Questions to Ask a Sales Manager
Questions to ask a sales manager when you are a rep on their team, or about to be. They cover what a good week looks like, how your quota was set, pipeline and forecast, discount authority and deal support, leads and territory, coaching, the comp plan, promotion and what a missed month means. Each has a note on what the answer tells you or what to ask next. Most belong in a first one to one or the ones that follow, and several also work at a final interview with the person you would report to.
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The questions
Each question, and why to ask it
Expectations
What does a good week look like for someone in my seat?
Why ask it
Managers describe this in either activity or outcomes, and the difference matters. Twelve discovery calls is something you control, three closed deals in a nine-month cycle is not, and you need to know which one you will be judged on in month two.
How was my quota set, and how many people on the team reached theirs last year?
Why ask it
A quota built from the territory's own history is an estimate you can plan against. One that is the company target divided by headcount is closer to a hope, and last year's attainment is how you tell the two apart. If most of the team missed, ask what has changed since.
What do your strongest reps do that the middle of the team does not?
Why ask it
Wait for a habit you could copy on Monday: how they prepare for a first call, how fast they follow up, how early they bring in a second contact. If the answer is talent or hunger, ask whose calls you can listen to and work it out from the recordings.
How do you run one to ones, and what should I bring?
Why ask it
Some managers want your three riskiest deals and one thing you are stuck on, and others open the CRM and scroll. If it turns out to be a pipeline walk every time, ask where the coaching happens instead, because it will not be in that half hour.
What do you want me to have done by day 30, 60 and 90?
Why ask it
Three checkpoints are easier to hit than one instruction to get up to speed. Ask which of them involve revenue and which are about learning, such as running a demo unaided, so that a first month without a closed deal is not read as a slow start.
What are the two mistakes new people on this team make most?
Why ask it
The same slips happen to hire after hire, so the answer usually comes quickly, and it is specific to the product: skipping technical validation, promising a delivery date, going too wide on discovery. Ask which one last cost somebody a deal.
How do you want to hear about my deals, and how often?
Why ask it
Agree this early and you head off a familiar friction: a manager who feels they are chasing updates and a rep who feels watched. Ask for the format too, because a CRM field and a Monday summary are very different amounts of work.
Which activity numbers do you watch closely, and which do you ignore?
Why ask it
Every dashboard has more columns than anyone reads. Learn which two or three this manager opens on a Monday and you know where a quiet week gets noticed first. The ones they wave away are fields you can stop polishing.
How much of my week will go on internal meetings and reporting?
Why ask it
Add up what they list, then compare it with the activity expectations from earlier in the conversation. If the two do not fit into five days, one of them is going to give, usually the selling.
How quickly do you expect a reply from me outside working hours?
Why ask it
The last week of a quarter changes the answer on most teams, so ask about that week separately. Agreeing it now is easier than finding out on a Saturday that your silence was being counted.
What is your own boss pressing you on at the moment, and can I help with any of it?
Why ask it
Forecast accuracy, a new product that is not selling, clean CRM data before a board meeting: whatever it is, it explains requests that otherwise look arbitrary. Offer one concrete thing, such as having your close dates right by Thursday, and leave it there. You are asking for context, not volunteering for their job.
What is changing for the team in the next six months?
Why ask it
Pricing, a product launch, new headcount and a reorganisation all reach your manager before they reach you. They may not be free to say everything, but a partial answer can still stop you quoting a price that is about to move or building a plan around accounts that are about to be reassigned.
Deals
How much can I discount before I need to come to you?
Why ask it
A clear number means you can negotiate in the room. If the answer is always check with me, expect deals to stall at the end of the quarter through no fault of your own, and plan your close dates accordingly.
Which terms can I not change without legal or finance: payment dates, contract length, liability?
Why ask it
Price is only one of the levers a buyer pulls. Knowing which clauses are fixed lets you say no in the meeting instead of promising to check, and knowing who signs off the rest tells you how many days to add to a close date.
When you look at my pipeline and say a deal is not real, what are you looking at?
Why ask it
This is your manager's own qualification standard, and it is often stricter than the stages in the CRM. Get it stated: a named economic buyer, a next step with a date, a requirement the customer wrote down. Then you can clear out your own pipeline before they do it for you.
How much open pipeline do you expect me to hold against my number?
Why ask it
The usual reply is a multiple of quota, and the multiple only makes sense next to the team's win rate. If you are asked for three times the target while one deal in five closes, the sums do not meet, and it is better to say so now than on a forecast call.
When I call a deal 'commit', what are you assuming I have checked?
Why ask it
Forecast categories mean different things on different teams, and the argument usually starts when a committed deal slips. Get the list: an approved budget, a date the buyer gave you, paper already with their legal team. Then use the word only when the list is true.
What is the team's target this quarter, and where are we against it today?
Why ask it
Knowing the gap tells you which of your deals your manager is quietly counting on. Ask them to name those deals, then agree what help each one needs. That is a better use of the last month of a quarter than daily updates on all of them.
How do you decide when to step into a deal, and what do you do once you are in?
Why ask it
Some managers coach you before the call and stay off it, and some take the call themselves. The second kind may well win the deal, but afterwards the buyer rings them and not you. Agree a signal for when you want them in, so that it is your decision as often as theirs.
Who else can I bring into a deal, and how far ahead do I need to ask?
Why ask it
Sales engineers, legal and senior sponsors are shared, and the reps who get them are the ones who know the booking rules. Find out what your manager needs to see before lending their own name to a meeting. An executive call spent on a half-qualified deal is hard to get a second time.
Which steps of the sales process do you want followed exactly, and where can I use my own judgment?
Why ask it
The written process and the one people follow are often not the same. Your manager can tell you which steps get checked, say a discovery template or a demo that only a sales engineer may run, and which are suggestions. If the team uses a named qualification method, ask for a filled-in example from a deal that was won.
What kind of deal would you rather I walked away from?
Why ask it
Permission to disqualify is worth having before you need it. A manager who can name the bad fits, too small, the wrong industry, a buyer who only wants a quote to beat down their current supplier, will back you when you drop one. A manager who says chase everything will also expect you to forecast everything.
Which objection are customers raising most at the moment, and how do you want it answered?
Why ask it
Objections move with the market: a price rise, a competitor's launch or a bad review can put the same sentence in every buyer's mouth for a quarter. Your manager hears it from the whole team and may already have a reply that works. If they do not, offer to try two versions on your next calls and report back.
Which competitor do we lose to most, and what has worked against them?
Why ask it
The second half is the part to write down. Somebody on the team has already found the reference customer, the comparison or the question that turns those deals, and your manager knows who. Ask to be sent the notes from the last deal won against that competitor.
Leads and territory
Which accounts or territory would be mine, and how did they perform last year?
Why ask it
Inherited patches carry history: burnt contacts, a churned logo, a competitor already installed. Knowing that before you set expectations stops you from being measured against a predecessor's best year.
Which customers are the best fit for us, and how do I spot one early?
Why ask it
A good answer is narrow: a size, an industry, a job title, a problem the buyer already knows they have. Ask what the last three quick wins had in common, and let that decide which accounts on your list get the first calls.
How much of my pipeline am I expected to source myself?
Why ask it
Put a percentage on it, then ask what the people at the top of the board actually do. If marketing is meant to supply half and the best reps prospect for nearly everything they close, the official split is not the one to plan your week around.
How does the team handle leads that come through unqualified?
Why ask it
Ask what a rep does with a lead that should never have been passed on: reject it in the CRM, send it back to whoever booked it, or leave it sitting there. Where there is no route back, the bad leads end up in your conversion rate, so it is worth asking for one.
When two reps want the same inbound opportunity, how is that decided?
Why ask it
Either there is a rule, by territory, by named account or by turn, or it goes to whoever claims it first. Ask where the rule is written down. If it is not, ask how the last clash was settled, because that is the rule in practice.
Are there accounts in my patch where you or someone senior already has a relationship?
Why ask it
An existing relationship can open a door, or it can mean you are expected to stay out of the way. Ask for an introduction where it helps, and for a plain statement of who leads the account where it does not.
If my territory or account list changes mid-year, what happens to my quota and my open deals?
Why ask it
Redraws happen, and the rule for them is rarely written down until someone complains. You are asking two things: whether the target moves with the accounts, and how long you keep credit for a deal you opened in a patch that is no longer yours.
After the signature, who owns the customer, and does expansion count toward my number?
Why ask it
On some teams the rep keeps the account, and on others it passes to an account manager the day the contract lands. If you hand over, ask how the handover is done. A customer who has to explain themselves twice tends to ring the person who sold to them.
Coaching
How do you prefer to give feedback, in the moment or in a scheduled review?
Why ask it
In-the-moment managers can feel relentless if you are not expecting it, and review-only managers can let a problem run for months. Saying which you handle better usually gets the cadence adjusted.
Would you listen to one of my calls this week and tell me where the buyer lost interest?
Why ask it
Pick the call yourself, and choose one that went badly. A specific request with a recording attached is much harder to put off than a general wish for more coaching, and the minute they point to is usually earlier in the call than you expect.
If you could change one thing about how I sell, what would it be?
Why ask it
Save this until they have seen you on a few calls, which for a new rep means month two. One thing is the point of the question: a manager asked for general feedback gives a list, and a list rarely changes what you do on the next call.
Am I where you expected me to be by now?
Why ask it
Asked between reviews, this brings out the small doubts before they harden into a rating. If the answer is yes, ask what they would like you to keep doing, so you know what earned it. If there is a pause first, ask which number or habit is behind the pause, and take that one thing away to work on.
Who on the team should I shadow, and for what?
Why ask it
The 'for what' stops you being sent to the top earner by default. The best person at discovery, the best negotiator and the one with the cleanest follow-up are often three different people, and an hour with each teaches more than a day with one.
From where you sit, what makes a rep easy to manage?
Why ask it
It sounds like flattery and is really a request for their irritations in reverse. Whatever comes first, notes in the CRM before the meeting, a forecast that does not move on Thursday night, questions saved for the one to one, is the cheapest goodwill you can earn.
When I think you are wrong about one of my deals, how do you want me to say so?
Why ask it
You will disagree eventually, most likely about a close date or a discount. Some managers want it argued in the deal review with the evidence on screen, and others want it privately afterwards. Getting the etiquette right keeps the disagreement about the deal and not about you.
What is the most useful thing a manager ever did for you as a rep?
Why ask it
You get a story, perhaps a manager who sat through a lost deal with them or one who fought for an exception, and it is usually the kind of manager they are trying to be. Remember it. When you need that sort of help yourself, you can ask for it in their own words.
What made you move from selling into managing, and what do you miss?
Why ask it
One to ask if you think you might want their job one day. Listen for what the trade was for them: how their pay changed, how many more meetings there were, whether watching someone else close is enough. A manager who badly misses selling is often the one who takes over your calls.
Pay and promotion
Can we walk through my comp plan using a real deal as the example?
Why ask it
Plan documents are written in percentages and clauses, and they only become clear when a number goes through them. Bring a deal you expect to close and follow it from signature to payslip: the rate, the date it pays, and anything that could reduce it.
Is my quota reduced while I am new, and when does the full number start?
Why ask it
Ramps differ a great deal from one employer to the next: a few months at a lower target, a draw against commission that may or may not have to be repaid, or nothing at all. Ask for the month-by-month figures in writing and set them against the length of a normal sales cycle. If deals take six months to close and the full quota starts in month four, say so now.
What changes for me once I pass a hundred percent of quota?
Why ask it
Accelerators raise the rate above target and a cap stops it, and either one changes what an extra deal late in the period is worth to you. Ask also whether a big year pushes next year's quota up, which is often the price of one.
What happens to my commission if a customer cancels, pays late or the deal is split with another rep?
Why ask it
These three cases are where pay disputes tend to start, and each should have a rule somewhere in the plan. Have your manager show you the clause instead of summarising it. Clawback windows and what you are owed after leaving differ by employer and by local law, so ask how it works where you are.
Is there anything the plan pays extra for this quarter?
Why ask it
Bonuses for a new product, a multi-year contract or a first-time customer come and go, and they are announced in meetings that are easy to half-hear. They also show what the company wants sold right now, which is worth knowing even when the extra money is small.
When will I get next year's number, and can I comment before it is final?
Why ask it
A quota that arrives in the second month of the year has already cost you weeks of planning. The second half matters more: some managers take a rep's view of the patch into the room where targets are set, and they need it from you well before the number is fixed.
What would you need to see from me to support a promotion or a raise?
Why ask it
Ask for the evidence, not the qualities. A manager who can name the numbers, the scope and a rough timeline has probably put someone forward before. If all you hear is consistent performance, ask who makes the decision and what they were shown the last time it went through.
Who from this team has moved into a bigger role, and how long did it take them?
Why ask it
You are after the route as it has actually been walked, not the one in the handbook. Ask what each person did on top of their number, whether that was training new hires or taking the awkward accounts, and whether your manager argued for them or only signed the form.
What would you like me to take on beyond my own number?
Why ask it
Running a product session, mentoring a new hire or testing a new pitch are things a manager can cite when your name comes up for a senior seat. Agree what you would drop to make room, though, because the quota does not shrink to fit.
Is there a training budget or time set aside for it, and how do reps get it?
Why ask it
Where a budget exists it can go unspent simply because nobody asks. Come with one specific request tied to a gap your manager has already named, which is far easier to approve than a general interest in development.
When things go wrong
What do you want to know early, even when it is bad news?
Why ask it
Expect a short list of things they hate to hear late: a deal slipping into next quarter, a champion leaving, a customer's lawyers getting involved. Get the list, then use it. Bad news delivered early is a problem you are both working on, and delivered late it is something you kept from them.
What happens when a customer escalates over my head?
Why ask it
What you need to find out is whether you are brought back in once it is settled or the account quietly becomes theirs. Ask to sit in on the escalation call even if you say nothing, so the customer still sees you as the person who looks after them.
When I am behind, what do you want me to do first?
Why ask it
Some managers want more activity, some want the pipeline cut down to the deals that can still close, and some want you to ask for help on one account. Knowing their instinct in advance means your recovery plan looks like sense to them and not like panic.
What happens if I miss a month, and what if I miss a quarter?
Why ask it
Teams tend to have a sequence for this that nobody has written down: closer coaching, then a formal plan, then a conversation about fit. Hearing it plainly tells you how much room one slow month really leaves. What a formal plan involves depends on the employer and on employment law where you work, so ask to see the policy.
Who else sees my numbers, and how are they discussed?
Why ask it
There is a real difference between a private conversation with your manager and a leaderboard read out weekly to the whole company. Neither is wrong, but one of them changes how a slow month feels.
How do you handle it when a rep is having a hard time outside work?
Why ask it
You are not asking for anything, only finding out whether you could. Listen for a real example handled discreetly, with targets or accounts adjusted for a while. What leave or adjustments you are entitled to depends on the employer and on the law where you work, so check the policy as well as the manager.
If this was not working out, how and when would I hear it from you?
Why ask it
This is easier to ask in a good month than a bad one. You are finding out whether concerns get raised in the next one to one or saved for a review. If the reply is that it would never come to that, ask how the last person who struggled on the team found out.
Working with the manager you report to
Practical guidance for the conversation itself
How to run the conversation
Spread them over the first quarter
This list is a quarter's worth of one to ones, not one agenda. Take Expectations in your first week, Deals and Leads and territory as soon as you have live opportunities, and the pay questions before you sign the plan. Coaching lands better once your manager has watched you sell, and the promotion questions can wait until you have a quarter of results behind you.
Frame it as setting up, not testing
Opening with 'I want to get our working rhythm right in the first month' invites cooperation. The same questions delivered as an audit invite defensiveness, especially the ones about missed months and escalations.
Get the numbers written down
Discount authority, activity expectations and update cadence are the three that drift. Send a short summary afterwards of what you heard. It gives your manager the chance to correct you now, and it gives you both something to go back to in month four if memories differ.
Ask twice about the bad scenarios
Questions about missing quota or being cut out of an escalation usually get a soft first answer. Following up with 'what did that look like the last time it happened?' moves the discussion to something real.
Which questions for which moment
- First week: the Expectations group, plus discount authority and what makes a deal real to this manager.
- A regular one to one: one question from Coaching, asked about a particular call or deal and not in general.
- Before you sign the comp plan: the pay questions under Pay and promotion, with the plan document open in front of you both.
- A new or redrawn territory: the Leads and territory group, starting with how the patch performed last year.
- After a missed month: what they want you to do first, then which of your deals they would still bet on.
- Review time: the promotion question, who has moved up from this team, and what to take on beyond your number.
- Still interviewing: a good week, quota attainment, one to ones and what follows a missed quarter are all fair to ask the manager you would report to.
What the answers tell you
- No discount authority at all: your close dates depend on someone else's calendar.
- One to ones that are only pipeline reviews: coaching will not happen unless you ask for it separately.
- No rule for routing inbound: expect arguments about ownership.
- Activity expectations plus meeting load exceeding a working week: something is being quietly dropped.
- Promotion criteria described only as qualities: ask who decides and what they were shown last time.
- Inherited territory with no history offered: ask directly what churned and why.
- Quota explained as the company target shared out by headcount: ask how many of the team reached it last year.
- A full quota that starts before a normal sales cycle could finish: raise it before you sign the plan.
- A commit that means whatever the rep feels good about: agree your own checklist with the manager and stick to it.
- A comp plan described from memory: ask to read the clauses on cancellations, late payment and splits.
- No example of anyone moving up: ask what your manager would do in your position.
Common mistakes
Waiting until there is a problem
Escalation routes and discount limits are cheap to agree in week one and expensive to negotiate mid-deal. Ask while nothing is at stake.
Agreeing to a cadence you will not keep
If daily updates are unrealistic for how you work, say so now and propose an alternative. Silently missing an agreed rhythm reads as avoidance.
Skipping the peer check
Ask a rep on the team how the manager behaves in a bad quarter. That is the version of them you will be working with when it matters.
Raising pay only when a payslip is wrong
Walk a deal through the comp plan while nothing is in dispute. The same questions asked after a short payment sound like an accusation, and the answers get defensive.