Why this matters:

For the best sales reps, timing is everything. And sometimes, it’s just not the right time to attempt a sale. For example, a prospect might not be in the right place mentally, or the opportunity may be premature — due to external circumstances, a still too-new relationship, or similar factors. At these times, pitching may have a counter-effect, diminishing rather than elevating brand perception.

What to listen for:

  • A sensitivity to when the time is right to pitch
  • A recognition of how best to build trust and rapport — and when those items are in place
  • The ability to recognize tone, body language, or other non-verbal cues

Why this matters:

Any sales rep responsible for generating leads will be given a territory and perhaps a prospecting list, and it will be their job to work through it. This question will reveal the candidate’s strategies for generating interest, whether through a combination of cold calling, cold emails, LinkedIn connections, or other effective tactics.

What to listen for:

  • Seasoned approaches, along with pros and cons for each
  • A track record of success in generating leads
  • Enthusiasm for the challenges of cold outreach

Why this matters:

Sales reps in all industries benefit from effective marketing. In some cases, marketing brings prospects into and through the company’s sales funnels. In other cases, it establishes trust, creating a belief in the benefits and reliability of a product, service, or brand. This question explores the candidate’s understanding of how good marketing can help them find prospects, bolster their pitch, and close deals.

What to listen for:

  • An active role in directing or leveraging existing marketing assets
  • An understanding of the interplay between sales and marketing — in your industry
  • Specific ideas for how marketing can help them in the role they’re applying for

 

Why this matters:

Communication doesn’t always go as planned, since it can be rife with assumptions and other misalignments. This question will shed light on how the candidate confirms they’re on the same page with a sales lead — and the steps they might take to overcome any miscommunication and re-establish connection.

What to listen for:

  • A recognition that communication isn’t perfect
  • Active listening for both context and subtext
  • The desire to truly understand what a speaker is conveying — and how to act on it

Why this matters:

Selling involves changing mindsets — sometimes drastically. This question enables the candidate to brag about a past success story in which they transformed the viewpoint of a lead or prospect that was initially resistant and skeptical into an enthusiastic purchaser — and even a long-term fan.

What to listen for:

  • Pride in a job well done
  • Confidence in their ability to overcome objections and persuade others
  • A successful streak of conversions

Why this matters:

In any consultative sales environment, it’s important for the lead or prospect to share their needs and circumstances so that sales reps can design the best solutions — even with those that are more private, or otherwise reluctant to open up. This question will give you insight into the candidate’s tactics for making their prospects feel comfortable sharing more information.

What to listen for:

  • Ability to recognize and overcome the source of a client’s hesitancy to connect
  • Past anecdotes that demonstrate successful connections
  • Confidence in converting and closing a range of personalities

Why this matters:

A sales representative juggles many workplace responsibilities — which may make it easy to neglect one aspect of their work, fail to meet goals, and even become overwhelmed. This question sheds light on a candidate’s time management skills, including how they establish a routine, prioritize, and stay calm, focused, and disciplined.

What to listen for:

  • The importance of establishing a routine
  • A steady sense of focus and self-discipline
  • An energetic, can-do approach to being busy

Why this matters:

How a candidate thinks about their work gives a glimpse into their level of drive and determination. Here, you’ll be looking for candidates that set high standards — and are at least partially motivated by monetary commissions. This question may also reveal the candidate’s future goals, and how they plan to achieve them.

What to listen for:

  • The candidate’s own definition of success — and how it helps keep them motivated
  • The effectiveness of monetary incentives to generate stellar results
  • A constant drive to learn and improve

Why this matters:

This question offers insight into the candidate’s short- and long-term career goals. It provides an opportunity to see if their goals align with your company’s or department’s — and also to find out what excites the candidate about the role. Watch for excitement and enthusiasm, and a sense that the candidate has done their research.

What to listen for:

  • A sense of the candidate’s passion for what you sell
  • Strong ambition and drive to achieve
  • Excitement about salesmanship — and an active interest in growing within the role
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