How to win proposals by making fewer mistakes

When every company intending to bid is struggling to prepare their proposal, then 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.

It takes both offense and defense to win

Putting effort into writing a great proposal is like playing offense. Putting effort into turning around a problem proposal is like defense. You need both a good offense and a good defense to win the championship.

I’ve seen many more proposals that were a mess than I have proposals that went smoothly. This has remained true at the precious few companies I've known who were great at proposal development. Herding cats against a deadline through problematical RFPs with reliable pre-RFP preparation and a mixed bag of experience in your writers is simply challenging.

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. You will be appalled at the number that were submitted after detailed processes, multiple reviews, and so many eyeballs looking for them. Every proposal is subject to Maslow's Hierarchy and the time available rarely lets us reach the pinnacle. 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. In addition to striving for perfection, a case can be made for striving to be able to turn imperfect into winning.

Perfection is not possible when trade-offs are required

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. During a proposal we make dozens if not hundreds of decisions regarding strategies to take, what the best approach to something is, which way to word or present things. How to make most of those decision is less than clear and usually made with less information than we'd like to have. All decisions like these require balancing risks. Perfection is not possible. However, improving your ability to balance risk is possible. 

Maybe, just maybe, instead of submitting a proposal that is as perfect as you can make it, you should improve your defense and 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.

Relying on your competitors to fail isn't the best win strategy, but the other team will make mistakes and you want to be in position to take advantage of them. If you also bring a good offense, your win strategies will not be weak. Since you'll never achieve a 100% win rate, the best win rate will come from combining a solid offense with an improved defense. When perfection is not possible go for the best at imperfect trade-offs and risky strategies. This is how you achieve the best win rate. 

Four mostly counterintuitive tips that can make a big difference

Okay. I get it. You aspire to not 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 try 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, less formal 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 sometimes it's better to sacrifice proofreading to allow 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, creating multiple unknown chances of losing. 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.”

Being imperfect is better than being a proposal hero

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. I'd rather work on proposals with professionals than with heroes.

Be the tortoise instead of the hare.

Or better yet, build a process that is reliable instead of heroic, that recovers from problems, that tolerates imperfection when it doesn't impact your win probability in a meaningful way, and best of all steadily cranks out proposals that are better than those of your similarly struggling competitors.