Sales Interview Questions that Doesn’t Make You Sound Cliche

Charley Mendoza

September 4, 2023

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min read

Sell me this pen.

Ugh, cliché.

Every decent sales rep out there can answer that question.

Do you get the feeling that the candidates know what you’re about to ask because every other company asks the same thing??

So if you’re tired of the usual questions and the almost-scripted replies you get, here are non-cliché and definitely non generic questions so you can get to know your applicants better.

Sales Interview Questions to Spot the Posers

These are candidates who look good but can’t deliver. Remember, there are people who know how to sell, and those who can only sell themselves.

Ask hard questions that require on-the-spot thinking and introspection to weed out fakers, such as:

1. How did your former employer position itself in the market in comparison to your competitors?

Why this question: It’s easy to rattle off details about a company’s unique selling proposition (USP) and ideal client profile (ICP), but it’s harder if they have to compare it with competitors.

If they did the job well, they’ll know how to answer this question because it's common for prospects to say, "I already have “XYZ product.”

You’ll recognize real salespeople right away if they can differentiate in specific terms what makes them different or better than their competitors. Better yet, can they give specifics of how they compare in terms of certain features or benefits?

2. What’s the hardest part of the job for you? What did you do to overcome this challenge?

Why this question: Many posers will have no clear game plan to improve their career because they get by with sheer volume. Ask for specifics too, like why they think it’s the hardest part of the job and specific tricks they used to get better.

Extra Question: Would you rather close a $15,000 guaranteed deal or have a chance at a $200,000 deal?

These are made-up numbers, so adjust it to your current offerings. And it isn’t so much about weeding fakers but on finding the right fit.

Their answer will clue you in on their appetite for risk and their thought process. Some companies would prefer candidates to go for the safer deal, especially if the company is just starting out. Or maybe you’d prefer they go for the bigger whale. There’s no right or wrong answer because it depends on your business model and priorities.

What you’re looking at is their thought process.

A strong candidate will explain the pros and cons of both deals, or at least give a clear explanation of why they’re choosing one deal over another such as if they’ve already hit their quota or not.

A good candidate will also say they’d like a good mix of small and big size deals to have a healthy pipeline, while building relationships with big wigs capable of making huge deals.

General Yet Un Cliché Interview Questions for Sales

Now we’re done weeding the posers, let’s get to the usual questions but let’s frame them in a different light.

1. What do you know about our company?

Experienced and good salespeople will proactively research a company before talking to them. They should be able to tell you about your products and other offers, and other things they can find on your website like upcoming products or events.

2. Tell me about a time you didn’t meet your sales goal

Alternative Question: Describe a time you lost a deal. What did you do afterwards?

Ask this question to get a sense of their sales experience, specifically how they recover from rejection. Good salespeople know that a lost deal isn’t a total loss, there’s still opportunity to build a relationship for future sales or at least a chance to improve your demo for the next prospect.

Good answers may also include a show of active listening, and using context cues to offer alternative products or solutions without being too salesy.

3. How do you organize your day?

We’re not talking about breakfast rituals here. You’re looking for the process a candidate follows to keep their day organized and productive.

Poor answers like answering emails a few minutes after they arrive, or a lack of a way to prioritize whether to make calls or presentations show a disorganized candidate. These people will easily get overwhelmed during busy months.

4. What sales tools do you have experience using?

Ask this question to learn the type of tools each candidate is familiar with, and to get a sense of how much training they’ll need.

Great candidates don’t have to know each tool you use, experience with similar programs or features are enough. Weak answers that show lack of initiative to learn or interest in your software programs are red flags.

Answers with no attempt to show similarities with the CRMs they use in comparison to yours not just show lack of tech skills but selling skills too. They’re not doing a good job relating to you or selling themselves.

5. What can you teach me in 3 minutes?

This question tests an applicant’s communication and listening skills, as well as their showmanship – an important skill for sales professionals. It also tests their abilities to think on the fly and communicate in a concise way, just like when talking to prospects.

The exact topic they’ll teach you doesn’t matter. It could be about cooking, taking care of pets, or whatever hobby they enjoy. You’re just looking for clarity and passion.

If they can make you curious or excited about the topic after their explanation, that’s a good sign. That’s why this question is a good alternative to the cliché “sell me this pen” question.

Ask Good Questions, Avoid a Bad Hire

The average cost per hire is around $4,700 according to Society for Human Resource Management, meanwhile Harvard Business school says it takes upwards of six months to break even on a new hire.

Personally, I think the cost of a bad hire is:

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