Short answer: The best coaching questions are discovery questions pointed at the rep. Ask: What is the biggest challenge in your pipeline right now? What happens if we do not address it? What are you doing about it today? What would solving it mean for you? When do you want to see it solved? Then ask: Who else could help? These questions run in step 5 of the 9-step sales coaching conversation, after you have named the issue and before you propose your own ideas.
Why use discovery questions in a coaching conversation?
Reps often see causes you cannot see from the dashboard. A connect rate drop might be a list problem, a time-of-day problem, or a confidence problem, and the rep usually knows which. Asking first gets you a better diagnosis, and it makes the rep part of the solution, which makes the plan in step 7 theirs.
The 5 Magic Questions help you connect with anyone, not just prospective customers, but your people as well! A coaching conversation is a discovery conversation about the rep's own business.
What are the best coaching questions to ask a sales rep?
1. What is the biggest challenge in your pipeline right now?
Start broad. You named the issue in step 4. This question checks whether the rep sees the same issue, or a different one that is upstream of it.
2. What happens if we do not address it?
This connects the issue to its consequence in the rep's own words: a missed number, a smaller commission check, a slower path to promotion. It is the rep's version of the downstream consequence you named in step 4.
3. What are you doing about it today?
This tells you what has been tried and what has not. It also surfaces effort you might not have seen.
4. What would solving it mean for you?
This ties the fix to the rep's personal goal: hitting quota, the next role, a better quarter. It is the same reason a buyer's champion acts: there is a personal win at the end.
5. When do you want to see it solved?
Let the rep propose the time frame. Then agree it in step 7, along with the check-in tempo.
Bonus: Who else could help?
A peer who is strong at the skill, an AE partner, enablement, or you. Ask it last, once the rep owns the issue.
Want your managers asking better questions?
I train frontline leaders to run discovery with their reps the way the best sellers run it with buyers.
How do the questions change for SDRs and AEs?
| Question | SDR version | AE version |
|---|---|---|
| 1. Biggest challenge | "What is making it hard to turn connects into meetings right now?" | "Which deals worry you most this quarter, and why?" |
| 2. If not addressed | "What does that do to your pipeline number this month?" | "What does that do to your forecast?" |
| 3. Doing today | "What have you changed in your talk track or list so far?" | "What is your next step on each of those deals?" |
| 4. What solving means | "What would hitting your pipeline number mean for your path to AE?" | "What would closing those deals mean for your quarter?" |
| 5. Timeline | "By our next 1:1, what would you want to see move?" | "Which deals need to advance by end of month?" |
For the metrics behind each version, see The SDR Leader 1:1 and The AE Leader 1:1.
When should a manager share their own view?
After the rep has answered. Step 6 of the conversation is where you propose what you think is causing the issue and where you can help. Going second means you can build on the rep's diagnosis instead of replacing it, and you will often find the rep has already named half the answer.
Frequently asked questions
What questions should a sales manager ask in a coaching session?
What is the biggest challenge in your pipeline right now? What happens if we do not address it? What are you doing about it today? What would solving it mean for you? When do you want to see it solved? Who else could help?
Should a sales manager ask questions or give answers in coaching?
Ask first, then share your view. The rep's answers improve the diagnosis and make the rep the owner of the plan.
How do you get a sales rep to open up in a coaching conversation?
Open with a specific positive, remind them the goal is their success, and ask open questions about their pipeline before offering your own view.
Related
Want to bring discovery into your team's coaching?
Book time and we will adapt these questions to your team's motion and metrics.