8 Tips on Conducting Win-Loss Analysis Interviews

I love interviewing people. You learn a lot. Most people are in fact enjoyable to talk with. And, the subject matter is fascinating. I’m not going to give away ALL of my secrets on performing win-loss interviews, but below is a list of what I think are some really important ideas to employ when interviewing people.

1.  Remove as much bias as possible

You want to get respondents to tell you their thoughts – without influencing them to give certain responses. Minimize the use of answer “lists.”  If you provide a list, the respondent might select something that they thought they should have done, instead of what they actually did.  Or the list might be incomplete, missing something important, etc.  In order to determine the selection criteria, ask the respondents to explain what was important to them – in their own words.

You can prompt their memory afterwards by reviewing criteria other respondents have found to be important.  But do that after they give you their criteria.

2.  Get the respondent to open up and relax at the beginning of the win-loss interview

I like to start with open-ended questions about the context of the respondent’s decision – including the business need, the process that was used to make the selection, and the respondent’s role, etc.

For instance, my first question is most often “What motivated your company to look into solutions in this space?” These open-ended questions help your respondent to relax, open up, and start talking. Please, when your respondent starts talking, don’t say a word.  Listen only.  And let them talk as long as they want without interrupting them.  Resist the urge to interject comments or questions. Take notes and ask any clarifying questions after they are done.

3.  Build rapport

Enjoy your time with the respondent. Have a laugh together. Relate to them.

4.  Show that you understand your respondent

Who wants to spend their time explaining a complex thought to someone who doesn’t seem to get it? I like to give an indication with a short remark that shows that I understand and appreciate the respondent’s perspective or experience when they are explaining something.

Do your homework before you begin your win-loss interviewing. You need to be well-versed in the market.  Review the key players and their differentiators.  Read the related analyst reports, competitive documents and the product (or service) descriptions, etc. If you are talking with someone in IT, you need to have knowledge of the technical issues. If your respondent starts talking about their integration architecture concerns and you don’t have a clue about REST APIs, OAuth 2,0, and LDAP – how can you ask the related follow-on questions to probe more deeply into the technical issues?

Similarly on the business side, you need to be able to speak the language of your respondent, and engage with them on their concerns.

5.  Be interested in what your respondent has to say

If a respondent says to me “the sky is green”, I might follow up with, “Hmm… that’s interesting, why is the sky green”? Again, you need to be conversant and interactive with your respondents if you expect to learn anything from them.

6.  Get both qualitative and quantitative data

To be most effective, you need both qualitative and quantitative data. Purely qualitative interviews have value, but they lack the ability to prioritize the importance of the information.

For example, you need to ask for the scores of each vendor across the criteria. “And for Company-X, how would you score them on ‘Ease of Use’”? Without scored responses, it’s very difficult to do a detailed, non-subjective analysis.

7.  Ask my favorite question

I often ask this question towards the end of the interview. “If you were meeting with the senior management from each of these vendors, what would you tell them they need to do in order to improve – and to better meet your needs?“

8.  Make sure you are courteous, prepared, and professional.

You only have one shot… So get it right the first time.


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