Questions to Ask a Sales Director in an Interview
These are questions to ask a sales director in an interview, written first for the candidate sitting across from one. The 75 questions open with the staples (quota and how many reps hit it, ramp, the biggest challenge, what success looks like), then work through pay and territory, leads and deals, how the director runs the team, and how to close. Two shorter groups cover the other things people mean by questions to ask a sales director: the ones for when you are interviewing for the director of sales job yourself, and the ones for a sales director candidate when you are the one hiring.
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The questions
Each question, and why to ask it
Role and pay
What is quota for this role, and what share of the team hit it last year?
Why ask it
Quota is the easy half to state. Attainment is the answer you came for, and a director who has to hunt for that percentage either does not track it or would rather not say. If fewer than half the team got there, ask whether the quota had just been raised or the team was new, because the figure alone will not tell you which.
What does ramp look like, and what would you expect from me in the first ninety days?
Why ask it
"Shadow some calls and read the docs" is a sign onboarding is improvised. A specific answer names a person, a certification or a number of discovery calls, which tells you someone owns your first quarter. Ask whether quota is reduced while you ramp, and for how long.
How is the sales team structured right now, and where would this role sit?
Why ask it
You want the count of reps, who they report to, and whether prospecting and account management are separate teams. Then ask when the structure last changed. If it has been redrawn twice in a year, quotas and territories are probably still moving, and it is fair to ask whether yours would be.
What is the biggest challenge the sales team is up against right now?
Why ask it
One named problem, such as a competitor's new pricing, a slow segment or too few leads, tells you where your first year would go. "Nothing major" from someone who is hiring is either politeness or a team that does not talk about its problems.
What does success in this role look like at six months and at a year?
Why ask it
Push for something you could check later: a revenue figure, a count of new customers, a pipeline of a stated size. If the six-month answer is full quota and the ramp they described is also six months, the two answers disagree, and it is fair to say so.
How long is the usual sales cycle, and how long does a new hire take to close a first deal?
Why ask it
The second half gets you the cycle as a newcomer lives it, without the warm accounts and old contacts that flatter the team average. If a first deal takes longer than the ramp period you were just told about, you would be carrying full quota before you could realistically have closed anything.
Why is this role open, and what happened with the person who had it before?
Why ask it
Growth, a promotion and a departure are three different stories. If it was a departure, ask what they would do differently for the next person in the seat. An answer that turns abstract at this point is worth a second, plainer ask.
How was this year's quota arrived at, and how much did it rise from last year's?
Why ask it
A number built from what the territory has produced before can be defended. One that comes from dividing the company target by headcount cannot, and a steep rise after a year when few people reached the old figure is the thing to ask about twice.
What does the compensation plan look like, and how many times has it changed in the last two years?
Why ask it
Get the split between base and variable first, then the history. A plan that is rewritten every few months is hard to budget a household on, so ask what prompted each change and whether reps saw it before it took effect. Ask when commission is paid too: on booking, on invoice or on cash collected can move your income by months.
What did the typical rep on this team earn last year against the on-target figure?
Why ask it
On-target earnings describe the plan on paper: what it pays if you land exactly on quota. What the middle rep banked is the plan as it ran. If the two are far apart in either direction, ask why before you rely on either one.
Is commission capped, and are there accelerators once I pass quota?
Why ask it
Accelerators say the company wants you still selling in the last month of a good year, and a cap says the opposite. Ask as well whether commission can be taken back if a customer cancels or does not pay. The summary you hear in an interview leaves out the clauses, so ask to read the plan document before you accept.
During ramp, do I get a draw or a guarantee on commission, and would I ever owe it back?
Why ask it
A recoverable draw is an advance on commission you have not earned yet, and a slow start can mean repaying it out of later paychecks. How draws and repayment work depends on the employer and on local employment rules, so ask how it works there and get the terms in writing.
How are territories or accounts split, and how often do they get reassigned?
Why ask it
By region, by industry, by company size or by a named list: each one is a different job. Where the lines are redrawn every year you may hand over accounts you spent months warming up, so ask what happens to deals that are already open when that happens.
What exactly would be mine on day one, and how did that book perform last year?
Why ask it
Get last year's closed revenue from that list and what sits open in it today. A book that produced a third of quota under its last owner will not triple because the name on it changed, and now is a cheaper time to hear that than your first review.
Leads and deals
Which matters more to this year's plan: winning new customers or growing the accounts you already have?
Why ask it
The answer says which kind of selling gets noticed this year. A plan that leans on new customers wants a hunter, and one that leans on existing accounts wants someone patient with renewals and add-ons. If you hear "both equally", ask which one the comp plan pays more for.
Where do most of your qualified leads come from today?
Why ask it
The split between inbound, outbound and partner-sourced tells you what the job actually is. A team that says inbound but has no marketing headcount is describing a hope, and you would be cold calling.
How do sales and marketing agree on what counts as a qualified lead?
Why ask it
Without a written definition, expect recurring arguments about lead quality and a pipeline that looks fuller than it is. Stated criteria and a named handoff step are signs the two teams talk to each other.
Is there a sales development team booking meetings, and how are those meetings shared out?
Why ask it
How booked meetings are handed out quietly decides who makes quota: round robin, by territory, or to whichever rep the booker likes working with. If nobody books meetings for the reps, ask how many hours a week they spend prospecting and plan on the same.
Do you follow a set sales process or methodology, and what are the stages a deal goes through?
Why ask it
Named stages, each with a test for moving a deal forward, mean your pipeline is judged by the same rules as everyone else's. If the team uses a methodology you have not worked with, say so and ask how new hires are taught it. "Everyone has their own style" can be real freedom, but then ask how two reps' deals are compared in one forecast.
What is a typical deal worth, and how many of them does a rep need to close in a year to make quota?
Why ask it
Divide the quota by the deal size and you have the job in one figure. Forty small deals a year is a volume job run on activity, four large ones is a patience job run on relationships, and people who thrive in one are often miserable in the other.
Who signs the contract on the customer's side, and who else can stop a deal?
Why ask it
The buyer's title tells you which conversations fill the week. A finance lead wants a business case, an operations manager wants to know nothing will break. If procurement or a security review turns up late in most deals, add those weeks to whatever sales cycle you were quoted.
Who do you usually compete against, and why do you lose the deals you lose?
Why ask it
"Price" on its own is the answer people give when nobody has gone back and asked the customer. A named competitor and a specific gap in the product come from someone who reviews lost deals, and that gap is the objection you would hear most.
When a customer picks you over the alternative, what reason do they give?
Why ask it
This is the pitch you would really be making. If you get a feature list, ask for the last customer who said it out loud. Someone who sits in on deals can quote one, and that sentence will serve you better than the slide deck.
Which feature request has cost you the most deals this year, and is it on the roadmap?
Why ask it
A named request with a date attached means sales has a voice with the product team. A shrug means you would sell around the same gap for as long as you stayed, which belongs in your own estimate of how reachable the quota is.
How does the team handle pricing approvals and discounting?
Why ask it
This is really a question about how much authority you would carry into a negotiation. If every discount needs the director and the finance team, deals slip at the end of the quarter and the delay lands on your number, not theirs.
When a deal gets technical or legal, who joins me, and how many reps share that person?
Why ask it
The ratio tells you how long a customer waits for a demo or a contract review, and a long wait gives them time to take a competitor's call. Ask how a rep books that help as well. A calendar link is a system, a favor asked in a chat channel is not.
After the contract is signed, does the account stay with me, and is any of my pay tied to renewal?
Why ask it
Handing every customer to an account manager keeps you hunting, which suits some sellers and bores others. If the account stays yours, ask how much of the week goes to servicing it, because that time comes out of prospecting and the quota rarely shrinks to match.
How they lead
How do you build your forecast, and how close has it been lately?
Why ask it
Someone who can set last quarter's call beside the actual result is running the team on evidence. If forecasting is described as gut feel, ask what happens to targets when the gut is wrong, because that is when goalposts move mid-quarter.
When you and a rep disagree about whether a deal will close, whose call goes into the forecast?
Why ask it
Where the director overrides every commit, reps stop forecasting and start repeating what the boss already decided. "The rep's call stands and we go through the misses together" describes a team where you can say a deal is dead without paying for it.
How do deal reviews work, and how involved are you in individual deals?
Why ask it
This separates coaching from surveillance. A weekly review of a handful of large deals is ordinary. Daily inspection of every opportunity points to low trust, or to a leader who has not let go of selling.
What does your coaching look like week to week, and how often do you join calls?
Why ask it
Listen for a cadence and a method: recorded calls gone through together, a one to one that is more than a pipeline audit. A leader who never hears your calls can only give feedback on the number.
How would you describe your leadership style, and what is it like in the last week of a quarter?
Why ask it
Everyone is a supportive coach in week two. Quarter end is when a director either clears obstacles or starts messaging about the same deal every hour, so ask about the most recent one and what they personally did in it.
Besides closed revenue, what do you look at to judge whether a rep is on track?
Why ask it
Pipeline coverage, meetings booked and movement between stages are fair early measures. A daily dial count for an experienced seller means effort is being managed because results arrive too slowly to manage, and you would feel that every morning.
What number are you personally responsible for this year, and how is it tracking?
Why ask it
How far ahead or behind that number sits explains the mood you would walk into. Ask whether it is the reps' quotas added together or something larger, since any gap between the two is pressure that reaches you. A leader well behind late in the year tends to hire in a hurry and manage in one too.
How long have you been director here, and who do you answer to?
Why ask it
Someone under a year in the seat is usually still changing things, so the comp plan, the territories and the process may not have finished moving. Whether they report to a VP of sales, a chief revenue officer or the founder tells you who really sets the number you would carry.
What do you like most about leading this team, and what would you change if you could?
Why ask it
The first half is the question every candidate asks, and it gets a warm, practiced answer. Listen harder to the half about change. A wish for more headcount, better leads or a simpler comp plan is a list of what this director has asked for and not been given.
What tools does the team use, and how much admin work do they create?
Why ask it
Ask what a rep is required to log after every call. Long stacks with overlapping tools tend to mean hours of data entry that never appears in the job description.
What does a typical week look like for a rep here, and how much of it is spent actually selling?
Why ask it
Count the standing meetings as they list them. If forecast calls, pipeline reviews and internal updates fill three mornings, the selling week is shorter than the quota assumes, and it is reasonable to ask which of those a rep can skip when a customer wants that slot.
Team and close
Who is performing best on the team right now, and what do they do differently?
Why ask it
A detailed answer about habits, such as how that rep prepares for a first call or which accounts they go after, means success here is understood well enough to be taught. "Attitude" or "hustle" means it is not, and you would be working it out alone.
What happens when someone misses two quarters in a row?
Why ask it
Every team has a real answer to this, and it is either a structured improvement plan or a quiet exit. Hearing the actual sequence tells you how much runway you would get if your first patch is a hard one.
How many people have left the team in the past twelve months, and how many of those departures were their choice?
Why ask it
Sales teams lose people, so the count alone says little. The split says more: mostly managed out points at hiring or ramp, mostly walked points at the plan or the leader. A long pause to count is part of the answer.
Who was the last person promoted off this team, and what did their path look like?
Why ask it
A name and a timeline show that internal moves really happen. If nobody comes to mind, advancement here probably happens by leaving, whatever the career framework says.
How would you describe the culture on the team: do reps compete with each other or share what works?
Why ask it
Neither kind of team is wrong. What matters is which one you sell better in. Ask whether results go up on a leaderboard, and what happens when two reps claim the same account: the rule for that dispute, or the lack of one, is the culture in practice.
How many days a week is the team in the office, and how much travel does the territory need?
Why ask it
Ask what the reps who make quota do, since their habits and the written policy can differ. If a field territory is described as occasional travel, pin it down to nights away per month before you take anyone's word for occasional.
Would you put me in touch with a rep who started in the last year?
Why ask it
An easy yes, with more than one name offered, is a good sign before you have spoken to anyone. Ask that rep how their first two commission statements compared with what they were told in this room.
If I joined and it did not work out, what would the most likely reason be?
Why ask it
Asked late, this gets an honest answer more often than you would expect, and it is usually the real risk in the job: a long cycle, a thin territory, a product gap. If the answer is that nothing could go wrong, you are being sold to.
What is your biggest reservation about hiring me for this role?
Why ask it
You are asking for the objection, and a sales director will notice you doing it, which is half the point. Answer it once and briefly, as you would with a buyer. Five minutes of arguing confirms whatever the doubt was.
What are the next steps from here, and who else will I meet before a decision?
Why ask it
Leave with dates. Anyone who sells for a living knows a deal with no next step is not a deal, so a vague answer here usually means the decision is not theirs alone or has not been made.
For the director job
What number would I own, and how did the team finish against it in each of the last four quarters?
Why ask it
A director inherits a trend along with a target. Four quarters show whether you are being hired to keep something going or to turn it around, and those are different jobs with different amounts of patience behind them.
Who would I inherit: how many reps and managers, how long have they been here, and who is carrying the number?
Why ask it
A team where two people bring in most of the revenue is fragile, and your first job would be keeping those two. Ask as well whether anyone on the team applied for this role, since you would be managing them from the first morning.
Which of these would I control and which would I only advise on: headcount, territories, quotas, the comp plan, discounting?
Why ask it
Being accountable for a number with no say over quotas or comp makes you a forecaster with a bigger title. Go through the list one item at a time, because "you'd have a lot of input" generally means finance or the chief executive decides.
Is this a player-coach job, with deals of my own to close, or purely leading the team?
Why ask it
Both are real jobs, but a director with a personal number tends to save their own quarter first and coach second. For a mix, ask what share of the week each half is meant to take and which one gives way when the quarter is tight.
What is my variable pay tied to: team bookings, margin, retention, or a company-wide figure?
Why ask it
Whatever the bonus hangs on is what you will be pushed to chase, so check it against the priority you were told about. A director paid on bookings and judged on churn has been handed an argument with customer success before day one.
Who builds the annual sales target, and would I be in the room before it is fixed?
Why ask it
A target handed down from a fundraising model and one built up from what the territories can carry may sit far apart, and the director is the person who explains the gap to the reps. Being in that room is also how you learn whether the plan assumes hires nobody has approved.
What budget and headcount are approved for this year, as opposed to planned?
Why ask it
Planned hires disappear when a quarter goes soft, and the target often stays where it was. Find out which roles have signed-off budget today and what happens to the number if the rest never arrive.
How many heads of sales has the company had in the last five years?
Why ask it
Several sales leaders in a short span suggests the trouble sits above the role: a product that is hard to sell, a target nobody could reach, or a brief that keeps changing. Ask what each one was brought in to fix and you will hear which.
How involved is the founder or chief executive in deals today, and how would that change once I start?
Why ask it
Where the founder still closes the largest accounts, the director's first real task is taking over those relationships without losing them. Ask which customers still phone the founder directly, and whether reps go around their manager to do the same.
How far can I trust what is in the CRM today, and who looks after it?
Why ask it
Your first forecast will be built on that data. If a stage means different things to different reps, or nobody owns sales operations, plan on spending your opening months cleaning the pipeline before you can say anything reliable about it.
Which other department does sales argue with most, and about what?
Why ask it
Every company has one, and an interviewer who names it quickly is being straight with you. Lead quality with marketing, roadmap promises with product and handoffs with customer success are the common three, and you would own the sales side of that argument within a month.
How long would I have before the team's results are judged as mine?
Why ask it
Deals that close in your first quarter were mostly started before you arrived, and so were the ones that fall through. Agree a date now for when the number becomes yours, and hold it against the sales cycle you were quoted. If the grace period is shorter than one cycle, you would be judged entirely on deals someone else started.
What should be visibly different about the sales team six months after I start?
Why ask it
Listen for whether they want different results or a different way of working, since six months is rarely long enough to show the first where deals take a long time to close. Settle the measure now and you have something to point to at your first review.
If you are hiring
What was your team's target in your last full year, and where did you finish against it?
Why ask it
Begin with the number, because a sales director who cannot state it without checking was not the one answerable for it. Then ask how many reps made up the result. Hitting plan on one person's enormous deal is a different record from most of the team getting there.
How do you spend a normal week: in deals, coaching, hiring, or reporting upward?
Why ask it
Set the answer beside what your own team needs. Six inexperienced reps need a coach who lives in call recordings, and a candidate whose best weeks go to closing the largest account in person will leave those reps to themselves.
A rep who was at quota last year is at half of it now. What do you do in the first two weeks?
Why ask it
Good answers start by finding out why: a redrawn territory, something at home, a lost champion at a big account. Candidates who go straight to a performance plan, or straight to a pep talk, are showing you the one tool they reach for.
How do you decide who to hire for a sales seat, and who was your last hiring mistake?
Why ask it
The process matters less than whether they can describe a miss and what they screen for now because of it. Anyone who has built a team has made a bad hire, so a candidate with none to report has hired very few people or is not being candid.
Walk me through how you forecast, and tell me about a quarter you called wrong.
Why ask it
This person's number will go to your chief executive or your board, so the method has to be more than adding up what the reps say. The wrong call is the useful half: note how early they raised the alarm and what they changed in the process afterwards.
Which numbers would you want on your desk every Monday, and what would each one make you do?
Why ask it
Any candidate can list pipeline coverage, win rate and cycle length. The second half separates people who read dashboards from people who act on them, so press for one week when a number moved and they changed something because of it.
How have you set quotas and territories before, and what did reps complain about?
Why ask it
Every design leaves somebody unhappy, so a candidate who recalls no complaints was not listening or was not the one who designed it. A good answer explains the trade they chose, such as even opportunity over rewarding tenure, and what they would do differently.
How do you keep a team selling through a bad quarter?
Why ask it
"Contests and recognition" is the stock reply to any question about motivation. Ask for one quarter that was going badly and what they did in its last three weeks. You are listening for whether the pressure on them was passed straight down to the reps or partly absorbed on the way.
Tell me about a rep you had to let go. How long did it take, and what would they say about how you handled it?
Why ask it
You hear their timeline for underperformance, which you can hold against your own patience, and whether people are treated decently on the way out. Expect the details to stay general, and do not press for a name or anything that would identify the person.
How much of the selling did you do yourself in your last role, and how much would you expect to do here?
Why ask it
Titles hide this. A director of sales at a small company may have closed most of the revenue personally, while one at a large company may not have run a deal in years. Neither is a flaw, but only one of them matches the job you have.
What would your first ninety days here look like?
Why ask it
The strongest plans spend the early weeks listening: sitting in on calls, reading lost deals, meeting customers. Be wary of a candidate who would replace the comp plan or the CRM before meeting the reps, and of a plan that mentions nothing particular to your company.
If you had our team and our product on Monday, where would you expect the first extra revenue to come from?
Why ask it
It tests preparation and humility together. A strong candidate has looked at your pricing, your customers and your competitors and offers a hypothesis with its conditions attached. A weaker one recites the plan that worked at their last company.
Why do you want to lead sales at this company in particular?
Why ask it
A sales leader sells the company to every recruit and every large customer, so what you hear is a sample of that pitch. If it is thin with you, it will be thin with your best prospect.
Who from your last team would follow you here, and who would not?
Why ask it
Reps following a leader to a new company is strong evidence of what that leader is like to work for, and being able to say plainly who would stay away, and why, shows they know their own weak side. Before anyone acts on the first half, ask what their agreement with the last employer allows.
Getting straight answers from a sales director
Practical guidance for the conversation itself
Before you go in
Find the group for your seat
The first four groups are for a candidate being interviewed by a sales director, and "Team and close" is where that conversation ends. "For the director job" is for someone interviewing to become the director of sales, usually in front of a chief executive, a founder or a VP. "If you are hiring" is for the other side of the table. Most of the first four groups also work in a director's interview, asked about the team you would inherit. And if no interview is involved, because the sales director is newly your boss or your boss's boss, "How they lead" is the group to take into a one-on-one: the forecast, deal reviews, coaching and what they watch besides closed revenue.
Find the numbers you can find yourself
Headcount on LinkedIn, recent funding, the pricing page, the review sites. Knowing roughly how many reps they have lets you sanity check what you are told about quota and pipeline, and keeps your question time for things only the director can tell you.
Decide your three must-knows
You will probably get ten minutes of question time, not forty. Pick the three answers that would actually change your decision, usually attainment, lead source and the comp plan, and ask those first.
Ask for numbers, not philosophies
"How do you think about coaching?" invites a speech. "How many calls did you sit in on last week?" produces a fact. Phrase questions so the answer has a number, a name or a date in it.
How to read the answers
- Quota with no attainment figure: either untracked or unflattering.
- Ramp shorter than the stated sales cycle: you are on the hook before you can close.
- Comp plan changed more than once in two years: ask what would stop it changing again after you sign.
- No named example of an internal promotion: advancement probably happens by leaving.
- Territories redrawn every year: ask what happens to the deals you have open when the lines move.
- Inbound-led claim with no marketing team: the job is outbound.
- A cap with no accelerators: the plan stops paying at the point you are selling best.
- Draw terms nobody can explain: read the plan document before you count on the money.
- For a director's seat, accountability for a number with no say over quotas or comp: the title is bigger than the job.
What goes wrong
Saving every hard question for the offer stage
Attainment, comp mechanics and why the role is open are fair to ask in a first conversation with the hiring manager. Leave them until the offer and you will be weighing the answers against a deadline, perhaps after dropping out of another process.
Accepting a story instead of a figure
"We are growing fast" is not an answer to how many reps hit quota. Ask again once, plainly, and note whether the second answer is more specific or just longer.
Only interviewing the director
Ask to speak with a rep who joined in the last year. They will tell you about the CRM admin, the discount approvals and the ramp in terms nobody in management uses.
If you are the one hiring
- Ask for the figure first and the story second: the target, the result, the size of the team.
- Follow each question about method with a time the method failed. The failure is where candidates differ.
- Keep questions about former reps general. Do not ask for names or personal details.
- Judge the answers on selling time and coaching time against what your team needs this year, not against an ideal director.
Follow-ups worth having ready
When an answer stays general
- 1Can you walk me through the last time that happened?
- 2What did that look like for the person it happened to?
- 3How would I know, three months in, that it was going the way you describe?
When the answer is a number
- 1Was that figure different a year ago, and why?
- 2Which part of it do you expect to change next year?
- 3Where would someone new most likely fall in that range?