- Frank OBrien

In today’s and next week’s memos, we turn our attention to a critical stage in the creative process – the rewriting and editing that come between your message’s first draft and its final version.

Too often, nonprofits fail to recognize how integral these steps are to creating truly persuasive communications. We can lapse into seeing them as just the last hurdles to overcome before getting an approved message out in line with the production schedule.

That’s a big mistake. So, let’s examine how to seize opportunities and avoid barriers on the road from first draft to final product. This is the first memo in a two-part series.

Today we’ll examine the most effective steps a writer can take in creating a strong message for others to review. Next week we’ll dig into the review, editing, and approval process.

The First Draft: just a starting point

For the moment, let’s jump past research, creative briefs, and all the other vital steps that precede a copywriter sitting down to create a first draft. Some writers are crystal clear about the first draft being only the beginning.

They just pour a lot of thoughts and ideas out on the page to be shaped later. Jordan Poole has a wonderful, even poetic description of this process. “When I’m writing a first draft, I’m constantly reminding myself that I’m simply shoveling sand into a box so that later I can build castles.”

Others, myself included, tend to take it step by step, not moving on to the next paragraph in our draft until comfortable the current one is in good shape. Either way, we all arrive at first drafts best thought of as a starting place.

Rewriting: “where the game is won or lost”

One of the worst mistakes we can make in the pursuit of persuasive messages is to underestimate the importance of rewriting. As writers, it’s only natural that we get emotionally invested in what we create. But we have to resist falling in love with our first draft.

A rigorous approach to rewriting leads to a stronger, more compelling draft to submit for others to edit, review, and ultimately approve. And conversely, just tweaking or “polishing up” the first draft almost always leads to a less compelling message.

Put it this way. You don’t have to buy into Hemingway’s famous “All first drafts are shit” pronouncement. But you do need to heed the wisdom of William Zinsser, author of the classic On Writing Well:

“Rewriting is the essence of writing well: it’s where the game is won or lost.”

Here are 10 tips on how to make your rewriting as effective and productive as possible.

Don’t confuse rewriting with rewording: Rewriting is about thinking through the pace, flow, clarity, and emotional rhythm of your writing. It’s not just about whether you’ve chosen the right words or turns of phrase.

Grab attention right from the start. Test whether your opening attracts attention and eliminate weak warm-up language.

Focus on your audience: Ask yourself if your draft reflects what your group wants to say or what your audience needs to hear.

Put every paragraph to the “so what” test. If it doesn’t add energy, advance the narrative, or drive emotion, what is it doing there?

Read it out loud: That’s still the best way to expose language that doesn’t work, tangents that break your rhythm and other flaws in your first draft.

Avoid jargon and policy speak: Make sure your draft doesn’t lapse into jargon and internal policy speak instead of everyday language that your audience can relate to.

Search out and remove mumbling: Find, fix or eliminate passages in your draft that lack energy and clarity.

Rewrite for structure: Make sure each paragraph flows naturally and convincingly from the one it follows. Don’t let your narrative take confusing detours.

Make sure shifts in tone are intentional: Well-planned shifts in tone can focus your audience’s attention. Random ones can confuse and distract.
Write. Rest. Revise. Stop: The classic advice to take a break before trying to revise your first draft is sound. But remember there is a point where revising too persistently can squeeze the life out of your message.

AI: where it fits in the process

One of the most fascinating (and sometimes fraught) topics in non-profit communications is finding the right role for AI. It’s a topic I will address more fully in a series of future posts.

But in 2026, no conversation about writing, rewriting, and editing our messages is complete without discussing where AI fits in. So, let’s dig in a bit on that front.

Here’s my take in brief. Don’t use AI to create for you. Use it as a junior editor to help evaluate your copy. And don’t use AI to think for you. Use it as a way to stress test your thinking. Here’s how AI influencer Andrew Bolis puts it, “AI shines when it amplifies human potential not when it tries to replace it.”

Given this perspective, I never use AI to create a first draft. That’s for three basic reasons:

I love to write and AI is best deployed to take things you consider drudgery off your hands, not to steal the ones that bring you joy.

If you forfeit writing, you forfeit thinking. It’s writing that forces you to sharpen your ideas, recognize and resolve things you haven’t quite worked out, and apply your lived experiences to the topic at hand.

As copywriter Vikki Ross observes “AI can generate standard stuff, but it can’t create standout stuff – stuff that’s going to really mean something to someone.”

If a nonprofit communicator asks an LLM to start the ball rolling on a serious piece of writing, that draft will almost certainly be conventional — built on common patterns, familiar framings, and safe, middle-of-the-road language.

That’s not an accident. It’s how LLMs work: they generate text based on statistical patterns drawn from massive amounts of training data, not from genuine understanding or original thought.

The AI first result may sound polished and competent, but it won’t reflect your organization’s unique voice, hard-won insights, or lived experience.

But wait, I’m not saying that AI has no role in
our creative work. Quite to the contrary, I think
it has a really helpful one that comes shining
through when we use AI to help test, evaluate,
and improve human-led creative work.

AI can be quite useful as one way to execute many of the rewriting tips identified above from weeding out jargon to identifying mumbling to checking structure.

And here are just a couple of the ways I use AI to help test and refine my own first drafts:

AI as Devil’s Advocate: This is one of my favorites. As mentioned, rewriting isn’t just about rewording. You can considerably improve your first draft by prompting an AI tool like Claude, Gemini or ChatGPT to test your assumptions, point out flaws, and expose counter arguments.
Search for New Arguments: Prompt your tool to consider your draft and identify ways to strengthen the arguments you’re making by adding new information or perspectives.

As promised, I will have much more to say about the role of AI in the creative process in upcoming posts. But I didn’t want to discuss the rewriting process without acknowledging how helpful AI can be if properly positioned.

Hopefully, this memo has convinced or reminded you how essential it is to give rewriting proper weight and attention in your creative process. In this Part One, I’ve focused on the most critical steps a copywriter can take to strengthen a message before submitting it to those responsible for reviewing, editing, and approving it.

Next week in Part Two, we’ll turn to those interactions as your message moves from first draft to final product.