3 Questions I Ask in Every Sales Interview


I love sales people. I am not sure why. Of course they bring in revenue which comes in handy, but it comes down to respect ultimately.

I think I would summarize it down to 3 observations. Good salespeople tend to be:

(1) Social creatures.

They are just so damn easy to talk to. After I talk to them I always hope they will text me later and invite me to the party where the cool kids go hang out (They never do by the way).

(2) Excellent at productivity and efficiency.

They know how to work on a ton of shit at the same time, how to prioritize those opportunities, and how to wrap all of that up into a bow to show their manager how much business they will close this quarter.

(3) Not easily phased.

Most salespeople either are or begin life as an SDR (Sales Development Representative). This means they have “earned their stripes” by calling strangers all day every day for months on end. And a ridiculous number of those calls result in a “no”. And the good SDR’s just move on to the next one. Many burn out. The ones who don’t often move on to more senior level roles. And when you talk to them, they can’t be phased. Their skin is as thick as it gets. And you feel it when you talk to them. It’s an admirable trait, earned, like many admirable traits people develop, by slogging up the mountain of humility.

So we want people like this working with us right? How do we find them? Well interviewing/recruiting is flat out one of the hardest things a startup has to do. But here are 3 questions I try to ask every salesperson I meet for an interview:

(1) “Describe your process.”

Have them walk you through how they manage their day. How many deals do they work on in a day, a month. How do they pick which deals they decide to work on? Where do leads come from? Are they self generated, or given to them by marketing, or both? What you are looking for here is product/market fit from a sales person perspective. Based on the price point, sales cycle, buyer of your product, you should understand if this candidate can fit into your type of sales. Lower volume, higher price point sales vs. higher volume, lower price point require very different sales behavior.

(2) “What do you need to be successful here. We both want the same thing, which is for you to make a huge amount of money because you are exceeding plan. So what do you need to make that happen?”

Don’t let them give you platitudes like “oh a few white papers should do it!” Have them walk you through their expectations and see if they match with your expectations. Beware of the rep that worked at that big name exciting tech company. They are probably used to getting the output of an amazing lead generation machine that has been in development for 3 years. If you are early stage, you likely don’t have that. Make sure they have a plan to generate their own leads if that is what is important to you.

(3) “How would you describe your interaction with your fellow reps?”

You will hear lots of interesting things here but you are trying to detect the existence of the “cowboy” gene. You know, the “I’m gonna rastle me up some customers with whatever messaging I feel like today!” type of rep. They are poisonous because they aren’t team players. Team collaboration is key for a sales team, because collaboration leads to consistency. Consistency in how you communicate with customers, how you position your product, how you de-position your competitors, etc. A collaborative rep is much more likely to not have this “cowboy” gene and will ensure your sales team is improving as a unit instead of one or 2 successful outliers. How do you find them? Well sometimes they will turn their hands into guns and make shooting noises. But assuming they don’t make it that easy for you, one great response is a story of help — when they knew their teammate was struggling, they helped them improve, and then described the outcome of the help.

So those are my three…but what am I missing? What has worked for you?

Originally published at blog.getguru.com