How to Win a Federal Contract

An Article of The Modern Survival Guide, Vol. II

Photo by Sora Shimazaki, courtesy of Pexels.com

I’m going to let you in on a dirty little secret. Are you ready? Here it is, and don’t tell anyone — the United States Federal Government employs more than 4 million private contractors. How many more than 4 million? No one knows. But that’s a pretty hefty chunk of the US active workforce right there, so odds are pretty good that someone you know is on a contract working for the feds.¹ And when you figure that federal contracting is a $550 billion industry, it’s easy to see how this topic made it into a series called the “Modern Survival Guide.” That’s a lot of cash, a lot of jobs, a lot of lives affected.

Winning contracts with the federal government is, increasingly, a big part of the livelihood of a lot of families. Losing contracts with the federal government is, increasingly, a big part of the stress of a lot of families. I’m going to tell you how to win more than you lose.

Ok, let’s start with a cards-on-the-table moment: I am an employee of the government. No, I can’t tell you which agency. Part of my job is to sift through contract proposals and try to pick out the “good” ones from the “bad” ones. Under our current rules of procurement that is an absolute joke, and it’s not actually what I’m here to talk about today. Today, I just want to help you land a contract. Your livelihood might be on the line, and that’s something we take seriously here at the Modern Survival Guide because… um… it’s in the title. Survival and whatnot.

In this article I’ll tell you how to win a federal contract, step by step. I’ll be talking about a very specific kind of contract — there are other kinds, and they’re less interesting, so I won’t go into them here. The kind I’m talking about is one in which you have looked up a contract opportunity on SAM.gov and found yourself a juicy RFQ (request for quote) contract solicitation. If you’re not sure what those words mean, feel free to close this tab, because this article isn’t for you and the jargon gets worse.

Your company has replied to the RFQ and you now find yourself the proud recipient of an invitation to submit a proposal, with attached Statement of Work (SOW) and evaluation template documents. Your boss tells you to write a proposal. Lovely. Now what?

Now you need to avoid all of the traps that can wreck your proposal, and there are a LOT of them. You also need to do quite a number of things right. To explain all that, I’m going to break down the rest of the article into four sections, and they are:

• Organizing Your Proposal
• Writing Good Content
• Demonstrating Excellence
• Managing Resumes

In each section I’ll give you an idea of what to do and spell out some of the more common traps that I see people fall into. And why am I doing this, you ask?

I’ll tell you why.

It’s because I’m tired of being subjected to awful proposals, when it’s so easy for you to do better with a little guidance and make my life easier. I should emphasize that this will in no way, shape or form, actually result in better contracts for the federal government; that’s a whole separate discussion. This is about you getting past me in the most efficient manner possible so that I can get on with actually trying to do work, from which proposal reviews so frequently distract me. Purely selfish motivation. You’re welcome.

Organizing Your Proposal

Let’s consider this rationally, shall we? If you are replying to a federal RFQ, and you’ve been given an SOW, and they’ve given you a copy of the evaluation form that will be used to judge you, then the government has already done half of your work for you: they’ve told you what they want, and they’ve told you how they’re going to be assessing your reply.

The best thing you can do under these circumstances is to organize your proposal in such a way that it matches these documents.

You have to understand that the feds who review your proposal, like me, are not just looking at your proposal. They’re looking at you and everyone else who submitted a proposal. That’s a stack of paperwork as long as your arm (often longer) for even a low-bid contract. It’s going to take those people days to plow through it all. They will get tired. They will get bored. They will get frustrated. And if you make them hunt through your proposal to find what they’re looking for, they will get mad.

Obviously, that’s a disadvantage to you.

Rather than walk that path, here’s what you do to make their lives easy, so that they like you: tailor your proposal’s organization to the evaluation form.²

You’ve got it right there in front of you; you know the things the reviewers will be looking for, and you know the order in which they will be looking for them. Start at the top and create a major section in your proposal for each evaluation question. Copy each question into the proposal as a section title. Then reword that question into a “we will” statement.

For example, if question 1 of the evaluation form is “Does the Offeror (that’s you) explain how they will develop Widget A in compliance with CMMI base principles?” then section 1 of your proposal should damn well be some version of “Here’s how we will develop Widget A in compliance with CMMI base principles.” Use as many of the same keywords as you can from the evaluation form to make your proposal easy to search; remember, the evaluator is looking at potentially dozens of submission, and if you make it hard for them to find things then don’t expect them to find things. You’re not getting points for creativity in section titles; in fact, rather the opposite.

With this in mind, your high-level proposal organization should be: formal response memo (follow the template they give you) -> table of contents -> introduction to your company -> restated evaluation questions in sections -> resumes -> applicable work experience. The government may request that last part in a separate document. If you follow that rubric, you can’t go too far wrong in organization. If they give you a different rubric to follow, use that instead.

Organization Traps

There are a lot of things to keep in mind here, so I’ll summarize:

• Do not write your perfect proposal: The federal government is not interested in your perfect proposal. The reviewers do not care. They want to see the things they asked to see in the SOW, in the order required by the evaluation form. Your idea of the perfect proposal organization is, at best, moot. Write what the reviewers expect to see, not what you want to write.
• Avoid mixing up sections: One of the worst things you can do is to organize some of your sections by the SOW, some by the evaluation form, and some by your own personal preference. I personally would not advise organizing your proposal around the SOW in most cases, but if you do that, stick with it and tag each section with the evaluation question it ties back to. Don’t flip back and forth. Don’t mix up the order. Don’t cross the streams, Ray.
• Don’t bother putting resume information in the main sections: This happens all the time; people like to brag about their project managers, or foremen, or technical leads, or whoever. Unless an evaluation question specifically asks for this information, or the SOW demands it, don’t bother. As a general rule, federal evaluators take a dim view of contract proposals playing up personnel because we all know how insanely easy it is for contractors to bait-and-switch their people.
• Don’t bother putting past experience information in the main sections: Lots of contractors like to do this, either in the main text or in cutesy little call-out boxes. Don’t bother. You’re just eating space you could be using to tell the government how you’re planning to do their work. When they want to see how you did someone else’s work, they’ll look at the past performance section.
• Don’t forget your editor: This is also true for the content discussion, but I’ll say it here as well — if you can’t be bothered to get the basics correct, you’re done. If you miss an evaluation question, you’re done. If you miss an SOW section, you’re done. If you copy/paste the wrong information into a section, you’re done. Find someone in your organization who is Type-A to the max, and have them read your proposal and line it up against the SOW and the evaluation questions. Make sure you caught everything — even the niggling little sections at the bottom of the SOW that no one reads may have some key requirements.
• Don’t make it too complicated: KISS is on tour in contract proposal formatting — Keep It Simple, Stupid should be your watchword. Don’t over-format your text. Don’t add in tons of call-out boxes or highlighted sections. Don’t use footnotes if you can help it. Don’t generate six thousand nested sub-sections. If you go past 1.1.1 in your subsections, you’ve gone too far, turn around and come home to 1.1.

If you can avoid these traps, you’re already doing better than about half of your competition. That’s enough to move you on to the actual content review.

Writing Good Content

Ok, so your reviewer can pretty much find their way around your proposal. Now what?

Now we turn to the SOW, and this is where things get sticky. You have to generate content that makes you sound better than your competitors. There is exactly one way to do this: tick every single box on the SOW, and then explain how you will do every single item on the SOW using the “who, what, when, where, why, how” pattern of elaboration.

Start with an SOW review. Have that Type-A person in your organization look at the SOW and write down each major point as a checklist on a piece of paper, or do it digitally and print out a copy of that checklist. These are usually found in the Contract Line Items (CLINs) of the SOW, but there may also be additional requirements scattered throughout the other sections of that document.

Note that you don’t have to address every section of the SOW. Most of the stuff at the bottom is boilerplate. But anything that you are being asked to do as part of the contract work, you should address. Also note that if you only write your checklist at the CLIN level, you’re too high up and you will miss things.

If you want to be extra-safe, I would always recommend having someone else check your Type-A person’s work. The federal evaluators operate in teams so that what one person misses, the next person will catch. You should do the same thing.

Having a hard copy of your checklist makes the next part easier: add a paragraph header into your proposal for every single item on that list, working them into your established sections. Physically check the items off as you add them to your draft. It really will make it harder to miss things. Surgeons and pilots do this, why shouldn’t you?

As with the section headers, a safe way to do this is to copy and paste the key points of the SOW into your proposal, and then reword them to be “we will” statements. If part of the SOW says, “The Offeror will develop Widget A to tolerances of 99%,” part of your proposal should read, “We will develop Widget A to tolerances of 99%.” Is this cheating? Hell no! It’s just your opening move. Just make sure you catch all of the copy/paste statements and reword them; an easy way to do this is to copy in this stuff as highlighted text or different colored text, so that it stands out.

The next step is to substantiate these statements. Again, you want to tell the reviewer who is doing the work, what is being done, when it’s being done (key point — always check deliverable tables and make sure you copy over the due dates), where it’s being done (if applicable), how it’s being done, and why your way is better. This is where the art comes in, because I can’t tell you how to write those things to make them pop. It’ll be particular to your contract and your company. But it you don’t do this, I can guarantee you will lose the contract to someone who does.

Coming back to organization for just a moment, in many contracts you will notice that the evaluation template and the SOW do not necessarily align 1:1. Evaluations are frequently performed as qualitative measures; in these cases the evaluation statements are typically broad-scope. If you are organizing your proposal against a qualitative evaluation, you’re going to have to make a determination as to which SOW sections belong in which evaluation sections. If you’re organizing your proposal against the SOW, as might be the case when dealing with a quantitative evaluation, then flip that script and reverse it; now you have to figure out which evaluation sections belong in which SOW sections.

Either way, don’t feel too bad if you mess up a little bit and put one or two things in the wrong section. This is where things get squishy, and the reviewers won’t judge you too hard unless you make your information hard to find.

In any case, make sure you are tagging your response with either the SOW section or the evaluation section that is relevant. Keep things organized by doing this tagging in the subsection header (but again, don’t go too crazy with subsections). That will make it show up on the table of contents, which then becomes your reviewer’s guide for walking through your proposal. How often is the table of contents utterly useless from the perspective of an evaluation reviewer, you ask? Far, far too often. Fix that in your proposals.

With that in mind, ideal content should look something like this:

Section 1: My Company Will Produce Widget A to Quality Standards (Evaluation Question 1)

Subsection 1.1: Producing Widget A with 99% Quality (CLIN 003, SOW Section 75)

Text: My Company has an excellent track record of producing Widget A with 99% quality. Our project manager, Ms. M, will serve as the primary point of contact for the production of Widget A, and will oversee Mr. S and Ms. Y, My Company’s team leads for this project. We will produce Widget A in lots of 75, per the government’s specification in SOW Section 75.9000, meeting the delivery date of When You Want It. All production will take place at our facility in The Dark Swamp, and we will transport the completed lots to the specified warehouse at The Far Side of the Moon. We are a trusted producer of Widget A due to our propriety quality standards of We Do It Right The First Time and We Use Good Materials, which ensure less than a 0.00001% fault rate. We verify this high reliability rate by conducting product checks according to the industry-standard methodology of Reaching Onto The Conveyor Belt And Looking At The Damn Thing. Also, we’re cheaper than the other guy by THIS MUCH.

Get the idea?

Similarly, if you need to write a separate past experience section, you should write it in such a way that you clearly call out the evaluation questions. Each example that you cite should (a) meet the requirements given for examples (there are always some boxes to check), and (b) incorporate the evaluation questions to the greatest extent possible.

Past experience content might look something like this:

Prior Experience: Working for Dr. Evil at Mt. Doom (2018–2020)

Status: Prime managing two subcontractor, Orcs Inc. and Evil Space Goblins, LLC

Relevant Work for Quality Standards: My Company demonstrated successful production of Widget A for Dr. Evil, delivering production lots of 8,000 on a timeline of Whenever He Wanted Them. We achieved a 99.5% quality rating utilizing the proprietary methods of Thinking Ahead and Using Basic Statistics To Predict Fault Tolerances. Dr. Evil praised My Company as an excellent partner and has given us a consistently high CPARS rating.

In any instance, writing good content is all about restating the goal, explaining how you can do it, and explaining why you’re good at it. If you remember “who, what, when, where, why, how” you can’t go far wrong.

Content Traps

There are a number of things you can do wrong writing content for a contract proposal, and once again, here’s a summary list:

• DON’T LIE: Did I need to put that in all-caps? Yes. Yes I did. I see this all the time. It’s oh-so-tempting to take credit for things you didn’t do, isn’t it? Well, knock it off, because the thing about evaluation review teams is that they’re drawn from the people who are overseeing the current contracts. They tend to be subject matter experts, and they tend to check on this kind of thing. Remember, once you lose trust you don’t get it back.³
• Don’t miss the SOW: It’s very, very easy to miss an SOW section, particularly all the minutia around deliverables. Double-check your work to make sure you caught everything. You can sometimes get away with not directly answering an evaluation question if you get every single scrap of the SOW into your proposal and knock your demos out of the park.
• Don’t miss the evaluation questions: Most of the time you can’t get away with missing an evaluation question; they are often distinct enough from the SOW that you will need to write to them directly. Make sure you have written to all of them.
• Don’t add Useless Visuals: Almost every proposal I’ve ever read has contained at least one Useless Visual. This is a picture, chart, or graph that looks cool to your manager but doesn’t actually convey any information. You really want to avoid adding these, because it trains the reviewer to ignore your pictures. Sometimes pictures can be very useful… but not if the reviewer skips them out of defensive reflex.
• Don’t forget to update copied text: Especially when you copy sections from other proposals, you need to be very careful about copy/paste. It’s very, very easy to accidentally drop in a line you didn’t mean to, or forget to change an evaluation question to a proposal statement, or to accidentally include a different proposal reference. Again, it’s wise to mark all copied material with highlights or different text colors just to make sure you catch all the material.
• Don’t repeat yourself: The evaluators are going down a checklist. You do not get points if you repeat items on that checklist, and repetition eats up precious page space that you really should be using to substantiate your claims of greatness; remember that all proposals have a page limit.
• Don’t just say “we will”: I see this all the time too; you really have to do more than restate the SOW in “we will” format. That’s enough to check the boxes and avoid getting a deficiency marking; it’s not enough to win you the contract.

This isn’t an exhaustive list, but if you avoid these traps you’ll be doing better than most of the rest of your competition. You are now in a position to be competitive about actually winning the contract.

Demonstrating Excellence

And here we get into the real art of winning contracts: for everything you write, or at least for the critical sections, you need to provide clear demonstrations of why you’re better than the other guy. These demonstrations need to be tailored to the particular agency or department the contract will be supporting.

Note that past contracts for all agencies are publicly available, unless they are classified, and the federal government publishes vast reams of data through the General Services Administration (GSA) and the Office of Management and Budget (OMB) regarding past contracts. Do your homework. If you’re applying for a contract with an agency, figure out what they do. Then figure out what your contract is being asked to do. Research any key words or programs that pop out of the RFQ. Find the past contracts that supported these programs, if there were any. See if you can find copies of the winning contract proposals — they’re lying around more often than you might think.

Use this information to build a picture of what the agency is looking for. Not necessarily what they are asking for. You need to address what they are asking for explicitly in the contract to meet the mail; you need to try to give them what they’re looking for in demonstrations of excellence in order to win.

For example, if I am reviewing proposals for a cloud-based computer system, you should give me some indication that you are expert with cloud-based computing systems whether or not I ask for it. That’s what separates winning proposals from chaff; you provide the reviewer with something they didn’t know they wanted.

An easy-ish way to do this is to simply go very slightly above the expectations in each item that you pull from the SOW. If the government asks for 99% quality ratings, demonstrate that you can do 99.5%. If the government asks for 3 people, offer to throw in one more. These are the margins of profitability that we’re talking about, so you’ll have to tailor it to your company.

A quick note: incumbents usually win contract renewals. This is why. They are the best-positioned to know what an agency wants, not just what it is asking for. If you don’t have this type of insider knowledge, you may have to take a slight profitability hit in order to make your offer more appealing than an incumbent’s. Judge for yourself if it’s worth it to get a five or six year contract.

Demonstration Traps

There are three main traps to demonstrating excellence that are easy to fall into. These are:

• Offering more than you can give: This takes many forms, but it usually comes down to lowballing the bid. Contractors often bid very low to secure a contract, then ask for a contract modification once they have secured the job and demonstrated that they are not, in fact, capable of doing the work at that price. Federal reviewers are mostly wise to this trick, and will take a jaundiced eye to bids or other sweeteners that seem too good to be true.⁴
• Demonstrating the wrong kind of excellence: The trouble with trying to figure out what people want is that, when you miss, you can go off in completely the wrong direction. This is a serious risk if you aren’t the incumbent, and it’s why my advice is to demonstrate excellence by improving on the SOW, not by offering random services that the government didn’t ask for.
• Boasting: If you claim excellence but don’t actually demonstrate it, you come off looking like you’re just making empty boasts. Always substantiate claims or don’t bother making the claim

If you can avoid these three traps, you are in the home stretch for securing the contract. One last thing to worry about…

Managing Resumes

Many, many, many contract proposals founder on the rocks of failing to meet resume qualifications. The government is absolutely not kidding when they say they want specific degrees, professional certifications, security clearances, or work experience in exactly the way they ask for them. They are also absolutely not kidding when they list key positions. Make absolutely sure that the people you are proposing meet the minimum qualifications, and make sure you’re proposing enough people to cover the bases.

The good news is that if you can get past the gateway of meeting the marks for your resumes, you’re basically home free. No reviewer is going to check up on the resume history of your people, unless they’re feeling particularly masochistic. The Contracting Officer might, and it might come up once you actually win the contract (so don’t lie), but the evaluation reviewers generally won’t. And the opinion of the evaluation reviewers is generally the opinion that matters, so if you can get past them you can at least get your foot in the door.

I’m not going to bother with a separate trap section for resumes, because if you remember to meet the marks, then there’s only one trap left: proposing someone that the government doesn’t like to a key position. This comes up almost exclusively in incumbency situations. If you have someone on staff who screwed the pooch in a prior year of the contract, their name is likely mud with the proposal reviewers (because again, these are usually the same people who’ve run past contracts for the project). A contract renewal is an ideal opportunity to find other things for such bad-reputation individuals to do within (or external to) your company, and you should take advantage of that opportunity to freshen the air.

With All That, Do You Win?

Ok, so you’ve done everything I’ve suggested and turned in a contract proposal in a format the reviewers can easily navigate, with clearly substantiated points explaining why your company is awesome, demonstrating excellence in your ability to meet the terms of the contract, with great resumes of great people. Do you win?

Maybe. Maybe not. But you sure as hell don’t lose as often.

It’s a numbers game, folks. For some contracts, the fix will already be in. I know that’s illegal, but it happens all the time. If a review team really wants one company to win the bidding, that company is going to win the bidding (and vice versa for losing). C’est la vie. For other contracts, your company just won’t be the best. For a lot of other contracts, it’ll come down to intangible factors as review teams try to hash out three or four equally valid proposals, and that’s just a dice toss.

The key point is simply this: if you’re not committing unforced errors, you win more often. You’re still going to lose sometimes. But your average will go up. And the kicker is that most of your competition will be busy shooting themselves in the foot. I can personally attest that in most proposal reviews, a clear winner rises from the pack almost immediately, and they are the company that follows the points I’ve laid out here.

One last point before I go — whatever you do, don’t half-ass it. Whole-ass it. A half-assed proposal wastes my time and costs your company money. If you aren’t prepared to devote the time to write a good proposal, don’t bother; you won’t win. Save your energy for the next one.

And with that, good luck. It’s hard surviving in the modern world, and it can be very hard surviving as a contracting company in the federal workspace, but this is how you do it.

If you liked this article, check out the Modern Survival Guide, Volume I, and my current work on Volume II! It’s an utterly random assortment of things I think people ought to know; there’s something in there for everyone.

¹This is based on 2018 numbers, so that figure is probably higher now. If we estimate that the average workforce in the US is around 156 million people, that means around 2% of the workforce is on contract with the federal government. There are tons more working for the states. And because the government purchases contracts, not headcounts, and is in fact legally obligated in some cases to avoid counting heads, we don’t know exactly how many contractors there are. Neat, huh?

²Unless the evaluation form is quantitively-based, in which case tailor your proposal directly against the SOW. No one wants to read through 156 sections tied to a quant evaluation methodology. Unless you’re going for a Dept. of Defense contract, because their procurement group are masochists of the highest order, and they might want that.

³I have personally blasted contract proposals because the company fucked up the introduction by claiming work I knew they didn’t do. If I can’t trust you to tell me what your work experience is, I can’t trust you for anything, and I don’t hire people if I don’t trust them. You can have the best proposal in the world and still get it thrown out because your proposal writer misstated the company’s accomplishments. Even if it’s a mistake, it’s still sloppy, and the government really hates sloppy contractors; they’re doing all our work, and we want it done correctly.

⁴I can’t name names, but I did once endure a contract protest based on this issue. The offeror bid a stupidly low price, which we knew indicated that they would either take a loss or underpay their people. Neither are good options; the first option indicates that they would seek a modification at some point (otherwise they wouldn’t make money), which is an annoying and costly process; whereas the second indicates that their people would jump ship at the first sign of a better offer, and we’d lose the experienced personnel. We ended up fighting off their protest based partially on median wage statistics for their labor categories, demonstrating that they were planning to underpay their people and that this would constitute a risk to their performance. Strange but true.