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Introduction
Sales coaching is not easy to do well.
A lot can go wrong before the manager even asks the first question of the coaching session. Some sales managers are promoted because they were strong sellers, not because they know how to coach. Some have never been taught how to run a coaching conversation in the first place.
Others slip too quickly into advice-giving, deal inspection, or problem-solving mode, instead of coaching salespeople to think their way through the situation.
Part of the issue is that the term “coaching” itself is often misunderstood.
In my case, coaching has always been a strong interest. At one point in my sales career, I decided to invest in a formal certification with the International Coaching Federation – an experience that clarified something important for me: coaching is NOT mentoring, consulting, or advising.
It is a distinct discipline.
It is not about providing answers, fixing problems, or telling someone what to do next. Effective coaching conversations are about helping the person think more deeply than they would on their own, see their situation more clearly, and arrive at better decisions and actions through reflection.
In many ways, coaching is like holding up a mirror. You are not there to direct. You are there to surface thinking, challenge assumptions, and increase ownership. The motivation, the clarity, and the commitment need to come from the individual.
When coaching gets replaced with instruction or inspection, the conversation may still happen, but the thinking does not move.
Even when the intent is right, coaching can underperform because the questions do not fit the moment. For example, a confidence gap may get treated like a pipeline problem, or a strategic account conversation may turn into deal inspection.
Due to these mismatches, the session happens, but little changes in the end.
As I pointed out in my sales coaching guide, coaching is not a one-size-fits-all practice. It takes different forms, serves different needs, and works best when it helps the salespeople identify problems, develop better judgement, clearer priorities, and committed next steps.
In this article, we focus on one of the most overlooked aspects of coaching: asking the right questions in the right moment.
In general, I am not a big believer in long lists of questions, whether in coaching or in sales. The risk is that they get used in a mechanical way, which defeats the purpose. Coaching, like sales, is not about following a script, but rather about responding to the situation in front of you.
That said, well-structured sets of questions can still be an extremely useful part of a sales coach’s arsenal.
The questions provide direction, spark ideas, and help managers approach conversations with more clarity. This is especially valuable for new managers and sales leaders who are developing their coaching skills, or for enablement teams building playbooks to support frontline managers.
For this reason, this piece is designed to offer a structured set of sales coaching questions, organised by coaching type, so managers can better match their questions to the situation they are facing.
Some questions help reps think through deal risk, stakeholder influence, or customer priorities. Others focus on territory management, pipeline judgement, skill development, or the assumptions that may be getting in the way.
Asking better coaching questions leads to better thinking, which in turn drives better actions and sales success.
What makes a good sales coaching question?
If I were to get down to the core of what makes a good sales coaching question, it’s this: it improves the quality of the rep’s thinking.
It should help them see the situation more clearly, challenge their assumptions, notice what they may be missing, and move towards a better decision or next step.
In practice, strong coaching questions usually do five things:
- Clarify the situation – They help the rep separate facts from assumptions, opinions, or wishful thinking.
- Sharpen judgement – They push the rep to interpret the situation more clearly, weigh trade-offs, and think more strategically.
- Surface blind spots – They reveal what the rep has not yet seen, tested, or fully considered.
- Create forward movement – They turn reflection into action, so the conversation does not end with vague awareness and no follow-through.
- Fit the moment – They match the stage of the conversation. Early in the coaching exchange, open-ended sales coaching and probing questions often work best because they help the rep explore the situation more fully. Later on, once the thinking is clearer, more focused or closed questions can help test commitment, confirm priorities, and define next steps.
As I often share with others, effective coaching supports self-discovery rather than defaulting too quickly to answers.
That doesn’t mean the manager stays passive.
In many coaching moments, especially around deals, accounts, or pipeline, the manager still plays an active role as a thinking partner. And at times, they may step in with guidance or advice.
This tends to be most appropriate when the rep has explored the situation fully, has run out of options, or lacks the experience to move forward on their own. In such moments, blending coaching with mentoring can be both practical and necessary.
I’d argue that less experienced reps often benefit from a mix of coaching and direction, while more experienced sellers tend to benefit more from a non-directive approach that improves their own judgement.
The key is to make that shift explicit.
When moving from coaching into advising, you should communicate it clearly, almost as if you are taking off your coaching hat and putting on your advising hat for a moment. Creating clarity around that keeps the interaction deliberate and avoids defaulting into instruction too early.
Even then, the goal remains the same: improve the rep’s thinking first, rather than taking the thinking away from them.
Turn sales call insights into revenue-driving action
Before you ask anything, identify the right coaching type
Before you choose the question, you need to diagnose the coaching job.
That step gets missed more often than it should. Managers jump into the conversation with a favourite question, a familiar framework, or a piece of advice they have used before.
Sometimes it helps, but most often, it does not, because the issue in front of them is not the one they think they are coaching.
Coaching takes different forms, and each one is tied to a different sales performance need.
That is why the first move is to ask yourself what kind of coaching this situation actually calls for.
A simple way to diagnose it is this:
- Is this about a specific deal in progress? → Opportunity coaching
- Is this about a broader customer or account strategy? → Account coaching
- Is this about how the rep is prioritising across their territory? → Territory coaching
- Is this about pipeline quality, coverage, or focus? → Pipeline coaching
- Is this about how the rep is handling sales conversations? → Skills coaching
- Is this about mindset, confidence, or self-awareness? → Developmental coaching
Once you identify the coaching type, you can ask more focused and targeted questions that are appropriate for the situation and make for much more effective coaching conversations.
Sales coaching questions by coaching type
The best coaching questions depend on how the conversation is supposed to create major positive shifts.
A manager coaching a live deal needs a different set of questions from one helping a rep improve discovery, rethink territory focus, or work through a confidence issue.
That is why I organised the following questions by coaching type.
Once you’ve identified the type that fits the situation, use this section as a practical reference point.
I wouldn’t recommend using these as a rigid script.
A better approach is to start by selecting a small number of questions that you believe would help the rep think more clearly, spot what is missing, and move towards stronger next steps within their particular context.
You should also avoid mixing too many coaching objectives in the same conversation. If you try to address a deal, a pipeline issue, and a confidence concern all at once, you will usually end up skimming across all three without going deep on any of them.
In most cases, two to four well-judged questions are enough. A shorter, more focused exchange tends to create better thinking than a long list that overwhelms or puts the rep on the defensive.
Once you ask the question, give it space.
Let the rep think, respond, and work through the situation fully. Great sales coaches know how to resist the urge to step in too early, tidy up their answer, or move straight to their own view.
The value often comes from what the rep processes out loud.
From there, bring the conversation to a clear next step.
Coaching should not stop at insight; it should lead to action.
What will the rep do next?
What will they test, change, prepare, or follow up on?
Keep it specific enough that progress can be observed and reviewed in the following session.
It is also worth highlighting the importance of maintaining a neutral stance. If the rep feels they are being assessed or judged rather than supported, they are less likely to share their full thought process, and the effectiveness of the coaching will suffer.
Finally, keep the prospect’s business at the centre.
Regardless of coaching type, the discussion should stay anchored in how the salesperson creates value, helps the buyer move forward, and supports better decisions, rather than focusing only on internal activity.
As a reminder, coaching questions work best when they improve how the rep thinks, acts, and engages with the buyer or customer.
Opportunity coaching questions
Opportunity coaching focuses on live deals and how they move.
In my experience, it works best when it starts early, not only when a deal is already under pressure or close to slipping.
The role of opportunity coaching is to help the rep think more clearly about deal quality, buyer priorities, buying influence, deal risk, and the next move most likely to improve the state of the opportunity.
At its best, it keeps the buyer at the centre, rather than reducing the conversation to seller activity or internal process alone.
Turn sales call insights into revenue-driving action
Qualification and opportunity quality
What makes this a real opportunity, rather than just an active conversation?
I tend to use this early, especially when a deal has a lot of activity but not much “substance”. In many deals, activity creates a false sense of progress. This brings the conversation back to what is actually there.
What evidence do you have that this problem is important enough to get solved now?
This question is useful when a deal sounds compelling, but urgency is unclear. It pushes the rep to move beyond general statements and point to concrete signals from the buyer.
If you had to disqualify this opportunity today, what would be the reason?
I come back to this question when a deal feels too “comfortable”. By asking this, you encourage the rep to challenge their own narrative and surface what is not working. Often, it brings out risks that would otherwise stay hidden until much later in the sales cycle.
Why does this deserve your attention over your other open opportunities?
This question supports better prioritisation. Reps often evaluate deals in isolation, but, as we know, not all opportunities deserve equal focus.
What has the buyer actually done that indicates intent, not just interest?
This question helps separate polite engagement from buying movement. It is especially useful in deals where the buyer is responsive, but has not yet made any meaningful commitment.
Buyer problem and business impact
What is the buyer actually trying to change?
This question pulls the rep away from product talk and back into the customer’s world, often uncovering whether the deal is anchored in a real business priority or just a surface-level need.
How is this problem affecting the business today?
A useful question for moving from vague pain points to tangible impact. Without that shift, the opportunity often stays too weak to drive action.
What happens if the buyer does nothing?
I find this is one of the simplest ways to test whether the issue is merely uncomfortable or genuinely consequential.
Where are you relying on assumptions instead of buyer-confirmed insight?
This is a strong question whenever the deal story sounds too neat. It will help you expose where the rep may be filling gaps with internal guesswork.
Why would our solution matter more than the alternatives the buyer already has in place?
This question pushes the rep beyond feature comparison and into why this change would matter, if at all, in the customer’s context.
Which part of the buyer’s problem feels most urgent to them, and which part feels most urgent to you?
This is a useful way to expose misalignment. In some deals, the rep is pushing on a priority (e.g., something from the company’s sales strategy) that the buyer does not feel with the same intensity.
Buying process and stakeholders
Who is likely to shape this decision, even if they are not the formal decision-maker?
A very strong question in complex deals. Influence and authority rarely sit in exactly the same place.
What does each key stakeholder care about most in this deal?
I use this question to test whether the rep has stakeholder-specific understanding, or is still relying on one generic message for everyone.
What do you know about how this account actually makes buying decisions?
This question helps shift the rep from your sales process to the buyer’s process, which is where a lot of deals are either understood properly or misread.
Where do you have support, and where do you still have a relationship gap?
A useful way to assess internal coverage. Many deals look healthy until you realise support is concentrated in only one part of the account.
Which stakeholder could slow this down the most, and why?
Use this question to help the rep surface hidden blockers before they become visible when it’s too late in the deal.
Who is likely to gain from this change, and who might feel disrupted by it?
A helpful question in change-heavy deals. Sometimes resistance is less about disagreement and more about perceived disruption.
Deal strength and risk
What is working in your favour in this deal right now?
I like to include this question because opportunity coaching should not only focus on risk. Strong deals usually have clear advantages, and you should prepare salespeople to recognise and build on them.
What feels most fragile in this opportunity?
A strong way to invite honesty, often getting past performance theatre and into what the rep is genuinely worried about.
If this deal slipped or died, what would the most likely cause be?
This is one of my favourite pre-mortem questions because it helps the rep anticipate risk instead of reacting to it later.
What are you treating as true that you have not actually tested yet?
Excellent for exposing false certainty. In many live deals, I believe this is where the biggest hidden risks sit.
Where could internal misalignment on our side create risk for the buyer?
A particularly useful question in complex or multi-threaded opportunities, as internal confusion often damages trust faster than reps realise.
Next steps and deal movement
What is the most important thing that needs to happen next for the buyer, not just for you?
This question helps re-centre the deal on the buyer’s progress rather than seller activity. Many next steps look productive internally, but do not actually move the customer forward.
What action would move this deal forward most meaningfully?
I use this question when a rep lists multiple next steps without clear prioritisation. Because it forces a choice, the question supports the rep in identifying the single action that would create the most momentum, rather than spreading effort across lower-impact activities.
What exactly has the buyer agreed to do next, and by when?
This question tests for real commitment. There is a big difference between “they seemed open” and “they agreed to do X by Y”. When this answer is vague, it usually signals that the deal is not as advanced as it appears. Instead, clear answers indicate alignment and forward movement.
What is your plan if the buyer does not take that step?
Most deals are planned around the ideal path. This question introduces a more realistic view that helps the rep think through alternatives, develop strategies to regain control if momentum slows, and avoid being purely reactive when things do not go as expected.
What will you do to strengthen the deal or reduce the biggest risk before the next interaction?
This question shifts the focus from maintaining the deal to actively improving it. It is especially useful when risks have already been identified.
At this point, is the right move to advance, rework, or step back?
I find this a valuable closing question because it creates space for honest evaluation. I believe that not every deal should be pushed forward. Sometimes the right move is to pause, fix something, or even step away.
Account coaching questions
Account coaching focuses on the broader account: multiple buying centres, the wider business context, relationship depth, and long-term growth.
It takes a step back from individual deals and looks at how the rep is positioning within the account as a whole.
The goal is to help the rep build a clearer view of the customer, strengthen relationships across stakeholders, align their approach to the customer’s priorities, and expand the account in a deliberate, structured way over time.
Account context and strategic priorities
What is changing in this account’s business that should shape how you engage them?
I like this question because it pulls the rep up from deal activity and back into the account’s wider reality. In strong account work, engagement should evolve as the customer’s business evolves.
Which strategic priorities matter most inside this account right now?
This question is one of the clearest ways to test whether the rep understands what the customer is actually trying to achieve.
How does our offer connect to those priorities in a way the customer would recognise as meaningful?
A useful question for checking whether the rep can link the offer to real business priorities. It moves the conversation away from capability lists and towards value that would make sense inside the account’s context.
Where are you still relying on old account assumptions that may no longer be true?
This question is especially helpful in long-running or familiar accounts. In my experience, the more history a team has with an account, the easier it becomes to operate on outdated assumptions without realising it.
Whitespace and expansion potential
Where is the biggest unrealised opportunity in this account today?
This question helps move the rep’s thinking beyond account maintenance and into account growth planning. It is particularly useful when the account seems active, but the account strategy remains too close to what was already in play.
Which buying centres, teams, or use cases have we not explored properly yet?
A good way to surface whitespace that may be hidden by over-focus on current contacts or existing revenue streams. In many accounts, growth is limited less by lack of opportunity than by narrow coverage.
Where do we have the right to expand, and where would expansion still feel premature?
I like this question because it sharpens judgement around timing and credibility. Just because an opportunity exists does not mean the account is ready for that conversation yet.
What part of this account’s business are we still underestimating?
A useful question for surfacing blind spots in the account view. It often reveals areas the rep has not looked at deeply enough, especially in larger or more complex accounts.
Stakeholder mapping and influence
Who matters most in this account, and why?
This question tests whether the rep has a real view of influence, or just a list of names and titles. The rep needs a view of who actually matters to momentum and decision-making within an account.
Where does formal authority sit, and where does practical influence sit?
A particularly useful distinction in complex accounts, where the two often do not line up. Reps who collapse them into one usually miss important dynamics.
What does each key stakeholder care about in this account?
I use this question to move from surface-level mapping to stakeholder-specific insight, helping expose whether the rep truly understands the key stakeholders’ world and tailoring their approach to that rather than still relying on one generic account narrative.
Relationship strength, sponsorship, and risk
Where are your relationships strong, and where might they not be deep enough for what you’re trying to achieve?
A very practical way to assess relationship depth. Many accounts look healthy until you realise the relationship base is too narrow to support future growth or the resilience of the deal.
Who is acting like a genuine sponsor or champion in this account, and what makes you believe that?
I find this useful because reps often apply those labels too loosely. This question forces them to point to observable behaviour.
If your main contact left tomorrow, what would still hold inside this account?
One of the best questions for testing account resilience. If the answer is “not much”, the account is usually in a weaker position than it appears.
Where do you still have a relationship gap that could limit progress later?
This question helps surface any weak coverage before it becomes a blocker. In many cases, the risk is not visible in the current deal, but it becomes obvious later when the account needs broader support.
Whose perception of us matters more than we may realise?
A useful question for uncovering quieter stakeholders who influence trust, momentum, or resistance from the background. These are often the people teams notice too late.
Who is supportive, but not yet committed enough to help move things internally?
A strong question for distinguishing soft support from real internal sponsorship, as it often exposes where a rep may be having too much optimism, but not yet enough leverage.
Account planning and strategic focus
How are you currently planning and managing this account?
A useful question to understand whether the rep is managing the account deliberately or reacting to what is in front of them. Strong answers usually reveal clear structure, priorities, and intent.
What is the account strategy trying to achieve beyond closing the next opportunity?
This question lifts the conversation above short-term revenue and into longer-term account value. In my experience, this is where more strategic account coaching starts to sound different from deal coaching.
How are you segmenting this account in a way that helps you focus?
This question checks whether the rep is making deliberate choices about where to invest time and attention. Without that, the account strategy often becomes too broad to guide action.
What would a strong next quarter in this account look like, and what has to happen to make that realistic?
A good closing question for turning account thinking into a practical plan because it helps connect strategy to outcomes and makes the next phase more concrete.
Turn sales call insights into revenue-driving action
Territory coaching questions
Territory coaching focuses on how reps allocate their time, attention, and effort across their book of business.
It should help them step back from individual deals and think more deliberately about where to focus, which segments or accounts to prioritise, and whether their effort is aligned with the best opportunities available.
Territory focus, selection, and priorities
What parts of your territory are most likely to produce meaningful results over the next quarter?
I like this question because it moves the rep away from generic coverage and towards more focused prioritisation. In many territories, the issue is not a lack of opportunity, but a lack of focus on the key accounts most likely to produce real results.
Where are you currently leaning in too hard, and where are you underplaying real potential?
A useful question for exposing focus patterns driven more by habit than evidence. It often reveals where the rep is over-investing in familiar areas while missing better opportunities elsewhere.
What is your territory strategy trying to optimise for right now: pipeline, expansion, deal quality, or something else?
This question helps clarify the rep’s operating logic. Without that clarity, territory activity can become busy and reactive, with no real sense of what success is meant to look like.
If you had to narrow your focus by 20 per cent, what would you stop doing first?
A strong prioritisation question. I find it especially useful when the rep is trying to cover everything at once and needs help making better trade-offs.
Which segments or account types are giving you the best return on time and effort?
This question helps test whether the rep actually knows where traction is coming from. Strong answers are usually grounded in observed patterns, rather than just isolated wins or preferences.
What patterns do you see in the accounts that are moving, versus the ones that are stalling?
A good question for turning scattered territory experience into a useful judgement so that the rep can identify what stronger accounts or weaker ones tend to have in common.
Where are you chasing accounts that look attractive on paper, but rarely convert in reality?
I use this question when a rep is drawn to accounts because they look like a strong fit at first glance, whether due to brand, size, industry, or perceived alignment, but those accounts consistently fail to progress.
What would make an account worth pursuing aggressively in this territory?
This question helps the rep define selection criteria more clearly. In my experience, territory execution improves when reps can articulate what makes an account genuinely worth deep focus, rather than relying on instinct alone.
Buyer-role coverage
Which buyer roles matter most in this territory, and how confident are you in engaging them well?
This is useful for testing whether the rep’s territory plan reflects who actually shapes buying. It also helps uncover whether their confidence is concentrated around a narrow set of personas.
Where are you over-indexed on one persona or function?
A helpful question when territory coverage is too narrow to support growth. In many cases, reps build comfort with one buyer type and then over-rely on that across the whole patch.
What buyer groups are under-engaged across your patch right now?
This question helps surface missed coverage that may be limiting pipeline quality, especially where the territory has broader potential than the rep’s current approach reflects.
How does your message need to shift across the main buyer roles in this territory?
A strong question for checking whether the rep is adapting their personal strategy to the different buyer roles rather than repeating one message everywhere.
Effort allocation and execution discipline
How are you deciding where your time goes each week?
A super simple question, but very revealing. It often shows whether the rep is operating intentionally or just reacting to what is loudest, most recent, or easiest to act on.
What activities in your territory are consuming time without moving you closer to the target?
This question helps the rep identify where time is being spent without producing meaningful progress. In many territories, a lot of effort goes into activities that feel productive, such as chasing low-quality accounts, over-servicing unresponsive prospects, or maintaining conversations that are unlikely to convert, but do not actually move results forward.
Where would a small shift in effort create a disproportionate gain?
I like this question because it looks for areas of leverage. Territory performance often improves more through better allocation than by simply doing more.
What are you doing because it feels productive, rather than because it is productive?
A strong question for challenging effort patterns that look busy, but add little value. It is especially useful when a rep is working hard, but results are not showing.
What would a more concentrated, higher-conviction territory plan look like from here?
This is a strong closing question because it pushes the rep to turn insight into action. It helps them define where they will concentrate effort, what they will step away from, and how their territory approach will change from here.
Pipeline coaching questions
Pipeline coaching focuses on how well the pipeline reflects reality, how opportunities are progressing, and how reliable it is as a basis for decision-making and forecasting.
This type of coaching should help sales reps step back from individual deals and assess the pipeline as a whole, looking at aspects such as stage accuracy, deal quality, conversion patterns, and the strength of customer commitment across opportunities.
At its core, pipeline coaching is about improving judgement at the funnel level, beyond single deals.
Pipeline reality and stage integrity
Why is this deal at this stage right now?
A simple but very useful question for testing whether the stage reflects reality.
What has the buyer done that justifies this stage placement?
A strong way to move the rep away from seller activity and back to buyer evidence. If the answer stays vague, the deal is often less mature than the stage suggests.
Which deals in your pipeline are probably staged too optimistically?
Useful when the pipeline looks healthy on paper, but feels less convincing in practice. It encourages a more honest look at whether stage labels are being used too generously.
Where are you driving a lot of activity without seeing meaningful movement from the buyer?
This is a strong way to surface one-sided deals since it supports the rep in recognising where momentum (if any) is being solely sustained by their own effort rather than by genuine buyer progress.
Prioritisation and resource allocation
Which deals deserve the most attention right now, and why?
I use this question to test whether the rep is prioritising based on real signals in the deal. Strong answers usually reflect a clear view of where the buyer is engaged, where timing is credible, and where focused effort is most likely to create forward movement.
Where are you over-investing in low-quality or low-leverage opportunities?
A strong question for exposing poor pipeline economics. Namely, highlighting where time is going into deals that show weak buyer engagement, unclear next steps, or limited potential to progress, while stronger opportunities receive less attention.
If you had to protect time for only a small number of deals this week, which ones would make the cut?
This forces sharper prioritisation when the pipeline feels crowded, helping the rep identify what truly deserves protected attention.
What are you neglecting because too much time is going into deals that feel urgent, but are not strong?
A great way to surface opportunity costs inside the funnel. In many cases, weaker deals do not just waste time directly; they also take away attention from stronger deals. The negative consequences of that can be quite significant.
Risk and forecast confidence
Which forecasted deals make you least comfortable, and why?
I like this question because it creates space for honesty. In many pipeline reviews, reps focus on what looks strong, but avoid talking about the deals that feel uncertain. This question helps bring those doubts to the surface.
What is the biggest hidden risk in your pipeline right now?
I tend to use this question when everything looks fine on the surface, but doesn’t fully add up. It helps the rep slow down and think about what might be sitting underneath the deals that haven’t been fully explored yet.
If your forecast missed this month, where would the miss most likely come from?
This is a very practical way to get ahead of problems. Instead of waiting to explain a miss after it happens, it encourages the rep to think now about where things could slip and why.
What assumptions are carrying too much weight in your commit or best-case calls?
I like to ask this question when forecast confidence sounds a bit too clean. As a result, reps should reflect on what they are taking as true without enough backing, and where some deals might be more fragile than they appear.
Where do you need more evidence before you can talk about this pipeline with real confidence?
This question helps move the conversation away from gut feel and towards something more “solid”. It encourages the rep to think about what they still need to see or confirm before they can genuinely stand behind the forecast.
Funnel patterns and performance signals
What pattern do you see across the deals that are progressing well?
I like this because it shifts the focus from fixing problems to understanding what is actually working. In many cases, the most useful insight comes from spotting what strong deals have in common, and then doing more of that on purpose.
Where do deals tend to stall in your funnel, and what does that suggest?
This question helps the rep step back and notice where things consistently slow down. Instead of treating each stalled deal as a one-off, it encourages them to look for potential patterns and think about what might be causing that friction.
What does your pipeline tell you about how you are selling right now?
I use this to connect outcomes back to behaviour. The shape of the pipeline usually partly reflects how the rep is approaching conversations, qualification, and follow-ups, so it’s a good way to surface what might need to change.
If we zoomed out from individual deals, what would worry you most about this pipeline?
This is a useful question to use when the conversation gets too focused on single opportunities. The idea is to help the rep take a step back and call out what feels off at a broader level, even if it’s not fully clear yet.
Turn sales call insights into revenue-driving action
Skills coaching questions
Skills coaching focuses on how reps behave in real customer interactions.
For the manager or whoever is coaching, the aim should be to improve how sellers run conversations, from discovery and listening, through to objection handling, value articulation, negotiation, and closing.
Rather than introducing new concepts, it builds on training by helping reps practise, reflect, and improve how they execute in live situations.
Discovery
What did you learn about the buyer that genuinely changed how you see this deal?
I like this because it tests whether discovery actually changed the rep’s understanding of the situation, rather than just adding more detail.
Where did you stay at the surface when you should have gone deeper?
A useful question for spotting where the rep heard something important, but did not explore it enough.
What business impact did the buyer actually confirm, rather than hint at?
This question helps separate what the customer clearly validated from what the rep may have inferred too quickly.
What do you still not understand well enough about the buyer’s priorities, pressures, or decision criteria?
A practical way to surface what is still unclear, before those gaps create problems later in the deal.
Which question opened the conversation up most, and why did it work?
I’ve always liked this kind of question because it helps the rep notice which questions led to more meaningful answers, so they can use that more deliberately next time.
Active listening
Where in the conversation did you respond too quickly instead of listening longer?
This is a powerful question to ask in situations where you notice that the rep tends to jump in before the buyer has fully finished the thought or explained the issue properly.
What did the customer say that deserved more follow-up than it got?
A strong way to help salespeople discover moments that could have opened up the conversation further, but were left unexplored.
How well did you reflect back on what you heard, rather than moving straight to your answer?
This question helps the rep self-reflect on whether they are summarising what they’ve heard in the buyer’s words effectively before trying to respond or persuade.
What assumption did you make in the moment that may have narrowed your listening?
A useful question when the rep may have heard the situation through their own lens rather than staying fully open to what the customer meant.
Where did you stop being curious too early?
A super simple question, but often very revealing. It helps surface moments where a little more curiosity and openness could have changed the direction or quality of the conversation.
Objection handling
What do you think was really underneath that objection?
I find this question effective at stopping the rep from reacting too quickly to the surface-level objection over time and encouraging deeper interpretation.
Did you try to resolve the objection too quickly, before fully understanding it?
A useful question to ask when it’s evident the rep tends to move into answer mode before really unpacking what the buyer meant.
How did you test whether the objection was the real blocker, or just the easiest thing for the buyer to say?
A strong question for helping the rep distinguish between a true concern and something more conversational or convenient.
What would a more useful response have sounded like in that moment?
This question helps move the discussion from critique into something more constructive and actionable.
Value articulation
Where did you connect your message well to something the buyer already cared about, and where did you lose that connection?
I use this question to assess whether the rep shaped the message around what mattered to the buyer, rather than simply delivering a general company narrative.
Where did you describe features when you should have focused on outcomes?
A practical way to spot where the message stayed too tied to the product and did not translate far enough into customer value.
What part of your message felt most relevant, and what part felt generic?
This question helps the rep notice where the message landed well and where it may have sounded too broad or interchangeable.
How well did you explain why your solution matters in this buyer’s context, specifically?
A strong question for sharpening relevance and making sure the rep is not relying on value language that could apply to almost anyone.
If the customer had to repeat your value back to a colleague, what would they say?
I like this question because it tests whether the message was clear, memorable, and strong enough to travel internally.
Negotiation
What was the customer trying to protect in that negotiation?
This question helps the rep read the negotiation more thoughtfully, rather than seeing it only as pressure on price or terms.
Where did you give ground too quickly?
A strong question for identifying moments where the rep conceded before they really needed to.
What did you trade, and what did you get in return?
This question helps the rep think more clearly about whether the negotiation was handled as a true exchange.
Where did you protect value well, and where did you give up too much too easily?
A useful way to review balance in the negotiation without reducing the conversation to win or lose.
What would you do differently next time to slow the moment down and negotiate with more control?
This question supports the rep in turning the reflection into a more deliberate set of actions within the realm of negotiation.
Closing
What signs told you the customer was ready, or not ready, to move forward?
I like this question because it focuses on judgement and reading between the lines, not just whether the rep asked for something at the end.
What made your ask for the next step clear, or unclear?
A simple question that helps the rep assess whether the close was easy to understand and act on.
Where did you hesitate to create commitment?
A useful question when the rep had enough momentum to ask clearly, but held back in the moment.
What made the close feel natural, or feel forced?
This question helps the rep think deeper about timing, fit, and flow, rather than relying on rehearsed closing lines. Customers pay attention to minor details like this, even when they themselves do not realise it.
What specific commitment should you have left the conversation with?
A good way to check whether the rep is clear on what the close actually needed to achieve in that situation.
Developmental coaching questions
Developmental coaching focuses less on a specific deal or skill gap and more on the person behind the performance.
It looks at confidence, emotional patterns, beliefs, and other internal factors that shape how a rep shows up and makes decisions.
In many ways, this is the most traditional form of coaching, and often the hardest to do well. I say this because it requires the coach to step back and remove themselves from the equation, so the rep can reflect on their own thinking rather than being guided towards a specific answer.
Rather than focusing on technique or deal mechanics, the aim is to surface what may be holding the rep back and support them in shifting how they think, respond, and act over time.
Self-awareness and internal patterns
What do you think you do especially well in your role, and where do you think you hold yourself back?
I believe this is a strong developmental question because it opens up reflection in a balanced way. The rep is invited to notice both strengths and constraints and reflect deeper on them.
What situations tend to bring out your best performance?
A useful question for identifying the conditions that help the rep perform at their best more consistently.
What do you notice about how you respond under pressure?
This question invites the rep to start noticing how they react in high-pressure moments, even if they have not reflected on it before.
Where do you think you’re judging yourself fairly, and where might you be misreading things?
Use this one to help the rep reflect on how they see themselves, and where that view might not fully match reality.
What are you feeling right now that may be affecting how you show up?
This question encourages the rep to gain insights into what may be shaping their behaviour beneath the surface, rather than staying only at the level of action.
Where do frustration, fear, or defensiveness tend to show up in your work?
A useful question when certain emotional responses seem to be affecting execution, judgement, or relationships.
What usually happens after one bad call, one setback, or one rejection?
This helps the rep reflect on what happens after the difficult moment, which is often where important patterns become visible.
Confidence, hesitation, and avoidance
Where are you hesitating right now, even though you probably know what needs to happen?
I like this question because it helps distinguish uncertainty from avoidance. Often, the rep already knows the right move, but something is making it harder to act on it.
What part of this situation feels most uncomfortable for you, and why?
A strong question for surfacing what the rep may be avoiding, rather than circling it indirectly.
When your confidence drops, what tends to trigger it?
This question is aimed at helping the rep connect the dots between the internal world and external world as it relates to self-confidence.
What would acting with more conviction look like in this situation?
A strong way to help turn confidence into something more observable and practical, rather than leaving it as a vague internal state.
What feels risky to you about acting more directly in this situation?
A helpful question when hesitation is really about perceived risk. It can uncover fears that are driving inaction more than the rep realises.
Beliefs, assumptions, and perspectives
What story are you telling yourself about this situation?
One of the most powerful questions in developmental coaching. We often take our internal narrative as given, but bringing awareness to it gives the rep a chance to question it and, if needed, reshape how they see the situation.
What are you assuming that may not actually be true?
Simple, but powerful. Such a question helps the rep separate unsupported interpretation from fact.
Where might a limiting belief be shaping your behaviour more than you realise?
A strong question when the rep seems stuck in a pattern that does not fully match their actual capability or potential.
If someone else looked at this situation more objectively, what might they see differently?
A good way to loosen the grip of internal certainty and create a bit more perspective.
What belief or interpretation here is helping you least?
I like this because it makes the internal lens more visible. It helps the rep notice not just what they believe, but whether that belief is actually serving them.
Motivation and growth
What kind of growth matters most to you right now?
Use this question to connect coaching to something more meaningful than short-term goals or performance pressure.
What is energising you at the moment, and what is draining you?
A helpful question when motivation feels uneven, inconsistent, or fragile.
What would progress look like for you over the next few months, beyond just hitting the target?
This question broadens the conversation from output to development, which is often where more impactful coaching begins.
What do you need to change, practise, or let go of to grow from here?
A strong closing question because it turns reflection into something more deliberate and developmental.
What is one shift you know would make a real difference, if you followed through on it consistently?
I like this as another type of closing question because it helps turn a broad coaching conversation into one clear development priority.
Turn sales call insights into revenue-driving action
Most common mistakes sales managers make when coaching
Over the years, I’ve observed many managers run coaching conversations across different contexts, teams, and levels of experience.
In most cases, the issue is not the manager’s willingness to help. It is the way the question is framed, the moment it is asked, or the purpose it ends up serving in the conversation.
Below are some of the most common mistakes I’ve seen.
1. Asking leading questions that already contain the answer
This is one of the most common ones.
The manager asks something that sounds like a question, but is really a disguised conclusion:
“Don’t you think you should have pushed harder there?”
“Wouldn’t it have been better to go back to value?”
At that point, the rep is trying to work out what the manager wants them to say instead of thinking freely.
That dynamic of interaction will inevitably reduce reflection and weaken ownership on the sales rep side.
2. Jumping to advice too early
This usually happens when the manager sees the issue quickly and wants to be helpful.
But if advice comes before the rep has properly examined the situation, the learning stays shallow.
The rep may nod, agree, and even follow the suggestion, but they have not really done the thinking themselves. Once again, this reduces ownership and forward commitment.
I’ve seen this happen often in deal coaching, where the manager jumps from a few surface details straight into “what I would do”. Sometimes advice is needed, of course, but when it comes too early, it cuts off the reflection that coaching is meant to elicit.
3. Approaching coaching like inspection
This is especially prominent in sales environments.
A manager asks questions that appear relevant, but are really just checking compliance:
“Did you fill in MEDDPICC (or whichever sales methodology your organisation uses)?”
“Did you ask about the budget?”
“Did you send the follow-up?”
There is nothing inherently wrong with these questions. In some situations, they are necessary.
The issue is when they become the default mode of coaching.
On their own, they do not help the rep think more clearly. They simply confirm whether a step was completed or not.
They only become coaching questions if they are used to go further, for example, to explore why something was done (or not), what the rep learned from it, and what they would approach differently next time.
When reps feel they are being inspected rather than coached, the dynamic shifts. They become more cautious, more focused on saying the “right” thing, and less willing to share what is actually going on.
And once that happens, the quality of the coaching conversation drops significantly.
4. Asking questions that do not fit the coaching moment
Some questions sound smart in isolation, but land flat because they do not match the situation.
For example, asking a broad self-reflection question when the rep is trying to think through a live deal. Or asking a pipeline question when the real issue is confidence or hesitation.
I’ve seen managers use the same two or three favourite questions in every coaching conversation, regardless of what is actually going on. That usually leads to surface-level answers, because the question is not connected enough to the real coaching job.
5. Asking too many questions without creating direction
This is a less obvious mistake, but a very common one.
Sometimes the manager asks several thoughtful questions in a row, but each one goes in a slightly different direction. The conversation becomes broad, but not deep.
Instead of probing and building on a specific line of thinking, the manager keeps moving on to the next question. As a result, the rep reflects on multiple things, but nothing is explored far enough to become truly useful.
I’ve seen this happen often when managers try to “cover everything” in one coaching session. The intent is good, but the outcome is not.
At some point, coaching needs focus. It needs to stay with one area long enough to create clarity, challenge assumptions, and work towards a more concrete shift.
Otherwise, the rep leaves with a handful of observations, but no clear direction on what to do differently.
Good coaching questions should not just open up thinking. They should also help narrow it, so the conversation leads to a small number of meaningful actions.
6. Ending without a commitment or next step
Continuing from the previous mistake, ending without some sort of commitment or next step is where many coaching conversations lose their effectiveness.
The rep may leave with more awareness, a better perspective, or a clearer understanding of the issue, but nothing has been translated into action.
And awareness, despite being an essential ingredient for behavioural change to occur, may not be sufficient on its own.
I often see this happen when the conversation stays reflective, but never quite moves into “what will you do differently now?” Without that shift, the insight remains interesting, but not particularly useful.
What ultimately matters is whether the conversation leads to a meaningful change: a decision, a new approach, or a clear next step the rep is committed to following through on.
Conclusion
The real value of a coaching question is in what it helps the rep notice, reconsider, and act on.
The right set of questions can surface a blind spot in a deal, challenge a weak assumption, clarify what matters most, or help someone see their own patterns more clearly.
This is also why context matters so much.
Strong managers are clear on what they are trying to achieve in the conversation. They do not reach for questions at random or rely on the same few every time.
They match the question to the coaching moment, then listen closely enough to turn the answer into something useful.
In the end, that is what separates routine “coaching” from coaching that actually drives change.
Not more questions.
Better ones.
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