Sometimes the Best Thing You Can Do in Leadership is Get Out of the Way

By Dan Kahn

The first time it happened, I was sitting alone in the dark, so mad steam was practically shooting out of my ears. It was January 2021, and I was fried after 10 months of triage, emotional breakdowns and manic 80-hour work weeks. It was all in the name of keeping my small business of two dozen employees working, productive and functional during an unprecedented pandemic and pivot to working from home. My kids had been sent home and forced to try school via Zoom, which didn’t work. My wife desperately attempted to keep her small business afloat while also homeschooling the kids. I was mentally, emotionally and physically tapped out from trying to keep our and our clients’ businesses viable and productive. That’s when the lights literally went out.

The area where we live in Southern California is prone to wildfires. After doing little to no preventative maintenance for a few decades, the local power company’s fire prevention solution was to kill everyone’s power anytime it got windy. That’s what happened that January evening, and I sent my family to stay with my in-laws, who still had power. I sat in the dark, stewing over the state of the world and how difficult simply getting through each day had become. I made a snap decision and called my wife, telling her and the kids to pack their things in the morning because we were hitting the road. The idea was simple: if my team was working remotely and my kids were being home-schooled anyway, why sit around in a dark house with no power waiting for the next obstacle to fall in our path?

We hit the road the next day for what would end up becoming a life-changing trip. Seven weeks, 7,000 miles, nine states, a dozen state parks, and one Texas winter superstorm later, I learned many lessons. First and foremost, we learned about resilience. The kids actually thrived on the road. Homework and lessons were no easy task, especially with everyone packed into our modest 26-foot travel trailer. But we (mostly my incredibly patient wife) got schooling handled. And I learned about myself, my team, my company and the nature of leadership. By the end of that trip, I realized something new. My entire definition of leading people was wrong, and I had a lot of work to do.


Until March 13, 2020, I was under the impression that leadership meant sitting in the trenches with your team and showing them what to do. Then doing it with them and watching as they took every action to ensure they repeated every task the exact way I showed them and maintained my extremely high standards. Success reinforced that notion. Over a dozen years, we grew an average of 20-25% per year. Clients were happy, and the business was healthy. I ran a tight ship and kept a close eye on every manager and employee. My favorite phrase was “Don’t do your best, do MY best,” which was management at its highest form in my mind. I knew how to do every job in the company and was willing to prove it daily if necessary. What a fool I was.

When the pandemic hit, and we had to send everyone home, the first few weeks flew by as my team focused on the processes. How would we connect with managers and teams and keep an eye on workflow, task management and hour burn? We found the same software suites that the rest of the world used and figured it out. I was still scornful and convinced that the only real way to run a team was back in the office, pacing the floor and physically “watching the store.” But things began to change. Some team members thrived in the remote environment while others struggled. The most self-aware employees actually requested a return to the office in a full-time or hybrid format. As is the case with most businesses over the past few years, we experienced a huge wave of turnover with staff leaving for new opportunities. At first, this was cause for consternation. But then we discovered that by opening hiring to a national workforce, we could pull in incredibly bright, experienced people with diverse backgrounds and viewpoints that made us stronger.

Some of this talent was already in place when I hit the road for the first big trip in January 2021. As I worked from picnic tables and the passenger seat of our pickup while we crossed the county, sitting in on Zoom calls and client strategy sessions using a 5G hot spot as a conduit to my business and the world, it dawned on me. I had managed to recruit an incredibly bright, creative, responsible and resourceful group of people, and the thing holding them back was…well…me.

By “managing” these people with the expectation that they needed to perform every task the way I would, I was cloning my best work experience but also my limitations and blind spots. They flourished when I hit the road and let them take on more responsibility. Projects came to fruition smoothly and with creative results. Clients were happy. The monthly reports showcasing our work were packed with results and new ideas. This was my first hint that I needed to stop managing and start leading.

When I returned from the trip, I had to find a new paradigm. It was no longer “do my best.” I made a concerted effort to make it less about me and more about each individual on the team. What did they need to be successful? What could I do for them to make their job easier? How could I help? What roadblocks were they hitting, and how could I help remove them?

This led to more challenging conversations. More people left, and more new employees joined the team. Our ranks swelled past 30, and we hit new financial benchmarks that seemed impossible just a couple of years ago. All that new talent came in with new ideas and lots of questions. Why didn’t we have a formalized onboarding process for clients or employees? Why didn’t we have digital training assets for each position? Why was our SOP (standard operating procedure) a dense, hard-to-read handbook and not a series of videos? All valid questions and great ideas.

We sat down first with the leadership team and then with the entire staff. Instead of just discussing our mission statement or doing a SWOT analysis like we used to, we had a series of candid conversations. We talked about management versus leadership, the company’s future, the future of work, why we exist and what makes people happy. And that’s the key – there is no one size fits all trick to leadership. Every single person on the team is unique. Every person has their own challenges, wants and motivators. What frustrates one person to the point of wanting to quit motivates another person to work twice as hard to find a win.

That’s when I realized that I was doing the wrong job. The CEO should not be in the trenches with the team showing them how to do every task. The role of the CEO is to be the visionary who leads the brand and company, ensures financial stability and listens. Listens to the customers, the industry, the market, and, most importantly, listens to their people. Learn what each person needs and provide systems and processes that allow as many of them to prosper as possible.


Fast forward to today. Once again, I’m working from the road and writing this editorial from the passenger seat of our pickup. Today is Day 31 of the Kahn family’s summer 2022 road trip. We worked our way up the coast to the northern tip of Washington, spent Independence Day on an island a few miles from the Canadian border, and then started heading south. I work while the kids explore, hike and keep notes in their journals. I’ve sat in on client calls, staff meetings and leadership huddles beneath giant coastal redwoods and from sketchy truck stops and Wal-Mart parking lots. We’re finally headed home, and I find myself awestruck every time I sit in on a call and hear my staff coming up with creative new campaigns, cutting-edge social and digital marketing ideas, and programs that, quite frankly, I never would have thought of.

I am no longer the most intelligent guy in the room. Maybe I never was; it was just hubris and hustle culture that made me think that was the case. One of my favorite business podcasts is “21 Hats,” hosted by journalist Loren Feldman. On an episode a few months ago, one of his frequent guests, William Vanderbloemen, who owns a recruiting firm, quipped that he tries to work remotely at least once a year as a “stress test” for the company and a “destress test” for himself. He reasoned that if a decent size company can’t function properly for one month without the founder calling all the shots, there is something seriously wrong with the culture and leadership of that firm. Two years ago, that concept would have horrified me. Today, I think he’s right.

The amount of change my little firm has undergone over the past two years and how much better we are today in terms of both client and employee happiness is shocking. We have employees in seven states, people who work full-time remotely or in the office, and many who split the difference. Pay is higher, benefits are better, people seem happier, and it shows in their work. Our leadership team is taking more ownership than ever before. They work together as a team to ensure all departments are profitable, while I focus my energy on the twin goals of client and employee happiness. All it took was a power outage and a few thousand miles on the road to finally see the light. Funny how life works, isn’t it?