Interviews may not be worth the time you spend conducting them. They’re certainly not worth all of the time it takes setting them up. Some people you interview look the part and talk the part, but then utterly fail. Rather than write a post about the perfect interview questions to ask, why not approach hiring from the savvy entrepreneur’s perspective. A good entrepreneur will walk with someone to see if they like their personality. A savvy entrepreneur will test-drive a potential hire.


Some companies make up fake projects, while others have employees participate in role-playing exercises to see how they’ll handle stress. BMW, for example, opened up a simulated production line in South Carolina to see how potential employees would handle a 90-minute shift. Whatever the simulation, working a potential hire for 20-40 hours can tell you a lot:

  • The type of questions they ask
  • How often they need guidance and direction
  • The level of their day-to-day writing skills
  • Problem-solving and prioritizing abilities

Some candidates just make sense on paper. They make sense when you interview them. But give them 40 hours to work for you and patterns of behavior will start to show.  As the saying goes, give them enough rope to wow you or hang themselves.

What’s one of the secrets we’ve found in hiring people in a pinch? Hire the good writer. No matter the position, the person that can put their ideas to paper, knowing what to filter and what not to filter, is a person that will be effective at their job. Besides having a potential hire write a few emails and other descriptions for me, I will often ask them self-awareness questions about their writing ability, like, “What are some common grammatical errors that you commit? What are some of the more common grammatical errors you see in emails that bother you?”

Outsourced CFO’s Perspective

As outsourced CFO’s, we love the concept of test-driving. Our business model is exactly that. We provide service to a company and give them the opportunity to work with us part-time. As experienced CFO’s we recognize that hiring employees is the easy part, getting rid of them is a lot stickier. We advocate that all of our clients be much slower to hire than they otherwise would be, and to be much quicker to fire. When you’re running a bootstrapped company, you often don’t have the luxury of being able to make multiple hiring mistakes.