Are partner retreats still a thing?
I was at a dinner recently surrounded by a few successful entrepreneurs, complete with a plate of squash gnocchi, a glass of pinot grigio and dim lighting (my fav lol).
We were all just generally chit chatting - actually I believe we might have been talking about waterbeds… what can I say, I am a child of the 80s - when the topic of partner retreats came up.
You know what I’m talking about: those 5- or (gasp) 6-figure getaways where owners and sometimes spouses go to some glamorous location to eat, drink, play golf, relax at the spa, and maybe have a meeting or two.
Potential locations include Whistler, Mont Tremblant, Tulum, Oak Bay, Fogo Island ... you get the idea.
A lot of these retreats disappeared after the COVID-19 pandemic.
But what disappeared wasn’t just the $85k travel budget - it was one of the few moments owners actually slowed down enough to step back and work “on” their business, instead of just “in” it.
So are pricey partner retreats a thing of the past?
No, I’m not convinced they are. This might surprise you given that my middle name is “profitability” haha. Let’s discuss.
---- >>> And before you tune out thinking “this doesn’t apply to me - I don’t have business partners” - stay with me. Because if you’re the sole owner, you are the partner group. And that means every strategic trade-off, every deferred decision, and every “I’ll deal with that later” thought lives entirely in your head. Aka it also needs time and space to be dealt with.
What’s the point of a partner retreat?
In my opinion, any effective partner retreat must accomplish two things - otherwise it’s just a very, very expensive off-site:
1. Strategic Alignment
Everyone gets on the same page about what game they're actually playing.
An example: On paper, all partners - or you, if you’re the sole owner - agree the firm wants to “grow.” But at the retreat, it becomes clear:
One partner wants to double revenue in three years and bring on 6 new equity partners
One wants to target 4% organic growth per year aka stabilize, keep the team small, protect lifestyle, and
One is thinking about the inbound offer from a national firm.
No one is being difficult. No one is “wrong.” They’re just dreaming of different outcomes on very different time horizons - and no business can do all three at once.
I see the same dynamic with solopreneurs too - again, on paper, you want to “grow,” but in reality, you’re torn between hiring another team member, investing in new tech, or expanding into the office space next door that just opened up.
And without a forced pause, those trade-offs never get decided - they just get tabled or deferred until who knows when.
What the retreat creates is the space to say the quiet part out loud and make a choice like: “For the next 12 months, we are optimizing for profitable, sustainable growth at a rate of 5% - not maximum scale, not an exit.”
From that point on everything gets easier - hiring decisions, tech investment decisions, partner meeting agendas, etc…
2. Decision velocity
You finally make the hard calls you’ve been avoiding.
Another example: maybe there’s a senior team member everyone tiptoes around. They’re well-liked, long-tenured, and have deep institutional knowledge.
But the role has outgrown the person and everyone knows it. Left unresolved, this becomes an organizational bottleneck - not just a people issue.
At the retreat, the issue gets named:
the role isn’t aligned with where the firm is going
a transition needs to happen this year
someone owns the timeline
Nothing happens that day - but the decision is made.
That’s the real power of the retreat: not forcing action, but eliminating decisions that just drag on and on.
You may notice “relationship building” still isn’t listed as one of my two formal objectives. The golf, the spa, the 7-course tasting menu dinner (with wine pairings) aren’t a specific “outcome”. They’re the things that make the entire retreat possible.
Why? Well, they create enough psychological safety for people to say what they won’t say in a boardroom on a Tuesday afternoon in downtown Saskatoon. Strip that away, and you get a rushed off-site where hard topics appear on the agenda… and get tabled. Again.
At the end of a successful retreat - whether you have partners or you are the partner group - you should be able to say:
I’m clear on where we’re going and why.
I know exactly what decisions were made and what I own next.
And when owners leave with that level of clarity, the firm doesn’t just feel better, it operates better because everyone is finally rowing in the same direction.
Anyway - food for thought (preferably with good wine).