You’ll want to be sure to stick around for the entire episode, because Kelly dives deep into important career skills like storytelling, listening to other people’s stories, and how to strategically think about your next career move.
Kelly Wright is the former Tableau Executive Vice President of Sales, and was actually the first sales person at Tableau.
00:00:03 Ash Faraj: Hey, it’s Ash. Today’s guest is Kelly Wright, Tableau Software’s former Executive Vice President of Sales and [she] was actually the first salesperson at Tableau. You want to be sure to stick around today because Kelly dives deep into important career skills like storytelling and listening to other people’s stories, and how to strategically think about your next career move.
00:00:32 Ash Faraj: Really quick, before we get into the show, we’ve started to invite our audience members on the show to connect with our guests and ask questions towards the end of the conversation. So if you’d like to be on our show, you need to make sure you’re subscribed to our newsletter on our website and look out for emails that invite you to be on the show. And, as always, you can reach out to me directly if you have any questions or you just need someone to talk to. My email is Ash@ExecuTalks.com.
00:00:56 Ash Faraj: Kelly’s story starts with… well, stories. From a very young age, Kelly loved listening to other people’s stories and she loved sharing stories. She realized from a young age that this passion for storytelling would translate very well into entrepreneurship.
00:01:12 Kelly Wright: Anyone that knew me from way back when would say I’m a talker, and that everyone was always saying, “Hey, have Kelly talk less.” So Kelly’s stories and being able to talk to anyone was something that I always did. In terms of being a salesperson, I think that that’s who I was super early on. I always loved the idea of -- when there was a competition at school of going and selling candy bars or selling cookie dough or whatever it was, that’s what I wanted to do. I thought it was so fun to go talk to people whether it was at the grocery store or going door-to-door and being able to sell. Then in high school, I actually sold shoes. So I worked in the shoe store and I sold shoes. It was this town shoe store that everyone went into. I got to see everyone and talk to people and hear about their stories. Then I had this crazy job when I was in college where I ran my own business selling educational books door-to-door. And in that job -- and that was really foundational for me to decide that I wanted to do entrepreneurship and I wanted to do sales as a career. During those four summers when I was selling books door-to-door in college, I talked to 12,000 families in their home over the course of those four summers. I just loved hearing everyone’s story. What was really, really cool is you hear a family’s story about them; what their kids were interested in, how families focus on their kids’ education. I think that’s when I was really [indiscernible] that I wanted experience in sales. And, yes, sales is about storytelling, but it’s even more about bringing out other people’s stories. So as a salesperson, I am privileged every day that I get to hear everyone else’s unique stories, and that’s what’s really fun; not telling my own stories but hearing their stories.
00:03:12 Ash Faraj: And what do you feel makes a great storyteller or a great salesperson?
00:03:17 Kelly Wright: Most people who are in sales, and who are talkers just like myself, tend to talk more than you listen. If you want to hear people’s stories, you have to be good at asking the right kind of questions but then also listening to the answers. So I think one that’s real important: good listening skills. The second is being able to really have a level of empathy. I think sometimes people ask pretty superficial type of questions where someone’s not going to want to open up unless they can see that you’re leading with empathy. And then also you’re showing some vulnerability too. Because people aren’t going to share much about themselves unless you’re going to be vulnerable and share things about yourself as well in the conversation. One way that I like to explain it -- and this I learned from my good friend Skip Miller. He does sales training, and he did a bunch of our training when we’re at Tableau. He does sales training for many companies throughout there. He always talks about the three levels of ‘why’. I love thinking about this as a model for storytelling because most people ask questions that get to the first level of why. What makes you interested? What’s your problem? What makes you interested in buying whatever I have to say. It’s very superficial. And so you get to that first level. The second level of why -- and many salespeople do this; many people do this -- that you get to the second level of why. That you’re getting a little bit to what’s the underlying reason and what’s the motivation. But not very many people get to the third level of why. And the third level of why is about the why of what is motivating and why is that individual human being motivated? So not the reason for their company or the reason for the department but what actually is a motivator for that individual person. So for instance, if someone’s buying something and they’re buying a software at their company, yes it might be solving a problem to increase productivity. Yes, maybe they need to get more revenue which seems the reason. That might get you to the first two levels of why. But the third level of why might be that that person really wants to get a promotion and they want to do a great job. Or it might be that that person wants to prove themselves. Or that person really cares about productivity because they’re working so much, they don’t have time to spend with their family and with their kids. Or that it’s so hard to do their job that they don’t have the level of engagement and they’re not having fun at their job, and they just really want to love what they’re doing. So when you get to that third level of why, you really can more emotionally connect human being to human being. That for me is what is so fun about the storytelling. You really get to hear the essence of who people are and what makes them tick.
00:06:15 Ash Faraj: So what was your first job after the job selling books?
00:06:21 Kelly Wright: My first job after I finished selling books was, I worked at Dale Carnegie which is part of the reason I love that book How To Win Friends and Influence People. I was doing sales training, public speaking training, management training. And every day, every week, I was going and I was doing training at different organizations. One of the organizations that I actually did training for was Bank of America in this mortgage division. What happened is: if you’re doing sales training, oftentimes the company who’ll come back and say, “Oh, we’re hiring salespeople. We need someone that understands how to do sales.” And so they talk about, “Hey, what do you think about working here?” And so that was how I ended up getting the transition from: I sold books, went to Dale Carnegie, and then ended up going to Bank of America. The interesting part of Bank of America is, I was in the mortgage division. At the time, I was in my early twenties. Almost everyone in that division had been there for like 20 to 30 plus years. So they had been there for a really, really long time. In fact, we didn’t have any computers or anything. Everything was on typewriters when I first went to Bank of America. I remember doing sales, getting the loan orders, and I couldn’t even just type it in. You had to go to the processor that had it on their typewriter. They would put everything in. They had to use whiteout and then go through. Because if you had the signature on it, you couldn’t like just print it out; you’d start over again. So it was super, super complicated. I remember just thinking: “There’s got to be a better way.” How I ended up doing well at Bank of America is I felt like there wasn’t enough of engaging with people, having the storytelling, being able to provide really phenomenal service for people that were within their private wealth group. I wasn’t hired into that group, but I ended up fostering, making really tight relationships and ended up doing a lot really well. I got many, many sales for Bank of America. And then there were a whole bunch of these people that had been there 20, 30 years [who] said, “How can someone come in and so quickly develop this bigger business?” I think that was another lesson for me. You need to do just wreck the old way. You need to be constantly innovating and constantly disrupting. Because if you just keep on playing the old playbook time and time and time again, you get stuck in the Innovator’s Dilemma which many of us have probably read that book. So you need to be thinking about: How do you uplevel? How do you think out of the box? How do you innovate? How do you do things differently? I think that’s where I thought: “Hey, I want to do something that’s disruptive. I want to do something that’s cutting-edge.” And that over time, after the next couple of classes, is what led me to the technology.
00:09:09 Ash Faraj: At a certain point in her career, Kelly was doing really well at Bank of America selling mortgage contracts for homes. She loved her job and was making great money by her standards, but she decided to go back to school for an MBA. Now, this might seem a little puzzling. She knew that by going back to school she was going into debt and wouldn’t necessarily be getting a pay raise, but her desire to learn drove her in that direction.
00:09:33 Kelly Wright: At the time, I was working at Bank of America. I was making pretty good money, and people thought I was crazy. They thought, “Why would you go back to business school and pay all this money to graduate to get a job where you’re making less money than what you made before you started?” I think sometimes people can be very short-sighted. For me, my career wasn’t about money. It wasn’t about making money. It wasn’t about just how flexible… I was very flexible at Bank of America because I was making high commissions, so I’d taken a lot of vacations. I had a lot of flex time. But for me it was about, “How do I think about my journey and learn, so that I can do what I want to do longer term for my career?” I knew I wanted to do something entrepreneurial. I wanted to be involved with building my own business, with being able to have a broader impact. I had sold books door-to-door. I had sold Dale Carnegie training. I had sold Bank of America mortgages. So I had sold a whole bunch of different things, but I had done it more on the sales side. I felt like I was pretty good on the soft skills. I knew how to connect with people. I knew how to story-tell. I knew sales. Maybe a little bit tangentially of marketing. But when you’re doing entrepreneurship, or you want to be involved more as a general manager, you need to be able to really think strategically and frame business problems from a much broader scope incorporating general management, leadership, finance, operation, and all these different components of it. I had majored in Political Science in undergrad. I’d always been kind of more on that fuzzy side; not the technology side, not the hard skills. I really wanted to be able to get a broader array of skills; financial skills, more quantitative skills, and to understand all those different disciplines. So that’s why I wanted to go to business school. The reason I chose Wharton at the time was just because Wharton at that time was known for being really the best quantitative school that was able to augment my ability to balance out the hard skills with the soft skills. And then also to build a network, to get more general management. So when I went to business school, I thought, “Okay, well now I need to understand more strategic training which will give me more exposure to all these different functional groups and all these different industries” which is why I did my summer at McKenzie. After graduating, I went to Bain so I could do strategic consulting and have a better understanding of all those different disciplines. And how really, most importantly, how to strategically think about solving business problems from all different vantage points in all industries and all functional areas.
00:12:26 Ash Faraj: So, Kelly, business school is expensive, right? But there is a lot of value. How should people decide on whether or not to go to business school?
00:12:38 Kelly Wright: Oftentimes people are thinking should they go to business school because is it an uplevel; their ability to make money. I think that that’s just the wrong thing to think about. I already told my story. If I wanted to just immediately make more money, I should have just stayed where I was at Bank of America because I actually took a pay cut when I started working at consulting. I was making less than I had been making with my sales commissions at Bank of America. For me, the way I navigated my career -- and one of the thoughts that I’d put out there, so this is not only a business school question, this is just a general career stepping discussion if you’re thinking about: “Should I take the next job? Or what should be the next step in my career?” -- For me it’s always about having this growth mindset. Where can you go and continue to learn and continue to develop skills and surround yourself with other people who really want to learn and do better so that you can uplevel? So that was one of my main reasons for going to school. One, I just had a thirst for learning more. I knew I wanted to learn more, but I also felt like if I wanted to keep on doing what I was doing now -- or at that time -- then I didn’t need to go. But, if at some point in the future I wanted to do something different that was bigger, that was broader, that was more challenging, then I had to go and invest in myself. So I looked at that as investing in myself. I wanted to invest in the education. I wanted to invest in the network. I wanted to invest in understanding about different industries, about understanding functional areas, and then at the same time keeping in mind what directionally are your longer-term goals? For me it was entrepreneurship, and I didn’t have all the skills that I needed to do that. Now, the flip side is, if someone’s doing something that they love that they don’t want to do anything different and they feel like they can learn and grow a lot in that same environment, then it might not be necessary to go to school and get another one. Sometimes people think they just want it for a place on their resume. I think the pedigree helps you, but people should be doing it because they want to learn something tangible and for specific goals that helps them rather than just a stepping-stone that they think is required, because you can be successful certainly without an MBA. It’s a great opportunity after you’ve had some work experience to go and take risks in a safe setting; you can try different things, different clubs, different kinds of work experiences, talk to people that you wouldn’t have normally met because you are in this 2-year or 3-year -- depending on how you do your MBA -- this environment where it really does encourage thinking beyond your comfort zone and taking risks.
00:15:33 Ash Faraj: So after her MBA, Kelly worked in consulting for a little over a year. She decided she was going to go join a start-up as the VP of Sales because she still had this passion for entrepreneurship.
00:15:46 Kelly Wright: I learned a ton in consulting. I learned how to strategically frame problems. I got exposure to many different industries and functional areas. I really learned a lot about how to do analytical thinking that helped me a ton when I later on was at Tableau. I think the challenge was -- is part of the reason that I got that role in consulting is because people do all of that analytic work to help to solve customer problems. And then down the road, seven, eight years later, the partners in consulting firms they’re the ones that go and help to sell the engagement. So I think that there was this thought of we want -- the consultants wanted to have people that had those analytical minds actually, but then also people that had those natural sales skills naturally so that they later on could help to go sell and onboard these customers and clients. What I found was, I just really just wanted to do that now. I love being able to hear people’s stories to engage in that way, and then this tech boom happened. And I thought, “Hey, I want to be on the cutting edge.” I want to be doing something disruptive. I want to be able to be involved with changing the paradigm. All that I was involved in in consulting, but in consulting you do the strategy but then you didn’t help with the implementation. And I loved the operating side, and I loved the sales side and hearing people’s stories, and so that’s why I jumped. There was this internet boom, and I knew I wanted to be part of it. So I jumped. I joined AtHoc. I was there for six years in Sales, Business Development, Client Services. Learned a lot about technology. Learned a lot about entrepreneurship and how to build a company. And then there was an opportunity to go be the first salesperson at Tableau and I jumped at that.
00:17:41 Ash Faraj: How did you land at Tableau Software? What’s the story behind you getting to Tableau?
00:17:48 Kelly Wright: I had met Christian Chabot, who is the CEO and founder of Tableau because he was friends with mutual friends. So what had happened; she’s a friend of mine who I’d gone to Stanford with. Her husband actually ended up being the CFO of Tableau. So he joined very early on as Head of Finance at Tableau. There were these social engagements, dinners, and such where we would be socializing, and I met Christian a couple of times. Through those conversations, I had heard they’re starting this cool company that was going to help people see and understand data. And it actually goes back -- believe it or not Ash -- to my book selling days. Because when I was at Stanford and sold books door-to-door, people remembered me as this person, this crazy salesperson that did this job selling where she made a lot of money selling books door-to-door in college. So when people would start their own business, they would come and say, “Hey Kelly, when we’re ready to hire our first salesperson, we’re going to come find you.” That was really what happened at Tableau. They were looking to hire the first salesperson and came and said, “Hey Kelly, we’re looking to hire the first salesperson. We remember you sold all those books. Would you be interested in coming and having a conversation about Tableau?” And the funny part was, you looked at the job description of what Tableau was looking for in that first salesperson; someone who had worked in business intelligence, someone who had done enterprise sales, someone who had been at companies to help take the company public, and there’s this whole list of things. I’d done none of those. But I had… hopefully people thought I was somewhat smart. I was in sales, but I hadn’t done any of those other things. But I think it was just someone that has the grit. Someone that’s going to have the hard work. There was a lot of just cultural alignment with the team, and that’s how I landed there. So it was a great decision.
00:19:44 Ash Faraj: One thing I always try to ask in this conversation is, should someone have a rigid plan in terms of their career or should people kind of go with the flow? I absolutely love Kelly’s response and advice here. It’s actually helped me reevaluate how I think about my career journey.
00:20:02 Kelly Wright: Some people have this preconceived notion of where they want to be in 40 years or 20 years, and they’re so rigid on all these steps. To go back to your other question about business school. They say, “Okay, I have everything mapped out. I’m going to do this job in banking and then I’m going to go to business school and then I’m going to have this job in consulting.” They have everything all planned out. And if you go ask people who are later in their career, all the steps and permutations don’t ever go exactly as someone has in their mind. To be able to evaluate what doors are opening at that time -- and rather than just shutting them and say no because it wasn’t on your preconceived plan that you built when you were 21 -- to be able to say: “Hey, does this make sense?” The way that you evaluate that is based on what you’re going to learn, based on the people who you’re going to be working with -- or, if it’s not work it might be an organization or volunteer. What are the people? Are there people where you can actually bring your best authentic self? Is it an environment and a culture where you can thrive? Are they people that are really smart that you appreciate their values as well? Where you’re all going to bring out to do the best? And so I always looked at things based on: “Am I going to learn? Am I going to be able to take risks and challenge myself in new ways which is related to learning?” And then, “Who are the people I’m going to be surrounded with? Are these going to help me to bring out the best in myself and am I going to help them? Is everyone committed to actually doing their best, hardest work so it’s not just a few people that are working hard?” And that’s how I’ve made my decision. So each of my careers were you look at what door’s open? I mean you need to actually think about it and just figure out what door you’re going to walk through. Then your second question is about your relationships and people. So everyone’s really busy. People aren’t necessarily thinking how they’re going to proactively build their network, but I think this is part of storytelling as we’ve talked about before. Part of that storytelling is: learn to be a good listener. Being able to actually hear other people’s stories so you can make real, true, authentic, emotional connections with people. If you understand that and you build a good connection, then you never know when that connection is going to come back and maybe help you at some point in the future. There are people that they do networking just for networking sake and that’s not really authentic. I mean people can tell you’re just trying to get to know them so that you’re building up your rolodex. When you’re doing networking it’s more about, “How can I hear other people’s stories? How can I help them? How can I hear what’s important and interesting to them?” And then I can help them to reach their goals and what they’re doing and ultimately that might come back. Yes, I’m all about building relationships and doing that networking, but it’s not for networking sake. It’s because I love hearing people’s stories and I love those connections, and so then that helps to build up the network. Sometimes people ask me, “What are some of the traits that make a good salesperson or make a good executive?” or whatever it may be. There’s a whole list of traits, but I think intellectual curiosity or just general curiosity is a huge one, and then having this growth mindset and having a thirst for learning is another. Because people that aren’t interested and serious, they’re not going to continue to push the envelope. They’re not going to be able to be innovating. But also, they just get stale, and they get stuck in their own way. As we’ve talked about, you always need to be able to uplift. You always need to be able to go further. There’s always more to do. And I’m one that says the more I learn, the more it’s just so clear how little I know. Just trying to always chase how can I learn more? I like learning in all different ways. I love reading. I read tons and tons of books. I love talking to people. I love trying out new skills. I love visiting new countries. It’s just always, always, always “do learning”. Why would you not want to learn? Why would anyone ever say they don’t have a quest for learning? That’s just bizarre. Why would someone say: “I’m done, I learned enough”?
00:24:48 Ash Faraj: So during your career at Tableau, was there ever a moment where you felt like you had a mistake and looking back you felt it was an experience you learned from?
00:24:57 Kelly Wright: One thing was, I was a really bad manager. I just was. I was a good salesperson early on. But then when I stepped into the managing and leadership role, I really tried to manage everyone as if I was managing myself. I tried to manage everyone as, “What would be my ideal for if someone was managing me?” But the challenge is there were not many people like me. I mean everyone is different and unique in their own way and when you’re managing people you need to understand what makes that individual person tick. What are their motivations? What’s going to help them and be positive to them? What’s going to be negative to them? People have different strengths and different weaknesses, different development areas, and you can’t just have this one size fits all in terms of your management style. And it certainly can’t do it in a way where it is as if you’re managing yourself because they’re… If we had built Tableau where everyone was like me, then everyone would be talking over each other. Everyone would be interrupting each other and it would have just seemed like a crazy type of environment. You want to have those different types of people. I think that I definitely had some challenges early on to learn. “Hey, you know what? It’s not about managing a whole bunch of Kelly Wrights.” It’s about managing people from where they are and what they need and that taught me. I already knew it’s about learning people’s authentic stories and being able to emotionally connect with them. That’s how I was doing selling but that wasn’t how I initially approached managing. I learned: “You know what? It’s very similar.” If I had to hear their own unique story and be able as a manager and a leader to meet them, where they needed someone to help them, to bring out their best authentic self in a very different way for each person. There are some general overarching management skills, but you need to be slightly different in how you manage each individual person. So that’s one of my learnings that I would say was early on. There’s a lot of people that they end up being promoted from individual contributor into the manager role. Just because you’re a top producer as an individual contributor doesn’t mean you’re going to be a great manager. That’s something to think about too. It’s fine to be committed to be an independent contributor. Everyone needs those independent individual contributors who are rock stars, who are really good. So the only path isn’t to go into management. There’s people that just continue to shine at whatever it is they do and that’s an okay path. If you do opt to go into management, you need to think about just because you’re good at what you do in your individual employee role doesn’t mean that you’re going to be a super star in a management role because there’s different skills and abilities that you need.
00:28:09 Ash Faraj: Hey guys. We’re now at the last segment of our show called “Connection Session Questions” where we ask questions that allow you to get to know our guest on a much deeper level.
00:28:19 Ash Faraj: If you were to meet the 25-year-old Kelly, what advice would you give to her?
00:28:24 Kelly Wright: Stop and take a breath sometimes and enjoy the present. Look around and be grateful for what you have and who you know and take it in. I think I was always just racing, racing, racing and always trying to get to the next thing where sometimes I didn’t take enough time to look around and just enjoy the moment.
00:28:49 Ash Faraj: What in your life you feel has given you the greatest sense of fulfillment?
00:28:54 Kelly Wright: My kids.
00:28:55 Ash Faraj: If you could be remembered for just one thing, what would you want that to be?
00:28:59 Kelly Wright: Being kind.
00:29:01 Ash Faraj: What do you feel the most important life skill is?
00:29:04 Kelly Wright: I think it’s being empathetic.
00:29:08 Ash Faraj: What’s the best advice that someone has ever given you?
00:29:12 Kelly Wright: So many [indiscernible] pieces of advice. I think control what you can control.
00:29:17 Ash Faraj: And the last one is: if you were stranded on an island and you had access to one meal, what would that meal be for you?
00:29:23 Kelly Wright: Maybe chocolate cake and some ice cream.
00:29:26 Ash Faraj: Thank you so much for listening. Now, if you enjoyed this episode, please leave us a rating and review on Apple podcasts. It only takes a few seconds, but it’s worth so much to us. We are helping new professionals in a very unique way, and we need people to hear about it. We need you to help us reach more people by leaving us a rating and review. I hope to see you again next week.