Churned customers and lost prospects are harder to reach because the relationship has ended or never started. But they are often more valuable to interview because they have less reason to be polite.
For churned customers, reach out from someone they had a relationship with if possible. The account manager or customer success person they worked with. Explain that you are trying to understand what you could have done better, and their honest feedback would help.
For lost prospects, the salesperson who ran the deal should reach out. Frame it as learning, not a second chance to pitch. Something like: "I know you went with [competitor], and that is totally fine. I would love to understand what made the difference. Would you have fifteen minutes to share your perspective? It would really help us improve."
Do not be afraid to reach out even if time has passed. People are often happy to share their experience if you approach them with genuine curiosity rather than a hidden agenda.
Four to twelve interviews is enough to see patterns. After ten or twelve conversations, you start hearing the same things repeated. That is when you know you have enough.
Do not aim for statistical significance. This is qualitative research. You are looking for themes, language, and stories that help you understand the decision-making process. Five deep interviews are worth more than twenty surface-level surveys.
I recommend spreading your interviews across the three groups: a few best customers, a few churned customers, and a few lost prospects or competitors' customers. This gives you perspective across the entire journey rather than just one segment.
Plan for about thirty minutes per interview. Some will run shorter, some longer. Block forty-five minutes in your calendar to give yourself buffer.
The whole process, from first outreach to final interview, should take two to three weeks. Do this every quarter, and you will always have fresh insight to work with.
I generally do not use incentives because they can skew results. When you pay someone, they may feel obligated to be positive. You want honest feedback, including the hard stuff.
That said, context matters. If you are asking someone to travel to your office, pay for their transport. If you are asking a lot of time from a very senior person, a small Amazon voucher as a thank-you is reasonable.
For churned customers or lost prospects, you may need to offer something to get them over the line. They have less reason to help you. A small token of appreciation can make the difference.
Whatever you do, do not offer your own product as the incentive. It creates awkward dynamics and attracts people who just want free stuff. Keep it neutral.