Writing Authentically in the Age of AI
Four tactics to help amplify the humanity in your writing, in an increasingly AI-oriented world. Plus, a personal quest from astute feedback to Cher’s autotune.
Hi, it’s Tom—
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So if there’s a thorny challenge you’d like help working through together, sign up now. As of writing, I have 3 slots left. All next Thursday.
“You sound like a robot”
I remember this feedback vividly. It was 2016. I was sat in BuzzFeed’s New York office. Long before failing Bluetooth headphones literally made me sound like a robot, and before AI was part of our everyday lives.
The feedback was expertly delivered by Cap and Sabrina, about a first draft of a post I’d written to share our design process with the world. It hit hard because it resonated so deeply. A blind spot immediately illuminated as my brain reached the end of the sentence.
As David’s excellent podcast has since taught me, business writing sits at the intersection of clarity & character. While the BuzzFeed post was clear, the lack of character made it a slog to read and sucked all the joy from the work that went into the project behind it. And ultimately, although I’d written them, the words on the page didn’t sound like me.
Perhaps this is the designerly tendency to hone an artefact to its simplest form? Or a fear of exposing my own vulnerabilities and distracting from the purity of the ideas I’m trying to communicate?
Either way, over time I’ve learned to push back on these instincts, building confidence in sharing my ideas in writing. Whether that’s in weekly team updates shared on Slack, the rallying call to action on a new project, or a challenging milestone the team is up against.
As AI becomes increasingly infused in our daily interactions, I’ve been reflecting on how it fits into my writing process—and how it impacts the way we communicate as design leaders. Our impact isn’t just measured by the work our teams ship, it’s shaped by how well we communicate our ideas, influence stakeholders, and rally teams around a vision. Writing is one of the highest-leverage tools for this. But as AI changes how we write, how do we ensure our words maintain clarity and character?
While clarity, and AI’s role in simplifying, reducing, and summarising is evident, what’s AI’s impact on character? Because averaging out the entirety of human thought ever published on the internet has a tendency to, well, remove character.
What is character? Here’s how I see it—
In the context of writing, character makes words feel human. And in a world that’s increasingly mediated through or written by AI, humanity is the unique strength we bring to the table. That’s how our best ideas land, how we build trust, and how we deeply connect with others.
So how might we use AI to enhance character in our writing? Rather than remove it? While nothing replaces the thinking process, I’ve found these four tactics increasingly useful at enhancing or unblocking my writing process.
1. AI as Autotune
Ben recently shared a neat analogy: writing with AI is like Nike releasing a new pair of trainers that make most people better runners. The thing is, now everyone runs the same speed, finishing at the same time. No one stands out. I like where this is heading, but there’s some nuance that I think suits a more musical analogy: Autotune.
Antares released autotune in 1997 and since then, most pop records include some amount of it. It’s not always obvious, or front and centre, but it’s a tool producers can inject at key places to improve the flow of a song.
Used sparingly, it can recover bum notes from otherwise great vocal takes. Highlighting artists at their best by lifting the weakest parts of their original recordings.
And yes, it can also be used overtly, throughout entire tracks as a feature, but there are few artists who are able to pull it off, so unless you’re Cher or T-Pain, this might not be the best move.
Takeaway: Where are the points in your drafts that you’re least confident, where targeted AI improvements could raise the floor, better showcasing your voice or perspective?
2. AI as Audience
A tip that’s helped me write with greater honesty and personality, is to imagine writing an email, to a specific person, answering a specific question they’ve asked me.
AI tools can help scale this. What are the characteristics of the people you’re writing for? What sorts of questions will they ask?
Whether it’s a custom GPT or part of your prompt, you can use AI to share writing drafts and ask questions from the perspective of your reader. Rather than automatically correcting it for you, this helps reveal opportunities for you to take action.
Here’s an example prompt:
You’re Head of Design at a growth-stage product company with a small but high-performing team, mostly made up of product designers. While you’re getting great feedback from the exec team, you lack confidence in your ability to scale yourself and design’s strategic impact across the organisation. You've been playing around with AI and are exploring ways to use it to level up you and your team’s visibility.
- How valuable do you find the following post on a scale of 1–10?
- If you had 30 seconds to read before your next meeting, what’s your top takeaway?
- What's one question you'd ask that this post didn't answer?
<copy and paste your writing>If you don’t have a specific audience in mind, AI can help brainstorm the kinds of questions different folks might ask. For instance, the commercially-oriented general manager who needs to see expected impact on core business metrics before considering anything else about a new product suggestion.
Takeaway: How can AI feedback help you address your audience more precisely, and build confidence that what you’re sharing will add value? Whether that’s for your team’s weekly meeting, internal stakeholders in Slack, or publicly in building your employer brand.
3. AI as Interviewer
A simple trick: talk it out.
Know roughly what you’d like to write about but struggle with where to start? Have AI interview you. Here’s an example prompt:
You're a podcast host who specialises in A, with an audience made up of folks like B & C. You've invited me on to talk about D. You'll ask me 5–10 specific questions, plus any follow up question based on my answers. Ask one question at a time and pause while you wait for a response.Take this up a level by using voice mode, but plain old text works too. The key is using specificity (and low stakes) to make it easy to get the ball rolling. And lean on the AI interviewer to take the session in a way that aligns with the direction your audience’s thoughts are likely to drift.
By the end you won’t have a full post ready to go, but you’ll have fleshed out a bunch of ideas, giving you a draft of nuggets to pull from.
A simpler form of this is transcribing a humble voice note. Most days after lunch I’ll take a short walk to collect my thoughts and make a plan for the afternoon. Sometimes this takes the form of outlining a piece of communication I need to write, whether a blog post, a follow up message or a proposal. This method can feel like a more natural starting point, especially when sitting in front of your laptop can feel like a distraction magnet.
Takeaway: When a blank screen doesn’t work, talk it out. Whether sat in front of your computer or outside, walking. Experiment with specific prompts to reach more authentic depths in your own thinking.
4. AI as Average
I think most people would agree that AI knows average-quality writing. But by asking it write for us, are we missing the bigger opportunity? Knowing average-quality writing is an invaluable tool at helping us understand where our writing is average-quality, and where we can inject humanity and character to bring our words to life.
Let’s return to our formula, and write another AI prompt:
Character = Personality + Perspective + Vulnerability (+ Taste)
You're an online design publication editor. Your most successful articles are determined by the human connection they build, not just the information they convey. Give the following piece a score out of ten and the following feedback:
- Personality: what facts or personality traits do you know about the author from this piece alone?
- Perspective: where does their insight or point of view differ from the general consensus on this topic?
- Vulnerability: aside from writing ability, where are this person's flaws that reveal their humanity?
<copy and paste your writing>You may have noticed the word ‘taste’ snuck in here. While it sits alongside these qualities, it’s perhaps the hardest thing for AI to replicate. As many have talked about, it’s increasingly becoming one of the most rare, valuable, and innately human qualities we bring in an AI-oriented world.
And it underpins all four of these tactics too. While I recommend giving these a whirl, at the end of the day whatever you write needs to feel natural to you. And while AI can open up valuable avenues to explore, it’s ultimately down to you to choose what you put your name to.
Takeaway: Flip generative AI’s mediocre writing knowledge into its superpower, by helping you see where to add more humanity in your writing.
In conclusion
Why am I writing a design leadership piece about writing? There’s an old meme—which I can’t seem to find—about the tools designers used at various stages of seniority throughout their careers; from production-oriented tasks (photoshop, illustrator, indesign) → strategy-oriented tasks (all the tools) → leadership-oriented tasks (powerpoint)
While the tools and way of working have changed massively since then, the core idea of the highest-value, highest-leverage impact often happening through communicating ideas, is as strong today as it’s ever been. So whether it’s a thoughtful Slack message to the whole company, a persuasive strategy one-pager in Notion, or you’re just looking to build stronger psychological safety with your team through sharing your full self, with vulnerability and empathy. AI is not necessarily the answer, but nor is it the enemy. And used well, it can a valuable tool in strengthening your ideas and enhancing how they land, in ways that feel authentic and true to you.
What are some AI writing tricks you’ve found useful to you and your team? Is there any feedback you’ve consistently been given about your own writing that you’ve used AI to help with? I’d love to hear your thoughts.