Remote Company Meetups: a comprehensive guide

Over several years, I've been been involved in (or led) remote team meetups (also known as off-sites) for four different companies ranging in size from 3 to 150+ employees. Over this time, I've gathered quite a few data points and have a few thoughts I'd like to share.

My hope is that this will be the most comprehensive guide you will find online on this topic. While these events are fun, they also are a key component when building a distributed team or company.

By the end of this post, you should have a better understanding of why remote meetups are important, how they work, what pitfalls you should avoid, and what things you should focus on when meeting up in person.

Meeting up in person charges the "trust battery"

This first section may be elementary, but deserves to be highlighted. Why should you meet up in person at all? Don't remote teams like working from home all the time?

The reality is that even as a remote team, there's a time and a place to meet up in real-life. Very few remote-first companies will argue with this point. 

Why is this the case?

Trust and relationship-building is accelerated when meeting up in real-life. It can also be helpful to sort out ambiguous problems as there is a fast feedback loop and you can process a variety of cues like body language or facial reactions.

Building trust happens quickly in-person, but can be sustained and maintained when apart with some work and effort.

Think of trust like a battery.

When you meet up in person, the trust battery charges quickly. When you leave and work from apart, the battery slowly (or quickly) starts to drain. There are ways to keep things from draining too fast, but sometimes you just need to recharge the battery by meeting up in person.

Do you need a trust battery recharge?

On a side note, how can you tell if your trust battery is low?

A rule of thumb I use I call the "words on a screen effect." If the people you work with feel like purely words on a screen, it may be worth your time to meet up in real-life. If you see someone's avatar and can't paint a mental picture of who they are as a person, that may be an issue. I've personally found that this starts to happen after long periods of purely asynchronous work.

I Slack back and forth with a coworker who is extroverted and bounces around when talking in-person, I should expect the messages to follow that real-world behavior.

Key takeaway: It's almost like our brains need a reminder that there is a real human being on the other end of the conversation. Meeting up in-person provides that reminder in the richest format

Remote meetups is event planning

I won't spend a lot of time on this point, but company meetups are at its core, logistics and event planning. If you are a founder and aren't particularly skilled at this, consider delegating this work to a party-planning committee or someone who really likes doing this stuff.

Building Blocks of a Remote Meetup

With the high-level principle of trust-building out of the way, let's talk about the key questions people ask when thinking about having a remote onsite.

If you read other posts online, there's a range of possibilities here, which revolves around the following possible cadences:

1. Quarterly
2. Bi-Annually
3. Once a year

Frequency?

I have participated in quarterly and annual team meetups over the course of my career.

From my perspective, company-wide quarterly meetups is too frequent, especially if you have children. I have a 15-month old son and while it's not the end of the world if I have to leave for a few days every few months, it adds up quickly. Plus, I don't really like doing it.

If the average person sits in a car commuting for 19+ days a year, and the average remote worker is at team meetups for 19 days a year, what's the point of working remotely?

I'd argue the more compelling argument for not having quarterly remote meetups is because as the company grows, this becomes extremely difficult to do. It is a logistical nightmare to try to book travel, accommodations, activities, etc every few months. You may need to hire someone FT just to do this.

If I was young and single, I'd probably enjoy traveling to nice locations on a quarterly basis for work. I'm not saying this is wrong, but I don't think this cadence will scale as the company grows, so you may want to consider a less frequent cadence from the beginning.

You will be pulled to an annual cadence (at least company-wide)

Right now, Friday is not a big company, so the plan right now is to meet up every six months or so for a few days, with some ad-hoc travel if necessary. If you are an early stage company that's fully distributed, I'd pick this cadence to start. I think you could probably pull this off without many issues until you hit 25+ employees.

As the company grows, you will start feeling a gravitational towards meeting up on an annual basis for the following reasons:

1. Cost: It's not cheap to pay for travel, Airbnbs/hotels, etc, especially if your team is globally distributed.
2. Planning Headaches: Once again, it will become logistically challenging to make this happen without hiring someone who focuses exclusively on planning these events.

Location?

This is highly dependent on your company and what people prefer. Here's a few obvious rules of thumb:

1. Finding a centralized location can save a bit on the cost
2. It might be fun to try a different place every time - just know that it creates a new logistical challenge and this variance may backfire (or work out in your favor if the location is epic)
3. Everyone will have an opinion. If you do solicit feedback, scope it down to 2-3 potential locations to keep discussion a bit more constrained.

Cost?

It is impossible for me to give you a sense of cost because there's so many variables at play. What I will mention is that in any scenario, this is something you need to watch and guide like any other expense.

The cost will follow a normal distribution curve if you don't create guardrails for people to follow. Some people are super frugal and will book the cheapest flight possible. Others won't pay any attention to the cost and will book a flight at the last possible minute. 

I've included a graph below to explain.

If you are trying to keep the cost from getting out of control, you need to write down your expectations, share them with the team, and hold people accountable if they don't follow them.

For example, at a previous company, they created a comprehensive guide for the company meetup outlining their expectations when booking flights and travel. I thought this was an awesome approach. If your expectations aren't documented & reinforced, you are asking for issues.

If you are the founder of a smaller company, you could just ask the employees to book travel directly with you, but wouldn't recommend it, especially long-term. You have more important things to do.

P.S. - many co-located companies have company retreats and sales kickoffs, so when thinking about cost, I would encourage you to not think about this as an event that only remote teams do. Co-located companies still do stuff like this, so this isn't a purely remote expense, despite what some might tell you.

What you need to know about the offsite

As I mentioned earlier in the post, the most valuable part of meeting up in person is the time to rapidly charge the trust battery with the people you work with. Therefore, this goal should be the primary focus of the company onsite and should influence the activities and structure of events. With that being said, let's dive into the specifics of the offsite:

1.) Chunk the activities together and consider the order

Similar to a typical day at work, chunking activities by some high-level category helps streamline things. If you are planning this meetup, you should consider a breakdown like the following:

1. Day 1: [insert area of focus]
2. Day 2: [insert another area of focus]

There needs to be a purpose and a goal for each day and this should be obvious to everyone attending. For example, I'd strongly recommend a day of work and a day of "fun." If I was organizing a meetup for a smaller company, I'd consider the following outline:

1. Day 1: strategic conversations and and activity to help people relax (dinner?)
2. Day 2: breakout discussion or pairing on projects (more tactical work)
3. Day 3: fun activities, no work

As a leader, consider scoping and guiding the meetup conversation as early as possible to keep things a little constrained, but think about adding an activity where people can build bonds with each other as early as possible. It could be something basic like having dinner together. These are the activities employees will remember anyways!

For example, I arrived a day before the Friday meetup started a few days ago, so I went over to a coworker's house and checked out his backyard and helped him work on his house. I'm a little jealous of his backyard (below).

Next, there will be a gravitational pull to do actual work and that's okay. That's why I'd recommend having a day be dedicated to getting work done or having brainstorming sessions that may be difficult to do remotely behind a screen.

Finally, save a day for fun. This reinforces the high-level goal (charging the trust battery and building stronger bonds) and provides a memorable highlight reel. It may be wise to save this as the last event, simply because it's a great way to finish things up and it's tough to have a ton of fun and then work. This is the reward.

2.) A company meetup shouldn't be an operational crutch

This may be a controversial point, but I don't think an in-person meetup should be a key dependency to running a distributed company. This should be a nice-to-have, not a must-have. Let me explain.

As a business, you need to create repeatable process and way to operate. If your business relies on a company onsite to get work done and convey company strategy, this may be a red flag and indicate that you aren't doing a great job conveying this information on a regular basis.

For example, I worked at a company in the past that would unintentionally start shelving important conversations a couple months before the company meetup happened. I can understand the gravitational pull to do this, but this creates bottlenecks that cannot be solved over the course of a few days. Topics for discussion accumulate quickly.

3.) Document conversations before, during, and after the event

Despite being able to meetup in person, remember the value of writing things down. If people attend in-person sessions and don't take notes, you should expect people to quickly forget what was discussed.

• Send out an agenda before the company meetup with topics, order, and what will be discussed. This is critical if you have multiple events happening at the same time.
• Designate a note-taker for each session. Some people will naturally do this, you should pick them!
• After the meetup ends, send out a recap that can be reviewed by all.

4.) Drinking?

I've heard horror stories about company meetups when it comes to drinking, but have been fortunate to avoid this issue. There are two reasons why I haven't experienced this:

• Good: the founders/CEO exercised constraint when drinking, which provided a role-model for everyone to follow intuitively.
• Better: the company explicitly stated a given policy around expensing drinks. For example, at a previous company you could only have one drink on the company's dime. I thought this was a great idea.

Sure, people still went out and partied (and they are adults so you can't really do anything about that), but there's a major difference between company sanctioned activities and a select group of people exercising free will. This may be controversial (or not), but a bunch of people drinking heavily is asking for issues at work.

This brings me to my next point.

5.) Behavior (especially from leaders) WILL be remembered

A company culture is shaped by behavior, especially behavior at these off-sites. As a remote team, you don't have many data points to observe on a regular basis, which means any behavior will likely "stick" with people.

This means you should be on your best behavior and be intentional about how you act. Put differently, how you behave at a meetup has an outsized impact on the company culture you build. Be thoughtful about it, but don't be fake either.

Ben Horowitz has a solid book that dives into this in more detail. If you want to go into more depth, here's my favorite book on culture.

6.) Create a feedback loop

Finally, make sure you implement a feedback loop to continually improve over time. I recommend an anonymous survey to capture what people really think. To start, perhaps consider asking the following questions:

• On a scale of 0-10, how likely are you to recommend the company offsite?
• What is the reason for your choice? (open-ended)

Parting Thoughts

I hope this guide provides a helpful framework for thinking about your remote team meetups. I've highlighted the most important takeaways:

• Meetups exist to charge the trust battery and are worth the effort/cost
• Be thoughtful about the structure, cadence, and how you behave
• Implement a feedback loop to figure out what makes sense for your company

If you have any thoughts/feedback, you can ping me on Twitter.