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Q&A: Karen Kaplan of Hill Holliday

The president of the Boston-based ad agency talks about career advice, mentoring, and the changing nature of the advertising business.

By Sasha Talcott
Boston.com Correspondent / November 4, 2009

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Karen Kaplan is president of Boston-based advertising agency Hill Holliday, as well as president of the Massachusetts Women's Forum, a group of 100 top female executives in the state. She started her career at Hill Holliday 27 years ago and worked her way up through the organization, at times working on consumer, heath care, technology, retail, and financial services markets. She spoke to Sasha Talcott on the topics of career advice, mentoring, and the changing nature of the advertising business.

Q: How did you get to where you are today?

I started at Hill Holliday in 1982 as the receptionist, and my prior work experience included babysitting and waitressing — both of which have come in surprisingly handy. Truly. I'm not kidding. At the time, I wasn't focused on advertising, but I wanted to meet [Hill Holliday co-founder] Jack Connors, and I had heard he was personally interviewing. He had rejected 40 candidates for the receptionist position. Part of my motivation was to see if I could get it, competitively, and part of it was that I wanted to meet Jack.

I graduated college in the early '80s in the middle of back-to-back recessions. I was a French literature major — I wasn't what you'd call well-positioned for a bad job market. I fully intended to go to law school the following year, but I wanted to save money up. But, as Jack Connors tells the story, he never actually paid me enough to go to law school.

I've had the same 12 jobs everyone my age has had — I just had them all at Hill Holliday. I raised my hand for every opportunity I could get. I've run just about every piece of business we've ever had.

Q: What career advice do you have for younger professionals?

I think being confident and optimistic is so important. You have to be really open to continuous improvement. You have to be curious, open and empathetic. These days, in particular, you have to be really versatile.

I just think if you're willing to outwork everyone else, it's not very hard to do, frankly. From the very beginning, I thought, "If I work one more hour a day and a couple of hours on the weekend, I'll pass people who have a 10-year head start on me."

Q: Who were your mentors, and what have you learned from them?

I've had both male and female mentors. Jack Connors has been an incredibly generous mentor to me over a quarter century. After working here a long time, I looked at him one day and I said, "I've been under your roof for longer than I've been under my parents' roof." Jack didn't mentor me in the traditional sense of taking someone under their wing, but I just learned so much by observing him. He allowed me to try things on my own before I was completely ready — and that is a great mentor. I think he believed in me — and him believing in me made me believe in myself.

Anne Finucane [Chief Marketing Officer at Bank of America] is another person where, every time I'm with her, I learn something. Many years ago, she gave me the best single piece of advice I ever got — which is, "You can do it all, but you just can't have it all." That's probably something that connects more with women than men. It's exactly right.

Q: The advertising business is changing dramatically. How is Hill Holliday adjusting?

We're doing relatively well — I can't complain. Our business is pretty good. Some of our peers are really suffering.

The Internet and digital communications have driven very disruptive changes in our industry, but also a lot of opportunities. We're hiring different types of people with different skill sets and different perspectives than we would have hired 10 years ago. Hiring is critical, and so is learning and development. People have to be able to learn and unlearn, which is sometimes harder — to unlearn.

Sasha Talcott is one of five co-founders of a mentoring and networking organization for emerging female leaders, Tomorrow's Women TODAY — The Boston Women's Leadership Council.

Karen Kaplan Karen Kaplan

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