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5 Things You Need To Know To Successfully Manage a Team , With Maynard Webb

“I think the most effective idea that I could share and promote is that we are capable of more than we think we are. I would like to…


“I think the most effective idea that I could share and promote is that we are capable of more than we think we are. I would like to inspire people to dream big — and execute bigger. The companies that are most enduring — Amazon, Apple, GE — frequently step back to reassess their strengths, and are open to a refreshed view of who they are, and what markets their assets and expertise have positioned them to win. In 1998, no one could ever have imagined that a small online bookstore named Amazon would one day be a dominant innovator and in cloud hosting and infrastructure — let alone in in-home voice assistants. If you are willing to dream and then work hard and execute well, you can achieve more than you ever imagined. While there’s no formula, there are individual steps on the path to success that must be followed. It all starts with aiming high. What’s high enough? Imagine yourself on a stage five years in the future telling people what you’ve accomplished. Are they inspired or unimpressed? You always want to leave them amazed. If what you are thinking is not amazing enough, think bigger. Reflecting back on where we started, no one ever spoke to me about applying for scholarships or aiming to go to college. No one expected that I could be better than good — and that I could hustle my way to great. No one told me that there was such a thing as a breakout. I was only told that I would have to take care of myself when I graduated high school. That curtailed the possibilities. While both of my parents went to college, I was the first of my siblings to get a degree. For all of us, the options felt limited. I wish we knew then that the options were boundless. I wish I knew that we could create opportunities for ourselves, that jobs could be exciting and fulfilling — and that we each have a role in building an extraordinary life. We are all the CEOs of our own destinies. And what an opportunity that is for building a beautiful life and a better world.”


I had the pleasure of interviewing Maynard Webb, an investor in startups through the Webb Investment Network, which he founded. He is a cofounder and board member of Everwise, a mentorship startup, and a board member of Visa and Salesforce. Previously he served as Chairman of the Board of Yahoo!, CEO of LiveOps, and COO of eBay. His latest book, “Dear Founder: Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business,” was published in September 2018 by St. Martin’s Press.

Thank you so much for doing this with us! What is your “backstory”?

I had an unconventional childhood that was incongruous with the life I live today. My father died unexpectedly when I was seven years old. He didn’t have life insurance, and my mom had to go back to work to support five kids. We lived without an air conditioner, hot water, and TV — and we also lost the opportunity to dream about what could be as we were too caught up trying to get by. Things weren’t easy in school, either. When I was in elementary school, people thought I had a speech problem and that I should be in special education. They wouldn’t let me enroll in Cub Scouts if Mom didn’t serve as a “den mother” — something she couldn’t do because she worked. Since the football program cost money to join, I couldn’t play on an organized team until junior high, when it was free. Always, I was the kid without a father, and without any money.

Still, I had big dreams, and I worked hard and saw the results of doing so. I won awards in school, loved sports and was an MVP in Little League. I thought I was going to play in the major leagues. My mom was so worried that my head would get too big, she sarcastically called me “hero” as a way keep my ego in check.

I’ve worked my whole life — so many odd jobs! A paper route, delivering mattresses, cleaning toilets at Mr. Donut (this is the only job I ever got fired from…I ate too many donuts.) I got into the Naval Academy at Annapolis but didn’t go (my mother wanted to kill me) and after getting a degree in criminal justice from Florida Atlantic University, I started my career working as a security guard at IBM. I didn’t know what the future held, and truthfully, I had no idea how amazing my future could be. My biggest dream at that time was to become an IBM manager and own a home.

I always believed I was capable of achieving anything, I just didn’t think the world would let me, given my background and some of the choices I made. I think I understood that I always had to better myself, and I knew I could, but I doubted whether the system would see my unique capabilities as I took a very nontraditional route. I was, in the words of one executive who mentored me, “an acquired taste.”


Can you share the most interesting story that happened to you since you started your career?

My team and I see hundreds of investment opportunities a year. I always love hearing the back stories of the entrepreneurs and also learning about their businesses. We ask a lot of questions as we end up investing in only a fraction of the companies we see.

There was one CEO, who had barely started his company and it was a high-risk marketplace idea with only a handful of participants. I asked the CEO, what his biggest challenges were. He said, “None. I don’t see any until our revenue is north of $1B!”.

Building a business is as hard as catching lightning in a bottle! This wasn’t comforting!

How do you synchronize large teams to effectively work together?

Such a good question! This is the process I use when working with a large team, and also when working with different teams that have to work together — but may not always want to, yielding what I call cross-functional friction.

  1. Get alignment on goals. I’m a fan of ensuring that everyone gets input on one another’s goals and on grading these goals later on. This also includes knowing what trumps what, and which goals matter most. When I first joined eBay, I had the head of development focused on shipping fast and furiously, and I had the head of operations focused on availability. Needless to say, there was a lot of head-butting between the organizations. To resolve the strife, I had to intervene and decide what goal was most important. Eventually, I changed the goals of each team so that ops shared the delivery goals and product development shared the availability goals. When I added customer support to my team, we realized that we needed to add customer satisfaction to all the goals as well. Everything works much more smoothly — and pleasantly — when everyone is working toward the same goals.
  2. Engage in broad communication. Communication must be constant, and it must reach everyone. Marissa Mayer at Yahoo did an “FYI” for all employees every Friday. Yahoo has had it struggles and challenges, but Marissa’s willingness to stand up and face tough questions every week was a source of inspiration and calm for the company.
  3. Implement decision-making guidelines. I’m a fan of the RACI model (who is Responsible, who needs to Approve, who needs to be Consulted, and who needs to be Informed), but there are a number of methods you can use. What’s most important is that you pick one and diligently stick to it.
  4. Find ways to surface issues. I ask everyone at WIN to submit things they need help on every week. In my 1:1s, I ask how things are going and why.
  5. Celebrate the wins and give validation to incent people. When you see behavior that is great, call it out and celebrate it. Our customer support team at eBay gave out “silver star awards” to those people who went above and beyond to help them out. There were lots of people at eBay who had the printed award up in their cube.

What is the top challenge when managing global teams in different geographical locations? Can you give an example or story?

  1. Often the biggest challenge is being able to handle the time zone differences and communication difficulties. I have faced this several times in my career.
  2. How to handle? I would try to ensure that I religiously did 1:1s and during a time that worked well for the other party. When I had staff meetings with people in different regions, we varied the time so that everyone shared in the inconvenience. Also, we did our best to get face-to-face at least quarterly, which helped tremendously.


What advice would you give to other CEOs or founders to help their employees to thrive?

  1. Treat people with respect and dignity always and promote a culture of inclusion. Do not allow a monoculture, such as a “bro culture” — this is antiquated and dangerous. Have a workplace that supports and celebrates diversity and makes everyone feel comfortable.
  2. Spend time engaging with people. Say hello to people in the morning and good-bye at night. Be approachable. Ask about their families and show them you care about things other than them getting their work done. When they miss work because their baby is sick, ask about how the child is doing when they come back. Also, enable your teams to enjoy and get to know each other. One great and very simple way to do this is through team lunches and dinners.
  3. Treat setbacks as learning experiences. If there are problems, address them candidly and openly. Let people ask questions, and then enlist their support to fix things.
  4. Honor special occasions. Acknowledge special occasions such as anniversary dates. IBM used to give a gold watch to celebrate twenty-five years with the company, but most people don’t stay so long with the same company anymore. You don’t have to wait twenty-five years! You can celebrate every year, and other milestone anniversaries, in small ways by recognizing people’s achievements in all-hands meetings, by writing them thank-you notes, or by planting balloons at their desks.
  5. Celebrate success. Do fun things with your team. Take a break to treat your team to a movie or do some charity work together. It can be simple: At LiveOps, we had random Nerf arrow attacks and paper airplane contests; at AdMob and Everwise, the sales team rang a gong when a big deal was done. It’s especially important to do this when times are hard.
  6. Extend inclusion beyond your employees. People work hard, and their families miss them when they’re away — you need support from their families, too. Include them in special events. At eBay, Meg took every vice president and above away for a weekend with their families. Being able to share an experience together resonated greatly with employees and their families.
  7. Use philanthropy to give additional purpose to work and use philanthropy to unite the company. Give people time off to volunteer. Consider doing team-building exercises around helping a favorite charity.

Most times when people quit their jobs they actually “quit their managers”. What are your thoughts on retaining talent today?

You are so right, and that is such a shame. You want people to stay with you and if they quit it should be because they are following their destiny to do something different — not to get away from their boss.

There’s no entitlement for employees anymore, and there’s no entitlement for companies. I think that you have to make your company attractive by being the best place to work. Be the place people are clamoring to join. Being the best place to work is not about massages and gourmet food; it’s about what was accomplished, what was learned, and how well people are treated. My other top three pieces of advice:

Have huge aspirations. Be inspirational with what you are trying to accomplish.

Be humble. Never stop trying to get better.

Be fun to hang with. Care about your people. Treat anyone you bring on like a family member. When former employees look back on their career, you want them to think that yours was the best and most fulfilling job that they ever had. That’s never about money; it’s about being a part of something meaningful.

Based on your personal experience, what are the “5 Things You Need To Know To Successfully Manage a Team”. (Please share a story or example for each, Ideally an example from your experience)

  1. Praise in public; criticize in private. Always follow this rule. It’s not just what you say, but how you say it and how you hold yourself. I learned this early in my career when I worked for a screamer. It led to a toxic environment, which was not fun for anyone.
  2. Say what you do and do what you say. I am always a fan of acting with credibility and building trust. Whether it’s with your customers, employees, board or investors, you will find that everything goes much better when you deliver consistently. And if you don’t do that, you leave yourself exposed — don’t be surprised if people take advantage of that. At eBay, we put up an announcement whenever we had a significant issue and that transparency, while painful, led to far better trust with our community and eventually, far better results.
  3. Personally model enthusiasm — even when it’s difficult. At eBay, some days were hard, and even without saying a word, people could tell that I was troubled by something. They got worried and asked what was wrong. I would say, “Wow, just because I wasn’t smiling you think I’m angry, or someone is in trouble.” However, I had to accept that my actions were leading them to worry. I had to maintain more of a sense of calm, even in an urgent situation. I learned that from Meg Whitman’s leadership. She made me laugh every day, and these interactions helped me get through the clutter. As a leader, you need to model courage, candor, and resolve.
  4. Guide your people and work with them so they can do their magic. You can get much more done if you are leading them to greatness rather than babysitting or micromanaging them. When you see people hit that stride give them more to do. Grow and challenge them constantly. When one looks back on their career, it is often the difficult things we did that we find most satisfying.
  5. Don’t settle. The natural tendency is to slide into average. Everybody thinks they are a good manager, but ask their employees and you’ll hear a different story. Be critical of how you are doing — and continually strive to be better. I would always ask my teams, “Who is the best in the world at this? And, if it’s not us, what do we need to do to get there?”

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Thank you. I think the most effective idea that I could share and promote is that we are capable of more than we think we are. I would like to inspire people to dream big — and execute bigger.

The companies that are most enduring — Amazon, Apple, GE — frequently step back to reassess their strengths, and are open to a refreshed view of who they are, and what markets their assets and expertise have positioned them to win. In 1998, no one could ever have imagined that a small online bookstore named Amazon would one day be a dominant innovator and in cloud hosting and infrastructure — let alone in in-home voice assistants. If you are willing to dream and then work hard and execute well, you can achieve more than you ever imagined.

While there’s no formula, there are individual steps on the path to success that must be followed. It all starts with aiming high. What’s high enough? Imagine yourself on a stage five years in the future telling people what you’ve accomplished. Are they inspired or unimpressed? You always want to leave them amazed. If what you are thinking is not amazing enough, think bigger.

Reflecting back on where we started, no one ever spoke to me about applying for scholarships or aiming to go to college. No one expected that I could be better than good — and that I could hustle my way to great. No one told me that there was such a thing as a breakout. I was only told that I would have to take care of myself when I graduated high school. That curtailed the possibilities. While both of my parents went to college, I was the first of my siblings to get a degree. For all of us, the options felt limited. I wish we knew then that the options were boundless. I wish I knew that we could create opportunities for ourselves, that jobs could be exciting and fulfilling — and that we each have a role in building an extraordinary life.

We are all the CEOs of our own destinies. And what an opportunity that is for building a beautiful life and a better world.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My personal motto is, “I’m just a lineman.”

When I was recruited to Bay Networks as the CIO, the CEO asked me what does he really get when he hires me. I told him that I was the shortest and slowest lineman on my high school football team, but that when it was 4th and 1, we almost always ran over my hole and got the first down.

Originally published at medium.com

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