When it comes to leadership offsites, the ideal is often some kind of corporate harmony – picture a luxury countryside retreat, comfortable chairs in a circle, perhaps sunshine filtering through the windows as team members nod appreciatively at one another's carefully considered insights. Reality, however, rarely gets the memo. Leadership teams can be messy, a little bruised around the edges, and if you’re not careful, your tranquil two-day retreat can start to resemble a hostage situation.

For one leadership team, the idea of two days spent in close quarters had triggered some early warning signs. There were a few fractured relationships in the mix, with the odd “Do we have to?” muttered under the breath. Some were keen to talk business and fix things; others had a gnawing reluctance about the whole experience – they simply didn’t want to spend all that time together. So, what do you do? How do you turn two days of eye-rolling and simmering tensions into something resembling a productive discussion?

The atmosphere: a delicate balance

Let’s start with the basics. You’ve got a mix of strong personalities, all with their own set of opinions, frustrations, and often a stubborn refusal to back down. Setting the tone for this kind of offsite is crucial. If you get it wrong, you risk turning debates into personal attacks or, worse still, into silence. You want a space where people feel free to speak openly but where things don’t escalate. It’s a tightrope walk between encouraging robust debate and keeping things from boiling over.

This is where psychological safety comes in. You’ve probably heard the term thrown around – it’s become a bit of a buzzword in team dynamics. But what does it actually mean? In its simplest form, psychological safety is about creating an environment where people feel safe to take risks, speak up, and be themselves without fear of humiliation or punishment. For your leadership offsite, this could mean the difference between people sharing what they really think and simply toeing the company line.

Avoiding the elephant trap: groupthink

At the other end of the spectrum from toxic conflict, you’ve got groupthink – the silent killer of innovation. It’s what happens when people feel pressured to conform, often without even realising it. They might nod along, avoid rocking the boat, and in doing so, they prevent the hard conversations that need to happen.

The offsite is your opportunity to sidestep this. The goal is to encourage genuine dialogue, not a series of polite agreements. You want people to disagree – but constructively. Encouraging dissenting opinions can break through the suffocating effects of groupthink. But it needs to be done with care. Set the ground rules early: differing views are welcome, but it’s about the ideas, not the person behind them. This might sound basic, but it’s surprising how quickly things can get personal in a high-stakes environment.

It’s not therapy, but...

While the offsite is ultimately about improving the business, you can’t ignore the human dynamics at play. You’re not here to play therapist, but let’s face it: any successful team is built on trust. If your leadership team can’t get through a two-day offsite without snapping at each other, you’re unlikely to make much headway with those visionary strategic goals.

A few practical steps can help:

1. Ice-breakers, but not the cringey kind. Start the offsite with a simple check-in. How are we feeling? What do we want to accomplish today? You’re not trying to make everyone best mates – yet – for now, you’re just creating a bit of shared laughter or at least mutual tolerance.
2. Create opportunities for one-on-one interactions. Pair people up in different combinations to discuss specific topics. Sometimes people feel more comfortable airing their thoughts in smaller groups.
3. Use an outside facilitator. This neutral third party can help keep the discussion flowing, steer it away from sensitive areas, and keep everyone on track. A good facilitator knows when to let things breathe and when to step in to redirect the conversation.
4. Agree on confidentiality. If people feel like what they say in the room could be held against them later, they’re unlikely to speak freely. Get a group agreement on confidentiality early on.

The balance of discomfort

There’s an art to managing the offsite experience. Too much cosiness and people will skirt around the real issues; too much confrontation and you’ll end up with a leadership implosion. It’s about finding that optimal level of discomfort. You want your team to lean into the discomfort – to have the hard conversations that get results – but not feel under attack.

A good analogy here is an elastic band - you want the right amount of tension, not too much so it snaps, and not too little so it sags.

It’s helpful to remember that discomfort isn’t a bad thing. In fact, it’s often where the most productive conversations happen. But discomfort needs to be handled with care. This is where your facilitation skills (or your facilitator’s) come into play. When someone’s pushing back, is it in the service of the team’s goals, or are they simply venting frustrations that have nothing to do with the topic at hand? A good facilitator can sense when to encourage a bit more pushback and when to step in and defuse.

Building momentum after the offsite

So, you’ve managed to get through the two days without any serious injuries, emotional or otherwise. But what happens next? Too often, leadership offsites are seen as one-off events, with any goodwill or momentum quickly evaporating once people return to their day jobs.

The offsite isn’t a standalone fix. It should be part of a broader process. That means regular check-ins, follow-up meetings, and continuous improvement. If you don’t follow through, all the hard work – the tense but necessary conversations, the moments of breakthrough – will have been for nothing.

It’s worth noting that offsites are as much about relationship-building as they are about strategy-setting. People need time and space to get comfortable with each other, especially if there’s been a bit of friction in the past. So, don’t expect everything to be perfect by the end. But if you’ve created an environment where people feel safe to speak up, challenged groupthink, and started to break down barriers, you’re on the right track.

Closing thoughts

An offsite can be many things – a war zone, a therapy session, or (if you’re lucky) a place where great ideas flourish and relationships are strengthened. If you can create the right atmosphere – one of psychological safety and constructive dissent – then your team has a chance of coming out stronger on the other side.

At the end of the day, it’s about striking a balance between pushing your team out of their comfort zone and making sure they’re not pushed so far they break. Not an easy task, but then again, if it was easy, it wouldn’t be called leadership.