about their processes and challenges.


1.  Make it a one-way broadcast

One way to guarantee low engagement and muted results for you next offsite meeting is to build an agenda comprised primarily of one-way communication. This might sound obvious to you but most offsites I’ve been to consist of a series of presentations by functional leaders followed by almost no questions from audience members who are mostly focused on trying to stay awake. Don’t make this mistake. Build collaboration into your sessions. Build something together. Brainstorm solutions to problems. Debate and discuss.

2.  Fixate on business review and plans

At some point you need to review the team’s performance and share plans for the coming months. Just don’t make it your entire agenda. Don’t even make it a quarter of your agenda. It’s a rare thing to have your entire team together. You can do anything you want. Why make it about listening to business reviews and plan? Sure you need people to be informed and aware, but do you really need to use these precious hours for that purpose? Why not do a one-hour web meeting a week in advance to present the plans and then use the offsite to make progress on them? Why not send the plans out in advance as pre-reading and then use the time together to brainstorm ideas?

3. Pack the agenda too tightly

The worst offsite meetings feel rushed. The pace is too fast so nothing of substance gets accomplished. You feel pressured by time so you race through the tough issues or you park them for follow-up discussion. That’s exactly the opposite of what you should be doing when you have your entire team sitting in a room outside of the office. Now is the time to debate and discuss without another meeting looming in 10 minutes. My recommendation is to take whatever agenda you think has the optimal pace and reduce it by another 20 percent. I’ve never been to an offsite that finished early. We always over estimate what we can accomplish in a day or two. Take your time, take on less, make real progress on a smaller set of topics.

4. Structure around functions only

Many offsite agendas are structured around functional reporting. In the Marketing team example, you typically build an agenda where each functional leader presents a report of progress and a plan for the upcoming period. The web team presents web stuff. The creative team presents creative stuff. The product team presents product stuff. You get the picture. The problem with this is teams don’t actually operate like this in practice. In actual fact, all these functions work together to achieve outcomes for the company. If you don’t want your teams operating in silos (something every manager gripes about) then don’t structure your agenda in silos. My recommendation is to build your offsite agenda around cross functional challenges and initiatives. Do a working session on how all the teams can contribute to helping the company win in a new market. Do a brainstorming session on how we can optimize our multi-team process for launching new products. If you have your entire team together already, you might as well use the time to focus on issues that are relevant to the entire team.

5.  Take all hard issues offline

Don’t park all the hard stuff. Don’t take all the contentious issues “offline”. The offsite meeting is the perfect moment to get into it. As managers, I think we’re too quick to take things offline. I’ve tried to raise my tolerance for longer discussions in recent years and the results are good. Let people debate for a while. Let team members reach an impasse and then help them move past it. The only time I recommend parking topics for later is if they just aren’t relevant to the group. In that case it makes sense. But if you find yourself getting antsy because the team is dwelling on a tough issue for a while, help them work it out instead of sending it to the parking lot.

6. Force fun

Nobody likes forced fun. It’s great to have team building activities and fun things to do during the offsite meeting but too many managers neglect to put themselves in the shoes of the attendees. Just because something is a barrel of laughs for you doesn’t mean it is for everyone else. My guiding principle for fun offsite activities is to choose simple things that create opportunities for people to spend quality time together. You want people interacting with each other and with team members they might not get to spend much time with on a regular basis. Activities that don’t allow people to actually talk e.g. sporting events or shows aren’t the best for this.

I hope you enjoyed my list of offsite Do’s and Don’ts. I’d love to hear some of the things that have worked (and not worked)

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