How to win proposals by making fewer mistakes

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. It may be counterintuitive, but in addition to giving your attention to implementing best practices, maybe 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. And even companies that produce good proposals often struggle doing it. A good way to hurt yourself is to review a proposal that you thought was one of your best, after you have 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. We all aspire to be perfect, even though none of us really are. And that's a good thing.

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. Figuring out what to offer 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 can even be tolerated. 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 and made the mistakes you avoided.

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 in real time instead of putting it off as some kind of "milestone" 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. The more you do to have clear expectations, the more you can prevent expectation failure. And allowing expectations to be rejected will enable you to find out more quickly than waiting for a deadline to be missed.
3. Aim lower. Simplify. Go for simple elegance instead of ornate. Make it easy to produce and require fewer people. Aim for preparing proposals that are reliably 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 relying solely on offense. Maximize your score by hitting what you aim for instead of overreaching. 
4. Make sacrifices for the greater good. We all want a proposal without typos. But maybe you should sacrifice proofreading to give more time to get your bid strategies right. If you don't have time for both but you can't make the sacrifice, the result could be everything falling apart during final production. 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.”

Managing your mistakes is about reliability and managing risk. Inflexibly attempting to eliminating all mistakes can actually increase risk. And increasing 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 reliable instead of heroic, and steadily crank out proposals that are better than those of your similarly struggling competitors.