Any classically trained and moderately intelligent sales leader can manage KPIs from dashboards and build sexy Powerpoint decks. Selecting and hiring top talent however, requires equal parts real-world experience and intuitive gut-feel. Some leaders just seem to have an innate “knack” for conducting great interviews. In my opinion, this is where we separate the men from the boys… the women from the girls… the Yankees from the Mets (que the self-depreciating humor of a long-suffering fan of the team from Queens). Have you ever wondered what “outside-the-box” questions or interview approaches other proven sales leaders are using for evaluating potential hires? Well, wonder no more, Quotakillers. Below are the responses given when ten tremendously successful sales leaders were asked to tell us about their go-to interview questions – and the rationale behind them.
Keith Nealon, CEO, Vyze (Former CRO, M5 Networks and SVP of Sales, Eloqua)
A candidate’s resume tells me what they are – I want to know who they are. I ask a candidate to go back as far as they’d like (into their early childhood if necessary), and tell me what they learned growing up. What were their important experiences (good or bad) and what did they garner from them that carried forward into their career? There are multiple reasons why I ask this question. First, I want to see how thoughtful and articulate the candidate is as this question forces them off of any mentally-prepared script. Second, I want to see if they show any vulnerability in their answer – to me, being comfortable showing such is a sign that someone has a high EQ which is essential in leadership. I love hearing stories about how people have dealt with adversity – which, as we all know, there will be plenty of in a sales role. In general, I want to find out if this person has an attractiveness about how they tell their story that comes off as sincere and authentic. This will be important in getting others to buy into them – whether those others are prospects and clients or folks they’ll be managing.
Heather Combs, CRO, 3Pillar Global
I “cut” people who don’t demonstrate two things in early interviews. One – genuine, innate competitive spirit. This can be exemplified through past participation in sports, dance, or anything they’ve done growing up that’s hard-wired the importance of winning into their being. And two – they better want to talk about money. If they feel uncomfortable talking to me about money, I know they’ll be uncomfortable talking to clients about money. I try to probe without revealing what I want the answer to be. I ask questions like “Tell me about what you do when you aren’t in the office?” and “What compensation plan have you seen work best, and why?”
Todd Ilberg, Area VP of Sales, Oracle Marketing Cloud
This might sound like a trick question, but it’s not. I like to ask “What is your favorite website and why?” This one can provide a ton of insight into the person you’re interviewing. The nature of the candidate’s answer will demonstrate how well they think on their feet, show off their creativity, and give them the opportunity to provide some perspective on their personal interests.
Marc Jacobs, SVP of Sales and Customer Success, CB Insights
I like to ask candidates to tell me about a time where they saved an opportunity that they thought they were going to lose. I want to hear how they’ve dealt with a prospect or customer when their back was against the wall. I’ll follow that up with “Tell me about an opportunity that you lost and why?” I want to see if they take responsibility or blame it on other factors. If they do take responsibility, I want to see if they’ve taken actions to improve and insure that they won’t lose again for the same reason. When I’m interviewing a junior-level candidate, I’ll ask them “Why sales?” If they’re looking at sales as a way into the company and intend to transition to another department, they probably don’t have the hunger necessary to survive carrying a quota in a performance culture.
Josh Pittman, VP of Sales, Velocify
When I’m interviewing, I look for “grit” – I want candidates who have a chip on their shoulder and a need rather than a want to win. A question I often ask is designed to determine what’s behind their desire to earn. “Imagine you were to crush a month and make a $20K commission check. How would you spend it?” General answers as to why people want to be in sales are often superficial. “To make a lot of money” seems to be the most common answer. But why? Do they need to make money? That’s a big part of the “grittiness factor” I look for. I love hearing answers like “I need to pay down my student loans” or “I have two kids that need to be fed, clothed, and enrolled in school” or “I have a personal goal of $1MM net worth by the age of x.” Tangible and strategic answers move to the front of the line. If they don’t know what they’ll be coming to work for every day, they won’t be focused and they won’t be successful.
Habib Khoury, CEO, Mass Exchange (Former CEO, g8wave)
There are three main things I’m looking for when interviewing potential sales hires – intellect (you can’t make someone smarter), tenacity, and EQ. One question I use that can sometimes give insight into a candidate from all three perspectives is “How long do you usually spend writing an introductory email to a prospect?” I believe that communicating concisely and accurately in written format is incredibly important when it comes to establishing credibility with prospects and customers. Since the person on the answering end of this question doesn’t know whether I’d be more impressed with a long or short amount of time as an answer, this ask provides a great forum for their EQ to be put on display. I’ll typically be impressed by attention to detail, focus on pre-email research, awareness of how a value prop should be tailored to particular recipients, etc. The actual answer in terms of minutes or hours is somewhat inconsequential. The best respondents however, allude to proofreading and/or spending time trimming the email’s content to it’s minimum viable length – thus making it clear that they are focused on attention to detail and brevity.
Mandy Cole, Founder, The Cole Method (Former Head of Sales, Livingsocial)
Two things I look for outside of a candidate’s fundamental sales and organizational skills are coachability and determination/problem solving skills. In interviewing for these, I like to use the “tell me about a time” technique because I can see if they reference a specific instance versus giving me a canned answer. For coachability, I ask “Tell me about a time your manager gave you feedback to help you improve and tell me what you did with that feedback?” For determination/problem solving, I’ll go with “Tell me about a time when you were over halfway through the month/quarter and you were pacing behind your goal. What did you do to change that?”
William Lupo, VP of Sales, Solera
In my opinion, math validity tests provide a good way to uncover a prospect’s ability to think critically. To start, I ask about their previous years’ earnings, where they stack or rank in their organization, and how their compensation plan works. Then I have them run me through their winning daily/weekly/monthly metrics and the conversation rates they use to achieve success. After that, we reverse engineer their previous years’ earnings based on the metrics they provided. If the results add up to their initial declaration of earnings, then I consider them to be a good candidate. If their results do not match their originally stated W-2, I’ll give them a second chance to get it right. If they take the time to figure it out and do so accurately, then they have integrity and could be a fit. If they refuse or are unable to figure out the solution, then I pass and move onto the next candidate.
Charles Teed, VP of Sales, CAKE
I come into an interview looking for three things from a candidate: 1 – Do they have the “horsepower” to do the job, 2 – Do they have the fire in the belly to do it every day, and 3 – Are they an a$$hole, because if so, numbers one and two don’t matter. Questions I often ask are “Can you please pitch me on the last product you’ve sold?” “Give me an example of somewhere in your professional career that you’ve won or finished first?” and “What is the best example of where you helped a team member to succeed?”
Christi Schaufler, VP of Sales, Spafinder Wellness
My favorite question to ask in an interview is “What was your biggest failure and who was responsible for it?” This shows a lot about how that person handles self-reflection, how a person views others’ perceptions of them, and it also helps to categorize their overall personality. I like this question since it’s not particularly sales-related, and it gives candidates the opportunity to broaden the range of the interview. I’m hoping their answer will reveal that this individual is easy to coach and eager to improve.
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