Shoulder to Shoulder
This post connects its title to Jerry Colonna's "shoulder to shoulder" leadership posture, then shows how Sara and Mathias used it at their own offsite by getting vulnerable with their team first. The real point: good offsites depend on honesty and pre-work before the room and follow-through after it, not the venue or activities.
Before I get into the topic of offsites itself, I want to name where the title of this post comes from, because it's not just a nice image to me. Jerry Colonna, who is an author and co-founder of the executive coaching firm Reboot, talks about leadership as a choice between three postures: standing in front and clearing the path, standing behind and pushing, or standing shoulder to shoulder and saying, "It's a hard road. Watch out, there are potholes over there." He writes about this in Reboot: Leadership and the Art of Growing Up, and that third posture is the one I try to lead from. It's different from both a top-down hierarchy and simple face-to-face collaboration. It's not about direction, or who's ahead of whom. It's about proximity and stance: walking the same road, at the same pace, taking on some of the same risk. It dismantles the assumption that the leader already has the answer and is just waiting for everyone else to catch up. It's an act of empathy before it's a management technique.
Shoulder to shoulder is exactly how Mathias and I tried to show up for our own company offsite. Prior to our offsite, we had lost our way with each other, and it took a podcast episode (with Jerry himself!) for us to realize that we needed to show up differently, first for each other, then for our team.
Now that I've explained why I've named this post "Shoulder to Shoulder," let me dive into this week's pocast episode.
When you say the word "offsite" to most people and watch their face do a very specific thing. It's the trust-fall face. The forty-slide-deck face. The we-flew-across-the-country-to-end-up-exactly-where-we-started face.
Mathias and I talk about this in our latest episode, and it got me thinking about how many offsites I've sat in over the years, as a founder, as a CPO, as a coach watching from just outside the room, and how rarely the good ones look like what people expect.
The best one I can point to didn't happen in a fancy venue. It happened with a leadership team that sat on the same floor, every single day, and still discovered, through a simple pre-offsite survey, that we were each quietly running our own version of the strategy. Same floor. Different companies, basically. Proximity had made us feel aligned. It hadn't actually made us aligned. That one session, maybe ninety minutes long, did more for that team than the entire rest of the year combined.
And then there's Palm Springs. If you listen to the episode you'll get the full tennis story and the Olive Garden breadsticks, which I won't spoil here. But the part I keep coming back to isn't the fun stuff. It's what Mathias and I decided to do before any of it. We stood up in front of the whole team together, shoulder to shoulder, and talked openly about our own partnership: the friction, the differences, a German and a Californian figuring out how to run a company together. It wasn't comfortable. It also wasn't optional, in my mind. If we wanted anyone else in that room to be honest, someone had to go first. Someone with less to lose than the newest person on the team.
That's the thing I don't think gets said enough about offsites: the room takes its cues from whoever's most senior in it. If leadership shows up polished and all-business, that's the permission slip everyone else takes. If leadership shows up a little exposed, that's a different permission slip entirely.
The other thing I've come to believe, mostly the hard way: an offsite is not where the thinking happens. It's where the talking about the thinking happens. Every offsite I've watched go sideways had the same root cause: nobody did the homework. We showed up to brainstorm cold, in a room, in real time, which is a genuinely terrible way to get anyone's actual opinion, especially the quieter people in the room. The offsites that worked were the ones where people had already wrestled with the questions on their own (through a survey, a prompt, a page of notes scribbled on a plane) and arrived ready to build on something instead of starting from nothing.
And then, of course, there's what happens on the Monday after. This is where good offsites quietly die. All that momentum in the room, the flip charts, the little bursts of "oh, we should really do that," none of it survives contact with a full inbox unless someone wrote it down before everyone scattered. Who owns what. What we actually decided versus what we just talked about. When we're checking in again. It's not glamorous, but it's the difference between an offsite that changes how a team works and one that becomes a slightly nicer memory.
If you run offsites, or dread them, or are trying to figure out whether your team even needs one, Mathias and I go deep on all of this in the episode, including the very real difference between prepping a co-located team, a hybrid one, and a fully remote one. And yes, the tennis story is in there too.
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