I used to think customer interviews were a qualitative exercise that lived in the marketing or product team’s world — useful for empathy, not for closing enterprise deals. After a decade working revenue operations and GTM for B2B businesses across Europe and the UK, I’ve flipped that view. Done right, customer interviews can double your win rate on enterprise deals by giving you the intelligence to shape value propositions, uncover decision dynamics, and remove blockers before they appear in the sales cycle.
In this post I’ll share how I run customer interview programs that feed the sales pipeline, the exact questions that reveal purchase signals, a lightweight template you can use on calls this week, and the KPIs I track to prove impact. These are practical steps I’ve used with startups and midsize vendors to shorten cycles, increase conversion and turn pilots into multi-year contracts.
Why customer interviews move the needle on enterprise deals
Enterprise buying is social and political. Deals are rarely won on tech specs alone — they’re won when your offering maps to a buyer’s prioritized outcomes, when you surface and neutralize internal blockers, and when champions can build a simple, credible case to their stakeholders.
Customer interviews do three things that directly increase win rate:
Two interview tracks: Discovery and Reference
I run interviews in two distinct tracks that serve different sales stages:
Keeping these tracks separate prevents fuzzy objectives and ensures calls produce assets that sales reps can use directly in deals.
How I recruit interviewees — fast and at scale
Recruiting doesn’t have to be expensive. I use three channels, prioritized by speed and relevance:
Offer something valuable in return: a benchmarking report, an executive summary of findings, or an invite-only roundtable with peers. This compensates time and builds goodwill. In enterprise deals I often offer a short report that the prospect can use internally to justify the business case — it’s both a carrot and a conversion lever.
Interview script that consistently surfaces buying signals
Use a simple, repeatable script so insights are comparable across calls. I coach reps to keep interviews short (20–30 minutes) and to record or take structured notes. Here’s the script I give them:
| Intro (2 min) | Explain purpose, confirm time, get permission to record. |
| Context (3–5 min) | “Tell me about your role and the top 1–2 objectives you’re accountable for this quarter.” |
| Pain and metrics (7–8 min) | “What’s the business problem you’re trying to solve? How is it measured today? What would success look like in numbers?” |
| Process & stakeholders (5–6 min) | “Who else needs to sign off on this? What does an ideal vendor selection process look like for you?” |
| Risk & alternatives (3–4 min) | “What concerns would make you pause? What are you evaluating besides us?” |
| Close (2 min) | “What would make you recommend a purchase to your leadership right now?” Ask to introduce to other stakeholders if appropriate. |
Two quick notes: first, always ask for metrics — numbers change conversations from fuzzy to urgent. Second, end by asking for introductions. If a buyer is willing to introduce you to their procurement or CFO, that’s a strong buying signal.
Turning interview output into sales assets
Raw notes are useless unless they turn into something reps can use. I standardize outputs into three living assets:
These assets live in your CRM or a shared drive with tags by industry and use case so reps can pull them instantly during live demos or negotiation calls.
Sample objections and the question that kills them
From dozens of calls I’ve conducted, three objections keep showing up. Here’s how one targeted interview question can disarm each:
KPIs to prove interviews move revenue
When you want to convince leadership to invest in a customer interview program, track these metrics:
Quick playbook to launch this week
Implementing this takes discipline: schedule interviews as part of the sales process, template notes in your CRM, and make it a monthly rhythm. But the payoff is clear: better-qualified deals, clearer internal champions, and fewer surprises at procurement. If you want, I can share a downloadable interview note template and a battlecard example you can drop into your CRM — tell me which CRM you use and I’ll adapt the template for that system.
