What’s your proposal writing ritual?

Ray Allen is one of the great NBA shooters. He is one of the surest bets from the free throw line. Every time he shoots a free throw, he practices his stroke before he gets the ball. Then he spins the ball in his hands, takes three dribbles, spins again, and shoots. He makes almost 90% of his free throw attempts. His free throw ritual was compelling enough that teammate and league MVP Lebron James adopted it.

Rituals provide a sense of calm and control. They help our automatic systems take over. The Harvard Business Review ran a great article about The Power of Rituals in Life, Death, and Business by Carmen Noel.

While Noel covers a lot of territory, I want to focus on the power of ritual in writing proposals.

This is near to my heart because of the transformation I made in proposal writing. I used to:

  • Hate writing sales proposals
  • Get really nervous and scatter brained because I hated it and didn’t know what I was doing
  • Try to plow through it as an unfortunate  obstacle to the sale

Naturally, this was a vicious cycle. I know from talking to a lot of other sales people, entrepreneurs, and small business owners that my experience was hardly unique.


  • I actually enjoy writing proposals. For real.
  • I don’t get stressed out. I know what I need to do, what I’m likely to have ask further questions about, and what needs to happen next. (See How to Write a Sales Proposal in 6 Easy Steps.)
  • I view the proposal as a chance to lay out how I can help the customer (both for myself and for them). It’s not an end– the end is the success of the project. This takes a lot of the “sales” out of it, and let’s me focus on the solution, which is much better for my engineering mindset. Which makes me much more effective at sales.

Part of the change is the mindset, from “sales” to “helping.”

An equally important part is the ritual. When I get the “can you send me a proposal?”, I know if I’m close to ready. If I am, I ask when they want it, and when they want to follow up to discuss it.

If they don’t know both of those things, no point in getting worked up about it. I see a lot of people ruining their weeks writing proposals that they are not ready to write and their prospects are not ready to receive. Knowing when to say “not yet” saves a lot of trouble.

Next, I put on some headphones and play some classical music. I don’t like music with words when I’m writing prose.

Then I review my notes in Evernote, reorganizing to fit my proposal template.

Then I fill in the proposal template with the key sections of the notes. At this point, I don’t worry about word smithing, but I do want to make sure I get the customer’s words in there. If I ask the customer to translate my words, I put obstacles in the way. (See Proposal Writing Secrets: How to Use the Right Words.)

When I’m done with this, I go through and read the proposal out loud. (If I’m on an airplane or somewhere else I can’t actually talk, I try to talk silently– moving my lips without sound. Yes, this seems weird if you haven’t done it, but just reading your own words silently to yourself allows your brain to fill in too many gaps and correct too many mistakes.)

At this point, the proposal is complete, but not done. This is another point that causes a lot of stress. But it doesn’t have to be that way. The problem is that you will have unanswered questions, things that you didn’t know you didn’t know until you tried to put everything together. I used to try to guess. This caused a lot of stress.

Now, I know this is coming, so I note the questions, the same way I would if I was in a room discussing the proposal with the prospect. Depending on the number of questions and my relationship with the prospect, I either share the draft proposal with them or just say I’ve got a few questions. The prospect would rather deal with issues upfront than wade through a half-baked proposal and then deal with the issues.

When I get answers to the questions, I fill in the problematic pieces of the proposal, remove the draft label, and share it with the prospect. It’s fun.

Then, we have a follow up conversation. There are usually more questions, that the prospect didn’t consider. So we have another round. Again, no big deal.

Then, they sign (online, preferably), and I have a glass of scotch. That’s the end of the proposal ritual, and it’s on to the project.

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