Five Things I Look For in Salespeople

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As they say in “Glenngarry Glen Ross,” sales is a tough racket. You need to have a thick skin, you need to be able to work hard, and you need to be a great listener and empathizer. I had spent most of my childhood aspiring to be a professional athlete when I was older, and when it became pretty evident early on that that was not going to happen, I had to resort to a Plan B. But while most of my classmates at Princeton had seemingly mapped this out from a young age – prepared to go into finance, consulting, medicine, or law – I was not so sure about what I wanted to do. I applied for teaching jobs, because I was interested in teaching and being a mentor. I applied for jobs in sports management, because I liked sports and had spent a summer interning with the Boston Red Sox. I applied (and was summarily rejected) to jobs in finance and consulting, because an English major does not get you very far in that arena.


Then I stumbled upon a job for a tech startup in Boston called SCVNGR. The CEO had dropped out of Princeton and gone to high school near me in Boston. The company was doing some very interesting things, and they had posted a sales position with high upside. I was very excited about this because I had always considered myself a hard worker, and I liked the idea that it was within my own hands to “write my own check” based on my work ethic. Some of my greatest flaws are my biggest strengths – namely a keen fear of failure and the everlasting anxiety and drive that accompanies said fear. I had always enjoyed public speaking and did not fear cold conversations. I applied for the job and I was hired. The rest is history – SCVNGR eventually changed its name to LevelUp and was acquired by Grubhub for $390 million, and I set the path for an enjoyable sales career.


Over the years, I have interviewed for various sales positions and I have interviewed and hired people for various sales positions. I don’t have a checklist and the questions I have asked have changed over the years, and what I look for is intrinsically different depending upon the role. But if there are some commonalities that have existed over the years, roles, and differing situations, I have ranked such traits below in order of their importance.


  1. Coachability


No one is perfect. And on top of that, every role and company is different, with different cultures, values, and ways to succeed. The best rep at Company A might look completely different than the best rep at Company B. Those reps might not succeed if they changed jobs based on their own strengths and what it takes to be successful in their respective roles. This means that anyone – including the sales leader – needs to be coachable.


Without coachability, you end up with stubborn people who believe it is “my way or the highway.” They lack accountability and they cherish their ego greater than they cherish their own long-term success. A thick-skinned individual views coaching as a positive – it is a sign that their leader believes they have potential and wants to help them unlock it.


The simplest way to determine coachability is to ask someone about a time they reacted to negative feedback. I also like to give exercises throughout the interview process, render feedback to the individual, and see how they react to it. Do they defend their behavior or are they willing to give an inch? This will show you the willingness of the individual to accept and respond to feedback.


  1. Accountability


Accountability is somewhat of an extension of coachability, because it is generally an accountable person who is open to being coached. An accountable person puts their ego aside in the short term for the benefit of their ego in the long-term. An accountable person recognizes that even when the customer seems really stupid for not understanding something, that the onus is on them for being unable to speak the customer’s language. We are not here to just take orders – you can hire anyone to take an order. There should be an expectation that there will be friction and the right person – an accountable person – blames themself for failure to overcome that friction. They do not blame the customer, they do not blame the marketing team, and they do not blame the CEO or the product team.


Accountability is crucial because without accountability, there is never improvement. You just have the same person who loves taking orders and doesn’t try to figure out why they are unable to take orders from the people who say “no.” The best way to determine someone’s accountability is to ask them directly about their failures and what they learned from them. Do they start pointing fingers? Or can they show moments where they slipped up, learned something, and then used it to succeed?


  1. Honesty


My high school had a mantra that still sticks with me to this day: “Honesty is expected in all dealings.” It was the first line of the school handbook. There was zero tolerance for lying and students were expelled for the smallest of fibs.


It is important to hire honest people. You need honest people so that you can have honest internal dialogue about what is and is not working. Honesty is crucial for real coachability and accountability. A dishonest person messes up KBI’s, gets in their own way, and erodes trust throughout the entire organization.


More importantly, you need honest people because customers deserve honesty. Some of the best compliments I have been given are where customers tell me I was honest the whole time and interested in helping them, not trying to sell them something. It is easy to spot the difference. Even though I am a salesperson, I engage with salespeople all the time who sell me tools or tickets to tradeshows. It is the honest people that I enjoy working with the most. I respect them for their honesty and for painting me a fuller picture. I can see through everyone else. You should expect the same of your client base when you hire in sales.


How to know if someone is honest? Ask them difficult questions. I often find salespeople who, when pressed upon their greatest weakness, will make up some nonsense that is really a strength of theirs. I ask people what is their greatest fear about working for me or at my company. What is something that could make it go wrong? What has gone wrong in the past? How did they adjust? Anyone who pretends that their entire career is rainbows and butterflies is a liar and you should not hire them.


  1. Listening


I was successful early in my sales career because I worked incredibly hard. It did not hurt that I was comfortable giving presentations and had a good communication and writing style. But I was not a good listener. I thought sales was all about making my point, giving my demo, showing everyone how “cool” the thing was that I was selling. Like I said – I ended up OK, but I often think about how much better I would have been if I had adopted a “listen first” attitude.


Sales is not about you. It is about the customer. If you treat the customer like your friend, you end up listening to the customer like you would listen to your friend. You end up asking them the questions you would ask your friend, not the questions you would ask someone to try to corner them into thinking you have a good product. All this to say, sales comes naturally to those who actively listen with a keen, genuine interest in what the customer has to say. For that reason, it is important to hire salespeople who listen. I make sure of this not only in the steps along the interview process, but also to see how someone answers my questions. Are they answering the questions I am really asking, or just giving me what I want to hear? Are they following up to understand why I am asking certain questions? Are they interviewing me, too?


  1. Hunger


Listing this as #1 is not to take away from anything else on the list; of course I always want honest, accountable, coachable listeners. But there is simply not a great salesperson on Earth who is not very hungry. I expect that someone has chosen a career in sales because they like being in control of their own destiny, because they believe in themselves and because they want to make the most of it. Some of the salespeople I have admired the most are very rough around the edges but have given an impression that they would hide a body for the job (N.B. to any lawyers reading this, that was a joke).


Simply put, salespeople require the utmost motivation to succeed. They need motivation to want to be coachable so they can be as good at their job as possible. They are accountable to themselves because they want to succeed and be better, not so they can hide and accept their failures. They do things the way they are supposed to be done because they are constantly bettering themselves and because that is the way they are wired. This is an irreplaceable, must-have trait for the best salespeople.

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