When a Start-up Should Hire a Corporate Executive

Here's how you can tell if a corporate type is ready to make the transition to a scrappier venture.

Seasoned, well-connected executives are very tempting to hire when you're running a start-up and feel the need for experience and contacts. While bringing on a bunch of eager, smart kids has its allure, there always comes a moment when what you crave is adult supervision, a terrific list of contacts, and the confident calm of an executive who has already achieved significant success. These days, there are quite a few such candidates on the market. But shifting from what appeared to me a staid, established corporation to a start-up is a big jump. Does this ever work—and, if it can, how do you tell?

Motive matters

I've hired a number of heavy-hitting corporate refugees. A number worked out; quite a few did not. Certainly my success rate improved over time—not least because I became a lot more thoughtful and inquisitive about motive. Interviewing a corporate counsel, I realized that what attracted him to my new business was a lot of romance around stock options. He didn't want the pace and excitement of building a new business; he wanted a short cut to wealth. He wasn't for me.

On the other hand, I once hired a COO whose prime reason for wishing to leave a big broadcasting behemoth was that he couldn't stand bureaucracies and hierarchies. He wanted to have more impact across the whole business. I asked him to describe to me his ideal working day. What he pictured was so energetic and chaotic, I knew he would fit right in.

Direct action

There's nowhere to hide in a new or small business. Everyone knows who did what and who is responsible. Some people love that; others don't. I've interviewed job candidates who—honestly—couldn't imagine getting, or making, their own cup of coffee. When I asked one candidate how he'd make a decision, he answered that he'd call a meeting. What, I persevered, if everyone was too busy? He looked blank. Making a decision alone, under time pressure, was something he'd never done; even the prospect seemed to scare him. Many corporations effectively disrupt decision makers, with so many layers of authority that everyone forgets how to think for himself or herself. Such executives are expensive and rarely pay their way.

Process orientation

A great asset seasoned executives bring with them is their understanding that (though it can seem regimented), process is liberating. It's helpful to have employees who appreciate that repetition is cognitively easier and more efficient than constant improvisation. Given the right attitude, they can ease your transition from infancy to adulthood. But don't hire them until you, and the business, are both ready for that shift.

And don't go overboard with process. The first start-up I ever joined had an operations guy whose love of "standard operating procedures" was so obsessive that there was even one for using the shower. No company wants to get old before it has had a chance to grow up.

Honest expectations

Many executives are tremendously romantic about start-ups. They've read about the success stories, not the heartbreaks. They are poor judges of risks because they've never taken any. What that means is that they rarely have any idea of what they may be getting themselves into. As much as you want to add experience and expertise to your ranks, don't woo corporate execs; Scare them. Be very clear about big dangers and high expectations. I used to give candidates my 'green beret speech': This is the scariest, most exhausting, confusing place you'll ever work. If that doesn't excite you—don't join.