Published 10 October 2026

Connection. The infrastructure we underinvest in. 

Author: Lisa James Founder and CEO, The Wentworth Collective

When people genuinely connect, work changes. Which makes me wonder: Why do we invest so little in connection itself?

I’ve spent 30 years creating corporate events and I’ve seen this happen again and again. 

Businesses invest heavily in technology. Systems. Offices. Processes. People. 
But what about the relationships between those people? 

When relationships are weak, the effects show up in the work. People hold back unfinished ideas, avoid difficult conversations and stay within their own teams. Information moves more slowly. Silos strengthen. Momentum becomes harder to build. 

I was once working with the brand new CEO of a global firm and one of the first things he did, may surprise you. 
He took his leadership team… to Center Parcs. 

There were still serious conversations to be had, decisions to make and a business to move forward. And all of that happened. But between the presentations, meetings and more formal agenda items, people opened up, listened differently and started to understand each other.  

They connected. 

Connection is not a soft extra around the work. It’s part of the infrastructure that makes the work possible. 


What if we had a connection stack? 

We talk all the time about the technology stack a business needs to operate. I think we need to start thinking about our connection stack too. 

The places, experiences and opportunities where people get to know each other beyond a job title, slack avatar or a square on a video call. Because we have never had more ways to communicate and yet, I’m not convinced we have ever found it harder to really connect. 

I can message someone instantly, jump onto a virtual meeting or ask AI a question and have an answer before I’ve even thought about who in my team might know it. All of that is incredibly useful. 

But communication and connection are not the same thing. Connection is feeling seen. Knowing who I can turn to, understanding how somebody thinks, having enough trust to disagree and feeling that I’m part of something rather than simply working alongside it. 


Connection doesn’t happen by accident anymore 

Hybrid working has given us enormous flexibility. But it has also removed many of those tiny, apparently insignificant moments that used to happen naturally:

Conversation while making coffee.
Five minutes after a meeting. 
Questions shouted across a desk. 
Chats over lunch.

None of those moments looks particularly productive on a spreadsheet. But those moments were building relationships. Now, we can ask AI instead of asking each other – a whopping 47% of us would choose AI over a colleague because it is always available. 

I understand why. It’s quick, convenient and efficient. 

But every time I choose technology instead of another person, I potentially remove another small opportunity to connect. And younger employees appear to be feeling this particularly sharply. Loneliness among remote-capable Gen Z employees is higher than among millennials, Gen X and baby boomers. 

Your established employees are working remotely with relationships they originally built in person. They already know who to call, whose judgement to trust and how to read the hesitation behind somebody’s words. But newer employees are being asked to build those relationships through a screen.

That is a very different starting point. 

The more efficiently technology allows us to work apart, the more intentionally I believe we need to create opportunities to come together. 


Being together changes the conversation 

There is something different about sharing physical space. 

Research looking at creative collaboration found that video calls inhibited the generation of creative ideas compared with working together in person, although they didn’t appear to affect the quality of decisions made afterwards. That distinction interests me because I don’t believe every meeting needs to be in person. Far from it. 

Routine updates, straightforward decisions and information sharing can often happen perfectly well online. Physical time becomes particularly valuable when the work requires trust, creativity, alignment, a difficult conversation or stronger relationships. 

I wouldn’t ask people to travel across the country to sit through something that could have been a video call. If people have travelled to be together, I want to use that time differently. 

I want to create the conversations that don’t happen on Teams, to meet somebody they wouldn’t normally speak to.
I want the environment to change how they think and them to leave knowing each other better than when they arrived. 

That was exactly what happened at the leadership retreat in Center Parcs. The leadership team needed strategic alignment. They needed to trust a new CEO, to believe in where the business was going. We designed for all of that. 

But we also left room for breakfast together, walks through the woods. cups of tea and informal conversations. By the end, they weren’t simply clearer about the strategy. They were better equipped to deliver it together.


So how do I make gatherings count? 

When it comes to gatherings, attendance is not the same as participation. Connection won’t happen by accident – you need to design for it. 

If you’re investing the time and effort in bringing people together, you need to make sure it delivers the intended business goals. So here’s how we do that in our events:

Start with the change, not the event 

My first question is always: What needs to be different because this event happened? 
Not Where should we go? Or even What do we need to communicate? 

What needs to change? 

Once I know that, I can start designing the experience. 

Signal belonging from the beginning 

Connection starts long before somebody takes their seat. I think a lot about how people arrive; How they are welcomed, what they see, who they meet. 

At a recent leadership conference at Oakley Court, something as simple as welcoming people with coffee by the lake set the pace for the entire conference: People relaxed, settled. That meant they were able to fully engage with the experience. At the end of the event, people left saying it was the best leadership retreat they’d had. 

Making people feel like they belong matters. 

Give people a reason to participate 

People sitting passively for hours in a conference room, is not million miles away from sitting on a webinar or video call. 
At my events, I want them to engage. And the shortcut to engagement is doing something together. I’ve had teams create street art in Berlin, build with Lego in Copenhagen, volunteer in nature reserves in London. 

It isn’t about forcing fun. It’s about giving people a shared experience. A feeling that Those experiences are what 

Plan what happens next 

This is the bit I see missed most often. Everyone gets home, the photographs arrive, there’s a lovely internal email, and then Monday happens and we’re back to business as usual.

You need to design for what happens next. I call this The Cascade.

For Vitality, the themes that came out of a leadership retreat became workstreams and workshops in Creativity Labs for years to come.

The event created momentum and the business carried it forward. 

That’s when I know an event has done its job. The measure is not simply who attended or whether they enjoyed it. It’s what changes afterwards. 


Events belong in business strategy 

I’ve never believed an event is “just an event”. 

Every gathering is a strategic opportunity for your business.

When the right people are brought together, at the right moment, in the right conditions relationships change, trust builds, ideas emerge. People find the confidence to say what needs to be said. And businesses move forwards.

Digital tools, AI and hybrid working have brought real benefits. I use them too. But the more sophisticated our technology becomes, the more conscious I think we need to be about the human infrastructure sitting alongside it. 

We already invest in the systems that help people work efficiently. I think it’s time we invested with the same intention in the relationships that help people work honestly, creatively and together. 

So before planning the next leadership retreat, conference or company gathering, I’d ask one question. 

What connection needs to exist afterwards that doesn’t exist today? 

Then I’d design from there. Because the event is only the moment. The connection it creates is what carries the business forward. 



FAQs 

Why are my people communicating constantly but still not collaborating effectively? 

Because communication is not the same as connection. Emails, messages, meetings, and shared documents can move information quickly without building trust or familiarity. When people do not know one another well, they may hold information back, avoid challenge, or work around other teams. Better collaboration requires deliberate opportunities to build relationships, share ideas, and solve problems together. 

How can I improve trust and connection in a hybrid organisation without forcing everyone back into the office? 

Create purposeful opportunities for people to meet, participate, and build relationships across teams. This does not mean bringing everyone into the office full-time or adding more unnecessary meetings. Use in-person time when the work requires trust, creativity, alignment, difficult conversations, or relationship-building. Keep routine updates and straightforward decisions online. 

How do I know whether poor collaboration is a people problem, a leadership problem, or a connection problem? 

Look at how people behave when work becomes difficult. If teams avoid asking for help, protect information, struggle to challenge ideas, or work in silos, weak connection may be part of the problem. Connection is not the only possible cause, but trust and familiarity influence how openly people communicate, make decisions, and work across boundaries. 

Are leadership offsites and company events worth the investment, and how should I measure the return? 

They can be worth the investment when they are designed around a clear business need. An event should help people achieve something that would be difficult through normal day-to-day communication, such as aligning behind a strategy, repairing trust, making a difficult decision, or strengthening collaboration. Measure what changes afterwards, not just attendance or satisfaction.

What kind of event would help my teams align behind a new strategy and take ownership of it? 

Start with the change you need to create. If people need clarity, the event should help them understand the strategy and their role in delivering it. If they need ownership, give them opportunities to question, discuss, apply, and shape what the strategy means in practice. The format should follow the outcome, not the other way around. 


Sources 

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.