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Busy Burr of Carrot: “Pick your boss not your job”

There will be times when your career really sucks. Maybe you get laid off, maybe you can’t find a job, maybe your business idea doesn’t get off the ground, maybe your boss is bad — like really bad. Jobs, work life can really suck. There are setbacks. Everyone has them. Don’t believe all the happy, perfect stories. […]

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There will be times when your career really sucks. Maybe you get laid off, maybe you can’t find a job, maybe your business idea doesn’t get off the ground, maybe your boss is bad — like really bad. Jobs, work life can really suck. There are setbacks. Everyone has them. Don’t believe all the happy, perfect stories. Know that change will come and be persistent, say yes to new opportunities as much as you can.


As a part of our series about strong women leaders, we had the pleasure of interviewing Busy Burr, President and CCO at Carrot.

Busy Burr is a cross-industry executive who has made a career creating innovation strategy and operationalizing commercial initiatives in some of the largest, most complex organizations in the world with functional roles spanning finance, marketing and operations. At Carrot she leads the team focused on bringing the company’s digital health solutions to market.

Prior to Carrot, Busy served as Vice President and Chief Innovation Officer at Humana, a 40 billion dollars US healthcare company. In this role, she led a 60+ person team driving the design, build, and adoption of new product platforms in digital health, provider experience, care in the home, and telemedicine.

Before joining Humana in 2015, Busy held leadership positions at Citi Ventures, Gap and eBay, and spent seven years in investment banking at Morgan Stanley and Credit Suisse First Boston, executing IPOs and M&As for companies in the technology space.

Busy is a sought-after speaker and collaborator, and a long-time performing member of the Bay Area improv troupe ‘Subject to Change’. She holds an MBA from Stanford and a BA in Economics from Smith College and sits on the Board of Directors of Rite Aid and Mr. Cooper. She was named one of Silicon Valley’s Women of Influence and has been honored as Frost & Sullivan’s Innovator of the Year.


Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I was born and raised in Massachusetts and came to California for what I thought was going to be 2 years at Stanford for my MBA, but I graduated into Silicon Valley in the ’80s which was just getting going, so I stayed.

I shun the expression ‘career path’ because it implies something linear. I think of my life more as a collection of amazing experiences: I’ve been a Wall Street financier, restaurant cashier, filmmaker, caregiver, CEO, receptionist, global brand manager, researcher, venture capitalist, camp counselor, board member and now President and Chief Commercial Officer at Carrot and a Board Member of two public companies. All of the experiences I’ve had over the many years of my career contribute to everything I do today. I have a lot of arrows in my quiver.

Can you share the most interesting story that happened to you since you began leading your company?

Most interesting? That’s hard. Here’s a good story: I was struggling to make a decision between two amazing opportunities that I had — going back and forth — writing pros and cons. After sleeping on it and meditating on it, I still couldn’t decide and I was so stressed out. I was having coffee with a good friend (who also happens to be an executive coach) and I told her I couldn’t land on what to do — I expected some brilliant insight that would open it right up. And you know what she said? She said, “It doesn’t matter.” Excuse me?!? This is my career we’re talking about! She said it again, “It doesn’t matter- it really doesn’t.” She said everything will be fine no matter which one you do. So it doesn’t matter. It just doesn’t matter. At first, I thought that was so lame. But ever since that day — I realize how brilliant that was — that I have agency in how I experience what I do. It really doesn’t matter. Just pick one and move on.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I have always been a bit of a prankster at work and occasionally like to send around fake memos and emails to people for fun. Long ago I worked at a huge, global investment bank that hires a lot of smart, fresh out of college, financial analysts — most of them Ivy League and all expecting to be the next big Wall Street barons. One year, I sent around a fake email that over the holidays they would each need to take shifts covering the reception desk so our awesome receptionist could take a break. They were indignant, so indignant, that one of them sent the email to the Wall Street Journal to put in the “Heard on the Street” column. The WSJ called the Global Head of Communications and the firestorm went from there. Not pretty. Thankfully, it didn’t end up running in the WSJ. Has it kept me from messing with people at work? Not really, I’m just more careful about email.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am grateful to so many people — especially my women friends and colleagues — we’ve seen it all. But if I had to pick one person I’d have to say, my wife. She and I have been through so many twists and turns with our careers and in raising our two amazing sons. She knows me better than anyone and is my #1 cheerleader when things seem dark and impossible, and I like to believe I’m her #1 cheerleader as well. We were both on Wall Street in the ’80s (don’t even get me started) and it was not easy for women but there’s been so much change, it’s really remarkable.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

Oh my, so funny. When I worked at Citigroup on the Ventures team, the senior leadership team of Citi Ventures was all women and we used to get together and do the Amy Cuddy / Wonder Woman power pose before big meetings — for fun, for focus, and just well, maybe it’ll work? But more seriously, I read a little Brene Brown. I highly recommend it.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

This should be such a “duh” by now. We are in the innovation age, change is rapid and ideas are currency. Creativity is king. Innovation and creativity are a result of thinking broadly, of seeing what isn’t seen, of exploiting what others are missing. Diversity is the vital force, it delivers the creative energy that drives innovation. And while Silicon Valley companies are just now getting the memo about race and gender equality — there is something about this area, this community of people. Almost everyone who lives here is a transplant from somewhere else — people grew up in Ohio, Texas, Maine, Montana, Canada, Korea, India, Germany, you name it. I’m convinced that the diversity in Silicon Valley is a major factor in its innovation engine.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

We all need to start with being conscious. Recognizing that if we aren’t solving the problem, we are part of it. And that there is in fact a problem. A big one. People of color in this country face a far more difficult journey to achieve their dreams than I do, and the barriers they have to deal with are systemic and often unconscious. We’ve just had 4 years of a President who unleashed a tide of racism and white supremacy. The bizarre upside of that is that there are many more important conversations taking place, but we have a long way to go. We have to stop expecting people of color to solve it by themselves. This is an American problem, not a Black problem, Native American problem or Latino problem. If we fix it, we fix it for all of us — life, community, work, the economy — everything about American life will be better. I firmly believe this. This isn’t zero-sum. All boats will rise. I sit on a couple of public company boards and that’s one place to start, for Boards of Directors to hold management teams accountable for digging and understanding the way merit and promotion are handled in a company. It’s not enough to just report the numbers, instead, we need to demand a deep look at company culture — what are the informal networks and behaviors that support the status quo. Discuss this at the board level and hold management teams accountable for real change.

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

I’m actually a member of an improv troupe and have been for over 10 years. I’ve learned a lot from doing improv and it’s influenced how I think about leadership. Improv is a creative art form — you create a story in real-time, in front of an audience — there’s no script so you’re figuring things out on your feet. The most important elements of improv are about listening intently, paying attention and focusing on making your scene partners look good (and they’re doing the same for you). Improv is incredibly selfless. You have to trust yourself and your team and face your fear of failure every time you’re on stage. So, what does this have to do with leadership? The more senior you get in an organization, the more your job is about listening, connecting people, connecting ideas and making your team successful. The more senior you are the more you have to observe and see how the whole system works. It’s messy, there are massive unknowns, conflicts, failures and successes and you have to navigate through it all — making complex decisions on your feet along the way.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

I think there’s a myth that senior executives have this magical intel that will answer all of the unknowns that people need to do their jobs but they just don’t share it. In a smaller startup, this isn’t such a big deal because there aren’t as many layers, information is shared pretty freely and everyone lives in unknowns. When I’ve been in leadership roles at large, global corporations, there’s this feeling that things are complex and uncertain because those of us in leadership are somehow holding back on our strategic brilliance. The reality is the senior executives do not have all of the answers and we rely on the answers coming up from our teams.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

There has been so much change since I was starting out in my career, but I still think women have to navigate a complex way of communicating — we can’t be too pushy, we can’t be too soft. Men just don’t have to think about this stuff but women do all the time. We have to talk tough but with a smile on our face. Women of color have an especially significant challenge. I also think we have to spend way more time on how we look than men do. Our gray hair, our weight — they all factor into how we are judged in the workplace. For men? Not so much.

What is the most striking difference between your actual job and how you thought the job would be?

I think the most remarkable life change happens to people when they quit smoking. At Carrot, I have been moved by hearing so many inspiring stories of our users who’ve quit smoking. I think I always thought about smoking as a health thing — and it is. But for people who quit, it’s disentangling. They have spent years — I mean YEARS everyday preoccupied with when they’re going to have their next cigarette and where they will need to be. When that goes away it is remarkable the space that opens up — they spend focused time playing Legos with their children. Their child falls asleep on their chest for the first time ever — because they don’t have to go anywhere. It is live changing when someone quits smoking.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

I’m not sure I agree with you actually. I think the mythology that someone is “cut out” or sort of “born” to be an executive has been part of what has kept us back. I remember when I worked on Wall Street out of college, there were a handful of women in my department and the head of the department — a pretty famous Wall Street guy — said to my face, “Women don’t belong in mergers and acquisitions because a CEO would never trust his company’s strategy to a woman.” True story. I think people start small companies because they see a problem they want to solve and before they know it, they are a CEO. I would advise people not to aspire to be an executive but rather aspire to achieve mastery, find things that you can learn — learn constantly — and you will be called on to lead others.

What advice would you give to other women leaders to help their team to thrive?

I learned from Lisa Salamone who I worked with at Gap, to trust my team members to do the right thing and to be there to catch them when they made inevitable mistakes. Micromanaging to prevent mistakes results in a team that doesn’t feel trusted and worse, a team that isn’t learning from painful mistakes.

How have you used your success to make the world a better place?

Hopefully in two ways. First, I see myself as a heart-centered leader — I lead with empathy and trust. We spend a zillion hours in our lives working and I have the privilege of leading and influencing people at different stages in their career. I like to believe that people who have worked for me over the years have learned a lot and have felt challenged and supported and I like to believe that they have become heart-centered leaders as well.

The second way is by being out about my life, my wife and my kids. I think that has made a difference over the years.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. “It doesn’t matter” — see the story from question #2
  2. Life is short but your career is long — there are so many different things you can do. Don’t ever feel like you are stuck. You aren’t.
  3. Pick your boss not your job.
  4. A career doesn’t have to be a linear ascension.
  5. There will be times when your career really sucks. Maybe you get laid off, maybe you can’t find a job, maybe your business idea doesn’t get off the ground, maybe your boss is bad — like really bad. Jobs, work-life can really suck. There are setbacks. Everyone has them. Don’t believe all the happy, perfect stories. Know that change will come and be persistent, say yes to new opportunities as much as you can.

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

As my parents aged, their friends moved away to warmer climates or to live closer to their children. Their social circle got smaller and smaller and many friends were heard from just once a year with a Christmas card. After my Dad died, I noticed how isolated my Mom was becoming. On her 80th birthday, I spent weeks tracking down old friends, buddies from college, neighbors, you name it and had them call her on her birthday. The phone rang off the hook and every call was so amazing. It was such a great day for her. I think we should all do this as a gift for people, especially if they have become isolated. Think how amazing it would be if we took the time to help reconnect people who long to be reconnected.

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

I love the Lucille Ball quote, “I’m not funny, what I am is brave.” Her fearlessness is what made her so successful. A couple of years ago I was asked to give a lecture on taking risks at my alma mater. I’m not sure I had ever really reflected on how being brave was part of my life journey but I think it has been. There have been chapters where I was focused on security, on staying in place and those are the times when the rug was pulled out from under me. When I embraced the reality that my life will be full of the unexpected, then I started to have more confidence and bravery. Boldness drives change, resilience and living without regret.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

Deb Haaland. What a moment to finally have a Native American poised to be Secretary of the Interior. My great-grandfather was an attorney and served as deputy secretary of the Interior at the turn of the last century. He and his family moved from Massachusetts to live in Oklahoma, working with many of the tribal leaders there — as I understand — to represent Native tribes in their efforts to retain their land (though I imagine there is likely more to the family folklore). Our land is filled with such natural beauty and we are so lucky to have so much of it protected. To have a Native American take on this official stewardship role is groundbreaking. I want to meet her and hear her story.

Thank you for these fantastic insights. We wish you only continued success in your great work!

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