Tips and Tricks for Winning Proposals
By Cheryl Smith
12 min read
Tired of blending in with the proposal competition? When you're meant to stand out? In today's competitive landscape, crafting a proposal that stands out is essential for business growth. It's time to elevate your proposal game.
This eBook is your guide to crafting proposal experiences that resonate. Packed with practical tips, proven strategies, and real-world examples, this resource will equip you with the knowledge and confidence you need to consistently deliver winning proposals that stand out. Get ready to transform your proposals from ordinary to extraordinary!
About the author
Cheryl Smith
Senior Content Writer
Cheryl Smith has been writing and managing proposals since 1998. Shipley trained, she has helped establish proposal centers and advised on capture strategy, coached orals teams and lead marketing, communications and knowledge management programs. Cheryl is a graduate of The George Washington University with degrees in Theatre, Communications and Literature.
A well-structured proposal begins with meticulous planning. Pre-kick-off planning helps you establish goals, responsibilities, and expectations, as well as tasks and deadlines. It also helps you communicate a single source of truth for accurately interpreting the RFP and articulating your value proposition.
Identify Decision Makers
Know your customer inside and out before you begin writing. Analyze their needs, challenges, goals, obstacles Understand their decision-making process and who the decision-makers, evaluators, and influencers are. This is who you want to engage, educate, and persuade.
Annotate Sections
Before writing begins, annotate sections with the customer and competitor details, value proposition, messaging, and scoring criteria your contributors need to write what is expected for review. Teams who annotate before writing are more likely to deliver on expectations without rewriting.
Standardize Content
Help your contributors skip the content search and stop recreating the wheel. Stock your library with reusable content for common requirements, frameworks for writing more unique requirements, and testimonials for argument supporting evidence. Add AI for surfacing relevant content faster.
Don't Forget About Design
Well-designed proposals are easier to read, navigate and understand. They engage readers and optimize impact. Allocate more space to important topics and to signal transitions between ideas. Use call-out boxes to get their attention. Use contrast to create visual interest and drama and connect similar ideas.
Planning keeps your team from falling down the rabbit hole.
Because they can more clearly see the ground they must cover. This helps them avoid the tangents and red herrings that distract them from focusing on the point they must get across to the reader.
Tip
The Plain Language Guide recommends simple words and short sentences of no more than 15–20 words, and paragraphs that average 3–5 sentences.
Think First, Then Write
What relevant stories can you share to show readers that you understand their challenges? That you have overcome these challenges for other customers? What objectives and questions might they have as they read? This helps you organize and prioritize, and deliver on expectations without major revisions.
Knock Down Silos
When contributors work in a silo, they can't see what others are working on. This leads to redundant effort and conflicting info. When you knock down those silos, you foster clearer communications that ease hand-offs and make everyone more efficient and more productive.
Tailor Reused Content
Reusable content is a time-saver, but evaluators can spot it a mile away. Leverage reusables by first separating the content from any context. Then, refocus the context on "what's in it for me" for impact. Infuse the content with a relevant, real-life detail for a lasting impression, and a bit of evidence as proof.
Write a Selling Exec Summary
The executive summary isn’t really there to summarize. It’s actually there to sell your value proposition to the decision-makers. Start with a compelling “why” followed by a focus on benefits and quantifiable proof. Above all, organize logically and keep it concise and clear. You want them to want to know more.
Proposals are living documents, and reviews and revisions are an important part of the development process. Done collaboratively, they refine your message, strengthen your argument, and amplify your value. By mastering this art, you transform a promising draft into a persuasive masterpiece that stands out from the competition.
Assemble Diverse Review Team
A reviewer should really not be a contributor. You want fresh eyes for objective insights without bias. Independent reviews from senior management, subject matter experts, and project managers, to people who are not experts in this field bring valuable readability perspective.
Define Expectations
To optimize your reviews, tell your review team what you are looking for. Ask for expertise and instructions, not opinions. Done right, reviews reveal a clear roadmap for revisions. This includes consensus on how to improve messaging, strengthen arguments, showcase evidence, and amplify value.
Simulate Customer Evaluation
Would you award this bid? Understand who wields the power to turn your proposal into a project. Review with these customer roles in mind; gatekeeper (screens your proposal), expert (assesses feasibility), evaluator (scores criteria), and decision-makers (weighs recommendations for final decision).
Stage Collaborative Reviews
Hold collaborative reviews so reviewers and contributors can question, clarify and come to consensus on revisions real-time. By fostering shared ownership, you'll harness the collective wisdom of your team. And uncover fresh perspectives that enhance quality and accelerate revisions.
According to APMP, 49% of organizations say they plan to increase the number of RFPs they respond to in 2024.
Remove Roadblocks to "Yes"
Transform your proposals from "maybe" to "yes" by identifying and eliminating hidden solution and project doubts and objections. Address these logically in your narrative as you feel they might surface in the reader's mind. This positions you as a problem-solver with experience and foresight.
Sharpen Your Content
Revisit each section for clarity, conciseness, and a logical flow of information. Eliminate jargon and redundancies. Strengthen your arguments, and ensure your claims are supported by compelling evidence. Try reading out loud to reveal any awkward phrasing, inconsistencies and missed transitions.
Enhance Readability
Avoid complex sentence structures. Break up text using headings, subheadings, and bullet points to improve scanning. Incorporate graphs, charts, and images for impact. Give readers time to think with white space. Above all, use a clear and consistent layout throughout your proposal.
Ease Expert Hand-offs
Maximize efficiency and minimize disruptions with seamless workflow between experts and contributors. When you ease hand-offs, you unlock the process logjam, eliminating delays and accelerating timelines. No one wastes time working on the wrong tasks in the wrong document version.

Your proposal is complete. Submission is the culmination of your hard work. Sometimes that means a digital submission via email or portal. Other times that means printing copies of the proposal and delivering it to the issuing agent. Either way, let's ensure it reaches it's destination with impact.
Reformat
You established your layout and formatting before writing began. It's been disrupted during development, and now you have to touch every page, paragraph, and sentence to reformat. Enforcing your layout and formatting during development eliminates the last-minute sprint.
Proofread
Ensure your proposal leaves a flawless impression. Focus on one thing at a time, checking for grammar, and punctuation. Scan for images slipping off the page. Read out lout to identify awkward phrasing or missing words. Step away and take regular breaks to keep your eyes fresh!
Submit and Confirm
Double-check deadlines and adhere to guidelines. Once submitted, send a brief email to the RFP contact confirming your submission and expressing your appreciation for the opportunity. Indicate your availability for any clarification questions. Track your submission and keep your eyes on your email!
Congratulate Your Team
A lot of time and effort went into developing your proposal, and it wouldn’t be possible without your team. Kudos team! At this point, fight the urge to remind them that there is another proposal that needs their attention. Let them enjoy their accomplishment for a few minutes.
Continuous improvement is the cornerstone of proposal success. By capturing and analyzing lessons learned, you can enhance future proposals and drive better results. Teams who regularly evaluate and improve their process execute a more seamless transition from RFP and development to submission and award.
Eliminate Overselling
If your proposal feels unrealistic your readers will be skeptical. This sets a dangerous tone for their evaluation. Acknowledge limitations or potential challenges or obstacles upfront. Offer options or alternative approaches. Avoid exaggerated claims and promises. A realistic approach builds trust.
Eliminate Repetitive Tasks
Entering the same client information repeatedly is time-consuming. So is updating it across large, complex proposals. By eliminating the need to re-enter the same information multiple times, proposal writers increase accuracy and consistency, and focus their time on creating compelling content.
Eliminate Accountability Confusion
Show contributors how each of their tasks connects to all of the other contributor’s tasks. When everyone understands where their piece of the puzzle fits, everyone is more likely to collaborate and hit their deadlines. This saves significant time better invested in advancing your proposal content quality.
Eliminate Status Doubt
By centralizing proposal development, including writing, reviewing, and approval, you implement a clearer process. Teams confidently track their tasks and deadlines, eliminating hand-off delays. Armed with this real-time intel, managers know when to step in and address bottlenecks before they become delays.
Conclusion
Crafting a winning proposal is a collaborative journey that requires contributions from a diverse set of individual skills, knowledge, experiences and perspectives. By fostering collaboration, you make it easier and faster to harness the knowledge of your collective expertise. The result enhances proposal quality, increases efficiency, and ultimately drives better business results.
Discover more content
Proposal Management Best Practices That Win More Bids
Master proposal management best practices to improve your win rate, streamline teamwork, and deliver high-quality proposals on time, even u...
June 04, 2025
What is Proposal Management? A Complete Guide for Teams
Proposal management is the process of planning, writing, and delivering business proposals—often in response to a Request for Proposal (RFP...
April 11, 2025
The Ultimate Proposal Management Checklist
Cheryl Smith’s top tips for creating a comprehensive proposal management checklist, including compliance matrices, outlining tasks, and def...
October 10, 2024