Who’s The Boss?

Who’s The Boss?


How’s this for irony: “You can’t get out of being a control freak alone,” says Cheryl Cran, leadership consultant and author of The Control Freak Revolution. “I didn’t hire anyone for 11 years, because I believed only I could do it and do it right. I was burning out and my business was stagnant.”

These days, Cran has an assistant and a five-person team, and she outsources web and accounting functions for her business, which includes coaching Fortune 500 companies. “Even if there are multiple reasons to let go, most people need someone they trust to build a case for them,” Cran says. A mentor or business coach can help. So can a good book on the subject, such as Michael Gerber’s E-Myth. In any case, the end result is the same: You have to teach yourself to trust other people. Start small: Hire an assistant – part-time, and hand off the basics, such as scheduling and routine phone calls. Then, let your trust (and the entrepreneur’s natural aversion to admin duties) build.

“I let the first thing go, and when I saw how much more I was able to focus on speaking and writing and adding more revenue streams, I couldn’t go back,” Cran recalls. You should take as long as you need, but in less than a year, Cran’s assistant went from updating a database to planning multi-day workshops. “It’s natural to want to be in control, and a lot of people just haven’t learned the fine art of delegation yet,” Cran says. But remember, those who run successful corporations have assistants to make their lives easier. Why wouldn’t you?

Letting Go

The label gets tossed around a lot, but are you, actually, a control freak? If any of the following statements describe you, Cran says, we’re afraid to say that yes, indeed you are:

  • You’re proud of never taking vacation time
  • You feel angry when others let you down
  • You’re always ‘swamped’
  • People ask you a lot of questions (because they’re afraid they’re not doing it right)
  • You actually believe that no one else can do what you do
  • You check in with employees so much, they look annoyed to see you

Staying In Command

We asked Robert Sutton – Stanford University Professor, author of Good Boss, Bad Boss and the man who coined the term ‘bosshole’ – how to take charge in a good way:

  • Talk more than others – but not the whole time, lest people consider you a bully, or just plain boring
  • Interrupt sometimes (more than others interrupt you)
  • Occasionally cross your arms when you talk, and when in doubt, remain standing
  • Show strategic flashes of anger
  • Let employees know what you like and what you don’t
  • Ask people what they need. And give it to them.
Jennifer Wang
Jennifer Wang is a staff writer at Entrepreneur magazine in Southern California. She’s been writing about business for newspapers and magazines since 2004, beginning with a stint in the publications department of the Federal Reserve Bank of Richmond, where she realized that economics could, in fact, be cool.