Beyond the offsite: 5 questions for executive team traction

Executive teams are under huge pressure. They have to deliver results, handle complexity and make decisions that shape their organisation’s future. But how often do they step out of the day to day and look hard at how well they work as a team?

A recent Harvard Business Review article by Marissa Fernandez and Frans van Loef, Planning an Offsite for Your Leadership Team? Ask These 5 Questions, makes a useful point. A well-designed offsite can reset a team’s direction, which is worth far more than a day reconnecting away from the office.

We see this at Five all the time. The best offsites are judged by what the team was willing to face, commit to and do differently. How engaging the activities were, or how energised people felt walking out, matters much less.

Here are 5 questions we bring to executive teams before an offsite.

What does the business need from this team next?

Too many offsites start with a list of topics instead of an honest look at what the team most needs to achieve.

So before an offsite, we spend time understanding the team’s context, strategic priorities and dynamics. The useful question is what needs to shift in how this team works to deliver what the business needs next. The list of things to discuss comes after that.

What’s really getting in the way?

In our work with executive teams across New Zealand and Australia, the presenting challenge is rarely the whole story. It might look like strategy alignment, collaboration or decision-making.

Underneath, there are often competing functional priorities, unspoken tension, unclear accountability, or leadership habits that slow progress without anyone intending it. An offsite that only treats the presenting challenge won’t move much.

Which conversations are we avoiding?

High-performing executive teams have hard conversations. They build the trust, psychological safety and shared accountability to have them well.

We make space for the questions leaders rarely have the time, or sometimes the confidence, to raise in their regular meetings. Questions like these.

• Where are we acting as functional leaders rather than enterprise leaders?
• What aren’t we saying to each other that needs to be said?
• How are our own leadership behaviours helping, or holding back, how well we work together?

These conversations need careful design, skilled facilitation and leaders who are willing to test their own assumptions. A clever activity won’t get you there on its own.

Sometimes the most valuable moment of an offsite is the uncomfortable silence before someone says what everyone else has been thinking.

What will we do differently from Monday?

We’ve all been to offsites where the energy is high, the conversations are rich and everyone leaves with good intentions. Then Monday arrives. Urgent work takes over, old patterns return and the momentum fades.

At Five, we deliberately link insight to practical changes in how leaders behave and work together. That might mean helping a team redefine its collective role, agree how it will challenge itself well, strengthen accountability across functions, or change how it makes decisions and sets priorities.

The aim is a small number of real commitments that change how the team works together, rather than another long action list.

How will we make it stick?

A good offsite builds alignment on the day. A great one lays the foundations for lasting team effectiveness.

That means coming back to commitments, making room for honest feedback, and holding each other to the behaviours that help the team perform.

It also means accepting that executive team development is ongoing work. Like any high-performing team, it takes deliberate attention, practice and a willingness to keep adapting.

Start with where you want to be in 6 months

We measure an offsite by whether the team leaves better equipped, and more committed, to lead together. Feeling inspired is a bonus.

So before you plan your next offsite, start with this question.

What would you want to see this team doing differently in 6 months’ time that would make the biggest difference to your organisation’s performance?

Start there.

Inspired by Marissa Fernandez and Frans van Loef, “Planning an Offsite for Your Leadership Team? Ask These 5 Questions”, Harvard Business Review, 17 July 2025.