The New Sales Leader's Diagnostic: 20 Questions to Ask Before You Change Anything
- Gemma Sole
- Oct 27
- 3 min read
How to Learn What’s Really Happening on the Floor
When you step into a new sales leadership role, your first instinct is to look at dashboards — pipeline coverage, win rates, activity metrics. But those numbers only tell you what’s happening, not why.
That’s where structured seller interviews come in.
These questions help you uncover how your team actually sells, what they believe drives success, and where the real friction lives — long before you start rewriting playbooks or processes.
Run them as 20–30 minute 1:1s with a cross-section of your reps (top, mid, and underperformers). Record responses if possible — patterns will tell you more than any single answer.
🔎 Discovery Questions (Understanding the Rep’s World)
What part of the sales process feels most predictable for you?
Where do deals most often stall or die, and why do you think that happens?
If you had to coach a new rep on “how to win here,” what would you tell them to focus on?
What’s one part of our process that slows you down or adds no value?
How do you personally prepare for a discovery call or demo?
🎯 Playbook & Messaging Questions
Which parts of our sales playbook or messaging help you the most?
Which parts feel outdated, repetitive, or irrelevant to your actual deals?
When you lose a deal, what do you hear most often from the buyer?
What part of the product story do prospects light up about?
What’s the hardest objection for you to handle today?
🤝 Coaching & Enablement Questions
How often do you get structured feedback on your calls?
What type of feedback helps you improve fastest — written notes, 1:1 reviews, or examples?
How do you currently track whether your own selling is improving week over week?
What’s one skill or behavior you wish you had more coaching on?
How do you define a “great” sales call in your own words?
🧭 Strategy & Alignment Questions
What do you think differentiates us most in the market?
Do you feel our current sales strategy matches what you hear in the field?
How confident are you in forecasting your deals — and what makes it hard?
Where do you feel disconnected between Sales, Marketing, and Customer Success?
If you could fix one thing about how we sell, what would it be?
Pro Tip: How to Use the Answers
Look for alignment gaps. Are top reps saying the same things as the middle performers? If not, your playbook isn’t grounded in real behaviors.
Spot quick wins. Common friction points (e.g., “demo flow too long”) often surface across reps.
Update your coaching plan. Each rep’s answers point directly to coaching needs — use them to prioritize training or refine your scorecard.
Feed insights back into AI tools. The most effective Knode users upload these insights to refine what “good” looks like faster.
Turn Answers into Action
A great sales strategy starts with curiosity. Use these questions to listen deeply, define reality, and build the trust you’ll need before changing anything. While this list is a strong starting point, you'll likely uncover other questions specific to your product, market, and unique situation.
Once you’ve heard your sellers’ truths, the data will finally make sense.
But listening is just the first step. These seller interviews are the foundation for your entire coaching strategy and a critical action in your first 30 days. They're how you move from knowing what's happening to understanding why.
To see exactly how to use these answers, and how they fit into a complete 90-day plan —from auditing your playbook to building AI-powered scorecards and establishing a weekly coaching rhythm — download our full guide.
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