Questions to Ask in a Sales Interview
Questions to ask in a sales interview, covering how many reps hit quota, how the comp plan actually pays, territory and pipeline, ramp length, deal size and cycle, support resources and turnover.
The questions
Open any question for the note
What percentage of the team hit quota last year?
Why ask it
This is the number that matters most and the one most often deflected. If fewer than half the team hit it, either the quota or the pipeline is broken, and neither gets fixed by hiring you.
What is the quota, and how is it set?
Why ask it
Ask whether it is built from territory data or divided evenly out of a company target. Quotas set from the top down tend to ignore whether a patch can actually carry them.
Walk me through the comp plan: base, variable, accelerators, and when it pays.
Why ask it
Ask whether commission is recognized on signature, on invoice, or on cash collected. The same headline number pays very differently under each, sometimes a quarter apart.
Is there a cap, and has anyone had a plan changed mid-year?
Why ask it
Plans being rewritten after somebody has a large quarter is a known pattern. Ask whether it has happened here and what the stated reason was.
What territory or account list would I get, and who had it before?
Why ask it
A patch worked hard for two years is not the same as a fresh one. Ask what the previous rep closed from it and what is already in the pipeline.
What is the split between inbound leads and pipeline I would source myself?
Why ask it
This defines the job more than the title does. Mostly self-sourced means prospecting for most of the week, whatever the posting called the role.
What is the average deal size and the average sales cycle?
Why ask it
Put both next to the quota and check whether the arithmetic works. Twelve deals a year on a six-month cycle means your first two quarters decide the year.
How long is the ramp, and is there a draw during it?
Why ask it
Ask what quota looks like in months one to three and whether any pay is guaranteed. Full quota from month one on a long cycle is a setup to miss.
Who do I sell to, and how many people are usually in a decision?
Why ask it
Single-owner deals and seven-stakeholder committees need different skills. Ask who typically signs and who typically blocks.
What does the sales process look like from first call to close?
Why ask it
Listen for whether stages are defined and actually enforced. Teams without a real process forecast badly, which shows up as pressure on reps at the end of every quarter.
How much of my day would be in the CRM?
Why ask it
Ask about required activity logging and how many dashboards someone reviews. Heavy administrative requirements take real selling hours out of the week.
Who supports a deal: sales engineers, marketing, legal, procurement help?
Why ask it
Support determines how many deals you can run at once. A rep doing their own demos and contract redlines carries a much smaller pipeline.
What is the win rate, and who do you usually lose to?
Why ask it
Named competitors and a specific loss reason mean the team studies its losses. Price as the only answer usually means it does not.
How are renewals and churn handled?
Why ask it
Ask whether you own renewals and whether churn claws back commission. Both change what a closed deal is actually worth to you.
How many reps have left in the past year, and why?
Why ask it
Sales turnover runs high everywhere, so ask for numbers rather than impressions. A team that has replaced most of its reps usually knows exactly why.
Who is the top performer, and what do they do differently?
Why ask it
The answer tells you whether success here comes from volume, from relationships, or from sitting on an inherited book, and whether that resembles how you sell.
How does the manager run the team week to week?
Why ask it
Ask about pipeline reviews, call coaching and forecast meetings. Managers who appear only at quarter end are managing the number rather than the reps.
What do customers ask for that the product cannot do yet?
Why ask it
Known gaps are what you will be selling against. A rep who learns them in month two has already lost deals in month one.
How does discount approval work?
Why ask it
Ask who approves and how long it takes. Slow approval chains kill deals in the last week of a quarter, which is when most of them close.
What would you want to see from me in the first ninety days?
Why ask it
A specific answer means there is an onboarding plan. An answer only about hitting the number means you will be building your own ramp.
Reading a Sales Job Before You Take It
Practical guidance for the conversation itself
Do the Arithmetic in the Room
Quota, deal size and cycle have to agree
Divide the quota by the average deal size to get the number of deals you need, then multiply the cycle length out across the year. If the answer requires you to close deals you have not started yet, say so and ask how the last person managed it.
Attainment tells you more than the plan does
A generous comp plan on a quota nobody reaches pays less than a modest plan most of the team clears. Ask for the attainment percentage first and treat everything else as secondary.
Ask about the patch, not the product
Two reps on the same team with the same plan can earn very differently because of territory. Ask what the patch produced last year and what is already in the funnel.
Numbers to Leave With
- Percentage of reps at or above quota last year
- Quota figure and how it was derived
- Average deal size and average cycle length
- Ramp period, ramped quota, and any guaranteed draw
- Commission trigger point: signature, invoice, or collection
- Inbound versus self-sourced pipeline split
- Rep headcount now compared with twelve months ago
Common Pitfalls
Being sold to instead of selling
Sales interviews are run by people who are good at enthusiasm. Write your questions down beforehand and work through them, because a good story about the market can otherwise fill the whole hour.
Accepting on-target earnings as an expectation
It is a modeled figure, not a forecast. Ask what the median rep actually earned last year, which is a different and far more useful number.
Not asking why the seat is open
Growth, a promotion and someone missing quota for three quarters lead to very different first months. Ask, and ask what happened to their pipeline.
Skipping the plan document
Ask to read the compensation plan before you sign anything. Clawbacks, caps and payment timing live in the details, not in the conversation.