High-Impact Discovery Questions for Selling to Learning & Development Leaders

Summary:

In SaaS companies, the Head of Learning & Development carries the responsibility of building continuous learning cultures, upskilling teams quickly, and proving ROI on training investments. They often struggle with low adoption of learning platforms, fragmented knowledge sharing, and limited visibility into the business impact of coaching. Effective discovery with L&D leaders means connecting your tool to their goals, boosting performance, improving engagement, and making learning measurable.

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Here’s a curated set of 30 discovery questions spanning early discovery, qualification, and deep needs analysis designed to resonate with L&D leaders in SaaS.

Early Discovery (Understand context + hook interest)

How does your team currently deliver learning and coaching across the organization?
What are the biggest challenges you face in driving adoption of your training programs?
How do you measure the success of your current L&D initiatives?
What tools or platforms are you using today for training and coaching?
How aligned are your L&D goals with overall business objectives like sales growth or customer retention?
What skills gaps are you currently prioritizing within your SaaS teams?
How do you ensure training programs are relevant and role-specific?
What role does manager-led coaching play in your learning strategy?
How do you handle onboarding for new employees in fast-scaling teams?
What are your biggest frustrations with your current L&D setup?

Qualification (Uncover priorities, buying signals)

Which metrics matter most for your L&D strategy, engagement, completion rates, performance impact, or employee retention?
How do you track ROI on learning and coaching programs today?
Who in your leadership team typically sponsors L&D investments—CPO, CRO, or CEO?
How often do you revisit or redesign your learning programs?
What’s your current budget allocation for L&D tools and platforms?
Are you actively exploring new coaching or learning technologies this year?
What are the gaps in your current learning technology stack?
How important is integration with tools like Slack, Salesforce, or HR systems for you?
How do you handle personalization of learning at scale?
If you continue with your current L&D tools, what limitations or risks do you foresee?

Deep Needs Analysis (Tie value to goals, quantify pain)

How do you measure the direct impact of training on business performance?
What’s the average adoption rate of your current learning programs?
How much time does your team spend manually tracking learning progress?
What challenges do managers face in providing consistent coaching?
How do you identify and close skills gaps across different teams?
What’s the impact of poor onboarding on your time-to-productivity metrics?
How often do employees request learning support outside of structured programs?
How would improving coaching consistency affect sales or customer success performance?
How do you gather employee feedback on training effectiveness?
If you could automate one aspect of your L&D process—content delivery, coaching, or reporting, which would you prioritize?

How Pepsales AI (or an L&D Coaching Tool) Makes Discovery Smarter

AI-powered coaching tools transform the way L&D leaders deliver value. Instead of generic training, your teams get role-specific, just-in-time coaching embedded into daily workflows. With built-in analytics and automation, you can directly link learning to performance outcomes.

What You Get:

Real-time, contextual coaching embedded in SaaS workflows
Automated progress tracking and reporting tied to business KPIs
Personalized learning paths to improve adoption and engagement
Measurable impact of training on sales performance and retention

This isn’t just another LMS, it’s your coaching engine for SaaS scale-ups.

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Want to Drive Higher Engagement & Measurable Impact?

‍Equip your L&D team with AI-powered coaching that connects learning to outcomes. Get Early Access to the Pepsales AI Copilot