How to Hire a Great Salesperson

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How many times have you hired a new salesperson that looked great on paper, killed it in their interview, and then… meh? 

They might not be terrible, but compared to what they presented when you first met them, they’re just not living up to that first impression. 

Or maybe they are closing tons of sales, but they aren’t following your process, gelling with the rest of the team, or putting any thought into incorporating your company’s values into their job. 

Either way, they wind up not being a good fit. 

But how can you predict that from an interview?

Here’s the thing, hiring is always a bit of a gamble. But the one role that may be hardest to hire for is the salesperson. Most salespeople know exactly what questions to expect in interviews, and they know how most managers want them answered.

The role and culture of sales haven’t really changed much for decades, (which is crazy if you think about it!), and so people still have a very limited view of salespeople during the hiring process. Of course, once they join a company, they’re usually expected to be something else. But too many interviews don’t prepare them or disqualify them for that. 

The other problem during the hiring process is that sales is an especially hard role to hire for. That particular skill set can be really difficult to identify during an interview. 

Managers try to find it using the “sell me this pen” role play, but honestly, that’s a waste of time. Again, it’s too easy to plan for, and that’s not really how good salespeople work. The most success is usually found through a different kind of sales skill set.

Other standard interview questions don’t always make sense for interviewing a salesperson.



“Tell me about a time you had a conflict at work and what you did to get past it.”



That’s a great question for a future manager or for a customer service role, but it doesn’t really make sense for a sales job.



Asking a potential salesperson about how they plan and work through processes is much better than asking how they resolve conflict.



Ask them:

  • how they plan their day/week/month,
  • how they prioritize their leads, territory, and inherited book of business,
  • how they incorporate a new sales process into their habits.

These questions will point out how important planning and processes are to them, and how open and flexible they are with something new. Hopefully, you’ve created and documented proven processes for how you want your salespeople to find and qualify leads, so you want to make sure that the person you hire is able to adapt and adopt those processes that you put so much work into creating. 

Next, because you do want to get an idea of how they sell, roleplaying sales situations can be beneficial. But not the “sell me this pen” scenario. Roleplay a sales conversation in the discovery section, instead of the pitch, of a sales scenario. Make sure they know how to ask the kind of questions that will uncover their prospects’ needs. Anybody can pitch features and benefits. But asking great discovery questions is what separates the “getting by” salespeople from the truly successful. 

After that, ask them to roleplay a situation in which you say no to the sale. See how they respond. This can give you an idea of whether they’re the kind of salesperson that is always looking for only the best fitting clients or the kind that will try to close every single sale, no matter how good the fit is. It will also let you know how they handle conflict in a sales situation.

While asking these questions and going through the roleplays, pay special attention to their soft skills. Being a salesperson requires a higher level of communication. They have to gain trust and rapport, sometimes in a very short period of time, to create lasting relationships with the best kind of clients and quickly and gently disqualify bad leads.

Above all else, listen! Pay attention to the questions they ask. Are they just asking questions about pay and vacation? They might just be looking for any job, whether or not it’s a good fit. But if they ask about specific questions around company values, expectations for teamwork and support, communication between departments, etc., that shows they are dedicated to finding a career, somewhere they would want to work for the foreseeable future. See if they’ve done their homework about your company before the interview. Those are the people you’ll probably want to keep around.

If they knock that first interview out of the park, the next step should be to have them take an assessment. Assessments shouldn’t be used for outright disqualifying potential salespeople, but it can make either a second interview or their onboarding/orientation much more productive. 

And personality assessments will help you find the best way to motivate them and communicate with them throughout their time with your company.

There’s always a bit of risk with hiring. It can be expensive, time-consuming, and ultimately unsuccessful. But if you take a look at your hiring process and see that it’s either a) the same as it is for every other role or b) is the same one people have been using since the dawn of time, it’s time to change it up. 

Asking better questions that is more appropriate for salespeople and finding out how they will actually perform within your company will help take a lot of the guesswork out of hiring your next great salesperson. 

If you still don’t know where to start in your search for the perfect salesperson, or you’d like more information on using assessments for your sales team, contact me here

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