31 Win Loss Analysis Survey Questions to Boost Sales Success

Lost Deal Post-Mortem Survey

Why & When to Use

A lost deal survey isn’t about licking wounds or assigning blame—it’s your reality check to learn, adapt, and eventually steal back the win. Within days of a lost deal, send your survey to get buyers’ raw impressions before memories fade into polite afterthoughts. These insights are invaluable if you want to address pitfalls and improve.

Your survey will uncover:

• Real reasons behind lost opportunities: Was it price, a missing feature, or something else?
• Bottlenecks in your sales process and when things started to go sideways.
• The criteria and “tipping point” that led to a competitor winning.
• Buyer feedback that goes beyond anecdotes by collecting quantitative and qualitative data.
• Solid competitive loss reasons to guide your future strategy.

Taking action on lost deal insights can be transformative—revisit your proposal templates, tweak pricing, or prioritize that one missing feature that’s losing you deals.

5 Sample Questions to Include

1. What was the primary reason you ultimately chose another solution?

2. Which feature, service, or price point did the winning vendor offer that we did not?

3. How would you rate the relevance of our proposal to your business challenge?

4. At what stage did we fall behind competitors in your evaluation?

5. What could we have done differently to earn your business?

Don’t just file the feedback away—share highlights in retrospectives and sales enablement sessions. That’s how you turn lost deals into future wins.

A study by the Win Loss Agency found that 60% of lost deals are due to misalignment between the vendor's offering and the buyer's needs. Source

Competitor Displacement Survey (Deals Won Back from a Competitor)

Why & When to Use

Winning an account back from a competitor is like taking back your lunch money—and you’ll want to understand exactly how you did it. The competitor displacement survey is sent to customers who have recently switched to your solution after using a rival. Timing is crucial: reach out while the switch is new, when emotions and reasoning are still vivid.

The goals here are juicy:

• Validate which of your differentiators most compelled the buyer to make the jump.
• Diagnose your competitors’ weaknesses straight from the customer’s mouth.
• Learn which elements of your messaging and onboarding helped seal the deal.
• Build a playbook for competitive “take-out” campaigns using fresh data.
• Empathize with switching pains, so you can make the transition delightfully smooth.

Feed this feedback to your product and marketing teams ASAP—you’ll want to capitalize on “switchers’” motivations in your outreach and future campaigns.

5 Sample Questions to Include

1. What shortcomings did you experience with the previous vendor that prompted the change?

2. Which of our differentiators was most compelling in your decision to switch?

3. How did implementation or onboarding influence your confidence in moving away from the competitor?

4. Which stakeholders championed the switch internally and why?

5. What could the previous vendor have done to retain your business?

This survey turns your competitive intelligence into a practical toolkit for unseating rivals—and makes for a few satisfying internal high-fives, too.

Renewal & Churn-Prevention Survey (Post-Purchase Loss Insight)

Why & When to Use

Whether customers are renewing, expanding, or walking away, the renewal and churn-prevention survey sheds light on what keeps them loyal—or pushes them out the door. Surveying your customers at contract renewal or cancellation is more than a retention formality. It gives you actionable signals for customer success and future expansion.

This survey only works if it’s well-timed and honest:

• Right after the renewal or churn decision is when drivers and triggers are clear in buyers’ minds.
• Ask about accomplishments and outcomes, not just satisfaction scores.
• Tap into expansion readiness or surface threats before they metastasize.
• Gather buyer feedback that reveals product strengths and gaps.
• Benchmark your own team’s responsiveness and reliability—with unfiltered honesty.

Armed with these insights, your product and customer success teams can build meaningful strategies for boosting loyalty and preventing churn before it starts.

5 Sample Questions to Include

1. What key outcomes did you achieve—or fail to achieve—since adopting our solution?

2. Which features deliver the greatest ongoing value to your team?

3. How satisfied are you with support responsiveness and expertise?

4. If you considered canceling, what factors influenced that consideration?

5. What additional capabilities would strengthen your loyalty going forward?

Survey results should feed into your customer success playbooks and inform product enhancements. Don’t hide tough feedback—address it directly and move the needle.

A study found that the propensity to churn increases when friends do, especially when many strong friends churn, suggesting that churn managers should consider strategies aimed at preventing group churn. (arxiv.org)

Sales Process Feedback Survey (Buyer Journey Friction Points)

Why & When to Use

Every buyer’s journey, whether ending in a win or loss, offers a treasure trove of lessons about your sales process. A sales process feedback survey is deployed to both won and lost prospects to uncover friction points unrelated to product. Think of this as the backstage pass to the show that is your buyer’s experience.

Why send it?

• Pinpoint issues like confusing demos, disconnected proposals, or slow follow-ups.
• Isolate where your process shines and where it falters, regardless of win/loss.
• Gather buyer feedback on communication, decision-maker engagement, and resourcefulness.
• Use anonymous input to foster continuous improvement, not blame games.
• Tailor your enablement and training to address the highest-leverage gaps.

Continuous improvement is impossible without a candid view into your buyer journey. This survey hands you a roadmap, so you’re not just guessing where to get better.

5 Sample Questions to Include

1. How clear was our articulation of your business problem and ROI?

2. Rate the relevance of each interaction (discovery, demo, proposal) on a 1–5 scale.

3. Were decision-makers appropriately engaged by our team?

4. Did any stage of the process feel rushed or stalled? Please specify.

5. What resources (case studies, calculators, references) would have improved your confidence?

Pore over these responses with your sales and enablement teams. Improvement isn’t accidental—it’s intentional, and this is your playbook.

Choosing the Right Recipients & Timing for Win-Loss Surveys

Timing is everything. Send your win-loss surveys too soon, and buyers may ignore them; wait too long, and the details blur. The sweet spot for most is:

• Email surveys: 24 to 72 hours after decision for high open rates.
• Phone interviews: 7 to 14 days post-decision for deeper feedback.

Selecting recipients is just as vital. Aim to target:

• Decision makers (aka economic buyers) for overarching business drivers.
• Technical evaluators for precision on product fit and functional requirements.
• User champions for unique perspectives on experience and team dynamics.

A multi-touch approach often works best:

• Start with a brief email survey for quick, candid input.
• Follow up with a targeted phone interview for richer storytelling and context.

Cadence and flexibility are key. Rotate outreach among personas and types of opportunities to keep your analysis balanced and your response rates healthy. Strike while the iron’s hot, and feedback will always be more honest.

Best Practices: Dos and Don’ts for Designing & Delivering Win-Loss Surveys

Let’s keep it real—survey design can make or break your efforts. Here are the essential best practices for win loss surveys everyone should follow.

Dos: - Keep surveys brief and focused—no one loves a never-ending form. - Personalize your introduction for each recipient. - Offer anonymity to encourage frank, honest answers. - Align every question with the recipient’s actual role in the deal. - Always close the loop internally by sharing top findings with go-to-market teams.

Don’ts: - Avoid asking leading or loaded questions that bias the answer. - Don’t send surveys immediately after delivering bad news—they’ll be ignored. - Never bribe for positive responses; authenticity is key. - Don’t ignore lengthy qualitative comments—these nuggets hold the richest insights.

Simple, direct, and respectful surveys get the highest response rates and the most actionable feedback. By sticking to these survey design tips, you ensure your survey isn’t just filling a spreadsheet—it's fueling next quarter’s wins.

Turning Win-Loss Survey Data into Actionable Insights

So, you’ve collected a pile of feedback—don’t let it gather dust. Turning win-loss survey data into action is where you’ll truly improve win rates.

Here’s how to do it right:

• Code qualitative responses to surface recurring themes quickly.
• Identify patterns in deal drivers and blockers, slicing by vertical, competitor, or deal size.

• Quantify feedback and create easy-to-digest dashboards:

  • Win rate improvement by team or vertical
  • Shortening of average sales cycle time
  • Rise in competitive displacement rates

• Feed themes directly into product, pricing, and enablement strategies.

• Schedule closed-loop meetings between sales, marketing, product, and leadership for deep-dive reviews.

Most importantly, ensure buyer feedback isn’t a one-and-done. Operationalize buyer feedback by continuously updating your revenue playbook and tying changes to business outcomes. The entire organization wins when you transform data into action—and watch those win rates climb.

Finally, remember: win-loss analysis isn’t just about deals, but about people, processes, and perpetual improvement. The more you listen—and act—the more you’ll win, again and again.