I believe that:

1. Teams that have deeper personal connections perform better.

2. Remote teams generally have shallower personal connections.

At Stellate, we knew from the start that we were going to build a remote team.¹ So, we asked ourselves: How can we foster deeper connections in our remote team?

Sue Odio and I tried many ideas, and we eventually settled into this rhythm:

Offsites: Every four months

We ended up settling into a rhythm of three company-wide offsites per year (so one every four months), with 1-2 additional team offsites per year on an as-needed basis to work on a specific topic.

This rhythm felt like a good fit:

1. The few times that we went longer than four months without an offsite, I noticed how much more disconnected we felt the next time

2. The few times that we went shorter than four months until the next offsite, I thought it felt “unnecessary” as the personal connections were still strong

When teams had specific projects to work on (e.g., onboarding a new manager or figuring out our product process), they would additionally schedule departmental offsites on an as-needed basis. In practice, we never needed more than one of those per year.

Game meetings: Every two weeks

Every two weeks on a Friday, we would get together for our no-work connection meeting. Usually, we would hang out for a bit and then play some virtual games together. Every now and then, team members would also self-organize and play other “actual” games like Minecraft.

Some of our favorite virtual games

These are all the games we played many times in these connection meetings; none require much (if any) instruction and can be played in people’s browsers.

1. Codenames

2. Jackbox Games, especially Drawful (although Draw Battle below is equally fun)

3. Make it Meme

4. Gartic Phone

5. Draw Battle

Fun once but not multiple times: Death by AI

Checkin questions: Every day

As a remote company, watercooler conversations are difficult to come by. Sue Odio introduced check-in questions as a standard part of our recurring meetings to get some of that connection energy back.

For the first 10% of the meeting (e.g., 3 mins of a 30-min meeting), we go around the room and everybody answers a random icebreaker question.

Learnings:

• Personal, yet not too-personal, questions work best.

• Work-related questions generally don’t work well because they aren’t safe for people to answer.

• Instead of phrasing questions as extremes (“your favorite,” “the worst,” etc.), phrase them as “one of.”

  • Asking for a single response (“your favorite”) makes the question more difficult to answer, and people tend to go “Phew my favorite hmm I have to think about that…”

  • For example, instead of asking “Who is your favorite sports player?” ask “Who is a sports player that you love?”

Examples:

• Great (a bit more personal): “Which of your teachers left an impression on you?”

• Great (a bit less personal): “What is a food you could eat every day?”

• Too extreme: “Who is your favorite sports player?”

• Too personal: “What’s one of your big regrets?”

• Too work-oriented: “What do you think about working at this company?”

---

1. If I were to found another startup, I’d be in-person in a room until we have PMF and only hire remote team members once we scale. The communication/collaboration overhead of remote work is deadly for nascent, early-stage startups who have to iterate quickly; Stellate survived this stage by pure luck of the funding environment, but it was unnecessary additional risk.↩