9 Leadership Lessons From the Greatest Boss I Ever Had

Ryan Estis
February 25, 2020

Ryan Estis

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Ryan Estis – CEO | Keynote Speaker | Sales & Leadership

I walked into the restaurant 5 minutes early for our 6:30 p.m. reservation. He was waiting to greet me by the bar. He was always 5 minutes early.

This one was just one of the many habits this extraordinary man gifted to me. Working for him was a life-changing experience, and many of the lessons I learned from him are foundational principles I still practice today. 

The best leaders are acutely aware of the impact they have on people and recognize that leadership is about helping people become their very best. Leadership isn’t a job. Leadership is a responsibility.

What makes a leader extraordinary? Here are the leadership lessons from the best boss I ever had.

Always Have a Vision

My boss was always thinking about the future. He could clearly articulate where we were going and how we were going to get there. His confidence and optimism about our future success were contagious. I would constantly leverage his vision as a source of inspiration for our sales organization. I still miss his Good News Friday weekly update.

Be Present With Your Presence

He put in the work. Trade shows. Client presentations. Office visits. His impact was felt daily throughout the organization, and he was always willing to give more. A phone call to an employee who delivered a big win for a customer or our team. A handwritten note to welcome a new client. A lunch and learn with the team during an office visit. He cared about the culture of the organization he was leading, and he worked tirelessly to continue making it our competitive advantage.

Position People for Spectacular Success

I always felt like my boss was committed to helping me reach my true potential. He would work with me to eliminate barriers that might inhibit our success. He created opportunities for me to contribute more to the business. I felt empowered in my work. He was generous with recognition when it was warranted. There was an incredible sense of pride and belonging in our organization among the top performers.

Invest in Your People

He was a catalyst for my continued learning and development. What he couldn't offer, he encouraged me to seek out on my own. He was always interested in my future, and he made sure we were in alignment with support of my goals. He is one of the best listeners I have ever known, but he didn't stop there. He would follow up and follow through. He never made promises he didn't keep and the conversations that led to commitment were always supported by action. Always.

Develop Authentic Friendships

His investment in me went way beyond the office. It was clear that he cared about me as a person. I will never forget the time he invited me to spend Thanksgiving with his family. The friendship transcended business and served to reinforce my commitment to him. How do you think I responded if he needed a little extra from me to close out the quarter?

Hold People Accountable for Underperformance

Our friendship never interfered with the obligation to the business. He was very clear in his performance expectations and candidly, consistently evaluated my contributions. His clarity meant that I always knew exactly what was expected of me. If I couldn't deliver my sales number, he was obligated to find a sales executive with the talent to hit the performance target. That wasn't personal. That was the job and I respected that deeply. I also didn't miss that number.

Respect Conflicting Opinions

We didn't always agree, but I always felt that he was open to my perspective. As I matured in my role, I would confidently express my opinion.  Occasionally I could be aggressive in taking an opposing view on critical business decisions. I think he enjoyed the debate and defending his own position with conviction. It was also clear that he wanted my full commitment to the final decision, even if I didn’t win the argument

Admit When You're Wrong

His unique blend of confidence and humility brought him support in times of adversity and challenge. He made mistakes. We all do. He could admit when he was wrong. Being open about our missteps was critical to correcting them and building a better business over the long term. We'd all make them and learn and grow together as a result. He was a truly collaborative leader.

Go All In

He led by example, and it was abundantly clear to everyone that the business was his life's work. His commitment to success was less about him and very much about creating something unique, special and sustainable for the people who were investing their time and talent into the organization. Yes, he wanted to win. I believe he wanted to win more in the service of others than for what it meant to him personally. His selfless approach to leadership earned an incredibly loyal following and is the primary reason I stayed with the organization for much longer than I had ever planned. I wanted to work for him.

May we all lead with that kind of impact.


Ryan Estis has more than 20 years of experience as a top-performing sales professional and leader. As the former chief strategy officer for the McCann Worldgroup advertising agency NAS, he brings a fresh perspective to business events. As a keynote speaker, Ryan is known for his innovative ideas on leading change, improving sales effectiveness and preparing for the future of work. To book Ryan Estis for your event, visit https://premierespeakers.com/ryan-estis

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9 Leadership Lessons From the Greatest Boss I Ever Had
Ryan Estis
Ryan Estis
February 25, 2020
Ryan Estis - CEO | Keynote Speaker |Sales & Leadership I walked into the ...
9 Leadership Lessons From the Greatest Boss I Ever Had
Ryan Estis - CEO | Keynote Speaker |Sales & Leadership I walked into the restaurant 5 minutes early for our 6:30 p.m. reservation. He was waiting to greet me by the bar. He was always 5 minutes early. This one was just one of the many habits this extraordinary man gifted to me. Working for him was a life-changing experience, and many o...
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