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Outside sales representative interview questions, with a scoring guide

Travels a sales territory to find new customers, quote profitable deals and grow accounts. Here are 19 questions for an outside sales representative interview. Each comes with a follow-up and a 1 to 5 scoring guide so you can compare candidates fairly.

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On this page
  1. Questions specific to the role
  2. Behavioural questions by skill
  3. Prescreen questions
  4. Record checks after a conditional offer
  5. How to score the answers
  6. Questions to avoid

Questions specific to the outside sales representative role

Role-specific
Walk me through how you plan a week in your territory: who you visit, in what order, and why.
1 WeakDrives around and drops in wherever.
3 SolidBooks a few meetings ahead.
5 StrongPlans routes by area, mixes prospects with existing accounts, books ahead, leaves time for cold visits, and logs it all in the CRM.
Role-specific
Tell me about a deal you won from a cold visit or cold call. How did it go from first contact to signed?
Follow-up: How long did it take, and what nearly lost it?
1 WeakCan't give an example.
3 SolidWon it, but the steps are vague.
5 StrongClear steps: qualified the buyer, found the real need, followed up on a schedule, handled objections, and closed.
Role-specific
A customer will sign today if you go below your margin guideline. What do you do?
1 WeakAgrees to close the deal.
3 SolidSays no and loses the deal.
5 StrongLooks at what else can move (volume, terms, scope), gets manager approval if it makes sense, and never promises what they can't deliver.
Role-specific
Walk me through how you put together a quote after a site visit.
1 WeakGuesses from memory.
3 SolidUses the price list.
5 StrongMeasures and notes details on site, confirms specs, prices materials, labour and delivery, checks the margin, and follows up by a set date.

Behavioural questions by skill

Behavioural questions ask about something the person actually did. Past behaviour is a better guide than "what would you do" answers alone.

Sales and persuasion

Finds what the customer needs and closes.

Tell me about a sale you're proud of.
Follow-up: What made it work?
1 WeakNo example.
3 SolidTook an order.
5 StrongFound the customer's need and matched it.
Describe a time a customer said no. What did you do next?
Follow-up: Did they come back?
1 WeakGave up or pushed too hard.
3 SolidAccepted it.
5 StrongAsked why, handled the concern, and left the door open.
How do you keep track of leads and follow-ups?
Follow-up: Walk me through last week.
1 WeakThey don't.
3 SolidInformally.
5 StrongA consistent system with real follow-up.

Initiative

Sees what needs doing and does it.

Tell me about something you did at work that wasn't part of your job but needed doing.
Follow-up: How did you notice it?
1 WeakNothing comes to mind.
3 SolidHelped when it was obvious.
5 StrongSpotted the need and handled it without being asked.
Describe a time you had downtime at work. What did you do with it?
Follow-up: Was that normal where you worked?
1 WeakWaited to be told.
3 SolidAsked what to do.
5 StrongFound useful work such as prepping, cleaning or learning.
Tell me about a skill you taught yourself because it would help at work.
Follow-up: How did it help?
1 WeakNone.
3 SolidLearned only when required.
5 StrongLearned it on their own and can say how it helped.

Organizing and time management

Plans the work and meets deadlines.

Walk me through how you plan a typical work day.
Follow-up: What do you do when the plan falls apart?
1 WeakNo plan.
3 SolidA loose plan.
5 StrongA clear system, such as a list or calendar, and how they adjust it.
Tell me about a time you had several deadlines at once.
Follow-up: How did you decide the order?
1 WeakMissed some without warning.
3 SolidMet them by working late.
5 StrongPrioritized, planned, and met them or flagged early.
Describe a system you use to keep track of tasks, orders or paperwork.
Follow-up: Show me how you'd use it on your first day here.
1 WeakNone.
3 SolidMostly memory.
5 StrongA reliable system with an example.

Customer service

Keeps customers looked after, even when it's hard.

Tell me about a time a customer was upset with you or your business. What did you do?
Follow-up: How did the conversation end?
1 WeakArgued, passed them off, or avoided the customer.
3 SolidStayed polite and followed the rules, but the customer left unhappy.
5 StrongListened, owned what they could, fixed it or offered a real option, and stayed calm.
Describe a time you went beyond what was expected for a customer.
Follow-up: How did you know the extra effort was worth it?
1 WeakNo example, or the 'extra' was the basic job.
3 SolidA good example with little thought for the business side.
5 StrongWent the extra step in a way that also made sense for the business.
Tell me about a time a customer asked for something you couldn't give them. How did you handle it?
Follow-up: What did they do next?
1 WeakJust said no.
3 SolidSaid no politely and explained why.
5 StrongExplained, offered an alternative, and made sure they had a way forward.

Communication

Explains clearly and keeps people in the loop.

Tell me about a time you had to explain something complicated to someone who was new to it.
Follow-up: How did you know they understood?
1 WeakCan't explain clearly, even in the interview.
3 SolidExplained it but didn't check understanding.
5 StrongUsed plain words or examples and checked they got it.
Describe a time you had to give bad news to a customer, coworker or manager.
Follow-up: What did you say first?
1 WeakAvoided it or left it to someone else.
3 SolidDelivered it, but bluntly or late.
5 StrongDelivered it early and clearly, with a next step.
Tell me about a time a misunderstanding caused a problem at work. What did you learn?
Follow-up: What do you do differently now?
1 WeakBlames the other person entirely.
3 SolidFixed the issue with little reflection.
5 StrongFixed it and changed how they communicate, such as confirming in writing.

Prescreen questions for outside sales representative candidates

Ask these on a five-minute phone call or send them as a form before you book interviews.

  1. Are you legally entitled to work in Canada? (Yes / No)
  2. Which days and times are you available to work?
  3. When could you start?
  4. What pay are you looking for?
  5. What interests you about this job?
  6. This role is mostly on the road. Do you have a valid driver's licence and a reliable, insured vehicle you can use for work travel? (Yes / No)
  7. How much business-to-business outside sales experience do you have? (None / Less than 2 years / 2 to 4 years / More than 4 years)

After a conditional offer: record checks

Record checks (criminal record, vulnerable sector, driver's abstract) are not prescreen questions. Ask for them only after you make a conditional offer, and only when the check is tied to the real duties of the job, such as driving, handling cash or working with children or vulnerable adults. Asking earlier can screen people out for reasons the job doesn't need. In British Columbia and Quebec, human rights law protects people from discrimination for a conviction that isn't related to the job. Say in the offer letter that the offer depends on the check, and tell the candidate which results would matter for this job.

  • Driver's abstract. This offer is conditional on a driver's abstract. Are you willing to provide it?

Use our conditional offer letter template. Manitoba and Newfoundland and Labrador guidance says to wait until a conditional offer, and the Ontario Human Rights Commission says a driver's licence number or copy may be requested only after one. See questions to avoid.

How to score the answers

  1. Ask every candidate the same questions in the same order. That's what makes scores comparable.
  2. Write down what they did, not your impression. "Closed alone on a Saturday and restocked for the morning" beats "seems reliable".
  3. Score each answer from 1 to 5 against the guide under the question. A 3 is a solid, acceptable answer.
  4. Average the scores and read the notes behind any big gap between interviewers.
  5. Check references on the areas where you're least sure.

Questions to avoid

Hiring questions should be about the job. Human rights law in every province and territory protects people from being treated differently because of things like age, family status, disability, religion, race, place of origin, sex, sexual orientation, and gender identity. The list of protected grounds differs a little by province, so check yours.

Stay away from questions like these:

  • "How old are you?" or "When did you finish high school?"
  • "Do you have kids?" or "Are you planning a family?" The Ontario Human Rights Commission says an employer cannot ask whether an applicant is pregnant or plans to have a family.
  • "Where are you from originally?" You can ask: "Are you legally entitled to work in Canada?"
  • "Do you have any health problems?" You can ask: "This job involves [a real duty]. Can you do that, with or without accommodation?"
  • "What do you make now?" Nova Scotia and Prince Edward Island do not allow employers to ask about pay history. Asking what pay the person expects is fine.
  • Questions about the hours a person can work that mention family or religious commitments. Ask only whether they can work the hours the job needs, and state those hours.

Criminal record and driving record: wait until you have made a conditional offer, and ask only for what the job needs. Manitoba and Newfoundland and Labrador guidance says to wait until a conditional offer. Quebec's rights commission says a conviction counts only if it is connected to the job. Ontario's commission says you may ask only about convictions that have not been pardoned, and that a driver's licence number or copy may be requested only after a conditional offer and only if relevant.

This is general information, not legal advice. Rules differ by province. Human rights bodies: see the official sources.

Rules that differ by province. Ontario (25 or more employees), British Columbia and Prince Edward Island require the pay or a range in public job postings. Nova Scotia and Prince Edward Island do not allow pay-history questions. Ontario employers with 25 or more employees must tell each interviewed applicant within 45 days whether a hiring decision was made. Unpaid trial shifts that involve real work are not allowed in Ontario, British Columbia or Alberta. See hiring rules by province, checked 7 October 2026.

Questions

What should I ask in an outside sales representative interview?

Ask about the parts of the job that matter most: sales and persuasion, initiative, organizing and time management, customer service, plus role-specific questions such as "Walk me through how you plan a week in your territory: who you visit, in what order, and why." Ask every candidate the same questions so you can compare them fairly.

How do I score an outside sales representative interview?

Score each answer from 1 to 5 against a short guide that describes a weak, solid and strong answer. Score what the person actually did in their example, not how confident they sounded. Then average the scores and read the notes behind any big differences.

What should I ask before interviewing an outside sales representative?

Use a short prescreen: work eligibility, availability, start date, pay expectations and the must-haves for the role, such as "This role is mostly on the road. Do you have a valid driver's licence and a reliable, insured vehicle you can use for work travel?" Ask what pay the person expects, not what they earn now: Nova Scotia and Prince Edward Island do not allow pay-history questions.

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