How to Win Over Proposal Evaluators

By: Sue Kuligowski    May 19, 2021     Kokopelli Insights

How to Win Over a Proposal cover

The first step to writing a winning proposal is winning over your proposal evaluators.

Yes, an accurate, clean, and complete response to the request for proposal (RFP) is essential. Yes, your differentiators and innovative solutions matter. And yes, pricing absolutely plays a role here.

But above all, you need to make sure that you are writing to the most important person in the room: the evaluator. It’s the first rule of effective writing: consider your audience. 

Before we dive into how to write a proposal that evaluators will love, let’s take a moment to talk about the most important person in the room—the evaluator.

Evaluators Are People, Too

Remember that scene in The Wizard of Oz where Dorothy and friends quite unexpectedly find themselves face-to-face with the “Great and Powerful” after Toto tugs aside a rather unassuming curtain?


We quickly hear fictional character and small-time circus magician Oscar Diggs’ (aka Oz) booming Oz voice call out, “Pay no attention to that man behind the curtain.” Turns out the Great and Powerful was just a regular guy and not quite as scary as first assumed.

And while I’m not suggesting proposal evaluators are scary (even if it may feel that way sometimes), it’s important to recognize evaluators are people, too. And while they do have special powers when it comes to deciding who wins the work, they are looking to you to solve their problems.

Some evaluators may understand the technical aspect of the project opportunity. Others may focus on making sure you’ve checked all the checkboxes and meet the desired qualifications to perform the work on time and within budget.

In all likelihood, you won’t know the individual evaluating your proposal unless you do some serious networking. That said, you should still take the time to do your research on the agency you’ll be approaching to get a good feel for the work they dotheir spending habits, the services they buy, and their present and future goals. 

Use data marketing websites to identify your target market(s), become familiar with NAICS codes, understand your customers, and learn about government contracting goals. Taking the time to research an agency can put you a few paces ahead of other respondents who may not know their history, what they do, or what’s on their horizon. 

Kokopelli Pro Tip: It’s imperative that you comply with all of the RFP requirements so that you don’t become a victim of a phenomenon known as thinning the herd. Evaluators tend to be overworked and overwhelmed. If your proposal doesn’t conform to instructions in the RFP, you can bet they’ll toss out your proposal to focus their time on the ones that followed directions.

Every piece of insight that you can glean is a nugget that you can potentially use to your advantage to develop your own unique proposal strategy and show evaluators that you’ve done your homework and you have the capacity to deliver on your proposal promise.

Now let’s get started: 

How to Win a Proposal Blog STEP-1

1) Read the Solicitation & Speak to the Evaluation Criteria 

Not only should you read the entire RFP, but you should ask a coworker to do the same. The more eyes to catch the details the better. Having a better understanding of a potential client’s business, challenges, and goals (not to mention requirements) helps you best frame your solution and show you’re the best choice to help them to be successful. That’s music to their ears!

Make it a habit to flip to the evaluation criteria to see if you are well positioned to win the work. While you may have the best of intentions, you must prove to an evaluator that you are able to perform the work better than the competition. You must meet the standards upon which the evaluator will score your proposal against others to select the one that best meets their requirements, has relevant experience, and offers the best value. 

How to Win a Proposal Blog STEP-2

2) Develop an Outline/Table of Contents that Doubles as a Checklist 

One way to ensure that you are responding to all pieces of information is by creating an outline (which may evolve into your table of contents) based on your content strategy and in alignment with what is being asked for in the RFP. In some cases, the client might tell you what to include and in what order.

A typical outline should show front matter, body of text, and attachments (for example): 

  • Cover 

  • Title page (if required)  

  • Cover letter/Executive summary 

  • Main sections (i.e., Team, Project Understanding, Past Performance, Approach, Cost) 

  • Attachments (i.e., resumes, project examples, or additional information) 

  • Required forms (i.e., addendums and acknowledgements) 

Kokopelli Pro Tip: The client may include a proposal checklist to be completed and returned with your submittal. While this may feel like just one more form to fill out, it’s a great opportunity to make sure you’re not forgetting anything important. 

How to Win a Proposal Blog STEP-3

3) Make a Strong First Impression 

You may have heard the expression, “Choose your weapon wisely.” In the world of proposals, it’s equally important that you use your space wisely. Covers aren't always required, and a good cover can't save a slapdash proposal. But they can be a great tool to signal the evaluator that you've paid close attention to the RFP. There are lots of clever ways to begin to tell your story through graphics relevant to the client or project, tag lines that tell them what they can expect from you, and teasers (think magazine covers) as to what’s inside and where they can find it.

Today, proposal writers understand that just like big city real estate, each square inch of your proposal is an opportunity to be used to your advantage. If and when it’s appropriate, don’t neglect your back cover space. It’s a perfect spot to drop a last (and hopefully lasting) impression or elevator speech with some bullets summarizing all the good things they’ve just read front to back.

Your table of contents doesn’t need to be a snooze fest either. If there’s one thing a busy evaluator may toast to, it’s a well-presented, well-organized proposal. For digital submittals, consider optimizing this important proposal tool by creating a clickable table of contents. Your evaluator will love and appreciate the included hyperlinks that will navigate them directly to a page of interest.

How to Win a Proposal Blog STEP-4

4) Introduce Yourself as Someone They will Want to Work With 

Your cover letter, executive summary, or introduction is an opportunity to tell an evaluator:

  • Who you are and what you do

  • Why you’re a great fit

  • How you can help the client to achieve their goals

Gut Check: If you’re read through their RFQ/RFP, and you can’t make a strong argument on why you’re a great fit with experience to back it up, it may not be a proposal worth pursuing.

Sounds easy enough, but many proposal writers struggle with identity issues when it comes to making a good and lasting first impression. You might present yourself as the greatest thing since sliced bread, but if they’re on a low carb diet and can’t make the connection as to how you fit their bill or solve their problem(s) early on, then you’ve lost them before they’ve even had a chance to bite into your killer technical approach.

An effective client-focused introduction states your qualifications to deliver what the client wants while clearly explaining benefits that are important to them.

Let them know that you understand their goals and challenges. Rather than tell, make sure to show that you are knowledgeable of their issue and have come bearing a risk-free, proven solution to help solve their problem. Demonstrate how and why you are the best technical expert on the block by showing added value that matters to them. Finally, use your introduction to launch into the best part of your proposal (technical approach) where you describe how you are going to answer their needs.

While evaluators may read through an entire proposal, they’re not robots and appreciate a solid summary just like anyone else. Use your introduction to your advantage by highlighting information that answers any “So whats?” they may have.

How to Win Over a Proposal wine label

Kokopelli Pro Tip: Think of your front matter and introductory information like a wine label, a book jacket, or clever product packaging—you want and need to hook your reader here to ensure they keep turning your pages rather than putting you down to check out the competition. 

How to Win a Proposal Blog STEP-5

5) Your Main Body Content Should Connect, Comply, and Qualify 

First things first, make sure that you read the fine print to ensure you are complying both with what sort of information is being requested about your team, experience, and technical approach, but also how they want to see it.

This is the delicate balance of proposal writing: injecting enough creativity to differentiate your proposal while making sure you remain responsive, respectful, and well within the constraints of the RFP.

Your main text is where you get your chance to demonstrate to the evaluator that you are the best fit for the job. It’s where you explain your great solution to help the client overcome their challenges and offer unique solutions. It’s where you can ease their mind by letting them know hiring you is a no-risk proposition.

Clearly, this is your chance to shine and you should summon all of your creativity to best show off how your team, past performance, and scope of work will add value and pay off big for the client. 

When it comes to “Project Understanding” and “Capacity to Perform the Work,” don’t just copy and paste from the RFP. The evaluator wants to know that you’ve processed the information they’ve provided. They will want to read your interpretation as well as why you think that you are able to tackle the job at no risk to them. Don’t dance around the question, answer them straight on leading them to the climax that will be your innovative approach. It’s up to you to prove to the evaluator that you understand what they need before you attempt to solve the puzzle.

At the end of the day, that’s really what it’s about, right? A proposal to fix someone else’s problem in the best way possible, at a reasonable cost, and on schedule.

While it’s tempting to simply spit back a potential client’s words in the Approach/Scoping section and say, “yes, we can help you with this,” evaluators are looking for you to break it down a bit and dig deeper. You need to show them step by step how you will approach the project by scoping out a workplan that demonstrates how you can do this and what’s in it for them.

You can count on the fact that your competition is going to boast that they, too, are capable of doing the work—it’s imperative that you differentiate yourself from the pack by explaining why your solution is in the client’s best interest. 

Kokopelli Pro Tip: Give them what they want. Resist the urge of skipping a question, section, or including information they have not asked for if it means that you will lose a point over it. It’s not worth the risk.

How to Win a Proposal STEP-6

6) Price Points that Speak to Evaluators

Proposal writing is a numbers game, too. And depending on the evaluation criteria, sometimes it matters more than others.

With government contracting, evaluators sometimes have to ask whether a proposal offers best value. Is it in the government’s best interest to consider a higher priced offer based on technical value over a lower priced contractor? Depending on the solicitation, some contracts are awarded by lowest price, technically acceptable (LPTA) meaning the award is granted to the contractor whose price is lowest so long as the proposal meets minimum technical demands.

How Low Will You Go

Gut Check: With LPTA evaluations, the emphasis is on the lowest price. If you don’t think you can offer the lowest price, then it may not be a proposal worth pursuing. 

Resist the urge to get lazy in the price proposal. Your cost section (sometimes it’s required as a separate volume) is yet another area you can use to your advantage to tell your client how or why you can do an amazing job at a fair price, or maybe even a lower price than your competition.

Maybe you can’t go any lower—so then you need to explain how and why investing in your expertise will bring added value that will result in a greater Return on Investment (ROI) for them.

How to Win a Proposal STEP-7

7) Let Your Strengths Shine

While it’s important to keep the focus of your writing on your client and their needs with a picture of that hard-at-work evaluator in mind checking off your proposal sections for better or worse, it’s okay to shine a little in an otherwise very technical process. Tooting your own horn is fine so long as you can prove to an evaluator that said toot will translate to project success for them. Sections like “Past Performance” are where you can really demonstrate to an evaluator that you don’t just talk the talk but prove that you’ve walked the walk—and will do so for them, too.

How to Win a Proposal STEP-8

8) Evaluate Your Own Response Before You Submit

Proposal evaluation can cover a lot of ground. Thoroughly review your proposal to make sure you’ve met the requirements and will rank high in relation to evaluation criteria before you seal your envelope or hit submit. Some of the main factors evaluators consider include:

  • Does the proposal clearly address the project and offer an innovative and applicable solution to the problem posed that stands out as better than the rest?

  • Does the proposal offer relevant experience or past performance of similar scope?

  • Does the proposal define the evaluation criteria and clearly demonstrate a low/no risk to the client?

  • Does the proposal identify assumptions and provide a clear path or technical approach that offers value to the client consistent with a fair market price?

  • Does your proposal provide them with an offer they can’t refuse (but in a good way, of course)?


In conclusion, while it’s tempting to dig in and get busy writing, make sure you’ve got a great game plan on how you’ll win over the evaluator. This blog was written through experience and lessons learned from over 15+ years managing proposals for Ecology and Environment, Inc. and now Kokopelli.

About the Author

Sue Kuligowski is a proposal manager at Kokopelli. She’s also a freelance writer/adoption advocate and part-time optimist who enjoys the finer things in life such as family, friends, and copious amounts of coffee.

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