When doing Win/Loss interviews, there’s one big distinction that pops out right away. And that’s the difference between a win interview and a loss interview. In this article I’m going to run you through all the key differences between the two interviews and identify the different types of questions you can ask in each. 

Some questions are exactly the same across win and loss interviews

In a win and loss interview you’re going to ask about certain topics like pricing, product and the sales experience in very similar ways. In fact, questions on these topics are pretty much the same across win and loss interviews. Differences only occur when one of these topics is a reason for the win or the loss itself. And even then, the reasons people give you for a win or a loss are answers to a different question. They’re an answer to the question: “why did you decide to move forward (or not) with us”. At a later point in the interview you’ll usually ask specifically about pricing, about product and the sales experience (“how was your experience with the sales person?”). These questions tend to be exactly the same across win and loss interviews.   

Questions you only ask in win interviews

The obvious answer to this question is that you’re going to be asking why they chose your product instead of why they didn’t choose your product.  But in addition to that, the thing to remember about a win interview is that when you win a customer it breaks open a bunch of new experiences for this person. They’re going to go through an onboarding experience, they’re going to touch support, they might have some churn risk you want to capture, etc. Let’s go through all the question areas that are unique to win interviews:

• Onboarding Questions
  If you’re like most companies, a win interview participant will be going through an onboarding process into your product. When scheduling a win interview there’s a sweet spot that occurs when the customer new enough they still remember all the reasons they chose you, but they’re a mature enough they’ve fully onboarded into you product, so you in addition to questions about why you won you can also learn about how onboarding went for them. It depends on the length of your onboarding process, but we’ve found that people tend to remember most of the reasons they chose your product for at least 3-4 months after the deal closes. So if you can, schedule your wins to capture both reasons won and onboarding data. 
  
  Onboarding feedback tends to vary widely amongst our clients. Companies that have a very in-depth migration and onboarding experience have customers with a lot to say about onboarding. If you’re one of those companies, a great way to tee up these questions is try to break the feedback into what went well during the onboarding process, and what didn’t go well in the onboarding process. If onboarding requires a lot of work from the customer, people will have a lot to say.
  
  If onboarding into your product is pretty easy and straightforward, what you’re looking for isn’t about what’s gone well and what hasn’t because if the process is simple, people won’t have much to say about it. Rather, you’re looking for indicators in the onboarding experience that tell you whether they’re going to be an active user of your product in the future or not. You want to assess things like “now that you’ve had a chance to use the product, what challenges are you facing”. Are their teammates having trouble getting into the product? Is the product delivering on what it promised? If they’ve breezed through onboarding then the next question is about value - is this delivering value to them the way they expected, or not.
  
  
• General challenges
  Win interviews usually have enough experience in your product to have accumulated a few pain points. So asking about “general challenges” or pain points they’ve experienced tends to be a very fruitful part of the conversation. In general, when you get into a Win/Loss conversation the problems people have with your product tend to be the most animating part of the entire conversation. We try to position questions about challenges about 5-8 minutes into the conversion so that the participant has had enough time to fully relax and open up, and also because its important to get to this type of question sooner rather than later because people are usually secretly waiting to tell you what they don’t like. When they got the original invitation have an interview it’s very likely that the pain points they’ve had with your product are the first thing that came to their mind when they thought about providing feedback. We typically structure this question as a “top 3”, so the question gets phrased as “what are the top 3 challenges or pain points you’ve had with our product. That tends to get them thinking about how best to organize what they’re about to tell you, and gets them thinking about at least 3 pain points. If you don’t provide a similar type of structure in your question people will often times only give you a single pain point when in fact they have quite a bit to share, they just need to be primed in the question correctly.
  
  
• Did they have an Aha! Moment
  In a win interview, the best way to define and Aha! Moment is a moment where everything suddenly came together and they saw the value of the product AND they thought hmm, this might be the right product for us. Interestingly, this is also a good question to ask in a loss interview but where this question leads in a win vs a loss are two different places. In a win interview this moment is key for understanding why and how the win occurred. In a loss interview this moment is key for understanding where they see the most value in your product and for potentially acquiring at some point in the future. 
  
  
• Questions about support
  Most of the time win interviews have had some experience with your support team, and loss interviews have not. A win interview is a great opportunity to ask them questions about their experience with support and learn what went well and what didn’t. Typically when we ask about their experience with support we ask 3 different questions. First, have they had any experience with the support team. Usually that elicits a response that tells you whether they have any experience to share, and a bit about what that experience was. From there you can dive into breaking the experience into two categories: what went well in their support experience, and what they think the support team could improve on. Normally “what went well” in their experience is pretty light. They’ll say things like “they were quick to respond” and “they were knowledgeable”. What you’re really looking for is what didn’t go well. In that direction you’ll find interesting stories and valuable insights that will be actionable. People tend to remember them much better as well, so the information they share will be much richer.
  
  
• Ask how they’re feeling about the future
  Ask them how their experience has gone with you so far, and how they’re feeling about the future. What you’re looking for here is some predictive information on whether or not there’s some churn risk in the account. We usually ask them “where they see themselves 2-3 years from now. Are you a) definitely still using our product, b) definitely not still using our product or c) somewhere in between. If they answer “b” or “c” to this question you’ve got meaningful churn risk in the account. You can then follow up with questions about what would need to happen to keep you happy and maximize the odds of staying with you when their renewal comes up. 

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Questions you only ask in loss interviews

The obvious answer to this question is that you’re going to ask the participant why they decided not to move forward with you. This question is the most important question in a Win or Loss interview because ultimately you’re trying to figure out why you lose deals, and to plug those holes. When you ask this question try to structure it in a way that will get you at least 3 reasons for their decision. We usually ask something like “what are the top 3 reasons you decided not to move forward with us”. Here are some additional questions that you should ask in a loss interview but not necessarily a Win Interview.

• Which competitor they chose. In both a Win and a Loss interview general questions about the competition should be asked. In both types of interviews you’ll want to find out which competitors they considered, and then run through strengths and weaknesses of each competitor.  But in a Loss interview they most likely chose to move forward with one of the competitors. Make sure and ask which competitor they decided to go with, and then ask specifically about why they chose that specific competitor. There’s a subtle but important difference between asking about the strengths of a specific competitor, and the reason they chose that competitor. Obviously why they chose that competitor is also a strength, but if you can, it’s really valuable to accumulate the specific reasons why a competitor is beating you, and not just their strengths. A Loss interview is your opportunity to start building out the competitive profile you need to understand how your competition beats you.
  
  While you’re talking about which competitor they chose, another great question you can ask them is how it’s going with that competitor. We’ll typically ask something like “now that you’ve been using [competitor], what’s your view on the strengths and weaknesses of [competitor]?”. If the participant is comfortable enough with you they’ll usually share quite a bit of information about how it’s going, and they won’t shy away from telling you what they don’t like about them. If you can get them talking in this section, what they share will become high-value information for how to potentially win them back 6-12 months down the road.
  
  
• Did they have an Aha! Moment
  This question is actually the same between a Win and a Loss interview, but in a loss interview you can use the answer to understand the likelihood of winning them back at some point in the future. Keep in mind that all losses are potential wins in the future, so a loss interview is partially about building a roadmap for how to win them back when the time is right. If they did have an Aha! Moment, it’s really helpful information to know when the salesperson is speaking with them again 12 months from now. Anything that they find valuable about your product are details a salesperson can utilize to move them closer to a win.
  
  
• If they’re open to considering you again in the future
  A Loss interview may still be open to considering you again at some point. Make sure and ask this question so you can accurately gauge the likelihood of re-engaging at some point. We normally ask this question towards the end of the interview and people tend to be pretty honest. If they are open to using you in the future, gather the details about what would need to happen for that to occur.

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We normally ask about 10-15 questions in each Win and Loss interview. Many of the questions are exactly the same for both interview types, but as you can see there are nuanced but important differences between them. To keep these differences in mind when you’re conducting your interviews, it’s a good idea to create two separate interview guides - one for Win interviews and one for Loss interviews. That way you’ll not only ask all of the questions you intended to ask, but you’ll also be asking them to the right person. 

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