Five Tips for Writing a Winning Proposal

by Samantha Enslen


Writing a proposal is hard.

There’s rarely enough time to give it the attention you want. You don’t always know much about the client, so you feel like you’re writing in the dark. The client may have an unrealistic budget, meaning your cost will knock you out of the running, no matter how well you’ve described your solution. What’s more, they may already have an awardee in mind and are only going through an RFP process as a formality.

As writers, we can’t do anything about the last two points. There will always be factors we can’t control that affect whether we win or lose.

All we can do is focus on what we can control: our attitude, our effort, and our preparation. Here are several ways we can do that.

Be Empathetic

Good proposal writing (and other good writing, for that matter) starts from a position of empathy. Before you think about writing, and long before you start developing a solution, ask yourself these questions: What is my customer struggling with? Why did they issue an RFP? Why now? What keeps them up at night?

Gaining insight into these questions is what’s known in our industry as “capture”—a fancy word for the effort required to deeply understand your customer’s environment and challenges. APMP Fellow David Bol calls capture “the most important part of the proposal process … absolutely critical to the probability of winning.” (1)

Empathy is the first step in figuring out how to help your customer. You must understand that before you can put together a meaningful solution.

Be Authentic

Once you understand the challenges your customer is facing, the next questions are, “can we actually help them—and do we want to?” In other words, can we help them in a way that brings them genuine benefit—and aligns with our business model, is profitable for us, doesn’t sap our resources, and may help us to get more business in the future?

These kind of questions drive what are known in the proposal world as bid/no-bid decisions, or gate decisions.

If the answer to any of them is “no,” you may want to stop right there.

If the answer to any of them is “sort of,” you have some thinking to do. There’s nothing wrong with stretching to go after a bid in a new area, if it fits well with your business model. It’s another thing to fudge a response and pursue a job you’re truly not suited for.

I speak from experience: things won’t turn out well.

Be Positive

Once you’ve decided to move forward with a bid, throw yourself into it, heart and soul. Your enthusiasm will be conveyed in both your attitude and your writing.

Proposal environments can be stressful. So again, focus on what you can control. Ask yourself what kind of proposal professional you want to be? The kind who snaps at subordinates? Who gives feedback at 5pm, when Red Team is the next morning? Who blames the production team for a loss, when capture would have revealed the bid was a dud from the start?

Or do you want to be known for sharing a ready smile and a silly joke even under harsh deadlines? For letting your colleagues know how much you appreciate their hard work? For looking at losing bids with a spirit of learning, rather than blame?

Positivity is contagious. In the proposal environment, it can mean the difference between a team that’s excited or dismayed about upcoming bids. Strategic Proposals’ 2020 report, “Mental Health and Wellbeing in the Bid and Proposal Profession,” made this abundantly clear. (2) The need for proposal pros to take care of each other—rather than push each other to the breaking point—is of paramount importance.

You can convey this positivity in your writing, as well. You can write with confidence, saying “we will provide health screens on all returning employees within 48 hours,” for example, rather than “we can provide” or “we would provide.”

You can convey energy by writing in active rather than passive voice. Say “our event managers will carefully organize your virtual conference,” for example, rather than “your virtual conference will be carefully organized.”

Be Persuasive

There’s nothing I can say on persuasive writing to top Tom Sant’s Persuasive Business Proposals or the content in the “Persuasive Writing” section of the APMP Body of Knowledge. (3,4) However, I’ll say this. Being persuasive is not about being “salesy” or somehow tricking your reader into thinking that you’re the best.

Rather, being persuasive is the outcome of all the above traits. If your writing is empathetic, it will focus on your customer’s needs and preferences. If your writing is authentic, you will show that you share the same values and goals as your customer. If your writing is positive, it will demonstrate that your solution is the most likely to succeed—and to help your customer be successful.

Being specific in your solution is also important.

For example, you could write generically and say “our event staff will provide comprehensive service for conference sessions.” Or you could be specific and say this: “One event manager will serve as host for each virtual conference session, two event assistants will answer comments that come in through chat, and a third event assistant will monitor social media and respond to comments that appear there. A technical specialist will also be on hand to help attendees who are having difficulty connecting to the session.”

Be Consistent

I said you should “be authentic.” How authentic is it if the content in your technical section conflicts with the content in management? Or if the labor categories you list in cost don’t line up with what you’ve described in your narrative?

Substantive issues of consistency should be caught during final document review (aka, Red Team review), if not sooner. Other issues of consistency should be caught by your copyeditors, who often review the document after Red Team. Their work can get done more quickly and accurately if they use a consistency checker.

Enter PerfectIt. The beauty of PerfectIt is that it can automate the most time-consuming parts of editing a proposal, leaving your team time to focus on value-added tasks like clarifying meaning and enhancing readability.

Here are a few of the onerous tasks that PerfectIt can automate:

Reconciling Acronyms

This can be the most laborious part of proposal editing: making sure that each acronym is spelled out at first reference, that the full term is removed on subsequent reference, and the acronyms that are used only once are removed from the text. There used to be no easy way to do this, especially when content stretched across hundreds of pages and multiple volumes.

PerfectIt does this with the click of a button, identifying areas where acronyms are used incorrectly and walking you though each instance one by one. Bonus: it also generates an acronym table for you, saving the hours of work required to create one manually.

Checking Figure and Table Numbering

If you work on proposals, you know that figures and tables can change hourly. Pretty soon, numbering is whopperjawed and callouts are missing, even if you’re using Word’s autonumbering feature.

Copyeditors can fix this manually, but why not have PerfectIt help? With one click, PerfectIt can instantly identify figures that are wrongly numbered or that are missing numbers or callouts. Running this check is so much faster than scanning lengthy proposals page by page.

Fixing Capitalization and Hyphenation

Have you ever worked on a federal proposal? If so, you’ve seen the cornucopia of ways that terms are handled. Are we providing life cycle, life-cycle, or lifecycle support? Are we writing to DoD or DOD? Are we providing services to Warfighters or warfighters? The list goes on and on.

Once again, PerfectIt shoulders the burden of checking for consistency and outshines plain vanilla spellcheckers. It’s smart enough to recognize that “lifecycle” and “life-cycle” are the same term; ask you which one you prefer; and then auto-fix all of the incorrect instances for you.

Checking Capitalization of Headers and Subheaders

Wow, could any task be as boring as checking the capitalization of headers? (OK, doing a compliance check might be. But this is up there.)

PerfectIt does this automatically. It allows you to choose whether you want title case, sentence case, or initial caps, and then it automatically imposes this style across all heads and subheads. How is it smart enough to do this? I don’t know, and I can only suggest MAGIC. But the feature works, it’s fast, and I use it all the time.

Writing a Winning Proposal

Creating proposals is a stressful proposition. There’s so much work that goes into understanding your client and your competition, crafting the right solution, picking your “price to win,” and writing persuasive content. It can be overwhelming if you don’t recognize just how much control you have over the process. Approaching this work with empathy, authenticity, and positivity can help. So can taking advantage of time-saving tools like PerfectIt.


Samantha Enslen runs Dragonfly Editorial, an agency that helps companies worldwide create clear, powerful content. Sam is vice president of ACES, The Society for Editing, and the former managing editor of ACES’ quarterly journal, Tracking Changes. At Dragonfly, she leads a team of writers, editors, and designers who often use PerfectIt to help them polish their copy.



  1. David Bol, Model Train Builder and Visionary Leader. Scribble Talk Podcast, Episode 17, 2020.
  2. Mental Health and Wellbeing in the Bid and Proposal Profession. Strategic Proposals LTD, 2020.
  3. Sant, Tom. Persuasive Business Proposals: Writing to Win More Customers, Clients, and Contracts. AMACOM, 2012.
  4. Persuasive Writing. Association of Proposal Management Professionals Body of Knowledge. (available to APMP members only).

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