Writing A Winning Proposal

Welcome Freelancers!

Because the Barefoot Consultants Team is traveling to the International Living conference in Portugal tonight… in place of our normal Tuesday night call we invite you to enjoy this new session on writing proposals with AI.

Top 5 Most Important Aspects of This Video (with Timestamps)

• AI-generated proposals on Upwork should be used as initial drafts and manually refined to reduce boastful language, excessive use of "I," and improve client-focused language.

• Winton highlights the importance of ending proposals with a clear and direct call-to-action question to encourage client responses.

• Simple changes like replacing "I" with "we" transform proposals into collaborative, persuasive messages, increasing the likelihood of winning bids.

• Winton emphasizes avoiding age discrimination by stating "20+ years of experience" rather than explicitly mentioning "40 years," which could create bias.

• True freelance branding relies on delivering quality work and building reputation, rather than flashy, superficial branding typical of YouTube influencers.

Here's a concise bullet-point summary of the transcript with approximate timestamps:

 (Approx. 0:00–53:40)

• 0:00–1:00 – Friendly opening chat about weather and locations (Orvieto and mid-Atlantic).

• 1:13–2:40 – Introduction to session topic: writing proposals with AI (specifically ChatGPT); it's helpful but not yet fully automatic.

• 3:00–6:30 – Explanation: AI can provide a solid draft, but human touch is essential to make it persuasive and client-focused.

• 6:30–8:30 – Real-life Upwork job example is introduced (email communication for a construction company).

• 8:30–10:30 – Importance of aligning the domain knowledge (construction background) with job choice.

• 10:30–12:20 – Discussion of the prompt used with ChatGPT to generate a proposal.

• 12:25–19:30 – Critique of ChatGPT’s output: overuse of “I,” assumed confidence, lack of persuasive tone, and awkward closings.

• 19:30–24:00 – Introduction of the 7-step proposal writing model and beginning of the rewrite process.

• 24:00–44:30 – Live walkthrough of revising the ChatGPT-generated proposal using client-focused language and improved formatting.

• 44:30–47:30 – Final edits include removing weak closings, adding a strong call to action, and ending with a compelling question ("Make sense?").

• 47:30–50:00 – Recap of copywriting techniques used; ChatGPT is a strong partner but needs human refinement.

• 50:00–53:40 – Closing thoughts on continual improvement, learning new tricks, and upcoming sessions with more end-to-end examples.

Best,

Winton & Bruce