10 Questions to Ask Your Sales Team
These are good questions to ask your sales team in a pipeline review, a weekly one on one or the meeting after a rough month, written for sales managers and for founders who still run the team themselves. The page goes well past the ten in its title: 50 questions in the order a review tends to run, from the pipeline to single deals, then customers, process and coaching, with a last group for a manager meeting a new sales team for the first time. Short of time? Open with the first three, then use the ten the guide underneath picks out.
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The questions
Each question, and why to ask it
Pipeline
What are you most excited about in your pipeline right now?
Why ask it
Starting with the deal a rep is proudest of gets them talking without the defensiveness a forecast question triggers. It also shows you what they consider a good deal, which is often a narrower or looser definition than yours.
Where is your pipeline thinnest right now: this month, next quarter, or the top of the funnel?
Why ask it
Giving three time horizons stops the reflexive answer that everything is fine and forces a choice. A rep who is fine this month but empty at the top of the funnel needs a completely different intervention than one scrambling to close.
Do you believe your number this quarter, and what has to be true for you to hit it?
Why ask it
Asking for the conditions rather than the commitment gives a rep permission to be honest without declaring failure. The list of things that must be true is also the most accurate risk register you will get all quarter.
If you had to take three deals out of your forecast today, which would go?
Why ask it
A ranking is gentler than being asked which deals are weak, and the rep nearly always knows the three at once. The follow-up is what would have to happen by Friday for each one to earn its place back.
Which deals have been stuck in the same stage longer than they should be?
Why ask it
Age in stage is the plainest warning the CRM offers, and reps rarely sort by it. For each deal named, get the date of the last conversation with the customer. With no recent contact it is a record, not an opportunity.
Think of a deal you called committed that slipped. What did you miss at the time?
Why ask it
Reviewing a specific past miss builds forecasting judgment far better than a lecture on stage definitions. A rep who cannot identify anything they missed will repeat it, which tells you where to coach next.
Which prospecting activity is producing meetings right now, and which one has gone dead?
Why ask it
Sequences, events, and referral paths decay quietly, and the rep working them daily notices weeks before the reporting does. Find out how much of the week the dead one still takes, because the habit tends to outlast the results.
How much of your pipeline did you find yourself, and how much was handed to you?
Why ask it
A rep living on inbound leads and inherited accounts can look healthy until the lead flow dips. The split tells you whether a thin quarter is a prospecting problem or a marketing one, and it lands better as a question about sources than as a verdict on effort.
Deals
Which deal are you most worried about, and what specifically worries you?
Why ask it
Reps almost always know which deal is rotting before it shows up in the CRM. Forcing the second half of the question stops the answer at a vague bad feeling and gets you the actual risk you can work on.
On your largest open deal, who actually signs, and have you spoken with them yourself?
Why ask it
This separates a real deal from an enthusiastic conversation with someone who cannot buy. A rep who has never met the signer is forecasting on hope, no matter how strong the champion sounds.
Who at the customer could still say no to the deal you are surest of, and what do they care about?
Why ask it
Finance, IT, legal and the person whose current tool would be replaced can each stop a purchase without ever joining a call. If the rep can name them but not their concerns, the next task is a conversation with one of them, not another demo for the champion.
What is the next step on the deal closest to closing, and has the customer agreed to it?
Why ask it
A next step that exists only on the seller's side is a plan to send an email. Listen for a date, a named person and something the customer has said they will do, such as bringing their security lead to the next call.
Why would your biggest prospect buy now instead of six months from now?
Why ask it
Deals do not usually die, they postpone, and the only defense is a dated business reason to act. If the answer is about your product rather than the customer's calendar, budget cycle, or deadline, expect the deal to slip.
Take a deal that has gone quiet: what happens to that customer if they do nothing?
Why ask it
Staying as they are is the option most buyers quietly prefer, and it has no salesperson arguing against it. When the rep cannot describe a cost of waiting in the customer's own terms, discovery is unfinished, however far along the stage field says the deal is.
What do we discount for most often, and would we still win those deals at list price?
Why ask it
Habitual discounting is often a symptom of weak value framing or late stage panic rather than real price sensitivity. Whether the deal survives at list is the part to press on, because it makes the rep say out loud what the concession actually bought.
At which stage are you losing the most deals, and what tends to happen right before you lose them?
Why ask it
Stage level loss patterns tell you whether to fix qualification, discovery, or closing, and each needs a different remedy. The event just before the loss, such as a legal review or a new stakeholder appearing, is often the real cause.
Which recent win could we repeat, and what made it close?
Why ask it
Teams pick apart every loss and wave the wins through, so the reasons for a win stay as folklore. Push past 'good relationship' to the event that moved it: a referral, a deadline on the customer's side, a trial with the right group of users.
What do you need from me this week to move one specific deal forward?
Why ask it
This converts a manager from an auditor into a resource and makes your involvement concrete rather than general encouragement. It also flushes out reps who have stopped asking because past requests went nowhere.
Customers
What did a customer say this week that stuck with you?
Why ask it
Your team hears market intelligence that never reaches a dashboard, and this question pulls it out as a story rather than a report. Repeated across the team, the same phrase usually points at a pricing, product, or positioning problem.
What is the most common objection you are hearing, and what do you say back?
Why ask it
The second half is the important part, because it tells you whether the team has a real answer or is improvising a different one each time. If four reps give four responses, you have a message problem, not a skill problem.
What question from a prospect do you find hardest to answer?
Why ask it
It tends to be a different one for each rep: the pricing logic for one, a technical limit for another, a reference customer in an industry you have not sold to. Collected across the team, the answers are the agenda for your next practice session.
Which competitor is showing up most in your deals, and what are they claiming about us?
Why ask it
Competitive claims travel through prospects long before they appear in a battlecard, and reps hear the live version. What a competitor asserts about you also reveals which of your weaknesses they think is easiest to exploit.
When a customer chooses us, what reason do they give in their own words?
Why ask it
The reason a buyer gives is often smaller and more practical than the one in the deck: a quick reply, a contract they could read, one feature. Those phrases belong in the next first call, and they cost nothing to collect.
What do customers keep asking for that we have to say no to?
Why ask it
One request is an anecdote, and the same request from several accounts is something product and leadership should hear from you. Check how the rep answers it today, too, because a casual 'that is on the roadmap' becomes a promise somebody else has to keep.
What are we promising in the pitch that the product does not quite deliver?
Why ask it
Reps discover the gap between the deck and the reality during implementation calls and renewal conversations. This is early warning on churn and on the deals your team is winning for the wrong reason.
Which of your existing accounts could be twice the size, and what is blocking that?
Why ask it
Growing an account you already hold usually takes less effort than landing a new one, and it tends to be neglected when the comp plan pays for new business. The blocker named here, whether a missing integration, a skeptical department, or a contract term, is often something you can remove yourself.
Process
Which step in our sales process do you skip or work around?
Why ask it
Every team quietly bypasses something, and whether the step is genuinely useless or genuinely being dodged is the whole question. Asking it as a neutral fact rather than a violation is what gets you a truthful answer.
How many hours a week go to work that is not selling, and what fills them?
Why ask it
Quotes, internal approvals, data entry and support questions that land on the rep because the customer knows their name all eat selling time. Nobody can hand those hours back until they are listed, and a rough guess made on the spot is enough to start with.
What does the CRM make you enter that nobody ever reads?
Why ask it
Fields get added after every bad quarter and are almost never taken away. Cutting two that feed no report buys goodwill for the ones you really need filled in, such as next step and close date.
Are the leads marketing sends you worth calling, and how quickly can you tell?
Why ask it
Reps size up a lead in seconds from the job title, the company or the form it came through, and that shortcut is exactly what marketing needs to hear. Bring back one good example and one bad one, since a complaint with no examples only starts an argument between departments.
Where do you wait on another department, and how long does it usually take?
Why ask it
Contract redlines, custom pricing, a security questionnaire, a technical person for a demo: each wait is time in which the customer's attention drifts. A manager can often shorten a queue that a rep can only stand in, but only once you know which queue.
Which piece of sales material do you actually send, and which have you stopped opening?
Why ask it
The case study that gets forwarded and the deck nobody uses show what buyers respond to in practice. The answer also spares whoever makes the material from producing more of the kind that sits untouched in a shared folder.
What goes wrong for a customer between signing and getting started?
Why ask it
The rep is the one who takes the annoyed call when onboarding stalls, so they know where the handoff drops things. Trouble here comes back months later as a difficult renewal or a referral that never arrives.
What should our team meeting stop covering?
Why ask it
A standing meeting collects agenda items the way a CRM collects fields. If several reps name the same segment, often a deal by deal readout that only two people care about, move it to one on ones and give the time back.
Does the comp plan push you toward the deals we actually want to win? Where does it not?
Why ask it
Compensation quietly overrides strategy, and reps can describe the exact deals the plan makes irrational to pursue. If you did not write the plan, say so, and carry their examples to whoever did.
Coaching
What one skill would make the biggest difference to your numbers, and how would you want to build it?
Why ask it
A rep is more likely to work on a gap they named than on one you assigned, and their pick is often not the one you would have chosen. How they want to build it tells you whether they need practice, examples, or you beside them on a call.
Which call this week would you like me to listen to with you?
Why ask it
Letting the rep choose the call makes the review feel like help instead of surveillance, and the choice itself is informative: a proud one, or the one that went sideways. Agree on a single thing to listen for before you press play.
Who on this team does something on calls that you would like to copy, and what exactly do they do?
Why ask it
Reps often pick up more from a peer's habit than from a manager's framework, and they already know who is good at what. The word 'exactly' matters here: a colleague's confidence is not something anyone can copy, but the way she opens a pricing conversation is.
Where do you want to be in two years, and does this job get you there?
Why ask it
Some reps want management, some want larger accounts, and some want to keep doing exactly this and be paid well for it. All three are fine answers, and each one changes which deals, projects and training you should steer their way.
What is wearing you down at work that has nothing to do with your number?
Why ask it
A territory change, friction with a colleague, or a run of evenings spent on proposals shows up in results a quarter later. You do not have to fix it in the meeting. Often the useful part is that it has been said to someone who can.
What do I do that makes your job harder?
Why ask it
Expect something small the first time, such as late approvals or meetings booked over the best calling hours. Fix that small thing where the rep can see it, and the next answer will be more candid.
What are you not telling me because you think I will not want to hear it?
Why ask it
Keep this for the end of a one on one, after enough goodwill to make an honest answer feel survivable, and then say nothing until they answer. What comes out is often the single most valuable thing in the conversation, from a lost deal to a rep who is interviewing elsewhere.
New team
What should I understand about this team before I change anything?
Why ask it
A new sales manager is expected to arrive with a plan, and opening with this signals that the plan is not finished. Take notes in front of them and put the same question to every rep, since the points that repeat are the ones to act on.
What did the last manager do that you would want me to keep?
Why ask it
It is easier to praise a habit than to criticise a person, so this draws an honest picture of your predecessor without inviting gossip. What goes unmentioned is as telling as what gets named.
What were you promised that I should know about?
Why ask it
Spoken agreements about accounts, a promotion timeline or a pay exception rarely survive a change of manager unless someone asks. You may not be able to honour every one, so check what is on record before you answer, but hearing about it now beats breaking it by accident.
How was your territory or account list decided, and does it seem fair to you?
Why ask it
Territory is where old grievances live, and a new manager is the first person in a while who can hear them without having drawn the map. Do not promise a redraw in the room. Say when you will look at it and which numbers you will use.
Which customer should I meet first, and what should I know before I do?
Why ask it
The rep's choice shows which relationship they are proudest of or most nervous about. Going in briefed by them, and alongside them, also makes clear that you are there to back the account and not to take it over.
How do you want me to handle it when one of your deals is going badly?
Why ask it
One rep wants you on the next call, and another wants a sounding board and to be left to run it. Settling the terms while nothing is on fire means your first intervention will not read as a loss of trust.
What is the first thing you would fix if you had my job?
Why ask it
Each rep has had this answer ready since before you arrived. Choose one fix that several of them name and that sits within your authority, and make it in the first month, because an early visible change earns patience for the slower ones.
What would make you say, three months from now, that I was a good manager for you?
Why ask it
The answers differ more than you would guess: faster approvals, protection from side projects, blunt feedback, simply being left alone. Write each one down and read it back to them at the three month mark.
Getting Straight Answers From a Sales Team
Practical guidance for the conversation itself
How to Run the Conversation
Split the deal review from the coaching talk
Pipeline inspection makes reps defensive, and defensiveness kills coaching. Run the deal questions first, close the laptop, then ask the Coaching group: skills, a call to hear together, where the job is heading, and what they are holding back.
Always ask for the deal name
Answers given in categories, such as enterprise deals take longer, are unfalsifiable. Make every claim attach to a named account, a named person, and a date, and the vague deals reveal themselves immediately.
Count to five after the answer
The first response is the prepared one and the second is usually the truth. Most managers fill the pause with their own opinion and never hear the second answer.
Write down what you committed to
If you ask what a rep needs from you and then do nothing, the question becomes noise and they stop answering it honestly. Read your commitments back at the start of the next one on one.
Ask the hard ones one on one
Nobody names a slipping deal, a broken process step, or a bad comp plan in front of eleven peers. Save the team meeting for pattern questions such as the common objection, where the answers benefit from being compared out loud.
With a team you have just inherited, ask before you inspect
Spend your first round of one on ones on the New team group and leave the forecast for the second round. Reps who have just lost a manager are deciding how much to tell the next one, and opening with an audit of their deals settles that question for them.
The Ten to Start With, and Which to Add for Each Meeting
- The ten to start with: questions 1, 2, 3, 9, 10, 13, 18, 20, 36, and 42. Between them they cover the deal a rep is proudest of, the thin part of the pipeline, the forecast, the riskiest deal, the signer, the reason to buy now, your own help, the common objection, one skill, and whatever is going unsaid.
- Weekly pipeline call: questions 2, 4, 5, 9, 12, and 13, which open on where the pipeline is thin and then tie every answer to a named deal and a next step.
- Monthly one on one: questions 1, 3, 6, 18, 37, and 42, which mix a deal they are glad of, a forecast, a past miss, a request, a call to review together, and a chance to raise something uncomfortable.
- Quarterly business review: questions 3, 15, 16, 17, 26, and 35, so the discussion covers pricing behavior, loss patterns, repeatable wins, expansion, and incentives rather than only the number.
- Team meeting or sales kickoff: questions 19, 20, 22, 23, 24, and 34, where hearing all the answers side by side exposes messaging and product gaps.
- New rep in their first 30 days: questions 18, 20, 21, 25, 27, and 36, because a newcomer still notices the awkward parts of your pitch and process that everyone else has stopped seeing, and asking what they need early sets the habit of requesting help.
- A team you have just taken over: the New team group, questions 43 to 50, spread across your first one on one with each rep and asked before anything about the forecast.
- After a missed quarter: questions 2, 8, 16, 28, 6, and 42, asked in that order so you diagnose before you discuss accountability.
- Deal specific review on one large opportunity: questions 10 to 14 in a row, each put to that one deal instead of the deal the question names, plus a walk through every stakeholder by name.
Answers That Should Worry You
- They are really interested, with no next meeting booked on a calendar.
- The next step is to follow up, or to check in next week, which means nothing has been agreed with the customer.
- A strong champion but no contact with anyone who controls budget or signs.
- The close date matches the end of your quarter rather than anything happening in the customer's business.
- Every deal in the pipeline sits in the same middle stage, which usually means stages are being used as a filing system rather than a forecast.
- Legal, security, or procurement described as a formality, when any of the three can add weeks and change terms.
- The reason for winning the last deal is the same as the reason for losing the last one, which suggests neither was really understood.
- A full pipeline made up entirely of leads that were handed over, from a rep who cannot say what they would do if the leads stopped.
- The same feature request waved away as being on the roadmap, when nobody in the room has checked that it is.
- Nothing at all comes out when you ask what they are not telling you, from a rep who has been quiet for a month.
Mistakes That Shut Down Honest Answers
Answering your own question
Adding your theory to the question, such as asking whether the deal stalled because of pricing, hands the rep an easy exit. Ask the open version and let the awkward silence do the work.
Turning every answer into a lesson
If disclosing a problem reliably produces a fifteen minute lecture, reps learn to disclose less. Sometimes the right response is to write it down, thank them, and move on.
Asking why the number is down before asking what changed
Why invites justification while what changed invites information. Territory shifts, a competitor's new pricing, and a broken lead source all show up under the second phrasing and hide under the first.
Inspecting only the deals that are already closing
The reviewable pipeline is the comfortable one, and the real problem is usually the empty top of the funnel two quarters out. Reserve part of every review for deals that do not exist yet.
Changing a new team's routine before you have asked about it
A manager who rewrites the stages, the forecast call and the territory map in the first fortnight makes the New team questions pointless, because nobody believes their answers will count. Ask, wait a few weeks, then change the thing most of the reps named.