28 win/loss interview questions

Published Date
July 24, 2023
AI custom autofill
This page has a character count of approximately 3,290 (including spaces).

Launching a win-loss program?

Here are 28 questions to help build your interview guide.

Klue put together a win-loss guide including these and over 20 additional best practice questions. Grab the complete guide in the comments 👇

1️⃣ Questions about the interviewee → to warm them up:

↳ Can you share some background on your role within the evaluation?

↳ What is your experience working with other vendors in this space?

2️⃣ Questions about the drivers that led to their evaluation:

↳ What led you to evaluate [Company]? Why now?

↳ If the incumbent vendor was the issue, why?

3️⃣ Questions to determine evaluation bias:

↳ How did you first hear about [Company]?

↳ What was your perception of [Company] entering the evaluation?

↳ What is your experience working with other vendors in this space?

4️⃣ Questions to determine their buying criteria:

↳ How did you go about requirements gathering? Who was involved?

↳ What were your must-have company and product-specific criteria?

↳ How well did [Company] align with your requirements?

5️⃣ Questions to understand their buying process:

↳ Which vendors did you evaluate?

↳ How did you go about selecting and pre-vetting those vendors?

↳ How did you narrow your list down to a few finalists?

6️⃣ Questions to better understand the buying committee:

↳ Who else was involved in the evaluation process?

↳ What role did each person play?

↳ Did anyone on the committee have a bias toward a specific vendor?

7️⃣ Questions to better understand the demo experience:

↳ Overall, how was your [Company] demo experience?

↳ What were the highlights? Lowlights?

↳ How did their demo compare with the others you shortlisted?

8️⃣ Questions to gather feedback on positioning:

↳ What were [Company’s] key product strengths and differentiators?

↳ Where were the other vendors ahead of or behind [Company]?

↳ If you were the Chief Product Officer of [Company], where would you start?

9️⃣ Questions to gain insight into competitor pricing:

↳ How important was price?

↳ Which vendor had the best pricing model? Why?

↳ Of the vendors you evaluated, which had the best value story (price for the perceived value)?

🔟 Questions to understand how well your sales team performed:

↳ What did [Company's] sales team do well during your evaluation?

↳ What could they have done differently or better?

↳ Where did [Company's] sales team outperform or underperform against the other vendors?

There’s a final “hail mary 🏈” question you should use to close out each interview. One that puts your interviewee in an advisory position.

But you’ll need to check out the full guide to see that. Link is in the comments 👇

#productmarketing #winloss