20 Questions

Questions to Ask at the End of a Sales Interview

Strategic questions to evaluate comp structure, sales cycle, quota expectations, and whether the sales role will set you up for success.

1

What does the comp plan look like—base, commission structure, and realistic OTE?

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Why this works

Clarifies earning potential and whether the commission structure rewards performance fairly.

2

What percentage of the sales team is hitting quota, and what's the average attainment?

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Why this works

Shows whether quotas are realistic or set so high that most reps fail.

3

How is quota set, and does it ramp up over time for new hires?

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Why this works

Reveals whether you'll have a grace period to learn or be expected to close from day one.

4

What does the sales cycle look like from prospecting to close?

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Why this works

Clarifies time to revenue and whether you'll see commission quickly or wait months.

5

How are leads generated and distributed—inbound, outbound, or a mix?

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Why this works

Shows whether you'll be hunting from scratch or working a qualified pipeline.

6

What does the onboarding and training process look like for new sales reps?

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Why this works

Assesses whether you'll be set up for success or left to figure it out alone.

7

What CRM and sales tools does the team use, and how mature is the tech stack?

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Why this works

Reveals whether you'll have modern tools or be slowed down by legacy systems.

8

What does a typical day or week look like for someone in this role?

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Why this works

Helps you visualize the workflow and whether the role matches your style.

9

How does the team collaborate—are there regular pipeline reviews, team meetings, or coaching?

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Why this works

Shows whether the culture is supportive or every-rep-for-themselves.

10

What are the biggest challenges reps face in this role, and how does the company support overcoming them?

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Why this works

Surfaces pain points and whether leadership is committed to helping reps succeed.

11

What does career progression look like—AE to senior AE, team lead, or management?

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Why this works

Clarifies whether there's a path up or if you'll need to leave to advance.

12

How competitive is the sales landscape, and what differentiates your product in the market?

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Why this works

Assesses whether you'll be selling a strong product or fighting an uphill battle.

13

What's the average tenure of sales reps on the team?

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Why this works

Reveals retention and whether the role is sustainable or a revolving door.

14

How does the company handle territories or account assignments?

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Why this works

Clarifies whether you'll have a fair book of business or inherit a tough patch.

15

What metrics or KPIs beyond quota are used to evaluate performance?

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Why this works

Shows what activities and behaviors are tracked and rewarded.

16

How does the team celebrate wins and handle losses?

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Why this works

Reveals culture and whether success is recognized or taken for granted.

17

What does the ideal candidate for this role look like in terms of skills and experience?

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Why this works

Helps you assess fit and position yourself as the right person for the job.

18

Can you share an example of a recent deal that went well and what made it successful?

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Why this works

Provides insight into what good looks like and the factors that drive wins.

19

What's the commission payout schedule—monthly, quarterly, or at deal close?

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Why this works

Clarifies cash flow timing and whether you'll wait long periods to get paid.

20

What are the next steps in the process, and when should I expect to hear back?

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Why this works

Closes confidently and sets clear expectations for follow-up.

Evaluating a Sales Opportunity

Expert tips and techniques for getting the most out of these questions.

Know Your Deal-Breakers

Base salary floor—can you survive if commission is slow?
Quota attainment—if <70% of reps hit, it's a red flag.
Product-market fit—selling a bad product is soul-crushing.
Support and training—lone wolves struggle without infrastructure.

Red Flags in Sales Roles

Vague or evasive answers about quota attainment.
Sky-high OTE with tiny base salary and uncapped theoretical earnings.
High churn—if reps leave quickly, the role is likely broken.
No ramp period or unrealistic expectations for new hires.

Closing the Interview Strong

1
Summarize your fit and enthusiasm based on what you learned.
2
Ask for feedback on your candidacy and address concerns on the spot.
3
Request intros to current reps to get the unfiltered truth.
4
Follow up with a thank-you email that reinforces your value.

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