High-Impact Discovery Questions for Selling to Sales Enablement Leaders in SaaS

Summary:

Uncover onboarding friction, align with productivity goals, and show coaching impact with questions tailored for Enablement Leaders in fast-growing SaaS teams.
Sales Enablement and L&D leaders are under pressure to ramp reps faster, increase quota attainment, and improve coaching at scale. If you sell L&D or Coaching tools, the right discovery questions can surface real training gaps and prove the ROI of continuous enablement.

‍

Here’s a ready-to-use set of 30 questions ideal for uncovering enablement pain points and building urgency for adoption.

Early Discovery (Understand context + hook interest)

What are your top enablement or L&D goals this quarter?
How do you currently track rep ramp time and onboarding outcomes?
What challenges do you face delivering consistent training across teams?
How do you support sales managers with coaching resources?
What tools are reps using today to prepare for calls or demos?
Where do you see the most knowledge gaps after onboarding?
Are your coaching efforts aligned with actual sales outcomes?
How do you currently measure training effectiveness?
What’s your approach to scaling enablement across new hires and tenured reps?
How do you keep reps up to speed when messaging or product updates happen?

Qualification (Uncover priorities, buying signals)

What would a successful enablement tool need to deliver for you?
Are you tracking metrics like time-to-first-deal or quota attainment post-training?
How do you prioritize which skills or behaviors to coach?
Who’s typically involved in buying or implementing enablement tools?
Are you considering any other platforms to support coaching or L&D?
How are frontline managers involved in your training initiatives?
What existing tools or systems would you need this to integrate with?
Is there a budget currently allocated to coaching or enablement?
What’s currently holding your team back from stronger rep performance?
What’s your timeline for solving this?

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

How long does it take for a new rep to reach full productivity?
How confident are you that reps are applying training on real calls?
What’s the cost of poor discovery or unqualified deals on your pipeline?
How much time is spent manually reviewing rep calls or activity?
How do you assess whether managers are coaching effectively?
What’s the impact of missed coaching moments on quota attainment?
How often do reps need to relearn core concepts post-onboarding?
What would a 10% boost in team-wide win rate mean for your org?
What gaps exist between enablement insights and sales execution?
If you could automate one part of the training or coaching process, what would it be?

How Pepsales AI Helps

‍

Pepsales AI helps sales teams ask the right questions, faster. It delivers intelligent, role-specific, and industry-aware discovery questions in real time tailored to the context of each deal.

What it delivers:

A library of proven questions per industry, persona, and product
Smart prompts that adapt to buyer role, objections, and stage
Embedded coaching and insights to guide better conversations
Automation of discovery prep—no more guesswork

Whether you’re prepping for a demo or coaching new reps, Pepsales AI ensures every conversation starts strong and gets to the real need, fast.

Ready to unlock higher-quality discovery conversations?

‍

Get Early Access to the Pepsales AI Discovery Copilot
Equip your team with questions that uncover real problems, build urgency, and close more deals.