BL&T No. 120: Role-Playing for Team Growth

Company Culture

This post originally appeared in my newsletter, Borrowed, Learned, & Thought. BL&T is sent weekly on Mondays. In every edition, I share lessons learned in agency leadership, life, and e-commerce. This post does not include all the details shared in the newsletter sent via email. Subscribe here.


"Changing a unit’s culture means changing its members’ work norms and work-related values. These norms are established, held, and enforced daily by small social groups that take their cue from the group’s high-status member—the alpha. In general, to change the group’s norms, the alpha member must be replaced by someone who expresses different norms and values. All this is speeded along if a challenging goal is set. The purpose of the challenge is not performance per se, but building new work habits and routines within the unit."

From "Good Strategy Bad Strategy" by Richard Rumelt [Book]
(h/t Peter Kang for this week's excerpt. I'm currently reading the book myself.)


Dana and I hosted Christmas Eve dinner for the first time. Hosting family for the holidays has been a milestone we'd been looking forward to for some time, so it was special. Besides spending time with family (especially my little niece, Sofia), a highlight was surprising everyone with a gingerbread house-making session. I hope to continue this tradition next year — it's a simple way to bring a little child-like wonder to life!

In this week's edition, I'll focus on the last 3-2-1 Growth session of the year I ran a few weeks ago. What started as a question-based personal growth activity has evolved into a monthly team-wide activity centered around relatable situations involving the team and clients. I give the team a mock scenario and a prompt before splitting them into breakout rooms to workshop together. No one knows the prompt but me (including leadership). I find this helps level the playing field and allows everyone to participate.

Like any learned skill, the objective is to practice how to handle challenging situations while opening our eyes to new ways of thinking as we encounter similar ones in the future.


Since 3-2-1 Growth's inception, I've had fun updating the format and brainstorming what I think might resonate with the team. For the last session of the year, I was excited to take a swing and see how far I could push a new iteration.

While I'm continually impressed with the insights and discussions during 3-2-1 Growth, I started thinking about how to inspire team members to feel more connected to the scenarios by having to find their way through vs. merely prescribing solutions, which is often easier said than done. Rather than asking the team to discuss the situation in breakout rooms, I thought asking them to role-play might be the answer.

I'll admit — it took a lot of back and forth in my head before I felt comfortable committing to role-play. As effective as I thought the activity might be, I worried about the team being uncomfortable getting into character and not getting much out of the session.

I'm happy to report I was wrong! Let's dig into how the format of the session.


As we head into next year, a focus is facilitating more real-time feedback among the team through a monthly feedback practice. With that in mind, I wanted to concentrate 3-2-1 Growth on giving and receiving feedback.

This topic felt like a perfect fit to kick off the role-playing format because it's one thing to talk about feedback in the third person and another to give or receive it. I see it similarly to watching a sport on TV and critiquing the team's strategy vs. playing the game and working through a strategy as a team.

I hoped that by asking team members to assume roles, they would feel the feedback at their core and arrive at more powerful takeaways.

Each group had three team members in the following roles:

  • Bonnie, an account lead or
  • Clyde, an executing team member

The third role was called the observer. The observer's job was to listen, take notes, and bring back observations from an outside perspective.

Setting the Stage

I arrived at the mock situation pretty quickly. I figured a project-based challenge would connect with the team and could open the door for framing the feedback on something outside themselves: the client. Feedback is always personal — information about how others perceive us to help us grow. However, in an agency setting, there are often shared outcomes that addressing the feedback can help us achieve.

Bonnie, an account lead & Clyde, an executing project team member, have been working closely on a website optimization project for the past month. The client, Crook & Co, signed on for a monthly retainer with Barrel and provided a list of initiatives to get started. The client is motivated to launch an updated homepage and PDP to make the most of incoming holiday traffic.

The team is in two weeks out from launching these updates. Bonnie & Clyde have a scheduled one-on-one to discuss how everything has been going.

Getting into Character

I was trying to figure out the best way to replicate what it's like to give feedback to someone when you are unsure how aware of it they are. We've all seen the classic rom-com where the couple breaks up in the middle of the movie after seeing the same situation differently. We're sitting there wishing we could step through the screen and help unpack what's left unsaid.

Not too long ago, my mom organized a murder mystery party for my younger brother's birthday. I remembered that we all got cards with facts about our characters that no one else could see. I decided to replicate this for 3-2-1 Growth.

A couple of hours before the session, everyone received an email with background on their character. Rather than facts about who they were, I focused on how Bonnie and Clyder were experiencing each other and the feedback they hadn't yet addressed.

Here is what everyone received via email:

Bonnie: Your teammate, Clyde, has been slow in responding to communication, often leaving the team confused about the state of their work. Most recently, this led to a miscommunication with the client and a delay in the schedule. You feel they are making the project more complicated than it needs to be. You talk to your manager who suggests having a chat with Clyde.

Clyde: You’re having fun working with Crook & Co, but collaborating with Bonnie has been difficult. They always seem disappointed in your work, even when you think you’ve done exactly what they asked. You look up to Bonnie which makes this all more intimidating. You no longer feel comfortable sharing your perspective in meetings with Bonnie so you tend to stay quiet. You know this isn’t good for you or the project, but don’t know how to make a change.

Giving the Feedback

I purposely didn't provide much further detail before sending the team into breakout rooms. Typically they go into the session to work together to answer a question. This time, I focused them on a simple objective: Share how you're feeling (reference background in email) to align on the next steps for improving your collaboration.

When the breakout sessions were over, we came back as a group to discuss the takeaways. Using FigJam to capture notes continues to work well for this. We used these guiding questions:

  • What was most challenging about giving the feedback? Receiving the feedback?​
  • What next steps did you align?
  • If you could do this exercise again, what might you do differently?

Overall, the session exceeded my expectations. I was pleasantly surprised by the energy and enthusiasm of the discussions, but most of all, by how difficult it was for everyone to surface the feedback. Part of me worried that folks would open their email and read the background info out loud, but that was not the case. Instead, they cautiously navigated the conversation. If there's one thing this session highlighted, it's that we can all use continual practice in giving and receiving feedback! If handling feedback in character is challenging, imagine when it's real!

Takeaways for Next Time

I am looking forward to iterating on the exercise next year with a few takeaways in mind:

  • Role-playing works: After the success of this session, I'm anxious to continue exploring how we can use role-playing to practice challenging topics. It's proven effective in making mock situations feel real while having fun as a team.
  • More time for breakouts: I'm hesitant to extend this exercise from 30 minutes to a full hour, but we could use more time for the breakout sessions. I think the consolidated time frame increases engagement. Next time, I'll aim to minimize the upfront setup so we can dive into the session more quickly.
  • Expand the observer role: When helping team members work through feedback, I often find it helpful to get someone with an outside perspective in the room (if I'm too close to the situation). I didn't ask the observer to get involved in the session this time, but in the future, I can see their role acting more as a facilitator to the conversation than purely observing and taking notes. They'd have access to the background for both roles to help participants surface the unsaid.
  • Keep pushing the boundaries: I was nervous to try role-playing with the team, but I'm so glad I did. After the session, several folks commented on how much they enjoyed the exercise and some of the helpful takeaways.

Thought Starter

How might role-playing help my team improve collaboration?


The E-Commerce Corner

For brands looking to sell products online as their primary channel, relying on Amazon alone can be dangerous. If successful, it can be difficult to warrant investments in other channels, and yet, brands are at the will of Amazon. Instead, building a base with a DTC e-commerce store can help brands refine their business and understand their customers. Later, Amazon can create a halo effect acting as a trust-builder for customers and lower entry for a first-time purchase.

From Mark Zhang, the founder of Manta Sleep on "Shopify Masters: How to Take Your Brand Global" [Podcast]

Join My Newsletter

Every Monday, I share weekly themes and progress in running an agency business/team and doing my best to live a good life. Details