Interviewing sales candidates can be particularly challenging. Often, sales candidates can be hard to read in an interview since many are skilled at presenting themselves in a favorable light.

A powerful technique for quickly moving past a candidate’s defenses is to use “extreme” questions. When asking the right type of extreme questions in a sales interview, you are much more likely to identify a candidate’s true potential.

This technique’s power comes from its ability to get right at the heart of the matter, allowing you to learn the candidate’s tendencies. “Extreme” interview questions gain their namesake for a reason and form an essential part of a sales interview.

In this guide, we will explore precisely how to create your very own extreme questions in a sales interview and provide examples you can use for inspiration.

What are Extreme Interview Questions for Sales?

Extreme interview questions include superlative words like most, least, biggest, smallest, worst, and best. These do not allow for neutral answers, and often encourage candidates to think outside the box to find their best response.

Extreme questions are particularly effective when a sales candidate describes a negative reaction to a past situation.

For example, say the candidate says the following: “I guess I have always found cold calling challenging.” Here are two ways the interviewer can respond, one with a standard question and one with an extreme question:

Standard Question Example:

Question: “What did you find challenging about cold calling?”

Candidate: “Making the time during my busy schedule . . . that was always tough.”

Extreme Question Example:

Question: “What was the most challenging aspect of cold calling?”

Candidate: “Probably the anxiety involved in the whole process.”

To get maximum leverage from an extreme question, follow up with the echo technique:

Question: “Anxiety?”

Candidate: “After a prospect would hang up on me, my hurt feelings would get me worried about the next call.”

Now, you can continue to probe to find out how pervasive this issue is for the candidate, and gauge whether it could get in the way if they came to work for you. The echo technique is an excellent way of asking for more information without making the candidate feel defensive. You will gain insight into their ability to handle a pressured sales position.

Examples of Extreme Questions to Use in Sales Interviews

Coming up with unique interview questions for your sales interviews is crucial for the best results. Candidates may have multiple interviews to attend, meaning you are likely to obtain better answers if your questions are a little different.

Here are some examples to get you started, as well as why they work.

When is your confidence the highest? When is it the lowest?

The key here is to make sure the candidate can remain flexible and assertive in the face of challenges or the unexpected, especially when cold calling. This question provides insight into whether they can thrive under pressure.

If the candidate says that their confidence is lowest in spontaneous situations or situations that require aggressiveness, follow up to make sure they have adequate experience, comfort and proficiency with cold calling. Sudden changes occur in sales all the time, making it crucial for salespeople to adapt and handle themselves well under pressure.

Additionally, you can ask the interviewee to perform a mock phone call with you or someone else in the office to further vet their capabilities. This process does not have to be very formal, but the exercise will instantly highlight how comfortable they are during such phone calls.

What is the most effective method of getting to know new prospects during a phone call?

If you would rather avoid subjecting candidates to the surprise of directly carrying out a call, this question is a good alternative.

By allowing them to explain how they would approach getting to know a client, you will receive instant insight into their overall approach to selling. If they are dismissive and do not believe getting to know their prospects is essential, you know the interviewee is not a good salesperson.

Similarly, if a candidate sees getting to know clients as complex, they are likely to struggle. A natural salesperson will not find such a task very challenging, and they will have a plan of action in place.

What has been your biggest challenge in creating customer relationships?

It is no secret how vital customer service is in sales. Customer service covers many different aspects and is definitely not “one size fits all.” Salespeople must adapt to every prospect while providing excellent customer service.

With this question, you are looking to see how many customer-related skills candidates have demonstrated in the past. You want a candidate who has a history of finding common ground with customers and the ability to build relationships from there.

Follow up with additional questions to understand what types of customers were particularly difficult for the candidate. How do these personalities compare to the customers that they will meet at your company? This information can help to determine culture fit as well as customer service skills.

What is the toughest goal you have ever set for yourself? How do you plan to top it?

A candidate with a high need for achievement will set very high standards for themselves and will hold themselves accountable for reaching their goals. A high-performer will be proud of the challenge goals they have accomplished but will have specific plans to top them—these types of salespeople are never satisfied.

If your candidate has not accomplished any challenging or tough goals, they may not have the innate personality to be a top-performing salesperson. Be sure to vet them further if you need someone who will bring in new business for you.

When was the last time you were rejected? What did you do to recover?

Rejection is inevitable in sales. It is critical that you understand how your sales candidate will react to the rejection that they will face as a natural part of their job. Rejection can be difficult to handle, but top-performing salespeople view rejection differently because of their high level of optimism.

You want to look for stories where the candidate remained resilient and stuck to their guns, even after a prospect rejected them. An optimistic salesperson will quickly put the situation into perspective and move on to their next goal. Top-performers do not get bogged down by rejection. They see it as a part of the job, and they know that every rejection puts them that much closer to a sale.

What hobbies do you spend the most time doing?

This question helps you identify how a person manages their free time. You will also gain insight into how they are likely to fit into your company culture, based on the activities they enjoy.

If a candidate displays impressive time management and has their priorities in check, they will likely bring these qualities into their professional working life. However, if their approach seems haphazard and unorganized, this could be cause for concern.

Tell me about a time you ignored your ego to help a co-worker.

Although it is a common stereotype, salespeople are notoriously skilled at describing their achievements and talking about themselves. It is often part of the job, after all.

A healthy ego is not necessarily a bad thing when it comes to getting results, but it can be challenging in a team environment. You are looking for salespeople who can put their ego aside for the sake of others, as this makes for a better team working environment in times that matter.

If a candidate fails to answer the question or appears to place their ego and needs over everything else, it is unlikely they will be a good fit for many sales teams.

If you had all the resources needed to start your own business, what would you do?

Asking this is a very effective example of a question that is a little outside the box and puts candidates on the spot—and for a good reason.

Many salespeople are attracted to the job because they are keen, natural entrepreneurs. Showcasing an impressive business spirit is a definite plus, even if it is just a pipe dream and not a real business venture they are actually considering.

You will not only get a sense of their goals and ideas but also gain insight into their pitching style. Explaining a fictional business still requires pitching skills, and candidates with natural sales ability should easily achieve this.

Do you have any questions for me about our company culture or services/products?

This question puts the candidate in the hot seat and is a good option to end an interview. By allowing your candidates to take the reins, you gain further insight into whether they genuinely care about the position.

Candidates that are genuinely keen to join your team should have prepared questions before the interview. Showcasing their enthusiasm to do a little research and learn more—that can be very revealing. If prospects hesitate or are unsure of what to ask, this is a clear indication they have not taken the effort to learn about your company in their own time, which is not a good sign.

Summarizing Extreme and Unique Interview Questions for Sales

Using extreme questions in a sales interview is an integral part of separating the good candidates from the bad. Natural salespeople will likely thrive under the challenge, maintaining impressive answers for the duration.

If you experience candidates who struggle to answer your questions and appear uncomfortable, perhaps they are not the best fit for your sales position.

Often far more effective than standard alternatives, extreme questions in a sales interview can cover many different factors. There is plenty to gain by asking questions about previous sales experience, and even an applicant’s character, as a key part of your interview process.