Hiring salespeople is not only one of the most important tasks you will undertake, it is also one of the most difficult. After all, sales professionals are in sales, so having a solid process for evaluating sales talent is key.

“Hiring salespeople is not only one of the most important tasks you will undertake, it is also one of the most difficult.” 

Hiring for an entrepreneurial venture is different than hiring for a large company. It’s not just about skills – it’s also about attitude and the ability to thrive in a fast moving environment. Here are a few of the skills that you should be evaluating in your sales hiring process.

Cultural Fit

In addition to assessing passion and personality for cultural fit, it is equally important to explore sales-specific culture dynamics. Get to know your candidate better and get a sense of how well they’d fit in with your current team, specifically in terms of personality, values and alignment to your goals. These questions really allow people to open up, relax, and share with us more about who they are.

• What’s the last thing you learned that you thought was really interesting?
• What’s something that you taught yourself to do?
• Where do you want to be in 5 years? This question helps us to hone in on how well their professional goals align with our company goals and room for growth in their role.
• What’s something you did recently where you put yourself out of your comfort zone? We especially like this one for sales as it points to their creativity, motivation, and desire to learn and grow. It can also reflect their comfort level with meeting and talking to new people.
• If you could be in movie, which one would it be and why?
• Who inspires you? Who are your heroes?
• What are you most proud of?

Work Ethic and Ambition

It is important to understand how much a candidate is willing to get his or her hands dirty and their level of ambition.

• Strategy vs. Execution. Depending on your product/market, you may need a “figure-outer” as opposed to someone who can crank out 100 calls a day and crush repetitive sales activities. It’s hard to find someone who can do both well, so prioritize what you need in advance.
• Career Ambitions. Often times, we hire sales talent by asking them to make short-term financial sacrifices in return for rapid career growth and/or management duties. Can you deliver on these promises? Can you meet individual ambitions, and are their timelines for growth compatible with your team? Be honest with yourself and the candidate from the get-go to decrease the chances of attrition later on.

Validate Past Sales Performance

It is common for almost all sales professionals to include in their resume a “120% of quota” type reference. Dig into to any sales professional’s past track record. This includes:

• Ask for Details. Have the candidate outline his or her annual sales quota, average deal size, sales cycle, largest deal, largest loss and other details about how he or she achieved their sales target.
• Ask to Talk to Past Sales Managers. References are one thing, but you need to talk to the people that managed this individual and has intimate knowledge of sales performance. If a sales manager is not on the reference list or can’t be made available, it tells you something.
• Ask About Strategy and Tactics. Ask about their annual plan and the strategies and tactics they used to hit their goals. Ask them about their best and worst strategy and tactic and an example of how they tinkered with each to achieve their goal.
• Ask to Talk to Customers. Good sales professionals have great relationships with customers. They should welcome the opportunity to have an advocate of theirs speak to you about the candidates potential.

It’s important to dig into a candidate’s metrics as well as the characteristics of their previous sales process. Probe deeper on qualitative answers, and don’t be afraid to ask interviewees to estimate and quantify so you can check for consistency.

Test Their Industry or Product Knowledge

Simply put, your salesperson needs to be a credible expert in front of your customer. Ask basic questions about their familiarity with your industry and various programs, software or social platforms you use. A candidate’s product knowledge profile can be viewed as a 2 x 2 quadrant of strong and weak at current knowledge and learning ability. Strong/strong and weak/weak should be easy decisions. The other two cases depend on your patience for their ramp-up time and the accuracy of your assessment.

• Current Knowledge. A harsh reality in some sales industries is that a knowledge gap can be too large despite raw horsepower. In industries like healthcare and finance, for example, the sales role can require years of prior experience to be able to “talk the talk.”
• Learning Ability. A great way to test aptitude for learning is to teach the candidate something about your product and then ask them to explain it back to you. You can do it orally on the spot or send them a case study before the interview. Great candidates can master the concept and even articulate new insights. You can also do this exercise using a randomly selected, unfamiliar subject.

See Them In Action

You wouldn’t hire an engineer without seeing their code, so why would you hire a salesperson without seeing them sell? Here are four ways to test their skills:

• Role Play. A rapid succession of tough (or weird) objections can be a great way to test for how the candidate will handle edge cases.
• Mock Pitch. Test a candidate’s presentation and closing ability by having them present a mock pitch to your team of stakeholders.
• Field Day. Ask a potential salesperson to spend a day shadowing one of your reps. Creating controlled environments to have them speak to real prospects is a great way to estimate their ramp-up time.

Catch Them Off Guard

It’s one thing for a salesperson who prepares well to comment intelligently about a topic. It is quite another to see how they react when they are foist in the middle of uncharted waters under the gun. Here are a few ways to do that:

• Ask them where they failed and what they would have done differently.
• Ask them about the last big deal that they lost.
• Ask them about a conflict situation in your company and how they would have handled it.
• Ask them how they would become president of a large company.

You are not necessarily looking for the right answer, but to see their thought process, how accountable they are, and how their values and intelligence impact their answers.

You are not necessarily looking for the right answer, but to see their thought process, how accountable they are, and how their values and intelligence impact their answers.

See How They Build a Plan

For senior hires and big-ticket enterprise sales, your sales person needs management consultant-type skills to help organizations make strategic purchasing decisions and visualize implementation roadmaps. Have your interviewees lay out a 30-60-90-day plan for how they would approach their new role in the company so you can test their visioning, conceptual thinking and presentation skills.

Give Them An Assignment

We also like to ask applicants we see potential in, to do one or more mini assignments. This gives us a preview of their work and work-style and a sneak-peek at how motivated they are.

• Assignment – Phone Skills. Phone us and leave a voicemail. Leave us a follow-up message. We wanted them to do this to see their phone etiquette and what they are able to add to the conversation with a bit more time to think about how they could sell us a whiteboard.
• Assignment – Prospecting. Compile a spreadsheet of ten companies (in a disclosed location) that would be good prospects for us. Give them some specifics to look for, but otherwise leave it up to them to make the call on how well these companies would fit. Have them show their reasoning. This assignment shows their research skills, their analytical abilities, and attention to detail. Lead research and understanding customer fit are major aspects of the SDR role, so we wanted to make sure they had these skills before we offered them a job.
• Assignment – Strategy. Craft a one page sales strategy for a customer set in your target market. You don’t expect them to know everything, but you want to see how thorough and thoughtful they are in the process.

See How (and If) They Ask Questions

Good candidates should have a lot of questions. The way they approach you in an interview tells you a lot about how they would approach a sales opportunity. Most interviewees have questions to ask too – as they should. Asking questions – good questions – shows their instinct to be proactive, a self-starter, their ability to do research, their inclination to be conversational about the process and their overall confidence and perspective of how well-suited they are for this position.

See Their Understanding of the Sales Process and Common Tools

There are a ton of sales tools (e.g., CRM, email tracking) your team may be using that could increase ramp-up time for a new rep. It’s important to understand how much learning a rep will have to do to master your tool suite and be productive. If the hurdle is significant, test their experience, tech savvy and learning speed.

Sample Interview Questions

Here are some sample interview questions that may help you in your process

• What’s your opinion of the role of learning in sales? Being thrown for a loop by this question is a sign that your candidate isn’t a life-long learner, which is becoming increasingly important in sales.
• How do you keep up to date on your target market? Even if the target market of their last job is totally different than that of the one they’re interviewing for, this will show you their ability to find and keep up to date with relevant trade publications and blogs.
• Explain something to me. While this technically isn’t a question, it’s important to assess whether the candidate has a helpful demeanor.
• What’s worse: not making quota every single month or not having happy customers? Depending on your company’s goals, either answer could be the right one. But beware of reps who will prioritize quota over truly giving customers what they need — or withholding from them what they don’t.
• How would you approach a short sales cycle differently than a long sales cycle? Short cycles call for reps that can close quickly, and long sales cycles require a much more careful, tailored approach. They’re drastically different, and your candidate should recognize this.
• When do you stop pursuing a client? The right answer here will depend on your company’s process, but in general, the more tenacious and persistent a rep is willing to be, the better. Trish Bertuzzi, founder of The Bridge Group, recommends six to eight attempts before throwing in the towel.
• Who are you most comfortable selling to and why? Listen for whether they answer with a description of an ideal buyer, or a particular demographic with no tie-in to the buying process. Depending on your product or service, the second type of response might pose a problem.
• What’s your least favorite part of the sales process? If their least favorite part is the most important part at your company, that’s probably a red flag. This question can also alert you to weak areas.
• What motivates you? Money, achievement, helping customers, being #1 — there are a lot of potential answers to this question. What makes a good answer vs. a bad one will hinge on your company culture. For instance, if teamwork is paramount within your sales team, a candidate who is driven by internal competition might not be a great fit.
• What is your ultimate career aspiration? Lack of growth opportunities was one of the top three reasons that would cause a salesperson to look for a new job, according to a survey from Glassdoor. If the candidate expresses a desire to pursue a career move your company can’t provide, you might be interviewing again sooner than you’d like.
• What are three adjectives a former client would use to describe you? Listen for synonyms of “helpful,” as a consultative approach is becoming increasingly important in modern sales.
• How do you keep a smile on your face during a hard day? Appraise the person’s attitude towards rejection. Do they need time to shake off an unpleasant conversation? Or do they bounce back immediately?
• What made you want to get into sales? Commission, while perhaps part of the motivation, is not a great response to this question.
• Have you ever had a losing streak? How did you turn it around? Everyone has bad spells, so beware of someone who claims they’ve never experienced a downturn. Nothing’s wrong with a temporary slump as long as the candidate learned from it.
• What do you think our company/sales organization could do better? This sales interview question serves two purposes: it shows how much research the candidate did before meeting with you, and it demonstrates their creative thinking and entrepreneurial capabilities.
• In your last position, how much time did you spend cultivating customer relationships vs. hunting for new clients, and why? Certain companies and roles call for people better at farming or hunting, but look out for a person who performs one of these tasks to the exclusion of the other. Both are vital to selling well.
• What’s your approach to handling customer objections? Preparing to deal with objections instead of winging it is critical. Listen for evidence of a process.
• Have you ever asked a prospect who didn’t buy from you to explain why you lost the deal? What did they say, and what did you learn from that experience? Following up on deals to learn how to do better next time — win or lose — boosts the odds of winning in the future. A salesperson who takes the time to learn from both their successes and their failures will likely be a valuable addition to your team.
• What role does social media play in your selling process? Social selling is becoming more important in all industries. If the candidate has not used social channels to research prospects or look for leads in the past, make sure they have a willingness to learn.
• What role does content play in your selling process? Again, it’s not necessarily a deal breaker if the salesperson doesn’t actively share and engage with content on their social media accounts, but they should at least want to start doing so.
• How do you research prospects before a call or meeting? What information do you look for? Neglecting to use LinkedIn to research clients is not a viable option in today’s sales environment. Ensure that candidates are searching for personal commonalities in addition to professional information so they can tailor their communication as much as possible. Looking into company trigger events would be the cherry on top.
• Have you ever turned a prospect away? If so, why? Selling to everyone and anyone — even if a salesperson knows it’s not in the prospect’s best interest — is a recipe for disaster. Make sure your candidate is comfortable with turning business away if the potential customer isn’t a good fit.
• What are some of your favorite questions to ask prospects? Salespeople today should be asking questions more than making pitches. Open-ended questions that help a rep thoroughly understand a prospect’s needs are as good as gold.
• What’s your take on collaboration within a sales team? Collaboration might be less important at some organizations than others, but candidates who aren’t willing to collaborate at all won’t likely make pleasant coworkers, not to mention their uncooperative attitude will block knowledge sharing.
• If you were hired for this position, what would you do in your first month? The answer to this question doesn’t have to blow you away. However, the candidate should have some sort of action plan to get up and running. No matter how much training you provide, it’s still smart to hire a self-starter when you can.