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  • Writer's picturejoshlevine


Updated: Jun 7, 2022

Establishing rituals at a workplace can bring more than just fun events to an organization’s social calendar. Group activities build and strengthen relationships, and that’s particularly valuable as we grapple with a hybrid workplace. Below is a case study from The Design Gym written by Jason Wisdom, Co-Founder + Managing Partner.



In getting an organization off the ground, EVERYTHING in the early years is constantly changing. Not just the vision and the offering, but the approach of how things are being done and by whom. This constant change can cause friction within any team, but we found it especially true between our partners. Over a period of months there came a certain point where we just weren’t comfortable with the feeling in the office anymore. There were many unstated frustrations that we weren’t talking about and went on a search for solutions based on our values. Our fourth internal value is “Feedback is a Gift” and while it’s often a gift I’d rather not receive I’ve grown tremendously because of it.

Our Solution

What we came up with is pretty simple but not easy… It’s a weekly meeting we’ve developed that we call Uncomfortable Conversations and it’s exactly what it sounds like.

Uncomfortable Conversations is an opportunity to get our partners into a room on a weekly basis to talk about our personal anxieties, frustrations with each other and frustrations with ourselves. We acknowledge our personal lives and work lives are completely blended and something causing stress in one area will undoubtedly bleed into the other.

Our Approach

In the same way that the business world draws a great deal of inspiration from design, I’ve found when trying to build a strong organizational culture there’s a lot to be learned from relationship counselors. For example, a common way to present feedback to a partner or spouse is by saying; “When you do (x behavior), it makes me feel (x feeling).” This phrase works because it’s much more focused on acknowledging behaviors and personal emotions then assigning blame.

Internally, we’ve worked on taking this one step further: we expect each other to call out moments where we feel like our own actions or approaches might have missed the mark or created discomfort for someone else, instead of waiting for someone else to bring it up. For example, if I felt I made a mistake in a client call that I was on with my partner, instead of waiting for my partner to say, “I wish you had handled that call differently,” I try to be proactive and say to my partner, “I’m not sure I should have handled the call that way. What do you think?”

I often categorize our work as much more Dr. Phil than designer. We have developed the ability to help our clients better understand their own internal dynamics because we are constantly working on ourselves, and our own culture, especially when it’s not comfortable.

Credits: thanks to Jason Wisdom for sharing his story and to The Design Gym for doing amazing work worth sharing.

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