Beyond the Win (or Loss): How Contractors Can Use Debriefs and Lessons Learned to Improve Future Proposals

BLUF:

Every year I re-read Extreme Ownership by Jocko Willink and Leif Babin, a book that should be required reading for bid and proposal teams. They emphasize that leaders must take full responsibility for their team's performance and continuously seek ways to improve. The book, based on the authors' experiences as Navy SEALs, teaches that every challenge, whether success or failure, is an opportunity for growth. A key lesson is the importance of debriefing after every mission, operation, or task, just as elite military teams do, to identify what worked, what didn’t, and how to improve. By applying this mindset, leaders create a culture of accountability, adaptability, and relentless improvement, ensuring the team gets stronger with every experience.

Continuous Improvement: Winning a contract is great, but learning from the experience is critical. Practice extreme ownership, don’t make excuses. Leaders need to own mistakes and seek to improve on every new opportunity. Post-award debriefings and internal lessons learned are invaluable tools for Government contractors to improve their future proposals.

Debriefs Matter: Teams should always request a debrief (whether they win or lose) and how to use the feedback effectively. Understanding what the evaluators saw as strengths and weaknesses can directly inform your next capture and proposal efforts.

After Action Reviews (AARs): I’ll discuss conducting internal lessons learned sessions and implementing improvements. The end goal is to develop a knowledge management system and create a feedback loop where each proposal makes the next one better, boosting your pWin over time.

1. Always Ask for a Debrief – Win or Lose

During my time in the U.S. Army, we would conduct an After Action Review (AAR) to evaluate performance, identify what we would sustain, and what we could improve. This structured approach ensured we constantly iterated on Tactics, Techniques, and Procedures (TTPs), while refining strategies to enhance future outcomes. Similarly, in federal contracting, post-award debriefings serve as a critical initial AAR for your business development efforts. Just as military units analyze engagements to sharpen operational effectiveness, bid and proposal teams should leverage debriefings to gain insights into evaluation criteria, strengthen proposal strategies, and refine competitive positioning. By treating debriefings as mandatory learning opportunities—regardless of the outcome—we create a cycle of continuous improvement, maximizing our ability to secure future contracts.

After an award decision, the Government provides an opportunity for a debriefing. In the debrief, the source selection team shares valuable feedback on your proposed solution. Depending on the type of source selection contents of debriefings can vary, but in the case of acquisitions using INFORM 2.0 procedures, the Government shares the entirety of the findings of the Technical Evaluation Board/Source Selection Evaluation Board; including observations, strengths, weaknesses, significant weaknesses, and deficiencies. Many contractors only ask for debriefs when they lose, but it’s equally important to request one when you win. Why? Because understanding why you won is just as (if not more) valuable as knowing why you lost.

Best practice: Request the debrief promptly. There’s usually a limited window (often within 3 days of award notice for federal contracts) to request a debrief. Submit a polite written request to the contracting officer as soon as you learn of the award decision.

Best practice: Go in prepared to listen and learn. Approach the debrief with an open mind, not defensiveness. The goal is to gain insights, not to argue the outcome. Take detailed notes on every point the government makes about your proposal.

2. Extracting Key Insights from Debrief Feedback

During the debrief, you’ll likely receive information on how your proposal was evaluated in each area. This feedback is a goldmine for identifying exactly where to improve. For example, you might learn that your technical approach was strong (a strength), but your staffing plan was confusing and didn’t match your technical approach, or that your proposal quality was seen as low. It’s crucial to capture and record these lessons systematically.

This is where documenting your lessons learned is crucial. Seek to document these in a standard format to make building a knowledge management system easier. This is an ideal place to engage your data analysts, subject matter experts, and build a repository of these lessons learned. This is a prime opportunity for organizations to utilize AI to ensure that the mistakes of the past are not repeated on future efforts.

Best practice: Ask clarifying questions. If something is unclear in the feedback, it’s okay to ask for clarification during the debrief. Be respectful, but make sure you truly understand what the Government did or did not understand with your approach.

Best practice: Focus on actionable takeaways. After the debrief, list out the specific strengths and weaknesses noted. For each one, consider what action you can take next time. A weakness like “insufficient risk mitigation” means you should beef up that section in future proposals. A strength like “excellent past performance examples” indicates you should continue that approach in your next bids.

Best practice: Collect feedback over time. Keep a log of feedback from every debrief. Over multiple proposals, you may see patterns – for example, if several debriefs mention that “the proposal was difficult to navigate,” that suggests a need to improve layout or formatting consistently.

Best practice: Institutionalize knowledge. Maintain a repository of lessons learned and debrief findings that all proposal teams can access. Over the years, new team members can review this knowledge base to avoid past mistakes. Make continuous improvement part of your Standard Operating Procedures (SOPs) for business development and proposals.

3. Conducting Internal Lessons Learned Sessions

“It’s not what you preach, it’s what you tolerate.” - Jocko Willink

Beyond the formal Government debrief, your team should do an hotwash after each proposal effort. Gather your capture team, proposal writers, subject matter experts, and anyone else involved. The aim is to evaluate your own process: what worked well and what didn’t in pursuing and writing the proposal. This introspective look can reveal process weaknesses (like last-minute rushes or communication breakdowns) that might not be obvious in the final proposal document but still affect your success.

Best practice: Hold the session soon after submission. While the experience is fresh, bring the team together to discuss. Encourage honest feedback in a blame-free environment. For example, was the bid/no-bid decision made at the right time? Did writers have the information they needed when they needed it? Document these observations.

Best practice: Cover all phases. Structure the discussion to cover business development/capture activities, the proposal planning, writing, review, and production phases. Maybe the team finds that early capture was great, but the discriminators identified by the team didn’t get translated in the proposal. Identifying these internal issues is key to fixing them.

Best practice: Invite candid input. Team members may be hesitant to point out problems. Consider having a neutral facilitator gather input on perceived shortcomings of the team, and have the tough conversations. The more openly you discuss weaknesses in your process, the better you can address them.

4. Implementing Improvements and Next Steps

Identifying lessons is only half the battle – you need to implement changes so that future proposals benefit. Take the insights from the debrief and your internal review and turn them into concrete actions. This might mean updating your proposal templates, investing in staff training, or adjusting your capture process timeline. The next time you pursue an opportunity, these improvements should give you a better chance of success.

Best practice: Update templates and checklists. If debriefs revealed a recurring issue with, say, proposal formatting or a missing section, update your standard template to fix that. Add new items to your compliance matrix or review checklists based on what you’ve learned that evaluators care about.

Best practice: Train your team. Use lessons learned as training material. If a weakness was identified in how you wrote your management approach, consider a workshop on improving that section. Share debrief feedback and internal lessons with the broader team (not just those on the last proposal) so everyone learns.

Best practice: Refine strategic capture approach. If internal discussion revealed that you didn’t know the client well enough, then enhance your capture efforts next time. Did you properly leverage client engagements, ask the right probing questions at due diligence sessions, and truly understand the objectives that the customer was trying to achieve? Ensure that for the next opportunity, you’re better positioned and not repeating the same mistakes that led to a loss.

5. Fostering a Culture of Continuous Improvement

Over the long term, the goal is to build a culture where every proposal, win or lose, is an opportunity to get better. Leadership should encourage teams to pursue excellence by learning from mistakes and owning them, rather than assigning blame. A company that consistently applies lessons learned will refine its proposal development process, leading to higher-quality bids and a higher win rate.

Best practice: Celebrate the wins and the lessons. When you win, congratulate the team, but also review why you won. When you lose, avoid a punitive tone; instead, treat it as a learning investment. Recognize team members who bring forward constructive suggestions for improvements.

Best practice: Track metrics over time. You might monitor your proposal win rate or the number of weaknesses noted in debriefs, and see if those metrics improve after implementing changes. Seeing progress can motivate the team to keep refining their approach.

Conclusion

In Government contracting, each proposal is a learning experience. By actively seeking debrief feedback and reflecting on your internal process, you turn every outcome into a stepping stone for future success. Bid and Proposal teams need to embrace the idea of continuous improvement and strive to get better each time, win or lose. Through this relentless pursuit of better outcomes, attention to detail, and leveraging past losses to develop better TTPs and SOPs; teams will develop stronger bonds and sharpen their edge. The contractors who win consistently are often those who never stop improving their methods. Leveraging debriefs and lessons learned ensures that even a loss today can contribute to a win tomorrow.

FEDSIM Service Delivery Model (SDM) Part I: AAS Re-Organization

Introduction

As an Acquisition Project Manager, I encounter proposals from all walks of DoD contractors, with a significant focus on some of the most niche and crucial focus areas of the Department (e.g., AI/ML, IT Modernization, Command and Control, Communications, Computers, Cybersecurity, Intelligence, Surveillance, and Reconnaissance (C5ISR), and Joint All-Domain Command and Control (JADC2)). While I don't prepare proposals, some best practices have emerged over the years that I hope to capture in a few short articles here.

Recently, the Federal Acquisition Service (FAS) conducted a re-organization of the Assisted Acquisition Service (AAS) to bring the eleven Regional Contracting Offices and the Federal Systems Integration and Management Center (FEDSIM) under one umbrella organization, referred to as APEXs (AAS Client-Based Acquisition & Procurement Centers of Excellence). My focus will be on APEX 5, AAS Defense, as this is the legacy FEDSIM program's origins and currently the center of gravity for the FEDSIM SDM.

If you've made it this FAR (get it) I'm sure that you're at least familiar with the legacy FEDSIM's well defined processes. The good news is that the model still works, and the new FEDSIM SDM is extremely similar. While the FEDSIM SDM is not ideally suited for all requirements that come through AAS, it is a logical approach for large, multi-tenant, complex acquisitions that we often encounter. The projects that work for the FEDSIM SDM generally fit and operate within these parameters:

• Greater than $250 Million (M), often times greater than $1 Billion (B).

• Within scope of one of the premier GSA Government Wide Acquisition Contracts (GWAC), including ASTRO, ALLIANT 2, and OASIS. When appropriate, TOs are set aside for on a vehicle that supports them (e.g., VETS II).

• Non-commercial - suited for a Cost Type structure such as Cost Plus Fixed-Fee (CPFF) and Cost Plus Award-Fee (CPAF).

• Utilize extensive market research and industry engagement avenues such as Request for Information (RFI), Market Analysis Discussions (MAD), draft Task Order Requests (TOR), Industry Day, and Due Diligence sessions.

• Evaluated via Technical Evaluation Board (TEB) for written technical proposals elements (e.g., transition-in plan and project staffing plan), oral/video presentations given by the offeror, and a comprehensive cost analysis. These evaluations generally occur over the course of 2 or 3 days and involve both AAS personnel and client personnel, chosen to provide the most technically focused team available for the given requirement.

• Corporate Experience, similar to Past Performance, is evaluated as Relevant or Not Relevant.

As you can imagine, there is a significant effect on the stakeholders of AAS when change occurs within the organization. Hopefully I can provide some insight for our community to better understand what those implications might be.

So, why the re-org if the process essentially remains the same?

From my standpoint, the AAS re-org will result in more efficient operations and a more focused customer service. With a successful re-org some key changes could result, such as:

1. Centralized Reporting: With AAS moving to a single team structure, replacing multiple regional offices, centralized reporting becomes less onerous. The data and resulting analytics can easily be applied across the more vertically aligned organization.

2. Mission-Focused Teams: New teams are assigned to specific customer segments and not based on arbitrary assignments, leading to better alignment for individual projects. The APEXs will be ideally suited to make decisions and align processes to their own projects. Projects can either align to the INNOVATE/FLEX SDMs (a subject for another article) or to the FEDSIM SDM. Having the ability to align to these models will make for a more agile approach to solving the unique, and often complex, issues that face AAS projects.

3. Enhanced Knowledge Management: As legacy FEDSIM segments (e.g., Air Force) are aligned with the APEXs, they will take with them the best practices and standardization that has long been the standard among FEDSIM templates and processes. Through a constant iterative approach to the FEDSIM SDM, these lessons learned will be passed through the FEDSIM SDM and implemented throughout the organization.

4. Improved Employee Satisfaction: The re-org has already allocated employees more flexibility and mobility within AAS, as the new structure unlocks new roles and responsibilities shared among the APEXs.

Ultimately, consolidating the disparate regions into a more vertically aligned APEX structure could lead to breaking down the barriers to innovation, a broader adoption of the FEDSIM SDM, and process optimization throughout the organization. The increases in policy collaboration and the processes arising from the re-org, and the efficiency and effectiveness that results, will usher in a new era of cooperation for AAS and FAS for years to come.

Benefit to Industry Partners

Of the many stakeholders in the FEDSIM SDM, our partners in industry are probably the ones asking what they have to gain by the consolidation effort undertaken over the last few years. Well, viewing it from the lens of the contractors that generally interact with AAS, and previously interacted with legacy FEDSIM, I can see some potential benefits.

While the "standard FEDSIM process" has historically resulted in faster times to award, incorporating the APEX model and expanding the use of the FEDSIM SDM (as well as the use of the FLEX SDM), will benefit all procurements through AAS with a more standardized approach. Our industry partners can now expect a similar approach from each of the APEXs, resulting in a flattened learning curve and lowered barrier to entry for these projects. This adjustment to our business practices will provide more predictability for our offerors who chose to engage with our procurements. I anticipate the baseline question in the future will be "Is this a FLEX or FEDSIM SDM procurement?" The answer to that question will inform many unknowns for the potential offerors.

Another consequence to industry is the opportunity to reduce a footprint from a BD perspective. Since requirements will be more aligned to mission needs through the APEX structure, the less complex and lower dollar value acquisitions can be tracked alongside the FEDSIM SDM acquisitions for a more "common operating picture" of our customers' acquisition ecosystem. This could provide for more focused BD, with a common link in the APEX leadership and logical linkage between these requirements.

In addition to the common operating picture, the knowledge sharing that will inevitably occur as these offices converge in the APEX structure will contribute to what I most often hear in my exchanges with industry, a lack of standardized requirements. One of the benefits of the FEDSIM SDM (and eventually the FLEX SDM) is a shared "templated" approach to preparing the PWS or SOO, deliverables, and a standardized approach to PMO operations. This "templated" approach extends to key personnel, security, invoicing, and the communication of other administrative details throughout the TOR.

Finally, and perhaps most crucially, the impact to our instructions to offerors (aka Section L) and evaluation factors for award (aka Section M) will be viewed through the same lens throughout AAS and not just narrowly tailored to the projects that currently fall within AAS Defense. Some variables in the process include when to use oral or video presentations, page count limitations, the use of scenarios, and a few others. As the organization as a whole begins to iterate on approaches to evaluation, we can expect some uncertainty. However, in short order industry can reasonably assume that the APEXs will develop approaches that are interchangeable depending on the nature of the acquisitions.

Conclusion

I hope that this article helped to tame some uncertainty on the future of FEDSIM, the FEDSIM SDM, and the future now that you know the state of AAS as we stand today in the re-org to the APEX structure. We can expect some challenges as the APEXs are aligned over the coming months or years, but out of this my hope is that we reduce the burden on our stakeholders and industry partners, can simplify the approach we take to solving complex procurement challenges, and are more closely aligned to our customers' needs.