1. “Tell me about a deal you have won?”

How a sales rep wins a deal says a lot about whether they’ll fit in with your sales culture. This is a good way to start the interview, because who doesn’t like to brag about a big deal?

2. “Tell me about a deal you have lost?”

Here, you’re looking for accountability. If they won’t talk about a deal they lost, call them a cab. Interview is over. Everyone has lost a deal at some point. A good salesperson is always looking for ways to improve and isn’t afraid to admit their mistakes.

3. “What did your W-2’s look like the last couple of years?”

A smart rep won’t tell you right away. They shouldn’t do it during a sales interview, either. The best sales reps will continue to push for further clarification of the role, your needs, what it will take to be successful and their value to the company.

4. “What’s worse? Not making quota every single month or not having happy customers?”

Depending on your company’s goals, either answer could be the right one. But beware of reps who will prioritize quota over truly giving customers what they need – or withholding from them what they don’t.

5. “How do you divide up your time?”

In sales, time is money. Managing a sales pipeline, closing deals and servicing relationships with existing accounts takes a lot of time. Good salespeople squeeze hours out of minutes and weeks out of days, and are always looking for ways to close deals faster.

6. “How do you research prospects before a call or meeting? What information do you work for?”

Neglecting to use LinkedIn to research clients is not a viable option in today’s sales environment. Ensure that candidates are searching for personal commonalities in addition to professional information so they can tailor their communication as much as possible. Looking into company trigger events would be the cherry on top.

7. “Who are you most comfortable selling to and why?”

Listen for whether they answer with a description or an ideal buyer, or a particular demographic with no tie-in to the buying process. Depending on your product or service, the second type of response might pose a problem.

8. “How do you find your leads?”

Beware of the sales rep who is handed a steady flow of leads, has the best accounts or can hide under the air cover offered by a big brand name firm. Nothing wrong with big companies but often their sales reps haven’t had to make a cold sales call to a stranger for decades.

9. “What are three adjectives a former client would use to describe you?”

Listen for synonyms of “helpful”, as a consultative approach is becoming increasingly important for modern sales.

10. “What book is on your nightstand?”

Top sales reps are self-improvement junkies! Doesn’t matter if they have been in the business for 4 weeks or 4 decades, the top 10% are always looking for ways to improve and gain a competitive edge.

11. “How do you keep a smile on your face during a hard day?”

Appraise the person’s attitude towards rejection. Do they need time to shake off an unpleasant conversation? Or do they bounce back immediately?

12. “What are your short-term goals?”

Long term goals are fine but they all usually sound the same. You want someone that can get off to a fast start with minimal hand holding. A great candidate will have already thought about, planned and prepared for how they will build a pipeline and get to their first commission check as fast as possible.

13. “Why you?”

Remember, this is sales call for the candidate – their most important sales call. And if they can’t effectively sell themselves, a product they’ve lived with for years, how will they effectively sell your product?

14. “Why us?”

Good sales candidates always have multiple opportunities to choose from and the ones you hire should know your unique value proposition and why your company is their best choice versus all of the other alternatives in the marketplace.

15. “Why now?”

Why is now the right time for you to make a change? Turn on your excuse radar and listen closely to this answer. The bottom line is the good candidates ALWAYS FIGURE IT OUT, regardless of market conditions.



About Sales Search International

Sales Search International is one of the oldest and largest search firms in the country for sales and marketing talent in the technology and software industries and is ranked in the top 5% of all search firms in all industries by the world’s largest executive search network.

Our search team’s expertise is divided into the following areas. To satisfy our clients, we continue to broaden our scope by staying informed of the issues and trends shaping tomorrow’s marketplace within these categories. Our team of nationally recognized award winning recruiters have a proven track record of providing the Information Technology and Software Industries with quality candidates that will help your company achieve long and short term revenue goals:

Areas of Specialization

Enterprise Software – Cloud Computing / SaaS – Big Data / Analytics – Mobile Computing – Unified Communications – Software Defined Networking – Traditional Networking – Cyber Security –  Internet of Things – E-Commerce – IT Consulting / Professional Services

Sales Search International – www.sales-talent.com – 717.737.7500


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