Considering an Offsite Meeting? Five Key Questions for Managers

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All right, so occasionally I am a little selfish in terms of how I pick articles. I'm getting ready to plan an offsite for a regional committee that I'm responsible for creating. And this article really, really spoke to me. Planning an offsite for your leadership team? Ask these five questions. It's by Marissa Fernandez and Franz von Leif. It's from July 2025. Harvard Business Review.

So as a leader, if you feel like something is off with your team and you need to recapture morale, you need to recapture collaboration, momentum, whatever it might be, or maybe you're like me, you're planning a new committee and you want to have a big impact on them, or maybe your team is doing fine and you just want to push the envelope with them, have a greater capacity to produce great results. No matter what it is, an off-site can be a very good strategy.

But according to this article, only when they're designed with clear intent. Many leaders assume that's starting with the end in mind. So just setting goals, making sure that you accomplish your goals over the offsite. They think that that's really all you need to do to ensure a successful meeting.

But in the experience of these authors who has worked with, they've worked with corporate clients all over the world, designing impactful offsites, setting the goals of the meeting is just the beginning. It's the obvious first step, but the article also then comes up with five additional and often overlooked. Outcome-oriented questions that will help you design an offsite that will last years potentially after the meeting is over.

And that's what you really want, right? So the first question is how do you want your team to feel? How do you want your team to feel? So the article goes into one client, a utilities company, who wanted their team to feel cozy, comfortable, and connected. And so that led to a change in venue.

So not having the meeting at a sterile hotel conference room, they shifted to a like an Airbnb rental home, which gave them a kind of a cozy family-like connection and allow them to achieve that desired emotional outcome. So that's just an example of how asking the question, how do you want your team to feel, can lead to all kinds of, maybe even a change in venue. It can lead to a change in how you approach the breakouts, how you approach the the questions, how you approach the follow-up.

So, it's really, really important to be really intentional about the emotions that you want to create and by crafting the right type of experience. Okay, number two, what's getting in the way of your team's success? So, the article talks about a large retailer leadership team. They were consistently struggling to make decisions efficiently. And so the leader, recognizing this, brought three really important decisions to the meeting.

They brought several different types of decision-making tools, and they actually implemented those tools on the very decisions that they were needing to make, and then at the end came to a consensus on what decision tools worked the best. And they left then that meeting immediately clarifying their decision-making process going forward. I love that. So what's getting in the way of your team's success?

Now, obviously, if you don't have a team yet, like me, this is an interesting question, but it's not necessarily relevant to my situation particularly. Okay, the third one is, what shift in behaviors will set your team on a new trajectory? So, consider in what ways your hope, that you hope. Things will be different when examining the before and after of the offsite. So a great offsite is a memorable milestone, right? It sets kind of a marker in your team's history, your team's story.

And you want it to kind of be a place where you look back and say, you know what, that's the meeting where we all kind of got on the same page. Or that's the meeting where we, you know, made our fateful decision to go with this process, and it really has changed everything. So that different trajectory can only be created with very different behaviors that you want to see after the session. So be very, very specific in terms of what behaviors you want to see after the session.

Okay, the fourth thing, what do you want your team to stop doing? So offsites often generate new actions for the team's to-do list, right? Sometimes they can fill up to-do list. Less commonly do leaders think about what can be subtracted. So in order to create capacity to operate more efficiently and be able to implement new ideas, sometimes we have to create room for it. So we have to subtract some things that we need to create room for.

And so the article, again, talks about one of their clients. It was a financial services organization. And they realized that they were allocating internal resources in a very problematic way. It wasn't really in line with their strategic focus of their business. And so they designed a very specific off-site session where they identified ways of working, and they identified the friction that could be eliminated to free up capacity, and they had this huge brainstorming session.

And then the team selected three items as a team, and each selected one of those items that they would immediately offload, just immediately get rid of. The feeling of release was palpable, according to the article. And the exercise turned out to be kind of a fire starter for the whole organization, inspiring more offloading and creating more and more capacity for more higher value work.

Okay. And then the last one, number five, how are you going to make it stick? We, as trainers and leadership development specialists, we want the things that we do, we want them to last, right? We want them to live on with the client. And I want this meeting coming up to live on in our team members. So an off-site offers people a pause in the regular routines.

It offers a pause in their routines to connect, then their routines to reflect, before they then default back into this busy, crazy world that we all live in. But lasting adjustments and changes are possible and have the greatest significance only if we can make it stick. And so making it stick has to be considered a part of the planning, not as an afterthought and a hope, right?

So the article recommends that you allocate time at the end of the offsite to really align with the team on a handful of commitments. So by setting expectations that all participants will be held accountable, tracking the team progress versus commitments on a quarterly basis, intervening when progress isn't demonstrated, and then rewarding continuing efforts when they are demonstrated, those are all great best practices to make sure that you have solidified before you leave that off-site.

Off-sites aren't just a day away from the office. They're an opportunity to reset your team's path.

By focusing on these five questions, you'll transform a routine gathering into a catalysts for meaningful change. Start with the end in mind, ask the right questions, but then design and deliver an offsite that creates connection, clarity, and momentum so that your team walks away primed to thrive. And until next time we meet in the Manager Lab, do good work. Music.