How I Plan a 3hr Retreat on Zoom

Step-by-Step Playbook for Remote Retreat

Last weekend, I held a remote retreat for my 7-person team at LivingOS. While I’ve planned many offline events before, I have never planned a remote retreat before. I did a quick search on my digital brain and several trusted knowledge hubs, but I didn’t find a playbook that fits my need.

To design a retreat that works for my team, I created a Messenger Poll to let my team vote on what they want to do.

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I also biased my team towards the items I want to discuss with * 🤓

Pre-Work: What We Did Ahead of Time

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  1. Personal Value Exercises: Due to popular demand, I created a worksheet to help my teammate find their top five personal values.
  2. Organizational Value Exercise: I created a team pulse check using the question framework introduced in The Five Dysfunctions of a Team by Patrick Lencioni. This survey helped me realize that my team struggled with the avoidance of accountability. While the book has recommended a few ways to address this dysfunction, we are still iterating to figure out which remedy works best for us.
  3. Write up Your Best Creation: Each member on my team owns a separate channel, and we love to celebrate our successes as a team. This not only helps everyone feel valued but also gives us the momentum to keep moving forward.

During the Retreat…

We split the three hours into bonding, brainstorming, and strategy.

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Full Retreat Agenda

Bonding

We started the retreat with the Yes And Story Exercise from Improv.

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The key is to be fast on your feet and build on what your previous teammate has said. Since you won’t have time to plan ahead, you need to pay full attention to what the previous person has said. You also have to take action — even though you don’t know what you are doing — which perfectly resembles the culture of our early startup days. After all, if you don’t fire bullets, how can you win the game?

After the ice breaker, we each used a few personal stories to introduce the personal values important to us at the moment. This gave us the context that we don’t normally talk about at work and helped us better understand each other. Due to privacy, I’m not going to share the personal values of my team.

Brainstorming

Before we get to LivingOS Principles, I want to feature what my team has accomplished in a couple of weeks 🎉

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Claire’s Awesome Work
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Elaine’s Awesome Work
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Mona’s Awesome Work
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Juhan’s Awesome Work
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Frank’s Awesome Work
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Charlene’s Awesome Work
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Chris’s Awesome Work

After getting a sense of each person’s scope and progress, we spent some time revising the LivingOS principles I drafted earlier. We soon found out that this project scope is larger than we thought. For example, we began to wonder:

How might we work on bigger projects together?

How might we set a universal objective?

We’ve got great progress on these questions, and I hope to share our learnings with you in the coming months.

Strategy

Building on the brainstorming inspirations, we brought many great ideas to the brainwriting session on Miro. We went through a few user stories, fleshed out the customer perception for LivingOS University, and identified a few big opportunities to work on.

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We didn’t get to cover everything, so we decided to finish up the next brainstorming stages asynchronously and sync up in the weekly meetings.

Overall, I have learned a lot from my team and plan to run the next iteration in the near future.


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