An interview about a leadership offsite with Steve Morrissey, CEO & Founder of Perpetual, and Perpetual Partners Nigel Robinson and Duke Maines
why a leadership offsite is worth it
Every leadership team eventually asks the same question: is the leadership offsite worth it?
Steve Morrissey sat down with two of Perpetual’s most experienced Talent Development team facilitators, Nigel Robinson and Duke Maines, to talk about what actually separates a force-multiplying leadership offsite from an expensive week away.
STEVE: Let’s start at the top. When a CEO or leadership team first starts thinking about a retreat, what’s the question they should be asking themselves before anything else?
NIGEL: It’s not “where should we go” — that comes much later. The first question is “what does a better tomorrow look like for this team if we get this time right?” Too many organizations start with a venue and work backwards into a purpose. We start with the outcome. Is this about resetting strategy? Cascading a decision that’s already been made? Rebuilding trust after a hard year? Once you’re honest about that, everything else — the theme, the agenda, the location — starts to design itself.
DUKE: I’d add that leadership teams consistently overestimate how aligned they already are. We see it constantly — a team that looks unified in the boardroom but, when you actually get them in a room for two days, surfaces three or four fundamentally different views of where the business is heading. That gap is exactly why the leadership offsite exists. If your team is already perfectly aligned, you probably don’t need us. Most aren’t.
STEVE: So what actually separates a great leadership offsite from a forgettable one?
DUKE: Design. A retreat isn’t one thing — it’s usually a blend of three types of activity: socialising together, learning together, and creating together. Socialising builds trust and connection. Learning brings a team up to the same level on a topic that matters — AI, market shifts, a new capability. Creating is the hard work of actually solving a problem or setting a direction as a group. The mistake most companies make is picking one of those and calling it a retreat, usually the socialising one, and then wondering why nothing changed when everyone got back to their desks.
NIGEL: The other differentiator is follow-through. The best offsites we run leave a team with clear, owned actions, not a nice memory and a shared Google Doc nobody opens again. We build that expectation into the agenda from day one.
STEVE: Let’s talk about facilitation. Why can’t a leadership team just run this themselves? They know their business better than anyone.
NIGEL: They absolutely do, and that’s precisely the problem. If your CFO is also the person facilitating the session on the company’s biggest strategic risk, they can’t fully participate and referee the discussion at the same time. The moment a senior leader is facilitating, they’ve stopped contributing. An external facilitator’s job is to hold the room — the timing, the dynamics, the difficult conversations — so every executive in that room can actually think, debate and contribute like a peer, including the CEO.
“When a senior leader is facilitating, they’ve stopped contributing. That’s the trade-off most teams don’t realize they’re making until it’s too late.” — Nigel Robinson
DUKE: There’s also a psychological safety piece. Teams say things to a neutral, experienced outsider that they won’t say to a colleague they’ll sit across from on Monday morning. Twenty-five years of doing this has taught me that the quality of the outcome is directly proportional to how safe people feel to disagree in the room. That safety is very hard to create internally, no matter how good your culture is.
STEVE: Duke, how does Perpetual actually decide the right mix of activity — socialising, learning, creating — for a given client?
DUKE: It starts with a real conversation, not a template. We want to understand the current situation — what’s actually going on with this team, what’s getting in the way, and what “better” looks like for them. From there we map objectives against those three categories so we’re not guessing. A team launching a new strategic initiative needs a very different agenda from a leadership team that’s just been through a merger and needs to rebuild trust before they can even talk about strategy.
NIGEL: And we’re honest with clients when an offsite isn’t the right tool. Sometimes what a team actually needs is a shorter, sharper working session, not three days at a lodge. Our job is to protect the return on that investment, not just fill an agenda.
STEVE: What role does location really play in all this?
NIGEL: A bigger one than people expect. Getting a team physically out of their operational environment is what signals “we are working on the business, not in it.” I’ve run retreats everywhere from a ski lodge in Lake Tahoe to a Kasbah in the Atlas Mountains, and the common thread isn’t luxury, it’s distinctiveness. The venue has to give people permission to think differently. A generic hotel conference room rarely does that, no matter how nice the coffee is.
STEVE: Walk me through how a client actually works with Perpetual, from that first conversation through to the retreat itself.
DUKE: We start by understanding the situation and the desired outcome together with the client. From there our team builds the project charter — theme, objectives, roles, timeline, outline agenda — and that becomes the backbone of everything else we do. Depending on the scale, we’re sourcing and vetting locations, building the agenda session by session, and bringing in the right facilitation expertise, whether that’s organizational psychology, strategy, or team development.
NIGEL: Then we show up and run it. That’s the part clients remember, but it’s the 5% visible on the day. The other 95% is the planning discipline behind it, and that’s exactly where most companies underinvest.
STEVE: Let’s talk about size. Does any of this change for a six-person leadership team versus a 500-person all-company retreat?
NIGEL: The principles don’t change, the mechanics do. A six-person leadership team can have a genuinely fluid, responsive agenda, we can read the room and adjust in real time. At 500 people, you need much tighter choreography: breakout logistics, multiple facilitators working in parallel, a clear plan for how smaller-group output gets reported back to the full group. The mistake companies make is applying small-team thinking to a large-scale event, or vice versa, over-engineering a six-person offsite until it feels like a corporate conference.
DUKE: Scale also changes the facilitator’s job. With six people, I’m in the conversation, almost a participant. With 500, I’m conducting an orchestra, I’m rarely the voice in the room, I’m making sure the right voices get the floor at the right moment. Both take real skill, they’re just different skills.
STEVE: What’s the single biggest mistake you see leadership teams make when they try to run an offsite themselves?
DUKE: Overloading the agenda. Leaders get one rare block of time with the whole team in a room and their instinct is to fill every minute, because who knows when they’ll get this again. That instinct is understandable and it’s almost always wrong. We’ve seen agendas with barely a break in two days. People stop absorbing anything by mid-afternoon on day one. Our job is often to take a client’s draft agenda and cut 30% of it, not add to it.
NIGEL: The other one is skipping the follow-up. Teams pour weeks of planning into the two or three days together and then treat the Monday after as, well, just another Monday. Without a deliberate plan to carry the energy and the decisions forward, whatever alignment you built starts decaying almost immediately. We build the follow-up cadence into the plan before we’ve even booked the venue.
STEVE: How do you actually measure whether an offsite worked? A CFO is going to ask for more than a good feeling.
NIGEL: Rightly so. We push clients to define success measures at the same time they define objectives, before the event, not after. If the goal was strategic alignment, we’ll run a short diagnostic beforehand and again afterwards, and again a few months later, because we know that alignment peaks about a month out and fades if it isn’t reinforced. If the goal was a decision or a plan, the measure is simple: did the actions actually get implemented in the following quarter?
DUKE: I’d also say, don’t ignore the qualitative signal. When you get it right, you can feel the difference in how a team talks to each other in the weeks after, more direct, less politics, faster decisions. That’s harder to put in a board deck, but it’s often the most reliable early indicator that the harder numbers will follow.
STEVE: Last question, and I’ll let you both answer this one. Why should a leadership team bring Perpetual in for their next strategic offsite, rather than run it themselves?
NIGEL: Because we’ve done this hundreds of times, across industries from consumer goods to financial services to steel, and we know what works. We’re not learning on your dime.
DUKE: And because the highest-performing teams we work with aren’t defined by strategy alone, they’re defined by trust. Building that trust, and turning it into real business outcomes, is a craft. It’s what we do, every single time we run one of these events.