High-Impact Discovery Questions for Selling to Enablement Leaders in EdTech
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Summary:
Understand onboarding challenges, align with adoption goals, and position your solution as a driver of rep productivity in a fast-paced academic tech environment.
In EdTech, enablement leaders are often juggling fast rep ramping, evolving product messaging, and seasonal sales cycles. Discovery done right helps position your SalesTech platform as essential infrastructure. Use these 30 questions across the sales conversation to get to real problems quickly.
Here’s a curated set of 30 discovery questions spanning early discovery, qualification, and deep needs analysis, perfect for tools focused on pipeline visibility, onboarding, and compliance coaching.
Early Discovery (Understand context + hook interest)
- What are your biggest enablement priorities during this enrollment cycle?
- What challenges are you seeing in rep ramp-up or knowledge retention?
- How are you tracking rep activity across different segments (K-12, higher ed, etc.)?
- What part of your sales process feels the most inconsistent across teams?
- How confident are you in your current sales messaging alignment?
- Are you facing challenges training reps on new curriculum or platform changes?
- How do you currently deliver playbooks or content to your reps?
- Do your reps get structured coaching on calls or demos?
- What tools do you use to support asynchronous learning and coaching?
- How do you keep distributed campus sales teams aligned?
Qualification (Uncover priorities, buying signals)
- How do you measure success for your enablement programs?
- What key metrics (adoption, speed-to-ramp, win rates) do you want to improve?
- What would justify switching to a new enablement solution?
- Who else in your org typically signs off on enablement tools?
- What’s your timeline for rolling out a solution across teams?
- Have you tried other coaching or LMS platforms before?
- How important is real-time feedback during live calls or demos?
- Are there budget constraints tied to the academic calendar?
- What internal challenges have blocked enablement improvements in the past?
- Are any upcoming initiatives (new GTM, curriculum, partners) driving urgency?
Deep Needs Analysis (Tie value to goals, quantify pain)
- How do you track rep knowledge on newly launched programs?
- What’s the impact of unprepared reps on school/district deal outcomes?
- How do you identify gaps in how reps position your product?
- What’s your average ramp time for a new academic sales rep?
- How often do you update your content or playbooks?
- How do you ensure reps apply what they learn in real calls?
- What time is lost chasing alignment across marketing, product, and sales?
- What would a 10–15% bump in close rates mean for your territory this season?
- What’s the cost of losing a qualified school district deal due to poor positioning?
- If you could automate one aspect of rep prep, what would it be?
How Pepsales AI Makes Discovery Smarter
Pepsales AI empowers your sales team to ask the right questions, faster and more effectively. It delivers intelligent, role-specific, and industry-aware discovery questions in real time tailored to the context of each deal.
What You Get:
- A ready-to-use library of proven questions by persona, industry, and product
- Smart, dynamic prompts that adapt to objections, buyer roles, and sales stages
- Built-in coaching to help reps lead more impactful conversations
- Automated prep, no more guesswork before discovery calls
Whether you're gearing up for a demo or onboarding new reps, Pepsales AI helps every conversation start strong and go deeper, faster.
