Winning by making fewer mistakes

and recovering better from the ones you do make

If every company intending to bid is struggling to prepare their proposal, then perhaps the one who does the best job of recovering from their mistakes is the one who is most likely to win. Maybe, just maybe, in addition to giving your attention to implementing best practices, you should give some attention to getting better at submitting imperfect proposals.

I’ve seen many more proposals that were a mess than I have proposals that went smoothly. A good way to hurt yourself is to review a proposal that you thought was one of your best after you submitted it, and start counting all the defects. We’ve never seen a proposal, including the ones we’ve worked on ourselves, check every box for how we define being a great proposal.

All proposals, including the great ones, involved trade-offs, risks, and compromises. Facilitating trade-offs, taking risks, and expediting compromises better than your competitors is just as important to winning as aspiring to best practices.

Maybe, just maybe, instead of submitting a proposal that is as perfect as you can make it, you should simply aim for a proposal that doesn’t make critical mistakes like:

  1. Compliance failures that get you thrown out
  2. Outlines that change after the writing has started
  3. Figuring out your bid strategies and the points you want to make after the writing has started
  4. Designing your offering by writing about it

These are highly disruptive mistakes that can be impossible to recover from. Other mistakes and defects are easier to recover from or even tolerate. If you avoid these mistakes, there’s a much better chance your team will say enough good things to outscore a competitor who was also struggling to complete their proposal.

Four mostly counterintuitive tips that can make a big difference

Okay. I get it. You’re not going to have any failures on your proposals. Everyone will fulfill your expectations. And you will aim high and always hit your target. In my experience, it doesn’t play out that way. And insanity is repeating the same mistakes over and over expecting different results. Even though it may be counterintuitive, you might achieve more success if you tried doing things differently:

  1. Fail quickly. If you wait for a major review to discover and fix your mistakes, your chances of recovering are less than those of a competitor who did smaller reviews more frequently. Consider validating decisions as they are made instead of waiting for the Powers That Be to see the document. Design your process around validating things right away instead of putting it off in the name of a “quality review” that comes too late to do any good.
  2. Manage expectations. The sooner you know that your expectations won’t be met, the sooner you can figure out how to work around them.
  3. Aim lower. Simplify. Go for simple elegance instead of ornate. Make it easy to produce and require fewer people. Aim for reliably preparing proposals that are good instead of heroically failing at producing great ones. It’s hard to look like an overachieving employee full of esprit de corps when you’re pulling your punches, but the odds sometimes favor a defensive game instead of exclusively relying on offense. Maximize your score by hitting what you aim for instead of overreaching. 
  4. Make sacrifices for the greater good. Skip things, like proofreading. Which is more important, getting the bid strategies right or proofreading? If you answer both, you might be the reason why final production falls apart. It’s better to ship an intentionally imperfect proposal than a broken one. A wise co-worker of mine used to say, “Better is the enemy of good enough.”

It’s about reliability and managing risk. Maximizing risk is not a good strategy for maximizing quality. Heroically challenging bad odds is a way to mostly lose. That occasional heroic win won’t make up for the lost revenue.

Be the tortoise instead of the hare.

Or better yet, build a process that is resilient instead of heroic, and steadily crank out proposals that are better than those of your similarly struggling competitors.

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 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 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.