Dana Campbell, PCC
CEO | Leadership Coach | Advisor | Speaker | Change Leader | Stress Resiliency Expert
I’ve facilitated more than 100 executive team offsites over the years, and one of the biggest mistakes I see happens before the team ever gets in the room.
They start with the agenda.
Or, just as often, the CEO has already decided what the agenda should be and hands it to someone else to build out—sometimes a member of the team, sometimes someone who won't even be in the room.
What do we need to cover? Who needs time? What didn't we get to last year? What do we need to make sure we talk about while everyone is together?
And pretty quickly, two days are full.
But very few people have stopped to ask:
What actually needs to be different when this team leaves the room?
Maybe there are three decisions the team has been circling for months. Maybe everyone says they agree on the strategy, but they're making very different choices about where to put people and money. Maybe two leaders have learned to work around each other rather than with each other. Maybe the CEO is still the person who has to resolve every meaningful tradeoff.
Those are very different problems. And they should lead to very different offsites.
TL;DR
Executive offsites take a lot of time, money and leadership capacity. Yet we often set the bar surprisingly low for what they should accomplish.
A great offsite should strengthen the relationships around the table, move consequential business work forward, and make the team better at leading the business together.
Before you build the agenda, get clear on what needs to change.
Two days is a significant investment
PwC recently found that 57% of executives say slow decision-making is causing their companies to miss business opportunities.
Think about that in the context of an executive offsite.
You have the CEO and most senior leaders in the company together, without the usual interruptions, for a day or two.
When else do you have that?
The cost of the offsite itself isn't really the issue. It's the opportunity cost of having this particular group of people together and not using the time to tackle the things that only they can tackle.
Yet I've seen teams use hours of that time on presentations that could have been read in advance, functional updates that could have happened in a regular leadership meeting, or conversations that stop just as they start to get somewhere interesting because it's time to move to the next item on the agenda.
Everyone leaves having covered a lot.
I'm not sure that's the same as accomplishing a lot.
Connection matters. It's just not enough.
I want to be careful here, because I'm not in the camp that believes every minute of an executive offsite needs to be spent solving a business problem.
Relationships matter.
In fact, they're one of the reasons I believe getting a leadership team together in person is so valuable.
When leaders know one another beyond their roles, there's often less friction in the work. It's easier to pick up the phone instead of escalating something. It's easier to challenge someone when you trust their intent. It's easier to have a hard conversation and know the relationship can withstand it.
So have dinner. Take the walk. Make room for conversations that have nothing to do with next year's operating plan.
Just don't confuse a more connected team with a more effective one.
Connection should increase the team's capacity to do hard things together.
Can they have the disagreement they've been avoiding?
Can they make a decision when there isn't an obvious right answer?
Can they make a tradeoff that's right for the company even when it's painful for their own function?
Can they tell each other what isn't working?
Can the CEO step back without everything grinding to a halt?
That's where relationships start to have real business value.
The agenda can give you a false sense of accomplishment
I've watched this happen more times than I can count.
A team gets into a conversation that clearly matters. There's disagreement. Someone says something that changes the way the group is looking at the problem. Maybe an assumption everyone thought they shared turns out not to be shared at all.
And then someone looks at the clock.
We have to move on.
There's a lot left on the agenda.
So the team tables the conversation, moves to the next topic and ends the offsite having successfully covered everything it planned to cover.
Except perhaps the thing it most needed to talk about.
This is where I think we have the wrong definition of a successful offsite.
Getting through the agenda isn't the goal.
Neither is leaving with 14 action items, a photo of a whiteboard and everyone saying it was a productive two days.
Something should move.
A decision gets made that has been stuck.
A strategic choice becomes clearer.
Two leaders finally address the issue between them instead of asking the rest of the organization to absorb it.
The team realizes it has been solving every difficult decision through the CEO and starts building the muscle to do otherwise.
Or maybe people simply understand one another differently, and a relationship that had become a source of friction starts working again.
These are very different outcomes.
But each one changes what happens when everyone goes back to work.
Start before the agenda
When we work with an executive team, we don't start by building the agenda.
We start by understanding what is happening in the business and on the team.
I want to hear from the CEO. But I also want to hear from the people who will actually be sitting around the table. Where are they getting stuck? What aren't they talking about? What one issue keeps resurfacing without resolution? Where is the business asking something of this team that they aren't yet delivering? What would make these two days genuinely valuable?
That context changes what happens in the room.
Sometimes it means spending far less time on something the CEO assumed needed half a day. Sometimes it surfaces an issue that wasn't on the original agenda at all. And sometimes it tells us that the team doesn't need another conversation about a problem—they need to finally make a decision.
The agenda comes out of that work. It isn't where the work starts.
And even then, we don't think the agenda is sacred. When we facilitate, there is always a Plan B—and usually a Plan C. If the team gets into the conversation it actually needs to have, our job isn't to rush them through it because we're 20 minutes behind.
It's to recognize when we've hit something that matters and help the team do something useful with it.
That, to me, is what it means to raise the bar.
That's the bar
An executive offsite is one of the rare opportunities a leadership team has to step out of running the business long enough to look at how they're leading it.
What does the business need from us now?
Where are we getting in our own way?
What are we avoiding?
What has changed about the company that requires something different from this team?
And where do we need to be better together for the business to go where we're asking it to go?
Those aren't agenda questions.
They're leadership questions.
And they matter because the real test of an offsite isn't how the team feels at 4 p.m. on day two.
It's what you can see three months later.
A decision that finally got made.
A problem that got unstuck.
A relationship that can withstand more candor.
A CEO who is no longer the integration point for every hard call.
A leadership team that is better equipped for what the business is asking of it next.
That's a much higher bar.
Given the people you have in the room, it should be.
Next in this series: Why I think most leadership teams should plan less for their offsites—and leave more room to go deep.
Want to raise the bar for your next offsite?
If you're bringing your leadership team together and want an outside perspective on how to make the time count, reach out. We spend a lot of time helping executive teams figure out what actually needs to happen in the room—and facilitating the conversations that move the team and the business forward.
About Optimize Corps
Optimize Corps works with CEOs and executive teams to build the leadership capacity their businesses need to grow, change, and navigate increasing complexity.
We help strong functional leaders operate as enterprise leaders—leaders who can make hard tradeoffs, solve problems together when the answer isn't obvious, and take shared ownership for the business.
The goal is an executive team capable of leading the enterprise together: a team that creates more value together than its members could independently, and a CEO who doesn't have to sit at the center of every consequential decision.