Business Bridge Supplier Toolkit

How and Why to Conduct a Win-Loss Review

Researched and written for Business Bridge by Strategic Insights Inc. | Thursday, March 14, 2024

As a small business owner with limited resources, winning new deals and growing revenue streams can feel like an uphill battle. You pour sweat and tears into winning new clients and expanding existing accounts, yet some deals inevitably slip away no matter how hard you try. It leaves you wondering:

  • Why do some prospects say yes while others say no?

  • What crucial factors tip the scales for or against us?

  • How might we improve our strategy and offerings?

This is where win-loss reviews come in. By dissecting through direct or indirect conversations deals won and lost, or reviewing the offerings and pitch of the company that was awarded the contract, you gain insider insights into the exact reasons supplier decisions get made.

Why are win-loss reviews mission critical to winning contracts?

Win-loss reviews offer a range of benefits that directly translate into sales, revenue and market share growth for small to medium-sized businesses (SMBs). They help you:

  1. Identify successful sales tactics to enable best practices.

  2. Understand decision drivers to refine messaging and positioning.

  3. Improve prospect targeting and qualification criteria.

  4. Uncover product gaps causing lost deals.

  5. Validate product-market fit to fuel innovation.

  6. Pinpoint competitor strengths and weaknesses.

  7. Tailor differentiation strategy and value proposition.

  8. Adjust pricing, promotions and packaging.

  9. Diagnose and resolve process inefficiencies.

  10. Increase deal conversion rates.

For resource-constrained SMBs, win-loss reviews are akin to having a black-box flight recorder that reveals insights behind corporate decision-making.

How to create an impactful win-loss review process

While win-loss reviews are extremely beneficial, they need to be executed methodically to yield useful results. To get the most impact from the win-loss review process, it’s critical to create a comprehensive win-loss review process. What follows are the six steps to help set up an effective win-loss review process:

1. Establish explicit review goals

Be clear about what specific information you want to gather and key questions you want answered. Some examples to consider:

  • Why do we win or lose against this specific competitor?

  • What product capabilities drive wins?

  • What messaging resonates with C-level execs?

2. Gather data from multiple sources

Win-loss reviews should incorporate feedback from:

  • Client representatives

  • Buyers

  • Business unit representatives

  • Prime contractors, if they were part of the proposal-reviewing team

  • Prospects

  • Your own sales team

Select a mix of current clients and lost prospects that represents your ideal future customers. Ensure a 50/50 split between won and lost opportunities to get a balanced view. While it can be difficult to obtain feedback from lost prospects, it can help if you present your request for feedback as an important learning tool for your company.

3. Define participation criteria

Choose participants carefully to enable open sharing without biases. Select impartial interviewers, such as third-party product marketing or market research specialists. Involve evaluators, decision-makers and influencers as interviewees.

4. Create an interview guide for consistent execution

A structured interview guide ensures consistent data collection across all reviews. Tailor questions to your goals and frame them neutrally to avoid leading responses.

Some example questions:

  • How would you describe our product or service value proposition?

  • Which factors most influenced your purchase decision?

  • What competitive offerings did you consider?

5. Synthesize learnings and identify action items

Compile feedback from all sources and look for overarching themes related to:

  • Winning attributes and strategies

  • Shortcomings related to competitors

  • Market trends and shifts

Share key takeaways across sales, marketing, product and technology teams and prioritize follow-up initiatives to create a cohesive win-loss roadmap.

Your win-loss analysis will get better over time as you gather more data. Revisit goals periodically and track metrics to correlate review findings with sales outcomes. Maintain a frequent cadence to accelerate improvement and Return on Investment (ROI).

6. Tie the learnings from win-loss reviews to your business development process

An impactful win-loss review framework with long-term benefits for your business includes the following five components:

  1. Explicit goals tied to key business initiatives

  2. Qualitative and quantitative data from multiple sources

  3. Structured analysis to identify priority action areas

  4. Cross-functional engagement across your team to drive change

  5. Continuous tracking to measure impact over time

Getting started is the biggest hurdle

For SMBs that haven’t yet instituted win-loss reviews, taking baby steps is key before scaling the program. Begin with a sample of five to 10 recently closed deals before expanding to a wider set. Uncover one to two actionable improvement areas from the initial set before broadening the scope. Prevent biases by using third-party interviewers and structured questions. Talk to your contacts at your corporate clients if you need more direction.


Over time, win-loss reviews reinforce a culture of continually seeking client feedback, understanding decision drivers and taking corrective action. This ultimately creates a self-improving company focused on meeting client needs and accelerating revenue. Though win-loss programs require cross-functional coordination, their payoff makes it well worth the effort for high-growth SMBs.

Further Reading:

  1. “Win/Loss Analysis: An Introduction to Win/Loss Analytics.” hypcccycl, 25 Jan. 2022,

  2. Bond, Conor. “The Definitive Guide to Win/Loss Analysis: How to Gather, Analyze, and Act On Win/Loss Data.” Crayon Inc, 7 May 2021,

  3. Kane, Nick. “How to Conduct a Win-Loss Analysis.” Quirk’s Media, 22 Dec. 2023,

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