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Reviewing Your Proposals Makes You a Better Closer

This week’s habit was all about one of the most essential documents in your business: the proposal. I focused on conducting an AI proposal review, and it reminded me that this simple check-in can improve how you communicate your services and close new clients.
What Worked Well
I’ve used ChatGPT to revise proposals for a while, but this week, I took the time to run both my WordPress and Squarespace proposals through it with fresh prompts. I used questions like:
- “Is this clear to someone unfamiliar with web design?”
- “Does this sound friendly and spartan in tone?”
- “How can I simplify the call to action?”
The result? Cleaner, more accurate proposals that better reflect my current services.
Challenges: Keeping My Voice
The biggest challenge was making sure that my updated proposals still reflected my voice. AI is helpful, but if you’re not careful, it can dilute your tone. One trick I use is writing out answers to key questions in my own words first—and then feeding that into the tool. This keeps the voice consistent.
A Surprising Benefit: Shorter Process Time
I’ve been meaning to template more of my proposals, and using ChatGPT helped me get closer to that goal. It sped up the editing process and provided me with reusable language blocks that I can apply repeatedly. The more I revise, the more streamlined my process becomes.
Tools & Resources That Helped
- Google Docs – My home base for creating and storing proposal drafts
- ChatGPT – For content refinement and clarity checks
- Proposal Worksheets – A Q&A doc I fill out before dropping anything into AI
Lessons Learned
Although I've refined my proposals over the years, there's always room for improvement. AI makes it easier to update language, catch areas of confusion, and test different approaches—mainly when you review your docs with a fresh perspective.
Moving Forward
I plan to review my proposals every six months and maintain a dedicated AI thread for edits. This will help me stay consistent and continue evolving my documents over time. I also update my templates more often instead of editing one-offs.
How You Can Implement This Habit
Download your current proposal (just the pitch, not the contract) and paste it into your AI tool of choice. Ask for feedback on clarity, tone, and persuasion. Then, tweak your content based on your current services, offerings, and style. Save an AI thread specifically for this habit, and plan to review your proposal again in six months. The more often you do it, the easier it becomes to keep things fresh.

about the author
Cami MacNamara is a web designer and owner of WebCami LLC, a Seattle-based agency since 2002. She created Web Designer Habits to help web designers build smarter systems, stay productive, and run a business that works for them.