11 ways to ensure everyone ends up hating proposals

Which ones are you doing right now?

Some companies prepare their proposals like they are trying to ensure people are miserable. Some of them even take it as a point of pride that everyone hates working on proposals. If you make proposals easier, there will be less glory at the finish line. So maybe we’ve got it all wrong and need to avoid all that process-stuff. Instead let’s embrace making sure that everyone has a bad proposal experience. Here’s how:

See also:
Proposal Management
  1. Hand them an outline and tell them to start writing. This makes it almost a certainty that they will spend all of their time up until the deadline writing and rewriting while people grow increasingly unhappy and the pressure builds, until they finally submit the proposal that no one is really happy with. If it gets really bad, that’s when the blame games will start. So just let people start writing the proposal with just a blank sheet of paper, a heading, and a copy of the RFP. Don’t do this, even when they are begging to get started on the writing. One of the reasons we recommend Proposal Content Planning is that it scales so that you can manage the time available, but still add significant value even if you can only spare a minimal amount of time for planning before writing. Just a few instructions per section can make a difference!
  2. Don’t tell your proposal writers what the reviewers expect to see until the review. Reviews should be routine exercises that find zero defects but make some helpful suggestions about presentation. If this is not the case, you’ve done something wrong in how you set up the review, and not just in how you wrote the proposal. The proposal writers should know exactly what the reviewers will be looking for. And it shouldn’t be in vague terms like “a compliant solution with a compelling presentation.” How do writers objectively self-assess what’s compelling? Both the writers and reviewers should be working from the same set of quality criteria that works like a rubric. If kids in school can have rubrics, why not people working on proposals? The reason we recommend Proposal Quality Validation is because it provides them.
  3. Leave ambiguity regarding who is responsible for doing what and making which decisions. One of the biggest things that a proposal team can’t decide for itself is who is responsible for what. Who decides when to change the approach? Who decides which strategies are acceptable? Who decides how to word the theme statements? There are dozens of issues like these. The Proposal Manager is rarely the highest ranking person working on the proposal. As long as people remain cooperative, it’s all good. But when there are conflicts, it can be very destructive if people don’t have a way to get quick resolution. Power struggles, territories, and the ensuing passive/aggressiveness will ensure that everyone has a bad experience.
  4. Figure out what to propose by writing about it. What are your approaches? What should you offer? Writing narratives about them is the worst way to decide. It means you don’t validate your solution until you have a draft. And it means the only way to consider alternatives is to write draft after draft. Until you run out of time in a proposal death spiral. Proposal writing in search of an acceptable solution usually ends with a terrible deadline crunch, a proposal with a low probability of winning, and a group of people who hate working on proposals. This is why we recommend separating figuring out what to write from writing about it.
  5. Start writing before you can explain how you will win the proposal. If you can’t articulate how you are going to win, then you don’t know how you are going to win. You’re hoping you’ll figure that out through the act of writing. And that ensures endless rewriting cycles that almost never pay off. Don’t try to think by writing. You need this as input at the start of proposal writing so you know how to position things, can make your win strategies the point of every paragraph, and can write a narrative that substantiates the reasons why you should win.
  6. Figure out what to write by starting from a previous proposal. This is a different proposal sin. When instead of preparing a Proposal Content Plan and what you want to offer you try to take a shortcut by recycling a previous proposal, what you really get is a proposal written using terminology that doesn’t match the new RFP, points of emphasis that don’t match the new evaluation criteria, and a context that reflects the wrong customer concerns. People fall into this trap because they don’t realize that similar is not the same, and turning a similar narrative into what you need takes longer than writing something designed to match in the first place. You can take inspiration from boilerplate, but you shouldn’t use it as the starting point for writing. That is why we prefer using Proposal Recipes over reusing proposal text.
  7. Change the outline after the writing starts. One of the most disruptive things you can do to a proposal is change the outline after writing has started. You might not be able to properly fix the narrative because it was based on the previous organization and have to start over. Except that rarely happens and instead people end up submitting a patchwork proposal. This is why we recommend validating the outline before writing starts.
  8. Ignore the proposal until the end and then change everything to save it. Why do so many bad proposal experiences seem to involve a know-it-all who can’t be bothered to participate in the proposal effort until the last minute, when they declare it’s all wrong and needs them to save it? Give me a proposal professional over a last minute hero any day.
  9. Make supporting proposals obligatory instead of part of growth. Growth is the source of all opportunity in a company. Growth is both personal and corporate. Growth is the reason why people should want to work on proposals. People get to work on proposals. They shouldn’t have to work on proposals. Unless you're trying to create an environment based on compulsive drudgery. 
  10. Move the goalposts. When you ask people to do something one way, you should forgive them if they think they’re done once they achieve that. If you ask them to do it again, but differently, you’ll probably feel some resistance start to kick in. Do that another time or two and you’ll probably see willing partners turn into people who are annoyed. 
  11. Ignore their needs. They know what you need. You’ve assigned it to them. But what do they need? What do they need to remove their distractions and resolve their challenges? What do they need to be comfortable? What do they need to not feel overwhelmed? What do they need to understand it all? What do they need to have a great proposal experience?

Access to premium content items is limited to PropLIBRARY Subscribers

A subscription to PropLIBRARY unlocks hundreds of premium content items including recipes, forms, checklists, and more to make it easy to turn our recommendations into winning proposals. Subscribers can also use MustWin Now, our online proposal content planning tool.


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.

Proposal Help Desk
Contact us for assistance
In addition to PropLIBRARY's online resources, we also provide full-service consulting for when you're ready to engage one of our experts.

It all starts with a conversation. You can contact us by clicking the button to send us a message, or by calling 1-800-848-1563.