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What is the worst sin in proposal writing?

It reduces quality in every step of the proposal

I’ll give you three hints:

  1. It’s the most frequent cause of the proposal death spiral, that cycle of endless rewrites that are never good enough and only end because there’s a deadline, resulting in delivering the proposal you have instead of the proposal you wanted to submit. Usually typified by trying to fit in one re-write too many and having a train wreck at the end where errors are likely to be introduced, but no time is left for quality assurance.
  2. It’s a major reason why the proposal reviews at most companies are inconsistently effective at best and often not worth the effort.
  3. While the intent might be to do things faster, it makes proposal writing take longer and cost more. By trying to make things easy, it ends up taking a lot more effort.

The worst sin in proposal writing is the phrase “I’ll know it when I see it.

“I’ll know it when I see it” means that you should just start writing so someone can tell you that it’s not good enough and then write some more.

The worst since in proposal writing is worse than it sounds

“I’ll know it when I see it” is the short form of the phrase. The part that is usually left unspoken is “I don’t know what I want, but I’ll know it when I see it.” Letting the words “I’ll know it when I see it” come out of your mouth is like admitting your ignorance in public. You should avoid doing that. The unspoken part means "I don't know how to win, but I want you to do it and I'll be the judge of whether you did it right." Whether it’s spoken or not, the problem is that you should never start writing the narrative part of your proposal if you don’t know what you want it to be. 

“I’ll know it when I see it” goes against every quality methodology ever created. It not only fails to define proposal quality, it’s anti-quality. “I’ll know it when I see it” is what someone says when they think they don’t have enough time for quality but think that if you try hard enough you will somehow achieve it anyway. Ignoring every best practice and quality methodology ever created is not a recommended way to achieve something important to your organization. Let alone to do it consistently.

The worst sin in proposal writing is usually followed by a rush to starting writing the proposal because the writers know they only have a limited amount of time before the deadline and know they will need every single minute so they can do more drafts until they figure it out. It is an approach based on fear instead of intent. It results in a final production ruled by panic instead of one that puts polish on top of confidence.

Why "I'll know it when I see it" fails

You will not discover what you want it to be when it somehow appears in front of you. That’s like waiting for monkeys at a keyboard to write a Shakespearean tragedy (although it does create a tragedy of a different kind). Here’s why:

See also:
Proposal Quality Validation
  • The writers don’t know what you are looking for, so they will not be aiming for the right target.
  • The reviewers do not know what they are looking for so they will misdirect (often contradicting each other in the process).
  • The second draft will have no better direction than the first, often resulting in people saying “it was better the first time.” But the truth is nobody knows what better is, let alone best. That is no way to reliably beat all of the competition and come out on top.
  • This makes quality defined by opinion and in a political hierarchy that makes quality defined by whoever has the most authority. 
  • The re-writes will only stop when you run out of time, resulting in submitting the proposal you have at that point instead of the proposal you wanted it to be.
  • You’ll try to fit one too many re-write cycles in, resulting in a train wreck at the end of the proposal. If you think it’s normal for proposals to have a train wreck at the end then hopefully this article will lead you to think twice about that.

You should not attempt to engineer your solution by writing a narrative about it. You should not attempt to figure out what ingredients should go in your proposal by writing until you’ve found them all. You should not engineer your solution or offering by writing about it. You should not attempt to discover what it will take to win by waiting until the proposal is written, reading it to discover the strategies are wrong, and then re-writing and re-reviewing until you trip over what the strategies should be.

The problem is that narratives are a bad way to collect, identify, account for, discover, and track things. Break and fix almost always takes more effort than doing something right the first time. This is particularly true with narrative text. Narrative text is messy. It’s full of connections and references, and it’s hard to parse. Ripping apart narrative and putting it back together after changes takes a lot of effort. People try to minimize that effort by making as few changes as possible, resulting in the minimum improvement instead of what it really should be. It will take longer to break and fix narrative than it will to think it through before you start writing.

You are much better off identifying the ingredients that should go in your proposal and making sure you know how to articulate what it will take to win before you start writing narrative text. That way, your revisions focus on improving your wording and not on discovering what your strategies should be. Changing strategies by re-writing narrative text is what leads to the proposal death spiral.

“I’ll know it when I see it” leads people to jump into writing before they are ready. It also leads people to bid things they shouldn’t, because they can’t show the gap between what they know and what they should know when the only way they have to discover it is by writing about it. The worst sin in proposal writing leads to arbitrary reviews instead of reviews that compare the proposal to what it will take to win.

Let’s see… Not knowing you’re bidding the wrong things until you write about them, writing before you know what to write, re-writing until the deadline and submitting what you have, and not defining proposal quality. Does anybody think this is how you should improve your win rate? The people who do this repeatedly do it because they don’t know any other way to do it, which brings us back to the part about it being driven by ignorance.

Go and sin no more

Intentionally going into a proposal without thinking things through and expecting to rely on an infinite number of re-writing cycles to save you before the deadline is no way to achieve proposal quality. Expecting the reviews to somehow trip over what it will take to win without defining the criteria that the reviews should use to define quality is a major source of proposal disaster.

Start by defining proposal quality. We define it as what it will take to win. First we articulate it, then we review how we’ve defined what it will take to win to make sure it’s what we want to build the proposal around, and then we turn it into quality criteria. We use the same criteria to drive the writing that we use for the draft reviews. We do not surprise the writers with arbitrary reviews. We review the proposal to make sure that what got written reflects what we agreed is what it will take to win. If you think about it, this does not add any effort to what you need to do anyway.

Watch out for the second worst sin in proposal writing

What it will do is make a fearful person nervous. Before someone says or thinks “I’ll know it when I see it,” they often first ask why they are doing all this thinking when “they could be writing.” They are not afraid that they’ll run out of time to write the proposal. They are afraid that they’ll run out of time to re-write the proposal as many times as they think they’ll need to in order to discover something good enough to escape blame. 

The worst sin in proposal writing is compounded by leading to the second worst sin. That is skipping figuring out what you are going to write because it "takes too much time" and wondering why we are doing this planning when "we could be writing." All that planning is really just figuring out how to make what you are going to write add up to what it will take to win before you start writing.

The worst sin in proposal writing is a thought crime

Carefully watch any proposal produced anywhere. More time is spent thinking about it than writing it. The difference is whether that thinking is circular or whether it is productive. All thinking is helped by inspiration. Seeking inspiration by doing without thinking and expecting it to get better with repetition is folly. So seek inspiration without creating narrative. Think until you’ve got valid strategies and everyone you’re working with agrees that they reflect what it will take to win. Then write with confidence.

If you throw out scary terms like “process,” “quality,” and “validation,” then all you really need to do is focus on identifying the ingredients and being able to articulate what it will take to win before you start writing narrative. How you go about doing that, whether you use a “methodology” or the back of an envelope, matters less than that it gets done some way, somehow. There is no way to successfully write proposals that are based on what it takes to win and include all the ingredients they should unless you identify them before you start writing. Never handicap yourself by skipping that, jumping straight into writing, and saying (or even thinking) “I’ll know it when I see it.”


Carl Dickson

Carl is the Founder and President of CapturePlanning.com and PropLIBRARY

Carl is an expert at winning in writing. The materials he has published have helped millions of people develop business and write better proposals. Carl is also a prolific author, frequent speaker, trainer, and consultant and can be reached at carl.dickson@captureplanning.com. To find out more about him, you can also connect with Carl on LinkedIn.

Click here to learn how to engage Carl as a consultant.

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