Hiring a professional salesperson too early is like pressing Go on a GPS without first entering an address. How can you expect someone to take you to your destination when you're not even sure where you're going yet?

Entrepreneurial selling--conducted by founders themselves--is a very different beast from professional selling, conducted by salespeople. Entrepreneurial selling is wild and wooly, more improv than scripted. The company and the product are so new that buyers can still significantly influence their paths; in essence, selling and product development occur simultaneously. That means entrepreneurs must be constantly vigilant not to pursue customers whose requirements might send the business off in the wrong direction.

The task for professional salespeople, by contrast, is far more defined and clear-cut. They are trained to internalize the features and benefits of a tried and true product and then pursue a specific type of customer whom they know will buy it. Professional salespeople aren't product developers; they're not building anything besides a network of contacts. They do a deal then move to the next deal. They hunt. They don't farm.

Entrepreneurs generally have good reasons for hiring professionals. They don't like to sell themselves. They need time to work on the company. They figure professionals have special secret sales-guy moves. But if the product and the sales strategy are still in flux, a professional can do more harm than good. You cannot usefully deploy someone else to sell your product unless you already know--through personal experience, trial and error--how to sell it yourself.

In a job interview, a high-performing sales person will test that knowledge. He or she will ask:

  • For the next six to twelve months, who is the key buyer for this product, and what is their pain?
  • What are five stories of people who have bought this product and been successful?
  • What are five stories of failure, and what did you change about the product in response?
  • What are your top three sources of leads, and what is the monthly volume of leads?
  • What are the top five qualifying questions you use to determine whether you are talking to the right buyer?
  • What are the six to ten most common objections you get, and what effective responses have you developed?
  • For this product, what is the best starting point for price negotiations with a buyer?
  • What is the lifetime value of a customer for this product?
  • What are the steps of your sales process? How long does it take to convert a lead to a close?
  • What are the most common failure points in the sales process?

You should seriously consider for a sales job any candidate that asks all those questions. Unless you cannot answer the questions. If that's the case, postpone that first sales hire until you can.