14 Lessons Learned in Agency Leadership

On June 1, 2020, we celebrated 14 years in business at Barrel. I’ve been with the agency for seven years, exactly one month shy of half of that time.

I came to Barrel on a freelance design contract. I was one year into my first job post-college. It wasn't going as I had hoped and Barrel had everything I was looking for. At the time, a freelance position was scary and exciting all at the same time. The future was unknown but I gave it my all and it paid off.

Needless to say, it's been a special experience. Seven years ago, I never would have thought a "job" could have such a profound impact. I feel lucky to look back over the years and only see progression.

Among the partners, we have a saying: "No good days. No bad days. Just days". This couldn't be more true about our history. Rather than focusing on the past, we do our best to look forward. Every misstep is an opportunity for growth.

To keep this spirt alive, we practice constant communication and consistently hold each other accountable. As a leadership team, it's easy to get lost in the shuffle of the day and lose sight of what's important. To make sure that's never an excuse, we have a 2-hour weekly standing meeting, annual/quarterly planning meetings, monthly dinners (pre-COVID) and since transitioning to a remote company, we meet at the end of every day.

It's been incredible to see the impacts of this level of communication.

Lessons Learned

In celebration of our 14 Year "Barrelversary", we set time aside to reflect. In absence of dining out, we set up a Zoom call and all ordered the same bottle of wine in advance (8 Years in the Desert by Orin Swift).

We each prepared for 14 lessons we valued the most in running the business. This was a lot of fun. I had never really spent focused time to reflect on what lessons the past had taught me. Once I got to thinking and writing, it was hard to stop. The hardest part was slimming it down and prioritizing.

Below are the 14 lessons I landed on:

  1. Never fear honesty. Honesty inspires honesty. When everyone shows their cards, it's much easier to make progress.
  2. Clients, employees, colleagues, friends, family... They’re all people. People with their own busy lives, ideas, goals, life/work pressures, etc. Everything becomes a whole lot easier when we recognize that and treat them as such.
  3. Listen with an open mind. Be willing to leave every conversation with a new perspective or approach.
  4. Real leadership goes unrecognized. It's mentoring and coaching that creates a team who can succeed without the leader being on the front lines.
  5. There is no such thing as a good day or a bad day. They're all just days with their own successes and challenges. Nothing is the end of the world. Stay focused on moving forward.
  6. Time spent on people is time well spent. If your team doesn't grow as leaders and contributors, neither will anything else.
  7. People need encouragement as much as they need feedback and guidance. It’s hard for people to thrive when they don’t know how they’re doing. Uncertainty holds us back.
  8. Don’t expect a big announcement or policy to instantly create change. Work with your team to solve at the systems level and get buy-in. Experiment, debrief then focus on roll-out among the larger group and repeat. Change will follow.
  9. Everyone learns differently so the same training can't work for everyone. As leaders, it’s our job to find what works for every team member, not their job to figure out how to work with us.
  10. It’s one thing to trust your team, it’s another for them to feel trusted. Let go. Give them the slack to succeed and fail on their own. People learn the most when they feel in control.
  11. When things don't work out, point the finger inward. The only way to improve is to know where you can do better next time.
  12. Every person carries with them a unique set of beliefs, experiences, and skillsets. Don't project yours on anyone else. Instead, spend time understanding others and how your experiences can help them grow. Instant satisfaction guaranteed.
  13. Don’t underestimate the power of having a plan and setting deadlines. Without them, you risk underestimating real challenges or not taking the risks that could lead to the biggest leaps forward.
  14. Nothing is new and that's okay. It's the journey of seemingly going in circles where we learn and innovate the most.

Here's a look at what the others shared:

With almost 45 years of collective experience, we enjoyed seeing where there was overlap and how we each prioritized different themes.

Whether you're working in an agency or not, I highly suggest this activity. It's a different way of looking back. It makes you realize how everything that has come before has made you who you are today. For me, it reminded me how grateful I am for the past and what it has given me today.

In the words of Keith J. Cunningham in his book, The Road Less Stupid:

"Pleasure is about stimulating the sense. Happiness is found by being grateful for what I've got. Success is getting what I want. Fulfillment is giving what I've got."

I think we'd all be happier with a little more gratitude.

What are the most important lessons you've learned over the past 5 years? How have those lessons changed who you are today?