The Road to the C-Suite

Anita Brick: Hi, this is Anita Brick. And welcome to CareerCast at Chicago Booth. To help you advance in your career. Today, we're delighted to be speaking with Debra Benton. Debra founded Benton Management Resources in 1976, and has been presenting to and teaching senior executives to excel in organizations from McKinsey & Company and Kraft to American Express and Viacom in 18 countries around the globe.

From thousands of in-depth interviews with high profile leaders, Debra has written seven books, including her latest, The Virtual Executive: How to Act Like a CEO Online and Offline. Debra, thank you so much. This is such a treat. We just so appreciate that you're doing this.

Debra Benton: I look forward to talking to you, Anita.

Anita Brick: Lots of interest in this topic of, you know, the road to the C-suite. Why don't we start off with a general question? When you think about the most important things to consider before building a path to CEO or any of the C-suite positions, what do you think those are?

Debra Benton: Well, before and as, I guess I would use, and that is to understand, to embrace the fact that being a technical specialist, brilliant in your specialty, although necessary, isn't sufficient. Simultaneously, you should understand and grasp a generalist view of your work and the company industry, the global economy in general. A specialist and generalist point of view is required.

And the reason is, once at the top, you need to be a generalist. It's the only job that's a pure generalist job. To get there, you need to have some special skill to stand out. If you wait till you get there to get the generalist’s skills, it'll be too late. If you show them all along the way, people will see your potential sooner, you'll be prepared better, and you'll last longer once you get there.

Anita Brick: So when you talk about general skills—in fact, there was a student who asked that question: Should you do them early or late? It sounds like you should be gathering those functional, technical, deep skills and the general skills at the same time. What specific characteristics or traits do organizations look for when they're looking for people in the C-suite?

Debra Benton: It depends organization to organization, and it depends on the point in life of that organization. A startup with two people looks for different things than a traditional blue chip company with 400 million employees. So it's the company, the industry, the time of growth. You know, you should obviously study, research, learn what you can, but you will never know enough until you get in.

And so you have to ask questions. So back to your question about what people are looking for. They want someone who sees things by asking as opposed to telling. They want someone confident, because people don't follow insecure people. And if you are brilliant with your ideas but you lack confidence, people don't like you and trust you. You won't have followers and therefore you won't get things done.

They like people who aren't sycophants. They want someone who is willing to take a risk, which goes back to having confidence.

Anita Brick: It sounds like in addition to the deep marketing skills or the deep financial skills, operations, all of those, I don't want to make it sound too trite, but it sounds like you need to be a good human being. You need to be trustworthy. You need to be able to bring things out of people—and you can do that through curiosity—and you need to build relationships with others within your group, across groups, and to do what you say you're going to do.

Debra Benton: Absolutely. The thing is, in promotions, you get pulled up from above as well as pushed up from below, and people need to remember that being pulled up from above often means you're just so brilliant. You shine, you're a star and they want that. But being pushed up from below is how you deal with other people below you, alongside you and the people you report to.

Integrity. Being a good person, having an inquisitive attitude towards life. It's constantly learning and literally until you die. I have a friend who is so excited. He called me last week and he said, I just signed up for this new class and of course it conflicts with my other class. At 84, he constantly learns.

You have to have a global mindset. Nowadays, that's part of generalist skills. It's not just your knowledge of your function, your industry, your company, your country. It's how it fits into the global perspective. You certainly have to have decision-making ability, the courage to ask questions to get enough data, to have the willingness to make a decision. And then if you're making a mistake, you know how to correct it, rectify the situation, and make sure it doesn't happen again.

I say this about business: It's interpersonal relationships with money attached to it. The same skills to be a good human being make for a good executive. Now that does not mean all executives are good. When you wonder how they got there and they got there, because at some point in time for that company, they feel the need that was necessary and they're still there. So but that's another discussion.

Anita Brick: This is a question—and maybe we'll get a little specificity about some additional skills. There's an alum who said within the next few years I see myself as CFO of a business unit within a multibillion-dollar global corporation. After that point, I would like to move to a CEO role. The problem, though, is that CEOs traditionally do not come from finance in this company.

What experiences should I try to gather while being in the finance function to maximize my chances of being considered for a CEO role later in my career? Would that be different than what you've already said, or would there be additional things?

Debra Benton: That's a very good question for, like you said, specificity, a refinement of my advice. In fact, I think of a CEO client of mine who came up the route of CFO and he said, you know, Debra, the biggest surprise was once I became CEO, I no longer could just fight for the CFO goals and desires, you know, wishes and demands. I had to fight for the CMO, the CTO, the CTO, also as the CFO.

If he demonstrates his or her ability to get along, to influence, to deal well with the marketing people, the personnel people, that's another way of saying generalist skills. But it would be a mistake to just try to be a brilliant CFO while here, hoping that I could be, you know, CEO. By the way, just because it's not traditional, it doesn't mean that at this point in time in your company, it might be just what they need to have a CFO become the CEO again. If the person shows the generalist executive skills mindset and not just his own baby, his own function.

Anita Brick: It's a really good point. There's an alum. She came out of sales and sales management, and went into a strategy role in an adjacent industry. Noticed that the finance function actually needed more perspective from sales and strategy, and ended up becoming director of finance for a very, very large company because that's what they needed at the time. And now she's looking to hire someone because now they need someone who is more of an accounting professional. But at the time, they needed someone, even though she had zero finance experience.

Debra Benton: She's smart on several levels in that she sees what the organization needs as a whole, not just what she wants to do, because that's a basic mistake people make. They think I'll offer the organization what I'm good at. You are smart. If you have something to be good at, and preferably more than one thing that you're good at.

But if you see what the organization needs, what a boss needs, and you fill that need, and that might mean you have to homeschool yourself in areas that you didn't officially study in school, it makes no difference how you get the knowledge. All right, you can get it from a mentor. You can get it from experience. You can get it from the university.

If you get it, you know, utilize it where it's needed. You're what's valued. You're what's needed. And the thing is, if you do that some, they think you're able to do it more. If you do some of this, they often can give you credit for more of it. So what she did was wonderful, perfect and a very good example.

Anita Brick: To follow on to that question about, do you go from a functional area to CEO, another alum said, how does one position oneself or transition from business unit head? And in their company, it's a senior level position to really ratcheting up to the C-suite.

Debra Benton: Again, it is being able to talk the language, understand their problems, give suggestions, points of view, offer help even without getting recognition, appreciation, or reward for it. But it's sort of like becoming your own apprentice as the CEO. I worked with a politician some time back and he was running for mayor of this big city. And I said, now, if you were to become the mayor, what would you be like? What would your day be like? I mean, if you had to stop at the grocery store to get milk on the way home, you know, how can you envision what would go on?

He said, well, more people would know me than I would know. I'd have to have a congenial demeanor on my face. I'd have to have dressed decently. I couldn't ignore people. I certainly couldn't be rude. I'd probably have to shake hands, make some small talk, etc., and he went on describing what it would probably be like if he was the mayor. And I said, OK, from this day on, you start acting like the mayor.

And so truly, from this business unit manager's day on, from now on, he should start acting like—and I don't mean in an arrogant way or you know, a presumptuous or a, you know, unattractive way, but he should think, act, look, behave, interact as if he were running this organization at a C-suite level, because that's how people see you. That's how you get practice and be skilled in it and comfortable in your skin. And again, no one's gonna tell you this.

No one's going to give you permission. No one's going to ask you to do this. You have to take it on your own to do this. Taking control of your career path in your growth. Do not wait for human resources, a headhunter search firms to help you along. You take control. Do not wait.

Anita Brick: Good point. What if you realize you are not going—There was another question actually from an alum as well who said getting to CEO is unlikely in my current company. He is not going anywhere in the near future. How do I gain visibility outside of my firm to be considered for a CEO position in another company?

Debra Benton: Like I'm saying, you should manage your own career program, your own career growth, your own career path. You should manage your own personal public relations campaign.

Anita Brick: So what does that mean in concrete terms?

Debra Benton: Well, OK. Because if you don't get known, if you don't make contacts, if you don't extend your reach outside of your company, your business unit, your industry, no one's going to know you. There is nothing saying that—in fact, I tell my clients every day, five days a week, you can have the weekend off, every day, one time a day, I want you to reach out to someone new that you do not know.

You can pick up the Wall Street Journal and read an article about such and such charity, and you can write a two-line handwritten note, preferably over an email, because everybody else, if they do it, which they don't, but most easily and lazily do just an email, but do a handwritten note on good stationery saying, saw the article in the Wall Street Journal, your work is most impressive, I hope our paths might cross sometime if you're in Denver. Enclose your business card.

One a day. You can write to politicians. You can write to strangers in the newspapers, business people, community leaders. You can touch base with old bosses. If you started with any kind of company, hopefully you know a good company. You probably had a good boss who went someplace, somewhere along the line. Google the person, find him, reach out, let them know what you're doing. Make some contacts. It takes 3 or 4 minutes. Think about it: At the end of six months, you've made lots of contacts. A lot won't respond, but they won't forget. I could go on and on on this subject, and I will if you want me to.

But the point is, take the initiative, reach out, do something once a day. And that's how you start getting because you never know what'll happen. You never know.

Anita Brick: I agree with you. And I think that email of course is great for speed, but it's not so great for building relationships because it's not remarkable. In fact, there was an Executive MBA student who asked, how do I differentiate myself in the marketplace?

Debra Benton: First of all, that is probably the premise of everything I have taught for the last 30 years, and that is that you must differentiate yourself, not to the point of being weird, of course, but I always tell people, if you want to be more memorable, impressive, credible, genuine, trusted, like, comfortable, confident, competent-appearing, there’s one thing you need to do.

And that one thing is to intelligently observe what most people are doing, and then don't do that. There's 1,672 opportunities a day for each one of the listeners and myself and you, Anita, to take more initiative and do things a little differently. And I'm obviously being small with that number compared to what's reality. And you have to differentiate.

Anita Brick: But what are a couple of things that someone can do to differentiate himself or herself, to be viewed as someone with the growth potential, to be in the C-suite?

Debra Benton: Again, not in any particular order. Just randomly think, you know, some things. Aay you show up every day looking like you're ready to go for a job interview. OK, you know, the dress you wear for a job interview. OK. Say you go to work every day looking like that, versus once a month when you have some reason to, you mistakenly think, oh, we're casual dress and it doesn't matter.

And clothes don't make the man. And on and on. All right. So the simple thing of maybe having something superficial, like your dress be more like you're going to see in the corporate suite no matter what your job, what level and who's going to see you, still dress. That could be one example.

Say the company president was pictured in the paper with the governor. All right. He was at some charity event and he's pictured in the paper. The governor. So even if you're a new hire fresh out of college, you could send an email or a two-line handwritten note to the president and say, cut the picture of you with the governor. Proud to be part of this organization.

Anita Brick: It all goes back to building relationships.

Debra Benton: Because all of life is interpersonal relationships, and business is interpersonal relationships with money attached to it. A client of mine was VP of marketing, and said that when he started, he figured 50% of his time was going to be dealing with the people issues, the politics, the interpersonal relationships. You know, who needs to feel good about this or that, he said. I figured 50% of the time I'd have to do that, he said. Once I got on board, I found it was closer to 80%.

The point is, it's all about people, relationships. Another CEO said to me, he said, Debra, if a business issue costs $1 million, if there’s something we're doing that costs $1 million, 850,000 of that cost came from all the communication and the miscommunication and the back and forth with people and making sure we're covering our bases.

Do not think business is about being brilliant with the bottom line alone or brilliant in reading an annual report or putting numbers in the right place. It's being brilliant at putting numbers in the right place, but dealing with people as well.

Anita Brick: For sure. Because when you think about it, there's so much time that you can spend in meetings or nine bazillion emails flying back and forth, people who are able to zero in on the key issue and then articulate it in a way that engages the other people involved. Everything happens faster, and people feel good about the decision after it's done. So totally agree.

Debra Benton: Just add one quick thing.

Anita Brick: Yeah.

Debra Benton: And that is there's some basic principles I always teach. One is do you think differently than others? Like we talked about earlier, differentiating. The other is that your job as a human being walking this earth is to do all you can to maintain the self-esteem of others. If you do that, you will have a very good life, and that means maintaining the self-esteem of others on your team, your boss, your boss's boss, his boss, subordinates, vendors, customers, and maintaining self-esteem means at least you're not the one dinging them.

You don't put them down. You're not critical. You're not judgmental. You're neutral or positive. And if you have to correct behavior, you still do it in a way that doesn't slay the person's self-esteem. And if you follow that rule, you will have a very good life, business wise and personal.

Anita Brick: Good point. Switching gears a little bit, there was an Exec MBA student who had, I think, a really interesting question. Says this may seem obvious, but I have heard time and again two rather conflicting things: one, you need a mentor, a champion to rise to senior management, and two, a mentor, a champion needs to choose you. How do I reconcile these two things and find a mentor or a champion that's going to help me move up?

Debra Benton: It goes hand in hand if you get a mentor, or mentors—I'm all for plural because one mentor isn't going to solve or help with every issue. I myself probably have had 100 mentors over my life. Now, as an older person, I seek out young mentors. I have 20- and 22-year-olds who teach me technology, and I teach them seasoning and leadership.

But the point is, one, you should have plural mentors in my opinion. One, so you don't go to the well too often. Two, because one is not going to be able to solve every issue or help you with every issue; or three, they just not may not be available when you need them. So have multiple, and seek them out. They can be official or unofficial.

Then it is the more you seek out, the more you excel, the more hotshots are going to want to take you under their wing. And so they do come to you. Don't wait until they come to you. You take the initiative. And by the way, from some of those letters that I mentioned earlier, those emails or notes that you can send out, some of those can result in unofficial mentoring relationships.

Anita Brick: Like you don't have to wait for someone to come to you, and having a cadre or an almost like an advisory board is better than figuring that one person who is going to help you forever. Clearly, you're an example that you've done it. You keep refreshing to this day.

Debra Benton: If I have a business problem or an issue that a client has raised, I have a man in Florida that I will pick up the phone. I'll call him. And he's long since retired. He is a very successful, very smart guy, and he enjoys talking about business issues because he's not really doing it much anymore. And so I learn from him, maintaining his self-esteem, which is an OK thing to do.

Again. Good to get older mentors for seasoning in management and leadership development. But older people like myself, my younger mentors for technology. In my opinion, if you have a mentoring conversation, you seek some advice on an issue. The person gives you some advice. You take it or not, but you deal with it. Follow up. Let the person know what happened. Give them that sense of closure about it, particularly if their advice was beneficial and that only feeds their interest to help you more the next time.

Anita Brick: Good point. There were actually three questions. One was from an alum, one from an evening student and one from an Exec MBA student. Three female students who all had a question about, not a lot of women in the C-suite. There is a CEO presence of how CEOs or people in the C-suite should behave. And it's a very male leadership type of modeling.

So how do people—how do women, specifically—strengthen their leadership capabilities so that they can actually break into the C-suite?

Debra Benton: Well, it's true that there aren't a lot of women number wise at the top level yet. I think, is it Fortune or Forbes or somebody? Some magazine every year features like the top 50 women and I think some other magazines. Do you know the top 50 women in technology, the top 50 women in marketing or whatever? The point is, you can look for those lists and you can read their profiles.

You can look at the photographs, you can see if they have any presentations or something on Vimeo or YouTube or something. Even though you have a small group to choose from, you can look and see what they do and pick the best of what you like. You do not have to be a carbon copy. Pick the best of what you like and what strikes you as effective and utilize that.

And by the way, you can pick the best of what men do. Also, the only difference is, OK, it's a man versus a woman. But I mean, effective leadership is effective leadership, period. And so whoever rises to the top is worth looking at emulating, picking what works best for you and trying that out and evolving over time. Grow and evolve as you have more experiences.

Anita Brick: The thing that you said—pick the best and grow and evolve. There was an evening student who had a really interesting question, but I think it actually would fit in nicely. Here it says, what advice would you give a graduate student? What do you think a person should not change as they become a CEO?

Debra Benton: Well, you know, everybody says you’ve got to be yourself. Be yourself. Well, whatever your self is, is what your mama taught you and what your mama taught you may or may not work for the world. You're in this awful society. But maybe your mama wasn't right. Maybe she wasn't the best. Some mamas aren't. As a thinking adult, you can look around, get a standard of comparison of what the best are from what you've learned from schooling, from parenting, from your religious training, from your cultural upbringing.

Pick the best, but then pick what works for where you are. That's what is yourself. My grammar sounds awful here, but that's what “be yourself” means in my definition. It's what you've learned. But it's not just what you've learned. Because sometimes people say, Debra, don't you have to be born a leader? It's all a matter of exposure. And you can garner— you can generate more exposure. I want you to be yourself, but I want you to accept the fact that yourself can and should evolve. But again, with the core of integrity. Maintain others’ self-esteem and you'll do pretty well.

Anita Brick: OK, good. There was a question—there were actually two questions that were asked from the opposite point of view. So one person said, how do I translate senior-level executive experience at a Fortune 100 firm into a C-suite role in a smaller organization? And then another one said, I worked for a startup, where the CEO was also the founder.

He decided to hire a president who was from a multinational corporation. In less than a year, the CEO was ousted. I am a founder of a company. How do I hire a senior manager who can scale up my company without being a casualty, like my former boss?

Debra Benton: First of all, going from a big organization to a small—what you had from the big is structure, process, etc. What you need in the small is, you know, decisiveness, entrepreneurialism, risk-taking ability. So it's kind of the rare person who can go from the big to the small. You will seldom hear of an entrepreneur who goes into a big company, because there's just no tolerance for bureaucracy, right?

If you want to go from one to the other, if you want to attract a person since you're the founder of a company, it really boils down to some intelligence, ego in check, and ability to be resourceful on one's own and not rely on the resources of a big company. And the last question about how do I find a CEO?

It's great if a person had some good exposure in processes and big thinking and a bigger picture and global perspective and on and on that a big company might give you, but the person individually has to have an ego in check where he doesn't have to have, you know, 40 million people reporting to him. He's OK with four people. He knows how to conserve resources, money, manpower, any of the resources. But that's a really big issue. But it's doable. It doesn't happen very often, but it is doable.

Anita Brick: I find it kind of fascinating because I think that there's like a “grass is always greener on the other side” kind of thing going on. Sometimes people believe that smaller is better, or people who are in smaller think bigger is better. It goes back to what you said a few minutes ago. You really need to know who you are and really what you aspire to—not just doing, but what you aspire to be and to then be able to understand what you don't want. Because there are usually fewer resources in a smaller company, at least for a time.

Debra Benton: You have some freedom to move on a dime, right? Have a dime to move on.

Anita Brick: You're right. I remember I was still very, very early in my career, but I had been in a global bank for a few years in my mid-20s. I was head of marketing and strategy for a bank startup, and I wasn't—I know this may sound terrible. I wasn't used to going in and doing my own photocopying, but I did it along with everybody else, along with the CEO, because I was like the ace employee.

You're right. You have to check your ego at the door because there's a little bit of talent for someone coming out of a large organization into a smaller one. How do you convince a smaller company if you are in a bigger company, that it's right for you and it's right for them? Because hiring decisions are so expensive.

Debra Benton: You will have a better chance of convincing and being successful in a mid or smaller size company if you haven't stayed too long. If you've been 27 years at IBM, it's going to be tougher going to a Silicon Valley startup than if you were there 3.5 years. And really, in 3.5 years, you can garner a lot of information and, you know, understand the system and big-company experiences and the benefits and take from the big to the small.

So don't stay in a place too long. That would help. But you know, one thing that I didn't want to skip over when you said the grass is greener, and to tie everything we've been talking about together. So you're in a big company. I think you want to go to a small company because it's very hot. In fact, many people did that with the dot.com bubble years ago.

And, you know, a lot of people lost their whatever because of making that move from a big company because it sounded so exciting. They didn't want to let the parade pass them by. This is why it's important to have continued initiating contact with others. So you have more people in your circle of contacts, some of whom have become mentors, so you can call upon them and say, hey, I'm thinking of going from here to here. Any thoughts, any experience, anything you know of, anything I should be thinking about?

So you see how this all ties together? So it's not just in isolation. We're talking about things, but they all interconnect and overlap and interrelate. By the way, talking about small, I'm all for small. I like small. I really hope you have a lot of entrepreneurs that you're spawning from your university, because we are—I've had my own business since 1976, I know before a lot of your listeners were born. I started very young because I figured if I'm going to fail, I'd rather fail early. It's less costly, financially and emotionally.

So I started my own business when I was 22. I’m all for entrepreneurial spirit and drive. There's a lot of good things about running the show, but you have to be a personality who is disciplined, who is conservative with resources, who is creative and resourceful, and who reaches out to a number of other people. And those same things help you in a big company. So it's like the same advice works for both.

Anita Brick: Got it. Do you have time for one more question?

Debra Benton: I have as much time as you want.

Anita Brick: Excellent, excellent. If you are considering building a path to the C-suite today, what are three things you would advise someone to do? Whether it's online or offline?

Debra Benton: Build the contact of connections and not friends through Facebook or LinkedIn alone. I mean, that's OK to do that as a supplement, but it is not a substitute for personal contact. Making connections, being able to talk to people, get their advice, get their opinion, get their experience and help them with what they might and have a need in. So one is build that social connection—again, not through social media. I want to emphasize that.

Anita Brick: It's real life to life. Right?

Debra Benton: Right, right. Yeah. Two, be a student of the world, meaning constantly learning—and learn about things you're not necessarily interested in. Most of us learn what we're interested in. We pick up magazines. If we like to motorcycle race, we pick up motorcycle magazines, and we go to motorcycle races on the weekends. And we have motorcycle gear and we have motorcycle buddies, kind of like motorcycles.

But it would also be good to pick up a science technology magazine. Be a student of the world. I was on the private plane, you know, the CEO of a company. It happened to be an underwear company, men's underwear, and all his magazines were women's magazines. And I said, why do you have all these women's magazines?

He said, because women buy the men's underwear. OK. So he wanted to know what women think. Find out what others think, what they know, outside of your interest. Three, be confident and have a congenial expression on your face, because you never know who you're going to talk to, who you're going to meet, who you're going to be able to influence. And if you don't look confident, competent, comfortable, they will steer clear of you. And a relaxed expression on your face helps with good posture.

Anita Brick: Great. Debra, thank you so much. It sounds like you've had quite the adventure in the last few decades with all the people that you've worked at and had some amazing experiences. So thank you so much for sharing that with us.

Debra Benton: Well, and it's been a pleasure to talk with you. Your people ask very good questions and thank you.

Anita Brick: Thank you. There's tons of stuff on Debra's website. It's www.DebraBenton.com. One of the things that you'll find is The Virtual Executive, which is her latest book, How to Act Like a CEO Online and Offline. And thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth. Keep advancing.