An Open Feedback Session Inspired by the 20 Habits in "What Got You Here Won't Get You There" by Marshall Goldsmith

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Borrowed & Learned

Last Monday, I hosted our quarterly Team Leads session. These meetings are a chance to pause, reflect, and plan for the coming quarter. We usually read something in advance and discuss takeaways together, then review the agency-wide debrief notes from the prior week to define next actions. In preparation for this session, we read Getting Things Done by David Allen in its entirety and an excerpt from What Got You Here Won’t Get You There by Marshall Goldsmith.

I first read Getting Things Done in 2019, which significantly impacted how I operate today, personally and professionally. The concepts in the book felt especially relevant to many of the discussions we’re having lately, so I thought it would be worth digging into as a group. Our discussion focused on how to be more effective individually and as a team, especially in managing our clients. Everyone got a lot out of it. A fun idea from this discussion was to share excerpts with the broader team in our internal newsletter, Barrel Insider, for all of Q2 to expose them to the concepts.

The GTD conversation alone could have taken up the entire session. But the second part, which I initially hesitated to add to the agenda, was incredibly impactful.

Over the past month, one of the books I’ve been reading is What Got You Here Won’t Get You There. It felt particularly relevant as I reflect on my transition into the CEO role and opportunities to improve. The author, Marshall Goldsmith, is an executive coach who’s worked with high-performing leaders across industries. One idea that stood out to me was this:

“At the higher levels of organizational life, all the leading players are technically skilled. They’re all smart. They’re all up to date on the technical aspects of their job. … That’s why behavioral issues become so important at the upper rungs of the corporate ladder… even when all other things are equal, your people skills often make the difference in how high you go.”

I distinctly remember going through this transition, where my skills as a designer started to matter less than my ability to lead a productive team. This concept got me thinking about our leadership team, not only how they’ve gone through a similar experience but also how we’ve been navigating a lot of change over the past several months. When things are moving fast, it’s easy to deprioritize interpersonal dynamics in favor of execution or strategy. But what if those conversations ultimately make or break our success?

In planning our quarterly session, I’d been toying with a few exercises to include in the meeting, but I wasn’t sure how a feedback-focused one would land. But when I came across Goldsmith’s “20 Habits,” it clicked.

These habits, like “adding too much value,” “withholding information,” and “failing to give proper recognition,” are small behaviors we often unknowingly adopt but can create a ton of friction if left unchecked. The exercise I designed asked everyone to reflect on their strengths and identify habits from this list that might be holding them back. Then, to do the same for one another

In the meeting, we started by sharing personal reflections, then highlighted what we appreciated about one another and where we saw opportunities for growth. I especially valued getting feedback from the team and having the space to talk through ways we can improve how we collaborate moving forward. One example that came up for me was a tendency to “add too much value”—jumping in with suggestions or solutions in situations where it may not be necessary. I’ve realized that sometimes a Team Lead just wants to share, vent, or talk something through, not get immediate input. A quick check-in on what they’re looking for in the moment could save us both a lot of time. On me to ask, not assume.

Everyone admitted some level of hesitation coming in. I sensed that might be the case, so we started with a few meeting norms to help ground the discussion:

We all can be better collaborators.
We believe feedback is information.
We trade all judgment for curiosity.
We communicate openly and honestly.

Once we got going, a sense of ease filled the room. The conversation was thoughtful and respectful. No attacks! Most of us were harder on ourselves than anyone else. Goldsmith says, “Just as people tend to overestimate their strengths, they also tend to overrate their weaknesses. They think they’re really bad at something at which they’re only mediocre or slightly poor — an F when they’re really a C-minus. In other words, they see cancer where a professional would see a muscle pull. So let’s hold off on self-diagnosis for a moment.”

It was a helpful reminder not to let self-reflection outweigh what others experience in working with us.

We didn’t get through the entire agenda and had to finish the agency-wide debrief review later in the week. But I left the session feeling like we used our time well. These conversations will only become more critical as we build on our momentum. It doesn’t matter how smart or skilled we are if we can’t be honest with one another about what’s getting in the way.

I know this one exercise won’t change everything. But I hope it creates the groundwork for a more fluid, ongoing exchange of feedback. Before we wrapped up, we talked about how valuable that kind of dialogue could be, which reminded me of something I’d written before:

“Feedback is information that we do not have access to on our own… We can choose to resist it, but the fact is that the feedback, or the way others perceive us, is not reliant on whether or not we are willing to face it.”

All in all, I’m grateful we made the space for this discussion and to the team for really showing up.

Note to self: Sometimes, the part of the meeting you’re most unsure about is the most important. Always worth going with your gut and giving it a try.

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Highly suggest checking out the book, but for now, here's the list of 20 habits: