10 Questions to Ask Your Sales Team

The questions

Open any question to see why it works.

1. 1

   What are you most excited about in your pipeline right now?

   Opening with a win gets a rep 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.

2. 2

   Which deal are you most worried about, and what specifically worries you?

   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.

3. 3

   What did a customer say this week that stuck with you?

   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.

4. 4

   What is the most common objection you are hearing, and what do you say back?

   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.

5. 5

   Which competitor is showing up most in your deals, and what are they claiming about us?

   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.

6. 6

   Where is your pipeline thinnest right now: this month, next quarter, or the top of the funnel?

   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.

7. 7

   Which prospecting activity is producing meetings right now, and which one has gone dead?

   Sequences, events, and referral paths decay quietly, and the rep working them daily notices weeks before the reporting does. The dead channel is usually still consuming a third of their week.

8. 8

   On your largest open deal, who actually signs, and have you spoken with them yourself?

   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.

9. 9

   Why would that customer buy now instead of six months from now?

   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.

10. 10

    What do you need from me this week to move one specific deal forward?

    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.

11. 11

    Which step in our sales process do you skip or work around?

    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.

12. 12

    What are we promising in the pitch that the product does not quite deliver?

    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.

13. 13

    At which stage are you losing the most deals, and what tends to happen right before you lose them?

    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.

14. 14

    What do we discount for most often, and would we still win those deals at list price?

    Habitual discounting is usually a symptom of weak value framing or late stage panic rather than genuine price sensitivity. Asking whether the deal survives at list forces the rep to say out loud what the concession actually bought.

15. 15

    Which of your existing accounts could be twice the size, and what is blocking that?

    Expansion revenue is cheaper than new logos and 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.

16. 16

    Do you believe your number this quarter, and what has to be true for you to hit 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.

17. 17

    Think of a deal you called committed that slipped. What did you miss at the time?

    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.

18. 18

    What one skill would make the biggest difference to your numbers, and how would you want to build it?

    Self diagnosis produces development plans people actually follow, and the answer often differs from what you would have assigned. Asking how they want to build it surfaces whether they need reps, examples, or your presence on a call.

19. 19

    Does the comp plan push you toward the deals we actually want to win? Where does it not?

    Compensation quietly overrides strategy, and reps can describe the exact deals the plan makes irrational to pursue. This is a question most managers avoid, which is why the misalignment persists for years.

20. 20

    What are you not telling me because you think I will not want to hear it?

    Ask this last, 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.