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Cat Herding Distributed Teams

Introducing "Team, Assemble!", a tool that helps distributed teams meet up in person

July 3, 2024

Team, Assemble! is an app that helps distributed teams figure out the most cost-effective destinations for an in-person offsite.

The following outlines the origin story and motivations for the project. If this sort of thing suits you, by all means read-on.

You can also skip ahead to demo below.

I suppose data platitudes would’ve sufficed, but my real motivation for building Team, Assemble! was that I was tired of justifying why it was cheaper and more effective to run offsites almost anywhere other than my old company’s headquarters in Cleveland.

Let me explain.

Cat Herding

Bringing the Band Together

I’ve long advocated for hiring the best talent regardless where they live. (Provided the operating model allows for it.)

Allowing people to build their work lives around their personal lives—and not the other way around—is a north star that informs my operational biases:

The RTO (return-to-office) crowd says “remote” is no way to build a culture or a company: you need “real” in-person face time to build trust and camaraderie. While they’re wrong, they’re not completely wrong.

Experience tells me that while distributed teams can work and work well, they work even better when they meet up regularly. Experience also tells me that the minimal effective dose for meet-and-greets is small (between 1-4 times a year in most cases).

All told, bringing a distributed team together is far less costly than forcing a co-located team into a leased office space every day… and what a person, team, or company deems costly varies widely.

Which brings me figuratively (and literally) back to Cleveland.


Cleveland Rocks

On each super-commute, I made a point to learn more about the city.

I had no idea, for instance, that Lake Erie connects to the Atlantic Ocean, greatly contributing to Cleveland’s cultural import and diversity… not to mention some impressive architecture and culinary options.

Super-commuting was also surprisingly easy: I could leave my NYC apartment at 6am and arrive in the downtown Cleveland office before 9am, often beating my local colleagues.

22 minutes to the airport, 8 minutes through security, 5 minutes to gate, 96 minutes in an airline seat, 7 minutes gate-to-curb, 15 minute taxi to office. Total block time: ~2h35m, give or take 15 minutes.

Timing and service was so reliable that I would often day-trip rather than spend the night.

Coming from a major east-coast city with three International airports, this was easy and affordable. So easy, in fact, it’s easy to forget how, for other people originating from non-major, non-east coast cities, flying my team to Cleveland (and housing them all) had some significant hidden costs.

Real Costs, Real Problems

As my reporting line grew from 5… 15… 40… 80… and so on, the origin counts and unique travel considerations for teams and sub-teams grew geometrically. Folks hailed from everywhere: San Francisco, Rio de Janeiro, Salt Lake City, Raleigh, Toronto, Miami, and yes some in Cleveland. Even with historically-low flight prices, hosting an on-site in Cleveland was becoming surprisingly expensive, even with some of my team living there.

Here’s why:

  1. Time costs. Cleveland has many direct flights. However, not all routes are served by my team’s preferred airlines, so many opted to chase status with a layover and/or avoided certain air carriers. (n.b. I am often this person… there is no judgment here.)

  2. Flight costs. Market dictates prices, not distance. As of this writing, from NYC it costs half as much to fly to Denver than it does to Washington D.C., even though it’s 8x the distance.

  3. Hotel costs. While the downtown office space was paid for, downtown hotel prices vary wildly depending on the season and availability. (It is very inexpensive to visit Cleveland in the winter—hope you like it bone-cold.)

  4. Surprise costs. Seasonal price fluctuations aside, coincidental events had major impact on prices. Some of my most expensive visits to Cleveland coincided with high-school volleyball tournaments, collegiate parents’ weekend, and various health conferences where hotel and restaurant availability was severely limited. As there’s no universal directory of events (I know this because a previous company of mine tried!), there’s no way I would have known. Had I accidentally planned a team get together during any of these times, I would have burned budget needlessly.

  5. Safety concerns. From a macro perspective, data shows the planet continues to become safer and more peaceful (climate change notwithstanding). That macro trend is at odds with some short term realities. Take the United States. With its uneven healthcare availability, differing interpretations of human rights, and a general distrust for authority, it would be foolish not to recognize that not everyone will feel safe traveling everywhere. (These are not always concerns an employee may wish to express to their employer and/or manager directly.)

Ultimately, what teams consider costly differs.

Discovering those costs (and perceived/actual costs/risks) is also expensive.

Making and Avoiding Expensive Mistakes

I was coordinating an offsite for a six people, including myself. After working out all the concerns listed above for the six of us, Nashville was the turned out the “best” place to assemble for our quarterly offsite.

It was also COVID/flu season, and after two of our six were compelled to “stop the spread”, we had to delay. Given the effort to determine that Nashville was the place, we naturally re-booked the trip.

This was a costly 5-figure delay.

In two-months, hotel prices had risen 200% with no more rooms available in downtown Nashville. The best we could do was a hotel near Vanderbilt. No time to replan, I fully committed and ate the difference.

In an act of risk mitigation from the bean counters, I wanted to make sure there was no other option, however creative. I found only one: it was an AirBnB-listed apartment in downtown Nashville that had 7 bedrooms, each with an en-suite bath, and a very large living-room/kitchen area adjacent to our own outdoor space. It was newly-constructed so that each room was like a mini-suite. It could have as well have been an actual Bed and Breakfast for all I know. The property manager even claimed that they soundproofed each room for maximum privacy.

This listing was essentially a 7-room, 3-star bed and breakfast with no receptionist… but I wasn’t sure if my team would all feel comfortable because a hotel it was not. With respect to my budget, this choice would have put the trip very close to the pin; but, I could see how some might find it too cozy, and any personal discomfort from one of the participants would have had the opposite of the intended effect of the retreat.

I wasn’t sure. But, with my mind set on protecting budget and maximizing fun, I e-mailed the team explaining the AirBNB’s unique and private layout with an impassioned pitch to at least consider it; and, if there was a single objection to this lodging arrangement, we wouldn’t do it. Any objection would be held in confidence.

I don’t remember the exact message that came back 30 seconds later, but I remember the subtext: Fuck that. No. Absolutely not.


I quickly walked-back that first e-mail and informed the team I was able negotiate an excellent deal at a large hotel near Vanderbilt University after all and to never mind that other idea.

It went fine.

Missed Opportunities

I bring up this anecdote to highlight two points and what-ifts.

Had I booked atypical lodging without asking my team for their approval first, I ran the risk of making my colleagues uncomfortable. The main point of an offsite—particularly this offsite—was to build trust between teammates. What if I decided to do it anyway? Would my team trust me in my other decisions? Would they they see me as one who put minor budgetary concerns over their own personal needs and comfort? What would the long-term effects of that be?

On the flip side, I could see opportunity.

What if there was something that all six of us would have loved to do together. What if we all wanted to rent out an actual Bed and Breakfast on a lake or a mountain instead of staying in downtown Nashville? What group activity were we missing out on that all of us would have loved doing, but never would have volunteered? Bowling? Karaoke? White-water rafting? I think about all these missed, shared opportunities we could have had had there been a way to surface these preferences without too much effort, while avoiding any “absolutely-nots” from any one participant.

Shared experiences increase understanding, and understanding breeds trust. How can we find ways to be more inclusive, but not boring about it?

What if everyone on a team actually likes ropes courses and corporate trust falls—that would be something, right?

What’s the matter with Cleveland?

Nothing at all. Cleveland’s great!

But, for a hypothetical 100 person team that resembled the geographic diversity of my reporting line, there are far better options for a 4-night trip. Here’s an actual run-up of the costs associated with different places from real pricing data:

(Negative savings means more expensive.)

Destination 💵Dollar Savings ⏱️Time Savings How Many Live Here? Notes
Cleveland, OH - - 8 Reference Location.
New York, NY -30% 30% 12 If time is money, this broke even.
Denver, CO -40% 0% 0 Much more expensive, but equivalent time cost.
Las Vegas, NV 10% -25% 0 Saved 10%, but adds 200 hours in collective travel time. Cheap lodging, could extend trip.
Miami, FL 5% 0% 0 Cheaper, and everyone gets to travel.
New Orleans, LA 0% -3% 0 Everyone wanted to go here, cost the same as Cleveland.

For this actual run of the numbers for this hypothetical team, the differences between the least expensive and most expensive trip could be thought of in terms of 2 FTE salaries on the dollar costs, and about 600 hours of lost work-time (15 weeks time-loss across the 100-person team).

Picking the wrong destination for this hypothetical trip could have needlessly cost the company $200,000.

What’s more: a few months later I re-ran the calculation, and Cleveland became more than twice as expensive in $-terms as NYC, with 30% more travel time.

Estimating these costs are tricky because when you want to a place can be a larger factor in pricing than where you want to go. When it comes to group travel, costs can really add up in unpredictable ways.

So Now There’s An App For That

Given the $200K in potential savings from one trip alone, I suppose I could’ve justified the spend in building a functional tool for this in-house. But, I also believe that companies should build what’s core and buy what’s not because of the opportunity costs associated with doing everything in-house.

If you plan team trips, please give Team, Assemble! a whirl. A $20 team travel estimate could save you $200,000—and give you hours back to do the work that matters.

And if you don’t, here’s who on your team might benefit:

As we’re just going live after 21 months in development, we very much welcome the feedback.

Product Demo and Introduction

Visit to give it a try.

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