Best Interview Questions to Ask Sales Candidates
Sales interview questions to ask candidates, written for the hiring manager's side of the table, including the founder deciding for the first time what questions to ask when interviewing a salesperson. They run from openers on motivation and rejection through quota history, prospecting, discovery, objections and closing to role-plays, work habits and fit. The guide covers which questions to ask a sales rep in each round and how to check the numbers afterwards.
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The questions
Each question, and why to ask it
Openers
What got you into sales, and what has kept you in it?
Why ask it
Few people planned on selling for a living, so the first half is usually a story about an accident, a nudge from a manager or a bill that needed paying. The second half matters more. Someone who can say what still holds their interest after years of targets that reset to zero has thought about the work, and a shrug suggests they are in it by default.
What do you know about our company, what we sell and who buys it?
Why ask it
Researching a stranger before a conversation is the job, so this is a work sample as much as a courtesy. A prepared candidate can name your product, a likely buyer and a competitor or two. One who has only skimmed the homepage may well prospect your market the same way.
Walk me through your sales process, from the first contact to a signed deal.
Why ask it
Have them tell it through one real deal, since a process described in general comes out as a list of stage names. Notice which steps they linger on and which they skip. The skipped one, often qualifying or the paperwork at the end, is usually where their deals slow down.
What motivates you most in this work: the money, the win, the customer, or something else?
Why ask it
There is no wrong pick, only a wrong match with your comp plan and your sales cycle. Someone who lives for the weekly win will be restless in a nine-month deal. A candidate who insists money never matters to them is probably guessing at what a manager wants to hear.
How do you handle rejection, say a full week of hearing nothing but no?
Why ask it
Skip past "I don't take it personally" and ask what they did on the Friday of their last bad week. The useful answers are routines: a set number of calls before lunch, a walk, a debrief with a teammate. Claiming that rejection never stings suggests little cold outreach, or an answer shaped for the interview.
Why do you want to sell this product, for this company?
Why ask it
A rep has to believe in the product enough to recommend it to strangers day after day, so a vague answer counts for more here than it would in most jobs. The convincing ones mention a customer of yours, a market they already know or a product they have used. If the only reason is that you are hiring, ask what else they are interviewing for.
Why are you leaving your current sales job, and what would have kept you there?
Why ask it
A territory cut, a comp plan rewritten mid-year and a product that stopped selling are all fair reasons, and each can be checked against the numbers they give you later. Be wary when every past employer was at fault. The second half shows what they will expect from you within a year.
Which part of selling do you like least?
Why ask it
Prospecting, paperwork and chasing signatures are the usual confessions, and any of them is fine if this job is light on it. What matters is the workaround. The rep who dislikes cold calls and blocks the first hour of the day for them is a safer hire than the one who loves everything.
What do you do better than most of the reps you've worked with?
Why ask it
Hold on to the answer and test it against everything else they tell you. If they say discovery, their deal stories should be full of questions they asked. If they say closing, the quarters should show it, and "relationships" needs a customer who bought twice or followed them to a new company.
Track record
Take me through your last four quarters: quota, what you closed, and where you ranked on the team.
Why ask it
Strong performers know these numbers without checking, including the bad quarter. Watch for attainment quoted as a percentage with no quota attached, or an annual figure that smooths over two missed quarters. Mention at this point that you will be asking their references about the same figures.
What was your number made of? How many deals, and what was the average size?
Why ask it
The same annual figure looks entirely different at four large deals a year versus sixty small ones, and those are different jobs. Ask how many of the deals they opened themselves. A year that came mostly from one inherited renewal says little about how they close.
Take me through your biggest win. What would have happened if you hadn't been on that deal?
Why ask it
The second half is the real question, because it forces a claim about their own contribution. Good answers name a specific intervention: reaching a second buyer, catching a competitor's misinformation, restructuring terms. Weak answers describe a deal that was going to close anyway.
Tell me about a deal you were sure of and lost. What did you miss?
Why ask it
The second question asks for their own error, and some candidates will not give one. If every loss comes down to price, a product gap or procurement, expect to hear the same explanations in your pipeline reviews. The most believable answers tend to involve a person at the buyer they never got to.
Tell me about a quarter or a year when you missed your number. What happened, and what did you change?
Why ask it
Anyone who has sold for more than a couple of years has a miss, so "never" means a short record or a selective memory. Give credit for a cause they could act on, like starting the quarter with too little pipeline, and for a change that showed up in the next period's results.
How long was a typical sales cycle in your last job, and who were you selling to?
Why ask it
A rep used to closing in one call has to relearn patience for a six-month cycle, and a long-cycle seller can stall when asked to close forty small deals a month. Compare the buyer's seniority and the deal length with your own before assuming the skills carry over.
What was hard to defend about the product you were selling?
Why ask it
Everyone has sold something with a gap in it. Candidates who claim their last product was flawless are either not paying attention to buyers or are managing you. The good version names the gap and explains how they handled it without lying to the customer.
Tell me about the most difficult customer you've had. How did it end?
Why ask it
Listen to how they talk about the person. Contempt for a demanding buyer tends to leak into calls, while a rep who can explain what the customer was worried about usually kept the account. Ask whether that customer renewed or bought again.
Which of your customers would speak well of you if I called them, and what would they say?
Why ask it
Managers are the standard reference, but a buyer watched the candidate do the actual work, so the names should come quickly. Whatever they expect the customer to say, whether honest, fast or persistent, is also their own picture of how they sell. Agree with the candidate before contacting anyone.
Prospecting
Where did your pipeline actually come from: inbound, your own outbound, partners, marketing?
Why ask it
Plenty of reps who hit quota have never built pipeline from nothing, which is a problem only if that is what your job needs. Push for rough percentages. If the answer is "a mix", ask how many of last quarter's deals began with a call or an email they sent cold.
Here's a company we'd like as a customer. How would you research it before a first call?
Why ask it
Name a real account you are chasing and give them a minute to think, which turns a claim about preparation into a demonstration. See whether they get past the website to who has just been hired, what the company has said in public about its plans, and which person they would call first and why.
It's Monday morning and your pipeline is empty. What do you do in the first two hours?
Why ask it
A scenario with a clock on it gets you actions where "how do you prospect" gets a philosophy. Hope for a list they would build, a reason for who is on it and a call made before ten. If the two hours are all planning, ask when the first conversation with a buyer happens.
How do you decide which accounts or leads get your time first?
Why ask it
Every rep has more names than hours, so the sorting rule is the skill. Good ones lean on signs that a buyer is in the market: a new executive, a funding round, a rival's contract coming up for renewal. Working the list alphabetically, or by whoever replied last, is no rule at all.
What does your outreach look like: how many touches, on which channels, before you stop?
Why ask it
Ask for the real sequence, day by day. One email and a voicemail is giving up early, and twenty identical messages is a good way to get filtered as spam. The candidates worth hiring change the message each time and can say when they call it.
What's a cold email or opening line of yours that got replies, and why do you think it worked?
Why ask it
Have them recite it or pull it up on their phone. A message that worked is short, about the buyer and easy to answer, and the rep who wrote it can explain each line. If all they can offer is the marketing team's template, they have not been writing their own.
How do you qualify a lead, and what makes you rule one out early?
Why ask it
Budget, authority, need and timing are the textbook four, and reciting them proves little. Press for the exact questions they ask on a first call to decide whether there should be a second. Reps who qualify loosely look busy in the pipeline review and thin at the end of the quarter.
What do you do when a prospect who seemed keen stops replying?
Why ask it
Every seller gets ghosted, so there should be a practised answer. Strong ones try a different channel or a different person at the company, then send a short note that makes it easy to say no. "Just checking in" sent five times is the answer to worry about.
How do you ask a happy customer for a referral?
Why ask it
Plenty of reps say they do this; fewer can produce the sentence. Have them say it as they would to the customer, including who they ask to be introduced to. A request for a named person gets introductions, and "let me know if you think of anyone" gets nothing.
Deals
How do you build rapport with a prospect you've never spoken to before?
Why ask it
The weak version is small talk: the weather, or a sports team spotted on a profile. Buyers who are short of time often warm faster to a rep who has done some homework and gets to something useful. Ask how they adjust for a buyer who plainly does not want to chat.
What do you ask in the first ten minutes of a discovery call?
Why ask it
Get the actual questions, in the order they ask them. A list that never leaves the buyer's current setup, such as which tool they use and how many people use it, collects facts and no reason to buy. Somewhere in there should be a question about what the problem costs or what happens if it is left alone.
How do you work out who actually signs, and what do you do when you can't get to them?
Why ask it
Reps who have sold into larger companies learn to ask early and plainly: besides you, who has to say yes? Listen for how they keep track of the other people involved, and for a plan when their contact wants to carry the message upstairs alone. "My contact has it handled" deserves a follow-up, because deals often go quiet that way.
A competitor is already in the deal. How do you sell against them?
Why ask it
The answer to hope for starts with asking the buyer what they like about the other option. Running a rival down usually costs trust with someone who is still considering them. Check too that they know their real competitors by name, including the buyer's option of doing nothing.
When a prospect says the price is too high, what do you actually say next?
Why ask it
Anyone can say they sell on value, so hold out for the next sentence they would really say. Reasonable ones include asking what the buyer is comparing it with, offering less scope for less money, or holding the number and going quiet. Note whether a discount is their first move or their last.
What's the last objection that genuinely stumped you?
Why ask it
A candidate who says nothing stumps them has either not sold much or is performing for you. A real answer is usually recent and tied to their product, and it ends with what they say now when it comes up. If your own reps hear the same objection, you have also had a preview of how this person would handle it.
How do you ask for the business? Give me the words.
Why ask it
Some capable, likeable reps never actually ask, and their deals drift. You are listening for a plain sentence with a date in it, said without apology. Rehearsed trick closes that corner the buyer are their own warning, especially if your customers are meant to come back and buy again.
Tell me about a negotiation where you gave something up. What did you get in return?
Why ask it
Discounting is the easiest way to close and the most expensive, so the trade is what counts: a longer term, earlier payment, a case study, a bigger order. A candidate who dropped the price to make the quarter and got nothing back will do the same with your margin.
A deal has been "closing next month" for three months. What do you do with it?
Why ask it
The choices are to find out what changed, go around the contact to someone senior, or take it out of the forecast, and a good rep will ask you a few questions before choosing. Leaving it where it is and hoping is the common answer in practice. See whether they admit to having done that.
Tell me about a deal you walked away from on purpose.
Why ask it
A rep who has never disqualified anything is probably carrying dead deals and spending hours on them. The story should include what they saw and what they said to the prospect, since telling a buyer they are not a fit is harder than it sounds.
Tell me about a time you needed engineering, legal or finance to get a deal over the line.
Why ask it
Bigger deals need favours from people who do not report to sales and are not paid on the deal. Ask how they made the request and how much notice they gave. A story about going over someone's head on the last day of the quarter tells you how your own legal and finance teams would get on with this hire.
What do you do for a customer after the contract is signed?
Why ask it
In a business that lives on renewals or repeat orders, the handover is part of the sale. Ask who they introduce the customer to and when they next make contact. If their last company took commission back on early cancellations, ask how often that happened to them.
Which would bother you more: missing your quota, or closing a customer who turns out to be unhappy?
Why ask it
It is a forced choice with no safe answer. Give credit for picking one and defending it, and for noticing that where the business depends on renewals, the unhappy customer costs the number as well. Then ask for a time they faced that choice for real and what they did.
Role-play
Sell me this pen.
Why ask it
The old standard still earns its place because it shows instinct in thirty seconds. A candidate who lists the pen's features has missed it, and one who first asks when you last used a pen, and what for, is doing discovery before pitching. Grade the first question, not the close.
Pitch me the product you sell today, in two minutes, as if I were your typical buyer.
Why ask it
They have given this pitch many times, so it is the fairest test of how they sound at their best. Time it. Note whether it opens with the buyer's problem or the company's history, and whether you could repeat the main point to a colleague afterwards.
Let's try a cold call. I'm an operations manager who has never heard of you, and I have a meeting in one minute. Go.
Why ask it
Tell candidates in the invitation that a role-play is coming, since you are testing skill and not their tolerance for an ambush. In the call itself, see whether they earn the next thirty seconds with a reason for calling you in particular, and whether they ask for a meeting before the minute is up.
I'm a prospect and I say, "Just send me some information." What do you say?
Why ask it
It is the politest brush-off in sales, and agreeing and sending a brochure ends the conversation. Better replies agree, then ask one question that makes the information worth sending, such as which problem the prospect would want it to cover.
Teach me something you know well and I probably don't, in three minutes.
Why ask it
Any subject works, from sourdough to the offside rule. Selling a complicated product is mostly explaining, and here you see whether they check what you already know, pick one idea over ten, and notice when you are lost. It also suits career changers with no sales history to draw on.
Will you send me the follow-up email you'd write after this meeting, as though I were a prospect?
Why ask it
Give them a day. The email shows how they write, which carries much of a sale now, and whether they listened: a good one repeats back what you said you needed and proposes a next step with a date. How fast it arrives is information too.
Habits and fit
What has to be true before you'll put a deal in the forecast?
Why ask it
You want a bar with evidence in it: a confirmed budget, a problem the buyer has put in writing, an agreed next step with a date. A candidate who forecasts on gut feel, or on how the last call went, will make your own number harder to predict.
How accurate was your forecast last quarter, and where were you wrong?
Why ask it
Few reps keep score on their own forecasts, so a candidate who can say what they called and what landed stands out. Ask which way they tend to miss: deals that slipped a quarter, or deals that never closed at all. The first is a problem with next steps and the second with qualifying, and they need different coaching.
What does your CRM look like on a Friday afternoon?
Why ask it
It sounds like small talk, and it is a question about record keeping. Reps who update as they go describe it casually, and those who batch everything on the last day of the quarter will usually admit it if you ask lightly. Thin records make a rep hard to coach and their accounts hard to hand over.
In a normal week, how many hours were you actually in front of buyers?
Why ask it
The honest number is often lower than expected, and candidates who have measured it stand out immediately. It also opens up what filled the rest of the week: internal meetings, admin, proposal writing, chasing implementation problems.
Which sales tools do you rely on, AI included, and what do you still insist on doing yourself?
Why ask it
Most reps can list their tools, so the second half carries the weight. Sensible lines include reading every message before it goes out in their name and doing account research they can vouch for. Ask how their answer squares with your own company's rules on customer data.
How do you keep up with what is going on in your customers' industry?
Why ask it
Ask for the last thing they picked up and then used in a conversation with a buyer. A trade newsletter, a customer's own announcements and a contact they phone for news are all fair sources. If they name a podcast, ask what it changed about a call they made.
What are you doing at the moment to get better at selling?
Why ask it
Ask for the specific thing: listening back to their own recorded calls, shadowing a stronger rep, practising one objection with a colleague. A reading list with nothing they changed as a result does not count. The hire you are after treats selling as a skill that can still improve.
What did your last manager push you on most?
Why ask it
Almost everyone has a standing note from their manager, and the ones who cannot name theirs either were not managed or were not listening. The specific weakness matters less than whether they can state it without defending it.
What coaching have you been given that you disagreed with, and what did you do about it?
Why ask it
Coachability is not compliance. The answer you want involves trying it anyway and reporting back, or making a case with evidence. Answers where they simply ignored the manager, or where they agreed with everything, are both worth probing.
When did you last help another rep close a deal that paid you nothing?
Why ask it
Sales floors run on favours: a shared contact, a practice run before a big call, covering a demo while someone is on holiday. A rep with a ready example adds to the team's number as well as their own. A blank from someone with years on teams tells you how they will treat your newest hire.
If you could design your own pay plan, how would you split it between base salary and commission?
Why ask it
The split they choose shows how much risk they are willing to carry and how sure they are of closing. Describe your real plan straight afterwards, because someone who wants a high base is unlikely to stay content on a commission-heavy one. Ask what they want and not what they earned: some places restrict questions about past pay, so check the rule where you hire.
Where do you want this job to lead: bigger accounts, managing a team, or something else?
Why ask it
Wanting to manage within two years and wanting to stay a seller for the next ten are both fine answers, for different openings. Be straight about which paths exist at your company. A rep hired on the hint of a team lead role that never appears has a reason to leave just as they become productive.
What would your first 90 days here look like?
Why ask it
A candidate cannot know your systems, so judge the order of things and not the detail: learning the product and the customers first, building a target list, then a pipeline figure they would hold themselves to by day 90. Compare that figure with your real ramp time and say so if it is far off.
What do you need from a manager and from this company to hit your number here?
Why ask it
Their list is a set of expectations you can meet or decline now: leads, someone booking meetings for them, an existing account list, room to move on price. A gap is cheaper to find in the interview than in the first quarter. Anyone who says they need nothing has probably not pictured the job in detail.
What would you like to ask me about the job, the team or the number?
Why ask it
For a seller this is discovery, and you are the buyer. Serious candidates ask how many reps hit quota, how territories are divided and why the last person left, and they follow up on your answers. Having no questions about a job that pays on results would be a strange way to choose one.
How to use these questions
Practical guidance for the conversation itself
Running the interview
Pick six to eight and go three layers deep on each
Anyone who sells for a living is practised at short, confident answers, so the best interview questions to ask salespeople are often the follow-ups: what exactly did you say, who else was in the room, what happened the following week. A long list asked once each produces a smooth conversation and no evidence.
Split the types of questions across the rounds
Openers suit a phone screen. Track record and Prospecting fill a first interview, Deals belongs with whoever will manage the hire, and one Role-play works best as its own short session. Keep Habits and fit for the last conversation, when pay, the path ahead and what they need from you are live questions. Agree beforehand who asks what, or three interviewers will each ask about quota and nobody will ask how the candidate closes.
Get numbers on the table in the first ten minutes
Quota, attainment, deal count, average size and ranking. Write them down as they are said, because they sometimes shift later in the process. If the figures from the interview and the reference call do not match, put the difference to the candidate before you draw a conclusion.
Ask for words, not frameworks
Whenever a candidate describes an approach, ask what they actually said to the buyer. Reps who have really done it will slip into first person and quote themselves. Reps who have read about it stay in the abstract however many times you ask.
Include a short live exercise
Ten minutes of discovery with you playing a buyer often tells you more than an hour of history, and the Role-play group has six ways to set one up. Give them the company context in advance so you are testing questioning and listening, not their ability to guess your business.
Ask every interviewee the same core set
Choose the questions for the role before the first interview and put them to everyone, then write up each answer the same day. Otherwise the most charming candidate wins, and charm is the one thing every sales applicant has rehearsed. Keep to the job as well: rules on personal questions, such as age, health or family plans, vary by country and state, so check what applies where you hire.
Verifying what you were told
- Ask for the quota number and the attainment separately, then check the arithmetic against the deal count and average size.
- If a candidate carried a team quota, establish which part was theirs personally.
- Ask who their manager was at the time, and confirm that name appears when you take references.
- Ask what percentage of their number came from renewals or expansions versus brand-new customers.
- Ask when their last quota was raised and whether they hit it after the change.
- For any deal story, ask the customer's industry, the deal length and who signed, since invented deals get thin fast under detail.
- Many employers confirm only dates and a job title, so ask what the candidate can show you directly, such as a team ranking or an award, without handing over anything their old employer would treat as confidential.
- Some places restrict asking what a candidate was paid. Quota and attainment are performance figures, but check the rule where you hire before asking for pay slips or commission statements.
What to listen for
Encouraging
Precise numbers offered without prompting, credit shared with an SDR or a solutions engineer, a lost deal explained as their own misread, and questions back to you about your sales cycle, pricing latitude and where leads come from.
Worth probing further
Percentages with no quota attached, every loss blamed on product or price, no examples of disqualifying anything, a manager they cannot say anything specific about, and a forecast process based on how calls felt.
Hard to fix later
Talking over you, treating your questions as objections to be handled, and answering a request for detail with a story about a different deal. How a candidate treats you in the interview is a fair guess at how they treat buyers on calls.
Adjusting for the sales position you are filling
SDR or inside sales
Weight the questions on outbound sourcing, weekly activity and coachability. Track record on closing matters less than volume of buyer conversations and how they handle being ignored for weeks at a time.
Enterprise or complex sales
Spend most of the interview on who signs, stakeholder mapping, forecast discipline and the internal-collaboration question. Long cycles punish reps who cannot navigate procurement and legal, however good they are on a first call.
First sales hire at a small company
The pipeline-source question matters most here, along with what they need from you. Someone who has only ever worked inbound leads at a large company may struggle in a role where nobody has heard of the product yet.
Account management or renewals
Lean on the difficult-customer story, the referral ask, the negotiation trade, what happens after the contract is signed, and the choice between quota and an unhappy customer. New-business hunting matters less here than whether existing customers stayed, grew and would take the candidate's call.
A career changer or a first sales job
There is no quota history to examine, so use the Openers, the teach-me exercise, the pen and the follow-up email. Ask for an occasion in any setting when they persuaded someone who started at no, and weigh how they take a correction during the role-play more heavily than polish.