Willem Maas

For continuous win/loss insights, consider combining a once-per-year formal win/loss analysis (eg interviews and scorecarding with decision makers) with quarterly win/loss reviews. During the quarterly reviews you're with the sales team, debriefiing on each deal to find win or loss causes. To those reviews, bring as much deal data (prospect demographics, competitive, etc) as you can from your CRM to identify patterns. You act as the voice of the buyer (VOB), providing a counterpoint to the internal perspective, leveraging what you learned during the once/year buyer interviews.

Feedback from champions in recent deals can be helpful here, too. When was it hard to make the case internally to switch to your product? How did any competitors in the deal make it easy to buy from them than you? Correlating the buyer's experience/ feedback with your won and lost outcomes should help both you and sales make objectively better decisions.

For a current feature, I'd ask your customer about using it in a recent time period (eg last month or last week). How many times in that span? How did she use it, or even better show you how. What does she recall liking or disliking about it? For an upcoming feature, in recent time period, has there been a situation when she would have used it? What's an alternative way she completes that task now? Pros and cons?

@Vishal Naik I agree! In a former life as a B2B product manager, I struggled to get useful input on the needs of new buyers. Most of my time and attention was spent enhancing the current product for current customers. Input about new buyers was often in the form of "specials" for large deals. By providing a cohesive analysis of the new buyer's decision making PMM can definitely make it easier for Product. I think this would be a welcomed influence on the roadmap.