By Ashley (Kayes) Floro, CPP APMP
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March 30, 2026
When was the last time your team truly examined why you won—or lost—a proposal? Every submission your team makes, win or lose, contains a roadmap for doing better next time. Yet many organizations treat each proposal as a standalone event, moving quickly from one bid to the next without pausing to reflect on what worked, what didn't, and why. This is a costly mistake. A structured lessons learned program, built into every stage of the business development lifecycle, is one of the most powerful tools a company can use to sharpen its competitive edge. What many organizations overlook is that some of the most valuable lessons come directly from the customer. Internal assessments are important, but they only tell part of the story. Customer debriefs provide a rare opportunity to understand how the Government evaluated your solution, what aspects of your proposal resonated, where evaluators perceived risk, and how your approach compared to the competition. When combined with internal lessons learned efforts, debriefs can uncover strategic insights that dramatically improve future capture and proposal performance. Conducting Lessons Learned Conducting lessons learned after each proposal submission is a critical part of the business development lifecycle. It helps companies understand where they are excelling and where they need to improve. To ensure the experience is fresh in everyone's mind, each member of the proposal team should document their impressions—both positive and negative—within the first week after submission. Sample questions to consider include: Was the proposal development schedule reasonable and realistic? Why or why not? Were there any bottlenecks or major issues? If so, what were they, and how could they be mitigated in the future? Did the team work well together? If not, how could team dynamics have been improved? How effective was communication among the team? What went well? What could have been improved? Did any unexpected problems occur during proposal development? If so, how could they be mitigated going forward? Did the team stay within its B&P budget? If not, what could have been done differently? What worked best during the capture and proposal effort? What areas require improvement? A practical way to gather and analyze this feedback is to send a survey to each team member using an automated tool, which makes it easier to collate and compare responses. Just as importantly, organizations should ensure lessons learned discussions extend beyond proposal operations and include capture, pricing, solutioning, staffing, and customer engagement activities. Many proposal losses are rooted in issues that occurred long before writing ever began. Request a Customer Debrief Too often, companies only request debriefs after a loss, missing valuable opportunities to learn from wins as well. Winning debriefs can reveal why the customer selected your solution, which strengths carried the most weight, and where evaluators still saw weaknesses or risk despite awarding your team the contract. Those insights can be invaluable for recompetes and future pursuits. When requesting a debrief from the Government, professionalism matters. Requests should be submitted promptly, kept concise, and focused on understanding the evaluation rather than challenging it. The objective is not to argue with the customer, but to gain insight into how the proposal was perceived and evaluated. During the debrief itself, the most productive teams ask thoughtful, strategic questions such as: What proposal strengths had the greatest impact on the evaluation? Were there areas where the Government perceived increased risk? How well did the proposed approach align with the agency’s priorities? What differentiated the winning proposal? Were there areas where the proposal appeared compliant but not sufficiently tailored? Did the Government identify any gaps in customer understanding? The best debriefs often reveal issues that are not immediately obvious in evaluation scores alone. A technically compliant proposal may still fail because it lacked clear differentiation, did not sufficiently address customer pain points, or failed to inspire confidence in execution. Those insights are essential for improving future capture and proposal strategies. Equally important, organizations should approach debriefs as relationship-building opportunities. Agencies remember contractors that engage professionally, ask intelligent questions, and demonstrate a genuine commitment to improvement. After Action Report Once the feedback has been gathered, the Proposal Manager should review the trends and prepare an After Action Report that details lessons learned, root causes, and recommended next steps. This report should be shared with the full proposal team to ensure that insights are carried forward into future efforts. The most effective After Action Reports do more than document tactical issues. They identify whether the team’s overall strategy aligned with the customer’s priorities. Did the proposed discriminators truly differentiate the solution? Did the proposal clearly communicate customer understanding? Were there areas where the team assumed the customer valued something that ultimately had little impact on the evaluation? Answering these questions helps organizations move beyond surface-level process improvements and make meaningful strategic adjustments. Lessons Learned Session Additionally, after contract award is announced, the team should conduct a formal Lessons Learned Session to document and discuss observations, findings, and conclusions—win or lose. This session should incorporate both internal feedback and customer debrief information whenever possible. By understanding where the team encountered roadblocks, where the customer found gaps in the response, and what elements of the solution resonated most strongly, organizations can strengthen both their processes and their competitive positioning. Equally important: identify what the team is doing well and make sure those practices are preserved and repeated. Analyzing Trends and Updating Standard Operating Procedures (SOPs) Conducting lessons learned after each proposal is valuable, but the benefit compounds when you step back and look at the bigger picture. On an annual basis, review your After Action Reports, customer debrief notes, and lessons learned sessions as a body of work, and analyze them for recurring themes and patterns. As the year wraps up, whether you follow a corporate fiscal year or the calendar year, ask your team: What challenges keep surfacing? Where does the team consistently perform well? What issues repeatedly appear in customer debriefs? Are evaluators consistently identifying the same weaknesses or risks? Are there gaps in capture execution, customer engagement, staffing, or pricing strategy? Discussing and sharing these trends with your team creates a culture of transparency and accountability, and helps focus improvement efforts where they matter most. More importantly, translate those findings into action by updating your business development and proposal SOPs. If internal feedback shows the team is consistently scrambling during production, adjust your SOPs to launch the production process earlier. If customer debriefs repeatedly cite a lack of customer understanding, take a hard look at your capture process and strengthen your call plan execution. If evaluators consistently identify transition risk or staffing concerns, revisit your solution development and recruiting strategies. Continuously refining your processes in response to real data, especially direct customer feedback, is one of the clearest paths to improved performance and more wins. Final Thoughts Every organization in this industry wants to win more, and win rates are often cited as the headline measure of a business development organization's health. While they are a useful starting point, win rates alone don't tell the whole story. Too many variables influence any single outcome. What matters more is building the discipline to learn from every effort, regardless of the result. A consistent lessons learned program, paired with customer debrief analysis, annual trend reviews, and a willingness to update your processes, creates a feedback loop that makes your team sharper over time. The companies that win consistently aren't just the ones with the best writers or the biggest budgets, they're the ones that systematically learn faster than their competitors. Every proposal, whether it results in a win or a loss, provides an opportunity to improve. The organizations that capitalize on those opportunities are the ones that steadily build stronger capture strategies, stronger proposals, and ultimately, stronger win rates over time.