Top 10 interview questions in sales hiring

There’s no such thing as a perfect interview question.

There’s no one question you can ask to figure out whether someone is the right candidate and will be amazing at sales.

Questions won’t give you all the answers. However, when you’re asking questions, you’re collecting data. And what you want to do is collect enough data so that you can make a judgement call: Will this person be worth investing in?

Giving people practical tests and throwing them into the fire and seeing how they react will normally give you more answers than your standard interview questions. But since practical tests aren’t always possible, here’s a set of 10 interview questions that’ll help you find your next sales hire.

Remember, a lot of people will have weak answers to some of these questions. This doesn’t mean they’ll be bad at the job.

1. Why sales?

This is the most fundamental question when hiring salespeople. Ask the candidate why they’ve chosen sales as a career. Why have they been doing it and why do they keep doing it? What is it about selling that appeals to them? What is it about selling that makes them want to be in this profession? How did they get into it? What’s the reason? What motivates them?

In sales, motivation is crucial to performance. What drives a person, what’s their purpose and what gets them going? What are they striving for? If you know these things you’ll be able to provide them with the support they need in their journey and help them get to that goal.

You can quickly explore if that goal aligns with the goals of your company and team. If it does, then chances are it’s a good fit.

2. Why do you want to sell this product?

This may seem like an obvious question, but a lot of companies neglect to ask their candidates, “Why do you want to sell this particular product?”

This is a good question to ask because you’ll find out if they’re thoughtful. Is there a purpose behind them sitting here or did they just apply to a bunch of jobs to see what would happen?

If they have a reason or a pre-existing relationship with your company or product, it increases the chances of the candidate being good at the job.

3. What do you know about our customers?

This is another fundamental question to ask during the early interview stages that a lot of sales managers miss.

You want to figure out if the person did their homework. How well do they understand your customer? They might have been misinformed as to who your customer is. If that’s the case, this is your opportunity to clarify that.

Next, it’s time to figure out if your customer is someone this candidate will care about. Why do they think they can communicate well with this person? Why do they think they can influence them? Can they relate to them?

4. What do you know about our competitors?

Do they know what the competitive landscape looks like? Do they know who you’re up against?

Have they done their research to see who else is in this space? Do they know what sets your company and product apart? Why do they think they could win selling against these people?

If they don’t know the answers it’s not the end of the world. Most candidates won’t know your competitors very well, it doesn’t necessarily make them a bad fit.

5. When was the last time you were really stressed out and how did you deal with it?

This is a powerful question because you want to know how people act under pressure. This is when you can uncover both the really good sides and really terrible sides to a person.

Potential sales hires most likely won’t be prepared for this question. This means their answer might be complete BS and just something that they’ll say to make them look good.

Whatever the reason, work-related or personal, how did this person deal with that situation? What was it that stressed them out? This is a simple question that can be really revealing.

Look at the situation they describe. Is it a situation you can relate to or does it seem really trivial?

By asking this, you’ll get an idea of how this person might react in stressful situations, when being put under pressure, or faced with challenges.

Lastly, how do they handle that stress in the workplace?

6.When was the last time you took a big risk and it didn’t pan out?

This is another question most sales hires are unlikely to be prepared for. It will reveal if they’re comfortable and secure in themselves, two crucial ingredients for a good salesperson.

You want to know that these people are risk takers. Because they should be. If they struggle to come up with a risk they’ve taken in the last 10 years, well—that’s not a good sign.

The risk itself doesn’t have to be related to selling, it can be anything in life. You just want to know that when this person sees an opportunity, they’ll go for it. Taking risks speaks to a killer instinct and a confidence that will translate really well in selling.

Don’t forget to ask how they responded when that situation didn’t pan out.

7. When was the last time you lost a deal?

“I’ve never lost a deal.”

If someone says this, it’s very likely not true. But it might also mean they’re not taking enough risks with their prospects.

You want to know how often the potential sales hire loses deals, but you also want to know the reasons as to why this deal didn’t work out. You want to hear them analyze themselves.

If they’re good at analyzing what happened and why the deal didn’t work out, it shows a certain level of maturity and indicates that they’ll have a good understanding of a prospect’s situation.

If they have that understanding, it also means they’ll know what needs to happen in order to close that deal.

They’ll know what they need to work on in order to improve at selling.

8. When was the last time you won a deal?

You don’t just want to know how they cope in more sticky situations. You also want to know about their successes. You want to see if they get excited, passionate and motivated when they talk about the deals they’ve closed. How do they talk about their wins? How much energy do they bring? How much motivation and inspiration do they gain from these wins?

And the same questions goes, do they know why they won this deal?

9. What was the last sales tactic that you learned?

When was the last time this person learned something, either from a book, a course, a blog post, someone else, a workshop—anything. How did they apply what they learned to their job?

It doesn’t matter if it worked or not. This question explores whether this person is a learner. Are they coachable and do they want to continuously grow and get better at what they do?

The best salespeople in the world are lifelong learners. They never stop trying to find new ways to get better at their jobs and close more deals.

10. How do you think this interview is going so far?

This is an opportunity for the person to be self-aware and self-reflective with you as a prospect.

The product they’re selling is themselves, and you’re the potential customer. Now is when you want to see what this person thinks it takes to close this deal and make you hire him or her.

How good are they at reading other people and can they make a good judgement based on the conversation you’re having?

This will translate to their sensibilities when they talk to prospects and how much they can influence the process. Do they understand what’s going on? Maybe they think they killed it at a question where you were underwhelmed. If the gap in your perceptions are too big, it’s likely that this is not a very good salesperson.

Two questions for the interviewer

These questions will help you uncover how likely it will be that this person will be amazing at selling your product to your potential customers.

Remember, no single question can point to if you should hire someone or not. But what you should ask yourself is:

  1. Do I like this person?
  2. Would I buy from this person?

If the answers to these two questions are “no,” do not continue the process because they will not be a good cultural fit for you and your team.

If the answer is “yes,” then move forward with them.

I’d love to hear what you ask or what you’ve been asked during interviews and what the answers were. Share your stories in the comments and help everyone learn more.

Recommended reading:

My startup hiring interview hack: Why? Why? Why?

A simple strategy to x-ray through the bullshit answers applicants give you and get real insights into what makes them tick.

Hiring for startups: How to recruit the un-recruitable!

How do you find high-performers? And how to make them want to join your team? Here's come unconventional startup recruiting and hiring advice ...

The 5 biggest risks when hiring salespeople for your startup!

The five biggest risks when hiring salespeople for your startup and what to do about them!

Table of Contents
Share this article