For a long time, I thought of culture as something we had, not something we did. That changed in a food pantry in Puerto Rico.
We were there as part of a service trip for our annual company retreat, where our globally dispersed team spent several days volunteering, meeting, and relaxing. We were not a broken team looking to be fixed. We already liked each other, already worked well together, and already felt comfortable saying hard things when something wasn’t right. We went not because something was wrong but because we believed in giving together as a group, the same way we try to do business together. What we didn’t expect was how much it would reveal about what we already had.
The pantry was a mess when we arrived. Boxes everywhere, no clear system. But we didn’t stand around long. Someone grabbed a box and started sorting, someone else fell in next to them, and within an hour, we had an assembly line going without anyone calling it that. Music on, cases moving fast, people who normally only see each other on a laptop screen working shoulder to shoulder. It didn’t feel like team building. It felt like us.
“We found our cohesiveness,” said Abby Flamholz, our CIO, when we debriefed at the end of the trip. I think what she meant is that we had always had it, but we had never quite felt it this way before. We had sat around dinner tables together. We had never built something together outside the context of the business.
A few days after we got back, she brought something up with a colleague that she’d been sitting on for a while. She told me she had raised it because, for the first time, she felt she really understood how he would think about it. The trust was already there. The trip had given her something else: a sense of the person.
That was the first time we’d done anything like this. It won’t be the last.
What Today’s Employees Are Asking
Hiring feels different now, at least in our world. When I sit down with a candidate who is serious about joining our company, the salary conversation usually settles itself. Many of the late-stage conversations I’ve had in the past few years arrive at the same question, sometimes asked outright, sometimes circled around sideways: What does this place actually stand for, and will I feel it day-to-day? One candidate last year passed on a higher offer somewhere else. When I asked why, he was pretty direct about it. That’s a different kind of conversation than I was having 10 years ago.
Remote and hybrid work is part of why that question matters more now. Our team is spread across time zones, and most weeks, people who genuinely depend on each other only interact through a screen. That works in a lot of ways. But it doesn’t easily produce the kind of familiarity that builds up when people share physical space: the shorthand, the ease of reaching out without a reason. You can have a high-functioning distributed team and still be missing that layer. Most of us are.
The Puerto Rico trip added depth to something that was already working. Our team came back with shared references and a felt knowledge of each other that is hard to manufacture and impossible to schedule. For businesses trying to hold onto good people, that matters.
Why This Changes the Work
The people we serve are trying to make good decisions about money that took them decades to accumulate. They are not just buying an investment process. They are deciding whether they trust the people on the other end of the phone. That trust is built on judgment, and judgment is partly a team sport. How quickly does someone surface a concern? How honestly do people talk to each other internally when something isn’t working? How well does the left hand know what the right hand is doing?
A team that has done something genuinely hard together and has relied on each other outside the normal context of client work carries itself a little differently. In our debrief after the trip, the thing people said most often was that they now knew their colleagues in a way the work itself had never quite produced. Not that they hadn’t trusted each other before. They just knew each other more fully now. That might sound like a small distinction. In an advisory firm, it is not.
Client relationships run on confidence in people. How those people know each other is not a separate question.
What We Actually Did
The trip was three days. We did two service projects: the food pantry, and a day helping build a playground at a school for children with special needs. The school’s outdoor space had been badly damaged by storms over the years and hadn’t been properly restored. We also had strategy sessions woven in, and some time that was just unstructured, including an evening kayaking through Bio Bay, one of Puerto Rico’s bioluminescent bays, where the water lights up around you as you paddle.
Both service projects were set up and run by OU Relief Missions, an organization that has been working with these communities for years. They were there before us, and they’ll be there long after. Our job was to show up and do what we were told. We weren’t designing the solution. We were helping with work that was already defined, already supervised, already connected to a real plan. The food boxes had somewhere to go. The playground had kids waiting for it.
Three Things That Determine Whether It Works
Not every corporate volunteer trip delivers what ours did. Some are well-intentioned and poorly run. Some end up serving the company more than the community. Based on what we learned, three things seem to matter most.
1. Make Sure the Work Is Actually Needed
Go through a partner with real roots in the community, not one that builds a project around a corporate schedule. Ask who identified the need, who supervises the work, and what happens after you leave. On our trip, the pantry project had a specific deliverable, trained supervisors on site, and a distribution plan that existed before we arrived. We were extra hands, not the people running the show. That is the right setup.
2. Build It So Everyone Can Genuinely Participate
Physical intensity varies on these trips, and not everyone can do everything. If families are invited, covered expenses need to be fair and clearly communicated upfront. It should also be stated, not just implied, that not going carries no career penalty.
We invited family members, and it made the trip richer. Seeing each other with kids and partners added a dimension to relationships that professional settings rarely allow. But it only works if the ground rules are clear from the start.
3. Plan for What Happens When You Get Back
The trip is not the result. What people carry forward is the result. We built strategy sessions into the itinerary while the energy was still high, ran a real debrief before we flew home, and stayed attentive in the weeks after to see how people were engaging with each other. A volunteer trip with no follow-through is just a few nice days. With intention behind it, the investment compounds.
The Case for Doing Both
None of this is free. Our trip cost real money: flights, hotel, meals, and a few days when our people were not available to clients. Anyone evaluating this honestly has to include all of that. I am not arguing that it is cheap. I am arguing that what you get in return is something genuinely hard to build any other way: a team that knows each other not just professionally but as people, that has a shared history outside of work, that carries a genuine knowledge of one another into every client conversation and every difficult internal moment that follows.
Beyond the time and travel, we also made a financial donation to OU Relief Missions to support their ongoing work in the communities we visited. The trip was not just a use of time. It was a deliberate choice about where to put resources.
Our clients are watching what we do, not just what we say. A firm that invests real time in something outside its own interests tends to find that it gets remembered.
We went to Puerto Rico thinking it would be a good experience. We came back understanding our team a little better than we had before. That turned out to be worth more than we anticipated.
David Wertentheil is CEO and Partner at Worth Venture Partners.
Photo courtesy Leire Cavia for Unsplash+
