Growing beyond Airbnbs and homemade bacon: A look at Tidepool team retreats

Here's a fun fact: Tidepool is a completely remote, distributed organization. We all work from home. All 42 of us. We have no office.

There’s plenty to share and discuss about how we do things at Tidepool – including the tools we use like Slack, Jira, Zoom, and the value of a space to share pet pictures – but for now we want to talk about one of the things we do that makes Tidepool an effective place to work: our team retreats.

Twice per year, we get everyone together. In person. Together. For a whole week. We do this for lots of reasons:

1. We use the opportunity to reflect on the last six months (what went well, what could go better).
2. We have guest speakers come talk to us to inspire us. In the past we’ve hosted Adam Brown (diaTribe, Close Concerns, and Bright Spots and Landmines author), Aiman Abdel-Malek, Ph.D (former CTO at Insulet), Sarah Lucas (Tidepool Board Member, former CEO of Beyond Type 1), Saleh Adi (Tidepool Board Member, Tidepool co-founder).
3. We usually cook together. We go on hikes together. We go bowling. Shared experiences build trust and camaraderie. This trust lasts us for a long time. Read "5 Dysfunctions of a team" if you want to learn more about why this aspect is so important.
4. Most importantly, we plan projects and have product and technical debates together. Being together in person, being able to do on-the-fly breakout sessions, and stand at whiteboards together, is an incredibly high bandwidth mechanism for planning out our next six months and making important product, strategy and technical decisions. Don't get us wrong, we love working remotely and have developed mechanisms to make it work really, really well (and we'll blog more about that part soon), but combined with the #3, being together at the onsite is a key part of making that remote time work well.

This fall, our offsite is a little different. For starters, we're not calling it an "offsite." Someone figured out that if we're always working from home, there's no place we can go to be "offsite", so it's really an "onsite." Because we're all together...and semantics are weird: onsite. OK fine. Check.

The other thing we're doing, for the first time ever, is going to a hotel. And not just any hotel, we're going to the Waldorf Astoria in Park City, Utah. Wait, what?! The Waldorf? In ski country Utah? Aren't you a 501(c)(3) nonprofit?

Yes.

And here's the wonderful and crazy thing: The Waldorf Astoria Park City, bless their hearts, are giving us an AMAZING nonprofit discount. Rooms are similar in price to most major hotel chains. They aren't charging us to rent additional meeting spaces, or A/V equipment. And because it's off-season, and they are doing a "refresh" of their rooms, we mostly get the place to ourselves.

So let us just pause right here and say: Thank you Waldorf Astoria Park City for supporting our mission, for giving us an incredibly generous nonprofit break, and for providing us a place to stay where we can plan the next six months of Tidepool and Tidepool Loop awesomeness.

But why go to a hotel when we've done just fine sleeping in basements and bunking in Airbnbs? Well, In the past, we've been pretty fortunate - we'd always been small enough that we could all fit in Howard's house (including 4 on the floor in the basement).

Then we had an awesome stretch at the ranch of one of our former board members near Mt. Shasta, California. It was hard to beat the breathtaking view:

The downside? For most of the day, the rural location meant no internet. On one hand, the opportunity to focus with limited distractions was great, but when you build software for a living, and depend on cloud services to build that software, that complicated things a bit and made it pretty hard to work on things.

Then we started staying in rental houses in Santa Cruz. This was pretty awesome, too, and we loved being able to take long walks on the West Cliff Beach to work out hard problems or enjoy the ocean view. But it was hard to get to for everyone, and ended up being pretty costly to get there from a ground transportation standpoint. As much as we loved our Santa Cruz retreats, we had to acknowledge that we outgrew that space.

At our last offsite, we stayed at Howard's house again, and a few other local Airbnbs. This was fun, but since we were up to 30-something people, it was a squeeze.

As in the past, we did a lot of room sharing, but this time with a really rough consequence. About ⅓ of the team got really, really sick.

Particularly when you are a team with pancreas in the game, this is not a good thing. A bunch of folks were out for a solid week after offsite, recovering from the nasty bug.

Tidepool is growing. Our team has expanded so that we can deliver Tidepool Loop as soon as possible. And as part of growing, we've had to grow beyond Airbnbs and homemade bacon (thank you, Katie DiSimone!). Well, beyond Airbnbs anyway.

This year will be our first Tidepool Team Onsite held at a hotel. We did the math, and it not only makes sense from a financial standpoint, but it also means more time for us to focus on the next six months of progress, and less time spent making food for more than 40 people and (hopefully) less time getting each other sick.

So why are we telling you all this? A few reasons:

1. If you are a nonprofit organization, don't be afraid to ask for free stuff or for deep discounts. We do it all the time. Companies love helping out nonprofits doing some good in the world. It makes them feel good, and helps you fulfill your mission. (We get a ton of great discounts. See the “Tools and services” section here.).
2. You'll probably see some tweets, Facebook posts, and Instagram stories from us next week from the Waldorf Astoria. Yes, those are beautiful mountains in the background. No, we are not being irresponsible with our donor or grantor's money. When we take into account all of the credits the Waldorf Astoria Park City is giving us for things like meeting room fees and A/V equipment, staying there ends up being the same as quotes we received from other big-name hotel chains, and we're also saving a ton of money on air and ground transportation. In fact, this onsite will only cost $350 more per person than the last one. Considering all the benefits we’re receiving from the Waldorf Astoria, we couldn’t be happier with how this planning effort has come together.
3. As mentioned earlier, we'll blog more soon about all of the other great things that we do to make remote working work. But this point is key: We feel strongly that in order to be an effective remote team, you have to get everyone together regularly to build trust and camaraderie, and to have the fierce debates and planning sessions that let you get things done for the rest of the year. Offsites, well onsites, are the way we do that at Tidepool.