This article answers the question on two levels. First, the questions the hiring side should ask a sales candidate. Then, the questions a strong candidate will ask the company — which are also the toughest test of the quality of your hiring process. Because if the company can't answer them, the problem with the interview isn't the candidate.
The questions to ask a candidate for a sales role
The questions that work in a sales interview ask for specific episodes from the past, not skills performed on the spot. Behavior in real sales that have already happened is a far more reliable indicator than any charm, smooth talk or improvisation exercise. Research on personnel selection points the same way: in Schmidt and Hunter's synthesis of 85 years of studies, the structured interview — the same questions, anchored to real behavior, for every candidate — shows a predictive validity for job performance of 0.51, against 0.38 for the unstructured interview [1]. Later meta-analyses confirm that it is the structure, more than the interviewer's talent, that makes the interview a reliable tool [2].
Does "Sell me this pen" measure anything useful, or just the candidate's theatrics? It measures the ability to carry a scene — which is not the skill needed to manage a real negotiation with a real customer.
Five families of questions, each with its own purpose:
On past results. "How was your sales target made up in your last role? To what extent did you hit it, and how?" The key words are made up: the share of new customers versus existing ones, average order value, margin as well as revenue. A salesperson who has really managed a target knows its structure; someone who answers only with round, triumphant percentages is probably selling, not reporting.
On the sales process. "Can you walk me through a recent deal, from first contact to close?" People who have a method describe it naturally: how they qualified the customer, what objections they ran into, how they decided when to push and when to let go. People who don't have one stay vague or put everything down to instinct.
On lost deals. "Can you tell me about an important deal you lost? What happened, and what did you do afterward?" Sales is a job made largely of rejection: this question shows how the candidate handles frustration, whether they analyze defeats or bury them, and how honest they are in a situation where the temptation to embellish is at its highest.
On generating opportunities. "In your last role, who found the customers?" A salesperson used to working leads supplied by marketing and one used to sourcing every opportunity on their own are two different profiles, neither better than the other. The answer helps you check compatibility with the way the company generates opportunities — a point we'll come back to later, because it assumes the company knows.
On the reason for changing jobs. "Why are you leaving — or why did you leave — your current role?" Not to judge the answer itself, but to see whether it is consistent with the rest of the story. Someone who moves only for the promise of higher earnings will tend to move again at the next promise.
The questions a strong candidate will ask the company
The best sales candidates assess the company with the same care the company uses to assess them: they have alternatives, and before accepting they want to understand the conditions they'll be selling in. Their questions are predictable — and they are valuable information in both directions.
Is a candidate who asks no questions about the role a good sign or a bad one? Almost always a bad one: either they have no alternatives, or they haven't yet understood that selling conditions matter more than the promised commission.
The four most common questions from well-prepared candidates:
"Who finds the customers?" This is the question that separates serious sales offers from the ones that put the entire burden of lead generation on the salesperson without saying so in the job ad. If the honest answer is "you find them yourself," say it explicitly: it will attract fewer candidates, but the right ones.
"What onboarding is planned?" An experienced candidate knows that without training on the product, the customers and the internal sales process, the first months burn through motivation and opportunities. A vague answer ("you'll learn on the job") is a red flag for them.
"How is the company positioned against its competitors?" Selling for a company that is well known in its market and selling for an unknown company are two different jobs. The candidate wants to understand how much of the persuasion work the brand has already done and how much will fall on them.
"What happened to the person who held this role before?" If the sales team turns over often, the candidate will find out anyway: better a transparent answer in the interview than a surprise in the first month.
These questions have one thing in common: to answer them well, the company must already have done work that has nothing to do with the interview. And this is where most sales hires are really won or lost.
The interview can't save a role that hasn't been defined
In the experience observed in companies — this is a working hypothesis, not a measured figure — a large share of sales hires that go wrong don't fail in the interview: they fail earlier, when the company opens the search without having defined the responsibilities, targets and sales process the new salesperson will fit into. With a vague role, even the best questions produce answers that are impossible to assess — because there is no yardstick.
How do you assess whether a candidate fits a role nobody has described? You don't: you choose on likability, and likability is exactly the ground on which an experienced salesperson plays better than the person interviewing them.
The symptoms of an undefined role are easy to recognize. The job ad talks about the company and the "growth opportunity" but doesn't say what the salesperson will have to deliver. The sales target is a wish ("grow revenue") with no numbers, territory or segment. The question "who finds the customers?" gets different answers depending on who you ask. The business owner is looking for "a salesperson" without having decided whether they need someone who opens new markets or someone who develops existing customers — two jobs that rarely live in the same person.
Under these conditions the interview becomes a ritual: you meet candidates, collect impressions, and pick the one who was most convincing. And the person who is most convincing in an hour of conversation is, by the very nature of the job, the salesperson most skilled at selling themselves — not necessarily the best fit for the role. The interview turns from an assessment tool into the weak point of the process.
The fix isn't better questions, but doing the upstream work first: defining the role. On how to structure the responsibilities and decision-making scope of a role, read how to define the responsibilities of a role.
Define the sales role before you open the search
Defining a sales role means answering a few concrete questions in writing, before you publish the job ad: what the salesperson must deliver, which process they fit into, with what targets and with how much autonomy. It's a few hours of work that changes the nature of every interview that follows.
How much time does a company spend defining the role, compared with the time spent on interviews? The proportion is often upside down: weeks of interviews for a role defined in five minutes.
The minimum elements to put in writing:
The expected output. Not "sell more," but exactly what: win new customers in a given segment, develop existing customers, cover a territory. The choice between opening and developing is the most important one, because it selects different profiles.
The process the salesperson fits into. Who generates the opportunities: marketing, a structured company activity, or the salesperson themselves? Who prepares the quotes, who handles after-sales, who will they need to coordinate with? An excellent salesperson placed in a nonexistent process produces mediocre results — and leaves.
The targets and their time horizon. Realistic numerical targets, with a ramp-up over the first months: no salesperson, however experienced, performs at full capacity from day one on a product they don't know.
The scope of autonomy. On discounts, payment terms and non-standard deals: what they decide alone, what they agree on with others, what needs approval. It's the point that generates the most conflict after hiring, and almost always the least discussed in the interview.
With these elements in writing, the questions in the first section gain a yardstick: the candidate's answers are compared with a real role, not with an impression.
Assess with objective criteria and a repeatable test
A sales interview produces a reliable decision when the assessment criteria are defined before meeting the candidates, every candidate goes through the same structure, and impressions are written down immediately, not reconstructed days later. Repeatability is what makes candidates seen at different times comparable. Levashina and colleagues' systematic review of the literature on structured interviews indicates that standardizing questions and rating criteria reduces bias in the interviewer's judgment [3] — a point that matters all the more with candidates who, by trade, know how to manage the impression they make.
After five interviews in two weeks, what do you remember about the second candidate? Almost nothing precise: without a written template, the final comparison rewards whoever was seen last or left the most vivid impression.
Three measures make the assessment sounder without weighing down the process. First: a template with the role's criteria (experience in the segment, sales method, fit with the company's process, handling rejection), filled in right after each interview and before any verbal discussion. Second: a second observer, because a skilled salesperson builds rapport with whoever is in front of them, and two independent perceptions are harder to charm than one. Third: a practical exercise on the company's real product — a short simulated negotiation with objections typical of real customers — identical for every candidate. It isn't meant to measure product knowledge, which the candidate can't have: it's meant to observe how they listen, how they handle an objection, how they react when they don't know.
Finally, references matter for sales roles more than people think: a direct conversation with a former manager — about how the candidate handled difficult deals and periods of weak results — is more informative than any self-assessment in an interview.
This structure isn't specific to sales: it's the vertical version of a hiring process that applies to any hire. For the full picture — hiring stages, choice of contract, recurring mistakes — read the guide to hiring employees.
After the choice: onboarding the salesperson
Hiring a salesperson doesn't end with the signature: it ends when the salesperson can handle a deal on their own with observable results. The onboarding period is the part of the process companies neglect most often, and it's also where the largest share of well-made hires is lost.
What results can a salesperson left alone in the first months produce? Few, and for the wrong reasons: they don't know the product well enough to defend its price, they don't know the customers well enough to qualify them, and the pressure of a full target pushes them to force deals that needed time.
Three elements make onboarding a salesperson effective. Real shadowing in the first weeks: visits and negotiations carried out together with someone who knows the customers and the product, first as an observer and then with roles reversed. Progressive targets: a first period devoted to learning the product, the customers and the process, with reduced, stated targets that grow toward full capacity. And check-ins scheduled in advance, where you review ongoing deals together: not to control, but to catch early the signs of an onboarding that isn't working — or of a role that, when put to the test, was defined worse than it seemed.
FAQ
Does it make sense to ask the candidate to "sell me a pen" during the interview? No, if the goal is to predict future performance. The improvised test measures theatrics, not the ability to run a real negotiation. Questions about sales that have already happened and a structured simulation on the company's product, identical for every candidate, are more reliable tools: research on personnel selection shows that structured interviews predict performance better than improvised ones [1].
How reliable is the interview as a hiring tool? It depends on how it's conducted. Meta-analyses on the validity of employment interviews indicate that structured interviews — the same questions, criteria defined in advance, written ratings — have significantly higher predictive power than unstructured ones [1] [2]. A free-form interview, run on impressions, remains one of the tools most exposed to errors of judgment, especially with candidates used to selling themselves.
Are references really useful for a sales role? Yes, as long as you check them through a direct conversation and not through written letters. A phone call with a former manager about how the candidate handled difficult deals and periods of weak results produces information the interview can't provide, because it describes behavior observed over time rather than narrated in a situation of self-selling.
Is it better to hire a candidate with industry experience or a good salesperson you train on the product? There's no universal answer: it depends on the role defined upstream. If the company's process generates opportunities and the sales cycle is short, a good salesperson can learn the product. If technical credibility with the customer is decisive and onboarding isn't structured, industry experience carries more weight. Make the choice in writing, before you open the search.
Conclusion
So what should you ask in a sales job interview? Real sales episodes, how past targets were made up, lost deals, how the candidate found customers. And what to expect the candidate to ask: who generates the opportunities, what onboarding is planned, how the company is positioned. These are questions you can only answer well if the upstream work has been done.
Because the interview is the most visible link in the hiring chain, but not the decisive one. A sales role defined in writing — output, process, targets, autonomy — turns the interview from a likability contest into a comparison between a real need and a real person. Written criteria, a repeatable test and structured onboarding do the rest. It's a process within reach of any company: it takes less time than a bad hire, and far less money.
Sources and references
[1] Schmidt, F. L., & Hunter, J. E. (1998). The validity and utility of selection methods in personnel psychology: Practical and theoretical implications of 85 years of research findings. Psychological Bulletin, 124(2), 262–274. https://doi.org/10.1037/0033-2909.124.2.262 — Foundational reference.
[2] McDaniel, M. A., Whetzel, D. L., Schmidt, F. L., & Maurer, S. D. (1994). The validity of employment interviews: A comprehensive review and meta-analysis. Journal of Applied Psychology, 79(4), 599–616. https://doi.org/10.1037/0021-9010.79.4.599 — Foundational reference.
[3] Levashina, J., Hartwell, C. J., Morgeson, F. P., & Campion, M. A. (2014). The structured employment interview: Narrative and quantitative review of the research literature. Personnel Psychology, 67(1), 241–293. https://doi.org/10.1111/peps.12052 — Foundational reference.