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Why every product marketer should run win/loss interviews (and 5 steps to run your own)

Updated: Oct 27, 2019



You win some deals, you lose some. Does your marketing team ever pause to ask why?


Often as marketers we get caught up in our own assumptions about how customers should view, value and purchase our products. Unfortunately, that perception doesn’t always align with our buyer’s reality.


Running a win/loss analysis is one of the most cost-effective ways for your team to make sure that you and your prospective buyers are on the same page. Yet, only 20% of marketing teams do it.


This post will help you understand what you can learn from a well-designed win/loss program and five simple steps you can take to run your own.


What you’ll learn from win/loss interviews


There's no shortage of insights that you can uncover through win/loss interviews. The discussions you have with customers you won and prospects you lost throughout the sales cycle can help you answer critical questions like:

  • How do buyers actually buy?

  • Are you attracting the right kind of customer?

  • What are the main reasons someone chooses you over a competitor?

  • What are the main reasons someone chooses a competitor over you?

  • Are there competitive alternatives your team was unaware of?

  • What is the main value buyers think they’ll gain from your product?

  • Which marketing messages and channels do your buyers respond to?

  • Are you priced competitively?

  • What are some of the problems that your product can’t currently solve?

The questions asked will vary from team to team and heavily depend on the type of insights you'd like to uncover. For example, if your marketing team wants to fine-tune their value propositions, you may lean into questions around perceived value. If your product team is fine-tuning their roadmap you may lean into questions that help them identify priority features that could help your team close more deals.


5 steps to build your own win/loss program


The good news is, building out a thoughtful win/loss program doesn't have to be difficult. Here are five steps you can take to create your own.


1. Determine the goals of your program


The most critical step of your win/loss strategy is determining what the goals of your program are. Having a clear understanding of the type of insight you'd like to gather and how you'll action that insight when you have it will make it easier to decide which questions you'll ask.


Pro tip: Make sure stakeholders from departments that will benefit from the insights you'll gather are included in this stage. Some groups you'll likely want to include are product, marketing, sales and success.


2. Finalize your question list


Once you have a solid understanding of what you'd like to learn through your win/loss interviews, you'll want to develop a set of questions to guide your discussions. This list should include 10-15 questions that help you uncover information you identified in your program goals. If you need some inspiration, we love this list from HubSpot.


Pro tip: Use your questions a guideline for your conversation. Don't be so focused on answering every question that you miss out on other valuable insights you could unlock with thoughtful follow-up questions.


3. Decide which buyers you'd like to interview


Next decide which buyers you'd like to have a discussion with. To get the best mix of results you'll want to focus evenly on wins and losses. Including too many of one or the other will cloud your results. The number of buyers you should interview varies, one study suggests 2 interviews for every ten pitches. Pro tip: Don't wait too long to compile your list. You'll want to be sure to reach out to new customers and lost prospects roughly 3 weeks after they've received your final sales pitch. Their interaction with your team and product will still be recent enough to remember.


4. Schedule your interviews


Once you know who you'd like to reach out to and what you'll ask them, formulate your ask. Draft up an email you can use to ask for 30 minutes of their time. Be clear that it is not a sales call, you're just trying to learn more about their experience with your team and product. When you do have a chance to connect, be genuinely curious about their experience and use your questions to guide the conversation.


Pro tip: Ask the person you're interviewing if you can record your conversation. This allows you to focus on listening instead of trying to take notes and track responses. Plus, revisiting the conversation later can pull out new insights you may miss in the moment.


5. Host a debrief


After you've hosted your calls and reviewed your findings, share them with the stakeholders who helped you define the goals of your win/loss program. This is where you can turn insights into actionable outcomes for your team. Talk about what you've heard and trends you've observed. Ensure that every team has at least one takeaway from your debrief that they can action.


Pro tip: Win/loss programs are most effective when they are performed at a regular cadence. Even though you've come to the end of your first round of analysis, it should be something that becomes a part of your ongoing strategy.


Love everything you've read, but just don't have the bandwidth to take on a win/loss analysis? Our team can help! Let us know a little bit more about your project using the form below.


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