Should You Hire an Entrepreneur?

This week’s blog post is written by Chaloner’s Georgia Aarons. Georgia joined the NY Chaloner office earlier this year. She started her career recruiting for investment banks and Fortune 500 companies before working in London for a PR agency. A graduate of Columbia and Cambridge, Georgia also has a passion for writing and strategic communications. Her recent publications include “Digital Strategies for Powerful Corporate Communications” as well as the editing of the most widely used corporate communications textbook in American Business Schools, “Corporate Communication.”


While many of our clients value entrepreneurial experience (and the bravery, can-do attitude, and profile that comes with it!), others shy away from hiring people who have stepped off a more linear career path. Doing so is a huge risk; after all, 8 out of 10 new businesses fail. But how do you know if a candidate with entrepreneurial history is a good fit for a role? This week, I want to highlight signifiers of a successful entrepreneur and offer questions you can ask in an interview that can help you navigate a candidate’s background and separate the dreamers from the doers.

How passionate were they about the idea, and how successful were they in executing it?
I recently placed a candidate who had been consulting for many years after a career with three different Fortune 100 companies. When I asked him why he had voluntarily left a track he had fought so hard and so long to stay on, he said he had always dreamed of running his own consultancy. I asked him to speak to that experience and transition and he revealed that he spent over a year planning his exit both financially and strategically, waiting to resign until he had three contracts lined up with other Fortune 100 companies. The determination and oversight he brought to the process convinced me that this was indeed, a lifelong career dream, rather than a stopgap.

If it failed, what did they learn?
If your candidate’s new business failed, is that a red flag? Not necessarily! It’s okay to have a candidate who takes risks, but you’ll want to get some details about the circumstances. It’s important to find out if they had a strategy for starting their business, and a really good reason for why it failed. Why are they now looking to leave entrepreneurship and get back in the game? Pressing for some details will not only help you understand their business habits and capabilities, but will also give you the opportunity to hear them speak about key learnings.

Acknowledging the millennial dream
As start-up culture strengthens and the creators of new businesses get younger, hiring managers will see more and more resumes of millennials who have taken risks and have experienced career gaps. One recurring trait of millennials is their appetite and dream to make it big—and get rich—off their own ideas and creativity. There are particular ways to recruit millennials, and it’s important to recognize that what may seem like a risk to you in the career culture you came up in may not be the same for a millennial. While younger candidates may seem riskier, they also are more impressionable and their ambition and work ethic may serve you well.

When it comes to entrepreneurship, it depends on the individual. By asking the right questions, you can quickly determine if a candidate had a well thought-out business plan and strategy, and whether their experience building a business from the ground up could be helpful for a future role.