By John D’Annunzio. 

Hiring the correct salespeople is the most critical action a sales leader can take. It can make or break the company. Properly hired and on-boarded, “A” players will not only exceed their targets, but also will add value in innumerable ways to include assisting with your strategy, go-to-market, and unique selling proposition.


When hiring salespeople, I am looking for intelligence, charisma, optimism, grit, determination, achievement need, an understanding of sales process/buying personas and competitiveness. I measure with profiling, questioning, and pre-employment testing. I am looking for character traits of demonstrated success following a set-back, driven by an intense need to succeed, combined with the soft skills necessary to develop customer relationships. I have found former military and/or athletes are good profiles for sales.

First Things First

The first decision the Sales Leader needs to make is to decide what type of salesperson he/she needs to hire. First ask yourself the question: What role are you in? Do you need Farmers, Hunters, or Assassins? A Farmer works existing accounts in order to increase share of wallet and cross-sell/mine accounts. A Hunter hunts new accounts, does demand-generation and lead conversion from an established marketing function. An Assassin is best suited to a new industry, a new business model or a new eco-system – typically a start-up still trying to determine its product/market fit and its unique value proposition. In each case my process is the same, but I am screening for a different result.


Like all things in business, the best practice is to follow a process. My process is similar to managing the sales funnel we do every day as Sales Managers, whereby there are various steps along the way where I spend more and more time with fewer and fewer candidates delving deeper into their qualifications and the cultural fit. In general, I work hard to develop a relationship with the candidate during the process as often I am recruiting as much as screening and I want the candidate to buy into me as much as the company and the product/service.

Years ago, I picked up a tip in the book, “How to Swim with the Sharks and Avoid Being Eaten” by Harvey Mackay. Harvey recommended to interview sales prospects in all domains where they would sell. In today’s hyperconnected, always on, unified communications world, that means phone, video, face-to-face and a possible social activity. Typically, I will conduct a 30-minute phone screen to review minimum resume qualifications and ascertain if the prospect has the requisite phone skills, intelligence, presence, and charisma to merit a second interview. I typically conduct a 45-minute video interview where I run through a series of behavioral questions as well as share a little bit about myself and the company. Following the video interview, I will want to meet short-list candidates for a face-to-face. That is typically in an office environment. In that meeting, I dig further into the candidate’s background and examine their cultural fit and motivations as well as their ability to sell. If I have a couple of finalists and cannot decide, I may have a final social setting interview, typically over dinner.

After I have a finalist, I will have them interview with a couple of future peers to established cultural fit. This is often a pre-sales engineer with whom they may work as well as either another field sales or marketing person.

Behavioral Questions

Just like in a sales engagement, I ask lots of questions. Examples include:

  • Tell me about your sales process. I am looking for a keen understanding of sales process and hopefully some reference to a framework such as Holden, SPIN, MEDDIC, or Miller-Heiman, strategic selling principles, and buying personas. If I do not get enough detail in the sales process, I will dig to determine if they understand. Most sales are lost due to not covering all the right bases/sales personas and not cultivating enough corporate support. This is a critical point for me.
  • Another critical area for me is ascertaining their achievement need and their determination. I ask for examples of when they were faced with a difficult personal, life, or physical situation, what happened, and how did they overcome? I am looking for GRIT and optimism as a predictor. I recently hired a guy with a young family who overcame colon cancer and has a colostomy bag. I hired another guy who is a powerlifter and tore some muscles only to come back and overcome and achieve new personal records. I inquire as to their athletic background as I like players who still win when playing hurt and who are competitive. That manifests itself in sports.
  • Other questions include:
    • Tell me what it is like to work with you?
    • How do you sell? Relationship, financial, technical?
    • What are your views on the channel? How do you book initial calls?
    • Give me an example of how you penetrated ABC Company.
    • Tell me how you closed XYZ Company. Why did they buy from you?
  • I like to hire learners, so ask about the last book they read, sales webinar, seminar or podcast.

Teamwork, compatibility, collaboration and ethics are very important to me. As such, I often as some of the following questions:

  • Tell me about a time when you experienced a loss for doing what is right. How did you react?
  • Tell about a specific time when you had to handle a tough problem which challenged fairness or ethical issues.
  • When was the last time you “broke the rules”? What was the situation and what did you do?
  • What values do you appreciate the most in a team environment? [You are looking for things like honesty, fairness, openness, transparency, and inclusiveness in your answers.]
  • If we ever got into a bind with a client, would you be willing to tell a little white lie to help us out?
  • What would your current/past manager say makes you most valuable to them? [Besides intelligence, energy or technical and hard skills, listen for clues that point to integrity.]
  • What are the characteristics exhibited by the best boss you have ever had, or wished that you have had? [A person of integrity will mirror those they follow or look up to, so listen for clues.]

Pre-Employment Testing

While behavioral questions and gut instinct are important to me, I supplement that with testing in order to minimize errors and variability. Research shows that successful salespeople share three, non-teachable personality traits: (1) Need for Achievement, (2) Competitiveness, and (3) Optimism. I like to test for sales correlated attributes, i.e., competitiveness, achievement need. I’ve has success with Gallup Strengths BP10 as well as Sales Drive


I always ask for at least three references to include one manager, one peer, and one customer. I insist on the customer reference and prefer two. Why so many? I want to know “What is it like to manage you?”, “What is it like to work with you?”, and “What is it like to buy from you?” Regardless, many candidate references are prepped, friends, and therefore worthless. Therefore, to the maximum extent possible, I review LinkedIn to determine if there is anyone whom we both know so I can get an independent assessment. At HP I hired someone principally on the 17 written LinkedIn endorsements which also helped to overcome the skepticism of the Divisional Senior Vice President.


A final work on diversity. Why? Diverse teams outperform. A 2015 McKinsey report on 366 public companies found that those in the top quartile for ethnic and racial diversity in management were 35% more likely to have financial returns above their industry mean, and those in the top quartile for gender diversity were 15% more likely to have returns above the industry mean. I am always looking for diversity of thought process as teams will perform better.


John D’Annunzio is currently Vice President/General Manager, North America for Cyberbit, the leading provider of cyber ranges. Cyberbit customers include Fortune 500 companies, telecom operators, MSSPs, system integrators, police departments, governments, militaries and higher education institutions, jointly running over 100,000 training sessions annually across five continents.