“I decided to be the boss that I always wanted to have.”

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Debra Benton is the founder and president of Benton Management Resources and has 30 years of experience as a coach to CEOs and other executives. Her client organizations have included Microsoft, Kraft, McKinsey & Company, Campbell’s Soup, Dell Computer, McDonald’s, Pfizer, SC Johnson, NASA, Time Warner, and the U.S. Border Patrol.

Debra is a speaker, blogger, and author of nine books, including ‘Lions Don’t Need to Roar’, ‘Executive Charisma’ and ‘How to Think Like a CEO’. Her most recent offering is ‘The Virtual Executive: How to Act Like a CEO Online and Offline’ (McGraw-Hill, 2012). Her previous writing has earned her a spot on the New York Times Best-Seller List.

MO: Did you know from an early age that you were interested in being an entrepreneur?

Debra: I didn’t know that specific word but I did know I wanted to work in the big exciting world, do something I loved, and make my own money. My diary entry at age 13 had that written in red ink. It also had ‘I hate boys’ but that one turned out not to be true!

My mother, with love in her heart, had told me ‘you aren’t pretty enough to get through life on your looks so you better develop a good personality and a sense of humor’ which started my interest in the personal and professional development arena that my career has been centered around.

Also, at that time, I remember reading an article that the future stars would be the ‘pink collar’ workers – meaning females — as opposed to blue or white collar workers. And that sounded good to me.

MO: You were only 23 when you started you first company. What hurdles did you face being a female entrepreneur in the 1970’s?

Debra: There were some hurdles and some opportunities at the same time.

The hurdles:
-A young female isn’t always taken seriously…so I made the mistake of trying to act real severe, which made me look ridiculous.
-I had no track record, no big company name, no credentials, really. But I did have common sense an innate understanding of human nature, a unique bit of knowledge based on my research on effective executives, and chutzpa.

The opportunities:
-A young female can sometimes get into business offices out of curiosity on the men’s part if nothing else. Once in I had to prove my ability, but frankly, I could get in when others couldn’t.
-I had no female career role model so I didn’t have someone to compare myself to and I could just make up what I wanted to be — so I decided to be the boss that I always wanted to have.
-I could get away with dumb mistakes because I was forgiven for ‘youth and inexperience’.
-I could make my own decisions.
-I could choose the chances I was willing to take.
-I knew that if I failed I was young enough to start over and try again.

MO: What inspired you to write your most recent book, “The Virtual Executive: How to Act like a CEO Online and Offline”? How was the writing process compared to your previous books? Do you always use the same approach or does it vary?

Debra: I wrote the book because I was in need of the book. I’m the perfect reader for the book as it was essential for me to learn how to translate what I know and teach in terms of being an effective leader when in-person (face-to-face) and make it work equally well when not in-person (the digital workplace). So the book writing turned out to be quite difficult because every single piece of advice was weighed, tested, and challenged by my toughest critic — me. I knew I’d accept no B.S. from a self-help-recipe book and I wouldn’t put that onto my readers either.

As for my approach: Daily I seek out and collect bits of information, facts, stories that stand out to me that others might have interest in. Then I talk to about thirty CEOs to find out what they think about my subject and the same number of potential readers to find out their interests on the subject. Then I start putting pieces of the puzzle together into an organized outline supporting the advice with examples, analogies, and stories to improve the learning. Then I do another round of 30-40 interviews testing what I’m presenting to see validity, interest, relevance and improve upon the content and writing from those conversations. And I repeat that process one of two more times. Finally – eight months later — at one point in time, usually around midnight on a Sunday evening I feel “I’ve finally got it; this is it”. I’m ready to let my book publisher editor look at it.

That’s the writing approach that has worked for me in all my books.

MO: How can self-assessment be a tool for increasing self-confidence?

Debra: Too many times in self- confidence development endeavors it’s all about what you need to do more of, do differently, or do better. You forget to weigh in on all that you already have going for yourself.

To start, write down every ability that you’re proud of about yourself: writing reports, computer games, teaching, following advice, saving money, getting respect from peers, drawing, clipping coupons, dog training, identifying bird species, keeping your word, good grammar, good taste, good judgment, and on and on.

Review your life, your education, your work in a positive light. Seek out the good. Bring to mind past compliments and supportive feedback. Count your blessings for your family, upbringing, and the like.

Don’t take any of those for granted. For most of us, given what we’ve been given, we’ve done pretty well and we need to remember that.

Then, with that your self-assessment:
-Feel neither self-conscious nor superior.
-Feel relevant, never irrelevant.
-Have pride but don’t act too proud.
-Think of yourself less often instead of thinking less of yourself.

MO: How did winning the title of Miss Colorado Teen-ager teach you lessons that you use in corporate America today?

Debra: Admittedly, that was a long time ago but I still walk into a serious and important business meeting humming to myself the theme song of “….there she goes, Miss America….” because it makes me calm down and put things into perspective. I figure if I can walk across the stage in front of thousands of people wearing high heels, and a swimming suit as a scared-to-death teen, then I can walk into any nerve-racking situation as an adult and know how to look comfortable, cool, calm, collected, poised and happy. And frankly, that’s what business is about lots of times: You get the part because you look the part — then later you sure as heck better be able to live up to the part, of course. But first you have to get it and that confidence started from pageants for me. Had there been the opportunity to excel in sports and get that ‘winning’ feeling that would have helped too but those competitive situations weren’t as prevalent at that time as they are today for teen girls.

MO: What advice can you give to someone looking to make a leap in their career?

Debra: You will very seldom regret the calculated risks you take but you sure as heck will regret the ones you were afraid to. So think, study, consider whether you can accept the consequences good or bad – and then go for it….every day. And never, ever, ever give up; just try better and smarter the next time. As I tell my clients, “When the going gets tough, the tough get creative.”