The Win-Loss Playbook: Questions, Timing, and Who Should Lead the Call

If you want to improve your close rate, tighten your sales messaging, and better understand your buyer, there’s no faster path than a structured win-loss call process.

And yet, very few professional services firms do it well (or at all).

This playbook will show you exactly how to run win-loss calls that generate real insight.

We’ll break down:

• When to schedule the call
• Who should lead it
• What questions to ask
• How to act on what you hear

Why Win-Loss Calls Matter in Professional Services

Unlike product led companies with usage data and NPS tools, service firms often fly blind. We rely on anecdotal feedback from salespeople, or worse, we assume we know why a deal was won or lost.

Win loss calls provide direct buyer feedback. The gold standard for understanding how your firm is perceived and where your process breaks down.

Done right, these calls uncover:

• Misalignments between marketing, sales, and delivery
• Messaging that confused or missed the mark
• Competitor strengths you’re underestimating
• Sales rep behaviors that help, or hurt your chances

When to Run a Win-Loss Call

Timing matters. Here’s a simple rule of thumb:

• Win Calls: Within 7 days of contract signing
• Loss Calls: Within 3–5 days of the “no”

Too soon, and the buyer may not have processed the decision. Too late, and it becomes awkward or irrelevant.

Set up the call while emotions (and memory) are still fresh. Position it as a quick, non-salesy conversation to help you improve.

Who Should Run the Call?

Not the salesperson. And not someone trying to “save the deal.”

Instead, assign:

• A founder or senior leader (if the deal was strategic)
• A sales operations leader
• A client experience/insights lead
• A neutral third party (in some cases)

The goal is to remove pressure and encourage honesty. Make it clear the rep won’t be penalized for the outcome and this is for learning only.

Questions to Ask (With Real Phrasing)

Keep it simple, short (15–20 minutes), and conversational. You’re listening more than talking.

Here’s a simple script:

Intro:

“Thank you again for taking this call. This is not a sales conversation we’ve closed the books on this deal. We’re just trying to get better and would really value your candid thoughts.”

7 Questions:

1. “What stood out to you good or bad about our firm during your evaluation?”
   (Start open-ended to get their gut reaction.)
2. “What other firms were you considering?”
   (You’ll often get the real competitive set, which is different from what you assume.)
3. “What ultimately tipped the scales in your decision?”
   (This reveals the real decision drivers: risk, trust, price, timing, politics.)
4. “How did our pricing compare, and how did you perceive the value?”
   (Uncovers whether your pricing model is working—or feels random.)
5. “Did anything in our sales process create friction or confusion?”
   (Great for process and messaging improvements.)
6. “If you could change one thing about our approach, what would it be?”
   (Signals positioning blind spots.)
7. “Would you be open to us reaching out again in the future?”
   (For losses, this determines if it’s truly dead or just bad timing.)
8. “If you were running our process yourself, how would you have positioned us differently”
   (Surfaces how the buyer perceives your process didn’t land. Great for refinement.)

What to Do With the Feedback

Here’s where most firms fail, they gather intel but never close the loop.

Build a simple system:

• Tag the feedback in your CRM under “Win-Loss Insight”
• Share patterns monthly in your sales meetings
• Translate insights into changes in:
  • Talk tracks
  • Proposal structure
  • Sales enablement materials
  • Ideal Client Profile targeting

And remember.. don’t weaponize the feedback. This isn’t about blaming reps, it’s about improving the system.

Win / Loss Template to Use:

Deal Information

• Client/Company Name:
• Primary Contact Name + Title:
• Opportunity Value:
• Service Line / Offering Discussed:
• Date of Decision:
• Call Date:
• Deal Owner (Sales Rep):
• Call Conducted By:

Summary of Call (Key Insights)

1. Final Decision:
2. Primary Reason for Decision
3. Competitive Landscape
4. Buying Criteria Insight
5. Pricing Perception
6. Sales Process Feedback
7. Positioning Feedback
8. Future Opportunity

Final Thought: Don’t Let Feedback Die in Silence

If you’re serious about improving sales performance, win-loss calls are the single highest ROI feedback loop you can create. They’re cheap, fast, and brutally honest.

And in professional services, where trust is everything, that honesty is your most valuable sales asset.