Table of Contents

Deal Win-Loss Analysis Interview Guide

General Best Practice & Guiding Principles

If you hit a gold mine of information during a particular interview, keep drilling deeper. There is not need to ask every question on the interview guide during every interview. It is okay to go off script.
Keep interviews to no longer than 30 minutes.
Strive to have a regular cadence of win-loss interviews; don’t simply run them in periodic bursts.
Send personalized invites soon after deals close to increase response rate and to get fresh information
Know your motivation(s) for conducting win-loss analysis in the first place. Common reasons include:
- Understanding your buyers’ decision making process
- Determining how your competitors position (and win) against you
- Learning about your company’s/product’s reputation in the market
- Optimizing your pricing
- Refining your product roadmap
- Assessing the effectiveness of your marketing programs
Hire trusted 3rd party consultants to conduct win-loss analysis. Otherwise use trained interviewers; most commonly I’ve seen interviews done by product management, product marketing, or sales enablement professionals. Certainly avoid having the sales person or their manager conduct the interview.
- If you decide to do the interview in-house, build trust by going in (1) with people the they know (2) prepared with the feedback they have shared so you show them you know than and can be honest about what went wrong
Seek to interview the most senior yet knowledgeable person possible
Consider offering a generous incentive in exchange for the interview
Interview both wins and losses. Speaking from experience, interviewing only losses is incredibly demoralizing.
Make sure your CEO and c-suite are bought-in to your win-loss program
Be open to interviewing multiple individuals at the buying organization
Generally steer clear of asking interviewees questions with rating scales. This lowers the stature of the interviewer and feels clinical.
Avoid interrupting or correcting the interviewee
Do not sell during a win-loss interview
Do not make this about evaluating the sales person
Record calls where possible. This also help avoid the interviewer having to try to take verbatim notes.

Preparation

Research the interviewee and their company before you speak. This boost your confidence and will help you build rapport that yields better information.
Review all information on the account (ex: account plan) and the opportunity.
Consider speaking with the sales rep before speaking with the interviewee
Offer confidentiality or at least explain how the information will be used

Questions

This is a super-set of questions and is too long for a 30 minute interview. When narrowing down, get stakeholder input on questions.

I’ve labeled this using the letters in MEDDICC plus [O] for ‘Other.’

[O] What was your role in the evaluation?
[O] Which solution did you ultimately choose? (if a loss)
[O] How did you research potential solutions?
- How did you first hear about our company/solution?
- Did you rely on a user review site?
- Did you consult industry analyst research?
[O] Had you used our solution (or the solution that was purchases if lost) before in another company?
[M] How do you intend to measure value from this purchase? (if lost since if won then you should already know)
[E] Who was ultimately responsible for the final signoff on the purchase?
[E] Was this purchase pre-budgeted?
[Dc] Did you define your decision criteria? If so, what were the ‘must-have’ items?
[Dc] What was the biggest consideration you based your decision on?
[Dc] How well did we align with your requirements? How do you feel about our feature set and roadmap? What are we missing?
[Dc] How much was (differentiating feature/s) discussed during the evaluation process?
[Dc] How important was price to you and your team in the first place? If price were not a factor, which solution would you have chosen & why?
[Dp] What was your decision process like? Who ended up being deeply involved?
[Dp] Did you talk to any references, ours or others, about our solution? What did they have to say?
[Dp] What was your experience with our team? At what points did you feel we were too pushy or otherwise rushing you? What could we have done to make it easier to buy?
[Dp] How far along were you in the buying process when we first engaged?
[Dp] What was the most memorable part of the demo/trial experience?
[Dp] How useful did you find our sales & marketing content? How could they be better?
[I] What made you realize you needed this type of solution now? What business problem or opportunity were you trying to address?
[I] How did we do in tailoring our solution to your needs?
[Ch] Who were the most influential people involved in the decision making process?
- Who advocated and why?
- Who opposed and why?
[Co] Who else did you evaluate in your decision?
[Co] What was the biggest difference between us and the other solutions you considered?
[Co] What were the main issues with your prior solution partner?
[Co] How did our pricing (model) compare to our competitors?
[Co] If you were the CEO of our company, what would you do to better compete with other vendors in this space?
[Co] What is our reputation in the industry?
[O] Would you consider our solution again in the future? Why or why not?
[O] Would you recommend our company/solution to others? (though possibly too early to ask this)
[O] What additional comments would you like to share?

Follow Up

Thank the interviewee with a nice gift
Share the information in group meetings since most emails and instant messages will be ignored.
Share cross functionally with Product, Marketing, Customer Success, etc.
- Bake ideas into your product roadmap
- Translate insights into sales enablement incl. onboarding and ongoing training
Make your synthesis visual

Win-Loss Consultants & Tools

(*) = recommended

Avona
Clozd
DoubleCheck Research (part of Klue)
Fletcher CSI
Growth Velocity
Goldpan
Klue
Ox Consulting
(*) PastSight
Primary Intelligence (part of Corporate Visions)
PSP Enterprises
VOC Research

Win Loss Analysis