6 Proposal Writing Skills to Improve in the Age of AI (With or Without ChatGPT)

Kyla Steeves, Content Marketing Manager at Loopio
Kyla Steeves

Have you used AI for proposal writing yet? While tools like ChatGPT can whip up a speedy first draft, only you can take a proposal from boilerplate to shortlist-worthy.

That’s because you have what generative AI lacks: the ability to captivate, convince, and connect with clients on a human level. This unique expertise will remain invaluable—if you keep your skills sharp. ✍️

Here are 6 proposal writing skills to improve in the age of AI:

Top Skills a Proposal Writer Needs to Excel Today

AI can be a helpful tool for proposal writers, but the true art of creating a winning proposal goes beyond automated text generation. The key to standing out in this digital age lies in 6 proposal writing skills:

1. Research Skills: Read Between the Lines of the RFP

One of the most important steps in proposal writing is reviewing the entire RFP and making a list of formatting requirements, submission guidelines, and key insights about the client. While ChatGPT can generate a summary in seconds, the real magic happens when you read between the lines.

  • What are the customer’s biggest pain points?
  • What do the key decision makers care about most?
  • Why is your solution the best choice—and where does your competition fall short?

Answering these questions upfront will help you personalize the proposal.

For example, you may identify that the client seems focused on ease of adoption because they don’t want to disrupt operations. In that case, you can emphasize training and support in your win themes.

“Use the ‘Find and Replace’ test. Can you replace your name with your competitor’s name and it still holds true? You’re lacking differentiators. Can you replace the client’s name with one of their competitor’s names? You need to do more research and relationship building.”
Ceri Mescall
Ceri Mescall
Work Winning Consultant

How do you improve your research skills as a proposal writer?

  • With ChatGPT

    Ask ChatGPT to analyze the RFP and generate a quick summary of what the customer seems focused on overall—based on the top features they’re looking for.

  • Without ChatGPT

    When reading the RFP, use a different colour marker to highlight each time the client mentions a different feature. This will give you a colour-coded view of what their biggest focus appears to be.

2. Collaboration Skills: Write Effectively With SMEs

Writing proposals is rarely a one-person feat. You usually have many subject matter experts (SMEs) who contribute answers to the RFP, which can create a “too many cooks in the kitchen” impression.

Despite being a product of many, it takes a skilled proposal writer to make the RFP response sound like it’s coming from one convincing voice. As Dragonfly Editorial explains, there are a few guidelines you can provide SMEs to help:

  1. Proposal messaging: Focus on what to say first. Make sure your SMEs are crystal clear on your win themes so they can channel that positioning in their responses.
  2. Brand voice guidelines: Next, focus on how to say it. Outline the appropriate tone you want to come across in your proposal by providing a clear description of how your voice should sound.
  3. Writing style: Determine the general style guide your organization should use (e.g. Associated Press Stylebook) and provide any in-house guidelines that might deviate from the standard.
  4. Level of detail: Give SMEs parameters for how long and in-depth their answers should be. You don’t want some sections to be over-the-top detailed while others are too surface-level.

How do you improve your collaboration skills as a proposal writer?

  • With ChatGPT

    Run the final proposal through ChatGPT and prompt the tool with brand voice guidelines like: make this proposal sound more confident and exclusive, positive and inspiring, or considerate and simple.

  • Without ChatGPT

    Become a brand voice ambassador and show SMEs what a good RFP answer looks like in the first pass. Alternatively, you can hop on a call with them, record their answers, and polish their phrasing yourself.

3. Critical Thinking Skills: Put Yourself in the Client’s Shoes

Having customer empathy is essential for writing proposals. Yet, it’s one of those proposal writer skills that takes lots of practice. That’s because it requires picturing what a client’s life will look like before (and after) they’ve implemented your solution—when you don’t have a crystal ball. 🔮

One method that can help proposal writers do this is harnessing the StoryBrand approach. Similar to crafting a strong brand message, it involves creating a story arch in your proposal writing, like so:

  1. Make your customer the main character: Put their needs and interests at the center of the proposal.
  2. Use their pain points as the antagonist: Empathize with their struggles and frame their problems as a villain they need to vanquish in order to accomplish their goals.
  3. Be the guide, not the hero: As StoryBrand founder Donald Miller writes, “You’re not Luke Skywalker. You’re Yoda.” When introducing your company, angle it as “We’re here to help you,” rather than “We’re here to save the day.”
  4. Give them a plan: Empower your prospect to take action. Yoda’s plan was to train Luke how to use the Force to defeat Darth Vader. For you, it might be a three-step system to bring in more leads.
  5. Provide a happy ending: Show your character the transformation that lies at the end of your plan by describing the benefits they can expect. How will their business (and lives) improve?

How do you improve your critical thinking skills as a proposal writer?

  • With ChatGPT

    Have ChatGPT change every sentence to start with “we” or “our” to “you” or “your.” This simple shift will put the focus back on your client, making your proposal writing sound more empathetic.

  • Without ChatGPT

    Practice passing every feature in your proposal through the So What? test. Always pause and ask yourself: what is the biggest benefit and why does it really matter to the client’s story?

4. Creativity Skills: Write Catchy Headings and Subheadings

Good proposal writers know that headings are important for the structure of a proposal because they act as signposts that help evaluators find information quickly. But great proposal writers know that headings can also be impactful statements that drive home your win themes.

What sounds more compelling? A vague heading such as Our Solution. Or a more descriptive heading, such as Stronger Security for Your Peace of Mind. The latter, of course.

So, take this header tip from copywriters the next time you edit a proposal. Only read the headers and ask yourself whether they each:

  • Communicate a key benefit or pain point?
  • Entice the evaluator to read more?
  • Capture the main points of the body text?

If your answer is “no” to all of the above, your headers could use some tweaking.

That said, some RFPs will have strict heading requirements. If that’s the case, put your creative energy into the first sentence of each paragraph instead—don’t bury the lede.

“If you use an app like ChatGPT, try playing with it to get inspiration on how to write your proposals better. Let it know the style you wish to apply (professional, friendly, simple, short), what information to add, and which benefits to emphasize. It will give you plenty of ideas.”
Susan Brosh
Susan Brosh
Proposal Manager
Datavail Canada

How do you improve your creativity skills as a proposal writer?

  • With ChatGPT

    ChatGPT is a great brainstorming tool. Paste a section of your proposal into ChatGPT and ask it to come up with 5 different headlines. Or, start with a basic headline and ask it to make it more powerful.

  • Without ChatGPT

    Focus on providing more details. Weave in stats and figures where you can. Make the heading actionable by starting with a verb. Or, add in power words to spark emotion.

5. Technical Writing Skills: Make Your Solution Easy to Understand

Like most proposal writers, you probably went into this profession because you have excellent written communication skills. However, what sets this job apart from other writing careers (like copywriting or journalism) is you must also be able to translate technical details into persuasive content.

That’s because your goal as a proposal writer is to inspire buy-in from the evaluator. And if they can’t grasp you’re solution, they’ll discard your proposal faster than you can say, “What I meant was…

To ensure your proposals are easy to understand, consider these three approaches:

  1. Remove unnecessary jargon: This is one of the most common mistakes in proposal writing . Unless your prospect is looking out for specific industry terms, use familiar language to describe your solution, spell out acronyms, or avoid jargon altogether.
  2. Simplify vocabulary and phrases: There’s no need to use the “fancy” version of a word to sound more professional—it confuses more than it sells. For example, instead of using the phrase “in light of the fact,” get straight to the point and say, “because.”
  3. Focus on impact over details: When explaining technical concepts, it’s often more effective to highlight the benefits rather than going into heavy detail about how every feature works. This helps the client see what makes your solution a worthwhile investment beyond your capabilities.

How do you improve this technical writing skill as a proposal writer?

  • With ChatGPT

    Turn ChatGPT into a ruthless editor. Ask the AI tool to do a clean sweep of your proposal by replacing technical jargon with laymen’s terms and trimming word count where necessary.

  • Without ChatGPT

    Always read your proposals out loud to force your brain to process each sentence. Soon enough, you’ll get better at catching clunky phrases, awkward rhythms, and filler words.

6. Time Management Skills: Meet Deadlines On Time, Every Time

RFPs usually have tight deadlines. If you miss it, that’s it. The evaluator won’t review your submission. That’s why it is crucial for proposal writers to have good time management skills.

But meeting deadlines doesn’t always come easily—especially when the strongest coffee can’t help you overcome writer’s block. Thankfully, there are a few time management tricks that can help you write high-quality proposals under a time crunch:

  1. Remove distractions: We’re looking at you: smart phones, Slack, and email. When it’s time to write, put your phone in another room, mute your notifications, and sign out of your email. You can check them once you’ve hit your writing goal.
  2. Block time for proposal writing: Parkinson’s Law says we fill the allotted time we give ourselves to complete a task. So, don’t give yourself more time than you really need. Instead, set strict, yet reasonable goals, like “Finish sections 1-5 before lunch” or “Complete first draft in X hours.”
  3. Eat the Frog: Coined by Mark Twain, the idea behind this concept is to set yourself up for success by getting the harder tasks over with first. For most proposal writers, this task is often the writing of the first draft. So, try to write first thing in the morning (or when you have the most energy).
  4. Choose progress over perfection: Perfectionism is a serious time waster. During the early stages of writing, do your best to let go of “perfect” and focus solely on getting words on the page. Once you get the bulk of your proposal written, you can refine until the deadline.


How do you improve your time management skills as a proposal writer?

  • With ChatGPT

    Skip the blank page altogether. Give your outline to ChatGPT and have the tool generate a first draft for you in seconds. With the extra time, you can customize the proposal for the client instead.

  • Without ChatGPT

    Learn how to be okay with a messy first draft. Instead of waffling over words, practice writing a proposal as fast as you can without breaking your flow. It’s quicker to improve your writing later than edit as you go.

Want to learn more about writing proposals? Learn how to create a repeatable RFP response template.

One More Piece of Advice for Proposal Writers❣️

As you set out to improve proposal writer skills, remember that mastering this craft goes beyond putting words on the page. Proposal writers who learn how to write a bid proposal that stands out will thrive. Especially if they can harness the power of GPT technology while maintaining their unique human abilities.

In the meantime, remember this…

“If there are more senior members on your proposal team, take a look at their final proposals and drafts so you can study their process and style. Join professional forums, read columns, and never hesitate to ask other members of your team for some additional training.”
Tanya Boutin
Content Manager, Client Communications
The Shortlist

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