Leadership Lessons: Maine Today Media CEO Lisa DeSisto

Lisa DeSisto
Lisa DeSisto

Lisa DeSisto ‘85 (College of Social & Behavior Sciences) is CEO of Maine Today Media, Maine’s largest media company, which includes the Portland Press Herald and the Maine Sunday Telegram, among other properties. Previously, she held a variety of leadership positions at The Boston Globe, including Chief Advertising Officer and General Manager of Boston.com.

When DeSisto took the top job at Maine Today in 2012, the media industry was steeped in digital disruption, which continues today. Her first challenge was to create a digital business model.

“Maine has one of the oldest populations in the country. People love print. They love to sit down with their morning coffee and read our papers cover to cover,” she says. “We needed to improve the print product and offer an incredible digital product, too, but not force a digital migration.”

How did she do it? Here are her four key leadership lessons.

Personality. For me, success is about work ethic, and I inherited it from my parents. My dad was a milkman, and that industry was disrupted by supermarkets. He had to work really hard, and he instilled the same work ethic in me and my siblings. I think it starts with that. I never said, “I want to be in charge! I want to be the leader!” I got along with other people. I have an energetic and enthusiastic can-do attitude, and I’m telling you: It’s my emotional intelligence that has helped me be successful.

Ambition. You’ve got to go beyond your job responsibilities. If you’re just doing what’s listed in your job [description], figure out ways to get involved. Be an informed citizen. No matter where you are in the company, understand how all aspects of it work. Show up at company events. Volunteer for projects after-hours. And above all, stay close to your customers. Understand your customers. I do a lot of email communication with our subscribers to understand their problems and how we can improve upon them.

Always be learning. Stay curious. Network like crazy. And as you progress in your career, make time for those just starting out. Mentorship is so important.

Assertiveness. While many employees struggle to gauge how assertively to act in any given situation, in my experience, women in particular are often too accommodating when negotiating for themselves. Women often search for middle ground and try to problem solve. When negotiating for yourself, the middle ground can work against you, though it can be helpful in other aspects of your personal and professional life.

Be more demonstrative, not in a “too pushy,” entitled way, but in a confident way.

When negotiating for an employment package, a candidate might say, “Do you think I could possibly get an extra week of vacation time?” Instead try, “I will need three weeks of vacation time.” The former makes it too easy for the prospective employer to say no.

Balance. I don’t want to miss anything related to my family life. When I moved from Boston to Maine, I achieved a much better work-life balance. My commute is 22 minutes, no matter what. I gained back at least two hours a day because the traffic is so predictable (there is none) in Maine. We live on a farm with alpacas, goats, and a barn cat. Caring for the animals is a perfect way to downshift from a job in a challenging but critical industry. It’s a totally different lifestyle. People need to get to their kids’ baseball games. If you’re responsible for your work, there’s no reason to miss out on the game.

Interview has been edited and condensed.