9 Leadership Lessons From the Best Boss I Ever Had

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

As we slid into the corner booth, it certainly felt like old times. After working together for more than a decade, we had enjoyed some great dinner conversations and it was good to reconnect. He had been a mentor, a friend and hands-down the best boss I ever had.

Dinner with him was always a special occasion, and I would usually reflect upon the evening long after it ended. The big insight might come in a brief moment, but it was always included. Many of the lessons I learned from him are foundational principles I still practice today. Working for him was a life-changing experience.

If you have ever worked for an extraordinary leader, I’m sure you can relate. 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

The best boss I ever had was future-directed. He could clearly articulate where we were going and how we were going to get there. His confidence and optimism about our future success was 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 made a big contribution. 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 company he was leading and worked tirelessly to continue making it our competitive advantage.

Place People in A Position To Succeed

He wanted to understand how he could help me succeed. He would work with me to eliminate barriers that might inhibit our success. He created opportunities to help me contribute more to the business. I felt empowered in my work and was afforded the autonomy to make my own meaningful contribution and imprint on the business.

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 made sure we were in alignment in 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. The best boss I ever had cared about me as a person and helped me understand that a life lived well was more about what happened outside of the office than what happened from 9-5.

I will never forget the time he invited me to spend Thanksgiving with his family. I doubt he remembered since it happened in a quick, casual telephone conversation without any preemptive thought or planning, but I didn’t forget. The friendship transcended business and served to reinforce my commitment to him as my CEO. 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 align and he was very open to my perspective. As I matured in my role, I would confidently express my opinion, and occasionally I could be aggressive in taking an opposing view on critical business decisions. I actually think he enjoyed the debate and defending his own position with conviction.

It was also clear that he wanted my unequivocal support of key decisions, even if the decisions weren’t consistent with my opinion (as long as they were consistent with my values).

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 inviting more ideas and building a better business. Nobody was on the chopping block for making a mistake. We’d all make them and learn and grow together as a result. He was a true 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.

The phone call offering my resignation was one of the toughest calls I ever made. I didn’t want to disappoint him, but it was my time. We’d circled around this a couple of times in the past. I was tempted by an offer or two on our journey together and he always made a strong enough case to convince me to stay.

However, the last time was different. He acknowledged my readiness and the time was right. Leaders don’t hold people back. Great bosses prepare them for what is next in work and life. I wouldn’t be where I am today without his contribution.

Next time dinner is on me.

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