The funny thing about becoming top dog is that there are as many paths to the corner office as there are breeds sitting behind the big desk. Every association’s top executive has his or her own story about what it took to get there. Sometimes it’s the realization of a lifelong dream; other times, it’s simply the next step in a carefully planned career.

But while every CEO takes a unique route, most agree that the more deliberate you are on the pathway, the greater the chance you will succeed. Most also say that no matter how well you prepare, you will still find surprises when you move into the C-suite.

When Deborah Bowen, CAE, became president and CEO of the American College of Healthcare Executives (ACHE) earlier this year, her office itself was perhaps the biggest surprise. “I have my own bathroom,” she says. “I can’t get used to having my own bathroom!”

Carol Vernon, an executive coach with Communication Matters in Washington, DC, says a key part of the journey is clarifying why you want to be a CEO. “Once you know why, you need a vision,” says Vernon, who works with clients on sharpening and presenting their vision, while also helping them with soft skills, such as tweaking their dress and body language.

Here, four association chief executives—two brand-new ones and two veterans—talk about their journey and the challenges that have marked it, from networking and loneliness to office culture and risk taking.

‘A Deliberate Plan’

Bowen didn’t exactly dream of becoming a CEO. But she has always had a passion for association management, and “as you move up,” she says, “you to want to have a larger impact.”

With the exception of a three-year stint at another association, Bowen has worked at ACHE since 1994. She was named ACHE’s executive vice president and chief operating officer a decade ago. To get to the top from there, she says, “I knew I needed to be deliberate and have a plan.”

Before she had a specific CEO job in mind, she hired an executive coach and went through a qualitative 360-degree assessment in which she sought feedback from others on how she was perceived and what she needed to work on. So when her boss and mentor, Thomas Dolan, CAE, decided to retire after leading the organization for 22 years, Bowen had already gathered information about her own qualifications. She also worked on her résumé, conducted practice interviews, and even prepared a PowerPoint presentation about her vision for the organization.

“I was very systematic,” she says. “I had a plan; I had benchmarks. You can’t take anything for granted, no matter how experienced and smart you are.”

Today, Bowen says her biggest challenge in the job is following in the footsteps of a long-term, highly respected CEO. “Have one foot in what people respect and understand about the organization,” she says, “and one foot moving forward. That’s the hardest thing. Because you know things can’t stay exactly the same.”

Opportunity Knocks

From the time he was in college, Thomas Stefaniak, CAE, who became executive director of the Society for Vascular Ultrasound (SVU) last October, has been volunteering and working for membership organizations. He followed his Air Force wife to a few unexpected locales and found work in places where association jobs are few—such as in New Mexico, where he was hired as product development manager at the American Society of Radiologic Technologists (ASRT). That job, as well as his diverse background in the association world—he’s worked in marketing, government relations, and development—was critical in preparing him for his current position.

“I think I beat 250 applicants” for the top job at SVU, he says. “Part of it was that I really understood the medical imaging market already from working with ASRT. At a smaller organization, you can’t afford to take eight to 10 months to get to know the marketplace. I was working with my board on a strategic plan the week I arrived.”

Stefaniak has quickly learned the importance of mentors and having a network of other CEOs. A handful of leadership peers—and others in the imaging community—have been invaluable. “When you’re a little younger like I am,” says Stefaniak, 38, “it’s great to have a network of colleagues to bounce things off of.”

The biggest surprise for Stefaniak, he says, is that there’s no “off” mode—he answers emails late into the night and works weekends. But he considers it all part of the job. “With mobile technology, people are responding to things at all hours,” he says. “Good or bad, I think that’s just the role of the association CEO now, and you have to adapt.”

From Peer to Leader

When Dave Zepponi joined the association world in 1993, after working for his family’s winery and running several companies elsewhere in the wine business, he did so as the first paid employee—the executive director—of the Klamath Water Users Association. At KWUA, he found the political dynamics—both internal and external—invigorating, and he enjoyed solving macro-level problems. “That’s when I really made my decision to be a professional association executive,” he says.

Zepponi joined the Northwest Food Processors Association (NFPA) in Portland, Oregon, in 1997, but when the top executive job opened up four years later, he had mixed feelings about his next move. He was comfortable with his existing position as environmental affairs director, and he loved the teamwork with other managers at his level. Although he’d always expected he’d make it to the number-two position one day, the president’s job wasn’t in his game plan.

“I almost didn’t apply for the job until the interim president had a chat with me,” he says. “His advice was, ‘If you believe you can do this and don’t really go for it, you will kick yourself the rest of your life.’ ” Zepponi talked to each of the managers before he put his hat in the ring to make sure there wouldn’t be any competitive fallout from his decision. But even so, he says he was in an uncomfortable spot.

Zepponi became president in 2001 and has no regrets about taking the plunge, but he knows it changed the dynamics with his peers. “We were a tight group, and then I became their boss,” he says. “I tried to preserve that open camaraderie. But I knew I wasn’t one of them anymore. The biggest transition is that it is lonely at the top.”

Network Support

Donna French Dunn, CAE, executive director and CEO of the Association of YMCA Professionals, first became a CEO of a national organization in Iowa in 1998. One of her first moves was to become active with what was then the ASAE listserver.

“It was all a shock,” she says. “I didn’t realize how much I needed other people. No matter what you think, no matter where you’re coming from, you are never prepared for that first CEO position.”

She says the transition from one CEO job to the next has been easier, although with those moves, she found herself more tuned in to the cultural differences, which can be significant. “You encounter a cultural change every time,” she says, “and the culture—both the staff and the board—can get you. There’s always, ‘We’ve always done it this way before,’ or ‘Why do you think this new thing is a good idea?’ ”

Dunn, who has been in her current position since 2009, says her network has played a vital role in her success. “They’ve supported me, given me advice, and saved me from making mistakes,” she says.

She adds that it’s critical for CEOs to connect with other chief executives in small groups. “Don’t be afraid to reach out to people,” she says. “No one could possibly have all the experience they need, particularly the first time.”

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