Four questions I always ask sales candidates in interviews

Being a sales and marketing manager of a busy technology company, I do my fair share of interviews for new sales candidates.  Some interviews go very well, some go very badly, but the majority tend to go ok, but just lack that spark that makes me think that the person sitting in front of me has what it takes to survive in a competitive sales environment.  And the reason for that is rarely down to expertise and experience, it’s down to mindset and how the candidate perceives what sales means to them.  All of which can be learnt and picked up quickly.

To share a little insight from what I’ve learnt up over multiple interviews, I’ve shared four key questions I ask in sales interviews that give me a better understanding of the candidate.


1. Tell me about a customer. In detail.

Many sales reps forget the most important thing.  The customer.  When I ask them to talk to me about one of their customers, they usually find this very difficult.  They might tell me about the turnover and industry the customer operates in, but little more.  To be a great sales person you need to understand your customer and be able to talk articulately about the customer, their challenges and objectives to sales management.

If a candidate can effectively explain a customer’s challenges and goals, alongside a backdrop of industry awareness about the commercial climate that customer is operating in, then I know they are well on their way to being able to align our products to those needs.


2. What have you read about selling?

I’m a great believer in self-improvement, and just because sales might not be recognised as a professional function in the same way that Marketing or Finance is with industry-recognised exams and accreditations, it doesn’t mean that sales people should rest on their laurels.  There is more quality content and research available than ever for sales people to share and consume and I am always interested in what sales and marketing books candidates have read recently to keep their skills sharp.

Books that I have found particularly influential in their field of selling include Rainmaking Conversations by Mike Shultz and John E. Doerr, Spin Selling by Neil Rackham and The New Strategic Selling by Miller and Heiman.

Showing that you have taken the time to regularly read key selling publications and books demonstrates that you view sales as a craft, rather than just a job.  It shows you are motivated, a self-starter and keen to improve.


3. What does failure mean to you?

We all know that selling involves a degree of failures, whether it be failing to get through a gate-keeper to a decision maker or losing a big deal at the last minute.

How you cope with that failure is what differentiates a good sales person from a great sales person.

Being able to bounce back quickly and move on to the next customer with a positive, proactive mindset reduces any time lost deliberating the sales loss.

Additionally, being able to critically assess your role in the deal loss and what you could have done better next time shows you can take accountability and recognise the areas that need to be improved on next time.  A failure to understand your own limitations is much worse than making a mistake in the first place.


4. What role did you actually play in your last sales success?

When sales people come in to see me from large, corporate organisations, it’s often difficult to understand what role the person actually played in their cited sales successes and won deals.

As C24 is an SMB company where sales people have to wear many hats and deliver all parts of the sales process end to end, it’s important to understand early on the roles that potential sales candidates have played in previous sales.

Larger companies give sales people the opportunity to work in large teams on deals, and some reps may only have responsibility for part of the process.  When they come to a smaller organisation, they struggle to deliver the entire sales function as they may have only been previously responsible for quoting, or telemarketing for instance.

Not having end to end sales experience is not a deal breaker, but having a candidate who can be upfront and straightforward about the role and responsibilities they previously had makes it easier to identify potential training requirements and see where they could fit within our sales organisation.

Sales reps will inevitably ‘big themselves up’ but hiring sales managers will appreciate your direct and honest approach early on before they hire you and quickly run into issues.  It’s better for both the candidate and manager in the long run.



I hope that’s given a little insight into how I approach sales interviews with prospective candidates and some of the things that sales managers are looking out for when interviewing reps.  I hear of some interviews where candidates are asked to “sell me a pen” but it’s not something I have experienced myself.  What’s the strangest thing you have been asked in a sales interview?





Image provided courtesy of Reyner Media (


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