Conducting Win/Loss Analysis

What is win/loss analysis?

It is a data-driven approach to understanding business performance – It is a methodology for identifying the key factors that cause a company, (typically B2B), to either win or lose deals. It allows you to rely on data rather than preconceived theories or hypotheses to understand the drivers of success and failure. The aim is to come into the process with an open mind, using the data gathered to generate theories. This bottom-up or inductive methodology is crucial to the success of the analysis.

It helps companies gain a deeper understanding of their strengths and weaknesses – they can then use this knowledge to improve their strategies and ultimately increase their success rate.

What are the different phases of a win/loss analysis project?

Phase One: Planning – set a goal for the win/loss analysis project. It should be more pointed than simply decreasing your losses. Losses at which stage in the pipeline? For which product? Which market segment? Create a question set for your win/loss interviews, and look at any preexisting customer data in your CRM.

Phase Two: Outreach – reach out to recently closed deals that fit the cohort you identified in Phase 1. Consider participation rates fluctuating between wins and losses and you may have to offer incentives.

Phase Three: Interviews – conduct an initial batch of interviews (typically ~20) to kick off the project and accrue some initial qualitative findings that will inform the direction of the rest of your research.

Phase Four: Analysis & Recommendations – synthesize the data that you’ve accumulated during customer interviews, and create a final report with recommendations on key actions to improve your approach that are informed by your analysis data

Phase Five: Make Improvements – engage with Sales, Marketing, and Product leaders to make priority improvements based on your buyer insights.

Phase Six: Survey Launch – leverage a survey to efficiently track the impact of your improvements, moves by competitors, and evolving buyer decision-making. Continue to run win/loss interviews in parallel with the survey.

**Why do you need to talk to both your wins and your losses? What do you learn from your wins vs. your losses?**

Whatever is causing losses might also lead to wins – if you offer a point solution that does one thing very well, you might have wins who tell you they chose you for that best-of-breed aspect, and losses who say they didn’t choose you because they wanted a broader suite or platform solution. In order to understand the overall impact of any given trait on prospects, you need to understand the perspectives of both wins and losses.

Identifying what you’re doing right is as important as understanding what’s wrong – It’s natural to want to focus on losses and figure out what went wrong. However, it’s equally important to understand what you’re doing right so you can build on that. You don’t want to inadvertently change aspects of your offering that are working well for you with current customers, be it product capabilities, positioning, or pricing.

Understanding wins actually helps you understand why you’re losing – it requires subtle analysis, but you can’t fully understand why you’re losing until you know what’s driving your wins. It helps you understand the gap between what makes a win and a loss. If you only look at losses, you might get a skewed perception of what’s driving your business.

It helps you avoid making changes that could negatively impact the companies you win – looking at both wins and losses gives you a balanced view of your business. It helps you understand what’s working, what’s not, and how you can improve.

What deliverables will you create as part of win/loss reporting? What will they tell you?

Post-Interview Deliverables
Deliverable	What it is
Immediate Post-Interview Summary Report	After each interview, a summary report is created to capture the key feedback and learnings. This report includes a 5-10 sentence “quick take” summarizing the main points and key takeaways. This quick take is typically shared with clients via communication tools like Slack or Teams for immediate feedback.
Win/Loss Portal	A win/loss portal serves as the repository for artifacts from each interview. All program materials for each account are available on-demand, such as the summary report, transcript, recording, and any sales team notes from the CRM. This portal allows interested stakeholders to drill down into the details of each interview.

Post-Project Deliverables
Deliverable	What it is
Comprehensive Analysis and Reporting	Once a full set of interviews has been completed, a comprehensive analysis and report is created. This report aims to answer two main questions: what’s driving the win/loss outcomes, and why are these particular factors influencing outcomes?
Quadrant Report	A quadrant report is a visual tool that shows the prevalence and impact of drivers of win/loss outcomes. The top left quadrant contains the most prevalent reasons for losing, while the top right shows the most prevalent reasons for winning. This report goes beyond simply counting how many times a factor came up in interviews, it also shows how strongly each factor is associated with winning or losing.
Buyer Quotes	Relevant buyer quotes provide the context you need to take action. Take price for example. Use quotes to explain what buyers are looking for, and their assessment of your pricing vs competing offerings’ pricing.
Recommendations	The final and arguably most important deliverable is a set of recommendations. These recommendations are based on patterns observed across multiple interviews and provide actionable advice for improving performance in key areas.

Sample Quadrant Report

For more on win/loss analysis deliverables, see our blog post here.

Who should be responsible for win/loss reporting? Who will use the findings?

Typically, Product Marketing is the owner of the win-loss analysis process – they lead internally, whether the process is conducted in-house or contracted with a service. They take the lead on developing the win/loss plan and managing the program.

Contributors include:

Sales leadership – to understand how sales execution, product capabilities, and marketing programs are affecting wins and losses. Competitive insights and opportunities for coaching and training are also a top interest.
Product Management – needs the big picture of what’s driving outcomes with new accounts, rather than focusing on individual situations (“specials”).

Third-party providers are often used in four scenarios:

When there’s a lack of preexisting detailed customer information – when closed reason codes and notes from the CRM lacks enough detail to act on, third-party providers can provide a deeper understanding with buyer interviews.
When bias affects interview quality – bias and assumptions that color internally run interviews can be reduced with an independent interviewer.
When interviewing losses is overly burdensome – interviews with losses can be challenging to source. Third-party providers can increase the participation rate among buyers from lost deals.
When it’s time to scale the win/loss program – a successful program will be scaled up to answer additional questions. Outsourcing to a third-party provider takes the burden off internal resources.

The benefits from the analysis extend across the entire organization – the findings can help improve differentiation and targeting, inform the product roadmap, and provide valuable insights for sales process and execution. The individual interviews can also be beneficial for coaching individual sellers.

What data sources should you look at before reaching out directly to conduct interviews?

Use pre-existing data in your CRM – most companies record loss reasons in their CRM. After a deal is closed, the rep or AE uses a drop-down menu to choose a reason for the loss (or win). They may also enter some notes to support their input. Firmographic data in the CRM can also help identify trends such as whether you’re winning more or less in particular industry segments, market segments, or against a particular competitor.

Use the sales team’s deal reviews – most teams with a complex sale will review the key that drove a win or loss outcome. This can serve as a good starting point for understanding the factors driving outcomes, and where there are gaps in understanding.

What research methods should you use? How might you use surveys vs. calls?

A mixed methods approach (of survey and interviews) yields the best results – this combination of qualitative and quantitative design often develops the most useful insights. Starting with a baseline set of ~20 deep-dive interviews can provide a solid foundation that you can back up with a survey.

After the initial interviews, run a survey and interviews simultaneously – this increases efficiency once you’ve used the initial batch of interviews to better design your survey. A parallel research approach allows for continuous data collection, which is crucial in fast-changing markets like technology.

Using mixed methods is more cost-effective (especially as you scale) – it becomes cost-prohibitive to conduct interviews for all opportunities. Each interview has lots of variable costs, while surveys have low variable cost. We’ve calculated that if you want to debrief 10 opportunities per quarter, a mixed methods design is 17% cheaper than conducting interviews alone. If you want to debrief 15 opportunities per quarter, a survey-interview combination is 44% cheaper than an all-interview approach. As the number of opportunities grows, the cost-effectiveness of the mixed methods approach becomes bigger.

How do you choose which wins/losses you reach out to?

Your business goal will define your sample – it’s not enough to simply aim to improve your opportunity win rate. You need to specify which product, use case, or market segment you’re focusing on. Your products, pricing, and competitors will vary between different offerings and market segments. Therefore, the decisions your buyers make will also differ.

Select a clean and consistent cohort – having a targeted cohort not only helps in comparing your offerings against competitors but also aids in securing resources and funding. If you can specify your goals, such as increasing win rate or velocity in mid-market deals for product A, you’re more likely to get uptake within the organization.

The sooner you can conduct the research after a deal closes, the better – defer to your sales team to decide how soon is too soon. You want the buyer’s focus to be on the pre-sales experience, not the onboarding or implementation process. As a guideline, look back one quarter and include any new deals that close during the project.

Even with lost deals in a nurture campaign, there’s value in learning from them – They can provide invaluable “winback” insights for re-engaging with them in the future. However, always work with your sales team to determine whether a deal is available for research.

Automate CRM reporting of recently closed opportunities – set up an automated report in your CRM to know which opportunities have closed, whether they won or lost, and what the last stage was before the loss. This can all be automated, but always check with the sales rep before reaching out to a deal. They may want to hold off for various reasons, such as a potential upsell situation.

How do you get losses to talk to you? Should you offer an incentive to participate?

The initial request should come from the AE that the prospect worked with – this is particularly effective in late-stage deals where a relationship has been established. The participant is more likely to respond to someone they’ve been working with for a while. This can increase participation by 10% over an email from a sales, marketing, or product leader in your organization.

A rule of thumb for lost deal incentives is 2-3x the champion’s annual salary on an hourly basis – you can offer monetary incentives to losses to increase participation. These should be geared towards the expected salary of the participants. Offering 2-3x their annual salary broken down to an hourly rate ensures the incentive is attractive enough to catch their attention. In some cases, such as government roles or in Europe, financial incentives may not be accepted. Consider offering a donation to a charity of the participant’s choice.

Keep the initial email communication concise and compelling – the initial email should be short but compelling. It’s important to explain why the feedback is important to the company and how it has been used in the past.

Make scheduling easy – use tools like Calendly to make it easy for participants to schedule their feedback session. This eliminates the need for back-and-forth emails to find a mutually convenient time.

Follow up on an email with a phone call – after sending an email, follow up with a call. Even if you end up leaving a voicemail, use this opportunity to convey the importance of the feedback to the company.

Wins should participate without an incentive – they should have a vested interest in your company. Reminding them of this, and the fact that their feedback can impact product leadership and roadmap decisions, can be a strong reason for them to participate.

How many data points do you need? How many wins vs. how many losses?

Aim for a sample size of 20 representative companies. – if your goal is to improve your win rate in a specific market or against a particular competitor, your cohort should reflect that. This number allows for a good balance of wins and losses and provides a solid basis for analysis. While it may be tempting to reduce the sample size for cost or time reasons, a smaller sample may result in less clear patterns in the data.

Sample size recommendations can vary – recommendations for interview sample sizes can range widely, with some suggesting as few as eight or ten for a win-loss analysis. However, the binomial probability formula suggests that to have an 85% chance of identifying an issue that appears in 20% of your deals, you need to interview 9 sales opportunities.

Balancing win and loss sample sizes simplifies analysis – keeping an even ratio between wins and losses in your data set simplifies the analysis process. This balance allows for a clear comparison between wins and losses at a 50% overall win rate.

What should you expect your participation rate to be among those you reach out to?

Historical participation rate varies – the pandemic may have impacted the participation rate positively. In recent years, we’ve seen historical participation of:

	Wins	Late-Stage Losses
2023 Participation Rates	80%	47%
2022 Participation Rates	76%	33%
2021 Participation Rates	82%	59%

Note: participation rates vary by company – some companies achieve a participation rate as low as 10%, which can have a significant cost, especially for smaller companies with limited opportunities. If a company only has 20 opportunities closing per quarter, a 10% participation rate translates to just two interviews each quarter. If the company aims to secure 10 or 20 interviews, it could take five to 10 quarters to achieve this goal, which is far from ideal. Overall last year, 63% of the buyers we contacted agreed to an interview.

How do you decide what software you should use?

Phase	Tools
Outreach Phase	• Sales engagement software – e.g. Groove, Salesloft, or Outreach. These are likely already integrated with your CRM and can be set up to automatically send emails when a deal has closed.
Interview Phase	• Communication platform – e.g. Zoom, Teams, or Google Meet • Calendaring tool – e.g. Calendly. • Transcription tools – e.g. Otter.ai and Sonix. For more on how automated transcription tools can now outperform human transcription, see our blog here.
Analysis Phase	• Repository and analysis platform – e.g. Dovetail, Condens, or EnjoyHQ. • AI is reshaping the analysis and reporting phase – dozens of AI-based analysis tools have entered the market recently, and the platforms above have also added AI capabilities to assist with analyzing and making sense of interview data.

Adopt a best-of-breed approach when choosing software for win-loss analysis – there are all-in-one platforms, but they require subscribing to a service for win-loss analysis. It’s cheaper and faster to take a best-of-breed approach to win-loss software. The best-of-breed approach also provides flexibility to switch tools as new technologies like AI emerge, ensuring your process remains at the cutting edge. See our post here for more on choosing win-loss analysis software.

What kinds of questions should you ask during win/loss interviews?

To maintain some consistency, always have a discussion guide – always have a discussion guide that lists the 10-20 questions or topics you want to cover. This ensures a level of consistency across all interviews—but you also want to leave room for interviewers to prod into the most interesting or revelatory topics. Your exact questions should align with your goal. Listen to what the interviewee is saying and decide strategically where to dig in.

Sample topics for understanding no decisions:

Who originally suggested prioritizing this problem and investment? Why?
Who else was involved (e.g., buying team) in championing the investment?
Who was most influential in the funding decision? What was her perspective?
What was the business case for the funding decision?
How does this unfunded investment compare with one that was successfully made recently?

Sample topics to understand and improve opportunity win rate with late-stage deals:

What factors were most important in deciding to eliminate vendor A from consideration?
Why is factor A important to you?
Which vendor would you rank best for factor A? Worst? Why?
Were there any points in the buying experience where it was difficult to move forward with us?
What did [finalist’s] team do better than us?
What did we do better than [finalist’s] team?

Don’t shy away from asking seemingly “stupid” questions – these can often lead to powerful insights. For example, asking why a SaaS solution is important to a buyer can provide valuable information for positioning against competitors.

Peel the onion on topics that are of importance – don’t settle for a cursory understanding. Ask specific questions to understand the details. For instance, if you hear that your UX is better, ask who on their buying team assessed it better and why.

Be mindful of how you handle negative feedback about a rep or AE – always give a heads-up to the person involved and be careful about how this feedback is shared within the organization.

What are the most important things to get right?

Establish clear goals and cohorts – it could be a focus on mid-market versus enterprise or product A versus product B. Your goal will guide your funding and your cohort will ensure you’re gathering data from the right sources.

Don’t be afraid to ask questions and go off script – active listening is key here. While you should have a discussion guide, don’t let it lull you into a monotonous pattern. Ask “why” and “how” often, but be strategic about it. You’re typically working with a limited time frame, so you want to cover all the topics you set out to without going overboard.

Run the program continuously – technology markets are constantly changing, with new competitors and capabilities emerging all the time. Your pricing, positioning, and buyer decisions are all in flux. Therefore, it’s important to run your win-loss analysis program continuously. Start with a pilot of 5-10 interviews and then set the stage for making this a continuous program.

Leverage surveys for data collection – surveys are an efficient way to collect data on an ongoing basis. They allow you to gather information continuously rather than in one-off instances. This is particularly beneficial in fast-paced markets where conditions can change rapidly.

Recognize the changing nature of buyer decisions – as markets evolve, so do buyer decisions. Keeping up with these changes and understanding how they impact your business is key to a successful win-loss analysis.

What are common pitfalls?

Over-reliance on software for outreach – while automation can be a great tool for many business processes, it’s not always the best approach for outreach. There’s a common misconception that software can handle all aspects of outreach, but this isn’t realistic. Outreach requires a more personal touch and hard work. Simply sending out a single automated email and expecting results can lead to lower participation rates and longer completion times.

Lack of preparation and engagement – use the opportunity notes in your CRM, your buyer’s LinkedIn profile, and company website to prepare for an interview. It is crucial to spend time understanding your buyer’s context to have an informed and substantial conversation.

Having static discussion guides – the discussion guide should not be static. It should evolve as you learn more about your buyers, their needs, their market, and your competitors. As you go through interviews, you’ll become more fluent in the client’s language and develop new theories about what’s driving their wins or losses. This should lead to updates in the questions you’re asking to clarify these theories.

For further reading and helpful templates on building a win/loss analysis program, see here.