Published 8 May 2026

Why great content isn’t enough to make an offsite work.

Author: Lisa James Founder and CEO, The Wentworth Collective

Why do so many leadership offsites fail to create lasting change? Because organisations focus on what people will hear, rather than what they need to think, connect and act.

The venue was impressive, the speakers were strong, the strategy clear, and the feedback positive.

And yet, six weeks later, very little has changed.

Decisions are being revisited. The alignment people felt in the room has weakened and everyone has returned to familiar ways of working.

Sound familiar?

People leave believing the offsite was a success. But once they’re back in the business, the momentum fades and familiar patterns quietly return.

So, if the content was good, why didn’t it stick?

After thirty years of designing leadership events for global businesses, I’ve come to believe the answer is surprisingly simple.

We spend months perfecting what people will hear, but almost no time creating the conditions to ensure they actually hear it.


We start in the wrong place

Most planning conversations begin in the wrong place:

  • The message.
  • The agenda.
  • Who should speak.

They all sound like sensible considerations when planning an event – and they are.

They’re just not the first ones you should be thinking about. Before asking, “What do we need to cover?”, the question I always ask is:

“What do our people need if this is going to succeed?”

That reframe changes every decision that follows. Over the years, I’ve learned that the experience surrounding the programme – before and after – determines whether people are ready to listen, think, challenge one another and act on what they hear.


People don’t arrive as blank slates

People rarely walk into a leadership offsite calm, focused and ready to engage.

They arrive carrying:

  • The stress of the journey.
  • The work they left unfinished.
  • Uncertainty about what will be asked of them.
  • Existing tensions within the team.
  • Concerns about changes taking place across the organisation.

Some will be excited, some will be sceptical, some may already be braced for another long day of presentations.

Those things come into the room with them. They shape how willing people are to listen, how honestly they speak, whether they trust the people around them and whether they commit to a decision once they leave the room.

I’ve seen organisations deliver excellent content that simply couldn’t land because people weren’t ready to receive it.


Design around what people need

So what’s the solution?

Meet people where they are. Design for what they need in order for the message to land.

That doesn’t mean adding wellbeing sessions or forcing senior leaders through awkward team-building exercises. It means understanding what people need to contribute at their best, then creating those conditions deliberately.

Help people arrive well

The event begins long before the opening presentation: It begins with the invitation, travel information, clarity of the communication, the welcome people receive when they arrive.

If someone walks through the door flustered, hungry or uncertain about where they need to be, they are not ready to engage with a strategy.

So remove the friction.

Make the welcome warm and visible, tell people what to expect, give them time to settle, get food and water in front of them. Handle luggage, room keys and dietary requirements without turning them into another job for the guest.

These details can look operational on a planning document but to the person attending, they communicate something much more important.

You were expected. We’ve thought about what you need. You’re in good hands.

That’s often the moment people begin to relax. And when people relax, they’re far more open to what’s about to happen next.

Create space to think

Leadership teams already spend most of their working lives moving from one meeting to the next. An offsite shouldn’t simply recreate that rhythm somewhere else.

The instinct is always to fill the agenda, but a day packed like a spreadsheet produces spreadsheet-level thinking. People need time to process what they’ve heard, continue conversations over coffee or while walking between sessions. To sit quietly before making an important decision.

None of this is wasted time; In my experience, it’s often where the real work happens.

You don’t create alignment by filling every available minute, you create it by giving people enough space to reach it.

Build connection before alignment

People need an opportunity to connect before they’re asked to align and trust one another to make important decisions – and trust rarely appears because someone puts the word collaboration on a slide.

So how do we build trust and connection? Through shared experiences that help them see one another differently.

At one global partner conference, we invited a group of senior lawyers to create street art together. At another leadership event, we asked people to bring photos of their favourite summer memory to share with others.

These activities weren’t about artwork, or about summer memories. They were about changing the way people related to one another before asking them to tackle difficult strategic conversations.

When people create something together, hierarchy softens, different conversations become possible. That’s why connection isn’t something to squeeze in at the end of the agenda, it’s part of preparing people for the work that really matters.

Pay attention to the human details

Food matters. Lighting matters. Temperature, acoustics and room layout matter. (So do the toilets, I’ve turned down beautiful venues because this most basic human need wasn’t good enough for the experience we wanted to create.)

Because if someone is hungry, uncomfortable or struggling to hear, they are never fully present.

Quiet spaces matter too. People need somewhere to decompress, have smaller conversations and step away from the group without it feeling awkward. Some of the most valuable conversations I’ve witnessed have happened away from the formal agenda, in gardens, quiet corners and comfortable spaces where people had room to talk honestly and informally.

These details are easy to dismiss as logistics but I’ve always seen them as part of the experience itself.

Small details change how people feel. And how people feel changes how they participate.


The experience is part of the strategy

This is why I don’t separate event design from event logistics.

Arrival, travel, food, room layout, shared experiences, quiet spaces; They’re not operational details to think about once the important decisions have been made. They are the important decisions.

If the purpose of an offsite is to build trust, make decisions, create alignment or change behaviour, the environment has to support those outcomes.

You can’t ask for open thinking in a room that feels rigid, for honest conversation without creating trust or for people to absorb a new strategy while giving them no time to process it.

The agenda may communicate the strategy. The experience determines how people receive it.


Measure what happens next

Positive feedback at the end of an offsite is always encouraging, but it isn’t the same as lasting impact. The more important questions come later.

  • Did the decisions stick?
  • Did people take ownership?
  • Did relationships improve?
  • Are teams having more honest conversations?
  • Did the strategy turn into action?

Or did everyone simply return to work and carry on as before?

The best offsites reduce the need to have the same conversations over and over again. They create clarity that survives the journey home. They help people work together differently long after the event has finished.


Make the conditions count

Great leadership offsites aren’t defined by the quality of their content alone, they’re defined by the conditions they create for people to listen, connect and contribute.

So before you perfect the agenda, pause for a moment, think about the people who will be sitting in the room.

  • What will they be carrying when they arrive?
  • What might prevent them from engaging?
  • What will help them feel ready to contribute?

Start there.

Because the programme communicates the strategy. The experience determines whether it sticks.

And that’s the difference between an offsite people remember… and one that genuinely changes the way they work together.



Further reading

  1. Rewiring the Organizational Network: Corporate Offsites and Network Tie Formation
  2. Make the Most of Your Offsites — Harvard Business Review
  3. Virtual Communication Curbs Creative Idea Generation — Nature
  4. Psychological Safety Comes of Age — Annual Review of Organizational Psychology and Organizational Behavior
  5. If We’re All So Busy, Why Isn’t Anything Getting Done? — McKinsey
  6. The Increasing Importance of a Best Friend at Work — Gallup
  7. How to Make In-Person Time Count — Microsoft WorkLab
  8. Effect of Lighting Illuminance and Colour Temperature on Mental Workload — Scientific Reports
  9. Workplace Sound Level and Physiological Wellbeing — npj Digital Medicine
  10. Training Design, Work Environment and Transfer of Learning — European Journal of Training and Development

Events need to change.
Events need to change.

I’ve spent 30 years designing transformative events. The events are unique, the science behind them remains the same. I use 7 trusted frameworks to build every event. I've put them into a playbook.