What is the Olark retreat?

We recently completed our fourth-annual, week-long, all-hands, extra-hyphenated Olark retreat. Since then, I've been fielding lots of questions about our retreat from curious friends: Why do you do it? What do you there? Should my company do a retreat?!

The answer to that last question is unquestionably yes, although it might look very different from ours. To understand why, let's start at the beginning.

Every year Olark takes time to get out of the office and think  about live chat software.

Why do you do a retreat?

Long-term thinking is crucial to the long-term success of your company. Not everyone needs to be thinking long-term all the time, but everyone needs some time to step back from their day to day, discuss issues, think critically about solutions, and make adjustments. The Olark retreat lets us change the scenery and have those conversations.

This may sound serious and somber; in reality it's anything but. Sure, there's reflection and introspection, but we're also celebrating the past year and building our plans for the year to come. It's our big opportunity to celebrate the past, reflect on where we are right now, and plan for the future.

There's also an Olark-specific reason we do the retreat. Our team works out of over 20 different cities, and the retreat is a great occasion for everyone to meet face to face, hang out together for a few days, and learn things about each other that you just can't get from a Skype call. You don't have to be best friends with all your co-workers, but the way you come to understand someone by spending time with them simply can’t be replicated through any other means.

Throughout the year, when your collaborators are 1,000+ miles away, that understanding becomes a crucial foundation for your work relationship.

What do you do there?

Now that we’ve done four retreats, we've arrived at a structure that works well for us. Each year is a slight variation on this structure, but here's the general outline:


  • Everyone travels to the location.

Saturday + Sunday

  • Have fun together! There are lots of activities for Olarkers, their partners, and their kids. Some activities are for small groups, others are intended for everyone. Nothing is required ("fun is mandatory!") so if you prefer hiking, raucous karaoke, or lounging around the pool, there’s something for everyone.

Olark karaoke sing along - Company retreats can be a pretty awesome time.Well it's 9 o'clock on a Saturday...


  • We kick off the work week with the only required event - our State of the Olark presentation. It's a one-hour face-forward presentation the four co-founders give celebrating the past, reflecting on where we are, and setting up a framework to think about where we're headed in the future.

I've always found preparing for this presentation to be one of the most time-consuming things I do at Olark. Be sure to give yourself plenty of time to prepare! Check in with your team ahead of time on what they want to see covered, and remember nobody expects you to have all the answers. You're giving your team a framework for the future, not a blueprint. As your team tackles the challenges of the next year they'll learn new things, so any plan will have to adapt.

  • The rest of Monday is an unconference. I could spend a whole post just talking about unconferences - they are my favorite format for quickly sharing knowledge and learning - but here's a quick summary: instead of having the usual face-forward conference presentations, at an unconference you have collaborative discussions. You can brainstorm topics ahead of time, but the final choice of topics happens right before the event so they can come from discussions / discoveries that are happening at the retreat.


  • The unconference continues! I would recommend having no more than four sessions per day (although you can have multiple sessions running in parallel) and having some sort of quick summary from each session at the end of the day.

Wednesday + Thursday

The Olark Ignite Talks are short talks about any topic the presenter chooses.









We like to leave unstructured time towards the end of the retreat so there can be small breakout sessions, hackathons, or mini-research projects inspired by the past week. If you want to plan out a radical experiment that affects the whole team, this is a good time to iron out the details.

…and that's our week! There are a ton of other events that happen during the week and in the evenings (ask an Olarker about Kudos boards, Ignite, Olarker Bingo, etc...) but that’s the general structure.

So back to that question we had in the beginning:

Should my Company do a Retreat?

You definitely should, but I wouldn't recommend copying the Olark retreat beat-for-beat. Your retreat is a great chance to reflect your values and your culture, so make it your own!

If you've never done a retreat before, start small. My first company retreat (before I worked at Olark) was one day long, at a local community college, and we had a box lunch (although the company did take us out for dinner afterwards). It was frugal, and short, but it was exactly what we needed. It energized the team and helped uncover issues that would have grown in to serious problems if they weren't addressed.

There's so much more to tell. Hopefully in future posts other Olarkers will chime in with their take and fill in more details, but I hope this post has inspired you to build or tweak your company retreat!

READ MORE: How Olark customers build their retreats

Check out relevant topics on: Olark Essentials

Zach Steindler

Read more posts by Zach Steindler

Zach is a co-founder of Olark live chat.