Glamping on a cliff: Inside Gilligan Sheppard’s annual conference

I had never been to a work conference before. As a graduate, I’m fresh skin not only to the firm but to the industry itself. So, when I arrived at the cliffside glamping site, I had nothing to compare it to. Just fresh eyes. Here is what I took away. 

Setting the bar on day one

Glamping on the edge of a cliff is as cool as it sounds. The team at Cliffside Glamping did an incredible job setting up the facilities to create an environment that fosters connection naturally. It was the perfect backdrop for a conference of this size. The food alone was deserving of a special mention, especially the salmon and steak.

During our first session of the conference, Joshna asked each of us what we wanted to get out of the conference. We had to think introspectively about our values and set the tone for our experience. After some thought, I wrote ‘Deepen relationships, understand the Gilligan Sheppard (GS) values, and become a pro at Frisbee golf.’ I was only half joking.

Matching behaviour to our values

When you are new to a firm, you absorb the culture through osmosis. You pick up how people talk to clients, how they treat each other, what gets celebrated and what gets corrected. You form an impression of the values, but you don’t always hear them said out loud. 

At conference, Joshna gave them a practical shape. She talked about delivering with integrity, setting clear expectations and not over-promising. About noticing opportunities to deepen client relationships through conversation, not through being a “salesperson.” About showing up each day with the intention to be productive and owning your outcomes. About picking up the phone, because it’s still the fastest way to solve a problem and build trust. About staying open to learning and choosing to see change as opportunity rather than threat. And about maintaining an environment that’s both supportive and performance-driven, where feedback is welcomed. 

Everything I had already noticed in practice, how teams approach client problems, the way staff invest time in each other, it all came back to what she was saying. It’s one thing to sense that a firm has good values, it’s another to hear them said explicitly and realise you’ve been experiencing them in practice all along.

The only time competition is better than collaboration

Gilligan Sheppard is, by any measure, a collegial workplace. Supportive, generous, always looking out for one another. You could work here for months and never see someone’s competitive streak.

Staff Olympics and frisbee golf were where I saw this schema start to crack.

We were split into teams and thrown into egg and spoon races, hoop throws, ring tosses, and wheelbarrow carry races. What started as casual fun escalated fast. There were disputes about technique. There were accusations of early starts. There were people running wheelbarrow carries with the kind of intensity you would normally associate with a soldier crawling away from the frontlines, not an accounting firm retreat. 

But here was something about putting people in silly physical challenges that stripped away whatever professional veneer GS had and got you closer to who they were, all laughing along the way. You learn more about a colleague in a three-legged race than in three months of sitting at your desk. 

Sadly, our team didn’t take the overall win for Staff Olympics. But Sahil and I did win frisbee golf, and I want that known on my digital footprint forever. Unfortunately, we made the mistake of choosing a green frisbee. Not the smartest decision, we discovered, after losing it into a black hole (patch of coastal grass). The Frisbee was never recovered, but it was a small price to pay for the medal that stays on my desk. 

An AI update from the experts

The conference featured two artificial intelligence (AI) presentations from the LedgerLab team, David Malpas and Greg Montgomery, with a contribution from Humphrey on Boris, our in-house tax AI. The first explained how large language models work. The second, “The Canary in the Coal Mine,” made the case that software engineering has already reached its domain-specific AGI (artificial general intelligence) moment, and that accounting has more in common with software than we might think. Numbers balance or they don’t. Returns comply or they don’t. 

The room’s reaction was a mix of excitement and healthy scepticism, which felt like exactly the right response. For me, I left thinking about what parts of my day-to-day work I could automate. Not replacing judgment but freeing up time to exercise it on the things that matter. 

Software engineering didn’t disappear when AI arrived, it changed, and our industry will too at some point. Being at a firm that’s actively engaging with these questions rather than hoping they go away is exactly where you want to be. 

Getting to know the team’s newest addition

In case you missed it, Gilligan Sheppard recently merged with CFO 4 U (read more here). We’ve been sharing a workspace with them for a while now, but conference gave us a chance to really learn about the business and the people behind it.

In a dedicated session, the CFO4U team walked us through what they do, how they operate, the services they provide, and where they fit into Gilligan Sheppard. For me, the standout takeaway was understanding the importance of fractional CFO services for small-to-medium enterprises (SMEs), especially startups in the growth phase. It’s a model that makes sense: fractional services for businesses that need CFO-level strategic thinking but aren’t at the scale to justify a full-time hire. 

CFO4U is going to be a serious asset in the GS family, and having that face-to-face context early makes it far easier to think about how we can work together on client engagements and be a one-stop shop for clients. 

Four wise partners

This was when things got interesting.

The format was simple: partners with decades of collective experience answering anonymous questions from the floor. The anonymity invited questions people might not have asked face-to-face, and the partners’ responses were thought out, yet from the heart. 

They talked about trials and tribulations, wins and losses, the decisions that shaped their careers and the ones they would make differently. For a graduate like me, an unvarnished account of what it takes to build something over 20 or 30 years in this industry was pure gold.

Interestingly, the same threads kept surfacing between the four of them. When partners talked about what mattered most, they kept coming back to collaboration over competition, to relationships over numbers, and to the good of something greater than self. 

What stayed with me most was the importance of relationships, not only in business, but in life. It sounds obvious, but sometimes you need to hear it from someone who has lived it across decades of practice to realise it. Relationships aren’t a soft skill that sits alongside the technical work; they are the work. Or at least the foundation on which everything else is built. 

The beauty of spare time 

Some of the best conversations at conference didn’t occur in the scheduled sessions. They happened around the bar, on the walk back to the tents, and over a second coffee the next morning when nobody was in a rush. 

In an office, there’s often always a meeting to get to, a client to call, or an email to answer. At conference, that disappears, and people allow the conversation to wander. We could speak openly, with no agenda. It meant the stories got better, opinions surfaced, and open debates occurred.

You discover that the people you’ve been working alongside for months have entire dimensions you never knew about. And it changes the way you work together. 

What I took away 

As far as first conferences go, Gilligan Sheppard knew exactly what they were doing.

It’s difficult to really get to know someone under the pressure of deadlines and client demands. But over a coffee with nowhere to be, or across a frisbee golf course, you learn how people think, what they care about, and how they operate when they’re just being themselves. That ease carries back into the office, making communication simpler, collaboration more natural, and the team more connected to where the business is heading.

Not bad for three days of glamping on a cliff.