4 min read

Take your company on a retreat

It’s easy to get bogged down in regular routine. Your team wakes up and deals with the crises of the day.

  • Customer X experienced a bug and needs some help.
  • What’s the status on that feature that’s behind schedule.
  • You need to prep for that meeting in an hour.

On a regular day it’s hard to look more than 3 ft in front of your nose. You set the direction of the company on autopilot. Then everyone starts spinning their wheels in that general direction.

Every so often it’s helpful to take a step back, look at the big picture and get the whole team thinking about the next year, not just the next day.

Inspired by companies like Wildbit, we decided to take a retreat to spend a week and focus on the long term. Here’s the approach we took:

Change your scenery completely


We spend every day in the city. A cabin on a lake in the mountains was a perfect change of scenery for us. No sirens blaring. Lots of peace and quiet and nature.

We rented a house that was comfortably sized for all of us. 4 of us in a house that could hold 10 (with lots of shared rooms). We certainly weren’t crammed in there.

Some of the diversions the house had to keep us occupied:

  • A games room with Ping Pong and Air Hockey
  • A trampoline
  • Canoes and Kayaks on the lake

It was great. While this was meant to be relaxing, it’s not a team vacation exactly.

Set some goals before you go

We had two goals as a team for our trip.

  1. Talk through company strategy around things like hiring, fundraising, product scope, marketing strategy.
  2. Start working on the next release of the Customer.io interface.

And we wanted to make sure we did something outdoors each day and didn’t just spend the days working. My expectation was that we’d do 4 hours of “computer” work each day.

Do lots of fun things as a team

Day trip to Hudson

Went to Hudson to pick Asha up at the train station and grab lunch. Side note: Hudson is a great place… and boy… for $100 more than our 4 desks @ $600 / desk Manhattan we could get a nice building for our office in Hudson.

Grilling outside

We barbecued every night except when we went out to dinner.

John tending the grill

Visiting beautiful places

We bouldered our way up to Kaaterskill Falls, a large 2-tiered waterfall.

Bouldering people

The falls were really impressive once we got there.

Kaaterskill falls

Doing strenuous exercise

We did a half day hike to the top of a small mountain.

Top of the mountain

Where Henry left our mark.

Our logo

(don’t worry it’ll wash off in the next rainfall)

Spend some time on work too

John and henry working

It was great to have the whole team for uninterrupted time. It meant that we could have conversations without someone getting pulled away to do something else. For the bigger questions, we went to the fire.

Discussion time around the fire

Two of the nights we built a fire and had open discussion time outside in the dark while we roasted marshmallows.

Henry (our summer intern) asked us lots of questions on how we started the company.

All the other questions around strategy and aspirations for the company were discussed too.

Were there any bad things with the retreat?

Sure! Some of our customers weren’t as happy as usual with our customer support.


We set up an auto-reply saying that if there was something urgent we’d deal with it. Otherwise we would answer over the weekend.

Overall, the damage was minimal and hopefully short lived for the benefit the retreat brought to the team. We still answered more requests than just the people who said their issue was urgent.

Overall it was a great success

The feedback from everyone was positive. Phrases like “Let’s do this twice a year” were thrown around in the post-retreat buzz. Coming out of the retreat we were more focused, had a clearer direction, and felt closer as a team.

In 5 years time, we’ll all probably look back on this retreat as a fond memory from the early days of the company. I’d encourage you to go make some fond memories of your own.

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