Why (and how) our startup spends $10K on our annual retreat

A behind-the-scenes look at the annual SoapBox retreat

A few weeks ago we finished another company retreat. It was our best one yet.

I’m sad to see it come to an end, but also breathe a sigh of relief — After all, a lot of time goes into 48h of pure company bonding time.

I thought I’d share a bit about why (and how) we do an annual company retreat at SoapBox. Then I decided to dig deeper and do you one better: a retreat tell-all.

The Basics: Why, Where, When

Why we do it

We want to be the kind of company that does really awesome retreats.

What spurred the first one? We just had an influx of new employees and some pretty intense goals to hit. We wanted to ramp up our new team as quickly as possible. Fast-track them through forming, storming, norming and performing so that we’d all just be one team. It wouldn’t be new employees and old employees — just one team.

Where we go

Picking the locations is always the first piece of the puzzle, arguably the most important part. SoapBox is located in Toronto, so we have some options.

But not really, because Algonquin Provincial Park is one of the coolest places in the world, and it’s only a three-hour drive away.

The first time we did the retreat, Algonquin wasn’t an automatic “yes” from the team.

People thought three hours was too far. People thought it’d be too dirty, too isolated, or too hot. However, we agreed that there is something to changing environments, getting people out of their elements, and creating opportunities to bond over shared experiences. And, psychologically, it seems to make them more receptive to new thinking and new ideas.

Algonquin is amazing. I love the landscape, the environment. And a lot of people on our team would otherwise never go and see it and experience it. They’ve never gone camping or canoeing.

So, that was an easy battle for me.

Here are a few tips on location:

• Go someplace novel. Create memories with the environment, smell, etc.
• Change up the setting within the retreat a few times. Do activities, lunch, work, etc. in different spots. Create natural variance.
• Planning to be outside? What are your rain plans? Will you just power through? What about lightning? Make sure you can all fit inside somewhere.
• Make sure the venue can handle food and dietary restrictions on their own. There will be times where everyone is starving. Make sure food can magically appear.

When we go

In terms of choosing a date, we keep it simple: early in the summer, we send a Google form with a couple to choose from and let the team vote.

We get at least 80% buy-in for one date before we move forward with it.

My tips for choosing a date:

• End of a week. Weekends are sacred for family time and people might need a weekend to recover (If you are planning one as physically intense as ours). Look out for holidays and long weekends.
• Set a minimum attendance goal or else you cancel/reschedule. 80% should be the minimum. Communicate that upfront.
• Don’t have accurate dietary restriction and/or emergency contact information? Get that at the same time.

Anatomy of a SoapBox Retreat

The basic premise is the same: we break into teams and compete to “win” points in order to “win” the retreat… and by points, I mean Ritual points.

Here’s a rough idea of what we do every year:

1. Decide on a Theme

What do you want your team to come back feeling or thinking? Unified? Charged up? Excited? Thinking Bigger? You pick. Everything you do should be connected to that.

This year we focused in on “Growth.”

2. Pre-Retreat (and some mind games)

This is the element of the retreat that gets the puzzlers and riddlers really excited.

A few weeks before the retreat, once we get the dates sorted out, the GameMaster takes over.

He… or she… Let’s go with They. They might randomly take over the screen during an all-hands. They might send out an email here or there. They orchestrate riddles and challenges to solve in the office that get everyone to find their team, and earn points in the process.

The riddles can start out small and easy, and are often solved individually.

Then they get harder. Sometimes I’m surprised they get solved at all. Usually they do by some folks working together.

That’s when the team piece kicks in. Eventually people discover their teams and they need to solve the puzzles together.

One year, there were shirts hidden all over the office. This year, the TV screens in each meeting room showed hints about who was on what team. Either way just find your team and prove to the GameMaster you figured it out.

But there’s one super-secret element to the GameMaster: what I call escalation of commitment.

Super-Secret Tip Time (SoapBoxers please don’t read)

Getting someone to go to the middle of a Provincial Park with a bunch of people they barely know — that’s a big ask. Add on overnight? Like, OK we now need to confirm plans with S.O.’s. We might need to rearrange day-care pick up. We’ll miss story time and bedtime. It’s easy for a child-free 20-something founder to not value that. It’s hard for a mom/dad.

Now… Getting someone to open an email on a random Tuesday? EASY.

Talk to a couple people about a riddle? Pretty much anyone can do that. Simple.

This is where the employees influence each other psychologically: With those little riddles, all of a sudden you’ve displayed to your team that you’re participating — and by doing so, and you’re less likely to bail.

It’s harder to just anonymously disappear. You’ve already subtly committed to your team. You won’t want to let them down.

Plus, your team might be in second place by now.

GameMaster Pro Tips?

• Read Ready Player One.
• Push yourself to be hard with the riddles. People are GOOD at riddles.
• Incorporate values, office, Google drive files, and other things people should know. Like… literally…are you sick of people asking you a question about something that’s documented in Google drive? Make that the answer to a riddle. They will have to find it, and you can’t help them.

3. The Bus Ride

Forget carpooling. Forget a coach bus: we take a classic yellow school bus up to a kids camp.

We get everyone to the office at the crack of dawn, give them coffee and donuts, and put them on a bus for three hours.

And what I don’t think a lot of people realize is how the bus is a big part of the retreat. But think about it: you’re on a bus, you’ve got all your gear — it’s like you’re back at summer camp, right? You’re going to start getting excited.

This is the first of a couple postcard moments you want to create: yellow school bus in the middle of downtown, good coffee waiting for the team, breakfast snacks and stressing about the last person to arrive (or else we will leave, no joke).

Things to think about:

• Let the bus ride be natural. You could try and make it productive…but let people talk and enjoy themselves. Don’t think that will happen naturally? keep reading…
• Pitstop every 1–1.5 hrs. Especially if you have coffee on board. Honestly, some people would prefer every 30 minutes. Let people know when the pit stop is and let them act like adults.
• Announce when you’re going out of cell service (p.s. Pick a location that has that “feature”) so they can send some final texts.

4. Lunch

People forget about it, but one of the best ways to bond with people is to break bread. So much so, that there’s a phrase for it.

Here is another opportunity for a postcard moment — get off the bus and a delicious meal is ready for you.

Food is a key moment. Don’t forget about it. There is no time when the team is quieter than when they are hungry and eating. This is the chance to remind them of the plan, the goals, and what they need to do and when they need to meet again.

We use the first meal to run through the rules and basic information for the “eco-challenge.”

5. The Eco-Challenge

The first activity we do when we arrive is the eco-challenge.

It’s what people want to do first too — no one wants to hop off a bus in the gorgeous wilderness and go into a room to do trust falls. Don’t fight what’s natural. Embrace it and plan around it.

People want to explore. Let them explore and have fun, first.

This part of the retreat is mostly planned out by the company we work with in Algonquin. It’s essentially a scavenger hunt: this year, teams got into canoes with a map and a punch card. They had to canoe over an entire lake, hit up a few key checkpoints and complete a challenge activity to get a stamp on their race card. There is also a time constraint, so you have to be strategic with your time doing all the mandatory checkpoints and as many elective ones as possible before racing back.

Our eco-challenge is ~3–4 hours. Yeah. It’s insane. But it’s not CRAZY.

The checkpoints serve a couple purposes: ensure the teams know the time and how to get back; make sure everyone is safe; keep them hydrated with water or give them an opportunity to enjoy the canoe ride with a few beers.

The race is for points. Come back too late and you’re disqualified. Hit extra checkpoints and we’ll knock 20 mins off your time.

This is the physical part of the retreat. It lets certain team members shine. In total, it’s worth the same points as the riddles.

Tips for an amazing race-style event:

• Canoes force people to be together. Take advantage of who’s is in whose boat. More on this later…
• Frequent stops with a challenge that everyone has to be at…but only one person needs to do.
• Ideally, more people per canoe than paddles…it lets people rest.
• Spend some time making sure people know how to steer a canoe.
• Canoes are just our tool for this, I’m sure golf carts or tandem bikes would also serve the same purpose.
• Try taking people’s phones away to “keep them safe” if you are still in an area with cell reception.

6. The Postcard Moment (swim-sauna time)

This is it. This is the moment.

The teams get back. The weather is great. There just happens to be an hour or two before dinner is ready. There’s a little free time for fun.

They walk up to the dock, the lake and view is perfect, and between the two Adirondack chairs are couple of coolers full of ice with some cold drinks in it.

50 feet out is a floating sauna with the fire going. Not a swimmer? We’ll canoe you over.

This is the natural “unplanned” time you have to plan for. We’re all ready to relax a bit. We all have stories of what our teams did and who did something great or silly or heroic. Everyone has a shared experience but they didn’t witness what every team did. Natural bonding.

7. Dinner + Campfire + Drinks

At this point, your team will be hungry. Feed them.

Dinner will be last time you get to remind them about tomorrow’s activities. You should do that. What time are we meeting at the campfire? What time should people wake up tomorrow?

Some people might go to bed early, some people might stay up around the fire, some may go down to the dock and look at the starlight night sky.

8. The Breakfast Challenge

The morning of day two always starts with a cooking challenge. There’s two purposes for this challenge.

1. Between the riddles, the canoeing and this cooking challenge, we find it gives everyone something they can contribute to on the team.
2. It makes sure everyone gets up early. It’s a decent control measure for a late night around the campfire.

Here’s what we do:

1. Each team gets a different kitchen, ranging from a fully-equipped awesome space to one that’s basically an outdoor kitchen with a hotplate. First full team to arrive gets their choice of kitchen. The last team to arrive usually gets the worst kitchen.
2. Each team gets a barrel of essentials, and then can pick one item from five categories (like protein, starch, fruits, etc.).
3. Each team pitches their breakfast to the judge, and then we all eat while the judging occurs. Points are awarded for taste, presentation and pitch.

9. The “Work” Activity

So far, we’ve done a lot of “fun” and not a lot of “work.” A big part of that is to build trust and form bonds between the teams. The trust building that happens from the”fun” activities helps make the working session more productive by increasing the psychological safety of each person so even the more shy employees feel comfortable and engaged in the activity.

The activity embodies our theme.

This year’s theme was Growth. So we had an aggressive goal setting activity:

1. Teams drew a Time magazine cover featuring SoapBox in 2 years, as “Business of the year.” On the cover, each team had to include three headlines of the amazing things we did to get there.
2. Pitch the cover to the team. The more hype and energy the better.
3. Vote on whose cover was the best.
4. Now, go back with your team and describe company-wide goals for 12 months from now. What do we have to do to be halfway to our Time magazine cover?
5. Vote again.
6. Final stage: What are our OKRs for next quarter? What do we have to do in the next 3 months to be on the right track?

The key was to make each round fast. Our longest one was 10 minutes. People needed to quickly blurt out what they wanted.

Secretly I was getting the team to help me do my own job.

Super-Secret Tip Time (SoapBoxers please don’t read)

It’s not like I didn’t know what was likely to be on the cover of the magazines. It’s the same stuff we’ve been talking about for months — maybe years. But this activity gets everyone’s buy-in. We’re saying, “You think we should do it, we think we should do it, this is our company, so let’s do it now.”

Follow-through is key. What comes out of this retreat session must make it’s way into the day-to-day experiences of the team. For example, our Q4 OKRs will need to include elements of what the team discussed, or we will lose trust and engagement from the team. They would say “Why’d we even do that work to begin with?!”

Which actually is what you want from your team.

10. Lunch and the drive home

This is it. Tell people to pack up, clean up, and meet for lunch. Again, this is your chance to communicate, so do so:

• Announce the winners of the activities and tally up the points.
• Give out extra points for people who displayed company values while participating.
• Say thank you to the team.
• Say thank you to the people who helped you organize.
• Say thank you to the venue staff.

Then, we take out that year’s retreat swag and pose for a photo. Remember to bring extra swag for the venue staff!

Finally hop on the bus and go back. At the point you’re free. People will either be chatting or sleeping on the ride home.

Ride home tip? Not everyone lives near the office, plan one or two other drop off points for people to get home faster. They’ll really appreciate it.

Swag

Every startup needs swag. We wanted special ones just for our team that they genuinely love to wear. The retreat shirts are no exception. Everyone has their shirts from the years they’ve been to the retreat, so it’s kind of like a badge of honour to wear them to work.

This year, we did coloured t-shirts. They had a real retro feel, inspired by Wet Hot American Summer. People liked them, and it was cool to see the different team colours sprinkled across the lake.

(We forgot to take a photo on the retreat this year, so we faked it 🤣)

Budgeting and Money

I feel like this is what people really want to know about. This is also why most startups wont do a retreat at all.

We were a bootstrapped company when we decided to do our first retreat. We were conscious of the costs and tried to make it as cheap as possible. Obviously, price scales with each person, but years into running retreats, we’ve been able to keep the budget very cost effective.

Here’s what we spent this year:

• Facility: $8,175 (Included the eco-challenge, two lunches, one dinner, sleeping, and a bunch of little things)
• Bus: $1348 (Included return trip, plus a hotel for the driver off-site)
• Beer: $259
• Snacks and Drinks: $118
• Shirts: $697
• Other expenses: $83

Total: $10,635 (about $425/person)

(In Canadian, that works out to $13,818 — about $552/person)

If I was reading this a couple years ago, my thought would be, “jeez do we really want to spend this much on that? Do you get value out of it or is it just a waste of time?”

The answer is pretty clear. It is worth it. Every time.

What happens is a retreat just changes the math in your financial model.

There are things companies offer that alter the basic math: Cool office? Benefits? Free Lunch? Retreat? They all cost money. If you do have them, you’re sacrificing spending that money on other things. Like another product designer or additional marketing videos. It’s up to you when and where to spend that money and what’s most valuable to your team.

I’ve learned, as much as our company is systems we can tweak and optimize, the fundamental unit of getting things done comes down to people. You can’t expect employees to be robots, so spending a little bit on people — in the right way — pays off massively: employee motivation, work ethic, cross collaboration, retention, accountability, understanding, and trust. Those are the intangibles that founders/execs assume hold steady when they build financial models…but the truth is, they don’t.

So, if the retreat is 1% more to the business, it means for every 100 employees you can’t hire that 101st one. Or if the retreat brings costs 10% higher, you can hire 10 employees, but you can’t hire the 11th. Would that 11th employee have gotten you further ahead than having everyone at a retreat for two days? That’s how I think about it. And for us, 10k on the retreat is no-brainer.

A Bunch of Other Worries and Things to Consider

What if people aren’t naturally talking?

Have a few back-pocket activities ready to go, specifically for the bus trip, just in case people are not naturally talking. You probably won’t have to use them, but it’s always good to have a contingency plan. This year we had a trivia game prepared.

You’re trying to facilitate natural, serendipitous bonding. And the cool thing is, we’ve never really needed to pull them out. At least not yet 🤞.

New hires at the retreat?

Having a new hire’s first day at the retreat? That’s awesome. I mean, it’s super intimidating — but it has been awesome for the people who did it with us. On a first days at a new job, you’re meeting so many people you don’t even remember anyone’s name. But at the retreat, you get to know everyone. You have two days. And LOTS to talk about. Names get learned. Done.

Booze?

The workplace and alcohol is always a concern. Especially in this kind of setting.

My wife and I go out and buy the drinks and snacks, so I kind of have a sense of how much can/should be consumed. And there’s a sense of who will consume, and who won’t as much. For me, the goal is to make sure there’s enough for everyone but not enough for anyone to be irresponsible.

It would be harder if people brought their own alcohol up. Things could get carried away. If it’s desired, then it’s something you manage on an individual basis. Watch that people don’t get blackout drunk and fall off the dock. That’s a risk. It’s never happened. But something to be mindful of..

What if someone can’t attend?

Two things to think about. First, is there anything you can do to make it so they feel comfortable attending? I offer to send a message home, because I know that can make a difference (a teacher once spent the effort to call my mom so I could go on a school trip). Second, how do you reintegrate those people back into it? It’s tough. Everyone has all those fun stories and there might be little cliques that form and you have to work to those who missed it back into it.

How can we change it year over year?

I think the key thing is to listen to the feedback from your team. I’ve found pointed questions individually to be helpful. And inviting the team to help us plan it, so they can do the same and perhaps get more honest answers: it’s the iceberg of ignorance — my worry that people don’t share full feedback with me.

Maybe the biggest thought as I look forward is how do we keep the tight-knit feeling alive when we’re not all on one bus.

I mean, at 50 or 60, things are going to start to break. There are things you just can’t do in a group of 60. You can’t have 60 people on a bus. You can’t have 60 people around a campfire. Naturally, groups are going to split off and talk.

On Choosing Teams

Getting the teams right is definitely a big part of making the retreat successful. So we balance out the teams (physical, emotional, puzzle solving and cooking skills), but then there are mandatory pairings as well.

Super-Secret Tip Time (SoapBoxers please don’t read)

Mandatory pairings?

Yes, we have a few people who *must* be on each other’s teams. So while balancing the teams we can’t split these two people up.

We’ve done mandatory pairings with myself and people that I know I haven’t been talking to enough. Or we’ll pair someone who has been really quiet with someone to open up to. But also…if people haven’t been getting along, we put them in a canoe and just hope they sort it out.

The #1 Metric I Track for Our Retreats

On the ride home, look back at the seats and count how many people couldn’t stay awake.

That’s a proud moment. I want to hold on to that.

Thanks for reading!Brennan

p.s. If your startup has hired a few employees (or you’re a manager ), you should really check out our product SoapBox now.

Brennan is the CEO & Co-founder of SoapBox, the #1 place to work in Canada. SoapBox, is an app and assistant for managers to have better one-on-ones, team meetings, AMAs, town-halls and more, with their team.

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