Questions to Ask During Sales Interview
Questions for a candidate interviewing for a quota-carrying sales role, covering quota attainment, pipeline sources, territory, commission mechanics and why deals are lost. Aimed at working out whether the number is reachable.
The questions
Open any question for the note
What is the quota for this role, and what did the team average against it last year?
Why ask it
The quota alone means nothing without attainment. A number set so that half the team clears it is a working plan; a number nobody has hit in two years is a way to avoid paying commission.
How many reps are on the team, and how many hit quota last quarter?
Why ask it
Ask for the count, not the percentage, because two of nine sounds worse than twenty-two percent and is the same fact. If the answer arrives as a story about a hard quarter, ask about the quarter before it.
Where does pipeline come from, and in what mix?
Why ask it
Inbound-heavy roles reward qualification and speed; outbound-heavy roles reward prospecting volume and a tolerance for silence. Being hired for one and measured on the other is the most common way a good rep fails.
What is the average deal size and how long is the cycle?
Why ask it
Together these tell you how many deals you must run at once and how long you will go without a close. A nine-month cycle with a quarterly quota means your first two quarters depend entirely on what you inherit.
Is this a new territory, or am I taking over an existing book?
Why ask it
An existing book comes with renewals and warm relationships plus whatever the last rep damaged. A greenfield patch means you build from nothing while carrying the same number as reps with pipeline.
How is the territory or account list divided, and who decides?
Why ask it
Ask what happens when a lead arrives from an account that is not clearly anyone's. Teams without a written rule for this lose a lot of energy to internal argument, and new reps lose those arguments.
What is the commission plan: rate, accelerators, caps, and when does it pay?
Why ask it
Get the mechanics rather than the on-target figure. Caps above target, payment on cash collected rather than signature, and clawbacks on churn all change what you actually earn from the same performance.
What is the ramp period, and is there a draw?
Why ask it
A ramped quota over two or three quarters signals the company knows how long the cycle is. A full number from month one, especially with a long cycle, means the plan expects you to miss.
Who signs the contract, and who else has to say yes?
Why ask it
Selling to a director who needs finance, legal and security approval is a different job from selling to an owner. The number of approvers is the best predictor of how much of your week goes on coordination.
What are the two objections your reps hear most, and what actually works on them?
Why ask it
This tests whether the team has shared knowledge or every rep improvises. If the interviewer cannot name the objections, you are being hired into a team with no playbook and will be building it yourself.
When deals are lost, what is the most common reason?
Why ask it
Losing to a named competitor is workable, losing on price suggests a positioning problem, and losing to no decision means the pain is not urgent enough. The third is the hardest to fix from a rep's seat.
How much of the quota comes from renewals or expansion versus new business?
Why ask it
A number that leans on renewals is easier to hit and teaches you less. It also means your earnings depend on a product and a support team you do not control.
What support does a rep get: SDRs, sales engineering, marketing?
Why ask it
Ask for the ratio, not the existence. One sales engineer shared across twelve reps is functionally no sales engineer during a busy quarter, and you will be running technical calls alone.
What discount can a rep approve without going up the chain?
Why ask it
Zero authority means every deal slows at the end, which matters most in the final week of a quarter. Very wide authority often means list price is fiction and discounting is how the team competes.
What tooling do reps use, and how much of the week goes on admin and reporting?
Why ask it
Ask how many hours a week go into the CRM and forecast calls. A team spending a day a week on reporting has less selling time than the quota assumes.
How long has the current sales leadership been in place?
Why ask it
A leader who arrived last quarter will change the plan, the territories and probably the quota. That is not a reason to decline, but it is a reason not to trust the numbers you are being shown.
What happened to the last person in this seat?
Why ask it
Promotion, a move to another territory, and a termination for missing target tell you different things about the number you are being offered. A pause before the answer is worth following up on.
How does the team handle a rep who misses two quarters?
Why ask it
Every sales floor has an answer, whether written down or not. A specific, humane process suggests the quota is believed in; an evasive answer suggests fast turnover you cannot see from outside.
What do your top reps do differently from the middle of the team?
Why ask it
The answer describes what the company actually rewards, which is not always what the interview measures. If the difference is entirely inherited accounts, the ranking is about territory rather than skill.
What is your customer churn rate after the first year?
Why ask it
High churn eventually reaches the sales team as clawbacks, harder references and a shrinking renewal base. It also tells you whether the promises being made in the room are the ones the product keeps.
Interviewing for a sales seat
Practical guidance for the conversation itself
Do the arithmetic in the room
Work backwards from the quota
Divide the annual number by average deal size to get deals needed, then multiply by cycle length and typical win rate to get the pipeline required. Say the result out loud and ask whether it matches what reps carry.
Ask for attainment as a count
Percentages hide small teams. Four of eleven reps at quota is the sentence you want, along with the same figure for the previous year.
Test the plan against a scenario
Describe a specific deal, signed in December, paid in March, and ask exactly when the commission lands and what happens if the customer cancels in month two.
What sales interviewers are testing
How you qualify
Your questions are the sample of your discovery technique. Asking about approvers, budget cycles and loss reasons demonstrates the behaviour they are hiring for better than any answer about your record.
Whether you take a straight answer well
When you hear something unwelcome, a low attainment figure or a capped plan, follow it with a question rather than a reaction. Interviewers watch how you handle a no.
Whether your numbers survive checking
Bring quota, attainment and deal sizes you can defend, and expect a reference to confirm them. Overstating attainment is the fastest way to lose an offer late.
Signs the number is not reachable
- Nobody can name a rep who hit quota in the last two quarters
- A full quota from month one on a cycle longer than a quarter
- Commission paid on collected cash with no visibility into billing performance
- The territory has been redrawn twice in a year
- Several reps in the same seat within eighteen months
- Marketing and sales give different numbers for where pipeline comes from