Mastering Government Contract Proposal Success with Bill Pratt

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Mastering Government Contract Proposal Success

In federal contracting, understanding how proposals are evaluated directly impacts your ability to win. That was the focus of a recent webinar hosted by Sean Doherty, CEO of GovDash, featuring Bill Pratt, President of GovITWorks and former Director at the Department of Homeland Security.

The session provided practical guidance for contractors seeking to enhance their government proposals, from understanding evaluators' perspectives to structuring an executive summary that captures attention.

Understanding the Evaluator’s Mindset

Sean opened by framing the discussion around the “evaluator’s mindset.” Bill explained that evaluators work under strict timelines and formal processes. Every minute counts. That means proposals must be clear, compliant, and concise.

What Evaluators Look For

Bill reinforced a core rule: align proposals tightly with the evaluation criteria.

"RTQ; read the questions. In this case, read the requirements of the proposal and answer them directly."

He also detailed how program managers and contracting officers balance priorities. PMs focus on operational and mission success, while COs focus on best value and compliance. Evaluations typically use score sheets that measure clarity, risk mitigation, traceability, and staffing.

Avoiding Common Pitfalls

Bill didn’t hold back when calling out mistakes that sink proposals early: vague claims, generic boilerplate, or design-heavy submissions that lack real content.

"A lot of times, what I see is folks are spending extra time on gloss and not so much time on easily found content... Evaluators can spot boilerplate instantly."

He also warned that skipping compliance details can be fatal:

"Ignoring the structure and compliance… Nonresponsive submissions will be an automatic loss."

Ensure evaluators can quickly find every answer and reference they need, with no digging required.

Crafting Executive Summaries That Resonate

Bill compared the executive summary to a TED Talk opener, your first few seconds to capture attention.

"This is your opportunity. This is your first, five seconds of a TED talk. Here's what we're gonna do, and here's our understanding of what your challenges are here."

He urged contractors to align their executive summaries with the agency’s mission and challenges. Avoid recycled text, make it specific, mission-driven, and human.

Competing Against Incumbents and Low-Ball Bidders

When asked about incumbents and “loss leader” bidders, Bill was direct.

On incumbents:

"We're not authorized as the technical evaluation team to take into account our personal knowledge of how good you are if you're not stating it right there."

On low bids:

"What that's telling me as a PM is...they don't understand the work well enough to think they’re gonna come in and do all this work at that price."

His message: incumbents don’t get a free pass, and unrealistic pricing signals risk, not value.

The Human Element in Evaluations

Bill also discussed the value of oral presentations in understanding a team’s capabilities.

"I actually insisted on doing orals first because I wanted to look these folks in the eye and hear what they had to say, and I wanted to hear it in their voice."

He shared a story about a disengaged team during an oral presentation:

"After introductions, three folks sat on bar stools and didn’t say a thing."

Evaluators take note of engagement and teamwork. Bring authentic energy and unified messaging to every interaction.

Practical Tips for Winning Proposals

Bill closed the session with actionable takeaways that every GovCon team should internalize:

  1. Prioritize clarity and readability.

    "Don’t make me dig through that sentence to get the gold nugget I need."

  2. Demonstrate past success.

    "Here’s our past experience...has won us awards with similar success in similar scenarios."

  3. Use agency language.

    "Make sure you're embedding some of that language into your proposal."

  4. Get an outside review.

    "Nobody wants to say their own baby’s a little bit ugly...You'll learn so much."

Final Thoughts

Sean wrapped up the session by thanking Bill and attendees. Bill left the audience with a reminder that excellent proposals don’t just check boxes; they minimize evaluator risk and align with customer mission needs.

"Thoughtful, disciplined proposal writing wins contracts."

For contractors serious about improving win rates, this webinar delivered clear, experience-backed insights on how to think like an evaluator and write like one, too.

How GovDash Helps You Build Winning Proposals

If you’re ready to write proposals that evaluators love to score, GovDash gives your team the advantage.

GovDash centralizes everything you need to build compliant, compelling, and data-backed proposals, from past performance insights to evaluator-ready narratives. No more chasing documents or formatting chaos. Just one platform built for how federal contractors actually work.

Whether you’re managing capture, pricing, or proposal operations, GovDash keeps your team aligned and ensures consistent submissions across opportunities.

Want to see how GovDash helps top GovCon teams write faster, win more, and reduce evaluation risk? Book a demo today and start building more innovative proposals that win.

Watch the full webinar on-demand

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Less expensive than a lost bid

Submit the form to schedule your GovDash tour and get your custom quote started.

By clicking "Submit," you agree to the use of your data in accordance

with GovDash’s Privacy Notice, including for marketing purposes.

© 2025 All Rights Reserved. Made in America 🇺🇸

Less expensive than a lost bid

Submit the form to schedule your GovDash tour and get your custom quote started.

By clicking "Submit," you agree to the use of your data in accordance

with GovDash’s Privacy Notice, including for marketing purposes.

© 2025 All Rights Reserved. Made in America 🇺🇸