The Offsite Conversation Your Team Really Wants to Have (and Needs)
Many of us can relate to a time where we were part of a team offsite where the day starts off with lots of hugs, friendly smiles and an energizing ice breaker, but as the day went on… the real issues never surface or get resolved.
Maybe team members were quiet with the loudest people taking up the airspace, making the energy in the room flat, and when it came time to align on a decision — maybe around priorities or how to address a core issue — the conversation got stuck looping, deflecting, sidestepping. It wasn’t a strategy problem. It was a tension problem.
Most Offsites Play It Safe
If you’ve ever planned a team offsite, you know how easy it is to focus on the logistics: picking the venue, getting speakers, creating the schedule, ordering lunch. You hope the retreat will spark clarity or connection. Maybe even solve that thorny issue the team’s been dancing around.
Here’s the truth: you can’t change what you won’t name.
Behind so many team challenges… such as slow decisions, dropped balls, miscommunication, is unresolved tension. The tension might be about roles, trust, communication, or leadership. It doesn’t always look dramatic. Sometimes it just looks like people shutting down, second-guessing, or avoiding eye contact when a certain topic comes up.
When we ignore it during an offsite, we leave the most valuable opportunity on the table.
The Offsite Moment That Changed Everything
One client we worked with, an HR team at a growing healthcare company, came to us just before their annual retreat. The team leader felt friction and frustration across the team, but wasn’t sure why or what to do about it.
During our prep conversations we uncovered people who were frustrated. There were gaps in trust and communication, dropped handoffs between teams, and growing resentment about perceived double-standards and unspoken expectations. Morale was dipping, even though performance metrics were steady. Everyone was feeling it and talking about it in side-pockets, but the group wasn’t addressing it head-on.
We helped the leaders redesign the offsite around one clear, brave goal: name and address the tension.
That doesn’t mean we jumped straight into confrontation. It means we created a safe space for people to say what hadn’t been said. Using pre-interviews and team assessments, neutral facilitation, and tools like Appreciative Inquiry, and Values Mapping, they surfaced the mess, sat with it, and worked through it.
It wasn’t easy but it changed the trajectory of how they now work together.
Why Naming Tension Is a Leadership Move
Too often, managers approach offsite planning with the goal of alignment and “team cohesion”, but you can’t align on something if you’re afraid to talk about it.
If you want your team to leave the offsite feeling not just heard but unblocked, start by asking:
What conversations have we been avoiding?
Where are people confused or second-guessing each other?
What needs to be said, even if it’s uncomfortable?
Where are there different values, opinions, beliefs and assumptions across the team?
Naming those things doesn’t break a team. It builds one.
How to Name Tensions Respectfully: The Art of Curious Listening
Naming tensions isn't about confrontation or blame; it's about creating space for truth to emerge. The most effective leaders approach these conversations with genuine curiosity and skilled listening, treating different viewpoints as valuable data rather than obstacles to overcome.
Start with Active Listening
Active listening goes beyond hearing words. It involves listening for the emotions, needs, and underlying concerns behind what someone is saying. When tensions exist, people often speak in code, using safe language that hints at deeper issues without fully exposing their vulnerability.
Listen for what's not being said. Pay attention to:
Hesitations and pauses
Repeated phrases or concerns
Body language that doesn't match words
Topics that consistently get deflected
Reflect back what you hear. Use phrases like:
"It sounds like you're feeling..."
"What I'm hearing is..."
"Help me understand what that means to you..."
Ask Questions from Genuine Curiosity
The quality of your questions determines the quality of the conversation. Approach tensions with the mindset of an anthropologist—genuinely curious about different perspectives rather than trying to prove a point.
Questions that open dialogue:
"Can you help me understand your perspective on this?"
"What would need to be true for this to work for you?"
"When you say [X], what does that look like in practice?"
"What concerns you most about this situation?"
Questions that explore underlying needs:
"What's most important to you in how we handle this?"
"What would success look like from your viewpoint?"
"What's at stake for you here?"
Create Space for All Viewpoints
The goal isn't to achieve immediate consensus, but to ensure all perspectives are understood and valued. This requires intentional facilitation to prevent dominant voices from overshadowing others.
Techniques for inclusive dialogue:
Round-robin sharing: Give everyone a chance to speak without interruption
Anonymous input: Use tools like sticky notes or digital polls to surface sensitive topics
Perspective mapping: Visually capture different viewpoints on a whiteboard or shared document
Time boundaries: Set clear time limits to prevent any one person from dominating
Move from Positions to Interests
Often, tensions arise when people argue from fixed positions rather than exploring underlying interests. A skilled facilitator helps the group dig deeper.
Position: "We need to hire more people." Interest: "I'm concerned about quality suffering because we're overwhelmed."
Position: "We can't afford to hire anyone." Interest: "I'm worried about budget constraints and need to see clear ROI."
When you understand the interests behind positions, creative solutions become possible. I love using the Ladder of Inference as a tool to help people walk from their positions to their interests.
Build Bridges Toward Shared Understanding
Once all viewpoints are on the table, guide the group toward finding common ground without forcing premature consensus.
Look for shared values: Even in disagreement, teams often share underlying values like quality, growth, or customer satisfaction.
Identify shared concerns: Teams in conflict often worry about similar outcomes, just from different angles.
Acknowledge valid points: Help team members see merit in perspectives different from their own by highlighting valid concerns and insights.
Frame tensions as creative challenges: Reframe disagreements as opportunities to find innovative solutions that honor multiple viewpoints.
You Can’t Facilitate and Participate at the Same Time
Candidly, if you’re the team’s leader, you are most likely part of the tension. It’s not a bad thing, it just means your dual role limits what people are willing to say and how open you can be in the room.
As the leader, you most likely have a point of view and want to participate in the dialogue and decisions. This makes it almost impossible for you to stay neutral in a facilitator role.
Especially when the stakes are high or the dynamics are sticky, we strongly recommend bringing in a neutral offsite facilitator.
An experienced facilitator does more than manage time or hand out sticky-notes. They:
Create psychological safety for honest conversations
Spot the subtle dynamics you might be too close to see
Ask the questions you’re afraid to put on the table
Help your team engage, reflect, and decide without spiraling
Keep the focus on what matters most: moving forward
At Regroup, we’ve supported teams through offsite facilitation that goes beyond surface-level bonding. We help leaders plan offsites that are thoughtful, strategic, and human especially when there’s tension in the mix.
Offsites Should Be a Turning Point, Not Just a Break
You don’t need a perfect agenda. But you do need the courage to guide your team toward what’s true. Because here’s what we’ve learned: When you name what’s real, you create the possibility of real change.
Planning a Team Offsite?
Download The Manager’s Guide to High-Impact Team Offsites
This free, practical guide walks you through the exact steps to design a purposeful offsite from choosing the right goals to knowing when (and how) to name the tension.
It also includes sample agendas, activity menus, and a prep checklist to help you lead with clarity and confidence.
