Your First Win/Loss Interview: The Script I Wish I Had

I bombed my first win/loss interview so badly the customer actually asked if I was okay.

I had my questions printed out. I had my note-taking document open. I'd read three articles about win/loss best practices. I was prepared.

The customer answered my first question—"Why did you choose us over the competitor?"—and I panicked. They didn't give me a simple answer. They told a story about a board meeting, a frustrated VP, a failed proof-of-concept with another vendor, and a conversation with their implementation team about technical requirements I didn't fully understand.

I frantically typed notes. I lost track of what they were saying. I asked them to repeat things. I skipped half my prepared questions because I was so focused on capturing their words that I forgot to actually listen.

Fifteen minutes in, they paused and said, "Are you getting what you need? You seem stressed."

I was. Because I'd treated the interview like a survey I was reading aloud instead of a conversation I was having. I was so focused on my script that I missed the entire point: win/loss interviews aren't about asking questions—they're about following the story.

That disaster taught me more than any article could. The script I use now isn't a list of questions to ask in order. It's a framework for following wherever the customer leads while making sure I don't miss the insights that matter.

The Mistake That Ruins Most Win/Loss Interviews

Most people approach win/loss interviews like surveys. They have ten questions. They ask question one, wait for an answer, ask question two, wait for an answer, march through their list.

This approach generates data but misses insights.

Here's what actually happens in a good win/loss interview: the customer mentions something interesting in their answer to question three. You ask a follow-up question. They tell a story that reveals a truth about their buying process you didn't expect. You ask another follow-up. They mention a competitor you didn't know was in the deal. You explore that angle. Forty minutes later, you've asked maybe four of your ten planned questions, but you've uncovered insights that will change your entire sales playbook.

The script isn't the questions you ask—it's the map that keeps you from getting lost while you explore.

I learned this by watching someone who was actually good at win/loss interviews. I sat in on a call where my colleague interviewed a customer who chose a competitor. I expected her to grill them on why they didn't choose us.

Instead, she started with: "Tell me about the moment you realized you needed to solve this problem."

The customer talked for eight minutes. They described a quarterly business review where the CEO asked for a metric they couldn't produce. They talked about the manual process they were using. They mentioned that three different teams were keeping their own spreadsheets with conflicting data.

My colleague didn't interrupt. She took minimal notes. She just listened.

When the customer finished, she asked: "You mentioned three teams keeping separate spreadsheets. Walk me through what happened when you tried to get them aligned."

The customer talked for another six minutes about the political complexity of getting teams to agree on definitions and processes. This led to a story about why they needed a solution that didn't require heavy change management.

Twenty minutes into the interview, my colleague had asked two questions. But she'd uncovered the real reason they chose the competitor: not features or pricing, but the fact that the competitor's solution worked with their existing workflows while ours required process changes.

I had interviewed ten customers and missed this pattern because I was too busy checking questions off my list to actually listen.

The Framework That Actually Works

After watching that interview, I rebuilt my approach. I stopped thinking about win/loss interviews as Q&A sessions and started thinking about them as guided storytelling.

The framework has three parts, but they're not sequential steps—they're themes you explore throughout the conversation.

The Trigger: What Created Urgency

Every buying decision has a trigger moment—the specific event that turned a tolerable problem into an urgent priority. Most customers won't tell you this unless you ask specifically.

I start every interview now with some version of: "Walk me through the moment you realized you needed to solve this problem. What was happening that made this urgent?"

This question does something magical: it transports the customer back to the moment of pain. They stop giving you post-rationalized corporate answers and start telling you the real story.

I interviewed a customer who chose a competitor, and their answer to this question revealed they'd made the decision in 48 hours because their biggest client threatened to leave if they couldn't provide a specific capability. Our sales cycle had been four months. We never had a chance because we didn't know urgency existed.

That insight changed how we qualify deals. We added a discovery question: "What's driving the timeline for this decision?" We started disqualifying deals where no trigger event existed because we learned those deals either never close or take forever.

The trigger question also reveals whether you're solving the right problem. I've interviewed customers who chose us, and their trigger was completely different from what our marketing messaging assumed. We thought they bought us for efficiency gains. They actually bought us because a regulatory change created a compliance requirement and we were the only vendor who understood the regulation.

That one interview changed our positioning for an entire segment.

The Journey: Who Was Involved and What Happened

The second theme is understanding the buying journey—not the sanitized timeline in your CRM, but the messy reality of what actually happened.

I ask some version of: "Walk me through the process from that trigger moment to making a decision. Who got involved? What did you evaluate? Where did things get complicated?"

This is where you discover the real decision criteria, the hidden stakeholders, and the moments where deals get won or lost.

I interviewed a customer who chose us after evaluating three competitors. According to our CRM, we won on product capabilities. According to the customer's story, we won because our sales engineer responded to a technical question in twelve hours while the competitor took four days.

The customer had a board meeting coming up. They needed an answer to present to the board. Our competitor had better features, but our speed gave the customer confidence we'd be responsive after the sale. We won on service expectations, not product capabilities.

I never would have learned this from my prepared questions about features and pricing.

The journey questions also reveal political dynamics. I interviewed a customer who chose a competitor and discovered the real blocker wasn't our product—it was that their VP of IT hated our parent company because of a bad experience five years ago. Our sales rep never met the VP. We were doomed from day one.

These are the insights that change how you sell, not just to this customer, but to every similar customer.

The Comparison: How They Actually Decided

The third theme is understanding how they compared options and made the final decision. Not what their decision criteria were on paper, but how they actually decided when multiple options looked viable.

I ask: "When you got to the point where you had to choose between us and [competitor], what was the conversation like? How did you make the final call?"

This reveals the tiebreakers—the factors that matter when everything else is equal.

I interviewed a customer who chose us over a competitor with nearly identical capabilities and pricing. The tiebreaker? Our competitor's sales rep didn't customize the demo. They showed a generic version. Our rep built a custom demo with the customer's actual data and workflows.

The customer said: "Both products could probably work, but your rep showed me it would work. Their rep told me it would work. That made the difference."

We turned that insight into a sales requirement: every final demo must use customer data. Win rates on competitive deals increased 15%.

The comparison theme also reveals objections you don't know you're creating. I interviewed a customer who chose a competitor and learned that our pricing model made the CFO nervous because it was consumption-based and therefore unpredictable. The competitor had flat-rate pricing. The CFO insisted on the competitor because they needed budget certainty.

Our product was better. Our price was lower. But our pricing structure created risk the customer wasn't willing to take. We added a flat-rate option. The objection disappeared.

The Questions I Actually Ask

The framework gives you the themes to explore. But you still need specific questions to ask when the conversation stalls or when you need to dig deeper.

These are the questions I ask in almost every interview. Not in this order—in whatever order makes sense based on where the conversation goes.

"Tell me about the moment you realized you needed to solve this problem." This starts the conversation and gets to the trigger.

"Walk me through what happened next." This keeps the story moving without imposing structure.

"You mentioned [thing they said]. Tell me more about that." This is how you go deep on interesting threads.

"Who else got involved at that point?" This reveals hidden stakeholders and political dynamics.

"What almost derailed this decision?" This uncovers objections and concerns that might not come up otherwise.

"When you were comparing us to [competitor], what was that conversation like?" This gets to real decision criteria.

"If you were advising someone in a similar situation, what would you tell them to watch out for?" This often reveals regrets or concerns they won't state directly.

"Is there anything I should have asked about that I didn't?" This catches gaps in your understanding.

That's it. Eight questions. I rarely ask all of them in one interview. I usually ask three or four, with lots of follow-ups based on their answers.

The magic isn't in the questions—it's in actually listening to the answers and following the interesting threads instead of marching through your list.

What To Do When The Interview Goes Sideways

Even with a good framework, interviews go sideways. The customer gives one-word answers. They ramble about irrelevant details. They're guarded and won't tell you the real story.

Here's what I do when that happens.

When they give short answers: I get more specific. Instead of "Why did you choose us?" I ask "Tell me about the meeting where you made the final decision. Who was there? What did they say?"

Specific questions trigger detailed memories. Generic questions get generic answers.

When they ramble: I gently redirect. "That's really interesting. I want to make sure I understand the timeline. You mentioned X happened first—what happened right after that?"

You're not cutting them off. You're helping them tell a coherent story.

When they're guarded: I acknowledge it. "I know this might feel a bit awkward since you chose the competitor. I'm not trying to change your mind—I'm genuinely trying to understand what we could have done differently. Whatever you share helps us get better."

Permission to be honest often unlocks honest answers.

When you realize you're lost: I stop and admit it. "I want to make sure I'm understanding this correctly. You started evaluating solutions in January, the board meeting was in March, and somewhere in there the technical team got involved. Can you help me understand the sequence?"

Admitting confusion is better than pretending to understand.

The One Thing That Matters More Than Your Questions

The biggest difference between my terrible first interview and the interviews I run now isn't the questions I ask. It's that I stopped trying to control the conversation and started trying to understand the story.

When I was bad at win/loss interviews, I treated customers like data sources. I had questions I needed answered. I needed them to give me specific information. I was extracting insights.

Now I treat customers like experts teaching me something I don't know. They lived through a complex buying decision. They know things about their process, their needs, and their evaluation that I can't know from CRM data and sales notes. My job is to learn from them.

This mindset shift changed everything. I stopped worrying about whether I was asking the "right" questions and started focusing on whether I was understanding their story. I stopped taking frantic notes and started listening. I stopped trying to finish in 30 minutes and started letting conversations run as long as needed.

The insights got better because I was finally paying attention to what customers were actually telling me instead of waiting for them to answer my questions.

Your first win/loss interview will probably be awkward. Mine was a disaster. But if you focus on following the story instead of following your script, you'll learn more from that one conversation than from ten surveys.

And eventually, you'll stop needing the script at all.