<img height="1" width="1" style="display:none" src="https://www.facebook.com/tr?id=1126373844873041&amp;ev=PageView&amp;noscript=1">
Ryan Sorley, Founder & CEO
Ryan Sorley, Founder & CEO Posted on May 23, 2022

9 Steps to a Successful Win/Loss Program

The goal of research is to get at the truth. More to the point, research isn’t about truth for truth’s sake. It’s about uncovering truths that your team can use to meet their objectives more efficiently and successfully.

There are a lot of things that keep B2B organizations from achieving their goals: product gaps, poor sales performance, pricing confusion, and many other challenges. What you need is an effective way to get at the people who know the truth about the root causes of these challenges. 

Who can give you the truth you need?

Your customers.

A well-designed win/loss program is an invaluable way to get at the unfiltered truth about why some things work, and others don’t. It can help you identify weaknesses and opportunities in every area of your business. 

The key to a successful program is to build it with the end goal clearly in mind. Start with the destination, and then reverse engineer your approach to ensure that the work you do will, in fact, deliver the exact results your internal stakeholders want and need. 

In this article, we’re going to go through a nine-step process that will help you:  

Ready? Let’s go! 🚩

1. Download Your Program Design Worksheet

The first step in this process is an easy one: download our free Program Design Worksheet, which we developed specifically to help you organize all the key pieces of information that you will need in order to build a successful win/loss program right out of the gate.

2. Select Your Stakeholders

You need allies to help you design a successful win/loss program, and those allies are your internal clients, your “league of stakeholders.” These are the people who will help you understand exactly what information you need to uncover in order to empower different functional areas within your organization to level up their efforts.

Stakeholders come from a variety of different teams: 

  • Sales Leadership is eager to understand how their sales team is doing out in the marketplace. Are they able to handle objections, differentiate your products and offers? Are they able to talk about pricing in a very transparent, clear, and concise manner?
  • Customer Success wants to know why people are or are not renewing. They also want to know, if somebody doesn't renew, whether there was anything customer success could have done differently to prevent a churned account.
  • Product Marketing is super interested in anything having to do with go-to-market messaging, reputation, and branding. 
  • Competitive Intelligence is looking for any information you can collect on your competition — their products and services, pricing, positioning, and how their sales team is going to market.
  • Product Management can benefit from information about gaps in your solution or future roadmap. They are looking for something that might strategically inform the direction of future development efforts.

Action Item: Select your top five stakeholders 

Typically, product marketing will be your primary stakeholder, but which other groups and individuals should be in the mix? In addition to the core groups mentioned above, you might choose someone from senior leadership, a VP of pricing, or someone in strategic operations. Which people are most relevant to your efforts depend on the size and structure of your organization as well as who cares most about collecting insights from win/loss data and putting them to good use. Once you’ve selected these folks, add them to your Program Design Worksheet.


3. Do Stakeholder Discovery

Once you have identified your stakeholders, it’s time to get inside their heads so you can align your program with their actual needs. Only by knowing what questions are keeping them up at night can you provide answers that they can act upon. 

A great way to kickoff a stakeholder conversation is with this fill-in-the-blank exercise. Ask them to complete this sentence: 

If I knew _____________, then I could __________, which would result in __________.

Defining these three elements are a powerful shortcut to get to the heart of the information your win/loss program needs to uncover:

  • If I knew — This gets your stakeholder to think about exactly what information they are missing and wish they had — the blind spot, if you will, that keeps them from understanding the best way to move forward.
  • Then I could — This defines how having that missing piece of information could empower the stakeholder and their team. For example, if your stakeholder is a product marketer, how might they be empowered by understanding what materials people are using or which criteria are most central to product evaluation, or where they are going for advice? 
  • Which would result in — This defines the ultimate value or ROI of the uncovered truth — the goal the stakeholder could achieve. 

Example statement for Sales Leadership

If I knew where my team was struggling, then I could provide the exact support they need, which would result in a higher win rate.

This exercise will help you quickly capture what’s truly most important to each stakeholder in terms of their mission and the specific outcomes they want to achieve. And, as a bonus best practice, after you’ve completed the first round of research, you can circle back with each stakeholder to compare what they shared in discovery against the action they took based on research insights. Measuring the results of their research-informed actions can go a long way toward demonstrating the value of your program in very concrete terms.

Action Item: Schedule Stakeholder Discovery Conversations.

Reach out to each stakeholder, and spend time with them working through this exercise. It may seem simple, but you’ll get a lot of really interesting insights and goals.


4. Identify Stakeholder Learning Objectives

A learning objective is what a stakeholder hopes to learn from the win/loss interviews and data collection. You identify a learning objective by turning the “If I knew” statement into an objective. In the above Sales Leadership example, the objective is to learn where the sales team is struggling. 

Some other example questions to dive deeper into the learning objectives conversation are:

  • What are you hoping to learn through a win-loss program? 
  • How do you personally plan on using the program findings?
  • What do you believe are the biggest barriers to the company's greater success? 
  • What are the primary benefits (or perceived benefits) buyers seek to gain through our offering? 
  • What are the top sales and product-related questions you would like answered? 
  • What are your high-level assumptions about our competitors? 

Action Item: Once you have identified your program learning objectives, enter them into your Program Design Worksheet.

Remember that each stakeholder will likely have their own learning objective(s), and you should capture all of them.


5. Craft Objective-based Questions

One of the critical keys to doing effective and aligned win/loss research is to make sure that you’re asking the right questions. Asking random why-we-won-or-lost questions isn’t going to get you the information you and your stakeholders need. Instead, you want to design your questions around unearthing the specific details that will inform the learning objectives that will ultimately help each stakeholder achieve their goals.

Side note: While it’s important to develop your questions ahead of time, they aren’t meant to be read verbatim during an interview. These questions are meant as discussion guides. The goal is to keep the conversation natural and organic instead of rigid and scripted. You want to be very flexible and allow opportunities to follow an interviewee’s lead so you can probe more deeply with second- and third-level questions. Don’t be afraid to ad lib in response to the real-time conversation. Win/loss interviews are a great time to engage your improv skills.

For example, in pursuit of insights to help Sales Leadership gain a better understanding of where the sales team is struggling, you might ask, “How was your sales experience? Tell me a bit about that.” Initially, the buyer might only share some high-level observations, but listen for opportunities to ask more with follow-up questions like, “Can you tell me more? Why did you say that? What could we have done differently or better?” In such a case, they may tell you that they had an awful experience, at which point you’re off to the races. You already have some really valuable information to bring back to your stakeholder about areas of opportunity.

On the other hand, you definitely don’t want to go into an interview with a bunch of witch hunt-type questions. You also want to create opportunities for positivity. So, for example, you might ask, “What did the team do well?” This gives you a chance to capture the team’s strong points. 

Sometimes, it’s helpful to have the buyer step into the shoes of the salesperson’s boss with a question like, “If you were the VP of sales, what two or three pieces of advice would you give your people to help them do better?” Positioning the question in this problem-solving structure can inspire some really interesting and creative feedback. In general, open-ended questions like this one can be really illuminating. 

Action Item: Brainstorm specific objective-based questions that will help you get at the heart of each stakeholder’s learning objective, and add these to your Program Design Worksheet.

Remember that each stakeholder will likely have their own learning objective(s), and you should capture all of them.


6. Define Your Drill Down Areas

One of the challenges of doing effective win/loss research is figuring out how to sift through and summarize all your interview content so you can pull out key points and identify trends. To set yourself up for success, we recommend that you spend some time thinking about what kinds of things you expect to hear from buyers in relation to your defined learning objectives. 

Thinking in advance about what themes you might encounter will make it possible for you to start figuring out what text tags you’ll need to use during your textual analysis of the transcript data. It’s likely that once you get into text coding you’ll need to assign new codes, but it’s to your advantage to lay the groundwork early on so you don’t feel like you’re starting from scratch. 

For our Sales Leadership example, some possible text tags might be:

  • Positive experience
  • Negative experience
  • Knowledgeable
  • Customer-focused
  • Responsiveness
  • Listening Skills
  • Communication Skills
  • Objection handling
  • Professionalism
  • Aggressive/pushy
  • Transparency
  • Price negotiations

Tagging taxonomy is crucial because without it, qualitative data is next to worthless.

Here at DoubleCheck we approach tagging taxonomy using a four-step process:

  1. Identify high-level topics/categories aligned with the interview guide. (That’s the example above.)
  2. Where appropriate, break out those categories by sentiment. 
  3. Define a set of standard tags that can be used across multiple projects (typically approximately 5 to 7 tags per category).  
  4. As the research sample grows, add additional levels of tags as needed. 

Action Item: Select three or four core themes to add to each learning objective in your Program Design Worksheet.

7. Conduct, Record, and Transcribe Your Interviews

Conducting effective win/loss interviews is part art and part science. We’ve built more than a hundred win/loss programs. Between our hands-on experience and the third-party research we’ve done, we have a lot to say about what makes for a great interview. We have several in-depth articles that focus solely on how to really nail your win/loss interviews, but here are a few high-level tips:

🤓 Do your prep work:

  • Determine your incentives
  • Establish your authority through prior research
  • Use a pre-interview online survey
  • Create a conversational interview guide

🙇 Get in the right mindset:

  • Free yourself from the script
  • Develop your own empathetic conversational style
  • Be conversational and authentic
  • Be interested and curious

💥 Ask the right questions:

  • Choose warm-up questions that invite the interviewee to talk about themselves 
  • Stay aligned with your learning objectives
  • Structure the conversation along the buyer’s journey
  • Strike a balance between specific and open-ended questions

🏄 Manage the conversation like a pro

  • Make a strong, clear start
  • Find a connection early in the conversation
  • Practice active listening
  • Identify and work with the interviewee’s response style
  • Be fully present throughout the interview
  • Be a confident and active participant in the conversation
  • Follow the 10/90 rule, but remain in control
  • Never contradict the interviewee
  • End strong

You will obviously record each of your interviews, and then you can have the recordings transcribed. There are many software tools, apps, and services you can use for transcription. Many video conferencing platforms offer their own transcription features, or you might choose a third-party service that uses either AI or human transcriptionists. We have had great success with Rev. They are not the least expensive option, but accuracy is critical for us, and Rev’s transcripts are highly accurate.

Action Items: Learn more about how to run a great interview, and choose your transcription tool. 

It takes practice to get really good at doing win/loss interviews, but no matter what level of experience you have, it’s always helpful to brush up on core skills. Check out some of our articles on interview excellence: 


8. Analyze Your Data and Report Your Findings

For some people, data analysis is the fun part. For others, it’s really challenging. Either way, this is a critical part of the process. It’s where you look through all your unstructured data and pull out the really interesting nuggets in a meaningful way, emphasis on “meaningful.”

At DoubleCheck Research, we use a tool called Dovetail. We have found that it’s the best way to take all the qualitative, unstructured win-loss data we collect on behalf of our clients and create highly informative reports, summarize those reports, do text analysis, and then use the insights we gain to help clients understand exactly which themes are trending in areas like sales performance, product feedback, competitive intelligence, and so forth. It’s honestly been a game-changer for us.

You can read more about exactly how and why we use Dovetail, but—in short—Dovetail helps us wrangle data from many disparate sources—interviews, win-loss interviews, churn interviews, customer experience interviews, Zoom recordings, transcripts, analyst reports from Gartner/Forrester/IDC, social feeds, competitive battle cards, etc.—into a consolidated knowledge base. Dovetail is also essentially creating an entirely new research dynamic—push-versus-pull research—that focuses on building a research repository that makes specific insights and data readily accessible to whomever needs them, whenever they need them.  

Once you’ve done your analysis, you will need to create narratives and visuals that make the insights easily accessible to your stakeholders. Many analysis tools, like Dovetail, have features that make this a quick-and-easy part of the process. 

Action Item: Start doing some research to explore which tools you will use to analyze the data. Also, revisit the tagging taxonomy you developed in Step 6 - Define Your Drill Down Areas - to make sure the tags you've defined will allow you to fully analyze your data. 

9. Capture Stakeholder Value

Finally, after all the work you’ve done to get to this point, you’re ready to present your findings to your stakeholders. This is the opportunity to engage in a different kind of stakeholder conversation, one that circles back to the original learning objectives while simultaneously delivering the insights that will help them achieve those objectives. 

For instance, in our Sales Leadership example, perhaps the insight is that the sales team struggles during price negotiations. Based on that finding, Sales Leadership can confidently pursue the creation of tools, trainings and role-lays that will help the team be more effective during that part of the sales conversation. And that should, in turn, result in a higher win rate and happier customers.

Action Item: Identify your best opportunities to share findings with key stakeholders. This might be a quarterly meeting, a sales enablement event, or a dedicated workshop.

If you’d like some helpful tips on how to run a productive presentation or working session, check out Win/Loss Workshops: Five Steps to Turn Program Insights into Action.

Ready to get started? 

Those are our nine steps to a successful win/loss program. If you follow this structure and process, you will be well on your way to designing a really strong program that will align with stakeholder learning objectives and deliver exactly the insights and truth that your organization’s team leaders need to achieve company-wide goals. 

If you are ready to get started, take that first step by downloading our free Program Design Worksheet, and then select a few recent deals to interview. 

The truth is out there, and it’s your job to find it.


Want to see 
DoubleCheck in action?