Securing a sales role is easier said than done. It entails more than a strong résumé and confidence in hitting quotas. Hiring managers often go beyond standard inquiries and dive into lesser-known scenarios and personality-based questions to identify top talent. While many candidates rehearse answers to common questions like “What is your greatest strength?” or “Tell me about a time you closed a major deal,” there’s an entire category of interview questions for a sales position that often catches applicants off guard.
This article will explore those uncommon questions, explain why they matter, and help you prepare to respond. Whether you’re new to sales or a seasoned professional, understanding these inquiries can be the difference between a good impression and a great job offer.
The Hidden Agenda Behind Uncertainty
Interviewers in the sales industry are tasked with evaluating more than your sales record. They want to understand how you think, how you respond to pressure, and how well you adapt to change. Sales is as much about people and psychology as it is about numbers. Therefore, seemingly odd or unrelated questions often serve a deeper purpose.
Unconventional questions are used to:
- Gauge emotional intelligence
- Test resilience and adaptability
- Assess cultural fit within a competitive team
- Reveal creativity and problem-solving skills
- Understand intrinsic motivation and authenticity
1. “Sell Me This Pen”—But With a Twist
Variation: “Sell me this pen, but don’t mention its features.”
This classic role-play question is often reimagined to test a candidate’s ability to pivot. By removing the ability to focus on features or benefits, the interviewer wants to see if you can engage emotionally, identify pain points, or trigger urgency.
What They’re Looking For:
The interviewer wants to see how well you can connect a product to a need, even when typical selling points are off-limits. Can you identify what drives the buyer?
How to Respond:
Ask questions first. Instead of diving into a pitch, say, “Before I recommend a pen, can I ask what you typically use one for?” This shows you’re customer-focused rather than script-driven.
2. “What Would You Do If a Client Asked for a Discount You Can’t Offer?”
This question tests your ability to balance empathy with company policy. Sales professionals often walk a fine line between securing a sale and maintaining margin integrity.
What They’re Looking For:
Your response reveals negotiation skills, ethical boundaries, and your ability to stand firm without damaging relationships.
How to Respond:
Demonstrate that you’re willing to seek creative alternatives. For example:
“I’d acknowledge their concern and explore other ways to add value—perhaps through flexible terms, bundled services, or post-sale support—rather than cutting price.”
3. “What’s the Last Sales Technique You Learned—and Why Did It Stick?”
This question explores your commitment to professional development. Sales is an evolving field, and staying current with trends is necessary.
What They’re Looking For:
A candidate who proactively seeks out new strategies, reflects on what works, and applies new learning in practical contexts.
How to Respond:
Be specific. Mention a podcast, book, or webinar and explain how the method impacted your performance. For example, “I recently started using the ‘Challenger Sale’ approach to reframe client perspectives, and it’s helped shorten my sales cycle significantly.”
4. “Describe a Time You Lost a Sale—What Did You Learn?”
Talking about failure isn’t a walk in the park, but this question distinguishes self-aware candidates from blame-shifters.
What They’re Looking For:
The interviewer wants to know if you reflect on setbacks, extract lessons, and use that insight to improve.
How to Respond:
Avoid generic answers. Share a specific experience and emphasize the takeaway. For example:
“I misread the client’s timeline and pushed too aggressively. I learned to confirm urgency early and prioritize listening over assumption.”
5. “What Motivates You More: Recognition, Money, or Mastery?”
This behavioral question uncovers what drives you, which can indicate how well you’ll mesh with the company’s culture and incentives.
What They’re Looking For:
They’re trying to predict your longevity and engagement. A team culture emphasizing peer recognition may not satisfy someone strictly driven by commission.
How to Respond:
Be honest but strategic. A balanced answer might be:
“I’m highly motivated by mastering new challenges and improving my close rate—but I also appreciate recognition for hitting targets. I find that both drive me to stay at the top of my game.”
6. “How Do You Handle Rejection—Especially When You’re Close to Meeting Your Goal?”
It’s no secret that sales are full of near-misses. This question reveals emotional resilience and professionalism under pressure.
What They’re Looking For:
Interviewers want to see whether you can take rejection in stride without letting it derail your momentum or impact team morale.
How to Respond:
Frame your response to show emotional control and positive reframing. For instance:
“I try not to internalize rejection. If I lose a deal, I follow up and understand why, then use that to refine my approach. I focus on what’s still in the pipeline and maintain a high activity level.”
7. “How Would You Sell a Product You Don’t Believe In?”
Though tricky, this question explores your ethical stance and adaptability.
What They’re Looking For:
Are you someone who values honesty? Do you know how to represent a brand even when you have reservations?
How to Respond:
Your answer should reflect integrity:
“If I couldn’t align with a product’s value, I’d voice my concerns internally. It’s hard to authentically sell something I don’t believe in. I’d prefer to work on understanding its use cases or advocate for improvements.”
8. “What’s Something You’ve Taught Yourself That Helps You in Sales?”
In this specific question, the spotlight is on initiative and self-improvement. Independent learning is a hallmark of top performers.
What They’re Looking For:
They’re interested in whether you wait to be trained or proactively seek knowledge that benefits your work.
How to Respond:
Tie your learning to practical sales outcomes. For example:
“I taught myself data visualization using Excel to present client ROI more effectively. It’s helped clarify the value of our services and made negotiations smoother.”
9. “If a Competitor Offered You a Job Right Now, What Would You Do?”
This curveball tests loyalty and strategic thinking. It can also reveal how much you value the prospective employer.
What They’re Looking For:
They’re not necessarily testing your loyalty—they want to see how you make decisions and assess opportunities.
How to Respond:
Balance diplomacy with decisiveness:
“I’d understand what makes them interested, but I’d consider the long-term growth and advancement and the values of where I’m applying. I prioritize alignment over quick wins.”
10. “Describe the Best Sales Team You’ve Ever Worked With—And What Made It Work”
This is a culture-fit question disguised as a reflection on teamwork.
What They’re Looking For:
Hiring managers want to know what they value in a team and whether those values align with their existing culture.
How to Respond:
Focus on collaboration, transparency, and support:
“The best team I worked with shared wins, learned from losses, and held each other accountable without ego. We celebrated progress and lifted each other through slumps.”
11. “How Do You Prioritize Leads in a Saturated Market?”
In competitive industries, prioritization can make or break a pipeline.
What They’re Looking For:
This tests your strategic thinking and use of data. Can you distinguish between warm leads, dead ends, and high-opportunity prospects?
How to Respond:
Discuss how you use scoring, past behavior, or industry segmentation. For instance:
“I prioritize based on buyer readiness, decision-making power, and historical conversion patterns. I also cross-reference leads with CRM insights to spot high-likelihood segments.”
12. “If We Were to Call One of Your Clients, What Would They Say About You?”
A subtle reference-check question that encourages honest self-evaluation.
What They’re Looking For:
Insight into your client relationships, communication style, and reputation.
How to Respond:
Be specific and highlight soft skills:
“I believe they’d say I’m consistent, responsive, and honest—even when it’s not what they want to hear. I work to build trust beyond transactions.”
13. “What Do You Think We’re Doing Wrong in Our Sales Process?”
This bold question tests whether you’ve done your homework.
What They’re Looking For:
Your critical thinking, research skills, and courage to offer constructive feedback.
How to Respond:
Approach this delicately.
“From what I’ve seen, your brand has strong positioning, but your case studies aren’t easy to find. Highlighting those more could reinforce buyer confidence earlier in the cycle.”
14. “What Would You Do If a Colleague Tried to Poach One of Your Clients?”
This question assesses your interpersonal maturity, conflict resolution skills, and ability to maintain professionalism under challenging circumstances.
What They’re Looking For:
Sales environments can be highly competitive, and situations involving territory disputes or client ownership may arise. The interviewer wants to know if you’ll escalate unnecessarily, handle things diplomatically, or let resentment fester.
How to Respond:
Demonstrate that you’re a team player who values communication and fairness:
“I’d speak directly with my colleague first to understand the situation—sometimes it’s a simple misunderstanding. If it needed further resolution, I’d bring in a manager with full transparency, focusing on what’s best for the client and team.”
15. “How Would You Adjust Your Pitch for a Skeptical Buyer Who’s Heard It All Before?”
Experienced buyers, especially in B2B industries, are often immune to typical sales pitches. This question evaluates your creativity, adaptability, and customer-centric mindset.
What They’re Looking For:
Can you identify fatigue or skepticism in a buyer and still find a way to engage meaningfully? Do you personalize your approach or push harder with the same strategy?
How to Respond:
Explain how you pivot and reframe value based on what the buyer truly cares about:
“I’d ask open-ended questions to uncover pain points and tailor my approach around their goals. Instead of relying on a pitch, I’d shift to a collaborative conversation where I position myself as a partner, not just a vendor.”
Final Thoughts
The most insightful interview questions for a sales position are designed to go beyond the résumé and dig into how you think, learn, adapt, and sell under pressure. By preparing for these lesser-known questions, you not only show you’re ready for anything but also allow you to display emotional intelligence, ethical grounding, and strategic vision.
Expect the Unexpected
Infinity Management Group has you covered if you want to know how to ace interviews for a coveted sales position. We offer personalized career coaching, industry insights, and sales mentorship programs to help you stand out. Our team understands what top-tier companies are looking for and can help you prepare for even the most unpredictable interview questions.
Partner with us to start shaping a successful and fulfilling sales career!