How to Organize a Startup Retreat: 10 Things We Learned at V7

V7's team of 40 unites twice a year in a company-wide retreat. For our third retreat, I'd like to share our learning from both an organizational perspective, and the outcomes you can expect.
Read time
December 22, 2021
The V7 team waving in a group photo at the Winter 2021 retreat

V7 is a a hybrid company, with our engineering and product team being distributed across Europe spanning Portugal to Georgia, and our sales team in London. Our team of 40 unites twice a year in a company-wide retreat: 5 days in the summer, and 3 days in December. This winter has been our third retreat, and I'd like to share our learning from both an organizational perspective, and the outcomes you can expect.

Retreats can be expensive and time-consuming to organize, but if you play things right they'll pay themselves off in multiples. I'll list out a few of the things that worked out well for us, and some mistakes to avoid.

1. Plan around your end-goal as a startup.

Some company retreats are work-holidays, some are closer to summits. Our goal was to focus on our colleague's personal development, and comfort around their peers, in a place that didn't feel like work and they'd be nostalgic about one day.

Our goals were the following:

  1. Get everyone to be sincere and comfortable with their colleagues, some of which they'll only met twice a year in person.
  2. Learn to pitch the startup, our messaging, and find pride in what we do (great for the upcoming Christmas dinner with parents)
  3. Genuinely look forward to the next team events as a result of the retreat experience.

The first of the three was our primary objective: Break the communication barriers set up by Zoom and ensure that the next remote call feels like talking to a person you trust and respect, and shared valuable memories with.

Outcomes are hard to measure, other than surveys, but if you follow this short guide results should be tangible from the next day at work. Below are a few considerations we enacted at V7 before you start planning:

Retreats should be mandatory

If you're a distributed company, you are doing a disservice to your new joiners by not giving them a chance to meet their colleagues face to face. Make sure everyone shows up unless they have extenuating circumstances. You've hired ambitious people that are dedicating the prime years of their life to your startup, and its important that they feel connected and inspired by their fellow team-mates.

Plus-ones are a bad idea

This is a time for your team to learn from one another. Inviting spouses would enrich the experience for some, but also double overheads and the chances someone will be disengaged. You need to draw a line on what +1s are allowed to avoid turning a startup retreat into a generic party, and it's not always a fair one to draw. It's best to keep it to FTEs only.

Don't pitch it as a holiday

When on holiday, people expect freedom of movement. You want groups to stay together, engage, and cooperate in workshops. Set the expectation that the retreat is for self-development, but not a vacation. Pick a great venue, good food, some wellness, and fun activities and it will bring your team much more than what a holiday can.

2. Pick a venue with large rooms.

James Hudson overlooking someone's laptop at V7

This winter we stayed at Milton Manor in Dorset. We chose it over a shortlist of 12 venues because of its large dining hall, proximity to Heathrow airport, and 17 bedrooms. We set up a Notion table ranking homes with at least 30 beds for the following traits, ranked by importance:

  1. Distance to London (Hours)
  2. Number of bedrooms
  3. Dining room setup (Can we fit in the same room)
  4. Outdoor amenities (Garden for activities, firepit, hot tub)
  5. Games room and wellness venue

You'll want to be close to hour HQ to reduce flight costs and travel stress. Don't underestimate how stressful it is for your team to book COVID-tests and figure out more than a 3-step journey form their home. We kept it to 2-3: Direct or 1-stop flight + bus trip.

You'll want to maximize bedrooms in the event of heavy snorers (survey for it!), or if someone falls ill (this WILL happen in any group of 20+).

You'll want a large dining room to make short speeches, announcements, and simply to dine inclusively.

Finally, if there's lots of games and amenities, people will find more ways to break the ice over the 3 or 5 nights you're there.

Don't use AirBnB, pick a specialized site for large homes

In the UK we booked through Sykes; if you're in the US try Vrbo. The selection of large homes on dedicated aggregators is much richer and often cheaper. Sykes has discounted prices for longer stays and better support for the inevitable Q&A with the host about internet speeds, laundry, or anything else your team might want to know about in advance.

Below is the annotated birds-eye view of the venue we picked.

Milton Manor birds eye view

3. The schedule must be almost exhausting, and include no "business as usual" work.

The most frequent piece of feedback from our Summer 2021 retreat in Puglia (southern Italy) was that we had large gaps in the schedule, in which people just worked. It's not healthy to see your colleagues working away to hit a deadline while you chill in the pool, so make sure there's no chance people need to choose between "real" work and a retreat activity.There will be exceptions of course: Support and CSM will need to jump on calls, and Sales might need to squeeze a demo, but they should be avoided if possible.

This winter we kept a busy schedule, almost too busy. You'll want something like this, but with 15 minute breaks between workshops:

The calendar schedule for our startup retreat

A busy schedule, with a few parallel worshops, creates fear-of-missing-out (FOMO). FOMO will signal that you're doing something right, and that your team doesn't want to miss what's going on. Keep the schedule too relaxed, and folks walk off to their rooms or split from the group.

We overdid things a little, and should have scheduled 15 minute break between slots to allow some idea-sharing, coffee refills, and relaxation.

Here's a breakdown of the activities in our man stream:

  • Room assignment: Stick a numbered post it on each room door, and assign teammates to each. Prep the allocation beforehand by asking the host for a floor & bed plan of the house.
  • Arrival Drinks & Retrospective: Get the CEO to mention everyone's contributions individually, followed by some cheer, and prep a retrospective presentation of photos and videos of highlights from the past year. Make sure everyone has a drink in their hand and are relaxing prior to icebreakers.
  • Icebreaker Event: V7's Brent Gracey became famous for his "Brent Event" icebreakers, which even developed its own chant. Brent organized a few team activities involving purposefully silly activities that require collaboration and often lead to multiple failrues.
  • DogFood hour: If you're running a startup you know what dogfooding is. Simon Edwardsson, V7's co-founder and CTO split the company in two teams, each simulating our customers. Each cohort had the same objective and needed to sign up to our product from scratch and achieve it in 90 minutes. When your entire team does this in tandem, it will will expose a lot of bugs, front-end issues, and UX annoyances. Ensure there's someone in each team to take notes of any emerging bug.
  • Technical workshops: Get engineers to explain to other engineers how they built things.
  • Headshots: Take great pictures of your employees which they can use on Linkedin, or wherever they wish.
  • ShapeUp: A guided introduction to the ShapeUp project management methodology V7 will be testing in 2022.
  • Recruitment Workshop: Get your team to reach out to the smartest people they know, and tell them to join your team.
  • Messaging: Get people to pitch-practice your startup, as well as the famous "what do you do" question. You'd be surprised how hard this can be for those who never practiced.
  • Christmas Games: We ran some quizzes about company statistics, fun personal facts, and other trivia using Slido.
  • Special Guests: Through some locals, we organized a duck and goose herding game. Teammates would set up obstacle courses for farm ducks and another group would herd them through it, sometimes with the help of trained sheepdogs.
  • Team Interviews: Interview your employees about what it's like to work there. This will come handy for employer branding, and its a good memory to capture.
  • Hackathon and presentations: We had a mini hackathon (Pitch-a-thon technically as nothing got built) in using the ShapeUp framework. Rather than building product features, teams would spec them out over the course of a half day, asking other teams for advice on each.

4. No "real" work should happen.

Anastasia Kaschenko, Niclas Ernst, and David Bielemberg playing icebreaker games

You've hired an ambitious team, and no one wants to feel like the slacker. Your team's time is best spent interacting with one another in collaborative ways. Before you depart, set up banner warnings in your support channels defining reduced working hours, test that your uptime monitoring works smoothly, and get everyone to set out-of-office email replies.

We made the mistake in Summer 2021 of allowing "real work", and people would catch up on email over breakfast. Bonding takes time, and has compounding effects on your team's collaboration. Get them to talk to each other.

If you're setting up icebreakers or games, avoid single-competitor games (like archery) and opt for sillier activities where good communication is the key to victory.

5. Make transport easy, even if it costs more.

V7's team traveling by coach to the retreat

Keep transport to no more than 3 steps: 1 or 2 flights, and one bus ride. Anything past that will be felt by your team as they must self-organize their land transport alongside pandemic-related hurdles with entering a new country.

We opted to let everyone self-book their flights this year, and it was a mistake. Designating one person to book flights alongside each employee will guarantee you a stable headcount weeks in advance. Do this right after you book the venue.

The best mode of transport to your venue will be wheeled. Hire a coach for the day (for us it cost around £700 both ways) and have it depart from the city center (for anyone in the HQ city or arriving earlier) and stop by the airport to pick up the rest.

The bulk of your travel cost will come through delayed bookings, and challenging connections. Luckily we departed from London which is well connected across Europe, however last summer we had a few V7ers take an Odyssey to reach Puglia, arriving exhausted and not looking forward to their return trip. If you're headquartered in a small city, consider booking your retreat closer to a large flight hub.

6. Assign roles and workshop leaders. No more than 90 min stage time.

Simon Edwardsson giving a presentation

1 month prior to the retreat, We assigned the following roles:

Photographer: 1 lead (with a pro camera) + 2 assistants to take phone pics.

Food Coordinator: Set up catering and cleanup

Drinks Coordinator: Purchase alcohol and prepare cocktails

Room Assignment Person: Chose who sleeps where, and who sits where at the table (trust us, it helps!)

Minister of Coffee: Make sure coffee is always available.

Cleanup Crew (x3): Clean up every evening or morning. Ideally the catering will do the bulk of the work.

Laundry Person: This one is only useful for 5-day retreats. Do laundry for the team.

Designated drivers: Non-drinkers who can do grocery runs when needed (hint: if you organize well you shouldn't need store runs).

AV & Connectivity: Someone good with router equipment, AV cables, and ideally who can bring the right hardware.

Workshop Leads: Run a workshop to avoid any of the above responsibilities.

Avoid having your team be in charge of driving and cooking. It can be unnecessarily stressful, and dangerous in unfamiliar roads or kitchens. Rely on the free market for that.

Presenting to your peers is exhausting

Workshops are incredibly useful ways of getting everyone to work on something that doesn't quite fit in your weekly routine. For example, learn to pitch your startup, or have an engineering lead present how part of your backend works.

Make sure you have more workshops than any other activity, however, keep them within these limits:Under 90 minutes: Ideally 60, anything longer than 90 will keep the team hostage.

Max 1 per person: This gives a chance for everyone to present a workshop, and also avoids exhaustion. The founders might want to run two, but its inevitable that one will get more love than the other.

7. Armies run on their stomachs, your team too!

The V7 team having dinner at the Winter 2021 Retreat

No startup is more than three bad meals away from chaos. Get a good caterer!

Find a local business that will come to the house in the morning to prepare breakfast, lunch, and dinner. You may also deliver food from local restaurants. This will cost less but will give you less flexibility with timing (caterers can work around your delays), be less delicious, and most importantly, it won't solve cleanup. This winter, our talent lead Dominic Wright found the excellent Thyme Dining. They set the table, decorations, candles, menu cards, prepared individually portioned plates for 3-course meals, and did all the cleanup. Was it worth the added expense? Definitely.

Not worrying about cleanup is key. After your third 20+ person cleanup you'll notice how hard it can be, and will cause delays into the rest of your schedule. Industrial dishwashers only hold about 10 people's worth of dinnerware, and your team might (with good intentions) be juggling wine glasses on their laptops to carry things back in one trip.

Meals (the whole experience, not just the food) are good morale boosters. If the venue allows, cooking a meal together is an excellent idea. However, consider it a team-building activity rather than a duty, and give a 30 min buffer to dinner time unless you're cooked for large headcounts before, it's a different ballpark.

8. Take Headshots!

Do you have a team member without a profile pic on Slack? Chances are they just don't have good or up to date pictures of themselves. Set up a headshots station and get someone extroverted to make people smile before the camera. V7's Rafal Slota was our lead photographer and took a few posed shots of each participant. People are now using them as profile pictures on Linkedin, Slack, Facebook, and probably a few dating apps.

Headshots aren't just meant for your company's About Us page, they're a genuinely useful gift for your participants which they'll benefit from outside of work too. They only take one hour! Make sure you take a few team shots too. People smile more genuinely when posing with another person, and you'll get some great shots of your various teams.

Another great idea is to hand people props for their headshots, especially if you work with hardware. Some people feel uncomfortable posing alone, but will pose naturally with a prop.

While you're at it, set up a station for team interviews. We purchased a ring light with an integrated phone stand, and plugged a lapel mic into an iPhone. This relatively amateur setup worked quite well and in 2 hours we were able to cycle through everyone by pulling them away from workshops for a few minutes.

9. Bring a Drone

A drone shot of the V7 team

A drone's built-in gimbal is not just a great way to take standing handheld camera shot (far superior to your phone or DSLR), but also a great way to take fun group shots. Invest in one ahead of the retreat, and consider insuring it—You're probably heading somewhere with a lot of trees.

You may also want to use your drone for handheld shots. We took this team video during our summer retreat by holding the drone by hand, and the gimbal does a better job at panning than our arms.

10. Founders: Be Sincere

In-person announcements hit differently. If you have remote colleagues, this is their one chance to hear the good and the bad from you in an out-of-office environment. Focus on the positives, and be energetic, but don't shy away from the challenges ahead. If you hired well, your team is motivated by solving hard problems and will see them as an opportunity for growth. Likewise, you're there to listen to their responses and feedback.

Simon and I use the retreats to paint a broad pictures of things in 10 years (the world you'll build if the startup is wildly successful), and of the next 12 months (the world we can build today). Both need to be exciting, yet both won't resonate immediately with everyone. Listen to why. Take time to explain your personal motivations, host a founder Q&A, and make sure everyone knows the story of how the startup came to be in the first place.

Use your stage time to explain what is hardest for you as founders, and what do you dream the product to become should everyone succeed in their job perfectly. If you paint the challenges, your team will rise to them. That's what they're there to do.

Bonus: Our Packing list and Cost Breakdown

Packing List

  • DJI Mini Drone
  • Ring light
  • Lapel microphones and extension cords
  • HDMI cables and dongles
  • Extension cords and multi-plugs
  • A1 Paper and markers
  • A whiteboard shipped to the venue
  • First-aid kit, and common over-the-counter medications.
  • Speciality liquors and snacks
  • Bluetooth speakers (x3)
  • Amplifier + microphone for presenting
  • Company swag
  • Ethernet cables
  • Extra router
  • Games (Poker, Resistance, Nintendo switches, and other board games)
  • Christmas crackers, glow sticks, and decorations
  • Purchased locally: Firewood and alcohol, s'mores.
  • 120 antigen tests

Cost Breakdown (rounded to the nearest £500)

Costs (In GBP) are for a 3-night retreat for 27 adults

Venue hire: £4,000

Catering & service: £6,000

Travel: £3,000

AV and Photo equipment: £500

Stationery, decorations, and snacks: £500

COVID Tests: £1,000

Total Cost: £15,000 (~$20,000)

The monthly cost for a decent 27-person office in central London for 1 month is around £20,000. That's without meals or travel. What we gained from those 3 days is far more than what 25 "regular" working days in the office could have provided for team cohesion. If you're a remote or hybrid company, or are ready to downscale some of your real-estate costs as your team works from home a few days a week, consider re-investing that in a yearly or bi-yearly retreat!

Automate repetitive tasks with V7's new Gen AI tool
Explore V7 Go

Other news

Ready to get started?
Try our trial or talk to one of our experts.