Startup Off-sites - Why They Matter And How I Run Them

The first company I built didn’t have a cohesive culture.

We had amazing people and those people worked hard, wanted to win, and were passionate about beating our competitor…but we didn’t have a culture. That was my fault.

Everyone was there for a different reason and I didn’t know how to bring them together under one purpose. We had two co-founders with differing philosophies on just about everything. We had a Board and investors who didn’t like each other. We had Sr. execs from different planets who had different beliefs on how to shape a company.

In the end we had a group of people spread across two offices with varying levels of interest in the core customer problem we were solving. It was a mess.

There I was, a sub 30 year-old trying to pretend that I had any idea about what I was doing. I had never had another job before, let alone experience in creating a culture.

Fast forward and my second company has been different from the beginning. My own maturity has a lot to do with that, but like any new relationship you learn from the last one. I’m clearer about what I believe in and what I’m looking for, which makes culture building easier.

In company #2 you fix a lot of the cultural basics that were broken in your first company…communication, cadence, hiring, team process, etc. You do a better job of selecting people who share your passion for the same problem. And you are more consistent in your approach, which everyone appreciates.

Even with those improvements I never would have guessed that the single most important cultural ritual that we would develop would be our Off-sites. We’ve taken 17 of them over the first five years at Moment and they have changed everything.

What I’ve come to realize is that off-sites are serious. They aren’t bro time or hang out time. They aren’t random and they aren’t treated with…oh I should do one of those.

Ours are a week long and we hold them three times a year. That means we ask people to be away from their families for three weeks a year. Anyone with young kids they understand just how serious this is.

Therefore if you are going to include off-sites in your culture make them matter. Realize this is your chance to develop the team, fix issues, and get everyone on the same page. They are a big deal and if done right they will unlock a group of people to deliver the best work of their lives.

Everyone has their own structure, this is mine and it has scaled up to 40 people. I’m not sure how it’s going to scale to 100 people where frequency becomes a lot more expensive.

Set Your Offsite Cadence

Before you create off-sites it’s important to first set your company cadence. Off-sites are not random gatherings. Instead they should be timed based on the cadence by which you set goals.

We run Moment on trimesters. Therefore we have an offsite every four months to end the previous trimester and to start the next one. This allows us to dive deep into our recent performance, work on our team dynamics, and set new goals to sprint again.

A side note, but I found that business quarters are too fast. By the time you set goals you only have 10 weeks left to finish them. Having four month chunks gives the team more time to deliver meaningful work. It also better accounts for vacations and personal issues that arise during a trimester.

What Off-sites Are About

You should set a clear purpose for what your off-sites are about.

Our off-sites are about surviving together. They take us back to the basics in life with traveling, cooking, eating, exploring, talking, and connecting. Accomplishing these feats brings us closer together. It forces us to work as one in ways you just can’t accomplish during work hours.

All of our off-sites have these same elements…

  • Travel – we started by caravanning to spots within two hours of Seattle and over time we’ve expanded that circle to the broader NW.

  • One House – staying under one, shared roof is important. We started with camping and over time rented larger and larger homes. We’ve always tried to balance comfort with uncomfortable. Again it comes back to surviving together.

  • Team Made Meals – we make our own food and clean our own dishes. It’s basic, but conversation happens in the kitchen that you’ll never get out of people any other way. What’s beautiful about shared meals is they require empathy. Not only do you have to consider everyone’s allergies, but you have to clean the mess someone else made.

  • Adventure – accomplishing feats matters. It puts people outside of their comfort zone, but over the years we have seen people accomplish hiking feats they never thought they could do. These adventures don’t have to be expensive. Walking on your own two feet enables conversation. These adventures often become the stories people remember.

  • Team Sessions – we deliberately work on the team. There is an agenda with pre-planned team sessions. I keep some of the session cryptic as surprise gets people to focus on the problem at hand. Most importantly this your chance to enable important conversation about the team and how it can run better. It will take practice but over time the team will begin to open up to one another.

Off-site Agendas

To get more granular about the week here is the agenda structure we use. It has stayed consistent over the years.


Before you go, I give the team pre-read. It’s my job to give them context to where the company is today and where it needs to be in the future. The team needs this in order to set relevant goals. In the pre-read I try to include…

  • Table of contents with how long to spend on each section.
  • Review last trimester’s goals, to get them thinking about their own performance.
  • Business recap for the last trimester, teaches them how to think about our business.
  • Remind them about the bigger vision of where we are going.
  • Remind them to re-read our annual plan.
  • Provide context to what matters in the up coming trimester

In general I want most of their time spent thinking about the future and what goals we need to set to get there.

Day 1

In the first day I want to get the group connected talking. In order to go deeper the rest of the week I need to get the broken shit on the table. This is the chance for people to both celebrate and vent.

  • Arrive by 4pm.
  • Session 1: team(s) review their last trimester goals. They go goal by goal, scoring each cool between 0-1 based on how much they accomplished. They then list out why they did or didn’t hit the goal.
  • Session 2: company recap. Each team shares their score and the trends behind why they did or didn’t hit them. We also go around the room and give individual props. This is really important.
  • Session 3: if there is time I have teams break down what is broken. It’s their chance to vent and get stuff on the table they are frustrated about that we need to fix. I write these down and I figure out how / when to work on them during the week.
  • Dinner: this is the first chance we get to connect as people instead of co-workers.

Day 2

The second day is about exploring and thinking big. Depending on the time of year we either get out first thing for a half day adventure or we run some team sessions and explore in the afternoon. Looking at our winter off-sites the day looks like…

  • Breakfast: We have found cold, self serve breakfasts work the best.
  • Adventure: During the winter we try to be out early to maximize the light. We’ve done everything from snowshoeing to snow bike riding to skiing / snowboarding. We make sure each adventure accomplishes something together.
  • Session 3: The first session is always about thinking big. Generally I’ll run a session about how we grow 3-4x in revenue or team size. Below are notes on how to run a growth session but this lets the team think about scale without constraint.
  • Break
  • Session 4: This is a follow on to session 3 where we go more tactical to idea generation. These can be ideas to hit the growth we talk about in the previous session or can be tactical to our next 12 months. These are always in cross functional teams to get new relationships started. It also forces people to learn how to present their results in front of the whole company.
  • Dinner: Deliciousness.

Day 3

The third day we get tactical to what we need to culturally fix. This is where I bring in issues from Day 1 or issues I know we need to work on. The structure of the day is similar to Day 2, but instead we hit a series of short culture related topics. The key is keeping the energy high during the sessions.

  • Breakfast
  • Adventure: We do a second adventure, again with some form of accomplishment.
  • Session 5: In 60 minutes we’ll cover the most important cultural topic. That can be anything from compensation to communication to process, etc. It’s always about…how could we do "blah"? Or how could we fix "blah"? Again done in cross functional teams.
  • Session 6: This is the second most important topic.
  • Session 7: This is the third most important topic.
  • Dinner: Followed by drinks and hanging out.

This topical patter continues until we’ve spent about four hours together. After that the quality of the sessions begin to drop off.

Day 4

This is the hardest day. It takes a lot of mental concentration to crank out four months of goals and tactical objectives to hit these goals. Over time this day has gotten easier as team leads have done pre-offsite planning.

  • Breakfast
  • Session 8: I bring the whole company together and we go over the pre-read. This is my chance to make sure everyone understands where we’re going and why. We move from the big picture to the annual plan to the trimester plan.
  • Session 9: Teams split apart and start setting goals. Generally teams end up with 3-7 goals depending on their scale and maturity. Each goal is measurable as an end result or measurable in progress (i.e. development stage of a new product).
  • Lunch: Often self-serve the teams eat and keep cranking.
  • Session 10: Once goals are set they work through the tactics to hit their goals. Then they map out what they are going to work on and in what order. This is tedious work.
  • Snacks: everyone needs a break by the afternoon.
  • Session 11: We bring the whole company together to go over goals by team and review these against a company calendar. Our calendar is very basic, but includes any cross team initiatives we all need to know about. This session has gotten better over time as the teams have improved at saying what they need from other teams.
  • Closing: This completes our off-site. All sitting together this is a chance to congratulate the group on an amazing week. It’s also a chance to get feedback on the week while it’s fresh.
  • Dinner + Relax: The rest of the night is just about hanging out together. We share a last meal, connect, and sometimes a dance party breaks out.

Day 5

We pack up and go home. Everyone cleans the house together and we caravan it back to the airport or the Seattle studio.


After every off-site I document it on a private web page. It becomes our company history and provides reading context for new teammates. Understanding where a team came from is really important to understanding where they want to go.

  • Collect photos from everyone on the team.
  • Write a day by day recap with notes form every session.
  • Drop in photos as they happened so the reader gets a sense of what it was like.
  • Post it to a private page for your team that links to a master Off-sites website.
  • Make this page part of pre-read before next off-sites so people can remember what we did last time.

Immediately Fix What’s Broken

After an off-site it’s important to immediately fix the broken items you. Any simple ideas or changes to process I try to fix before people start work on Monday. That way people can see a direct impact to the feedback they provided.

This builds trust and carries your momentum from the off-site into the trimester.

If you go into the next offsite with the same foundational issues then you’re doing something wrong.

Off-site Exercises

I wanted to break out a few exercises you can use with your teams.

Session – Review The Past

We have done this a few ways over the years. As the group has gotten larger we’ve moved from doing this company wide to doing this by teams and then recapping with the whole company.

Our general process is…

  • Review the goals. Here we go goal by goal. We score each goal from 0-1 depending on how much of it accomplished. With each goal we list a few why’s. This helps us learn how to set better goals.

  • Highs and Lows: Each person goes around and shares their personal highs and lose from the last four months. We now do this within teams but we used to do this company wide. It was very powerful as it pushed people to be open with others.

  • Props: Public acknowledgement matters. We have each person go around the room and give props to their teammates. You can see how body language changes immediately when this happens.

What’s important during this session is you take notes. You are looking for threads for things you need to fix. Working through these issues is very, very important.

Session – Think Big

I’ll write a post about this but on Day 2 I run a series of sessions that teach the team how to think big. People aren’t taught how to scale teams or revenue and so these exercises give the team a chance to learn how. I’ve run this exercise in terms of revenue and/or team growth.

You post a questions…How would we get to $X in revenue?

You have them for cross functional teams (4-7 people) and they get 20 minutes to do this exercise. After 20 minutes they will come back and present their brainstorm. Generally what you get are a list of tactics.

This is your chance to teach. First you let them know you only gave them 20 minutes on purpose which means there was no way to get into tactics. You were looking for the "how" which means they have to start at the highest level and then break down your path into smaller details…

  • Start with the most basic unit in your business. In ours, it’s customers.
  • Map out how many you need to get to answer the $X question.
  • Once you know how many customers break down what percent comes from new versus repeat.
  • Once you know the mix you need a framework for how you get there.

….a very efficient group can maybe get this far in 20 minutes.

You then send them back to do the exercise again this time having them come back with a framework for how. They return with something that’s closer on number of customers but the how goes back into tactics versus outlining a strategic framework for how.

You then would show them that in order to get growth you either need to go wide (more offerings to the same customer), go deeper (more customers with the same offering), or expand distribution. You send them back to better outline a framework for "how" they are going to get $X from new and $Y from existing customers.

After 20 minutes they are closer. They have made some assumptions about what would work in order to reach those customers.

Depending on how much time you have, you continue to repeat this process until they have a rough plan of how to get to $X in revenue.

In doing this kind of exercise you quickly realize that you need to understand the process in order to teach it. Secondarily you realize this kind of strategic thinking is not taught.

You can run this type of exercise at every off-site, you just increase the revenue scale of the initial question to make it harder.

Session – Role Playing

These sessions are my favorite. I’ve run different role playing scenarios to get the teams thinking about topics they would never expect. Generally I’m creating scenarios so they can see elements of a shitty culture. This helps them clarify what they want in our culture.

An example would be…I wanted to teach people how to quit. No one teaches this and whenever someone quits it’s terribly done, which leaves the existing team in a bad spot. Therefore while doing a team hike we had a 30 minute break to run this session.

I paired everyone up and gave them one of two cards.

Card one said you had to quit. Each card was a slightly different version of quitting. I had the passive aggressive quitter, the angry quitter, the I don’t give a shit quitter, the over apologetic quitter, etc.

Card two said you had to fire the person. I again came up with different versions of firing someone from passive aggressive to direct to excuse filled.

It doesn’t take too long for people to catch on to what is going on. They can somewhat overhear other teams, which makes it funnier. This ran for about 20 minutes and then I brought the whole group together and let them share what they liked and didn’t like about the person they interacted with.

In the end I was able to teach that what matters in the business world is your legacy. Therefore if you are quitting, here is how you do it.

If you get creative you can come up with all kinds of role playing scenarios like this. They are fun and give you a chance to teach something often missed in startups.