I wanted to be a great boss and team leader.

I wanted to do something important in the world, not just chase numbers.

I wanted to get the right people around the table.

I didn’t want to be someone sucky to work for.

But it wasn’t working.

I wasn’t looking forward to our meetings. In fact, I was dreading them. The team that was supposed to be my freedom felt like a prison sentence. They misunderstood me, and looking back I now, know I misunderstood them.


Here’s what I tried to make things better:

·       I voraciously studied leadership techniques and pushed the team to make quick, reactionary changes based on current fads.

·       I used our staff meetings to get assurances from the team that they liked me thus glossing over the real issues that needed to be solved. I focused more on impressing the team than impacting them.

·       When stressed, I went to the other extreme and exhibited an intense tone or displeasured expression to get them to act.

I wasn’t safe to work for.

And because people didn’t feel safe they would complain at home about the problems they were afraid to bring up in the meetings.

How could I get in front and stop running from emergency to emergency? How could I stop chasing the next new management fad? How could I be good and effective as a boss? How could I relax myself and my team so we could dig into the real problems and move things forward?


You know what changed?

I met a guy at a leadership development retreat who was like the Obi-Wan of being a good and effective boss. He said something to me that shook me to my core. It woke me up.

People aren’t cattle.

I could easily burn out myself and others because I kept forgetting one reality: We are humans and humans have problems.

I am a human and I have problems.

Team members are humans, therefore they have problems.


Humanity is not an excuse for poor management practices or looking the other way when your team doesn’t execute.


You can be a great boss (one of their favorites) if you truly value them and lead them with clarity.

The Obi-Wan Kenobi I met helped me tap into my ability to be a great boss, it was like the Force. And he described what was happening with such laser clarity that it relaxed me. I immediately implemented his advice and hired him to coach me and consult with our organization.

My Obi-Wan’s consultation, which cost a lot of money, helped me realize I was going into meetings cocked and ready to fire; I was increasing pressure in an effort to motivate everyone. I thought the best arguments would force everyone to move in the same direction at full capacity. I was wrong.

I learned that whenever I was tempted to ramp up intensity I actually needed to increase clarity.


I met my Obi-Wan 15 years ago. The world’s changed a lot since then - what that guy gave me was the boost I needed to navigate a multi-million dollar failure, preserve my most important relationships in the midst of chaos, find my own way in the midst of lots of pressure, and kick off my own career assisting companies from Florida to Finland. I help leaders and companies change so that everyone from the assistant to the head manager, to the CEO is actively growing, participating, and enjoying the process.

This is not about “perfect work,” but healthy cultures with good people. These are the places we make meaning, figure out who we are, and develop our skills.

You can’t storm into meetings demanding performance  and neglect being a good human being and treating others well, or you will lose the coming of age workforce. You can’t flatter them or bribe them into staying in an unhealthy culture. They will leave. And if that makes you uncomfortable or afraid, then you’ll insecurely cling to them and push them away. Even if you feel your team is inhibiting not empowering the change starts with you.

I’ve learned to wake up when I’m reverting to what I now see as a short term tactic: an increase in the intensity of my tone. Instead I need to increase the clarity of the culture I want to build.

“Working with Chris has easily been the best thing I’ve spent my money on all year in terms of ROI. I’m very lucky to have found him so early in my career, but his methodology is important for anyone, in any age or career path. The first few sessions with him will be transformative, and you’re guaranteed to have a few watershed moments. Then you realize that it’s not just about those large revelations, but instead it’s a lifetime of learning and practicing, using his framework for growth. The reason Chris’s work is so important is that it’s fundamental, rather than a trend or quick fix. It’s the distillation of the expertise of hundreds of authors, coaches, and leaders before him, made into a program that’s easily understandable and immediately applicable. Jam with him on books, podcasts, religion, or business problems, and then dive deep into relationships, communication, leadership, management, and growth. Get ready to see yourself differently.”
— Founder/CEO of Death To Stock, David Sherry