How to Conduct a Proposal Lessons Learned Session

Jun 27, 2024

How to Conduct a Proposal Lessons Learned Session

It is far too common, once the dust settles after submitting a proposal, for a Proposal Team, including subject matter experts (SMEs), account managers, and senior management, to move on to the next project without taking a moment to reflect.

Proposal Teams often get caught up in developing the proposal that they fail to capture issues and lessons learned along the way making it difficult to remember what the issues were, why they happened, and how they were resolved. However, the practice of capturing lessons learned can be a game-changer for your organization. Hold a lessons learned session within one week after submission to leverage your team's collective wisdom and improve future proposals.

The Purpose of Lessons Learned 

Think of a lessons learned session as a collaborative post-mortem on your proposal process. It's a space where your team comes together to discuss candidly what went right and what didn't. It's an opportunity to collect insights from every member involved in the proposal, ensuring that every voice is heard. 

The Preparation Phase 

Thorough preparation is crucial to conducting a lessons learned session successfully. Start by identifying all who were part of the proposal process. Be careful not to limit yourself to the obvious key players, such as the SMEs, tech, management, transition, resume writers, and volume leads. Don’t forget others involved, such as pricing specialists, solution architects, account managers, graphic artists, editors, color reviewers, and senior management. Also worth considering are any teaming partners who provided significant input. 

Use a survey tool to gather meaningful data from each team member to identify areas for improvement. The Proposal Manager should review these comments and prepare an After-Action Report as a comprehensive guide for your session. Make sure to prepare a list of thought provoking questions to guide the discussion. The Proposal Manager should regularly capture lessons learned during the proposal process, such as after each color review, to make the post-proposal review better. 

Set a clear agenda, choose a convenient date and time, and consider ways to involve those unable to attend. Consider adding the lessons learned meeting to the proposal calendar early to integrate it into the process.

Lessons Learned Quote

The Facilitator's Role and Session Introduction 

Designate a facilitator for the session; this person will steer the conversation and ensure everyone actively participates. The facilitator's role is to create an environment where open and honest dialogue can flourish. At the beginning of the session, extend a warm welcome to all participants. Explain that the purpose of the gathering is not to assign blame but to foster continuous improvement. Be sure to set some ground rules to ensure a respectful and open exchange of ideas. 

Delving into the Proposal 

Start by providing a brief overview of the submitted proposal, reminding everyone of the proposal's main objectives and intended outcomes. Then, following the agenda, discuss the proposal process itself in detail. Explore each stage, from the initial strategy and planning to the final submittal and sign-off. Encourage team members to share their experiences, both the highs and lows, at each step. Below is a sample checklist from the KSI Advantage™ Capture & Proposal Guide that is useful for the lessons learned review.

Lessons Learned Checklist_KSI Advantage Tool-1

Work to identify bottlenecks or inefficiencies that cropped up along the way. Here are some essential aspects to achieving a successful lessons learned session: 

1. Recognizing Strengths and Weaknesses 

Ask your team to reflect on the strengths of the proposal process. What worked exceptionally well? What were the positive outcomes, successful strategies, and moments of effective collaboration? Conversely, encourage participants to openly discuss the weaknesses and shortcomings they encountered. Delve into areas where the team faced difficulties, encountered obstacles, or even made mistakes. 

2. Getting to the Root of the Issues 

Now, it's time to delve deeper into the identified weaknesses. Try to uncover the underlying reasons behind them. Were there process gaps that needed addressing, resource constraints that hindered progress, or communication issues that caused misunderstandings? 

3. Extracting lessons learned 

Facilitate a discussion on the lessons learned from both strengths and weaknesses. Make sure to encourage participants to share their key takeaways. What can these experiences teach your team for future proposal efforts?   

4. Documentation and Action Items for Improvement 

Compile a comprehensive lessons learned document capturing all insights, recommendations, and action items. Collaboratively define actionable steps to enhance the proposal process. Assign responsibilities for implementing these action items to specific persons or organizations with timelines for implementation to ensure that lessons learned are incorporated into future proposal efforts. Summarize the key insights and action items that emerged from the session. Make sure this document is easily accessible to relevant stakeholders for future reference.  

Feedback and Looking Ahead 

The essence of a lessons learned session is to draw out relevant, useful feedback. Allow participants to provide feedback on the lessons learned session itself. Emphasize the value of continuous improvement and the pivotal role of lessons learned in enhancing future proposal efforts. Finally, express gratitude to all participants for their contributions and dedication to making your organization's proposal process even better. 

In the end, a lessons learned session isn't just about looking back; it's about looking forward to a brighter, more efficient future. It's a journey toward fostering a culture of learning, promoting transparency, and driving improvements in your proposal process. And don't forget to celebrate this collective commitment to growth and progress within your organization. 

graphic of a checklist

Melissa Serna

Written by Melissa Serna

Melissa Serna is a Proposal Development Consultant with Key Solutions. She is an alumnus of Florida International University where she earned a BS in Mass Communication with a concentration in Journalism. Melissa then went on to complete an MS in Higher Education Administration at the University of Miami. She has extensive writing and editing experience and in her free time enjoys yoga, cooking, and traveling.

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