Startup Retreats for a Remote Team - Part 2
In Part One I talked about the WHY of our company retreat; the story behind NextChapter’s first retreat, goals for the retreat and getting started with the planning. In Part Two I will discuss the WHAT. 
  • NextChapter team
  • behind the scenes
Published on Sep 01, 2016


Startup Retreats for a Remote Team

Part Two: What do you DO at a Retreat?


In Part One I talked about the WHY of our company retreat; the story behind NextChapter’s first retreat, goals for the retreat and getting started with the planning. In Part Two I will discuss the WHAT. 


After researching several other startups who retreat, like Buffer, Baremetrics, Automattic and Zapier, I had a good idea of what I wanted to accomplish during this time. Having the first retreat in our HQ city was a great idea because the Serbian team members had never been to the United States and we wanted to give them a chance to experience life as if they lived here. With the above goals in mind, I set out to make an agenda everyone could benefit from – a plan that would help us learn and grow together and on our own. Here is a sample itinerary from our retreat.


Day 1:  Sprint Planning Meeting & StrengthsFinder 2.0 Project


Day 2: Team Volunteer Event


Day 3: NextChapter Team Day!


Day 4: Photoshoot & Video Production & Team Dinner



We also had a full schedule of non-work-related activities that consisted of the following:


•    Startup Events (Wakeup Startup)

•    Columbus Blue Jackets Hockey Game

•    Columbus Crew Soccer Match

•    Hot Chicken Takeover Lunch

•    Wine Tasting and Farewell Dinner

•    Cookout at the CEO’s house

•    Of course: Pizza Parties!

•    Spinning Classes (because: the above)




We are excited for the next retreat to be in a city with warmer climate so we can spend more time outdoors doing things like hiking and canoeing. Even though it was February in Ohio, we did have a few unseasonably warm days so we had a chance to walk around the city, attend a few outdoor sporting events and cookout in my backyard.


What is Team Day?


NextChapter Team Day was the whole reason for the retreat. We met bright and early in the large glass conference room with breakfast and mimosas to kick-off a full day of business, brainstorming and bonding. Everyone received a NextChapter swag bag on their chairs which included a branded Moleskine, track jacket, t-shirt, stickers, a copy of Hooked, a copy of StrengthsFinder 2.0 and a Team Day Packet. The packet covered everything we would be going over during Team Day including some of the history of NextChapter: original sketches of the application, the first mind map and a timeline of events in the company.


The day was broken down into these categories


1.     History of NextChapter

We started with the history of NextChapter. I shared the timeline of events from inception to our first office, first paying customer and each new hire. It was awesome to see where everyone fell into the timeline of the company and for each person to know the back story of how the business came to be.


2.     Purpose & Philanthropy

One thing many people don’t know about NextChapter is our dedication to integrated philanthropy. I took time to explain why we Pledge 1% and what that means as a company. A few talking points with the Pledge 1% model consisted of​

•    1% Equity – Which organizations align with our purpose?

•    1% Time – VTO Policy (Volunteer Time Off)

•    1% Product – How far do we take the free filings for attorneys providing pro bono services?


3.     Flash Talks

For this exercise, we each had five minutes to talk about any topic of our choice. It was a fun time to give everyone else the reins and let them teach the team something they love. Here are the topics we covered:

•    Buying a Dog. Yes, or no?

•    Perfecting Posture

•    All About Adoption

•    Barre3 Demonstration

•    Artificial Intelligence & Robotics

•    How to Tango

•    Benefits of Stretching


4.     Future of NextChapter

This was the most exciting part of our day – planning the product roadmap and discussing the next chapter for the business.


A stack of 20 bright colored post-its were thrown in the center of the table followed by a pack of markers and grade-school stickers: smileys and stars. I stood up in front of everyone and began to explain what looked like a childhood game.


Let’s build everything we’ve ever wanted and needed in NextChapter! I’m going to turn on some music and give you all a chance to write down every idea or feature you can think of. Put only one idea on each Post-It note and then go up and stick it on the wall. Don’t worry about adding one that someone else has already put up there. Just write as fast as you can to include every feature you can think of.


And GO!



Justin Timberlake starts playing loudly through the conference room as the team hustles to jot down the future of the product. Green, orange, pink and blue stickies are placed all over the wall in no real order, like a brainstorming puzzle. Fifteen minutes later, we stopped making feature requests and all took turns explaining our features to the rest of the team, trying to win everyone over. After going through every idea, the next set of instructions were explained.


Now that we all know what these features are, it’s time we figure out what is a WANT and what is a NEED. Pass around the smiley and star stickers and choose a color that will be all yours. Take 5 minutes to scan every feature and mark the 5 you think are most important with a star and the 5 you think would be most fun with a smiley.



After we all placed our stickers on the notes and sat down, we were left with a giant real-life Trello board. The project taught us a lot about prioritizing our upcoming tasks and there were a few interesting things to note:


1.    Everyone had the same understanding of the most important features.

2.    What the programmers thought would be a fun task, was not the same idea of fun for non-programmers.

3.    Building a mobile app or a watch app for such a complex web app isn’t a good use of our time and resources.

4.    We are much further ahead in the production than we all thought.



5.     Business of NextChapter

The final part of Team Day was all about the business. I created a Metrics & Goals sheet for everyone and added it to the Team Day Packet.


________ Active Customers

________ Monthly Customers

________ Enterprise Customers

________ Single Downloads / Filings

________ Growth Rate

________ Monthly Churn

________ Average Order Value

________ LTV (Lifetime Value of Customer)

________ CAC (Cost to Acquire Customer)

________ MRR (Monthly Recurring Revenue)

________ Burn Rate

________ Email Open Rate


I included sections for 6 month goals, 9 month goals and 12 month goals.


________ Active Customers

________ Monthly Customers

________ Enterprise Customers

________ Single Downloads / Filings

________________________ (Feature 1)

________________________ (Feature 2)

________________________ (Feature 3)


Together, we filled out the current metrics and had a discussion on our upcoming goals. The team was much more interested in this project than I expected, thus the project took longer and we didn’t have a lot of time for the other exercises. I did, however, have a chance to briefly go over growth potential, upcoming conferences, partnerships and marketing approach.


By the end of the day, we were all exhausted and excited at the same time. We talked a little about the next retreat: where we wanted to go, when would be the best time of year, how long it should be, how often we should retreat. We came up with a few ideas that involved tropical locations and somehow, even Amsterdam got thrown into the mix.


Team Day was such a big part of the retreat, but we also had many other activities that made us grow personally and together that I will cover in Part Three.