Most sales managers coach the same way. They listen to a few calls, trust their gut, and give every rep roughly the same advice. Then they wonder why it sticks for a few reps and bounces off the rest of the floor.
The fix is usually sharper questions. A good one makes a rep stop, think, and land on the answer themselves, and that's the kind of feedback that reliably changes what they do on the next call.
Alpharun works with leading Medicare brokerages like Chapter, coaching hundreds of advisors across hundreds of thousands of calls. On a floor that size, sharper questions are how a manager moves the middle 80%.
So here are 60 sales coaching questions, grouped by the situation you're coaching through, with a quick-start 10 from those categories up front. When you're ready to check results, here's how to measure whether your coaching is actually working. Every one is written for a manager to ask a rep.
10 sales coaching questions to ask in every session
Short on time? Start here. These 10 pull from the categories below and work in almost any one-on-one, whether you're prepping a rep for a big call or picking apart one that went sideways.
What does success look like for you this quarter? Gets the rep to define the target in their own words.
What's your main outcome for this week? One clear focus beats five vague ones.
How do you feel about your pipeline right now? Their gut read tells you where to dig.
What's stopping you from moving this deal forward? Surfaces the real blocker, which is often internal.
Which part of the sales process feels hardest right now? Points your coaching at the right skill.
What's your goal for this call? Reps who name it run tighter calls.
Listening back, where did this call drift from your playbook? Turns a recording into a lesson.
If you ran this call again, what's the one thing you'd change? Builds the reflex to self-correct.
What's one thing you'll commit to this week? Small and specific beats big and fuzzy.
When should we review your progress on this? Accountability only works with a date on it.
Each question earns its spot, and the sections below group them by situation so you can grab the right set fast. For a deeper system, see our guide to data-driven sales coaching.
10 questions about goals and strategy
Goal clarity drives performance. These sales coaching questions help reps connect what they do every day to the bigger number.
What does success look like for you this quarter? Get specific. "Hit quota" is too vague to coach. "Close 40 policies this month and lift my quote-to-sale rate to 30%" gives you something to work with.
What stands in the way of reaching that goal? Reps tend to point at outside problems. Help them see what they can actually control.
Which clients bring you the most value, and why? Shows whether they understand your ideal customer. If they can't answer, that's your coaching focus.
What's your main outcome for this week? Weekly goals keep reps pointed at what matters and stop the scattered effort.
How will you know you've reached that outcome? "Better discovery" needs a definition. "Ask three budget questions on every call" works.
Which deals should you walk away from? Strong reps disqualify early. Teaching that protects their time for buyers who are ready.
What has to happen before you can close this deal? Breaking the deal into steps exposes the blockers hiding in it.
Which skill or knowledge do you need for your next goal? Let them name the gap before you do. It sticks better that way.
How does your personal strategy line up with the team's? Ownership shows up when reps see how their goals feed the bigger ones.
What will make you go the extra mile here? Motivation is personal. Knowing each rep's version tells you how to coach them.
Alpharun grounds these conversations in what actually happened on the calls, so you're not coaching from half-memories. When you can see which playbook steps a rep hit and which they skipped, every question gets sharper.
10 questions about pipeline health
Pipeline coaching gets reps honest about the real state of their deals. Your forecast depends on it. These questions pull the truth out.
How do you feel about your pipeline right now? Start with the gut check. Confidence or worry tells you where to look first.
Why is each of these deals in your pipeline? Strong pipelines hold deals the rep chose to work, each with a clear reason to be there.
Which opportunities aren't as promising as you first thought? Every rep has deals that looked great and now feel shaky. Find them early.
What happens if your biggest deal goes quiet? A backup plan gives you control. When one deal carries the month, a single "no" sinks the number.
What's stopping you from moving this deal forward? Often it's an internal gap: unclear messaging, missing materials, no next step.
Which stage of your pipeline is hardest to get through? Patterns show up fast. If discovery always stalls, that's the fix.
Looking at win rate, deal size, and cycle length, where can you improve? Setting plenty of appointments but few enrollments? Something's leaking. Pick one metric to work on.
What needs to happen to fill your pipeline next month? Future planning protects momentum before it slips.
Are you assuming anything about this deal that might not be true? Assumptions hide risk. Challenge them now, not at month's end.
When should we review your progress on this? Clear checkpoints build accountability. Regular sales performance reviews keep reps on track.
10 questions about skills and performance
Skill gaps quietly cap a rep's results. Use the next 10 to help reps spot where to put in the work, which beats being told.
What could you do differently to be more effective? Gets reps looking at their own habits before you point at them.
Which part of the sales process feels hardest right now? Naming it focuses your coaching where it pays off.
How did the competition beat you on your last loss? Lost deals show you what buyers actually value.
What value do you bring that makes prospects want to talk to you? Reps who can answer this sell with more confidence.
Would customers pay to access your expertise? If the honest answer is no, help them build deeper knowledge.
What do you want to do more of, and less of? Clarifies how they're spending their hours and where the high-impact work hides.
Which habits from your top performers could you borrow? Pair a strong prospector with a strong closer and let them trade.
What support do you need from the company to improve? Sometimes the blocker is a broken process or a missing script. Clear it.
How have you helped a teammate this month? Peer coaching spreads what works across the whole floor.
What's one thing you'll commit to this week? Focused reps improve faster than busy ones.
Want software built for this? See our roundup of sales coaching software.
10 questions for call planning and preparation
Preparation is what separates a decent call from a great one. These questions get reps thinking before they dial.
What's your goal for this call? A specific goal, like confirming budget or timeline, keeps the call tight.
Who should be on this call that isn't? Missing decision makers, like a spouse who shares the bills, stall deals. Get the right people in early.
What might they ask to throw you off? Anticipating the hard questions lowers the odds of getting rattled live. Call center agent scorecards help you spot where reps tend to wobble.
What would make them choose you over doing nothing? If you can't beat the status quo, you can't win the deal.
Where do the required disclosures fit in this call? Planning them into the flow keeps them from getting rushed or skipped.
If they say X, what's your response? Rehearsed reps handle pressure better and keep the call on track.
How likely is this outcome, really? Honest forecasting keeps your pipeline grounded.
What's your next action to move this toward close? A concrete next step moves the deal; a vague intention lets it stall.
Who's on the call, and what does each person care about? Tailored messaging lands harder than a generic pitch.
What have you already tried with this prospect? Context stops reps from repeating moves that already flopped.
10 call review questions to ask after a scored call
Alpharun's call analysis, rating how a rep handled a skeptical buyer and quoting the line from the call.
Pre-call prep is one half. The other half happens after, when you sit down with a rep and a recording of a call that already went out the door. This is where most coaching either clicks or evaporates.
The catch: nobody can review every call from memory. Alpharun scores each call against your playbook and surfaces the exact moments worth replaying, so these questions start from what happened instead of what the rep thinks happened.
A Medicare advisor reviewing a recorded enrollment call, for example, can see precisely where the disclosure slipped or the needs analysis got thin. For more worked examples, see our call center coaching examples.
Listening back, where did this call drift from your playbook? Lets the rep catch it before you say a word.
Did the buyer agree to your agenda early on? If they never bought into the plan, the rest of the call was uphill.
Where did you lose their attention, and why? Find the exact moment the energy dropped.
Which of your questions got the most useful answer? Reinforces what's working so they do more of it.
Did the buyer reveal their real needs, or did you assume them? Assumptions made here cost deals later.
How did you handle the main objection? Replay the moment and talk through alternatives.
Did you confirm the next step before hanging up? A call with no next step is a call you'll be chasing.
If you ran this call again, what's the one thing you'd change? Keep it to one. Reps fix one habit at a time.
Which moment here would you want a new rep to copy? Turns a good call into a training clip.
What will you do differently on your next call like this? Closes the loop between review and the next dial.
10 questions about customer understanding
The strongest deals come from reps who genuinely get their buyer. The next 10 coach reps to see the deal through the buyer's eyes.
What problem is this customer really trying to solve? If a rep leads with features, they've missed the point. Coach them to start from the problem. The Sandler Pain Funnel helps reps move from surface issues to the real motivator.
What does this customer care about most? Price, coverage, or peace of mind: deals close when the rep knows which one decides it.
Why should they care about this at all? If the rep can't explain why it matters to the buyer, the buyer won't either.
What would make them do nothing? Doing nothing is always an option for the buyer. Name it early.
Who are you talking to, and who should you be talking to? Coach the rep to confirm they're with someone who can actually decide.
What's keeping them tied to the status quo? Change feels risky to buyers. Help the rep guide them through it.
How happy are they with what they have now? The rep needs to know the size of the gap before positioning anything.
What do they need to believe to buy from you? Every deal turns on a belief shift. Find the one that matters.
What would this customer say about you right now? Builds the rep's empathy and sharpens their read.
How will competitors try to win this? Anticipating their pitch lets the rep prepare counterpoints in advance.
Open vs closed coaching questions, and how to react to the answer
Open questions ("What got in the way this week?") pull out stories and reasoning. Closed questions ("Did you confirm the budget?") pin down a fact fast. Both earn their place in a coaching session, so don't get precious about only asking open ones.
The bigger lever, though, is what you do with the answer. The sales-training firm Funnel Clarity argues the open-versus-closed debate misses the point: what matters most is how the seller responds to the answer. The same is true in a coaching session. Ignore a rep's reply and jump to the next question, and the whole thing starts to feel scripted.
So when a rep answers, react. Acknowledge what they said, ask a follow-up that proves you listened, and sit with the silence before filling it. A closed question followed by real curiosity beats a perfectly phrased open question followed by a blank stare. The question opens the door. Your reaction is what walks the rep through it.
How to match coaching questions to each rep type
The same question that fires up a top performer can shut down a struggling one. Before you pick which questions to ask, figure out whether you're dealing with a skill gap or a will gap, then match your approach to the rep in front of you.
New reps
You're building confidence and fundamentals. Keep it concrete and low-stakes.
What's your goal for this call?
What have you already tried with this prospect?
What's one thing you'll commit to this week?
Struggling reps
Diagnose before you prescribe. Find out if it's skill or motivation first.
Which part of the sales process feels hardest right now?
What's stopping you from moving this deal forward?
What support do you need from the company to improve?
Steady middle performers
Moving the middle 80% closer to your best reps is usually the biggest lever on the team's number.
Which habits from your top performers could you borrow?
Looking at win rate, deal size, and cycle length, where can you improve?
What do you want to do more of, and less of?
Top performers
Don't leave them to coast. Top reps want a stretch goal and a reason to keep improving.
Which moment on your last call would you want a new rep to copy?
What would you do differently if you ran that deal again?
How have you helped a teammate this month?
How to use these sales coaching questions effectively
The questions only work with a little bit of discipline. Without it, they turn into a checklist that the rep learns to tune out.
Ask, then keep quiet
Don't rush to fill the gap. The silence after a good question is where the thinking happens. Let the rep sit in it, even when it gets a touch awkward.
Follow up with more questions
When they answer, go deeper. "How so?" "Tell me more about that." "Why?" Three tiny questions that pull out more than any statement you could make.
Help them solve it themselves
When a rep brings you a problem, resist fixing it for them. Guide them to their own answer. They have to think on their feet with prospects anyway, so let coaching be where they practice it.
Track progress over time
Write down what you cover. Reference the last session. Showing a rep how far they've come is its own motivation, and it keeps you honest about whether the coaching is landing. Pull the context from your call detail reporting software.
How to make sales coaching questions part of your culture
You get the full value when coaching stops being a one-off and becomes a habit the team expects. It earns the calendar space, too: back in 2011, Sales Executive Council research found that no other productivity investment comes close to coaching for improving rep performance, which makes the standing meeting easy to justify.
Schedule a weekly 30-minute session: Protect it. Consistency builds the trust that honest coaching needs.
Use the same core questions with every rep: Patterns across answers tell you when the whole team needs help with something.
Celebrate wins that came from coaching: Proof that it works keeps reps leaning in.
Share what reps learn from each other: Good habits spread faster peer to peer than top down.
Running a distributed team? The same weekly rhythm works over video, and our guide to remote sales coaching covers how to keep it consistent.
Coach every rep from your best calls with Alpharun
Great questions get you most of the way. The last stretch is knowing which calls to ask them about, because coaching from memory means coaching from the handful of calls you happened to catch.
That's where Alpharun comes in. It scores every call against your playbook, flags the moments worth reviewing, and ties your coaching questions to what reps actually did on the real call.
With Alpharun, managers can:
Score every call against your own compliance rules and sales criteria, consistently across reps and teams
Surface the exact moments worth coaching, so you walk into every one-on-one already knowing what to ask
Send reps short coaching notes right after their calls, which takes work off your plate
Build playbooks from how your best reps actually sell, then spread those habits across the floor
Track progress toward coaching that lifts performance, measured on real outcomes
You still run the conversation. Alpharun makes sure every sales coaching question you ask starts from what happened on the call. Book a demo to see how Alpharun turns your calls into coaching that reps can act on.
Frequently asked questions
What are the 10 best questions to ask during a coaching session?
The 10 best questions to ask during a coaching session cover goals, pipeline, skills, and the last call. Ask what success looks like this quarter, what's blocking a key deal, where a recent call went off the playbook, and what the rep will commit to this week. The quick-start list at the top of this guide has all 10.
What are the 5 C's of sales?
The 5 C's of sales are customer-centricity, communication, closing, consistency, and continuous learning, in one widely shared version from DealHub. There's no single standard list, so other trainers swap in traits like confidence or credibility.
How often should you hold sales coaching sessions?
Hold a dedicated coaching session with each rep weekly, kept to about 30 minutes. A weekly rhythm keeps coaching close to the calls it's based on, and consistency tends to matter more than session length, so a short standing meeting beats an occasional long one.
What's the difference between sales coaching and sales training?
The main difference between sales coaching and sales training is scope: training teaches a specific skill to a group, usually in a set curriculum. Sales coaching is personalized and ongoing, helping an individual rep apply those skills to their real calls and deals. Training builds the baseline; coaching turns it into performance on the phone.
