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For most win-loss programs, the buyer鈥檚 perspective is the starting point, and rightly so. Buyers tell you why they chose your solution or walked away.

But what about the other side of the story?

Your sales team is on the front lines from the first disco call to the final proposal. They see exactly where opportunities stall, what moves competitors make, and how internal bottlenecks quietly derail deals before buyers even notice.

In short, by listening to both buyers and sellers, you鈥檒l gain a complete picture of every deal outcome.

In this guide, you鈥檒l learn:

• Why you should include seller interviews in your win-loss program
• Who on the sales team you should interview
• How to structure your first seller conversation

Let鈥檚 get started.

馃搶 Need a complete win-loss overview? Check out our ultimate guide to win-loss. And if you want to master buyer interviews next, download the doc below.

What is a Seller Interview?

Seller interviews are structured conversations with your sales team that capture the 鈥渋nside story鈥� of competitive deals. These typically involve AEs, Solutions Engineers, and sales leaders who were directly involved in the opportunity.

Unlike CRM data or sales notes, these interviews dig deeper into the human elements of deals 鈥� the unexpected objections that surfaced, how competitors adapted their tactics mid-deal, and how your internal processes either accelerated or derailed your opportunities.

To be clear, the goal isn鈥檛 to second-guess your sales team but to uncover patterns and insights they observe across multiple deals that might not be visible from win rates and close dates alone.

Why You Should Include Seller Interviews in Your Win-Loss Program

While buyer feedback forms the foundation of win-loss analysis, your sales team brings critical context to the table.

Here are four reasons you should include seller interviews as part of your program:

Faster, More Flexible Feedback

Buyer interviews often take weeks to schedule, especially with prospects who have moved on. Meanwhile, your sales team is typically just a Slack message away. This quick access means you can capture fresh details while the deal is still top of mind.

, Senior Director of Competitive Intelligence at Salesforce, highlights this advantage: 鈥淲e want to make sure that we can find out things very quickly. We don鈥檛 need to wait six weeks to get buyer feedback. We can turn these things around in a day if we need to.鈥�

Uncover Internal Friction Points

Sellers have a front-row seat to every snag in your internal processes. Through seller interviews, you might discover that:

• Security reviews take three weeks while competitors complete them in days
• Pricing approvals through the deal desk create momentum-killing delays
• Demo environments frequently crash or show outdated features, undermining sales credibility during key presentations

These behind-the-scenes bottlenecks rarely surface in buyer interviews 鈥� yet they can silently torpedo deals before external factors even come into play.

Get Real-Time Competitive Intel

When competitors make moves, your sellers feel the impact first. Through regular seller interviews, you鈥檒l uncover crucial competitive intel like:

• A competitor bundling premium features into their base package 鈥� and winning
• Your top rival鈥檚 new 鈥渕igration calculator鈥� making your TCO look inflated
• An emerging player offering flexible 18-month contracts that resonate with risk-averse buyers

This early-warning system helps you adapt your competitive strategy in real-time. 

Help You Build Trust With Your Sales Team 

Perhaps the most valuable benefit isn鈥檛 the competitive intel or process insights, it鈥檚 the relationship you forge with your sales team. Many sales organizations initially view win-loss as a blame game, but seller interviews completely flip this dynamic.

By making sellers active partners in improving how your company wins deals 鈥搃nviting their insights, acting on their feedback, and showing how their input shapes strategy 鈥� you鈥檒l quickly turn win-loss skeptics into champions.

As Hamilton explains: 鈥淲e鈥檙e not just asking, 鈥楬ey AE, what happened in this one deal?鈥� We鈥檙e actually trying to build a relationship with them over time鈥� Those checkpoints are really big for us to keep up that momentum鈥� if we have somebody new in the seat or a new leader.鈥�

Who Should You Interview

Different sales roles see different parts of a deal. To get a full view, especially for major opportunities, you鈥檒l want to consult multiple team members.

Here鈥檚 who to prioritize:

Account Executives (AEs)

AEs manage buyer relationships and know exactly when interest spiked, which objections surfaced, and where momentum stalled.

Solutions Engineers (SEs)

SEs offer technical perspective, pinpointing product gaps and revealing whether your demos actually connect with technical decision-makers.

Sales Leaders

Directors and VPs see patterns across multiple deals and can identify strategic gaps individual contributors might miss.

馃挕 Tip: Keep interviews under 20 minutes. Focused conversations respect sales鈥� time while delivering valuable insights.

How to Prioritize Deals for Seller Interviews

A strategic approach to interview selection ensures you gather high-impact insights for your business.

Here鈥檚 how to prioritize deals and select interviews, according to Salesforce鈥檚 Dan Hamilton:

Balance Strategic Focus with a Baseline of Key Deals

Every quarter, ensure you cover both high-impact deals and emerging trends:

• Set a baseline: Prioritize at least 10 wins and 10 losses per quarter to maintain a steady flow of insights.
• Layer in strategic priorities: Adapt based on evolving business needs:
  • Just launched an AI feature? Target deals where it was positioned.
  • Expanding into healthcare? Interview teams working on those accounts.
  • Is a competitor making aggressive moves? Dig into those deals to uncover patterns.
• Validate assumptions: Many 鈥渓osses鈥� aren鈥檛 actually losses, and not all wins are definitive victories. Interviews help separate perception from reality.

Move Fast, But Be Strategic

Hamilton鈥檚 team prioritizes speed and efficiency when selecting deals for seller interviews:

• Act quickly: Some insights need to be surfaced within days 鈥� not weeks 鈥� to make a real impact.
• Avoid overloading sellers: Schedule interviews at the right time (not during quarter-end).
• Iterate: If initial interviews reveal gaps, follow up with additional team members for deeper insights.

Go Beyond Just Large Deals

While big, high-profile deals offer great insights, Hamilton advises including mid-sized or smaller deals that flew under the radar:

• These deals often lack executive intervention, making them a clearer reflection of your standard sales motion.
• They can highlight repeatable patterns in your competitive wins and losses.

Focus on Late-Stage Competitive Deals

The most valuable insights, according to Hamilton, come from opportunities that progressed deep into the sales cycle, especially head-to-head battles with key competitors. These deals reveal:

• Where your positioning resonates (or falls flat)
• How pricing, relationships, and product capabilities impact the final decision
• Internal sales process friction that might be affecting competitive win rates

By taking a structured yet flexible approach to deal prioritization, your seller interviews will generate insights that are timely, relevant, and actionable.

馃搶 For more methods of prioritizing deals, check out our.

Structuring Your Seller Interviews

With your interview targets identified, it鈥檚 time to build conversations that deliver results.

Great seller interviews share these key elements:

• They connect directly to your win-loss learning objectives
• They leverage theD.E.P.T.H framework
• They validate or challenge insights from buyer interviews

Below are six critical areas to explore in your seller interviews, with suggested questions for each. While you can follow this framework step-by-step, we recommend focusing on areas most relevant to your situation.

1. Deal Context & History

Set the stage by understanding the context and specifics of the sales opportunity, the timeline of the deal, and the prospect鈥檚 needs.

Key questions to ask:

• 鈥淲alk me through the deal history from first contact to close.鈥�
• 鈥淲hich competitors were involved and at what stages?鈥�
• 鈥淲hat was unique or challenging about this opportunity?鈥�

Why it matters: Different deals follow different paths. Understanding the specific journey helps you interpret the feedback accurately and identify where things went right or wrong.

2. Deal Outcome

Get the seller鈥檚 direct assessment of why you won or lost the opportunity.

Key questions to ask:

• 鈥淚n your view, what are the primary reasons we won/lost this deal?鈥�
• 鈥淲ere there any decisive factors that influenced the prospect鈥檚 decision?鈥�

Why it matters: The seller鈥檚 immediate perspective on deal outcomes often reveals blind spots that buyers won鈥檛 mention. This provides the foundation for every other question and helps you quickly identify if internal and external perceptions align.

3. Competition

Identify which competitors were involved and how their offerings compared to yours in this specific deal.

Key questions to ask:

• 鈥淲ho else was in the running, and how did we compare?鈥�
• 鈥淲hat did the prospect see as the main strengths of our competitors?鈥�
• 鈥淲ere there any notable weaknesses in their offerings that worked in our favor?鈥�

Why it matters: Sellers encounter competitor tactics and prospect objections firsthand. This Intel helps you adjust your competitive strategy in real-time, spotting emerging threats months before they show up in broader market trends.

4. Seller Successes

Highlight what went well during the sales evaluation and where the seller felt confident.

Key questions to ask:

• 鈥淲hat do you think went well during this evaluation?鈥�
• 鈥淲here did you feel most confident?鈥�
• 鈥淲hich strategies or tactics proved most effective?鈥�

Why it matters: Understanding strengths is just as important as identifying weaknesses. This gives sellers an opportunity to share their wins and successful tactics, creating positive engagement with the win-loss process while providing valuable approaches you can replicate across your sales organization.

5. Seller Opportunities

Identify areas where the seller believes improvements could be made in future sales processes.

Key questions to ask:

• 鈥淲hat do you think could have gone better or could be improved upon in the future?鈥�
• 鈥淲hat, if anything, would you do differently given the chance?鈥�
• 鈥淲ere there any challenges that you felt unprepared for?鈥�

Why it matters: These forward-looking insights help prevent repeating the same mistakes in future deals. By focusing on improvement rather than blame, you鈥檒l uncover specific areas for development while maintaining a constructive relationship with your sales team.

6. Organizational Opportunities

Identify process gaps, resource needs, and systemic issues that impacted the deal.

Key questions to ask:

• 鈥淲hat internal hurdles did you face during this sales process?鈥�
• 鈥淲ere there any resources you wish you had but didn鈥檛?鈥�
• 鈥淗ow can we better support you in future opportunities?鈥�

Why it matters: Internal friction often kills deals before external factors come into play. These insights help remove systemic barriers that impact multiple deals and provide concrete ways to improve your competitive position through organizational changes.

Looking to organize your growing interview data? Our guide on shows you how to structure findings for maximum impact.

Some Final Seller Interview Tips 

Before diving into your seller interviews, keep these best practices in mind to ensure productive conversations:

• Keep it brief: Aim for 15-minute conversations that respect sellers鈥� time while yielding direct, actionable feedback.
• Create psychological safety: Make it clear you鈥檙e seeking organizational learning, not assigning blame for losses or individual missteps.
• Mind your timing: As Dan Hamilton notes: 鈥淣o AE wants to get a Slack message from some junior PMM they鈥檝e never heard of the last week of the fiscal year asking about a deal they lost.鈥� Avoid quarter-end pressures.
• Close the feedback loop: Share insights back with your sales organization by:
  • Creating quick-turn enablement addressing competitive gaps they鈥檝e identified
  • Updating battlecards with actual competitor messaging they鈥檙e encountering
  • Advocating for process changes that remove highlighted friction points

Completing the Win-Loss Picture

Buyer and seller perspectives aren鈥檛 competing narratives 鈥� they鈥檙e complementary views that together reveal the full story behind each deal. By incorporating seller interviews into your win-loss program, you create a powerful feedback loop where field intelligence directly shapes your go-to-market strategy.

Oh 鈥� and if you鈥檙e ready to learn more about win-loss, check out our guides on:

• Conducting win-loss interviews with buyers

And don鈥檛 forget to download our win-loss interview guide 馃憞