Back in the Game

You’re hiring, and one of the resumes you’ve received looks like a perfect fit except for one thing: it’s someone who owns their own business, or has in the past. Many hiring managers are hesitant to bring a former entrepreneur on board … should you be?

Some of the reasons we often hear for this concern are:

  • What if they leave us to go back to running their own show?
  • Will they be happy having a boss? Will they be manageable?
  • Are they set in their ways, and do they think they already know it all?
  • Can we afford them?
  • Will they learn from me and then go compete with our firm?

These are legitimate concerns, no question. But there can be a huge upside to putting an entrepreneur to work for you also … here are some considerations to put your mind at ease and help you find a winner:

  • Maybe they’ve already scratched their entrepreneurial itch and learned that they don’t want all the headaches and responsibilities of business ownership. They’re ready to become a teammate and contributor again.
  • Their business ownership may have been a stopgap, transitional stage. Many have lost a long-term job and tried their hand at consulting while they looked for the right full-time fit.
  • Owners can approach business problems from multiple angles. “Think like an owner” has become a business maxim for a reason: in a sales situation they’re more likely to take a holistic approach that considers costs, margins, downsides and fulfillment realities. Isn’t that something you’d love to have in a salesperson?
  • They can be an invaluable resource and sounding board for you as an owner or hiring manager. Someone who used to sign the front of the checks can bring a perspective that’s much broader than that of a typical employee.
  • The “what if they leave?” question can be handled with a well-constructed non-compete in your agreement.
  • If you’re planning to expand, there’s probably no better choice to run a new location, or region than someone who’s been there and done that.

Plan your interview questions to uncover their motivations and address these considerations, and you’ll discover pretty quickly how manageable you can expect a candidate to be. Keep an open mind, because the right entrepreneurs will bring a toolkit that can be a huge asset for your business.