Sales Interview Questions: answering them and asking them

15 Apr 2024

I’ve been working in sales for virtually all of my adult life, working my way up through the ranks. I’m fairly sure that I’ve been asked and asked every single interview question about sales that there is. It’s high time I share that knowledge.

No matter which side of the interview you’re on, there are some questions you need to be ready to ask and others you’ll want to prepare answers for.

What do I mean by this?

Well, there are two kinds of interview questions, the kind asked by the interviewer and the kind asked by the interviewee. Both are equally important.

And it means everyone at the table needs to do some prep work.

I want to share with you the questions I like to ask as the interviewer and what kinds of answers I’m looking for. Then, I’ll give you a few of the questions I have been asked by interviewees (or that I have asked as an interviewee) that impressed me and why.

Hopefully, by the end of this article, you’ll feel a bit more confident going into that interview.

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Interview Questions from the Hiring Chair

When I’m conducting an interview (whether for sales or otherwise), I will have in my head an idea of the kinds of skills that I am looking for and any question I ask will reflect this.

In terms of a sales role, I want to know that they can build a rapport with a potential customer and understand what made that person go searching for a CRM system. I will also ask my potential salesperson questions to determine their work ethic and technical ability…it’s a software company afterall.

I’ll usually also ask questions to gauge if I think this individual will fit well into the company. For example, I’ll want to know if they can collaborate with other members of the sales team and with other departments.

So that’s my general goal when interviewing. But some of the questions I use to gather this information are:  

Question 1: How do you research prospects before a call or meeting? What information do you look for?

This interview question gives me an idea of both the individual’s work ethic and sales experience. Depending on their answer, I’ll know whether they are someone who dives deep into information beforehand or who relies on their conversational skills.

There isn’t a wrong answer, per se. It’s more a way to understand the person’s style of rapport building and customer engagement.

Tips for answering this question:

Be honest. If you say you gather lots and lots of information in order to appear really detail-focused but are more of a conversational person, you’ll get caught out within a month of your new job.

Question 2: How do you organise your day?

Once again, when I ask this question in an interview (especially in sales), I’m not actually asking for a minute-by-minute breakdown. The question is more geared to getting a feel for how structured a candidate’s approach to work is.

If I’m interviewing a salesperson, I expect to get a response describing a somewhat fluid day…checking emails and responding first thing, preparing for any calls I have during the day, making those calls, etc. If I were interviewing for someone in a more rigid job role, such as project management or technical support, I would expect a different answer.

Tips for answering this question:

Don’t brush it off and say that you “deal with stuff as it comes up.” This makes it sound like you have no time management skills. Plus, I don’t think it’s true for most people. Most of us will check our emails first thing and then check our diary to plan out the day. Think about what you actually do and, if you aren’t happy with your answer, consider what you can do to improve your time management.

Question 3: Tell me about a time you lost a sale (or didn’t achieve a goal)?

Oh, salespeople hate this interview question (well, everyone does, really), but it’s important for a number of reasons.

Basically, I’m trying to find out who this person is going to blame when stuff doesn’t go right. I’m really asking if can they take responsibility for their actions. And are they honest enough to admit this in an interview.

If someone tells me about a time their prospect elected to go with a competitor because it was a better fit, that tells me they don’t want to tell me about that other time they didn’t follow up with a prospect.

On the other hand, if someone tells me about a time they didn’t follow up with a prospect and lost the sale because of it, that tells me that they are able to reflect on their behaviour. It also tells me that they can admit to getting something wrong and (here’s the important bit) learn from their mistakes.

Tips for answering this question:

Prepare for it, you’re going to be asked.

And don’t just prepare the story of the incident. Tell me what you would have done differently to show me learned from experience. If appropriate, you may even want to give an example of how you then put that new knowledge into practice a few months down the line.

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Questions to ask in an interview…whether sales or otherwise

You should have questions about the company you’re applying to work for and the job role you want to have. If you don’t have questions, as the interviewer, I will have to assume that you aren’t that interested. Harsh, but that’s the impression it can give.

Of course, you’ll have questions about targets, travel requirements, holidays, bonuses, sales commissions, etc. And that’s all important. But trust me, there’s other stuff you want to know.

I’ve put together three questions that really impressed me. You don’t have to use these exact questions, but I would urge you (in the strongest possible language) to think about what you want to know about your prospective job, team, boss, and company.

Question 1: What does success look like for this role after a month? After six months?

Great question. This tells me (1) that you want to succeed and (2) that you know it will take time to take on the full responsibilities of this new role.

As the interviewer, this question should give me a chance to tell you about the induction process and a bit about how you will grow into your new role. It also gives me a chance to tell you a bit about the business structure.

For example, if you were applying to be a salesperson here at OpenCRM, I could tell you how we educate you on the system first before unleashing you on new prospective customers. I would also probably tell you that, due to the depth and breadth of the system, I wouldn’t expect you to be fully trained up on it for at least 3 months. Because it’s me, I’ll probably also tell you about how I learn something new about Open CRM every single week.

Tips for asking this question

Remember that this should be a dialogue. Ask follow-up questions and ask for clarification if you need it. Will there be performance reviews? How will your new manager help you achieve this success? And so on.

Question 2: What will my relationship be with other departments and members of my team?

Especially in a sales interview, this question is great because it gives me a chance to tell you how the company as a whole functions. Depending on how it is asked, it also tells me everything I need to know about this individual’s willingness to collaborate and share responsibility.

For the interviewee, my answer helps flesh out what their day to day will look like. It can also give you a window into the company culture.

Tips for asking this question

Consider what you want to hear from an answer. Do you want to collaborate on long-term projects? Would you rather “keep your head down” and focus just on sales (for example)?

Once you know what you want in your day to day job, you’ll be able to chat about your interviewer’s response to this question.


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Question 3: What do you think makes this company or department unique? What makes it a good place to work?

Don’t ever forget that, as much as you are being interviewed, you are also conducting your own interview. You are finding out if this is a department and/or company you want to be a part of.

I have been in interviews that went very well, where I was offered the job, but that I turned down because I essentially didn’t like the company once I got in the room. These were companies where salespeople were siloed from the rest of the business and pitted against each other. I don’t mean healthy competition, I mean something a bit mean.

They weren’t companies that I wanted to work with at the end of the day.

So when someone asks me this question, it tells me that they are not just in this interview looking for their next paycheque. They want to find a job they like for a company that they WANT to be a part of.  

Tips for asking this question

Listen very closely to what you are told and what the body language of the person who is answering is telling you.

Remember, you’re going to be living this life every single day. Make sure it fits with who you are and what you want.