The Best Questions to Ask if You Want to Hire Great Salespeople

I was taught this interview some years back and it has helped me screen and hire some great salespeople. People often ask me what characteristics I look for when I hire and how to determine whether or not a candidate has these characteristics.

I look for the following characteristics:

How smart are they. Do they listen and can they organize thought and be fast on their feet. I look also look for: Leadership, Character, Work Ethic, How Collaborative are they, Will they work well with a team, Likability, Values Ie money motivation, Ego and Empathy Strength. Acceptance of Coaching. Good Communication and Analytical skill.

The reason I look for these characteristics is that you need to be have certain skills to be great at the complex sale.

First it takes brains. Sorry, but if you are not in the top quarter of the population on the brains scale this might not be the profession for you! The ability to listen, process respond quickly and in the best way possible is a critical skill that people either need to have or need to be able to develop quickly. I look for Leadership not because I want a future manager but because enterprise sales people need ot know how to play quarterback. They have to lead the prospect through a buy cycle as well as their own company through a sales cycle. This is very difficult to do if you do not have leadership skills. Character matters because people like people with good character. People buy from people they like most often. Collaboration and teamwork are required both when selling to the client and when managing resources required to prosecute a sales cycle. Money Motivation is key since this is the reward for being able to be successful at the complex sale. Generally the more money motivated they are the harder they will work. But, as importantly the harder they will try to learn what they need to in order to succeed. A candidate needs enough ego strength to drive a sales cycle and enough empathy to do it in a way that communicates that they care and have the clients best interest at heart. This is a profession where you constantly have to learn and grow and as such the ability to be coached matters.

The question is how do you get after finding out about these characteristics in the interview. I will detail the questions I ask and why I ask them. Hopefully these questions will be helpful to those that want to find great salespeople.

The first question is "Tell me about yourself". I have seen advice on some podcasts of late advising candidates to flip the question as quickly as possible to asking the manager what they want in a candidate. I would not advise you as a candidate to do this. A good interviewer will give you a chance to ask questions. and a good candidate will ask the questions if the interviewer does not offer that opportunity at teh end of the interview. "Tell me about yourself" is being asked for a reason that has little to do with the answer and everything to do with how it is answered. I am looking for listening skill, and the ability to rapidly organize thought and deliver a response. The best answer is to ask "professionally or personally". The other best response is simply to say personally and then deliver a brief description and then say professionally and deliver a brief description. This response means the candidate heard the question, processed it, and responded with a statement that was on point. Trying to flip it to something else means you did not listen well. The probability is that you will not ehar the prospect and talk about your agenda and the prospects.

The next question is often:" If I ask a close friend of yours to give me five adjectives to describe you what would they tell me" The response will not be how the friend sees them but how they see themselves. I am looking for adjectives that support or do not support the values and characteristics I am looking for in a good candidate as noted above.

I will ask them to tell me their greatest strength. In the end this is what they believe is their "super power". This is what they think differentiates them from everyone else. This is what they call on in tough situations. Again, I am looking for something that would support the profile of characteristics I want in the candidate.

The natural follow up question to the above is "what do you consider your greatest weakness". This is in many ways the more important question. Often they will say something like sometimes I work too hard. lol. This of course is a clever way to try and position what they think I will see as a strength as a weakness. My response will be to chuckle lightly and say well that is a disguised strength I really need you to give me a real weakness. Sometimes I get the response I can't think of one. But most times I get a pause, some thought and a true weakness. When this happens I know I have a sincere person who is most likely to take coaching. When I get no weakness or a fast response with no thought its a big red flag. How many people do you know that are open to learning and coaching that have no perceived weakness.

I will ask then to tell me what their greatest success in life was and why? I want to see how they perceive success. Was it all about them or do they describe something that others contributed to. Did they learn anything along the way. Most importantly was it hard! Did they do something that was hard and come out the other end. Selling in the complex sale is hard and it is not for the faint of heart. I want to know what the candidate is made of.

The follow on question is "what has been your greatest failure in life so far and why"? Once again I am looking for what they are made of. Here its about humility and what they learned. Also, how it impacted them and how they came back from it. I want to know if the candidate is resilient. Goodness knows you better be if you are going to take on the complex sale. This question also tends to show how sincere they are and how much to heart they take things. Prospects need to know that their salesperson cares!

I then throw in a question about their SAT scores. SAT'S are really an intelligence test. I ask them about their college grades. I am looking for smarts here. This is not the end all be all because people develop at different ages and at different times. I am also not looking for the top scores. I am generally after the folks in the top 25% of smarts but they do not have to be rocket scientists!

I will ask them to tell me what they like about their current manager and what they do not like. Here I want to know how they like to be managed and if it is consistent with the way I manage and motivate.

I will ask them to describe a difficult sale that they won and why it was hard. I want to know if they have experience with the complex sale or not. I want to know to what level they can perform at as it pertains to the difficulty factor of the sale. Everyone is going to tout their success. However, if the most difficult sale they ever made was not all that difficult then the success they may have had in past jobs may not be reflective of the skill level required for the enterprise sale.

My next question is often, "tell me who most influenced your life and why"? I am after character here. I want to hear what shaped them and why? I want to know that the candidate has integrity and some level of concern for others. I want to see if the person that most influenced the candidate built character. Heck, if they didn't than who did! I also get a real feel for how passionate and human the candidate is. When they speak about this person they are the most passionate, sincere, and honest that they are going to be. I need to feel the passion, sincerity and honesty here because if it does not come through here it never will come through in their selling.

My final question is "most people have a credo or a cliche that describes their philosophy of life, what would yours be? If they seem puzzled I will through out examples like "do onto others" or work hard play hard". I want to know generally how they view others and how they view themselves as it pertains to others. Again I am looking for a team player who can lead and collaborate.

Once the interview is over I thank the candidate for answering all of my questions and I ask them if they have any questions. The questions they ask me give me some insight into their analytical skill. But also how many motivated they are. How they like to be managed and what they do most days in the job.

This is the time to ask what I as the manager am looking for in the candidate. This is also the time to ask about compensation plans, organization, territory, etc. The candidate should be looking to see if the job, management style and culture are a good match for them. The candidate should also try and close me and get feedback from me on how they did and how they stack up against their competition. They should ask if I have any concerns or things they need to address to improve their chances of being hired. How they question me tells me about their analytical skill. their creativity, and how they might question and most importantly qualify a prospect!

When I hire someone they will have interviewed with a peer of theirs and a superior of mine at the least. While this interview can uncover many things getting confirmation of what you believe you see in a candidate from multiple other sources increases dramatically your chances of making a good hire.

The other thing worth mentioning here are some of the absolutely brain dead dumb things hiring managers do such that they miss out on great candidates and often the best candidates.

The first is about who they will see and not see based on the resume. Yikes! The big one is job hops. Job hops can be bad but often they are meaningless and sometimes they are actually good! Yes, if a candidate has not been all that successful in their careers and have a lot of moving around on the resume it is a red flag for sure. However, when there is success and some recent frequent job changes it could be for the right reasons! Successful sales people know what it takes and they don't always stay in places where they find out they cannot succeed. How many companies have systemic issues, how many get sold, how many times is the manager changed? The answer is quite a bit! These are all often legitimate reasons for a great sales person to leave a job. Salespeople leave jobs most often because of the leadership of the company or their direct manager. Those that know how to sell and have been successful in multiple places have lower a tolerance for incompetence.

Another really dumb thing managers that hire for early-stage companies do is consider job hops among sales people that have had success in other early-stage companies. Eighty five to ninety percent fo all early-stage companies fail. A sales person that has had success in other early-stage companies may leave more than one company and have a recent track record of hops because they know that the company is not going to make it before most of the management knows it. Also once an early-stage company is sold the equity play for the sales person is over and they seek the next chance to work for a company where equity is available.

The other dumb thing managers do is put far to much emphasis on references. I am not saying that reference checking is not valuable. There is certainly value if you get information that is valuable and you know how to use it.

When you have an interview process like the one described above you know quite a bit more about the candidate then you do the about the person that is giving you information in a reference check. The candidate is going to give you good references and the people are going to say good things generally. You do not know if these are good people, good managers, or good assessors of talent. Hence the only real value you can get from these kind of references is pattern based data. When you get a similar observation from three different former employers it probably has some merit. But otherwise you know the candidate far better than you know the person giving the reference.

When you blind check or back channel a candidate you know the giver of the information far better. You can dig deeper and generally this is a better source when reference checking a candidate.

Another mistake I see quite often is the over emphasis hiring managers put on knowledge of the space the product is in. Don't get my wrong knowing the space can be helpful but it is far from the determining factor so many mangers make it. The thing that trumps all is sales ability! When a candidate is a great salesperson but does not know the space they are probably smart enough to learn it quick enough to be successful. When you look at a salespersons track record and they have succeeded with other technologies where they didi not know the space at the start chances are really good they will succeed with yours as well!

Finally, there are the hiring mangers who want the salesperson to have "a book". This is most often found in early-stage companies or companies where they are selling into a specific vertical. These hires generally fail at a much higher than average rate. First of all ask them how many times they have sold the same client at multiple companies. The answer is always not many and if they did have a few ask them how many of those they sold three times lol. When you are early-stage you see this as a way to get meetings. Well, you may get meetings but you are not likely to sell much! News Flash lol! You need people that are going to figure out how to take your product to market, penetrate accounts with your value proposition and find your real buyers. The old buyers and formulas used to sell at the last company probably are not going to work for your company. You want people that are going to figure out how to sell your product, to your market, with your value and not someone that thinks they can sell because they have a relationship!

Hiring is the most important thing a manager does! Take the time to figure out how to do it well. There are no silver bullets and no shortcuts. Hiring takes thinking and most importantly a strong well vetted process. This article is about what I have learned. Please add to it if you have other things that work. We can all afford to get better at it!