Questions to Ask a VP of Sales in an Interview
Questions to ask a VP of Sales in an interview, written mainly for the candidate, whether the seat is a rep's, a first-line manager's or a leadership role reporting to them. They open with what only the VP can tell you, the plan for the year and how the team is tracking against it, then move through quota, ramp and comp, pipeline and deals, how they lead, and the team you would join. Most of that first group still works after you are hired, as questions to ask a VP of Sales in a skip-level meeting or in the weeks after a new one takes over the team. The last group is for the other side of the table: a founder or chief executive interviewing a VP of Sales candidate.
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The questions
Each question, and why to ask it
The plan
What are your top two or three priorities for the sales organization this year, and which of them is this hire for?
Why ask it
A VP who can list them without pausing has a plan the team has heard before. The second half tells you whether the seat is central or a gap being filled, and a role tied to none of the priorities is exposed when the plan changes.
How did the team finish against its number last year, and how is this year tracking?
Why ask it
The team total and individual attainment can tell different stories: a team can make plan on two big deals while most sellers miss. Ask for both, and check whether this year's target rose faster than headcount did.
What is the hardest problem in front of the sales team right now?
Why ask it
A VP's answer usually sits a level above a manager's: a segment that will not convert, a rival's pricing, too few leads for the headcount. Follow up on what is being done about it, and on whether this role is part of the fix or just exposed to the problem.
What has to be true this year for the team to make its number?
Why ask it
This surfaces the dependencies outside the sales team: a product release, a pricing change, a hiring plan, a market assumption. If the plan rests on something not yet built, that risk becomes your quota.
Where is growth supposed to come from: more reps, bigger deals, new segments or new products?
Why ask it
Each answer changes the job. More reps means territories get split, bigger deals mean longer cycles with more people in them, and a new segment means somebody has to sell without reference customers. Ask which of those lands on this seat.
If the plan works, what does this sales team look like three years from now?
Why ask it
This is the picture you would be joining early: a move upmarket, a second product, new regions, a team twice the size. Check that the picture still has a place for someone who started in the seat you are interviewing for, since a company moving to larger customers may not keep its small-business team.
How many sellers do you plan to add this year, and what happens to existing territories when they start?
Why ask it
Hiring is how a growing sales team shrinks each patch. A leader who has thought it through can say how accounts get reassigned and whether quotas come down with them. 'We'll figure it out' means the people already in seat pay for the growth.
What did you get wrong about the market last year?
Why ask it
A specific miss, and what changed afterwards, is good evidence of a leader who adjusts. A polished non-answer from someone whose job includes giving the chief executive bad news is worth weighing.
What do customers ask for that the product does not do, and how much pull does sales have on the roadmap?
Why ask it
Every seller runs into product gaps. What the VP can tell you is whether feedback from deals reaches the people who decide what gets built, or whether reps have been selling around the same hole for years.
Is pricing or packaging likely to change this year?
Why ask it
A price rise or a switch of model, per seat to usage for example, changes deal size, cycle length and what your quota is really worth. Ask whether this year's quotas were set before or after the change was planned.
How is the company funded right now, and is this year's sales hiring paid for out of revenue or out of a raise?
Why ask it
If the hiring is paid for by a funding round, there is a date by which the numbers need to work, and it helps to know roughly when. At a private company the VP may not be free to share figures, so ask what they are able to say and notice how readily they say it.
Who do you report to, and how often are you in front of the CEO and the board?
Why ask it
A sales leader with a direct line to the chief executive can get pricing, product and headcount decisions made. One who reports through several layers ends up relaying your problems upward and waiting, the same as you would.
Which parts of the selling job here have been automated or handed to AI tools in the past year?
Why ask it
Account research, call notes and follow-up emails are the usual candidates. The telling part is what happened to the time saved: activity targets went up, SDR seats were cut, or reps got more hours with customers.
The numbers
What does the team look like today: how many sellers, and which segments do they cover?
Why ask it
An easy one that gives you the shape of the org before anything contentious: headcount, segments, how many managers. It also gives you the denominator for every percentage that follows, since 'most of the team' means one thing with six sellers and another with sixty.
How many of your sellers hit quota last year, and out of how many?
Why ask it
A percentage on its own hides too much, so get the count and find out whether it covers everyone who carried a number or only the reps who were there all year. If well under half got there, the quota is closer to a hope than a plan, and the on-target pay you are being quoted rests on it.
What is the quota for this seat, and how did you arrive at that number?
Why ask it
The VP is usually the person who cuts the company target into individual numbers, so they can say whether yours came from account data or from a total divided by headcount. Ask what the last person in the seat finished at against it.
How long is ramp before someone is expected to carry a full number?
Why ask it
Compare the answer with the sales cycle. If ramp is three months and deals take nine, you would carry a full quota for half a year before your first deal could close. Ask what a ramping rep's number looks like month by month.
What does the comp plan look like, and when was it last changed?
Why ask it
You want the base and variable split, the accelerators, and whether commission is paid on booking, invoice or cash collection. A new plan each fiscal year is common. A change in the middle of one is the thing to ask about, along with who came out behind.
What are on-target earnings for this seat, and what did the median seller take home last year?
Why ask it
The middle of the team says more than the target or the top earner's figure, since one large deal can make a whole plan look generous. If the median sits well below target, that gap is a fair guess at what the headline figure is worth in an ordinary year.
Are there caps, clawbacks or windfall clauses in the plan?
Why ask it
Windfall language lets the company reduce the payout on an unusually large deal, and it tends to sit deep in the plan document. Ask to read the full plan before accepting. Rules on recovering commission already paid differ by country and state, so ask how it works where you would be employed.
What am I paid while I ramp: a recoverable draw, a non-recoverable one, or base only?
Why ask it
A recoverable draw is an advance you repay out of later commission, and a non-recoverable one is simply pay. The difference decides what your first two quarters are worth, so ask for the term to be written into the offer.
For this seat, what is the split between new business, expansion and renewals?
Why ask it
Winning new customers, growing existing ones and renewing contracts make for three different working weeks. Ask what share of the quota each carries, and whether renewals count toward your number or are simply expected on top of it.
Besides bookings, what are sellers measured on?
Why ask it
Activity minimums, pipeline coverage and forecast accuracy count in reviews at some companies and are ignored at others. Ask which of them has ever cost someone a bonus or a job. That separates the metrics that matter from the ones that only sit on a dashboard.
Pipeline and deals
Who is your best-fit customer, and what kind of deal do you tell reps to walk away from?
Why ask it
A clear answer names a company size, a buyer's job title and the problem that makes them take the call. The walk-away half matters as much, because a team allowed to chase anything tends to carry a pipeline full of deals that never close, and you would inherit the habit.
Where does pipeline actually come from: marketing, outbound, partners, or the existing base?
Why ask it
The mix determines what the job really is. If most sourced pipeline is expected to come from the rep, you are being hired to prospect regardless of what the title says.
How do you carve up territories and named accounts, and when was the last redraw?
Why ask it
Territory design tends to end up on the VP's desk, which makes this the person to ask for the logic: geography, industry, company size or seniority. Ask what happened to deals in flight at the last redraw, because a rep who loses an account mid-cycle can lose the commission with it.
What would I inherit on day one: named accounts, open opportunities, or a blank patch?
Why ask it
An inherited pipeline can be a gift or a pile of deals the last rep could not close. Ask how old the open opportunities are and whether you would be paid in full on any that close during ramp.
What is the average sales cycle, and what usually stalls a deal near the end?
Why ask it
The stall answer is the more revealing half: procurement, security review, a missing economic buyer, or no real urgency. A leader who can name the usual one has been sitting in the deal reviews, and you can ask what the team now does earlier in the cycle because of it.
What is the typical deal size, and how wide is the range?
Why ask it
An average hides the spread. A team that lives on a handful of very large contracts has lumpy quarters, and a new seller without one of those accounts can do everything right and still miss.
Who else on the customer side has to say yes, and where do reps here usually miss someone?
Why ask it
A team that knows its buying committee can name the function that gets skipped: legal, security, finance. That is where deals die late, and it is the first thing to learn about in your opening month.
What is the win rate on qualified opportunities, and which competitor takes the most deals from you?
Why ask it
Set the win rate beside quota and deal size to work out how many opportunities you would need in a year. On the competitor, listen for a specific reason: price, a missing feature, arriving late to the deal. That reason is the objection you will be handling by your second month.
Why do customers buy from you instead of doing nothing?
Why ask it
In many markets the real rival is the status quo, and a VP who knows it will talk about urgency and the cost of waiting instead of feature lists. If every example is a win against a named competitor, ask how many qualified deals end with no decision at all.
How much discounting is normal, and who approves it?
Why ask it
Habitual deep discounts point to a pricing or positioning problem the sales team is absorbing. The approval path also tells you how much of your time would go on internal sign-offs instead of selling.
Which sales methodology or qualification framework does the team run, and how strictly?
Why ask it
The brand name matters less than whether it is enforced. Where every rep's deals are held to the same stage definitions, a forecast call is about the customer. Where each rep qualifies in their own way, it turns into a contest of who argues best.
Who supports a deal besides the rep: SDRs, sales engineers, legal, a deal desk?
Why ask it
Ask for ratios, because one sales engineer shared across ten sellers is a queue. Then ask what happens to a deal when the shared person is booked, which is when you find out whether support is a resource or a bottleneck.
How do you and marketing handle disagreement about lead quality?
Why ask it
Most sales and marketing teams have this argument, so the useful part is whether there is a shared definition of a qualified lead and a regular meeting where it gets settled. Without those, expect to spend part of each quarter disputing where a deal came from.
What happens to an account after it closes: who owns it, and who is paid when it grows?
Why ask it
The handoff to customer success or account management decides whether your best customers stay yours. If expansion is credited to someone else, the first contract is the only time you earn on that logo, and you should judge the quota with that in mind.
How they lead
How long have you led sales here, and what was the first thing you changed?
Why ask it
A new sales leader usually brings a new plan, redrawn territories and sometimes their own people. Someone a few months in is still deciding who stays, which can be an opening for a new hire or a risk, and their first change shows what they thought was broken.
Why did you join this company, and has it turned out the way you expected?
Why ask it
You are borrowing their due diligence. Whatever persuaded an experienced sales leader to sign on, the product, the founders, the equity, can be checked, and the second half invites the gap between the pitch they heard and what they found.
How would your managers and reps describe your leadership style, in a good quarter and in a bad one?
Why ask it
Style shows at the end of a hard quarter, which is why the second half is there. A VP who admits to going quiet, or to climbing into every deal, has given you something more useful than a description of their best days.
Walk me through your forecast process week to week.
Why ask it
Listen for what a rep has to bring and on which day: a commit number, a best case, the deals behind each. Then ask how close the team's forecast came last quarter, because a leader whose own call keeps missing tends to pass that scrutiny down.
What does coaching look like here: call reviews, deal reviews, ride-alongs, and how often?
Why ask it
At VP level most coaching is done by the managers, so the useful part is whether they know how their managers go about it. Ask when they last listened to a rep's call themselves. A leader who cannot say is describing inspection, not coaching.
How many layers sit between you and this seat, and how often would we actually work together?
Why ask it
With a director and a manager in between, the VP sets the weather and your manager is the job. If that is the structure, ask to meet the manager before you accept, if you have not already.
When do you get involved in a deal yourself, and what does a rep have to do to get you into one?
Why ask it
Executive presence helps close large deals, so the VP's calendar is a resource like any other. Find out whether it goes to the biggest opportunities, the loudest reps or by some rule, and whether they take over the meeting once they are in it.
Have you ever pushed back on the number you were handed, and what happened?
Why ask it
A VP of Sales stands between the board's target and the team's capacity. Whether they have argued a number down, and what it cost them, tells you if quotas here are negotiated with evidence or simply passed along.
How have you handled a top producer who broke the rules, on discounting, account ownership or how they treated colleagues?
Why ask it
Most sales teams have had this case. If the honest answer is that results buy exemptions, then the rules of engagement being described to you apply only to people below a certain number.
What would you want from me by thirty, sixty and ninety days?
Why ask it
Sales leaders tend to have concrete answers here: fluent in the pitch by the first mark, a set amount of pipeline by the second, a first close or a late-stage deal by the third. Write the milestones down. They are what you will be judged on during ramp, whether or not anyone mentions them again.
What would make you decide in someone's first six months that it was not working?
Why ask it
Sharper than asking what success looks like, because it forces observable behavior: activity levels, pipeline built, a first close. It also tells you how quickly this org cuts people.
When someone past ramp falls behind plan, how long do they get, and what help comes before a performance plan?
Why ask it
Listen for the sequence: closer pipeline reviews, a change of accounts, then something formal. A leader who goes straight to the exit has told you how much patience the company has for a bad year, and everyone has one eventually.
If I would be managing reps for you, how much say would I have over hiring, territories and their quotas?
Why ask it
For a manager or director seat, this defines the job. Owning a team number without any authority over who is on the team or how the accounts are split is the hardest version of it, so ask for a recent example of a manager's call that stood.
For a manager's seat: would I be expected to close deals of my own, or only to run the team?
Why ask it
A player-coach role splits the week between closing and coaching, and at quarter end closing usually wins. Ask how the last person in the seat divided their time and whether the VP thinks it worked.
Team and next steps
Who is your strongest seller, and what do they do differently from the rest?
Why ask it
The answer shows what behavior is actually rewarded, and whether success here is repeatable or personal. If the top performer wins purely on inherited accounts, the model is not transferable to you.
How much turnover has the team had in the past year, and why did people leave?
Why ask it
Ask for the count, then the reasons. Attrition concentrated in one segment or under one manager is a specific problem, and a leader who attributes all of it to fit is not looking closely.
Is this seat new, or am I replacing someone, and where did they go?
Why ask it
A new seat means untested territory and no baseline for the quota. A replaced one comes with a story: promoted, gone to a competitor, or managed out. Each says something different about the patch and about the plan.
How are new sellers onboarded: is there a schedule, a certification, someone assigned to me?
Why ask it
Look for names and dates: product training, calls to shadow, a pitch sign-off, a first pipeline review. 'You'll sit with a few people' means part of your ramp will go on finding out where things are kept.
What tools does a seller here actually live in, and how much of the day goes into the CRM?
Why ask it
Ask for hours, not product names. Every hour spent updating fields is an hour away from customers, and a VP who has never asked the reps for that figure is unlikely to be working on bringing it down.
How would you describe the sales culture here: leaderboards and contests, or pooled targets and shared deals?
Why ask it
Some floors run on public rankings and some on team numbers, and people who thrive on one often dislike the other. Ask how the last split-credit argument between two reps was settled, because that is where a culture shows how it handles money.
Where do good sellers go from this seat: a bigger segment, management, or another company?
Why ask it
Ask for names: the last two people promoted out of this seat, and how long each had been in it. If strong reps mostly leave to get the next title, the career path exists on a slide and nowhere else.
How much of the job is travel, office time and customer sites?
Why ask it
Field, inside and hybrid roles are different jobs with different costs. Ask what the people at the top of the board actually do, since the written policy and the habits of those who make quota are not always the same.
A year in, what would you want the person in this seat to be known for?
Why ask it
The answer separates a leader with a plan for the role from one filling a gap in a headcount plan. Vague answers about being a team player usually mean the seat's purpose has not been decided.
Knowing the plan as you do, would you take this seat yourself?
Why ask it
Asked lightly, this gets a more personal answer than anything about culture. A VP who came up as a rep will often say which segment or territory they would choose, and it is worth hearing that before an offer names yours.
Is there anything in my background that makes you doubt I could carry this number?
Why ask it
Sales leaders expect to be asked for the objection. Hearing it in the room lets you answer it there, and the way you handle it is a small sample of how you would handle a hesitant buyer.
Could I speak with one or two reps on the team before I decide?
Why ask it
The request is ordinary at this stage, and a confident leader agrees without steering you to one favorite. Put the same ramp, attainment and comp questions to the rep and compare the two sets of answers.
What happens after this conversation, and who else has a say in the decision?
Why ask it
The VP is often the last round or close to it, so they can usually give you the timeline and say whether anyone after them can overrule the choice. If you have other offers moving, mention the dates here.
If you are hiring
Tell me about the last sales team you ran: how many reps on your first day, how many on your last, and how many of them did you hire yourself?
Why ask it
You are finding out which stage they have actually worked at. Someone who inherited eighty reps and a recruiting department has done a different job from someone who hired the first five, and only one of those may be the job you have open.
What deal sizes and sales cycles have you led teams through, and how do ours compare?
Why ask it
Running a floor of fast, low-priced sales and running a handful of year-long enterprise deals are different crafts, and experience in one does not always carry to the other. A prepared candidate already knows roughly what you charge and will say where their background fits and where it does not.
From what you have seen of us so far, what would you look into first, and what would you leave alone?
Why ask it
Someone who has done their homework will have a view from the outside, on your pricing page, your job ads or your reviews, and will say what they need to see before changing anything. Be careful with a complete plan from a person who has not yet asked you about the current numbers.
If you started next month, what would you expect the numbers to show two quarters later?
Why ask it
There is no correct figure. A careful candidate gives a range, says what it depends on (how long new reps take to ramp, how much pipeline exists today), and points out that more opportunities will show up before more revenue does. A single confident number, given before they have seen your pipeline, is a guess.
Who would your first two hires be, and do you already know them?
Why ask it
Leaders who have built teams before often have people who would follow them, and can describe them even if they will not name them yet. An honest 'I would recruit from scratch' is fine too, but it changes how long the build takes, so ask what their timeline assumes.
How would you set quotas and build a comp plan for a team at our stage?
Why ask it
Ask them to work an example with your real figures: average deal, current win rate, what a rep costs you. Watch the method more than the result. A candidate who asks what the business can afford to pay for new revenue before proposing a split is thinking about your company, not reciting their last plan.
How much selling would you do yourself in the first six months?
Why ask it
At a small company the first sales leader often has to close deals while hiring. At a larger one that gets in the managers' way. Either answer can be right, but it has to match what you need, and this is a mismatch that tends to surface a quarter too late.
When you gave your last company a forecast, how did you build it, and which way did it usually miss?
Why ask it
You will be repeating this person's number to your board or your bank. Ask what they do with a rep's most hopeful deal and how they treat a quarter that depends on one contract. A candidate who remembers how far out they were, and in which direction, has been keeping score.
Tell me about a year your team missed its number. When did you know, and who did you tell?
Why ask it
Anyone who has led sales for long has had one. The timing is the part to press on: a leader who saw it coming in the second quarter and said so gave the company time to react, and one who held the forecast until the last month did not. A candidate with no such year has not been in the seat long, or is leaving something out.
How do you want to work with marketing and customer success, and where has that gone wrong for you before?
Why ask it
Leads and renewals tend to get dropped at the handoffs on either side of sales. A specific story, a dispute over lead quality or a handover the customer noticed, and what was agreed afterwards, is more useful than a statement that alignment matters.
What would you need from me, and from product, to hit the plan?
Why ask it
Strong candidates set conditions: budget for hires, a say in pricing, a fixed hour with you each week. Hearing them now lets you find the disagreement before the offer instead of in month four, and a candidate who needs nothing has probably not pictured the job yet.
Which two people who reported to you should I call, and can one be someone who left your team?
Why ask it
References a candidate picks will be friendly, so ask for a category instead: a rep who missed quota under them, or one who resigned. Ask those people what a one-to-one with this person was like when a quarter was going badly. Rules on taking references differ by country, so check what applies where you are hiring.
Interviewing With a Sales Leader
Practical guidance for the conversation itself
Preparation That Changes the Conversation
Know what they sell and to whom before you arrive
Read the pricing page, the case studies, and two or three reviews written by customers. If you can name the segment, the rough price point and one competitor, you can ask specific questions instead of general ones, and a sales leader notices the difference immediately.
Bring your own numbers
Quota, attainment by year, average deal size, cycle length, ramp time, and the mix of inbound and self-sourced pipeline. A VP of Sales will ask, and having the figures ready earns you the standing to ask for theirs.
Choose by seat and by round
The groups are not an order to ask in. If the VP sits two levels above the role and the hiring manager has already covered quota and comp, spend the time on The plan, which only the VP can answer. For a rep seat with no earlier round, lead with The numbers and Pipeline and deals. For a manager or director seat, add How they lead, which ends with two questions about managing.
Ask for the numbers plainly
Quota attainment, turnover and ramp are ordinary questions in a sales interview, not impertinent ones. Ask them in a flat, factual tone and treat the answer as data. Hedging on those three tells you something too, so note it and put the same question to a rep on the team.
Verify outside the room
Ask to speak with a current rep on the team and, if you can, find a former one. Two consistent accounts of ramp, comp and management style are worth more than any answer given by the person who owns the number.
Do the Arithmetic Before You Accept
- 1Take the quota and divide it by the average deal size to get the number of closed deals you need in a year.
- 2Divide that by the win rate they quote to get the number of qualified opportunities required. Twenty deals at a win rate of one in four is eighty opportunities.
- 3Divide by twelve for the new opportunities you would need each month, and ask whether anyone on the team opens that many.
- 4Compare the sales cycle length with the ramp period. If the cycle is longer than the ramp, ask how first-year quota is prorated.
- 5Check what share of that pipeline the company provides. Anything you have to source yourself is time not spent closing.
- 6If any step in that chain does not hold together, raise it in the interview rather than after you sign.
Signals Worth Weighing
- A leader who quotes attainment, turnover and cycle length from memory is looking at the numbers every week. If they offer to send the figures later, ask when, and see whether they arrive.
- A VP who can state the year's priorities and the one thing outside sales the plan depends on has usually said both to the team already.
- A new comp plan each year is ordinary. A plan changed in the middle of a year, or accelerators removed after a strong quarter, deserves a follow-up question.
- A team where the top one or two reps carry most of the number may be a team where the average seat is struggling. Ask how the middle did.
- Vague ownership between sales and marketing on sourced pipeline tends to mean arguments at the end of every quarter.
- If every answer about missed targets points at another function, expect that pattern to continue once you are inside it.
- A leader who asks you hard questions about your own pipeline will probably ask them of you every week. Decide whether that is the kind of boss you want.
What Not to Do
- Do not open with base salary. Get the plan mechanics first, then negotiate once you know what the variable is actually worth.
- Do not work through the list. Pick six and follow up hard on the answers that surprise you.
- Do not criticize your last employer's leadership. A sales leader is listening for whether you own your numbers.
- Do not accept a percentage without a denominator. Sixty percent of a team of five is three people.
- Do not skip the turnover question because it feels awkward. A sales leader has been asked it before, and the answer is hard to get any other way before you sign.
If You Are the One Hiring
- The last group is for a founder, chief executive or board member interviewing a VP of Sales candidate. The rest of the page is useful to you as well: it is what a strong candidate will ask, so have your attainment, ramp and pipeline figures ready.
- Say which job you have. Building a first team, scaling one that works and repairing one that does not are different jobs, and a candidate can only tell you whether they have done yours if you name it.
- Give real numbers. Nobody can say anything useful about quotas, hiring or a forecast without your deal size, win rate and current pipeline, and a good candidate will ask for them.
- What an employer may ask a candidate, and how references can be taken, differs by country and state. Check how it works where you are hiring.