19% of remote workers say that loneliness is their #1 struggle with working remotely according to Buffer and company’s 2019 State of Remote Work report. I can relate.
While there are so many strategic advantages to running a remote team, there are also some parts of working remotely that really suck from a personal standpoint. The biggest one for me: loneliness.
I thrive on the energy of people in person with my teammates. I process so much information through body language, movement, and white boarding. All of these things are much harder online. But the thing that’s hardest of all is missing those brief conversations after a meeting, the impromptu lunch or happy hour, and the in-person brainstorming.
All of these things breed human connection that is hard to replace through the computer.
One of the best ways we’ve found to combat the sense of loneliness and isolation in remote work is through bi-annual team retreats. Retreats have become our best way to connect on a human level, get that boost of energy from being in person, and communicate our vision for where we’re going together. Best of all: we have good old fashioned fun together.
Here’s one of the recap videos to give you a sense of how we spend the time together:
Nathan Barry founded ConvertKit in 2013 and our first team retreat was in August 2016. August 2019 will now be our 7th team retreat. We’ve learned so much in the process that I want to share with you so you can plan your own team retreats or adjust how you’re already hosting them. If you have tips for how we might make ours better, share with me on Twitter.
The Goals of a Well-Run Team Retreat
Before diving right in with the details of how we plan our team retreats, it’s important to take a step back and consider why we host team retreats to begin with. What are the outcomes we want?
For us, we have a few major goals:
- Have fun – retreats are just two weeks out of the year. We have 50 other weeks to power through all of the work to be done. If teammates don’t have fun on retreats, then we’ve failed at planning an effective retreat. Fun doesn’t have a universal definition, so we cater to different personalities and preferences here.
- Encourage meaningful connections – we want everyone on the team to walk away feeling more connecting to their teammates. Ideally each person will have deep, thoughtful conversations and shared experience not only with their immediate team, but also with people from teams across the company.
- Dream about the future – any time we step back from our normal day to day routine is a perfect time to explore possibilities. Our brains go into a different mode when we leave our normal environment, so we want to take advantage of this by imagining what the future of the company might be.
- Make plans and get good work done – this is the last listed priority for a reason. If all we did was accomplish the previous three objectives, we would still consider our retreats a great success. Any work that gets done is gravy. At the same time, we do put intention into making sure we have sessions between teams who work together closely. We also make sure to schedule sessions for teams that may be experiencing conflict at the time so that we can build bridges of understanding, which is easier to do in person.
These four objectives will serve as the structure for the rest of this post. But first, we’ll cover logistics.
The Five Core Objectives for Planning a Great Team Retreat
Objective 1: Get the Logistics Right
While it’s easy to think “logistics will take care of themselves,” they definitely won’t. Getting the logistics wrong can throw everything else off. Our operations team works incredibly hard to make the logistics work. When we do it well, the logistics become invisible to most of the team.
Here are the key logistical questions we ask:
- How frequent?
- How long?
- What time of year?
- Where?
- What kind of lodging?
- How will people get there?
- How do we encourage wellness?
- Sleep, diet, and exercise (chef, plenty of sleep, etc — help people stay well)
Frequency
We decided to have our retreats twice a year. We’ve found that people start craving in-person time with one another after about four months apart. About that time, we already have the details set for the next retreat and we’re able to start building the anticipation towards it. The countdown helps everyone look forward to seeing everyone without despair. We’ve also found that twice a year caters to our budget. It’s not cheap, but the cost is manageable.
Length
For our retreats, we have the majority of the team arrive on Sunday night and leave on Friday morning. That’s five nights away from home, which is a lot, but it also gets everyone home in time to have a full weekend at the end. For teammates coming from three or more time zones away, we allow them to come in as much as 48 hours in advance of the rest of the team to allow for adjustments to jetlag. For teammates within that three time zones who simply want to arrive early, they are welcome to, but it’s also up to them to cover the cost.
Time of Year
We host our retreats in February and August each year. This is flexible, but we’ve found that timing aligns nicely with the rest of our planning calendar for the year. We’re in the middle of our quarters during those times, so we don’t interrupt our normal goal-setting cycle. In February, we typically go to the San Diego area for warm(er) weather so teammates can escape the winter and dry out / get warm for a week. Up to now, we’ve used the August retreat to go up into the mountains of Idaho where it’s a bit cooler and we can still get outside and enjoy nature.
Location
Starting in August 2019, we’re experimenting with new locations. We’ll be going to Pigeon Forge, Tennessee in August 2019, back to San Diego in February 2020, and then to southwest England in August 2020. No matter what, we always look for a location that’s within a couple hours’ drive of a major international airport. With teammates coming in from 39 cities in 8 countries, this is highly important.
Lodging
As the team has grown, it’s become harder and harder to find unique, inviting places to stay. We want to avoid sterile conference and retreat centers, so the process for finding locations has become more and more like detective work with time. In August 2019, we’ll host 48 total teammates at our retreat. In August 2020, we looked for a location that could host more than 60 teammates. Not surprisingly, this is challenging. That’s why we’ll be staying in an estate similar to Downton Abbey when we go to England. If you get the reference, you get the reference.
Travel
Booking travel for our team is a nightmare. I say that so you don’t think you’re going crazy when you tackle this aspect of retreats as your team grows. We give the team basic guidelines: arrive by [date/time], leave after [date/time], ride with [teammates], etc. Rental cars are booked and drivers know who they are ahead of time.
We leave it up to each teammate to book their flights and simply ask them to “spend as if it’s your own money.” If they have doubts about whether travel is too expensive, we have them ask our ops team for advice. We always maintain a principle that if you can book a more convenient flight (gets you there faster, on a better airline, gets you there by the deadline, etc) within 20% of the cheapest option, go ahead and book the better flight.
If I were to start from scratch, I’d probably find a travel partner for this so that we could outsource more of the decision making. This is a shortcut you can take from the beginning that might save you a lot of frustration. Being able to send a spreadsheet of who needs to travel from where to where, with times of arrival and departure would be a big win.
Wellness
Oh the stories I’ve heard about team retreats at some companies: Camping in a hot field. Partying til four in the morning such that no one can sleep. All night hackathons.
As a leader of a company, you have a responsibility to care for your people. A huge part of caring for your people is encouraging them to be well. Plan for an environment and schedule that defaults to wellness rather than burning the candle at both ends (people will burn the candle on their own anyways, but that’s their choice).
After hosting several retreats that included scheduled programming every night, we realized that it was too much. We stopped scheduling anything official after dinner aside from the first night. Believe it or not, people will use that time in ways that are best for them. Whether that’s connecting in small groups, reading a book, playing flip cup, or getting extra sleep — trust your people to do what will create the best experience for them when you give them their evenings.
We attempted to have our team share food responsibilities for our first retreat, then our founders’ wife volunteered to come along and cook for us, and then eventually the team got too big for any of the above. Now we hire a professional private chef to cater every meal for us. It’s fantastic. If I were starting over, I might do cook one meal as a team building activity at most, and then I’d hire a private chef to do everything else. It’s one less thing to worry about and if you find a great partner, the food will be delicious, healthy, and well-balanced (not to mention taking care of people with food allergies and preferences).
Finally, we make time every day for exercise. There is always an option in the early morning for people to move their bodies. We started adding a post-lunch group exercise time as well and this has been a big win since many people need the extra sleep in the mornings. By getting up and moving after lunch, the energy carries throughout the afternoon.L
As you plan retreats for your team, you’ll find the nuances that matter most to you. The best thing you can do is to have a single human on your team own the planning of the event. They’ll need help along the way, but having someone focused on every little detail helps to make sure logistics are invisible instead of distracting.
Objective 2: Have Fun
Your team already works hard (if they don’t, that’s for another post on another day). The goal of a retreat is not to get the maximum possible amount of work out of the team while you’re together. Retreats are not the best way to do this if that’s your objective. Perhaps consider another method.
Instead, having fun is a key component of what we want to achieve by getting together in person. “BUT BUT BUT, you’ve spent hundreds of thousands of dollars to HAVE FUN!?!?!? What kind of business person are you!?” Yes, yes we have spent that much money on retreats. And I can’t think of a better way to have spent that money to get a better return on the money spent.
If that resonates with you, then keep reading about how we create a sense of joy and fun throughout the week together.
Adventure
We always have at least one day of adventure scheduled into our retreat plan. This often comes early in the week to really get people out of work mode and into a state of being present where we are together.
In the past, this has ranged from zoo tours, to paintball, to a long hike to find an alpine lake, to zip line canopy tours, to whale watching, to rock climbing, to escape rooms. We always have at least two options for these sessions so that no one is uncomfortable. If anyone does not feel comfortable with any of the options, we make sure to make accommodations for them. The goal of all of these activities is to create shared experiences. Shared experiences create a deeper layer of culture that can’t be created through other means.
Games
We have fun with games on our retreats.
We’ve created an inside joke-driven custom Monikers deck that we play in small groups every retreat. It’s a way for long-time teammates to reminisce on hilarious company events and then to share the stories of those stories with newer members of the team. It turns into an oral history of the company every time, which is really special.
We usually have at least one night of board games. Evenings before dinner often come with a game of frisbee or corn hole. One retreat house had a sand volleyball court on the property, which led to nightly volleyball matches.
There are, as you might expect, occasionally impromptu drinking games in the evening. Drinking games are, of course, an important area to set expectations and guidelines. This is a work event at the end of the day, and while we want everyone to have fun, we never want to have fun at the expense of teammates being uncomfortable or excluded.
We always set expectations related to alcohol and drinking games that 1) harassment of any kind is never acceptable no matter the situation; 2) we expect each teammate to drink responsibly and know their own limits; 3) peer pressure to drink alcohol is never acceptable; 4) using water, sparkling water, juice, or any other non-alcoholic drink is highly encouraged; and 5) we ask teammates to play games in the established “main house” or “main living area” so that those who want to have a more relaxing experience have dedicated space to enjoy as well. We’ve found that these encouragements are much more inclusive of more people on the team than your typical drinking games centered on alcohol.
Free time
We build in free time throughout the week for people to find their own sense of fun throughout the week. We leave one afternoon open and most nights after dinner open.
Our teammates use this time to take a walk to an ice cream or coffee shop. We have The Bachelor and The Bachelorette watch parties. We have small group conversations about our life experiences, our families, and other topics that matter to us.
Relaxation
Finally, there is always at least one opportunity for as many people as would like to get a massage in their room from a professional. We also have teammates lead guided meditation and yoga sessions to help people be more present and connected to what they want from the week.
Fun is core to why we run retreats. These are some of the ways we build it in intentionally, but it’s also inherently a part of everything we do throughout the week… including the ways in which we encourage thoughtful and meaningful connection between teammates.
Objective 3: Make Meaningful Connections
Creating an environment where teammates can connect in meaningful ways and build strong relationships is on equal ground with having fun in terms of priority level. The stronger the relationships in a team, the more committed the team will be to the mission and vision.
Celebrations
The first night of every retreat is our chance to celebrate together. We gather before and/or after dinner on night one and do a few things. First, we simply welcome everyone and then open up the floor for anyone on the team to celebrate something we’ve done together over the past six months. This always leads to wonderful reflections, including on accomplishments that we’ve already forgotten about.
Then we hand out thank you cards with profit sharing checks inside. The practice is a known quantity, but the exact dollar amount per person is not. It always leads to gaping mouths, tears of happiness, and many hugs all around. Depending on the retreat, we’ve also celebrated in the past with personalized gifts for each teammate.
Every August, we do the ConvertKit awards one evening, which are voted on by the team. They include awards like The Smile Award, The Communicator, The Perpetual Learner, MVP, and more. It’s always a great time for celebrating people not he team as they are seen by their peers.
Listening walks
Our founder and I have both started working with coaches from an organization called Reboot, which was founded by Jerry Colonna. I first discovered Jerry Colonna through his friendship with one of my mentors and then through his podcast (also called Reboot). Eventually Nathan went on to attend a 2-3 day workshop with the Reboot team, where he was introduced to a practice called a listening walk.
To do the activity, everyone on the team partners up with one other person. We provide the team with a prompt. Something like: “What do you wish other people knew about you?” Or “How did you end up at ConvertKit?” They are intentionally broad, open questions.
The exercise takes 20-30 minutes. To start, each pair sets a timer for 10-15 minute. They start walking in one direction (down a road, around a park, whatever is easiest) and for the first 10-15 minutes, one partner talks the entire time and answers the prompt question. The other partner’s job is not to say a word, simply listen. Then, they turn around, set a new timer, and switch roles.
Upon return, we gather in a group and take volunteers to share what they learned from their partner (each partner has to agree to have their story shared first). The entire experience is meaningful on two levels. First, there is a strong bond between the partner pairs. Then, there is the added bond amongst the entire group by sharing each other’s stories.
Unsolicited feedback
Here’s the idea: too often, we share our most honest thoughts about other humans when they aren’t present. It’s safer and requires less courage.
But what if we could create an environment where people would share their honest thoughts — positive and critical — about one another directly. Kim Scott calls this Radical Candor. This is exactly what we do at retreats within each team.
Each team (marketing/engineering/customer success/operations/sales/product) gathers in a small group. One by one, each member of the team is on the hot seat for 10-12 minutes. When they are on the hot seat, they cannot speak. Everyone else on the team talks about them as if they’re not in the room. Then, the person on the hot seat gets 3-5 minutes to share their thoughts and/or ask follow up questions.
My favorite unsolicited feedback session of all is when the entire team delivers unsolicited feedback to the leadership team. For 30-60 minutes, we all gather in a room, the leadership team sits silently, and the team shares how they feel we’re doing. It is both terrifying and magical.
What comes out of this exercise are the most uplifting affirmations and the most honest feedback for continued growth. The result is deeper connection on all fronts.
Nathan has written about this practice before here. I also touch on it in my post about mastermind retreats here.
1:1 time
Each leader on the team goes into every retreat with a list of the 1:1 conversations we want to be sure to have while we’re there. We encourage the entire team to do the same.
Whether these conversations are used to get to know someone you don’t know very well, resolve conflict that’s been lying just under the surface, or simply reconnect with a close colleague on how their doing during this stage of life is not the point. The point is that every person on the team is intentional about having deep, meaningful conversations with their teammates.
Community Service
Finally, on most retreats we set aside an afternoon to do service work of some kind. We’ve cleaned up a beach and landscaped at a nature center, amongst other things.
During our August retreats, we’ve made a habit in the past of giving away profits to nonprofits in chunks of $100 at a time. We gather in small groups and each person shares a nonprofit they care about, why they care about them, and then they make a donation until the allotted money has all been allocated. Then we come back together and share about the groups we’ve chosen.
This inevitably leads to personal stories of why we’re connected to the work of these nonprofits. Someone’s relative died of cancer so we donated to a cancer research center; someone cares deeply about animals, so we donated to a dog shelter; someone volunteered with autistic children for years, so we donated there. And on and on. We get to see the giving sides of our teammates, which directly aligns with our core value of “Default to Generosity.”
We work hard to create intentional connections. Relationships at work can be shallow and arms length at times. We work hard to build connection on many layers amongst our teams. By doing so, we’ve found that people come to have a greater appreciation for one another, more understanding about the differences in our backgrounds, and a greater commitment to giving each other grace over time.
Objective 4: Dream about the future
We’ve learned repeatedly that it is not possible to over-communicate our mission, vision, values, and strategy as a leadership team. The team needs to hear these things from us repeatedly in order to fully understand and embrace them in their day-to-day work. Add to this the fact that we always have new teammates joining the team, and it is so important to communicate where we are going and then involve the team in crafting what that looks like today.
To do this, we have three sessions throughout the week:
- Mission, vision, and values
- Strategic plan
- Choose your own adventure
Mission, Vision, and Values
Nathan, our founder and CEO, is always the one to deliver this session. The core material is always the same.
Our mission is to help creators earn a living. Nathan shares how we’re progressing in terms of number of creators we’re serving through our content, our free trial, and our core application. He goes on to share how much money our customers have earned as tracked through one of our features.
He then goes on to share our progress against our vision and how we’re living out our core values. The core of this is always available for the team to read and reflect on here.
Strategic Plan
Each year, we make a strategic plan using a system called Objective and Key Results (OKRs). Each quarter, each team then breaks these year-long OKRs into manageable chunks for the next three months.
Throughout the year, it can be easy to forget what our long-term goals are and why we’re doing the work we’re doing. I take the opportunity during this session to remind everyone of our current year OKRs and how this adds up to our long-term vision. We’ve now started turning this session into an interactive one.
At our last retreat, we had three stations:
- What is a creator? — we bought about 100 magazines and had the team cut out their favorite creators (or print them from their computers if they couldn’t find them in the mags) and then taped them to a wall. The wall then became a massive collage of the people we want to serve and a source of inspiration for who we want to serve throughout the week.
- How can we help creators earn a living? — we brainstormed how we can use our content, product, and team to help our customers succeed.
- How can we find more of the creators we want to serve? — What marketing, sales, and community-building should we be doing to attract the kinds of creators we most care about?
This session helps us re-center ourselves on where we’re going and how we can impact that right now.
Choose Your Own Adventure
Every retreat, we have one or two blocks of time dedicated to choose your own adventure sessions. During these 90 minute sessions, we provide 4-5 options for the team to choose from.
Here’s an example of working sessions we might offer:
- The future of email marketing
- Compensation and benefits at ConvertKit
- Our three year product vision
- Increasing the diversity of the ConvertKit team
Each group always has one leadership team member participate, take notes, and bring the collective thoughts back to the leadership team as a whole so we can turn ideas into action.
Planning for the future is an important aspect of gathering in future. Keeping our team connected to our mission, vision, and values means they know why they’re doing this work and how to make decisions based on our share beliefs. Connecting to our strategic plan reminds everyone of how we’re moving toward our vision right now. And tackling important topics allows us to constantly improve the state of the company over time.
Objective 5: Make Concrete Plans / Get Good Work Done
Our last objective (and in some ways the least important) is to get good work done while we’re all together. There is magic in breathing the same air, being able to write on a white board, and debating great ideas over a table. To ignore this at our retreats would be silly.
Team work time
Every team gets 3-4 working sessions throughout the week. We leave these agendas up to the directors of each team. What I love about this is that we delegate the decision making to the people who are closest to the work.
Sometimes this might look like designing a new feature or answering support tickets. Other times it might look like two different groups within a team talking about how they can improve their process for working together.
Cross-team sessions
In any growing company, the teams within the company have to learn to work together well. There are interdependencies amongst every function and sometimes this can lead to conflict or frustration.
Many times, this conflict is just a result of not having had dedicated time to map out how they want to work together. In person time at the retreat is the perfect chance to talk through customer handoffs, building better systems, and integrating tools for better communication between teams.
Leadership work time
When we can, we also try to set aside time at retreats for the leadership team to gather and talk through our top priorities. We always have a running list of important conversations we want/need to have. There’s no better time than being in person to have them. We reprioritize this compared to time with our teams because we have 2-3 dedicated trips per year where we build our strategic plans and have long-term conversations about the future of the company.
Giving time to your team to talk about tactics and do work together is important. It’s not nearly as important as our other objectives, but we find that there is usually time for everything if your schedule well. If the team gets good work done, consider it icing on the cake for the week together.
Wrapping It All Up: Check the Doc
We have a saying at ConvertKit retreats: “Check the doc.”
Anytime someone asks a question about what’s coming up next or when we need to be where, the answer is always the same: “Check the doc.” Our operations team does a fantastic job of maintaining one canonical source of truth for the week in a shared Google doc. It has the schedule for sessions, the menu for food, responsibilities throughout the week, who’s staying in what rooms, and everything else you can imagine.
As I type this, I realize it would be a valuable resource to share a version of our doc so that you can benefit too. While we’re not ready to do that today, check back soon and I’ll make a downloadable version available so you don’t have to start from scratch.
Team retreats are the most powerful tool we have for building culture at Convertkit. Now that we’ve had seven retreats, we have it down to a great process. We’ve found that we get the most return from our time together when we get the logistics right, make sure we have fun, create opportunities for meaningful connections, and dream about the future. In addition to all of that, if we can get some solid work done that’s an added benefit.
If you run a remote team, I’d highly encourage you to test out team retreats yourself. If it’s anything like our experience, it’ll be worth every penny spent and every hour invested.