I recently interviewed Penny Pennington on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is a Fortune 500 CEO named as one of the 50 Most Powerful Women in Business for a second consecutive year. Penny Pennington is the CEO of Edward Jones, which manages over a trillion dollars for 8 million clients around the world. Penny, thank you for joining us.

Penny: Adam. It's such a pleasure. Thanks for having me.

Adam: The pleasure’s mine. Penny, you spent the first 15 years of your career working in investment banking and were a managing director at Comerica before you pivoted and became a financial adviser for Edward Jones. And that isn't exactly the kind of career move that most MBA career centers would recommend to their students. And firstly, I wanted to ask you, what drew you to the field of investment banking out of school? And secondly, I wanted to ask you, what compelled you to change course at a point in your career where you're enjoying such great success in such a lucrative field?

Penny: That's a rich question. And it really has everything to do with the purpose of one's life and what I wanted out of my professional and personal life. When I graduated college, and it was a long time ago, but when I graduated college with an emphasis in finance, banking, and investment banking, those were natural places to go and, in fact, tremendous places to go. because these are big banking organizations with good leadership and interesting opportunities to learn finance and practice and to do deals and to be part of the corporate finance world. And so I entered a management training program and got tremendous experience. One of the things that I most enjoyed about it was I got to learn about so many different kinds of companies and industries because we were doing financing, financing deals for all kinds of different companies. I worked in the south for a long time, I worked in the North for Comerica, and so getting to see different parts of our economy was really exhilarating. There did come a point, though, where- and so many people enter this point in their professional lives where they say, do I really want to do this until I'm 65? And I couldn't answer that question with a lot of passion. I didn't know exactly what I was looking for, but I found the opportunity with Edward Jones on monster.com and I saw two things that really attracted me. The first was the investment philosophy of this organization. We help guide people using financial tools and investments. We help guide people to great opportunities in their own lives, sometimes opportunities they didn't even know existed. And with my finance background, I'm a Chartered Financial Analyst, I recognize the Edward Jones investment philosophy as being a very, very effective tried and true investment philosophy. I believed in that. The other thing that I saw was a business model that enabled me to be fully who I was. And so I'm going to use a term here, I don't mean it literally, to live and die based on the trust and relationship that I was building with families in the community of Lavonia, which is where my branch was, that was very attractive to me, too. I wanted to see what I was capable of in terms of applying some entrepreneurial instincts. Using that investment philosophy to make a difference in people's lives and growing something that I can be proud of. That's what attracted me. And so you characterized it as not exactly the past that would have been the career counseling path straight out of school. I'm not sure. I think the counseling path out of school is to find what you are passionate about, what your gifts, your skills, your purpose as an individual connects you to, because frankly, you're going to spend more time doing that than you are with anything else in your life that you love, and so love that thing. And frankly, that's what I found that with Jones. It's why I'm still here 21 years later.

Adam: Penny, I literally could not agree with you more. And something that I tell audiences that I speak to is that you need to find what you're passionate about. I tell audiences that if you could, number one, find something that you're good at, number two, find something that you're passionate about, and number three, find something that allows you to make a positive impact in the lives of others, you know, you found it, you know? That's it. It doesn't feel like work. So it isn't a matter of whether it is the most prestigious company or whether it's the highest paying job, it's a matter of what resonates with you. And I love that whether it was a job that you found on monster.com, or found through any other channel, this job spoke to you. You applied for it, you went after it, you got it. And what I wanted to ask you is, you spent six years working as a financial advisor before moving into management. And once you're in management, you kept getting promoted, promoted, promoted. And next thing you know, you're the CEO of a Fortune 500 company. And I wanted to know what tips you have for listeners on how to get promoted, how to climb the corporate ladder and how to ultimately make it into the C suite?

Penny: Yeah, well, the first thing that I'm going to say about that, Adam, is I never intended to be in this chair. And the reason that I say that is I didn't come at it with some sort of mental calculus about where I was going to get to or what I wanted to get to. I was pretty diligent about ensuring that my passion and my purpose got enlivened every day. And a large part of enlivening that was looking for opportunities to grow, which meant looking for opportunities to do something new, generally, something kind of terrifying, sort of like jumping off that cliff and becoming a financial adviser after that corporate career. And so each opportunity that I was given at Edward Jones to go into leadership in our regional structure, to volunteer in new ways, and help others be successful, then to move and to move my family, and to move from the Detroit area to St. Louis to something unknown, to come back inside of a corporate setting, then with each subsequent move into different areas of responsibility, what was happening was, I was given opportunities to stretch myself and opportunities, I'm just going to say it really bluntly, to be terrified, because while I knew in general, what that roll was about, and what it was responsible for, at a time I was going into areas that I didn't necessarily have the technical expertise. Oftentimes, I had not done that thing before- that job was supposed to be leading. And so I think what has served me well. I know that’s what's kept my fire lit, is that I didn't have any mental calculus about if I should go into this job, what's waiting for me after that, what am I going to get as a result of that. I also never went into a new role with a sense of conservatism in terms of, well, it's my job just to kind of keep the train running down the rails and take care of this and make sure nothing bad happens. You know, that's part of leadership, but that's not the exciting part. The exciting part is to think with the team about a better future, about an ideal future state for those that we're serving, and then work to gather a team to deliver on that. So I think those sort of tenets; a certain amount of fearlessness. That doesn't mean I wasn't afraid, but a certain amount of fearlessness, a lack of mental calculus, and a desire to really make a difference and make things better. I think that's what has enabled me to have the opportunities that I've had

Adam: Penny, talk a little bit more about the skills that you developed along the way that allowed you to make it to the top and what are the skills that you find are most critical to your success now that you're running a major company?

Penny: Yeah, very broadly, the skill of learning quickly, I think, is becoming even more important in any kind of contribution, and certainly in leadership. I mean, how many times have we read and said, especially in the last year, things are changing at an unprecedented rate? There is no playbook for leadership, where we are today, we can't rely on the rules of thumb that we relied on for years and years. And certainly autocratic, top down leadership is just no longer part of a durable playbook. And so the skills of learning quickly, the skill of being optimistic, and setting an engaging, purpose-driven future view of making things better. And then bringing strategy and technology and purpose people, driven people together, to deliver on that, to get excited about that together and deliver on that. I think those are some of the skills. Communication is really important. Ambition setting is important. Bringing people together is important. And then I'm gonna, I'm going to add one more thing. And I'll use a metaphor that really has been impactful to me; the skill of knowing when to take yourself off the dance floor and fly up to the balcony to thoughtfully and quietly look at what's happening around you, to get out of the fanaticism of the world. As we've said, the world is changing so quickly, everything around us is changing. We've got to respond and react and be proactive. But we also have to quiet things down from time to time, fly up to that balcony, look at the dance floor. Know that the dance that we're all dancing is the right one or change the music or change the steps if what we see is not getting us to that ideal future state. And then at the proper time, go back on the back down on the dance floor. And affect what's happening. We call that working in the business and working on the business. And so the skill of a leader to be able to do that and see it from a horizon level view of what's happening from the balcony on the dance floor. It’s an important skill.

Adam: I truly love everything you said. And as you were talking about your philosophy of what makes a great leader, I was thinking about our conversation off the air when we were talking about our shared love of baseball, albeit, love of different baseball teams. I'm an Angels fan and you're a Cardinal fan. But when you think about a great manager, just like a great leader of any organization, so much of what you said applies- you obviously have to have a pulse of your day to day operations and be able to manage what's happening in the game, the strategy manager, bullpen manager lineup- but so much of it is more than that having a pulse on your clubhouse, having a pulse on how your players are feeling, being able to just take a step back and have a broader perspective. And I really appreciate you sharing that and appreciate that being such a core tenet of your philosophy as a leader. It makes me think about great baseball managers and we’ve had some here. I've read, read and heard, some of their manifestos, some of their ways of leading and good leaders, good managers see possibilities and then create possibilities in other people with other people that might not have been seen or created before there's there's a certain amount of audacity and boldness and fearlessness to it. It all goes back to what's the purpose, what’s the good we're trying to create in the world and just an enthusiasm and excitement for being able to do that together.

Adam: So when Tony LaRussa was managing the Cardinals- and one of my favorite books as a kid was Men at Work which focused on LaRussa’s time managing the A's. Like all managers he was in charge of leading a 25 man roster and a small group of coaches, whereas you lead an official 1,000 person company. What are the keys to managing such a large company and how do you maintain control over your culture in a company as large as yours?

Penny: Well, I'm going to key in on a word that you just used, Adam, and I'm going to rebuff that word; you used the word control. I also bristle when things are written about leaders, certainly about me, that say I run Edward Jones. I don't run Edward Jones, Edward Jones is a partnership by nature of its corporate structure. But we are also an organization that's built on an ethos of partnership, working in partnership with our colleagues, toward our purpose, which is to make a positive impact on the lives of our clients and our colleagues and together to better the communities and the communities where we serve and society at large. And so it's interesting. I don't run anything, I don't control anything. In fact, there are so many times when I'm the least powerful person in the room. And Tony LaRussa used to say this- his clubhouse was run by the veteran players who lived out the culture that described what the Cardinals are. And each team, each company has its own way of being. Our organization has a particular way of being and a particular culture that is around taking care of one another. It's a spirit of pairing of paying it forward of making things better than we found it. And so I don't control anything. But my job is to be the primary embodiment of our purpose. If anybody looks at me, they should see Edward Jones’ purpose in everything that I say and do. Everywhere I am, I should see it in my calendar. I've come to call this the purpose pole. The long pole in the tent determines how big that tent can be, how many people can fit under it. How many people belong under it, who wants to be under that tent is determined by that center poll. And so my job is to set the ambition of this organization, to create the conditions that enable that ambition to be met. And to be that embodiment of our culture, of purpose, of caring, of stewardship, of partnership, so that folks will know what good looks like, and really importantly, Adam, that when I mess up, and when I didn't get it right, when my calendar didn't necessarily reflect that purpose, or the strategy that I set wasn't quite right, that I also be the leader that says that wasn’t right. Can somebody help? Let's help fix this together. I am a leader who is constantly learning and learning with others about how to create a better future for our clients, our colleagues, our communities and society.

Adam: That brings me back to a great line that Richard Riordan, the former mayor of Los Angeles, who I got to know well. Getting back to my days in business school- I was kind of joking earlier in our interview about the business school career centers, but one of the highlights of my MBA experience was a class I took taught by Richard Riordan, and one of his great lines is only a mediocre person never makes a mistake. And it's so evident in your philosophy as a leader that, firstly, we all make mistakes. And secondly, when you do make a mistake, own it, don't run away from it, don't pretend like it never happened, acknowledge it, and learn from it.

Penny: I believe that some of the greatest momentum at an organization can be built when a mistake is made, and when the leaders and contributors who were on the balcony and on the dance floor in terms of delivering that stop and say, okay, what did we learn from this? We had a couple of opportunities to do this last year. And we documented that we wrote it down. And we as leaders go back to it regularly. It was leadership moments for me that I drew on where we succeeded, as well as where we didn't get it quite right. And that forms the playbook. That's what will happen, that's what I say what we learned last year, we can never unlearn. That's what forms a durable playbook the leader can keep going back to. And to your point, that playbook is made up of many, many stakes as it is cesses.

Adam: Penny, what do you look for in the people who you hire? And what are your best tips on the topic of hiring?

Penny: First and foremost, people with a sense of selflessness about what we're trying to accomplish together, pointed toward a purpose that's meaningful that's bigger than any one person that really is about making a positive difference in the world. A person with a growth mindset. Now, this is something that is all over business organizations, community building, if you know Brene Brown, she's talking about growth minded Carol Dweck wrote the book on growth mindedness, a growth minded mentality is absolutely essential because what got us here, what made us successful up to now will not keep us in a position of strength or of relevance and taking care of our clients and our colleagues in the future. So growth mindedness rather than fixed mindedness that sees the opportunity but is willing to take risks and move forward even into the unknown. That kind of person, that kind of skill is essential. And a sense of curiosity, like a fun loving-ness, about that growth mindedness, not as sort of torture, oh, gosh, drag me along, you know, but behind this, no, a sense of curiosity about what can we accomplish together. Those are the kinds of people that we look for, to compete and be a part of this organization.

Adam: You mentioned the importance earlier on in our conversation of managing your calendar effectively, and I wanted to ask you about your daily routine and, in your personal experience, what are the keys to ensuring that you will be as productive each day as possible?

Penny: Well, the first is, have a part of the day that you control because there are a number of days and, boy, last year, you know, you'd begin the day thinking, you know, what was going to happen and it didn't, didn't unfold that way. So I began my day in a pretty similar way every day. I began it with exercise, I began it with a devotional, and I began it with contemplation, and putting 40 ounces of water in my body. So those are things that I can count on every day, that center me, that quiet me down, that leaves me prepared to be there for the other people that are going to be in my life that day. I also do my best to ensure that my calendar reflects my purpose. And so what are the things that only I can do as the CEO managing partner of this organization? What are the things that only I can do? And then what are the things that other people can and should be doing? I should not be doing those things. I also heard years ago, something that was really important to me, a really effective person uses little bitty scraps of time in very effective ways. So if you got 10 minutes before a meeting begins, some people say, I got 10 minutes, you know, kind of kick back, rather than, what can I think about and get accomplished in these 10 minutes? And maybe it is getting ready to be the best contributor that I can be in this meeting that I'm about to go into- but a real thoughtfulness about how time is spent, because once it's spent, it can never be returned to us.

Adam: I love that. I wanted to ask you a question that you're, unfortunately one of the few people qualified to answer. And hopefully in the years to come, this won't be the case. But the question is as follows; as a female leader in a male dominated industry, what advice do you have for other women trying to make it in industries that have been traditionally dominated by men? And what advice do you have for men in industries like finance, or tech, or sports, on how they could be a part of the solution?

Penny: I especially love the second part of your question and so I'm going to answer the first part pretty quickly. The first part is, my answer is no different than anything that I've shared so far. It is to be a growth minded person. Don't have any mental calculus, look for those opportunities to take risks, and be uncomfortable and sometimes being uncomfortable means being one of the only or one of the first in the room and I really strive to get better at being the headline sometimes about me and some of my colleagues. We want that to be different as well. There is also a line that says, if I can see it, I can be it. What that means is, as it says, I got to see me there before I can imagine getting there or desiring to go there. If I had had that point of view, I wouldn't be here. And so I'm asking the women in the room, the people of color in the room, the people in the room who don't look like those who are traditionally in the room, I'm asking you to step forward and put yourself in uncomfortable places, make yourself known and heard to be part of that. Now, the second part of your question is absolutely vital to make the first part of my answer. And that is those who are traditionally in the room, look around, look around at what's happening in the world, look around at the way demographics are changing, look around at your own family, and what you would want for your family, and then open up to the possibility and listen to us, to me, to others, to other who aren't yet in that room. What we know is that by bringing other talented people into the room, the quality of your organization goes up. It's a truism. If you're not searching for talented people, among all of the pools in your organization, and outside your organization, you are diminishing the quality of the talent in your organization. And the second thing is that talented people, clients, consumers, and investors are looking for organizations, contemporary organizations, who understand demographics and understand the desire for people to want to have a place of belonging where they see others like them, and where they see organizations, creating that big tent, where more people can come under and be served and be part of that purpose. So they, by leading those, those of you who have been in the traditional places of leadership, be in leadership in creating that kind of place of belonging, vitality, growth, opportunity for more people for all the quality people who ought to be part of the bargain.

Adam: Penny, what can anyone listening to this conversation do to become a better leader?

Penny: Become a better human being. Leadership is not about leading a machine, you know, our language, our historic Language of Business and organizations is so one of machinery, that sometimes it's one of war. Organizations are not machines, they are social systems made up of human beings with deep desires and passions and fears and ambitions. And a leader's job is to identify the ambition of that organization, and to create the conditions that enable that ambition to be met. And the conditions are all about people. And so as a leader, getting in touch with our own purpose, who we are as people, and being very self reflective about what we're good at, and what we're not so good at. And being leaders and human beings that are worthy of leadership and followership, worthy of partnership, requires us to be better human beings to start with. That takes time, it takes reflection, but it's also a worthy, worthy, near spiritual pursuit.

Adam: Penny, thank you for all the great advice and thank you for joining us.

Penny: My pleasure, Adam. Thanks for having me.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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