How to Hire for Sales: Resources and Interview Questions

11 min read

It is a job seeker’s market right now. Good talent is hard to find. But if you “treat your recruitment process like a sales process,” (as Kathleen Votaw puts it), you can find and attract the best talent today. In this “Guide to Hiring,” we’re going to cover everything from the job description to onboarding. And just as you have a process for marketing, qualifying, and attracting the right type of customer, so should you have a process for marketing, qualifying, and attracting the best candidates. And we’ll help you build it.


There are two kinds of sales roles in most businesses, hunters (business development, outbound sales) and farmers (account management). In our industry, most of us tend to recruit for both in the same role. We hire salespeople to land new accounts but then also grow these accounts and it’s difficult -but worth it- to find that unique talent that is qualified to do both as they represent two different skill sets:

The sales driver is someone who is driven, ambitious, and zealous. Their main job is opening and closing new opportunities, driving new business growth. This type of person values exceeding goals, establishing new relationships and above all, winning.

The account manager likes to win too but in a slightly different way. They too are responsive and detail-oriented, they love being the hero and growing sales through relationships. They value positive feedback, consistency, and happy customers, but they are adaptable enough to pivot and deal with problems.

It is possible to hire for both roles, we simply have to ensure that we have a solid, documented process that will guide us toward the perfect candidate.

Before we get into the details, have you documented your hiring process? You should codify your steps so that you can create an action plan for hiring, following is an example:


The Hiring Process


  1. Phone Interview (Pre-screening)
  2. Assessment
  3. In-Person Interview
  4. Emailed/Chat Interview
  5. Team Interview
  6. Sales Proposal/Business Plan
  7. Off-site Interview
  8. Offer

You can alter these as you wish but it’s helpful to know you have a documented plan for each step along the way.

Now on to recruiting and hiring.

Jack Daly, a leading world expert in sales training, said that when you are recruiting for sales you must “recruit for skills but hire for attitude.” But first, how do we ensure we recruit for skills? And next, how do we hire for attitude?


How to Recruit for Skills


Remember that when it comes to hiring for sales, don’t take things at face value and don’t trust your gut (yet). Kathleen Votaw, author of the book Solve The People Puzzle: How High-Growth Companies Attract & Retain Top Talent, is an expert at hiring salespeople and said in a recent podcast with us,  “Salespeople are naturally charming—they typically look good, sound good, and dress well. They are likable people. But do they have the stamina to go the distance and grow your revenue?”

Entrepreneurs often think that because they’ve built a successful business, they can adequately assess the skills it takes to build their business going forward. But times change and as your business grows, you require people with different skillsets. Besides, an entrepreneur’s opinion is restricted to their own limited perspective, limited to their particular experience of success, which relies on a host of contingencies, some of which are not necessarily repeatable. By developing a sales qualifying process, you keep your opinion (your gut instinct) in check, and you rely on your experience to guide you, but do not let either become the sole basis for your decision.

When hiring for sales, what we don’t want to do is make assumptions. Salespeople are generally good at selling themselves. After all, you’re considering hiring them based on their ability to quickly connect emotionally and to understand what motivates the client. Since salespeople are excellent at selling, we have to establish a process that allows us to remain outside of the subjective process dominated by persuasive personalities, and peel back the layers to discover experience, grit, and determination.

There are more and more resources available to leverage technology to help you with your candidate search and qualification. AI is becoming an instrumental tool in recruiting, enabling you to find more qualified employees faster than ever before with tasks like resume collecting and parsing, candidate ranking, and matching. And pre-screening assessments will take the guesswork out of the hiring process and free up your time to focus on the human elements that are vitally important: assessing soft skills, understanding a candidate’s needs, story-telling/selling the role, negotiations, establishing rapport, etc.

Some of the most popular assessments are  ProfileXT, Predictive Index, and Prevue. Also, Myers-Briggs (who our VP of Sales, Samantha Kates highly recommends), has remained a popular assessment to determine how people perceive the world around them and make decisions, here’s a quick and easy version called the Genius-Style Assessment.

Assessments are an objective way to review a candidate’s thinking style, communication skill, behavioral traits, and interests, and will give you an objective report to compare your candidate against the ideal performance model to determine how well suited they may be for the role.


How to Hire for Attitude


In Mercer’s Global Talent Trends Study, they highlighted three attitudes that employers have about three different levels of employees: the loyal attitude, the engaged attitude, and the thriving attitude.

The loyal attitude is that workers are assets to be retained. The engaged attitude is that employees are assets to be acquired and optimized. But the thriving attitude is that employees are value creators to grow and leverage. As a sales leader, this last category is unequivocal: salespeople are value creators and we are looking for those who thrive on creating value.

The next part of the hiring process involves the interviews. Since your assessment will provide a framework for job compatibility, the interview is best used to assess past experience and analyze for soft skills and attitude. Kathleen says that it’s critically important when hiring salespeople to not only asses their ability but to make them “Prove it!” and the interview process is the perfect tool.

After an initial phone screening to prequalify, and the assessment, you’ll want to begin the in-person interview process. We’ve provided twenty open-ended questions to get you started with your sales interview. One suggestion: Some of these questions are intense and require thought. I would split these questions into a two-part interview, one set of the questions asked verbally, one set asked through email or chat. Why? We live in a world dominated by written communication, and language is a salesperson’s primary tool. You want to see how your candidate responds with both verbal and written skills.


Twenty Interview Questions for Sales


  1. Tell us about your last memorable successful sale.
  2. Tell us about a time you rescued a project from disaster with a client.
  3. Tell us about a time when you lost a major account or lost a big deal that you had hoped would come through. What did you learn from that experience? How do you think it shaped you?
  4. Tell us about the most difficult client you’ve ever worked with. How did you learn to work with that client?
  5. Tell us about two extremely different clients that you’ve worked with, what were their personalities like? How did they prefer to communicate? What was your in-person interaction like? How did you learn to pivot from one personality to the other?
  6. What’s the most complicated product or service that you had to sell? How did you communicate this to clients? What did you learn about communicating your product/service to clients?
  7. How big were the transactions you sold? What was the time frame from an open opportunity to a closed deal? What did you do along the way to nurture this process?
  8. Can you tell us about a time when you took a calculated risk with a client? Can you tell us about a time when a risk bordered on recklessness? Or when you took a risk that failed? What did you learn from these experiences?
  9. What do you think was the biggest mistake you’ve made in your sales career? We’re not looking to disqualify you from our pool of candidates, we want to know you’ve made mistakes that have helped you learn.
  10. How do you research Prospects? Clients? Projects? What did you learn about us in your research? What did you learn about our industry in your research? What did you learn about advertising in general?
  11. Tell us about a time when you were able to map your client’s needs to a solution that really amped your client’s results.
  12. Tell us about a time in your career that required intense collaboration with colleagues, what was that like? What was your role? How did you work with your colleagues to achieve your goal(s)?
  13. How did you identify/qualify good business from bad in your previous role?
  14. What were your annual sales numbers? Profit? Growth percentage?
  15. Tell us about some of your sales in the last six months, what did you sell? How did you identify the lead? Did you source it or did someone else source it for you? What tactics did you use to close those sales?
  16. What are your core values? How would your clients describe you? Another way of asking this is, “What is your superpower?”
  17. What was the high water mark for your career? What do you think contributed to your success? Who else was important to your success?
  18. You don’t have to answer this question but do you have any personal hobbies you want to share with us?
  19. What do you enjoy the most about sales?
  20. What do you dislike about sales?

In addition to the interview process, we highly recommend you ask your final candidates to put together a business plan or a sales plan. Good salespeople are self-starters and even though they might have much to learn about your business and the industry, they can still put together a rough idea of how they will go find and develop a book of business. Asking them to put together a plan also creates a rough draft blueprint for you and the sales rep, serving, in a sense, like an employment contract or at least a tacit agreement on the type of work required. It also helps kick-start their thinking about what they must do to achieve success.


Jazzed by Chaos


Lastly, there are so many skills and traits that we could encourage you to watch for but there’s one skill, above all, that is the most critical. As every reader of this article knows, the promotional products business is surprisingly intense. Multiple products, suppliers, a variety of projects for clients: the myriad can be overwhelming. That’s why one trait you are looking for is those who -in Kathleen Votaw’s words- are “jazzed by chaos.”

Kathleen stated, “With talent acquisition … the question for a company becomes, how do you screen for the right people to work within that environment? The people you need, love change and thrive in an environment of chaos. Seek people who are ‘jazzed by chaos’ …. It is valuable for a company to have employees with a kinetic nature because they innovate and participate eagerly in the new ideas of the company. This is, however, a particular kind of person … As a company, you must screen for people who are jazzed by chaos and unpredictable environments. No day-in-and-day-out for them. If the person you are employing does not thrive on change and innovation … that person will never work out for you.”

It’s not that the business is truly chaos but it is complex, with fast moving parts, and it requires the ability to shift, from one project or product to the next. This skill, to thrive amid the complexity is crucial. Above all, we are looking for candidates who can excel in this environment. Catherine Graham, President at distributor RIGHTSLEEVE loves to hire candidates from the hospitality industry for this reason, they are used to high demand clients in a fast-moving industry and can juggle multiple tasks at a time. This is largely a skill but predominantly an attitude: a willingness to pivot.


Never Forget: They are Interviewing You


Finally, remember that as serious and as thorough as a good interview process is, you want this to be also as relaxed and comfortable as you can make it. Inject your process with your own vibe, your humor, your uniqueness. The candidate is interviewing you along every step in this process, they ask themselves questions like: Do I like this person? Would I enjoy working with them? Do I like this company? Is this a business I can respect and a role I can thrive in? Will I enjoy my work?

When I was interviewing candidates for distributor sales, one of the first things I would tell them is that the interview process is two-way, I’m interviewing them; they are interviewing me, and as such, they should feel comfortable asking me or any member of my team anything.


So there you have it, essential steps and critical resources you can use to hire for sales roles. Do you have additional ideas you can contribute to this process? What have you learned about hiring for sales that you can share with the community? Hit us up on social @commonsku! 


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