What I've learned from 10 ConvertKit retreats


Hey Reader,

We just finished our 10th ConvertKit team retreat. We went to Cedar Lakes Estate in Port Jervis, NY. It's a gorgeous summer camp turned wedding and retreat venue with a lake, hiking trails, and beautiful grounds.

This one was extra special for two reasons: first, we had almost all of our team there (59 out of 68) for the first time in 2.5 years, and second, it was our 10th in person retreat!

To celebrate I figured I'd share 10 things I've learned from hosting 10 in-person retreats:

  1. Know what you want from the retreat — Early on at our retreats I was just so excited to meet people for the first time. But as we did more retreats I articulated our goals for the retreat in 3 words: connection, ownership, and service.
  2. Focus on connection — Our #1 goal is for team members to connect and build strong relationships. Which you can do so much better in person.

    We'll deliberately plan to pair team members up across teams for car rides, activities, and more so they can spend time with someone they don't work with day-to-day.
  3. Take ownership – As the company has grown and retreat budgets have increased it would be easy to fall into a pattern of "how will you entertain me today?" If something goes wrong it's on the organizers. Or maybe the final night of entertainment wasn't as good as last year.

    We want team members to take ownership of their own experience and provide the entertainment. That ranges from a DJ battle hosted by one of our engineers to my favorite ritual of all:

    Each retreat the a small group writes a speech for me that I deliver on the final night—without having read it first. It's hilarious, filled with inside jokes, and just ridiculous all around.
  4. Serve others — Along with ownership, we want our team to think about how they can serve their fellow co-workers. What can I do to make your experience better? How can we serve creators better? What about our community? Some of the favorite retreat activities have been trail maintenance at a nature preserve and a beach clean up day with Surfrider.
  5. Make it personal — I'm always looking for ways to help team members feel seen and valued. At our first team retreat Ashley (our VP of Operations) and I spent many hours researching and buying a personal gift for every person on the team.

    One team member had made an off hand comment in Slack that her waffle maker had broken and she missed her routine of Saturday morning waffles. So we surprised her with one. Someone else loved both the outdoors and whiskey, so we got these cool whiskey glasses with pacific northwest mountain peaks in them.

    We spent a lot of time buying and wrapping presents for 21 people and it was completely worth it for the reaction! Everyone felt seen and valued. A few years later we did it for 40+ team members as well.
  6. Create magic moments — In 2018 we surprised everyone by issuing equity and making every team member an owner. We could have done that over zoom, but we deliberately waited to do it in person because it would create a moment we'd never forget.
  7. Build rituals — The first night of the retreat we always gather for profit sharing and celebrations. We take some time to celebrate what we've accomplished in the previous 6 months (we do retreats twice a year). It's such a great time to pause and reflect. Then we open cards that have each person's share of profit sharing and hand written notes from the executives.

    This consistent ritual, which we've done for 10 consecutive retreats, has become something that everyone looks forward to.
  8. Reconnect with your mission — At ConvertKit we exist to help creators earn a living. The retreat is the perfect time to tell stories (Isa, our resident storyteller, always has a few good ones ready) to show the team the impact our work has on tens of thousands of creators.

    Early on leading ConvertKit I didn't realize just how often we need to emphasize and repeat our mission. Now I know just how important it is to have that consistent voice over time.
  9. Make a list of who to connect with in advance — As the team grows you won't be able to talk to everyone (though I still try), so I make a list of 10 people that I want to make sure to have a real conversation with. It could be that they are new to the team and we haven't met before or there is something specific I want to talk to them about.

    That prep work means I always make time for the most important conversations.

    I also like when a small group gathers and I can ask them questions about ConvertKit from their seat. One of my favorites is "If you were CEO tomorrow what is one of the first things you'd change?" I find that after 11pm and maybe a drink or two the answers get really good!
  10. The food and venue matter — At every retreat we try to choose a venue where the whole team will be in relatively close quarters and we have a full buyout. This last one we had amazing cabins in nature and all of our dining was outdoors. It just created a great setting for connection.

    We also had absolutely incredible food. 3 meals a day for 5 days and I didn't eat a single thing that wasn't excellent. Early on I wouldn't have said that was as important, but watching how well everyone connected over great food.

I'm sure there's more, but that's my quick list.

I love team retreats and I'm already excited for our next one in January in Mexico.

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FROM THE PODCAST

Turner Novak - Easy ways to Ignite Your Audience Growth

The podcast is back! After taking the summer off to focus on growing ConvertKit, I'm back with more interviews.

Turner is someone I’ve followed for a long time. He has an amazing Twitter account where he drops hilarious memes, talks about life as an investor, and makes fun of venture capitalists and founders.

In this episode Turner and I talk about how he creates content. We get into how he uses his funnel to raise capital, and how to generate the highest return on investment (ROI) for your audience. We also talk about how he grew to 130,000 followers on Twitter, why he failed to get a job in venture capital and had to start his own firm, and how to create a successful newsletter.

Watch the whole episode here »

Have a great week,

Nathan

Nathan Barry

I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.

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