How to Recruit and Conduct a Win-Loss Interview

Jen Doyle and Aldona Dye broke down the art of conducting effective win-loss interviews using Klue’s DEPTH model (Details, Engaged, Personal, Trust, High-impact). Through practical examples and techniques, they emphasized how proper buyer targeting and interviewing skills can uncover crucial competitive insights that move beyond surface-level feedback like “we lost on price.”

🌶️ Pipin’ Hot Takeaways:

1. Build target lists with three key criteria: clear learning objectives (if we knew X, we could do Y), proper CRM segmentation (90-day window, late-stage losses), and enough volume (50-60 qualified deals for 10-12 interviews)
2. Apply the DEPTH framework—stay Detail-oriented with follow-ups, stay Engaged with empathy, keep it Personal with role context, establish Trust as a neutral party, and maintain High-impact alignment with program goals
3. Focus on quality over quantity—aim for 10-15 excellent questions in a 30-minute interview, using open-ended prompts like “That’s interesting, tell me more about that” to uncover deeper insights

🎤 Mic Drop Moments:

1. On Details: “It’s not enough for them to say ‘there were some features we liked.’ What features were those? What was that use case? We really want to follow up.”
2. On Building Trust: “Using a third party is very helpful in building trust. They know we’re an unbiased party, and that’s one of the benefits of the Klue interviews.”
3. On Roles: “Be conscious if you’re speaking to an end user or a decision maker buying for end users—it’s a very important and distinct role that you need to adjust your questions for.”

Session slides below: