Nikhil Sethi is a second-time founder who started his first company straight out of Northwestern. He grew it from 2010 to 2018, sold it to Accenture, got married, had kids, then his relationship to work shifted. Where his first company felt deeply tied to his identity, his second company, Workgrounds, is built around a different question: How do we create organizations that take advantage of global talent while still getting the benefits of in-person collaboration?
When I sat down with Nikhil, I got a masterclass in how gatherings can either boost or damage your culture — and why the real work isn't booking hotel rooms, but designing moments that matter. Here are three things I learned that are changing how I think about bringing teams together.
For remote or distributed organizations, moments of gathering can be equally powerful in both directions. You can create positive spikes that energize and align your team. Or you can do real damage if you poorly construct these moments.
When a gathering goes wrong, it breeds questions: Why are we even doing this? Why did I waste a week of my life traveling here when we got nothing done? Why didn't leadership think through the team dynamics that made this unproductive? Why are we more confused about our strategy now than before we met?
And these aren't cheap investments. Even if you try to do corporate travel cheaply, it's still a material spike in the budget. So if you're going to spend the money, do it right.
The problem is that most of the energy gets spent on logistics: budgeting, booking flights, sourcing hotel rooms, managing dietary requirements, accessibility needs, and the fact that some team members have never been on a plane before. All of that has to get done. But it often leaves the actual content of what you're doing when you're together as an afterthought. A scramble in the Uber ride from the airport when you finally have everyone's captive attention.
Nikhil's advice? Relieve the people organizing these gatherings of all the logistical noise so they can refocus their time on the real question: If I get 48 hours as a group, what makes those 48 hours so meaningful that the next 100 days can be utilized in the most effective way?
Here's a brutal truth about organizing team gatherings: if everything goes smoothly, there’s rarely an understanding of how much work it took to get to that outcome. But if someone has an issue — the hotel was confused about their room, the workspace didn't have good Wi-Fi, someone's severe allergies weren't accounted for — that stays with someone.
Nikhil walked me through the details required to pull off a successful gathering. You can get the most beautiful venue, perfect content, everything aligned but then last-minute changes happen. Someone gets sick and can't make it. That's another email, another DM, another back-and-forth to manage. In larger organizations with complex ticketing systems, making one change means issuing a ticket in ServiceNow or Jira or Asana, then someone picks it up, then they coordinate with the hotel, then the venue, then they confirm, then update the ticket, then message the person back. It's exhausting.
The insight here isn't just logistics. It's about respect and kindness. If someone has a fear of flying, maybe don't choose an international destination. Pick somewhere they can take a train or drive. If you can't accommodate every need, at least collect that information and listen. The act of asking goes a long way. And create remotely accessible options for people who can't attend in person so they can still participate and feel connected to the team.
The small things matter. They signal that the organization takes gathering seriously; not as a check-the-box activity, but as something core to how the culture works.
We're seeing RTO headlines every week: tech giants enforcing return-to-office, companies following suit, employees pushing back. And Nikhil was honest — Sometimes RTO is a silent layoff tactic. Other times it's justifying a real estate investment, "We have these leases, we're not letting them go."
But there's an alternative solution, and some organizations are doing something really interesting with it. Automattic and Dropbox took their existing real estate footprint and asked: Could we reimagine these spaces in a way that's actually designed for this future work model? Instead of getting rid of their offices or forcing everyone back into the historical setup, they converted their spaces into different layouts designed for spiked collaboration moments. When teams show up, the space is built for those moments — not for sitting at desks five days a week. Meanwhile, Coinbase introduced the "surge" concept, converting all their real estate (and actually expanding it) into moments of quick collaboration. Then everyone moves away and goes asynchronous.
The key insight? If you aren’t flexible and intentional — "we're fully RTO" — that's when employees get scared. It feels like something's being taken away. Once you've given people the ability to work from home, pulling everyone back into the exact historical model creates fear and resentment.
But when you design a model that still takes advantage of asynchronous time while creating explicit moments to get together, and you're thoughtful about how you design those moments, that's when it works.
Nikhil's team operates on a three-pronged approach: one synchronous meeting per week, one monthly retrospective where they can rewrite any rule, and one week per quarter where the full organization gathers in a new random location to retrospect the quarter and design new objectives. Then they go asynchronous and execute. That model only works because they've built a deeply written-down culture.
A reframe that matters: the moment you have two offices, however you define an office, you're a distributed organization. Even RTO companies with offices in multiple cities face the same gathering challenges. It's not about whether you're "remote" or not. It's about whether you have multiple locations, and whether you're designing intentional moments of connection that work for how your team actually operates.
When I asked Nikhil what gives him hope about the future of work, his answer was beautifully philosophical. As tech accelerates — more tools, more AI, more everything — there's a new realization that creativity and knowing what direction to point the engine is becoming more valuable.
He's an engineer by training, but he almost wishes he'd spent more time in the arts and humanities. He'd advise his children to really think about the attributes of humanity and life that make us human; and bring that flavor, style, and culture to their work, their tech, and how they storytell.
Those skills were always valuable, but now they're differentiators. They're the difference between something that's great and something that's remarkable. And that's a squarely human thing.
After talking with Nikhil, I'm thinking differently about gathering. Like BAM, if your team is fully remote, when we come together, it has to be intentional and meaningful. It's not just about booking the venue or the flights. It's about designing 48 hours that fuel the next quarter. It's about respecting people's needs and fears and preferences. And it's about remembering that our superpower as humans is storytelling and bringing creativity, culture, and humanity to everything we build.
Listen to the full episode of Work Made Human to hear more from Nikhil Sethi about why his childhood dream was to be a garbage truck driver, how his dad's dotcom entrepreneurship shaped him, and why storytelling is becoming a core requirement for every job function.