BL&T No. 040: Learning to Let Go As A Manager


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.


"Good decisions are not made by those who are running on empty."

From "Stillness is the Key" by Ryan Holiday [Book]


Many years ago now, I met up with one of the co-founders of an agency I admire. Let's call this person Tyler. It was a Monday morning in the Fall, right when the trees peppered around the city start to introduce warmth in a sea of gray. Tyler and I met upstairs at a restaurant near his office. I sat facing the window, looking out at an unforgettable view of the New York City skyline.

I had only spoken with Tyler once before, so nearly everything we discussed was new territory. I was curious to dig into his journey, day-to-day, and gain insight into what it was like to manage a team nearly ten times mine. Right out of the gate, I was taken aback by how much stress Tyler was under at work. Well, the source of the stress was more surprising than the stress itself.

Despite co-founding and scaling his agency, Tyler was still working alongside the team on client projects. At the time, I was beginning to realize that if I wanted my team to grow, I needed to distance myself from client work. It was tough to balance execution with my responsibilities as a manager and discipline lead. As much as I enjoyed designing, I could see that I was becoming more valuable to the team as a mentor and soon found more fulfillment developing them in their careers than doing the work on my own. But, as Tyler described his situation, I thought, am I headed on the right path?

Anxious to learn more about Tyler's approach, I probed him for more context. He talked about the challenges of managing 20-some direct reports while simultaneously working on client projects. (Side note: From personal experience and chats with folks like Tyler, the general consensus is that any more than eight or nine direct reports are too much!) We dug into team hierarchy and role definition. Tyler went on to share how he approached employee promotions: "If a client selects their concept over mine, I know they should be more senior."

I had reached out to Tyler to get advice as my role and team evolved and grew. Tyler was successful, had a beautiful home, and a happy family, but at work, every day was a marathon. Between check-ins with his team, finding time to work, and attending client meetings worldwide, his stress seemed to be dipping into his life at home.

Toward the end of our morning together, Tyler offered one last piece of advice: "If you're not doing the work, expect 80%." This simple concept seemed to drive most of his decisions, and the weight he carried was a by-product. There was no trust. For Tyler, it meant that his involvement was the only way to get it perfect, to get it 100%. For me? Well, I interpreted it differently, leaving our conversation with two questions:

  • What can I do to increase this percentage?
  • What do I need to do to be comfortable with less than 100%?

I was reminded of this story during a monthly one-on-one last week with a designer. I enjoy sharing it with new mentors and managers because of the profound impact it has had on me. This designer was overseeing a couple of projects for the first time, and in their words, struggling.

I told them about the 80% rule, and we workshopped the two questions. Having had this conversation more than once now, I'd figured I'd share some of the ideas here for future reference.

One way to raise that 80% is to take the time to craft and articulate a vision. Know where you want to go with the work before you embark on the journey. Show the possibility of what you can create together and get feedback. Document the key ideas in writing and gather visual references to align before the person doing the work gets started. With this in place, they can take ownership and make it their own.

Once the work begins, the key is to address and dismiss two thoughts that will inevitably pass through your mind at some point or another:

  1. "I could have done it faster." Of course. I'd hope so - you're more experienced. Either way, it would have taken more of your time than you're spending providing oversight. Think of the time spent as an investment in the future. Someday, the person you're mentoring will be equipped with the skill to do what you're doing. That means you can move on to the next step in your growth journey. Not to mention the time you've gained to work on higher-value activities like coaching your team and shaping process.
  2. "I could have done it better." You're right. You could have, especially if you're the only judge. You're a judge, but the client is the judge. Once you ignore the idea that you do it best, you might be surprised. Everyone has their strengths, and when you can help someone find and flex their own, they shine. I love seeing work from our team and thinking, wow - could I have done that?

In the end, not everyone wants to be a mentor or manager. With that said, if it's in the cards, don't view it as a competition. Be a coach, not a contender. The more you grow, the more you should be asking: how can I make myself obsolete? Put another way, what can I do to make my team successful without me?

Since my conversation with Tyler, this mindset has been freeing. It's led me to develop a system for the team to lead projects at all levels, freeing me up to focus on higher leverage activities. Tyler gave me a glimpse into what it looked like to keep a tight hold on the work, unwilling to let go. I can't speak for how his team felt, but I do know this: he was in over his head with little attention on any one thing and, instead, feeling stretched thin between a ton.

Lesson? The measure of a manager is not how well or fast they can do the work on their own. It is how well they inspire, lead, and support their team to work just as, if not more, effectively.

Thought Starter

What could I offload today (and trust my team to manage) to make me more focused and effective tomorrow?

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