Unlocking Your Unique Potential With Cara Shortsleeve


You might be skilled to do a ton of different things, but have you asked yourself what's going to make you the happiest? What is the role you’re supposed to play in the world? Cara Shortsleeve had her dream job with Google, but she decided to leave when she felt that there was something more that she should do. Today, she joins Tony Martignetti in a fantastic conversation about personal growth and the importance of setting aside time for it. She also talks about her career flashpoints, highlighting the significance of determining your measurement of success in unlocking your unique potential. Cara is currently the CEO of The Leadership Consortium, a platform that offers virtual leadership development for leaders at some of the world's best companies.


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Unlocking Your Unique Potential With Cara Shortsleeve

It is my honor to introduce my guest, Cara Shortsleeve. Cara is the Chief Executive Officer of The Leadership Consortium, a leadership development platform for high potential leaders with specific expertise on accelerating women and people of color. Cara joined TLC in 2018 to launch and scale the business. Since that time, TLC has attracted best-in-class clients, including Google, Walmart, SAP, Alphabet, WPP, HBC and a dozen others. She's enabled 1,500 plus executives to lead stronger teams and bring broader strategic mindsets to their business. It's amazing. Prior to joining TLC, Cara spent years in various leadership roles at Google and YouTube. Cara served as a Global Director for GTM and commercialization at YouTube focusing on commercial and product strategy. She was initially hired in 2007 to help launch and scale Google's East Coast mid-market sales presence, after which she led the North American mid-market sales teams for financial services and healthcare.

Before Google, Cara managed the US running apparel business at New Balance, served as Sales Director for Hind Saucony, and spent three years with Morgan Stanley's Investment Banking Division. Cara is a proven operator who excels at shaping products and commercial strategy and driving sustained growth. She's well-known for developing and inspiring teams and relentlessly advocating for top talent, diversity, and inclusion. Cara received her BA from Williams College and her MBA from Harvard Business School. She lived near Boston with her husband and three wonderful children. I want to welcome you to the show, Cara.

Thank you so much. It's so lovely to be here.

I look at what you've accomplished and I can't wait to dig into your story and see what the path was getting you to where you are doing amazing things in the world. Three wonderful kids, what are their names?

We're trying to keep those kids semi-educated in 2020. I'm not running for parent of the year. I am trying just to make sure they come out whole.

I'd like to explain to you a bit about how we roll on the show. What we do is we tell people stories or help them tell their stories through what's called flashpoints. These are moments in your life that have revealed your gifts to the world. They could be traumatic moments or they could be moments where you said, "I need to do something different with my life." I'm going to give you the floor to share your story and share what you're called to share. Along the way, we'll pause and see what's showing up. With that, Cara, go on.

It's interesting that you had to think about flashpoints. When I think about my professional career, a few come to mind. A flashpoint for me was using my time at business school as a time to pivot. Thinking about using that, honestly, I serve a two-year period of introspection and trying to think about I might be skilled to do a ton of different things but what's going to make me most happy and what's going to be the most unique place for me to play in the world. I would say that was a bit of a flashpoint for me. I had a moment during my Google career, I'd always led teams and I had a moment where I took an individual contributor role, which was a super interesting journey for me.

I'm happy to share more in that but I learned so much in that moment. I would say another flashpoint was the decision to leave Google. I always say I had a dream job and it's always hard to leave a dream job. There's a lot that you need to do on your own to be thinking through like, "What is my measurement of success? What defines me? What brings me joy?" That can be a journey for people not to be looking around them and having other people's judgments cloud their own. It's a lot to chew on there but there are a few.

It's powerful right there because there's an element when people do go to an MBA program or to graduate program. There's a desire for more out of life. There's this path that, "I know there's something more in me than what I've had in the past," especially when you've had a lot of success already at that point. You know that there's an element of unlocking more potential. I love that you chose that as a pivot point or as a flashpoint, I would say, because it is a place where people go in and they don't know what they're going to get until they get it.

Unlocking Your Unique Potential: Google is hugely a mission-driven company. The tech is a force for good, and democratizing information is a noble pursuit.

I'm a huge fan writ large around focusing on your own growth and development. I think for all of us as busy humans, oftentimes our own needs are the last in line. You're either taking care of your customers, your team, or your family. List the number of fabulous things that come ahead of you. I think I've always tried to be focused on personal growth and setting aside time for it. I would say for me personally, that time in business school, when I was away from the demands of a job and things like that, you are in a different mindset and it does allow you to be a little more creative in your thinking than you might otherwise be.

What was the biggest take away from that? Would it be the connections or was it the thinking differently? What was it that you felt like you truly got out of that?

For me, what was most interesting is, as you mentioned, I went to Harvard Business School and it's an amazing organization, tons of amazing people but even at a place like that, there are beaten paths. For me, I'd had been on a few beaten paths before that. I was trying to spend my time there, consciously trying to be aware of how might I be different? How am I a different snowflake than some of these other fabulous snowflakes? To close the end of that story, I went into sales coming out of business school, which wasn't even a domain in which Harvard instructed. They didn't pride themselves. I don't think at the time generating sellers. I found a calling to go out and sell running shoes. Who doesn't love that? You can't feel bad about getting somebody hooked on a healthy lifestyle. For me, it was finding the time and a little bit of bravery to think about, "What do I uniquely love to do? How can I make this place work for me?" It was well engineered to work for certain use cases. I had to find the wherewithal to make sure it worked for my use case.

You chose the word bravery and I think that seems to be a word that might embody a lot of the things that you do. You've taken a lot of risks in your life to be out there and do your own thing. It takes bravery to do that. I want to rewind us even further to go back to who you were as a child that led you down this path of maybe taking risks.

I would say bravery in some domains was a learned skill for me. There were certain places where I had natural talents, where I was absolutely fearless. As an example, as an athlete, I was always a strong athlete. I would be fearless anytime I was on a field or I had a stick in my hands but I was not as brave in places where I didn't have the same confidence. That has been a learned skill over time. That has been, "What are the feelings you have? What is the way you look at problems?" When you're coming from this feeling of strength and then how come that might feel or look differently when you're in this other domain and how can you pull some of that natural tendency you have in this one area to this other area? Going back to how would I have showed up as a kid, I think if you'd caught me on an ice hockey rink, I was always about 50 pounds soaking wet but seemed to feel like I was much bigger. I did not seem to understand. I was the smallest person in the rink but there were other areas where that were not as natural to me that I had to practice.

You treat it as a nonchalant thing that you are skating and ice hockey. Let's be honest. That was not something that was common for girls.

I had a big brother. As my parents said, that equipment is expensive so somebody else has to use it. It was handed right down and off I went. It's always a little too big, always a little worn out, but it still brought joy to me, I will say.

How far did you take the hockey? Did you take it into college?

I played ice hockey and lacrosse through my days at Williams College, which was amazing. It's always been a huge part of my life. It's interesting. When you talk about flashpoints, there are so many things that I've done that are different over the course of my career but one thing that has always been steady is I love doing hard work with amazing teams of people. When you look back through that thread that has been there for forever, that has been from all my days in sports all the way through, I enjoy hard work towards a singular goal with driven people. I played all the way through Williams College and then HBS. We fondly have a little ice hockey team there called the HBS, The Women's Blades. I got to play a little bit for fun back when I was in business school as well.

You're doing things by your own way and choosing your own path, which is powerful. I love this aspect of team that you said, the hard working team, because that does follow all the way through your story. I know we're going to learn more about this as we evolve from where we are but that is powerful. When you start to be exposed to that at a young age, it has an impact on how you show up for the rest of your life.

It's a lot of it when you start unpacking these things. Both my mom and dad came from large families. I grew up with my grandmother living in the house with us. Both of my parents worked and it was very much part of our ethos as a family, which is we have fun together but we work hard together. This is your core team. This is where your loyalties lie. No matter what happens, you always go to bat for your brothers and sisters. That ethos from such a young age was so much part of my environment that has carried through to this day. I'm a hugely loyal person, hugely team-oriented.

There are some people who would say there's hard work and then there's working smarter. I'm sure there are elements of that you've started to grapple with as you moved on in your path. There's nothing to discount the fact that when you have the ethos of hard work and working with a team together, it can get you so far.

It brings you so much joy. That's something that I have found in my life. I am most joyful and I feel most productive when I am doing that work with others.

Let's fast forward a bit. Here you are working in sales. That one is sneakers.

Even better, I was selling sneakers in sports for us. I was out there talking to women if they were getting the support they needed. I'm like, "I love your whole life view but physically, are you getting the support you need?" Yes, I was selling running gear.

The great thing is that you're coming from a place where you know the importance of the team, you know about people's need because you have the sports gene, if you will. That's powerful. What drove you to the next point in your story?

This was following business school. I was at both Saucony and then New Balance. I had been a huge sports enthusiast my whole life, so I chose those domains given the products that they sell. What I realized when I was there is it also mattered a great deal to me the way the work was done. I went to business school fairly young. I was never going to be the oldest person in the room. I was never going to have done the job the longest. I started thinking passionately about not more merit based but strongly merit based organizations where there wasn't a way somebody had always done it.

You couldn’t say, “We make up first this way because we've done them for 30 years.” I was interested in being in a place where the fact that I hadn't been there 30 years wouldn't preclude me from bringing creative ideas to the table. That is how I found my way to Google. Google was opening a sales office in Boston at the time. This was 2007. At the time, they were predominantly West Coast business. The midmarket was Google's revenue engine. They had a presence in the West Coast where they ran a lot of that part of the business but they hadn't expanded to the East Coast.

Coming back to the point of, "What is the most valuable part of business school?" One of my classmates at HBS had gone to Google following graduation. I reconnected with him and he'd said, "We're doing amazing work and we're coming to Boston." At the time, I'd said, "No, I'm good. Thanks. I'm doing God's work here. I'm selling running shoes." He had said, "Hear us out. It's an interesting business." I think as a pivot point, what I learned was I could be equally passionate about something that I hadn't "grown up" with but that I felt like was making a big difference for people. That's how I ended up going to Google. It's a hugely mission driven company, so I was a believer. The tech is a force for good. Democratizing information is a noble pursuit. I ended up at Google back in 2007 helping stand up for Boston office, which was an amazing work.

You say no big deal because Google is the biggest company in the world but to have that opportunity to get into that type of a work, it speaks a lot about who you are as a person. It's fantastic. As you said, then you feel like, "I have this gift. I'm in this place that is so amazing." How would one want to leave that?

Before the leaving of it, I will say to all my fellow type-A personalities out there, between when I got the offer and I joined Google, I read three books, introduction to Google AdWords. I read three different books because all I know is that I go there and search. I know it is a search engine. I will say to the folks who are coming in, "Follow the dream. Here's an example. Google is a company. I was a believer in what they were doing. I knew very little about what the day job was going to be but trust your gut and have the confidence that if you believe in the mission and you believe in the work someone's doing, you'll find a way to fit in.”

Fast forward, I had an amazing decade. I often say I grew up as a leader. I grew up as a professional there. It was a point in my life where I joined Google single and I left Google married with three kids. Think about any young parents. I talk a lot with female executives. There's a decade or many years in there that's formative for folks as they're trying to start families and succeed professionally. I always have a great deal of empathy for young working parents but that's where I grew up. I did my growing up at Google. I always think of it as an amazing gift. It was an unbelievable organization with unbelievably bright people. I think of it as a continuation of my education where I got unbelievable chances to run different types of teams, work with different types of products, play different types of roles, and then start showing up as the executive I was going to become. I started having a lot of success leading teams and leading organizations. It was a formative class.

VCP 67 | Unlocking Your Unique Potential

That's one thing that I constantly hear people say that you have at least one part of your career where you have formal years. It's great to have a company where you can expand your boundaries, see your range show up, and then at some point realize maybe it's time to move on. I've gotten what I needed from this organization. We're not talking about the old days where it used to be different. Having that foundational formative experience is very powerful.

I also think it was a neat period because Google itself was growing up. It was a neat way to be able to learn and evolve as a human and also help the organization learn and evolve for all the other humans that were going to be coming along the path after us. I agree. There are times that everybody looked at and say these are formative points for me. I would say my time at Google was that way. Sometimes you take a moment and you say, "Maybe I've gotten what I need to get or I've contributed to my max. How should I be thinking about things?" For me, I think one of the harder decisions for me and my career was to leave Google because a lot of people consider that a destination. A lot of people would say that, “That's a place I'm trying to get to.” It's hard to sometimes explain to folks I had an amazing role, an amazing team, an amazing point in my career, in my tenure there but part of it was the introspection.

The point of saying, “How much can I contribute to Google and how much does Google need me versus how much can I contribute somewhere else and how much does that place need me?” We all like to think we are incredibly fabulous and irreplaceable but my hope is that there are tons of up and coming Cara Shortsleeves doing amazing work at Google. Sometimes we need those people doing work outside of those amazing companies. We can get onto the next chapter. I ended up leaving Google to start this business, which I'm incredibly passionate about, which is around advancing women and black and indigenous people of color, even more so than what we've been seeing now.

One of the things I wanted to pick up on from your story is you talked about intuition somewhat briefly. I love that you said that because there's something about the outside story and the inside story. Some people say like, "I don't know when should I trust my gut and when should I continue to look at the outside statistics or what the outside images." I see it as a muscle you build over time and you figure out, "How is my experience serving me," when it's not feeling right knowing that it's okay to part ways with that experience and say, "I've got what I need. It's time to move on." Even entering Google for the first time saying, "There's something about this that feels right. It feels like this could be a good experience. Even though I may not know all the things that I need to know, there's something about this that feels like it will be able to serve me well."

I agree with that on the intuition piece. It's something that I've always tried to hold dear. I think people have different names for it. I call it a personal board of directors. It's who are the people in your life that really know you, they've seen you at your best, they've seen you at your worst, they know what lights up your life, and they know what is soul crushing. I'm sure for so many of the people that tune in with whom you work, they have great opportunities. The challenge is what you do say yes to. We all get to a point in our career where hopefully that's a good challenge to have but you're going to be throwing a lot of different things and how do you decide what you say yes to. For me, the intuition is a big piece of it. Some of the people that I value, I'm able to sit down with them and say, "There's not quite as much joy in my day as I think there should be or I'm waking up feeling a little laggard but I still slept eight hours. Maybe my energy is low." I agree with the intuition piece and I agree with finding those people who can help keep you honest in a world of tons of competing data points and signals.

I love that you brought this in because this is a great concept. It's about listening to the people who you trust, not everybody, because there are so many people with opinions who will tell you or feed you, not wise but the information that they think is right and have to be able to filter that out and go to people who you trust who know you well. I love that. It's so powerful. Let's talk about the TLC.

To backup, I had been at Google. I'd hit the decade mark and I was starting to think to myself, "Let's have some little self-talk, Cara Shortsleeve. It's been many years. How often do you spend years in places?" I think if you're not a physician or an attorney, it's probably not that often. It was an opportunity for me to think about, "This has been an amazing chapter. If I were to think about the contribution I want to have in the next years, do I want to do that through this amazing vehicle in Google or do I want to do it through other vehicles?" I started to think about from a mission value standpoint. I had a deep passion around leadership writ large and development of others that had been something that I had seen over the years. I got better and better at and it brought me more and more energy. I'd lived in tech and prior to that, sporting goods and finance, which are some of the most gender non-diverse sectors.

I'd seen firsthand, diversity falling off at executive levels. It breaks your heart because everybody knows all the business case around it but these businesses would be better, faster, stronger if they had more diverse decision-making. I started to think about other places that I could play here. I got reconnected back with a professor from Harvard Business School who was well-known in this space of culture building and cultural excellence. Her name is Frances Frei and her wife is the other founder of the business. Her name is Anne Morriss. They had an idea that they wanted to do some important work in this area. They're both amazing thought leaders. They needed an operator. It seemed like the perfect timing and a perfect match of skill.

When I'm looking for a new opportunity, I want a dear friend of mine, Lexi Reese who's a COO at Gusto, which is a great business servicing small business. She'd always said to me, "You want to be able to contribute when you arrive and you want to be able to have room to learn." It was such a good balance of I brought so much to the equation in terms of my ability to run and scale businesses and yet there was going to be so much I had to learn, which is great from a growth standpoint around starting a business from the ground up. It seemed like the perfect solution and it has been a dream. I always say I left a dream job for another dream job. It's been a great year.

Those are the nuggets that people need to hear that there's an element of having that room to learn but also being able to contribute something, bringing something to the table that will give you the confidence that you're in the right place. I love that you're able to connect with something that you're passionate about. That is so powerful. We're lucky to have you in that space, the impact that you're going to be making. You're an operator.

Yes and it's amazing. The other thing I would encourage people to think about is you learn so much as you go along. Sometimes to see it and to feel it, you need a change of context. I had clearly learned an amazing amount over many years at Google but when you switch context and then you can replicate things or you can bring those skills to bear, it's an impactful moment. I would say that's another reason why change is good in your career because you can bring to bear and you can understand, "Here are the things I've learned. I didn't know this was a skill." Outside of the world of Google, there are not as many people that do this certain thing as an example. That's another vote for people to think about. Change can be scary but it's also an unbelievable way to understand the skills you have cemented.

This thought about the context makes a difference. I often tell people that the environment you're in makes a big difference. It's like the fish in the water. They don't know they're in the water. Once you take them out of that or you have someone who tells them, "You're amazing. You're doing amazing work." They may not even realize how powerful they truly are. That's why I always think about the stories that when we pulled the story forward and look at where people start, you see so many amazing gifts that revealed themselves in that story. It's powerful. One of the things I wanted to highlight too is that when you find the complimentary people to partner up with, a lot of my guests who come on, not everyone, they're part of teams. They're cofounders. I've even interviewed multiple people at once on the show. It's been powerful because I've found that there truly is no one person who does it alone.

I feel like in my time at Google, just to take us back one step, I started in clear sandboxes. You are responsible for this number of accounts, this much revenue, and this number of bodies. Go get your quota. Over my time at Google, I moved into a very different type of role where there were absolutely no walls on the sandbox. It was, "Your job is to bring these different groups together and try to make sense of something." I found that was a skill that I had and one that I liked and also was additive to me because it reminded me, I didn't need to know all the things, I needed to know how to ensure all the people who did know that things could bring their voices to the table. Carrying that forward to my life at TLC, the founding team is a great example. We have Frances Frei, who's an unbelievable professor and thinker. We have Anne Morriss. They do a lot of their work together but they are both amazing in their own rights. Anne has done a lot in terms of standing up and running mission-driven businesses.

When you think about me coming in, I have an amazing background in how do you hire successfully? How do you scale successfully? How do you do customer orientation and service at scale? How do you think of partnerships? All those things that I brought. Anne has this amazing nexus of thought around mission and service driven organizations and Frances has this amazing set of thoughts around, "Here are all the things that are possible if we think big." To your point, that frees me up as an individual feeling like I need to know all the answers. It enables me to know what I know best. It enables me to say to them, "This is my domain. Trust me on these things. Frances, you make this call over here because you know it best. Anne, these are the places that I desperately need you to think because we know you're our smartest brain there."

It would be remiss if we didn't at least drop in the name of their book.

VCP 67 | Unlocking Your Unique PotentialTheir book is so amazing. Your readers will have to think they could see it. It's an amazing book called Unleashed: The Unapologetic Leader's Guide to Empowering Everyone Around You. To give people the one-on-one version, the idea is leadership is not about you. Leadership is about empowering and bringing out the best in others. There are a lot of great nuggets in there around, “How do you make sure you're empowering others, bringing out the best.” There's a lot in there around inclusive teams and environments, which I know is topical for folks nowadays. There are tons of wisdom in there, something for everybody. It's a worthy read.

As we're getting close to the end, I wanted to ask, what are 1 or 2 things that are the biggest lessons you've learned along your journey that you want to make sure that people hear? You've shared so much already but I wanted to make sure that if there's anything you're dying to get out into the world.

The first I would say is for me, most of the changes I made I went smaller to go bigger. I went to a small sporting good shop called Saucony that some avid runners know but not everybody knows. I left Google to run a startup. I would say so many people think of career and career progression as linear and hierarchical. It has to go up a ladder. I hope that many people have shared this on the show but I would say so many of the most amazing growth opportunities come from the random fork in the road from like, "I'm going to go into an individual contributor role before I go back to a management role." This concept of going smaller to go bigger has been important to me.

The other one I would say is do your very best to be your own, to benchmark your own success. It's hard in this world and take me as a working mom. I could look at Instagram and look at all my fabulous mom friends who are not working outside of the home and think, "I will never be as good mom." I can look on my LinkedIn feed at all my fabulous colleagues who don't have kids and say, "I'll never be as good worker." You got to know, "Here are the things that I, myself, balancing. Here's what brings me joy. Here's what I care about." I might care about this more than this and that might be a different decision than somebody else. The sooner and faster you can start doing your own validation and have your own scorecard, there will be so much more joy and you deserve joy. Those are my two tidbits.

They're both amazing but that last one is so meaningful. I felt that. It's something that we constantly struggle with. There's no person on the planet that doesn't struggle with that. I thank you for bringing that into the space.

You're welcome.

One last question, what is one book or multiple books that have had an impact on you and why?

I love to read. We should talk for another hour. I'll give you three. Two follow a similar theme and one is a little bit different. The first two that I have loved are The Moment of Lift by Melinda Gates and Becoming by Michelle Obama. If readers are unfamiliar, I would say they're both interesting stories. There's a gender angle that's important to me than the work I do. I have found it interesting. The Gates Foundation work around empowering, unlocking women around the world. It's told in an interesting way. It's told through vignettes of different women and girls around the world. Becoming, it's well known but I love it for a lot of the raw transparency that is in there. It brings to life an experience that is not familiar to many people and it was a great way to do it.

There are so many other wonderful books as well but those are two that I read in 2020 that I appreciated. In moment in time, Team of Rivals is one of my favorites. I understand that the work that I do, it's a lot of fabulous white men. I would say that knowing that it might not look representative to everyone but it's the story of Lincoln's cabinet and how you pull from different sides and the strength and difference. I know that difference might not look at surface level as compelling as different looks nowadays but there was a serious difference in thought and difference in approach. It was how you do truly engender collaboration, real difference of thought coming together towards a better end. In this day and age, getting polarized sides to work together no matter your learning is a novel or they cost.

It's funny because it made me think of this idea that I've been playing around with for a while, which is that we need to have divergent thinking but convergent hearts. It's important for people to come together. We need different thinking and we need people to come together where they connect and converge on wanting to be together at heart. Meaning have the scene desired to be one in unity. I don't mean to be weird about it but that's important. It's important that we all see that connection as we're all one humanity but we also want to make sure we have different thinking.

The business I run is all about celebrating differences. There's no question, differences good, do advanced opinions, do advanced decisions but the question is, “How you can bring that difference to light in constructive and beneficial ways.” Team of Rivals, anything Doris Kearns Goodwin. I'm a blaster fan.

She's fantastic. In fact, she's going to be hosting the mass conference for women this year, one of the hosts, which I do a lot of work around that. I don't even know where to begin but I want to start by saying thank you so much for bringing your story, your insights, your brilliance to the show. It's an honor, Cara.

It's so fun to be with you. I appreciate it.

Thank you. For those who are reading, they might want to know more about you. Where can I find more about you?

They can look up the business I run. It's called The Leadership Consortium. They can check that out. I am most active on LinkedIn, so you can read a lot about some of the things that I think deeply about and reflect on in my "free time." Find me either place and I look forward to connecting with any of you who have like-minded aspirations or interests.

Thank you again and thank you to the readers for coming on the journey. I know you're leading with so many great insights. Hopefully, you're inspired to go out and make some change in the world just like Cara has. Thank you very much, Cara.

Take care.

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