What I’ve Learned from My Best Managers

How to reach new heights in your career

Photo by Markus Spiske on Unsplash

I have been blessed to have many managers who were transformational to my career. They believed in me, sponsored me, and helped me grow. They challenged me, gave me hard feedback, and transformed my thinking. Each of them was a powerful catalyst that helped me get to where I am today. 

This article is dedicated to them, and to everything I’ve learned from them over the past 20 years. Here are some of the most important things they taught me:

Knowing that someone has faith in your potential is a powerful tool 

One of the best managers I ever worked with gave me a vision for what my future could look like. He laid out a roadmap of how I could succeed, and then he helped me get there. I wanted to live up to the potential he saw in me, and his faith in me encouraged me to work harder and reach for more than I could have ever imagined.

That is what a great manager does. They not only work with you on your path today, but they also help you see where you can go in the future—even if that journey takes you far away from them.

That faith is something to live up to. I once had a peer whose philosophy was that the people on her team had to earn her respect through excellent work and consistent results. I felt differently. I work under the notion that you should always have faith in someone so they are motivated to show you their best. 

Most people thrive with the wind at their backs and the encouragement of those around them. The best managers give their reports a reason to want to make them proud.

Sincere praise goes a long way 

One of the most powerful forces in a relationship is praise. Knowing that someone appreciates your work and openly thanks you for it helps you discover what your superpower is. It teaches you what is special about you—and how to use it to achieve great things.

I still remember some of the most impactful praise I received from early managers. One said to me that I made complex things simple. I had never thought of myself like that. Another said that I made everyone feel included in the process, which led me to spend a lot of my time ensuring I lived up to that on my teams. Yet another said that my investment in dogfooding made our products better. I ended up becoming an avid dogfooder throughout my career. 

A great manager praises in public and corrects in private. They speak about your accomplishments when you are not around to ensure they are amplifying your impact. That level of support and encouragement allows you to fine-tune your skills and evolve your career in the right direction.

Feedback is a gift 

A great manager isn’t just someone who supports; they are also someone who helps you succeed by giving you hard truths. My toughest feedback came from my best managers. People who care about your growth invest in making you the best version of yourself that you can be. They push you to be more, and they give you the tools you need to get there. 

My best managers took the time to gather feedback and share it with me consistently. They were thoughtful and careful to invest time to walk me through my blindspots and taught me how to proactively address them. One told me that I didn't have an eye for design, so I read books and taught myself Photoshop and Balsamiq to understand the complexities of UI. Another said that I needed to be less partisan in how I led and fight for my product and team less. So I worked to adjust my style. Yet another said I needed to simplify my communication and get less into the weeds. So I worked to improve. 

They put your long-term success first

Managers who support you don’t just do so because you are on their team. They are your mentors and sponsors for life. When I considered leaving eBay for Facebook, each of my managers, both former and current—Mauria Finley, Greg Fant, Stephanie Tilenius, and Amy Klement—encouraged me to take the risk and go, even knowing that they wanted to keep me on their teams. They saw in me the potential to do something more, and they supported me, even though they knew it meant no longer working together. 

Because of their influence, I have sent people on my own teams to new roles with the same blessing. If they find something new they want to explore, I support them. I also make a point to tell them that if things don’t work out, they are always welcome back if we can find them a good spot. There have been many people who did come back around, and we’ve been able to work together again at a different time and in a different place. 

Supporting your reports is about allowing them to take on new challenges, even if that means you will no longer directly benefit from their contributions. The best managers understand this, and will encourage their team members to spread their wings. 

Stretching is the best way to learn and grow 

The best managers see the potential in you and encourage you to take on stretch assignments—even when you aren’t sure you’re qualified to do it. While this can be intimidating, it allows you to learn new things and develop new skills.

I’ve had many managers who gave me a chance to do a job that I should never have had the right to do. In doing so, they gave me the chance to grow in ways I could not have otherwise imagined for myself. 

When I was made a manager for the first time, I had been a product manager for less than two years. When I took over the whole team as Director of the eBay product at PayPal, I had been doing the job for less than four years. I learned on the job (apologies to my poor team, who were my guinea pigs!), and I grew so much as a result. 

My manager took a risk on me. It could have gone either way for her, but she did it anyway. Now, I look for opportunities to do what she did: to help people grow their scope and learn new skills over time. 

You are more than your work  

It can be easy to forget at times, but your job is only one facet of your life. That’s why it’s important to have a manager who understands this and supports you beyond just the scope of your job. 

My best managers were the ones who cared about me personally, not just peripherally. They saw my work as a part of my life, not as my whole life. They supported me in ways that went beyond the job. I still remember when my manager told me I didn't have to do it alone. I had been struggling with a baby who had trouble nursing and a father who was in hospice. My manager gave me the courage to look at my life and ask for help. I couldn't have done that without his support at a very vulnerable time in my life. 

That's what great managers do. They see you as a whole person, are mindful of the challenges you face, and support you no matter what.

Trust is built through consistency and lost through broken promises

I had a manager who really cared about me, and he demonstrated it through transparency and consistency. I had not been promoted in many years, and I had taken a lateral move. He couldn't promise me anything, but I knew he was fighting for me. I remember when he called to tell me that I had been promoted, but that they had to hold it because the company was doing well at the time. He was completely transparent about the entire process, and I never once felt like he let me down—even though it was painful to get the message. 

Great managers build trust over a long period of time. They don't promise things that can't be done. They focus on the long-term relationship, not just keeping you happy in the short term. This reduces resentment, builds trust, and allows for honest, open dialogue when challenges emerge.

We live up to—and live down to—expectations

I always worked hardest and gave my best to the managers whom I respected most. They were able to bring the best out in their teams because they held us to a high standard. They asked for more and got more. 

The managers who pushed me the hardest got the most. They knew how to challenge me and awaken my desire to do my best. Some of them were really difficult to work with, but my respect for them strengthened our relationship and helped me grow.

Andrew “Boz” Bosworth was one of those managers. (I write about my relationship with him in one of the chapters of my book.) Though we didn't start out on the right foot, he challenged me to think differently and work differently. He taught me that I had something to say, and that I should learn to write. In many ways, his encouragement was what led to my book, and to this newsletter. 

That is what a great manager does: they set a high bar and challenge you to surpass it. They believe in you even when you don’t believe in yourself, and that belief is what helps you learn and grow. 

They remain in your life after you part ways

Some of the best managers I’ve ever had still keep in touch with me to this day. They remain mentors or advisors, even many years after we worked together. Our relationship is not temporal or work-based. It is a long-term partnership where I feel like I can call on any of them at any moment. In fact, when I was considering taking my current job, I got in touch with many of my previous managers to get their advice. 

That is the beauty of a great manager: the relationship never ends. It changes and evolves as you change and evolve—in both your career and theirs. 

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If you read this list and you feel like you've never had a manager with these traits, then you’re really missing out. One of the most important things you can do to accelerate your career is to find somebody who has your back and is willing to fight for you, teach you, and open doors for you. If you haven't found that yet, seek it out. Challenge your manager to challenge you. Ask for more feedback, and show your eagerness for growth. This is how you will reach new heights in your career.