BL&T No. 054: Leaning Into Discomfort


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.


"If we can restore the collective attitude that leadership is meant to be a joyfully difficult and selfless responsibility, I am convinced that we will see companies become more successful, employees more engaged and fulfilled, and society more optimistic and hopeful.”

From "The Motive" by Patrick M. Lencioni [Book]


One of the highlights of last week was chatting with the senior designers about their career growth and role at Barrel during our Wednesday one-on-ones. These conversations came as a follow-up to our monthly design leadership meeting on Monday when I announced they would no longer report to me. Starting in Q4, Christine, Design Director, will be their manager.

Having spent most of my time at Barrel building the design team, this was quite a milestone. I always knew the day would come, but there was never a set timeline, so it felt somewhat surreal.

When I became Chief Experience Officer (CXO) in May, Christine and I aligned on a future where she'd take the lead of the design team. I always prefer gradual changes and wanted to make sure Christine felt ready. Rather than make any abrupt changes or set a rigid timeline, we agreed that I'd slowly transition my responsibilities to her, and together, we'd discover the evolution of her role. This included more regular check-ins and collaboration with the senior designers, which I believe contributed to their support for the recent change.

As a quick aside, I'll say that it's been a pleasure to see Christine thrive throughout the last several months, taking ownership over design team rituals, experimenting, and making them her own. I am grateful to have her as a collaborator and eager for everything that's in store.

Despite the seniors feeling comfortable with Christine becoming their manager, I felt inclined to check in and align on with them on how they fit into the evolving team structure. The announcement was exciting, a sign of growth and progress. I wanted to be sure the seniors knew what it meant for them. While I always end up enjoying these conversations, I'd be lying if I said I didn't often feel a tad uneasy beforehand.

There's a side of me that feels confident that I have a good handle on the team's sentiment toward the work, personal career goals, and so on. But, when it comes time to put these beliefs to the test, there's a side of me filled with doubt. What if my version of this person's future is different than their own? What if I open a can of worms and we discover that Barrel can't offer what this person wants?

To get past these fears and not put off the conversation, I remind myself that both scenarios would still be positive. If either led to the person moving on, I'd be sad to see them go but glad that it came from an honest conversation.

Digging In

I started each one-on-one with a question that went something like this: Think about how your role has evolved so far, what have you enjoyed most? Now, look ahead to 3-5 years in the future, where do you hope to see yourself? What does your day-to-day look like?

I purposely didn't anchor the conversation on titles and shared why. One reason is that titles mean different things to different people. To me, what you're called is not as important as what you're doing. Fun fact: Christine loves her Design Director title because of the alliteration (her initials happen to be CC) but if she hated her job, who cares about her title?

Another reason is that there are roles that don't exist on our team yet. Part of what I hoped to gain from these conversations was confirmation on where to take the team structure next.

The one-on-ones couldn't have gone better. I could tell that each of the seniors had spent time reflecting on their growth. They all started at junior or mid-level roles, so their history at Barrel is rich. It was a pleasure to hear them talk about what they've learned about themselves over the years and what makes them feel most fulfilled today. It was also reassuring to find that we were in sync.

Two of them find joy in the work itself. Whether it's executing a design or guiding a more junior designer to execute on their's, they see themselves as life-long creators. The other senior talked about feeling happiest when they're coaching others and working toward a common goal. In each conversation, I described how these insights could translate to future roles.

For two of them, it means building out an individual contributor (IC) track, something I've been looking forward to establishing for some time. This means creating a growth path for non-managers. Essentially, they will continue to hone their craft and mentor others without ever taking on direct reports. The other senior will follow a manager track. Much like Christine managed a portion of the design team while I was Creative Director, this person will eventually take on direct reports at the junior level.

Each one-on-one evolved into a discussion about the future of the design team, from project types to talent pipeline. As much as I feel like I share, I realized there were still gaps. I enjoyed catching them up on the latest developments and divulging works-in-progress.


I recently finished reading a book called The Motive by Patrick Lencioni. Thanks to Peter, Barrel Co-Founder / CEO, for recommending it to me and the other partners. A theme throughout the book is how critical it is for leaders to engage in the activities that sometimes they'd rather avoid:

"[T]hese five areas—building a leadership team, managing subordinates, having difficult conversations, running effective meetings, and constantly repeating key messages to employees—are not a list of the key responsibilities of the leader of an organization. These are simply the situations and responsibilities that leaders avoid all too often when they don’t see it as their job to do the things that no one else can."

Reading The Motive couldn't have come at a better time. Reflecting on the book and this past week's events got me thinking about all of the conversations that led to where we are today. Each was unique in its own way but often unpredictable and, at times, uncomfortable. If I hadn't found the courage to facilitate them, I'm not sure that a milestone like this week would have ever happened.

Lesson? As a manager, my job is to help the team achieve great outcomes. That means doing what's best for the team down the road, not what feels comfortable for me at the moment. Rather than shying away from feelings of doubt or discomfort, I can embrace them as fuel to learn and be a better leader.

If you're interested in "The Motive," check out Peter's recent post reflecting on the book here.

Thought Starter

What conversations or responsibilities am I avoiding?

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