5 powerful questions to ask in a Win-Loss interview

If you don’t ask the right questions, you’ll never get the real answers.

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Imagine this: you’ve just lost (or won) a strategic deal. The sales rep logs “budget” or “good fit” in the CRM. End of story.

Except… it’s rarely just about budget. And rarely just about fit.

According to data aggregated by Diffly from hundreds of interviews, over 80% of the reasons behind wins and losses are either unknown or misunderstood by companies. Why? Because they don’t take the time to ask — or they ask the wrong questions.

That’s exactly what Win-Loss interviews are for: going deeper than the official reasons. But to get to the real insights, you need to ask your prospects and customers the right questions.

In this article, you’ll discover:

• The 5 most powerful questions to ask in a Win-Loss interview (tested across hundreds of conversations),
• Real-life examples of answers shared by B2B companies,
• And how to turn those answers into strategic decisions (go-to-market, pricing, messaging, sales cycle…).

Ready? Let’s dig in.

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Question 1 – How did you experience the sales process with our team?

This is the gateway to how the overall deal was perceived. You’re diving into the human experience: pacing, quality of interactions, empathy… in short, everything a CRM can’t capture.

What you’re looking to uncover

• Points of friction (slow responses, lack of clarity, pressure felt, etc.),
• Accelerators (impressive demo, social proof, helpful templates, etc.),
• The impact of your sales approach on the final decision.

In over a third of the Win-Loss interviews conducted by Diffly, the sales experience weighs more heavily than the product features themselves.

Real-world example

One of our clients discovered through their “lost” interviews that several prospects walked away when follow-ups were too frequent: “It felt like we were being harassed.”

As a result, they implemented a gentler follow-up cadence, paired with educational content between touchpoints.

What this enables

• Optimizing your sales sequence (timing, content, tone),
• Training your Account Execs in active listening rather than just product pitching,
• Highlighting your experience-driven differentiation versus more aggressive competitors.

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Question 2 - How did you position {Company Name} compared to other competitors?

You’re mapping the prospect’s mental model: where do they place you? Next to whom? Ahead, equal, or behind?

What you’re looking to uncover

• The actual competitors considered (direct, internal, or “do nothing”),
• The criteria used to compare (price, UX, integrations, trust),
• Your differentiation territory — or the absence of perceived differentiation.

According to a Gartner study, over 30% of B2B buying decisions are ultimately dropped in favor of internal solutions or the status quo (“do nothing”).

Real-world example

One of our clients thought they were competing with new-age accounting tools. Their interviews revealed that 1 in 3 prospects were actually comparing the solution to “Accounting firm X + Google Drive + Excel.”

This led them to create a landing page: “[Platform] vs. Excel” — targeting the real comparison being made.

What this enables

• Segmenting your campaigns with the right reference points (“replace Excel” rather than “faster than X”),
• Equipping your sales team with battle cards aligned with real market perception,
• Creating comparative content that answers actual buyer questions.

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Question 3 – How did the decision-making process go on your side, and who was involved?

The buying process is rarely linear. This question highlights the internal loops, invisible stakeholders, and political friction points.

What you’re looking to uncover

• The actual workflow: steps, durations, approvals, committees,
• The key roles (champion, veto, CFO, security, etc.),
• The pain points that prolong the cycle and kill deals.

Gartner estimates that the B2B buying cycle involves an average of 6 to 10 different decision-makers.

Real-world example

An HR Tech vendor learned that a deal was “stalled” because the CIO had to validate GDPR compliance… and had never received a clear answer about data location. Since then, every opportunity over €20k includes an IT compliance kit sent before the legal phase.

What this enables

• To map the influencers (and tailor your content to each),
• To shorten the sales cycle by eliminating approval bottlenecks,
• To equip your internal champions to sell internally on your behalf.

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Question 4 – How do you justify (in terms of ROI) the investment in a solution like ours?

Price only becomes a concern if the value isn’t clear. This question reveals the prospect’s economic rationale: expected gains, tracked KPIs, and payback horizon.

What you’re looking to uncover

• The business metrics that truly matter (ARR, cost reduction, NPS, compliance, etc.),
• The reasonable timeframe to prove value (3 months, 12 months, 3 years),
• The comparison scenarios used to justify the purchase (internal cost, risk avoided, productivity).

Real-world example

One of our clients learned that their SME customers justified the subscription with a simple equation: “1 internally produced video = 4 hours of a graphic designer at €50 = €200,” while a user of the solution can produce 4 videos in 1 hour.

The marketing team then created an ROI calculator based on this ratio.

What this enables

• To quantify your promise and make it tangible,
• To create ready-to-use business cases for your prospects,
• To adjust your pricing (or packages) to what customers perceive as value.

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Question 5 – Did the price accurately reflect the value of the solution? Why or why not?

Final stretch: you directly confront the price ↔ value perception. Not to discuss discounts, but to understand the psychological balance of the transaction.

What you’re looking to uncover

• The perceived price level (expensive, premium, reasonable, cheap),
• The elements that confirm value (features, service, support, brand),
• The latent objections (lack of transparency, complex model, hidden costs).

Real-world example

One of our clients discovered that their “card + monthly subscription per user” model was considered too unclear by CFOs. In response, they launched a total cost simulator and simplified their pricing grid to 2 all-in plans, reducing the dropout rate by 18% at the end of the cycle.

What this enables

• To validate (or not) your pricing strategy,
• To identify the value levers to highlight (customer service, expertise, security),
• To anticipate pricing objections and equip your sales team to address them.

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Summary Table of the 5 Questions & Action Levers

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💡 Tip: add an “Importance Score (1-5)” column for each interview; you’ll quickly get a priority matrix for your Sales, Marketing, and Product teams.

Bonus: 3 Posture Rules for Interviews That Are Worth Their Weight in Gold

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1. Absolute neutrality: no defense, no arguing. You listen, period.
2. Productive silence: after each answer, wait 2-3 seconds. The nuggets often come out in the pause.
3. Tight timing: contact the prospect 2 to 4 weeks after the decision, when memories are fresh and emotions have settled.

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Conclusion: The Right Questions Turn Your Interviews into a Competitive Advantage

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Deals are rarely won or lost on a single feature or number. They are decided by perceptions, experiences, and value logics that only your prospects can describe.

By asking these 5 questions — and truly listening to the answers — you reveal:

• Why your sales journey appeals to… or frustrates,
• Where you really stand in the minds of the market,
• How your customers build their business case,
• And whether your pricing tells the same story as your value proposition.

It’s not the loss that hurts. It’s not knowing why.

Ask these questions. Dig deeper. Listen without defending. And turn every Win-Loss interview into a growth engine.

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