Kick Off with Confidence: A Guide for Proposal Leaders

Ashley (Kayes) Floro, CPP APMP • February 19, 2026

In the intense world of proposal development, the kickoff meeting sets the tone for everything that follows. It's a strategic opportunity to align the team, clarify goals, and establish early momentum. Kickoff meetings enable you to:

Build shared understanding of the proposal scope, schedule, and objectives
Clarify roles and responsibilities for all team members
Define communication protocols and decision-making processes
Surface early questions or risks
Energize the team with a clear sense of direction and urgency

When executed effectively, a kickoff meeting helps prevent missteps, minimizes rework, and provides the foundation for a cohesive, collaborative proposal effort.

Plan Before You Launch

A successful proposal effort starts well before the kickoff meeting. Thoughtful planning and preparation lay the groundwork for efficient execution, effective collaboration, and a high-quality, compliant submission. Before the team gathers to launch the proposal, the proposal manager should ensure that foundational tools, materials, and logistics are in place. This includes developing a comprehensive proposal management plan, setting up a centralized collaboration workspace, preparing writing templates, and crafting a structured kickoff meeting agenda and presentation. These upfront investments not only help align the team from day one, but also reduce confusion, minimize rework, and accelerate content development. With the right planning in place, your proposal team can start strong and maintain momentum through submission.

Proposal Management Plan

One of the most important planning tools is the proposal management plan. Before the kickoff meeting, the proposal manager must take time to develop a clear and complete proposal management plan. The proposal management plan should include:

A proposal schedule with all key solicitation milestones (questions due dates, intent to bid due dates, site visit dates, proposal due date) and internal deadlines (internal questions deadlines, pens down dates, color team review dates, etc.)
Vacation/time off schedule or tracker
Outline and compliance matrix
Roles and responsibilities matrix
Contact list
Action items tracker
Proposal style guide and wall of truth
Proposal templates
Relevant past proposals and boilerplate content

The proposal manager should walk through the proposal management plan details during the kickoff meeting. This will ensure everyone is aligned on the objectives, expectations, and processes. Consider recording the meeting for those who cannot attend; then post the proposal management plan in a shared collaboration space.

Set Up a Collaboration Workspace

So that the team can hit the ground running following the kickoff meeting, it is critical to set up a collaboration workspace before the proposal kickoff meeting. If you don’t already have a workspace that was established during the capture phase, you’ll need to set up a workspace where you can share solicitation files, answers to questions, section drafts, win themes/other capture materials, the proposal management plan, graphics, source materials, and other proposal content. You’ll want to choose a tool that with access control and document version control capabilities, such as SharePoint.

Have Proposal Templates Ready

It’s also helpful to have the proposal writing templates ready before the kickoff meeting. If the team hasn’t already conducted storyboarding exercises, you’ll want templates ready for those as well. When templates are prepared in advance, writers can start drafting immediately after the kickoff. This reduces downtime and helps maintain momentum, especially on tight proposal schedules where every day counts. Templates also define the structure, tone, and formatting of the response. This helps section leads and contributors understand what’s expected of them and reduces the likelihood of inconsistent or non-compliant content. Well-designed templates are built to match the solicitation’s requirements, including section headings, numbering, page limits, and formatting rules. This keeps the team aligned with compliance from the start and reduces rework later.

Prepare a Thoughtful Kickoff Deck

The kickoff meeting will set the tone for the remainder of the proposal, so it’s imperative to come to the meeting organized, prepared, and positive. The proposal kickoff deck should outline to the team why the proposal and future contract matter. Outline the customer’s mission, key drivers, and what a winning outcome looks like. This helps the team stay customer-focused and mission-aligned from day one. Other key components of the kickoff deck and agenda include:

Team Overview. If applicable, introduce the team members and what value they bring to the team. Briefly highlight their relevant experience or expertise to reinforce confidence in the team’s ability to deliver. This not only builds credibility but also helps the team understand who to go to for specific needs or questions. For cross-functional or newly formed teams, this step is especially important in fostering collaboration and trust from the outset.

Opportunity Overview. Provide additional details about the opportunity, any relevant capture summaries, and a high-level picture of the proposal requirements, including major sections and page limitations. It’s also helpful to walk through the key evaluation criteria and the relative weights of each major section.

Win Themes Review. Walk through the win themes—the high-level value statements that articulate why your team is the best choice for the customer. These themes should be tightly aligned to the customer’s mission, priorities, and evaluation criteria. Use this time to explain how each theme ties back to your solution’s strengths and emphasize that they should be consistently integrated throughout all sections of the proposal. Reinforcing win themes early ensures the entire team is messaging in a unified, strategic voice from the beginning.

Proposal Team Roles and Responsibilities. Review the proposal organization chart and clearly outline who is responsible for what. Walk through key roles such as the proposal manager, volume leads, writers, reviewers, and subject matter experts. This will ensure everyone understands their individual contributions and how they fit into the larger effort. Clarify expectations for task ownership, deadlines, and collaboration to prevent confusion and overlap. This step helps establish accountability, streamlines communication, and sets a strong foundation for coordinated execution throughout the proposal lifecycle.

Ground Rules for Collaboration. It’s also important to discuss how the team is expected to communicate, the tools they should use, and the schedule of standups or status checks. Establish expectations for responsiveness, escalation, and document sharing (e.g., SharePoint, Google Drive, proposal management tools).

Messaging tools like Slack and Microsoft Teams enable teams to ask quick questions. These tools also typically have video calling capabilities, which can act like “popping into someone’s office.” Texting, email, and phone calls can be great to use as well. Consider including preferred communication methods in your proposal contact list.

During the kickoff meeting, train your team on these tools. You should also set some norms and expectations, such as when to use email versus chat, expected response times, and expectations for enabling the video function (or not). You should also review the proposal workspace, how things are organized, and how to edit files while maintaining version control.

Proposal Schedule and Logistics. As part of the kickoff meeting, you should be sure to review the proposal schedule and highlight major milestones, including questions due dates, proposal review pens down, and site visits. You’ll also want to walk the team through general proposal logistics. Will there be a daily stand-up call? At what time? Who is expected to attend. What tools are being used for proposal collaboration and reviews? Is this an in-person effort, virtual, or hybrid? Especially if this is the first time you have worked with a particular team, it can also be helpful to walk through the general proposal process that you will follow—for example, what the team can expect from Pink Team, Red Team, Gold Team, and any other reviews.

Ask team members to raise potential red flags early—whether it’s gaps in information, tight timelines, or competing priorities. Capture risks in a shared tracker and assign owners to monitor them. Close the meeting with immediate actions: What’s due in the next 24–48 hours? When is the next meeting? Who’s responsible for what? Leaving the team with clear direction facilitates forward progress.

Kickoff Meeting Tips for Facilitators

Facilitating a successful kickoff meeting is more than just walking through an agenda, it’s about creating the right environment for collaboration, alignment, and momentum. Your approach sets the tone and shapes the team’s experience. By being intentional in how you show up and structure the conversation, you can foster a productive dynamic that carries through the rest of the proposal effort. Keep these best practices in mind as you prepare to lead the team from the very first meeting:

Start with energy: Your tone sets the vibe. Bring clarity, confidence, and positivity.
Balance structure with flexibility: Keep the meeting focused but leave room for discussion and input.
Encourage engagement: Ask questions, invite comments, and watch for non-verbal cues in virtual settings.
Document and distribute: Capture meeting notes, action items, and decisions—then share them promptly.

If your team is remote, consider turning cameras on to build connection.

Final Thoughts

The kickoff meeting is more than a starting point, it’s a strategic opportunity to align your team, establish shared goals, and create the conditions for a smooth, successful proposal effort. With thoughtful planning, clear communication, and the right tools in place, you can turn this first meeting into a launchpad for collaboration, accountability, and high-quality results. Remember, how you begin often determines how you finish. Invest the time and energy to make your kickoff count, and you’ll position your team to deliver a compelling, compliant, and competitive proposal.

Originally posted at Proposal Reflections.

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Proposal Planning Done Right: The Value of Storyboarding

By Ashley (Kayes) Floro, CPP APMP • February 25, 2026

In proposal development, the difference between a rushed response and a winning one often comes down to planning. One of the most effective planning tools is storyboarding—the process of transforming strategy and requirements into a clear, organized roadmap for writers. Storyboarding bridges the gap between big-picture strategy and detailed content. Instead of diving straight into writing, it forces teams to pause and address critical questions up front: What win themes should we emphasize? How do we differentiate ourselves from competitors? What proof points and evidence will make our claims credible? By answering these questions early, proposal teams ensure the final product reflects a deliberate strategy rather than a patchwork of boilerplate. This step is especially important in complex proposals where multiple authors contribute. Without storyboards, sections can easily become repetitive, inconsistent, or off message. With storyboards, however, teams gain a shared outline, unified messaging, and a structured plan that keeps writing focused, compliant, and persuasive. Storyboarding also accelerates the writing process by reducing blank-page paralysis, supporting early graphic planning, and revealing gaps in data or compliance before they derail schedules. In short, it gives teams the clarity and confidence needed to write stronger proposals. What Is Storyboarding? Storyboarding is the process of outlining the content and structure of your proposal sections before writing begins. Think of it as creating a blueprint: it shows the writer what to say, in what order, and with what supporting evidence. Storyboarding is important because: It keeps the writing aligned with the win strategy. Storyboards tie each section to evaluation criteria, customer hot buttons, and discriminators. It saves time. Writers work faster when they know what to write, and what not to. It improves consistency. When multiple authors contribute to a proposal, storyboards provide a shared vision that keeps the tone, content, and structure cohesive. Best practices for storyboarding include: Incorporate key messaging. Highlight your themes, benefits, and proof points in each section. Make them visual when possible. Use tables, diagrams, and callouts to plan graphics and reinforce major messages. Include RFP references. Tie each storyboard element to a specific section or instruction from the solicitation. Assign clear owners. Each storyboard should name a lead writer, contributors, and reviewers—along with target dates. Encourage teamwork and cross-reading. Storyboarding works best when it isn’t done in silos. Have multiple contributors work together to complete each storyboard. Then have the different section contributors cross-read the other storyboards to make sure there is consistency in the approaches. Storyboard Template Below is a sample storyboarding template that can be modified to align with your solutioning process. This format helps writers map out proposal content section-by-section, ensuring alignment with requirements, win themes, and the approved solution. - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -

How Making Proposals Easy to Score Will Improve Your Win Rate

By Ashley (Kayes) Floro, CPP APMP • February 24, 2026

Winning proposals don’t just happen because the solution is strong—they happen because the proposal is structured to earn points. Too often, teams focus solely on what they want to say, rather than how evaluators will read, interpret, and ultimately score their response. If you want to increase your probability of win, you must first understand how proposals are evaluated and then write with that scoring process in mind. By aligning your content to evaluation criteria, highlighting clear strengths, and making it easy for evaluators to assign high ratings, you can transform a compliant submission into a high-scoring, competitive proposal. Understanding Proposal Evaluation Before we can really understand how to make proposals easier to score, we have to understand how proposals are being evaluated. The first thing to understand is that proposals are typically first reviewed for compliance with the requirements as outlined in the proposal instructions. Next, the proposals are scored based on the evaluation criteria. Customers frequently assign strengths, weaknesses, and deficiencies to back up their scores. To receive an “Exceptional” score, your strengths have to outweigh any weaknesses, and no major deficiencies can be present. When using this scoring method, a deficiency is typically defined as a material failure of a proposal to meet a customer requirement or a combination of significant weaknesses in a proposal that increases the risk of unsuccessful contract performance to an unacceptable level. A weakness is defined as a flaw in the proposal that increases the risk of unsuccessful contract performance. And significant strengths are defined as aspects of an offeror's proposal that have merit or that exceed specified performance or capability requirements in a way that will be advantageous to the customer during contract performance. In our proposals, we want to minimize any weaknesses and deficiencies and maximize our strengths and significant strengths. Organize Content So It’s Easy to Score Understanding that proposals are scored, it makes good sense that when we’re writing proposals, we need to present the information in a way that is easy for evaluators to score. Most evaluators do not volunteer for the job and do not particularly enjoy it. It takes time away from their regular job, so they want to get it over with as quickly as possible. Therefore, we should aim to make the evaluator’s job as easy as possible. To make your sections easy to score, structure your response to the proposal instructions and the evaluation criteria. Next map in other requirements, as required (e.g., elements of the statement of work). To facilitate evaluation, consider including relevant RFP references in your section heading titles; this helps evaluators understand the logic of your organization and map your responses back to their evaluation scoresheet. Use RFP Language When writing proposals, you should also strive to use the language in the RFP to make the evaluation easier. For example, if the RFP asks for a Program Manager, you should use the title, Program Manager, not Project Manager. You should also strive to use the customer’s terminology and lexicon in our proposal to gain the customer’s confidence. By knowing your customer and speaking their language, you demonstrate that we understand them, and you begin to establish trust. What’s more, your customer evaluators often do key word searches to find what’s important to them in your proposals. To support them in this endeavor, you should make sure all sections include key words from the instructions, evaluation criteria, and the statement of work. Theme Statements Another way to help evaluators to score you higher is to include theme statements or strength statements consistently throughout your response. Theme statements set the stage for the section and grab the evaluator’s attention because they address an issue that is important to them. The ideal theme statement not only presents a solution feature that addresses a customer hot button, it also articulates clear, quantified benefits. I recommend including a theme statement for every first-level section and second-level subsection and formatting those themes to stand out from the rest of the text. If you theme effectively, the theme statements will show up as identified strengths in the evaluation debrief from the customer. Callout Boxes Another way to arm evaluators with the ammunition they need to give you a high score is to use callout boxes to help your major proof points stand out. Be sure that your proof points not only highlight quantified metrics, but make sure to provide the “so what?” statement as well. For example, it’s not enough simply to state: “We have used our proven staffing process to staff programs with 3-, 7- and 14-day turnaround times, including the MNOP program, where we staffed 15 FTEs in two weeks.” Ask yourself, “So what? What does this mean for my customer?” This might prompt you to add, “Leveraging this staffing process, we provide Customer ABC with low-risk task order start-up and delivery for large, small, short-term, and long-term requirements.” Feature and Benefit Tables Feature and benefit tables are another great way to help evaluators find proposal strengths. Similar to theme statements, feature and benefit tables highlight major solution features—that ideally address customer hot buttons—and articulate clear, quantified benefits. Typically, customers want things cheaper, faster, and/or better, which we might express as low cost, low risk, high quality, efficient, and/or effective. Use feature and benefit tables in each major section introduction to highlight the key elements of your approach. This could be every first-level section for shorter proposals, but it may be extended to each second-level subsection for longer proposals. Articulate Benefits Throughout As touched on previously, benefits tell the customer why they should care about our solution or its features; they articulate the “so what?” But, it’s critical to remember that benefits should be things that the customer cares about. For example, if the customer doesn’t care whether the transition is completed in three weeks or six weeks, then expedited timeline is not a benefit to that customer. It’s also critical to remember that benefits should be highlighted throughout the proposal narrative. It’s not enough for benefits to show up in theme statements, callout boxes, and feature benefit tables—these benefits need to be articulated and reinforced throughout the proposal narrative as well. Make the Response About the Customer Another critical way to score higher is to make sure you are focusing on the customer. Two key signs that your proposal writing lacks customer perspective include: (1) the proposal mentions your company or team name more than the customer’s name; (2) the proposal is about your company’s offer instead of the solution and benefits the customer will receive. A great proposal is about the customer and the benefits they receive from the proposed solution. One of the easiest ways to make our proposal content more customer focused is to put them first—literally. Instead of saying, “Team ABC’s solution delivers a low-risk transition,” flip the construction and write, “Customer A receives a low-risk transition with our comprehensive transition approach.” The two sentences convey the same overall message, but by putting the customer first in the sentence, we shift the focus onto what the customer is receiving rather than what we are delivering. Another easy way to make your proposal content more customer focused is to use the customer’s name more frequently than your company or team name. To validate whether you are doing so, you can try this quick test: hit Ctrl-F and search for the number of times you mention your company and/or team name; then search for the number of times you mention the customer’s name. You should aim to mention the customer’s name more times than yours. If you find that you have mentioned the customer far less frequently, you should revise our text to focus more on the customer and the benefits they will receive by choosing your solution. Final Thoughts In this world of bids and proposals, we all certainly want to win more. However, there are so many factors that impact a company’s probability of win, and a number of things throughout the opportunity lifecycle can impact a company’s chances of winning (both positively and negatively). Although the capture phase has the greatest potential to positively impact your chances of winning, you can certainly take steps to help your proposals score higher during the proposal writing stage. These actions include organizing content so it’s easy to score; using RFP language, theme statements, callout boxes, and feature and benefits tables; articulating benefits throughout the response; and making the response about the customer. These critical components during the writing phase can go a long way in facilitating the evaluation process and increasing your overall score—and a higher score can easily translate to a higher probability of win!

Writing Smarter: The Role of Artificial Intelligence in Winning Proposals

By Ashley (Kayes) Floro, CPP APMP • February 23, 2026

The use of generative artificial intelligence (AI) tools is becoming almost commonplace in our daily lives, much in the same way that we use cell phones and the internet without a second thought. And why not—it’s so easy to enter a prompt into ChatGPT and use the response to start an email, thank you letter, or social media post. So, it’s not surprising that the explosion of generative AI tools like ChatGPT, Claude, and others has sparked major interest—and debate—among those in the proposal community. AI promises so many benefits to our proposal process: it can save time and increase productivity, it can help brainstorm win themes and messaging, it can improve readability and clarity, and it can serve as a knowledge assistant. This can help reduce burnout on proposal teams since AI is saving the team time doing the “grunt work” so that proposal team members can focus on higher-value tasks. However, AI use does not come without potential risks, including confidentiality and data security risks. Inputting sensitive content—like solution content, past performance content, pricing, client names, etc.—into public AI tools can breach Non-Disclosure Agreements (NDAs) or contracts, expose proprietary or competitive information to third parties, or violate privacy regulations. Knowing the potential benefits, as well as the risks, you and your teams may be asking how you can responsibly use AI to draft sections, develop win themes, or tailor boilerplate content. And how can you do so without introducing AI generated errors? Let’s dig into it! How You Can Responsibly Use AI to Draft Sections, Develop Win Themes, or Tailor Boilerplate Content If used responsibly, you can use AI prompts to suggest creative ways to frame your team’s differentiators and benefits, help align your solution with the customer’s priorities and hot buttons, and provide alternative ways to express key messages to keep language compelling. You can also use AI to help rewrite dense, jargon-heavy technical text into clear, persuasive, customer-focused content. Here are some ways you can minimize risk while using AI to support proposal development: Set a policy and train your team Never input confidential or proprietary information into public AI tools Always treat AI output as a draft, never a final deliverable Set a policy and train your team Before you allow teams to start using AI to support proposal development, you should create a written guideline or policy. The policy should define when and how team members may use AI, which tools are approved, and how to mitigate risks while using AI. The policy should define clear boundaries for AI use, considering where it adds value and where it doesn’t. Remember, AI is good for things like: Drafting boilerplate content, like company overviews or standard capabilities statements (after it is fed with source materials) Generating ideas for win themes based on key differentiators and customer hot buttons you provide (note that capture still has to provide this information!) Helping tailor boilerplate to meet solicitation requirements Checking readability and suggesting stylistic improvements Summarizing content AI is not good for: Making compliance decisions: it may miss mandatory requirements Factual accuracy: it can invent or misstate facts Interpreting ambiguous solicitation language: human judgement is still needed for this! Once you set the guidelines, train your team! Make sure everyone knows and understands the guidance. Be sure to highlight the data privacy risks and concerns. For many companies, entering proprietary data into a public AI tool may be grounds for termination. Never input confidential or proprietary information into public AI tools Although we have already touched on this point, it really deserves some additional attention. But the bottom line is that you should never paste client-sensitive content, proprietary solution information, or internal pricing into tools like ChatGPT unless your company has a private, secure instance. Many public AI tools store user inputs and use them to further train their models. That means your sensitive information could remain on their servers indefinitely—and possibly reappear in responses to other users. Even with private, secure instances, some companies may be concerned with data breaches or cyber-attacks. If this is the case, consider developing a policy to redact or anonymize sensitive names and figures before asking AI to help tailor content, even in your private instance of the tool. Always treat AI output as a draft, never a final deliverable While I was at the APMP Bid and Proposal Conference in Nashville earlier this year, I heard a story about a team that was thrown out of competition because they used AI to write their proposal and then didn’t tailor it. The customer told them that another team submitted the exact same response. I am not sure I was able to hold back the level of shock that a team would submit content without adjusting it—but after hearing that story, this really needs to be said. For so many reasons, you should always review, revise, and tailor the content you receive from your AI tool. The best advice I have heard is to treat AI like a junior writer or assistant—its suggestions still need review, fact-checking, and editing by your experienced proposal team. Just like we have always done as part of our proposal best practices, have a human team member review all your content for compliance, accuracy, your specific proposal style guide, and tone—especially the content developed initially by AI. How Can You Avoid Introducing Errors or “Hallucinations” When Using AI? In the context of generative AI tools, a hallucination happens when the AI generates output that is factually incorrect or fabricated, but it still presents the information confidently, as though it were true. Examples of common AI hallucinations include: Inventing a certification your company doesn’t hold Citing a law, regulation, or standard that doesn’t exist Referencing past performance examples or customer names that aren’t real Providing made up statistics or figures Hallucinations happen because AI models don’t actually know or understand facts—they predict likely sequences of words based on patterns they’ve seen during training. When they can’t find the answer in the data they were trained on or in what you provided in your prompt, they sometimes simply generate something that sounds plausible. This is why, especially when teams are using AI, it is critical for proposal managers and Subject Matter Experts (SMEs) to actively stay involved throughout the process. Here are some steps you can follow to help avoid hallucinations and errors when using AI: Always start with a compliance matrix Get back to the basics: build your compliance matrix first and track every requirement explicitly. You can have AI generate a first cut, but then you need to go back and add in everything that the tool may have missed. Next, just as best practice has always told us to do, have a human peer review and validate the matrix. Then use the matrix as the source of truth, and verify that every section written, whether by AI or by a human, maps back to the correct requirement. Remember, AI can help you phrase responses, but it doesn’t reliably recognize all mandatory instructions, page limits, or formatting rules. Use AI as a support tool, not a decision-maker Remember that AI can draft, suggest, and rephrase, but it doesn’t understand the legal or contractual weight of a solicitation. We’ve mentioned this already, but always have a SME and/or compliance lead review every section of the response. Don’t throw out your best practice review cycles! Fact-check everything Again—another “old school” best practice that has become ever more important in the age of AI. Because AI is prone to hallucinations, it may confidently invent product specifications, certifications, client names, or achievements. To catch these errors, first make sure you provide the AI with accurate source material. Then as part of your review process, require the reviewers to check all the information, including data points, dates, names of agencies or organizations, and references to laws, standards, or regulations. Feed AI verified content: don’t let it guess Don’t ask AI open-ended questions, such as “What are the key benefits of our solution?” unless you also give it source content to work with. Instead, first give the tool your actual product or solution specifications, differentiators, and past performance examples and ask it to organize, rephrase, or summarize those into proposal language. Remember, only do this if you are using a paid/private version of the tool. Leverage secure, organization-approved AI tools If you are going to introduce AI tools into your proposal process, it’s best to use private or enterprise-grade AI systems that can be fine-tuned on your approved boilerplate and style guides. Public tools are trained on general data and will be less aligned with your standards—and they also pose serious confidentiality and data security risks if not used carefully. Final Thoughts As generative AI tools continue to evolve and become more embedded in our workflows, proposal teams have an opportunity to harness them responsibly and effectively to produce efficiencies in our winning proposal processes. By understanding both the benefits and the risks, and by establishing clear policies, training, and review processes, you can use AI to enhance productivity without compromising compliance, accuracy, or confidentiality. Ultimately, AI should serve as a supportive assistant, not a substitute for human judgment, expertise, and quality control. Remember: Always fact-check AI output against trusted sources Provide the AI tool with accurate, complete input material (don’t let it guess) Have SMEs review content for accuracy Don’t let AI generate sections from scratch without oversight With the right balance, AI can help your team work smarter, reduce burnout, and deliver stronger, more competitive proposals!