7 lessons from 7 days at a remote startup’s annual retreat

Two weeks ago, 110 Tyklings from over 15 countries descended upon Cancun, Mexico, for a 7-day working retreat. Some colleagues were coming face-to-face for the first time; others were gleefully reunited; all were ready to work together and make Tyk a household name. 

Like musicians might head to the countryside to write an album or writers enter into the woods to finish a book, we Tyklings fly to stunning, palm-fringed beaches to connect, brainstorm, reflect, and plan our priorities for the year ahead.

Seven lessons, 7 days. Here are our learnings from the week. (Spoiler alert: retreats are freaking great)

1. It’s essential to break down silos 

You don’t realise your company is siloed unless you talk to other colleagues in person and try to break that environment. When people get together, they develop a unique relationship.

A lot of the magic of retreats is that teammates interact in a less role-based fashion. Opening up new lines of communication is essential to breaking down silos of all kinds, where many of us discovered that other teams’ processes and priorities aren’t as different as once thought. 

Siloes be damned! 

2. The best workshops are interactive 

In successful workshops, attendees become active participants who contribute to the outcome. Our sessions were filled with exciting and non-orthodox ideas, which align perfectly with one of our core values; ‘the only stupid idea is the untested one’

All our workshops had these three things in common:

  • They were intimate and interactive – no one could hide in the back like they might in a lecture
  • They set the stage for learning, growth, and relationship building
  • They were spontaneous, complete with unexpected sparks of creativity. Nothing was off the table! 
  • They sparked engaging experiences and forward momentum for teams and individuals.

We started our workshops with icebreakers, used a real-time polling app called Sli.do and incentivised participants with competitions to get the participation ball rolling. 

Workshop champions! 🥇

3. Context and personalities can get lost in Slack

As a fully remote company, we rely on tools like Slack, Zoom and email to stay connected. Tyk champions asynchronous working, but it does run the risk of an instant message tone-of-voice gone wrong. When you get everyone together in person, you learn quickly that context and personalities can get lost in translation. 

We encourage all Tyklings to always assume best intent and remember that everyone is on the same team. Working from across the globe, it can sometimes be easy to forget that if you’re having a bad day! 

Putting a face and person behind the tiny little profile picture that you talk with on Slack is valuable. Getting involved in workshops, playing games and sitting down to dinner with your colleagues (with or without a frozen margarita) creates a meaningful bond you can’t get digitally.

Bonds being made 😀

4. Mixing different teams creates a growth mindset

In Mexico, our teams embraced a growth mindset by attending workshops hosted by different business functions. People were encouraged to sign up for sessions hosted by different departments where they could learn new things and work with people they’d never met. 

Returning from Mexico, our bags and hearts were full of new ideas, memories and in-jokes that we can take back to our laptops for future collaboration. 

Serious brainstorming! 🧠

5. Cross-functional collaboration gives you a voice

Large organisations can sometimes fall into an ‘us’ versus ‘them’ mentality, creating issues with culture and communication.

Cross-functional collaboration makes you feel like you have a stake in the different functions across the organisation. When people feel like they don’t have a voice, they can start to check out or struggle to understand different strands of the business.

In Cancun, our Tyklings had the chance to break down those barriers by providing an equal footing and inclusive environment in which they could learn, get involved and have an impact on what other teams are up to. We’re big on ideas at Tyk, and in our sessions, we encourage creative and outside-the-box thinking, which resulted in some pretty awesome action points to take home with us. 

When people in UX get facetime with those in Marketing over tasty tacos while watching the sunset, that’s a pretty darn loud and powerful thing. 

“Everyone say tequila!” 🇲🇽

6. We’re all humans working towards a common goal 

Poor alignment and communication can impact the outcome of any business project, big or small. 

Our retreat has served as a reminder that no matter how remote we are from one another, most of the time, we’re all just humans working towards a common goal. This links with another of our values in that it’s OKAY to screw up. Every successful discovery follows a glorious parade of failures, experiments and grazed knees – so get out there and give it a shot! 

Getting our Tyklings together in a low-pressure environment meant they could embrace our business values and goals in the same direction, celebrate wins as a team, support one another and work to achieve the results we want. 

7. You find out how tall everyone is!

Sometimes, it’s the little things you miss when you haven’t met someone in person. 

“I’m excited to see how tall people are”

“No one is a floating head anymore!”

“I told everyone I’m 6″6’ for a laugh.”

Strictly speaking, you can be anyone you want on Zoom. But we want everyone to be just as they are. And we were delighted to meet their true, authentic selves in person. 

Post-scavenger hunt happiness 🎉

A Tyk good time 

While seven days may seem extreme, we’ve found it to be the magic number for building meaningful relationships across the entire organisation. 

We empower our Tyklings to always try to leave things better than they found them. It is all about embracing change and driving that change in every step they take. So, as everyone arrives home, the one thing that we hope everyone brings back with them is the importance of culture and how they can help bring this to life through better Tyk experiences. 

Now the jet lag has lifted, we can’t wait for next year!