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Hiring a Salesperson: 25 Questions to ask

A person who has great sales and negotiation skills will find open doors in lots of companies, in any industry and country. For a Sales Professional a job interview is a real test, because this time it’s not about selling a product or a service. The product that they need to promote to a Hiring Manager is basically themselves, let’s call it “Brand Me”. How well is this salesperson able to emphasize the good points and steer clear of the others? Candidates will have to show right from the start how good their skills, experiences, personality and motivation are.

What are the four most important character traits of a top performing salesperson? Apart from having full product/service knowledge it is crucial to be persuasive, persistent, likeable and highly self-motivated.

These are some questions which will help you to unmask the truly indomitable salesperson. When hiring a salesperson, it’s not just important to ask the right questions, but also to know how to interpret them correctly.

  • What do you know about our product line/service?
  • What do you dislike about most sales?
  • What kind of rewards are most satisfying to you?
  • How do you plan your day?
  • How well do you accept disappointment?
  • How do you feel about out of town/overnight travel?
  • I would be interested to hear of a time when you proved yourself to be more tenacious than your peers.
  • Please describe a specific time when you greatly exceeded the norm.
  • What percentage of your sales calls result in sales?
  • How long does it typically take you from initial contact to close the sale?
  • How do you turn an occasional buyer into a regular buyer?
  • What was the sales volume when you started? What was it when you left?
  • How do you go about securing new prospects and clients?
  • What kind of people do you like and dislike to sell to? How do you manage to sell to these people?
  • What steps are involved in selling your product?
  • Tell me about your most difficult sale and how you approached it.
  • What was the most surprising objection you ever received, and how did you handle it?
  • Sell me this pen.
  • Give me an example of a sale that was, for all intents and purposes, lost. How did you turn the situation around and make the sale?
  • Have you ever sold anything over the phone?
  • What special skills or techniques are necessary to be successful over the phone?
  • Tell me about a time when you called a complete stranger on the phone. How did you start the conversation?
  • How do you go about gathering names of new contacts on the phone?
  • What is your personal most successful sales strategy secret?
  • What will you do if I hire you?

If you want to put your candidate through a more rigorous test you might consider applying the following strategy:

  • Don’t respond to your scheduled telephone call. See what the person’s reaction is.
  • Send an email by addressing the candidate with the wrong name. Wait and see what the candidate does.
  • During the interview ask the person to hold a presentation in selling the company’s product/service. (How confident does the person sound? How familiar is the candidate with the company’s products/services?)
  • Invite the job applicant for lunch. See how the candidate talks and acts outside an office environment. (Would you really want to do business with this person?)
  • Write a rejection letter. What is the candidate’s response to it? (Does the person still try to turn the situation around?)

The goal of this whole exercise is to find out in a real life scenario, how tenacious and keen the person is to close the deal. Don’t just rely on asking sales-related interview questions, instead try to put the candidate in different situations. This approach will make it easier for you to make the right hiring decision. 

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Karin Schroeck-Singh is a passionate Public Speaker, eBook Author, a Career Blogger at and a freelancing Online Content Producer. She has an MBA from the University of Leicester (UK) and gained 18 years of international work experience in Italy, the UK and India.
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