35 Interview Questions for Sales Representatives (SDR, AE & Sales Manager)

Sales is the one department where a bad hire does not just cost you their salary — it costs you pipeline, deals, and customer relationships. Research shows the average cost of a failed sales hire is $115,000 when you factor in recruiting, training, lost deals, and the time to backfill the role.

The tricky part? Salespeople are professionally trained to sell themselves. They interview well by default. Your job as a hiring manager is to get past the polish and evaluate whether they can actually sell your product, to your buyers, in your market.

The questions below are organized by skill area and role level (SDR, AE, and Manager) so you can build interviews that reveal real selling ability. For instant, role-specific questions, try our free AI interview question generator.

Essential for SDRs and AEs — these questions reveal whether candidates can build pipeline, not just close what is handed to them.

1. Walk me through your daily prospecting routine when you are starting in a new territory.

What to look for: A structured approach — account research, multi-channel outreach (phone, email, LinkedIn, video), personalization, and volume targets. Red flag: "I wait for inbound leads."

2. How do you research a prospect before reaching out?

What to look for: Use of LinkedIn, company news, 10-K filings, tech stack tools. Depth of research should match deal size — enterprise reps should go deeper than SMB reps.

3. What is your approach to writing a cold email that gets a response?

What to look for: Personalization, short and direct, clear value proposition, specific CTA, and awareness that subject lines matter. Ask them to write one live if possible.

4. How do you handle a prospect who says "not interested" on a cold call?

What to look for: Resilience without pushiness. Good reps acknowledge, ask one clarifying question ("May I ask what your current approach is?"), and know when to respectfully follow up later.

5. How do you prioritize your accounts? Not every lead is equal — how do you decide where to focus?

What to look for: ICP understanding, account scoring methodology, ability to balance high-value targets with quick wins, and time management discipline.

6. Tell me about a deal that started from a cold outreach. How did you break in?

What to look for: Creativity, persistence, multi-threading (reaching multiple contacts), and the ability to create interest where none existed.

These questions assess whether candidates can move deals across the finish line — not just keep them in pipeline.

7. Walk me through the biggest deal you have closed. What was the timeline and what were the key moments?

What to look for: Deal complexity awareness, multi-stakeholder navigation, ability to articulate the buying process (not just their selling process), and specific dollar amounts.

8. How do you handle a prospect who keeps pushing back on price?

What to look for: Value-based selling (not just discounting), understanding of procurement tactics, ability to trade concessions rather than just give them, and knowing when to walk away.

9. Describe a deal you lost that you expected to win. What happened?

What to look for: Self-awareness and honest analysis — not just blaming the prospect, product, or pricing. What did they learn and change in their process?

10. How do you create urgency in a deal without being pushy?

What to look for: Business case building, tying to prospect's timeline and pain, mutual action plans, and genuine reasons to act now (not fake scarcity).

11. What is your process for multi-threading into an organization?

What to look for: Understanding that single-threaded deals are fragile. Strategies for reaching champions, economic buyers, and blockers simultaneously.

12. How do you handle it when a champion leaves the company mid-deal?

What to look for: Composure, quick action to find a new champion, leveraging the departed champion for introductions, and realistic assessment of deal viability.

Coachability is the strongest predictor of sales success in new hires. These questions test it directly.

13. Tell me about feedback from a manager that changed how you sell.

What to look for: Specific feedback, what they changed, and measurable improvement. Red flag: struggling to recall any feedback or being defensive about it.

14. What is the biggest professional setback you have experienced? How did you recover?

What to look for: Resilience, growth mindset, concrete actions taken, and ability to maintain performance during difficult periods.

15. How do you handle a month where you are way behind quota?

What to look for: Pipeline analysis, activity increase, creative deal acceleration, and honest communication with management — not panic or sandbagging the next month.

16. Describe your sales process from first touch to close. Walk me through a recent example.

What to look for: A real, structured process — not random activity. Discovery, qualification, demo, proposal, negotiation, close. Does their process match your sales cycle?

17. How do you prepare for an important sales call or demo?

What to look for: Research depth, agenda preparation, anticipated objections, tailored messaging, and follow-up planning. Great reps treat every call like it matters.

18. If I called your last manager right now, what would they say is your biggest area for improvement?

What to look for: Self-awareness and honesty. The answer should be specific and believable — not a humble brag disguised as a weakness.

19. How do you learn a new product well enough to sell it confidently?

What to look for: Structured learning approach — product training, shadowing top reps, customer conversations, and hands-on product use. Speed of ramp matters.

20. What questions do you ask during a discovery call?

What to look for: Open-ended questions, focus on pain and business impact (not just feature needs), understanding of decision process, and active listening signals.

21. How do you handle a prospect who wants to jump straight to a demo without a discovery call?

What to look for: Diplomatic pushback — framing discovery as beneficial to the prospect ("so I can tailor the demo to your situation"), while being flexible enough to adapt.

22. How do you sell against a competitor you know is better in certain areas?

What to look for: Honest positioning, reframing around the prospect's priorities, selling strengths without bashing competitors, and knowing when you are genuinely not the right fit.

23. Sell me this [your product] in 60 seconds.

What to look for: Research (did they look at your product before the interview?), clear value proposition, audience awareness, and confidence — not perfection.

For sales manager and director roles, add these questions to assess leadership and coaching ability.

24. How do you build a sales team from scratch? What is your first 90-day plan?

What to look for: Process first (playbook, ICP, messaging), then people (hiring profile, ramp plan), then optimization (metrics, coaching cadence).

25. How do you coach an underperforming rep?

What to look for: Diagnosis before prescription — is it skill, will, or product-market fit? Specific coaching methods, clear improvement timelines, and willingness to make tough calls.

26. How do you forecast accurately?

What to look for: Pipeline stage methodology, commit vs. best-case discipline, deal-level inspection, and historical accuracy awareness.

27. How do you handle a top performer who is toxic to the team?

What to look for: Direct confrontation of the behavior, clear expectations, willingness to let top performers go if behavior does not change, and protection of team culture.

28. What sales metrics do you track daily, weekly, and monthly?

What to look for: Activity metrics (daily), pipeline health (weekly), and revenue outcomes (monthly). Understanding of leading vs. lagging indicators.

29. How do you build a culture of accountability without micromanaging?

What to look for: Clear expectations, transparent dashboards, regular 1:1s, celebrating wins, and trusting reps while maintaining standards.

30. Why sales? What keeps you motivated when it gets hard?

What to look for: Genuine passion — competition, financial rewards, customer impact, or problem solving. Beware answers that sound rehearsed or generic.

31. What is your biggest professional win? Tell me the full story.

What to look for: Specifics over generalities. The story should reveal their role, the challenge, and the outcome — with honest credit sharing.

32. How do you handle rejection? Give me a specific example.

What to look for: Emotional resilience, perspective-taking, and the ability to move on quickly without it affecting the next call or meeting.

33. What type of sales environment do you thrive in?

What to look for: Alignment with your company culture — high-activity SMB vs. strategic enterprise, startup scrappiness vs. structured process, individual vs. team-oriented.

34. If you could sell anything, what would it be and why?

What to look for: Insight into their values and interests. Great answers reveal passion for the problem space, not just the commission check.

35. What questions do you have for me about this role?

What to look for: Thoughtful questions about the product, market, team, quota, and growth path. Red flag: no questions, or only asking about comp and PTO.

Structure Your Sales Interview Process

For most sales roles, we recommend:

1. Phone Screen (20 min) — Prospecting and behavioral questions
2. Mock Sales Call (30 min) — Live role-play where they sell to you
3. Deep Dive (45 min) — Closing, negotiation, and deal walk-through
4. Culture & Values (30 min) — Motivation, coachability, and team fit

Generate custom sales interview questions for any role with our free AI interview question generator. Build your complete sales hiring pipeline — from job posting to offer — with BorovaHR's free plan.