Sales Managers: These 91 Interview Questions Help You Hire Great Salespeople

Sales Managers: These 91 Interview Questions Help You Hire Great Salespeople

Sales Hiring
Chris Orlob
June 28, 2022

Are you looking to DOUBLE your success at hiring A-Player sellers?

I hope so.

Great sales hiring is the biggest factor in sales leader success.

So if you ARE, this might be the most important thing you read all year.

You’ll see why in a minute.

But First… A Disclaimer:

These questions are NOT for the faint of heart.

Many of them take guts to ask.

If you can’t do that, well… don’t waste your time reading any further.

You’ll waste your time. This is a long post!

But if you CAN ask tough questions…

These Will Take your Interviews to the Next Level

Asking the right interview questions can double your odds of hiring great sellers.

But most sales manager don’t have a method of asking interview questions.

They just… wing it.

Today, you're going to learn how to predict sales candidate success.

All through asking great sales interview questions.

And Here's the First Thing To Learn...

Great sales interview questions spring from your ideal sales candidate profile.

They are a byproduct.

There are three “sections” to any ideal sales candidate profile.

  1. Traits
  2. Experience
  3. Skills

Each section should have a handful of criteria.

Select your questions to screen for THOSE criteria.

In other words… don't just read this post and start firing away!

You only need to ask the questions that help you identify the specific traits, experience, and skills YOU’RE hiring for in a sales candidate.

Ready to see the questions?


Let’s get started.

But before we do… here are a few ground rules.

P.S. Download our (free) interview questions cheat sheet here.

First: A few “ground rules” for great sales interviews

Before you dive into the questions, follow these tips.

They’ll dramatically improve your interviews.

  • Focus your interviews on the candidate’s work history. Don’t just ask interview questions willy-nilly. Structure your interviews to ask repeated, consistent questions about each of the candidate’s work experiences chronologically. When you do this well, it automatically reveals PATTERNS. You'll know exactly who you’re hiring by the time you’re ready to make an offer. I’ll write more on how to structure chronological interviews later. They are powerful.Okay. Onward to the next.
  • Select no more than 4-6 “traits” to screen. Remember when I mentioned your ideal candidate profile has three sections: traits, experiences, and skills? Well, the “traits” section should have between four and six items. More than that, and you’ll have unfocused interviews that only scratch the surface.
  • Dig into only 1-2 traits during late-stage interviews. After you’ve had a few interviews with a candidate, you should have a sense of clarity on some of their traits and skills, and you’ll feel fuzzy on others. Use the next interview to GO DEEP on 1-2 must-have items you feel fuzzy about. Select your questions from the cheat sheet accordingly.
  • If a person cannot easily answer a question about a recent time they demonstrated a trait, they probably don’t have that trait. You’ll notice that most of the trait-based questions ask for evidence and examples of a recent time a candidate used that trait. If they struggle to think of something recent, chances are they don’t have it.
  • Probe, probe, probe. Almost every interview question in this post will only scratch the surface. These are meant to kickstart a discussion. It’s up to you to ask follow-up questions and DIG.


Let’s get into the sales interview questions.

Interview Questions to Assess TRAITS

Here’s why to start with traits…

Even though skills and experience are important, traits are the most fundamental aspect of sales success.

If you have bad traits but strong experience, you still have a bad candidate.

But if you have GREAT traits and light experience...

That person will find a way to win.

Traits are the “raw material” of sales success.

Here are the interview questions that help you predict successful traits.

Grit & Perseverance

  • What drives you, and how has that shown up in your work recently?
  • What kind of sacrifices did you have to make to be successful in [specific job]? (Repeat this question for each of their most recent jobs.)
  • Tell me about the top 2-3 stories of perseverance from your life and career.
  • Tell me about a time you dug in and turned around a losing deal?
  • Tell me about your day to day and week to week work habits in [specific job? (Repeat this question for each of their most recent jobs.)

Desire to Achieve

  • Tell me about the top two times you went above and beyond expectations in [specific job]? (Repeat this question for each of their most recent jobs.)
  • Tell me about your proudest achievements at [specific job]? (Repeat this question for each of their most recent jobs.)
  • Tell me about the hardest you worked to achieve a goal at [specific job]? (Repeat this question for each of their most recent jobs.)
  • What’s the toughest goal you’ve ever set for yourself and pursued at specific-job? (repeat for other jobs, and for their life in general)


  • Tell me about the last time you found yourself emotionally invested in winning some sort of competition.
  • Walk me through the series of hobbies and passions you’ve had as your life has progressed? (Look for competitive as a consistent pattern).
  • When you think about your sales leaderboard, what metric are you consistently at or near the top at? (Repeat this question for each of their most recent jobs.)
  • Who are you competing with right now, and how?


  • Tell me about some constructive feedback you received in [specific job]? What did you do next? How did it change your behavior? How do you currently behave in that area? (repeat for other jobs)


  • What drives you and why?
  • Tell me about your strengths and weaknesses as a seller in detail - let’s aim for 5–6 in each category if you can.
  • What are you NOT interested in doing professionally or as a seller?
  • What was the most common misconception about you at [specific job]? (Repeat this question for each of their most recent jobs.)
  • [At the end of an interview] What’s one question you wish I would have asked you, but didn’t? Why?

Emotional Quotient (EQ)

  • Walk me through the details of a situation at [specific job] where you had a disagreement with a colleague, boss, or customer. How did you handle it?
  • Can you think of a time you inspired or motivated a teammate or colleague? Tell me more about that.


  • Walk me through how you’ve acquired your sales skills and learned to sell?
  • Tell me about the most recent book, podcast, or course you’ve taken to develop yourself professionally?
  • Tell me about a recent time you developed a new skill. Walk me through how you approached it?

Team Player

  • Part of our hiring process is we’ll eventually want to talk to a couple of your previous teammates. What would most of them say about the good, and not-so-good aspects of working with you?
  • Tell me about a time you went above and beyond to help one of your teammates out in [specific job] (repeat for other jobs and roles)
  • Tell me about the most recent time you made your team better in some way? What did you do? Walk me through how you approached it? (repeat for other roles).

Preparer, Methodical, Strategic Thinker

  • Walk me through what you did to prepare for this interview? what information did you gather? What questions did you pre-plan on asking? What questions did you anticipate that I’d ask and how did you prepare?
  • Walk me through, in detail, a sticky deal situation you found yourself in, and how you navigated out of it? Walk me through everything from how you assessed the situation, to your action plan, and how you executed.
  • Walk me through your process for how you prepare for key sales calls.

Bias for Action

  • Walk me through the most recent time you had an idea about a deal or sales situation, and you immediately acted on implementing it.
  • Walk me through how you typically plan and execute your day.


  • Walk me through a time you found yourself in a bad situation, and how you got out of it? It could be a PIP, a deal gone-south, whatever. Walk me through the moment you decided you were going to turn it around. What did you do?
  • Tell me about a recent time you kept striving toward a goal even when most rational people would have assumed it was hopeless?

Interview Questions to Asseess EXPERIENCE

Unless you're hiring entry-level sellers, experience matters.

Don't let anyone tell you otherwise.

That's because what it takes to be successful in one sales situation differs dramatically from the next.


Your hire AEs that sell to DevOps functions in Fortune 1000 companies.

They run 90 day proof-of-concepts (POCs).

And they need to build consensus across a wide range of influencers (4-6) over the course of a 12 month sales cycle.

Now let's say you're interviewing a rep who hit 150% of her number for the last three years.

And her traits are GREAT! She's gritty. She's competitive. She's coachable.

But her sales experience consists of selling software to small family dental offices.

10-day sales cycle.

100+ outbound calls per day.

One decision-maker.

Do you hire her?

With an experience delta like that, probably not.

A rep that was successful in one sales situation may fail in another.

So understanding how closely someone’s previous sales experience matches YOUR sales situation is critical.

This is also your opportunity to ask interview questions about their track record.

Previous sales success is usually the best predictor of future sales success.

Questions to Understand Their Job Patterns

Aim to ask these questions about each of their most recent three sales experiences.

  • Tell me about your roles and responsibilities in [specific job]?
  • At [specific job], walk me through two deals from initial contact all the way to close, and every step, tactic, and strategy you took in between. Spare no detail. (repeat for each job)
  • What caused you to move on from your previous role?
  • What compelled you to take your talents to this role?
  • What did you like most and least about this job?
  • Tell me about the bosses you had while in this role? What would they say about your strengths? Your weaker points? How would they rate you performance-wise? What did you like and dislike about this boss?

Track Record of Success, Achievements, and Mistakes

Aim to ask these questions about each of their most recent three sales experiences.

  • What are the top few achievements you’re most proud of in life and career?
  • What were your biggest accomplishments at [specific job]? HOW did you go about, in detail, making that happen? (repeat for each role)
  • Tell me about the things you consider to be key mistakes you made while in this role?

Attainment Record

Attainment, by itself, is a useless number.

It tells you almost nothing about a candidate.

Some reps hit 150% of their number because they have a rich territory.

Others hit 96% of their number… and that’s considered an achievement at certain companies

One of the best reps I ever hired “only” hit between 96% and 102% in her previous job.

That was considered top decile!

Had I not asked the right follow up questions, I wouldn’t have hired her.

That’s why all of the followup interview questions listed here matter.

They give you the full story.

  • What was your quota during [x period]?
  • How was that quota structured? i.e. how much of that was pure net new business vs. upsell. vs. renewal ARR?
  • How did you do against that quota during that same period?
  • Walk me through in detail how you achieved that?
  • How many people were on your team during that time?
  • What was your stack rank on your team during that time?
  • What context, if any, would you want me to know about your attainment during this period

Repeat for each relevant fiscal period that you have time to dive into.

Interview Questions to Assess SKILLS

I have a confession to make.

The best way to assess skills during a hiring process is not interview questions.

It’s mock sales role plays and  live deal reviews.

However, you can still glean plenty of insight into a candidate’s skill through interview questions.

So, pepper a few of these in.

Business Acumen

  • Walk me through a business case you helped a customer put together to justify a purchase. What was the defined business problem to be solved? What were the business ramifications of not solving it? What was at stake financially? How did you come up with that math? What high-level projections did you include in the business case? What were the drivers of those projections?
  • If you were the CEO of your current company, what would keep you up at night when it comes to either your internal operations, or the external market environment?
  • If you were an investor in our company rather than a job candidate, what would you want to know about our business?

Outbound Prospecting

  • Tell me about your daily prospecting and outbound habits in x-role?
  • How many calls, emails, or contacts were you reaching out to daily?
  • Walk me through how you would prepare for, and execute an outbound call, email, or sequence? What would you do for call research? What were you looking for? How would you structure the call or email? What would you say? Do you have an example you can share?


  • What’s your framework and process for running a great discovery call? How do you structure it?
  • Tell me about a recent discovery call you knocked out of the park. Why was it so great? What questions did you ask? What was the business problem you eventually unearthed? How did you get there? How did you get the customer to open up?


  • Tell me about the last sales presentation or demo you knocked out of the park. Why was it successful? How did you structure it? What did you say?

Objection Handling

  • What’s your framework and process for overcoming objections? What steps do you take? What do you say?
  • What are the top 3 most common objections you get in [specific job], and how do you handle them?
  • Tell me about a time in this last week you got an objection and successfully overcame it? How did you handle it? What did you say?

Selling to Power and Multi-Threading

  • Who was the highest ranking person in your deals you typically worked with and sold to in [specific job]? Walk me through how you would gain access to that person? What was your approach?
  • Tell me about a time you earned credibility from a high-ranking executive? What did you do? How did you make that happen?
  • Tell me about the ideal “blend” of people you’d navigate to get deals done? Who would you develop into a champion? Why them? Who would you try to box-out or neutralize? Why them?
  • Walk me through a deal where you executed multi-threading the best you ever have.

Complex Buying Process Navigation

  • Walk me through, step by step, what steps your prospects and customers would have to take to make a purchase decision in [specific job]? Who was involved at each step, and how?
  • How did you drive the process through legal, security, or procurement hurdles?
  • Tell me about a time you and your champion had to go find or create budget that didn’t exist at the start of the deal.

Time Management

  • Walk me through how you manage your time and how you plan your days.

Territory and Account Planning

  • Walk me through, step by step, how you develop an account plan? What are the key sections you include? How do you come up with an action plan? Can you tell me about a recent example of an account plan you created?
  • Walk me through, step by step, how to develop a territory plan? What are the key sections you include? How do you come up with an action plan? Can you tell me about a recent example of an territory plan you created?

A few final interview questions

As you wrap up and get to the end of a hiring process, here are a few final sales interview questions worth asking.

  • One of the things we’ll do at the end of this hiring process is talk to a couple former bosses of yours. When I talk to [your former boss], what’s he going to tell me about both your strengths and weaknesses as a seller?
  • What do you think is going to be uniquely difficult about selling [your company’s product]?
  • Tell me about your early career and college days. What were some of the most influential experiences you had that shaped you and how? Who were some of the most influential people in your life and how did they shape you?
  • What are your goals for your next job? What are your long-term career plans and goals?

That last question should arguably be the FIRST question you ask in a sales interview.

Your job as a sales manager is to SELL candidates on working with you.

The answer to that last question gives you some of the ammo you’ll need to do that.

Here’s what to do next


That brings us to the end.

Do you want an easy to use “summary” of these questions?

One you can “skim” right before you jump into your next interview?

Download our (FREE) cheat sheet.

It summarizes these questions, by category.

Get it for free here.