The Most Dangerous Hire

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One important lesson Aylward has learned? Never do the search alone. Your judgment is not as clear and objective as that of your board members. Aylward says that they, along with senior advisers, have a "deeper intuition" about what your company needs than you do. Second, by making the choice alone, you face the risk of "hiring a superhero and finding out this person who now has lots of control and equity is the wrong person," she says.

So whom should you and your advisers look for? "Founders today are looking for someone with marquee value. They want someone who has contacts, products, or services that can catapult the company forward. The vision of the founders could be 'Wow, this is a cool technical product,' but the vision of a new CEO needs to be 'How do I sustain and increase shareholder value?' " she says.

"By the time a replacement is needed, the tasks going forward are a lot clearer than they are at the inception of the company, when the CEO wore all the hats," Aylward says. At that point it's easy to write a job description that can be used not only for recruiting but also as a starting point for interviewing. You can find samples on the Web or ask your board members for job descriptions they've used for searches at other companies.

What's the key to forging a job description that accurately sums up the person you're looking for? "It needs to describe the company as it exists today," says Aylward. And it should detail "the reason the position is open, any major hurdles (stated as 'opportunities,' of course), and the metrics for success. It also needs to describe the forward vision, the corporate culture, the expectations of the teams, the team members who will touch this person's job, the immediate milestones, and the compensation." (For Aylward's comprehensive list of required skills, plus annotated versions of useful -- and useless -- job descriptions, visit www.inc.com/keyword/CEO.)

Of course, the best job description in the world won't provide you with a trusted executive. Only finely honed interviewing skills will do that. Says Aylward: "The founder should ask himself, 'Can I envision this person sitting next to me at a meeting with the press, with the board of directors, and carrying my message?' The candidate who says, 'I really like to get down in the trenches with my people' -- that really means he's a micromanager. If a guy says, 'Here's what you need to do,' that's someone who doesn't listen clearly, and that's a red flag. The guys who get the job say: 'I'm a listener. I'll be a student until I figure out what needs to be done.' "

What if I regret this move later? What then?

According to psychologist Berglas, it's not a question of if you'll regret the decision but rather when. "There is not a founder who (a) will not need to let go and (b) will not have what I call postdecisional regrets.

"I have never not seen it happen. But founders think, 'I'm the only one who's ever done this.' When [Apple Computer cofounder Steve] Jobs brought in [CEO John] Sculley, it didn't work because Sculley wanted to run the show. Sculley said: 'You gave me the gig. Now get out of my way,' " says Berglas. "It's going to be a rough adjustment. Entrepreneurs can't give control to the CEO in a contractual way; there has to be an emotional process. All entrepreneurs need to find a rabbi-type person they can be vulnerable with who's not associated with the company, someone who doesn't need to win or lose. It's healthy to have someone to vent to -- someone who will help you realize that what you're going through is completely normal."

There's no getting around the fact that leaving your company is painful. But don't take your regret as a sign that you've made a mistake, says Berglas. Trust that you're doing the right thing for your company. "I've never heard of anyone replacing themselves too soon. I believe that entrepreneurial management is an oxymoron. There are some people who like to herd cats and other people who like to think of the neatest routes to get cats places. Bill Gates did a wonderful job, but he also did the right thing when he left," Berglas says of Gates's decision to hand over the CEO title to Steve Ballmer in 2000. "Gates wouldn't have lost anything if Ballmer had taken over 10 years earlier, and he would have had more fun."

Jennifer Reingold is a freelance writer living in New York City.

Please E-mail your comments to editors@inc.com.

Related links:
The CEO Wish List
The CEO Job Description
Founding CEOs Versus Second CEOs

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