Win/Loss Sales Interviews for your B2B

Last week, I started a series on the types of Customer Interviews. Today, I'm going to wrap up the series with Win/Loss Sales Interviews, which is one of my favorites.

When to do Win/Loss Sales Interviews? 

> When sales team performance isn't hitting the target metrics

> When you continually lose deals to one competitor and want to know why

How often to do them?

> Monthly

Who is the target audience?

> Customers who recently went most or all of the way through your sales process

> Include both customers and non-customers (who didn't buy)

What you're trying to understand?

> Sales effectiveness

Sample questions:

> "What was the biggest consideration you based your decision on?"

> "How well did we tailor our presentation to your needs?"

> "What's one thing you'd advise us to change for next time?"

My closing thoughts on Win/Loss Customer Interviews

Conducting regular Win/Loss Customer Interviews results in more sales. Why? You see first hand why your customers buy (or don't buy). Because of this, I recommend doing these interviews monthly. 

If you have questions about Win/Loss Customer Interviews, hit reply and let me know.

Frequently Asked Questions

When is the right time to start doing Win/Loss Sales Interviews?

When sales team performance isn't hitting target metrics, or when deals are continually being lost to the same competitor and the reason behind that pattern isn't yet clear.

How often should Win/Loss Sales Interviews actually be conducted?

Monthly. Regular cadence is what allows patterns to emerge over time, rather than treating it as a one-off exercise done only when something feels obviously wrong.

Who should be interviewed for a Win/Loss Sales Interview?

Customers who went most or all of the way through the sales process, including both those who ultimately bought and those who didn't, since both perspectives reveal different insights about sales effectiveness.

What are these interviews actually trying to uncover?

Sales effectiveness specifically, understanding what worked, what didn't, and why a prospect ultimately said yes or no during the sales process itself.

What kinds of questions work well in a Win/Loss Sales Interview?

Questions like "What was the biggest consideration you based your decision on?", "How well did we tailor our presentation to your needs?", and "What's one thing you'd advise us to change for next time?"