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From Employee to Entrepreneur

One woman offers her take on how to make that transition a smooth one.
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Kimberly Bishop has been training to be an entrepreneur her entire life.

She went through a major career change in 2005, leaving a position as a senior leader in a global company in the financial services industry to establish a career in executive recruiting. At the same time, she moved from Omaha, Neb., to New York City.

That change gave her the confidence she needed to consider taking the next step and becoming an entrepreneur. "When I made that first major change, I knew that at some point I would want to do something very entrepreneurial on my own," she says.

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In June, Bishop started her own business, KimberlyBishop.net, a career management and leadership services company, with one part-time employee.

As an expert on career transition and a brand-new entrepreneur to boot, Bishop has some suggestions for employees who want to make the leap to entrepreneur:

  1. Spend time thinking about what is it you're valuing about your own career. That bit of advice comes from the book True Success, by Tom Morris. In his book, Morris notes that when it comes to goal-setting, most people say, "What is it that I want to do next?" What he focuses on is what it is that you want to preserve. What is it that I really like right now and, whatever I do next, what is it I want to preserve?

    Bishop based her business decisions on that philosophy: "I really like leadership," she says. "I really like the idea of doing new things. I like growth-oriented initiatives. I know that I really enjoy living in New York City.

    "Sometimes we overlook the personal things," Bishop cautions. "There's the dynamic of where someone's willing to live and how far they're willing to commute. There's the dynamic of compensation. Those have to be aligned."

  2. If you're an entrepreneur who's hiring, take time to consider whether your location is a barrier to employment, and whether your compensation aligns with what a candidate is looking for. If those things aren't aligned, Bishop says, odds are your candidate will either turn the job down or won't last long as an employee.

    Those considerations can also affect whether you quit your job to start a business or stay employed and do it on the side. How much time do you have in your day? How much is already devoted to other pursuits? For some people, it's feasible to do a part-time business. For others, it isn't.

  3. Are you going to like wearing many hats? If you worked in a large organization, you likely had many resources. As an entrepreneur, you'll find yourself doing things that other people were responsible for in your previous organization, or things you used to delegate. "I'm doing a lot of things myself," Bishop says. "But I'm happy to be doing that." In fact, she says, "This has been absolutely fabulous, and I'm loving every minute of it."

    Bishop says she enjoys having control over her time. "I can prioritize the things I think are most important and the business opportunities I think are most relevant to the top of the list." In a corporation, she says, your time often is dictated around other people's calendars.

  4. Don't be afraid to ask people for help or to seek out resources online and elsewhere. "I went to the bookstore and was looking at books around small businesses. What was really cool is that there were books and DVDs and charts and plans. If you go online, there are lots of resources available. Find them, and don't be afraid to ask."

  5. Don't wait until you start your business to get involved in the industry, Bishop advises. Start interacting with professional organizations and networking groups ahead of time. "People will be happy to help you."

    Bishop is a member of the Committee of 200, composed of corporate members and successful entrepreneurs. "I joined as a corporate member," Bishop says, but she's been inspired by the entrepreneurs. "Join an organization to be around people who have done this. You hear the good, the bad and the ugly. There are no words to describe how valuable that can be."

Appropriate Interview Questions If you're an entrepreneur looking to hire someone, how can you choose the right candidate? What kinds of questions should you ask? Here are a few of Bishop's favorite questions:

  1. What do you value most about the company you work for?
  2. If the individual has been working for a large corporation, ask why he wants to make the switch to an entrepreneurial endeavor.
  3. Can you give me an example of a time in your career when you worked on a project or had an experience that may lend itself to this particular role?
  4. Don't accept the answer, "I think I'd really like this." Have the candidate tell you about going through a similar experience and how she handled it.
  5. Give me an example of something in your career that you're most proud of.
  6. Give me an example of a time you made a mistake and how you might handle that differently. Be concerned if the candidate says, "I've never made a mistake," Bishop warns. "That's a red flag about her own self-awareness."

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