Dealing with Proposal Losing Streaks

Wait Until Next Year

I’m a Chicago Cubs fan. As you might imagine, that makes for a vexing sports entertainment experience. However, rooting for the Cubs has taught me the value of optimism in the face of long-running challenges. “Anyone can have a bad century,” as one Cubs manager put it. That doesn’t mean I learned to like losing.

This past week, a proposal I helped a customer write won the bid. This was a moment of joy for the customer and a great relief to me. I’ve worked on a lot of proposals over the past 3-4 years. To the best of my recollection, I’ve lost nearly every single one, going back to 2012–the last time I can recall a confirmed win.

It isn’t personal, Sonny, it’s just business

Note the “I” there. That’s my first mistake: an understandable one, but a mistake nevertheless. A proposal has many contributors, from the technical subject matter experts to the people providing the cost figures to the graphic designers providing graphics. Still, it’s the writer/book boss/proposal manager who typically has responsibility for the final product. To not win a proposal means that the potential revenue from that opportunity won’t be coming in, so there’s ownership and pressure there.

Ownership and pressure are inevitable side effects of proposal writing. Winning isn’t inevitable, however; and you will lose a few. Or in my case several of them scattered over multiple customers and years.

The important lesson here, as noted in the Godfather quotation in the heading, is: don’t take it personally. That’s not to say you didn’t have a role in some of the losses, but that’s also overlooking the realities of requests for proposals (RFPs).

Some reasons why it might be your fault


Okay, let me get this part over with so I can move on to the more optimistic angles. There are, in fact, a few things that a proposal writer or manager can do to torpedo the success of a proposal. You’re just asking for trouble that way, like Charlie Brown repeatedly accepting Lucy’s challenge to hold the football for him. There are some things you should just learn not to do.

  • Turn it in late. No excuses: you’ve got to make the deadline. One proposal I worked on was submitted in parts. Three fourths of it was submitted before the deadline. The last part–the cost volume, not my area, I hasten to add–was still being worked on up to the last minute and then some. It was submitted some  seven minutes late. Proposal: rejected. X millions of dollars in potential revenue: gone. The government takes its deadlines seriously. You should, too.
  • Submit a proposal that is not compliant with the instructions. Aside from the obvious deadline, government solicitations especially will prescribe the specific order of a proposal–even the section headings–along with the page margins, fonts, and font sizes. There might be other reasons a proposal gets bounced, which I’ll get into in a moment, but noncompliance with the instructions is an easy way for a reviewer to get your proposal off their pile and reduce their workload. Read and follow the directions.
  • Misspell obvious, visible, GLARING things. These are items such as the name of the customer, the name of your company/product, words in the title. Sad but true: people judge you based on the quality of your spelling. Those are the same people picking on you for typing in Twitter-speak. They’re out there, and they’re not all proposal writers (like me, ahem). And the Spelling Judges will think, “If they can’t even spell X product correctly, how am I supposed to believe that they’ll do the work well?” Spell checking is important, but reading is also important. Remember the lesson of the Spell Checker Poem.
  • Get the technology wrong. Say a subject matter expert gives you an explanation of the XYZ Widget. You think you translate the technobabble into proper English but neglect (or run out of time) to get a technical review. Your work ends up in front of the technical reviewer, who takes one look at your prose and says, “These guys are full of BS” or “That violates the laws of physics” or, more likely, “These guys don’t know what they’re talking about.” Make sure your technical writeups are making sense.

Some reasons a proposal loss was most likely NOT your fault

Unless your company is writing a task order proposal under a sole-source contract, the odds are good that you’ve got to work against at least one other competitor. The other thing you have to consider is the customer(s) and whatever is going through their mind. Let’s look at the factors that are beyond your control.


  • The competition had the lowest bid. Your company might have the best left-handed widget in the industry, but ABC Company down the street, which is almost as good, is also half a million dollars cheaper. If price is the most important criteria (and quite often they’ll tell you that), your company is going to lose, plain and simple.
  • The competition had a better product/service. Sometimes a customer is looking for the best left-handed widget, and ABC Company down the street is famous for designing and building left-handed widgets because they invented them and have stayed on top of the game ever since then. Or maybe you ARE the ABC Company and the customer is looking for something new and radical rather than something that’s been around for fifty years.
  • The competition has what the customer is looking for right now. I’ve seen this problem in both government technology opportunities and nonprofit foundations.

    The U.S. Government’s Small Business Innovation Research (SBIR) opportunities and the NASA Innovative Advanced Concepts (NIAC) solicitations are annual, open invitations to businesses to submit bright ideas that could help solve a particular government problem. The RFPs frequently feature a range of topics or technology areas. Your company might have a bright idea for a right-handed widget that is just perfect to solve Problem Y. However, when the Source Selection Evaluation Board finishes going over all the proposals, they might decide that while your right-handed widget is quite clever, it doesn’t meet their needs because they’re really more focused on Problem Z this year, and the ABC Company has exactly what they want.

    In the nonprofit sector, foundations face similar constraints. They have particular types of organizations or projects in mind when they’re handing out grants. Sometimes other organizations just fit the objectives better.

Things you can do to improve your odds in the future

  • Ask for a debrief. This is pretty common practice in government contracting–contractors will request a one-on-one session or just an email or letter from the contracting officer for feedback on the proposal. This is often a good idea whether you’ve won or lost so you know your strengths and weaknesses. The loss discussion, while not fun, is absolutely vital for helping you and your company learn how to do better in the future. A win discussion is a good idea, less painful, is much simpler. In that case, you can ask the customer directly or send an email asking, “What were the key differentiators in accepting our bid?”
  • Up your game. Are you saying the same things in the same old ways? When was the last time you took a refresher course in proposal writing? If you don’t have the money or time to upgrade your skills, you can always go online and look for pointers. You are reading this blog, for example, aren’t you? So here are some freebie reminders to help you get back in the game:
    Tips for Improving Your Proposal Writing
    Getting to the Heart of a Matter in a Technical Proposal
    Marketing Language in Proposal Writing
    Proposal Survival Tips Revisited
    How to Decipher Government Solicitations
    Doing Effective Business Development Research in FedBizOpps
    Working in the Little Room
  • Get some help. Some proposals–especially the big-money, sink-or-swim proposals that the whole company is counting on to win–have the attention of upper management. Knowing the importance of the opportunity, they will assign additional help to ensure perfection: editorial, graphical, technical, etc. However, sometimes a proposal is NOT that important, but you feel could use the help anyway. Ask for it.
  • Improve your business intelligence ground game. You might or might not be part of the business development team that goes out and talks to customers, but you can encourage those who do talk to customers to get a better idea of what their current needs truly are so that future proposals are geared to meet those needs. Those discussions are easier if you already have a relationship with a customer, but there are other opportunities to reach potential customers, including conferences, where your business development team can have meaningful conversations that guide your future proposal efforts.
  • Shake it off, try again. Like I said, losing streaks can happen, but you can’t let it affect your confidence in your ability to do the work. You have written winning proposals, you will do so again. You have to believe that as a simple survival mechanism and for the good of your own mental health. Oh, yeah: and your paycheck.


Note: The Chicago Cubs have not won a World Series since Theodore Roosevelt was President of the United States. That didn’t stop me from cheering them on when they lost in the playoffs last year or all those many years that they haven’t even made the playoffs. Anyhow, they have been on top of their division for practically the entire 2016 season, and October is coming. Hope springs eternal.




About Bart Leahy

Freelance Technical Writer, Science Cheerleader Event & Membership Director, and an all-around nice guy. Here to help.
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4 Responses to Dealing with Proposal Losing Streaks

  1. Larry Kunz says:

    “It isn’t personal, Sonny, it’s just business.” How true. Except, at least in the private sector (which is where I’m accustomed to working), there’s a personal element along with the business element. Especially if bidders are allowed to present their proposals in person, your professional and your confident demeanor can help tilt things in your favor. Even if it’s just a written proposal, the quality of your writing can help you or hurt you — as you’ve often pointed out in the past.

    Does this personal element come into play in the government sector as well?

    All in all, thanks for a great post – one I’ll want to refer back to often. Go Cubs!

  2. Bart Leahy says:

    When I’ve seen it, the only time the personal side of things might affect an outcome–and there’s no way to prove it, of course–is if your customer has a rocky history with the customer. Of course the opposite is true, too: sometimes it appears as if RFPs or decision-making processes are set up so that the thumb goes down on the scale for one particular bidder. I say this because I’ve seen and heard things that lead me to believe it…note that I’m not naming names or situations. The bidding system is supposed to be objective, but just as job descriptions can be written with one person in mind, so too can solicitations be written with one company in mind.

  3. Bart Leahy says:

    On a related note, sometimes the solicitation is badly worded and full of rotten instructions:

  4. Lisa Kaspin-Powell says:

    The proposal writing article was a great help to me, and I thought I’d add another tip (because at one of my old jobs we were using some parts of old proposals as templates): make sure to have the right client name on the proposal!

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