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Want to Hire Killer Salespeople? Follow These Steps. When interviewing candidates, first make it casual, then turn up the heat.

By Adam Callinan Edited by Jason Fell

Opinions expressed by Entrepreneur contributors are their own.


There are few things more important to a startup or small business than growing sales, particularly when you're ready to begin scaling. Yet when it comes to hiring salespeople, there are number of signs that are incredibly important to pay attention to but are often missed. These signs are crucial as hiring the wrong person can have a devastating effect on both your brand and bottom line.

These four points will help you better understand how to interview and interpret the response from those who are seeking a job with you:

Make them comfortable. When you're interviewing someone, it's their job to sell themselves to you -- regardless of whether they're applying for a sales position. It's your job to understand who they really are as quickly as possible and cut through the sales pitch. One of the absolute best ways to do that is to make them as comfortable as possible by creating a very casual environment and acting like the interview is no big deal. You're just there to make a new friend.

Related: 25 Wacky Interview Questions That Work

Do not go through their resume in front of them. Actually, when he or she hands it to you, respond with, "I'm not interested in that stuff," and nonchalantly turn it over or place it in a folder. Now sit back in your chair and casually chat for at least 10 minutes about their non-working background. Ask simple followup questions to their responses and you will be amazed what people will openly divulge when they get comfortable.

Understand their story. You might be interested in a candidate based on their previous experience or some incredible letter of recommendation from Bill Gates, but that doesn't mean they are a fit for your team.

Where did they grow up? How many siblings do they have? What's their favorite jelly? Keep the questions coming, and if they have a sales personality, they should be able to talk at length about nearly anything and keep you engaged. If getting them to freely answer questions is equivalent to pulling teeth, the interview is over. Don't waste your time or theirs.

You can learn an awful lot about motivation and work ethic from their backgrounds, particularly with respect to their family situation and how they were raised. Be warned, however, do not ask if they are married or have kids -- that's against the law.

Related: 5 Attributes to Look for in High-Performing Employees

Identify the need. Do they need to work and be successful at sales to live or to keep mom and dad off their back until their trust fund matures? You do not want to hire a salesperson that doesn't have to work, as their "need" is non-existent. You do want to hire salespeople that have the drive and passion for success, particularly when their failure means that they can't pay rent. This is also the point at which you discuss their previous employment, but remain casual -- you're just two friends having coffee.

I'm not suggesting that anyone that comes from a family with money is lazy or bad at sales. There are absolutely circumstances where parents have raised their children to appreciate hard work and forced them to hold a job as soon as they were legally allowed. I'm only pointing out that those examples tend to be the exception.

Now make them uncomfortable. Ask them direct and pointed questions about the wealth of information you just gathered from their rambling. Do not be abusive, but don't hesitate to be abrupt and even interrupt them to throw them off track.

There are two reasons for this: the first is to put them on the spot and get honest answers about their past and abilities, the second is to see how they operate when they're under pressure and flustered.

The sales environment is full of discomfort, interruptions, pointed questions and roadblocks, and it's your job to gather information so you can be as prepared as possible to pull the trigger on the candidate that has the best combination of expertise, history and personality for your team.

Related: To Outsource or Not? That Is the Question.

Adam Callinan

BottleKeeper Founder and Venture Investor

Adam Callinan is a founding partner of Beachwood Ventures, a Los Angeles based early-stage venture capital firm at the intersection of technology and entertainment. As an entrepreneur, Callinan spent nearly a decade building small businesses in and around technology, medical devices and consumer products, which most recently includes an exit in 2013. Callinan lives in Manhattan Beach with his wife Katie and remains active as a founder of BottleKeeper.

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