Question Strategy & Curiosity Playbook
Analyses questioning behaviour to determine whether reps use open-ended, insight-driven questions that deepen understanding. Measures follow-up depth, listening behaviour, and interruption patterns to improve conversational quality.
Start building
Deploy this kit stack into your workspace. Customize bricks, scoring, and outputs to match your team.
Without this playbook
Most teams handle question strategy & curiosity through scattered call reviews, manager opinion, and isolated examples. Without a shared operational definition, the signals stay inconsistent and difficult to act on across volume.
With this playbook
A shared, repeatable lens for question strategy & curiosity - with structured outputs you can route into coaching, reporting, and workflow automation. Every conversation produces evidence, not just opinions.
Built for
Sales managers, enablement leads, and frontline coaches
When teams use it
- Coaching sessions and 1:1 reviews
- Rep skill development tracking
- QBR preparation and team benchmarking
The operational stack
1 kit behind this playbook
Asking questions and actually listening to the answers are two different capabilities. This stack measures both - whether the rep is asking the kind of open-ended, layered questions that create insight, and whether they are listening well enough to build on what they hear. Reps who score well on questioning but poorly on listening are interrogating, not discovering. You need both signals to coach effectively.
Listening & Response Kit
4 bricks
Tracks listening behaviour and substantive follow-ups.
Included bricks
Customize this kitTalk Ratio Score
ScoreMeasures how much each speaker talks rep versus customer
Open Vs Closed Question Ratio
BooleanScores ratio of open versus closed questions asked
Active Listening Signal Present
BooleanDetects active listening cues acknowledgements and paraphrasing
Interruptions Present
BooleanDetects interruptions that break effective listening
Knowledge base
Supporting materials
The kits in this playbook work best when backed by reference materials that ground the evaluation. Upload these into your workspace knowledge base to improve accuracy and relevance.
Learn more about Knowledge BasesQuestioning framework documentation (e.g. SPIN, Sandler, Challenger)
Examples of high-quality open-ended questions by deal stage
Internal coaching rubrics for conversational quality
Recorded call libraries with annotated questioning sequences
Talk ratio and listening behaviour benchmarks
Structured output
What you get back
Every conversation processed through this stack produces a structured JSON object. Each brick contributes a typed field - booleans, scores, categories, or string lists - that you can route, aggregate, and report on.
Example output shape
{
"talk_ratio_score": 7,
"open_vs_closed_question_ratio": true,
"active_listening_signal_present": true,
"interruptions_present": true
}In practice
How teams use these outputs
The structured outputs from this stack integrate into your existing workflows. Use them wherever you need repeatable, evidence-based signal from conversations.
Coaching sessions and 1:1 reviews
Rep skill development tracking
QBR preparation and team benchmarking
Enablement program measurement
Get started
Deploy this playbook in your workspace
Customizing creates a workspace-owned draft with this playbook's full kit stack. Adjust bricks, scoring, and outputs to fit your team, then publish when ready.