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#158 Personality is Paramount
One Thing AI Can Never Replace

Welcome back to On the Fly.
Prof Mike:
As AI becomes more prevalent in the workplace, new concerns arise. Donât get me wrong - Iâm sure some people love it. All that monotonous minutiae that made you feel robotic, being outsourced to an actual robot so you can focus on more important things? Sign me up.
But thatâs not where companies seem to be drawing the line. Iâve heard from multiple people recently that their bosses are mandating using AI to respond to emails. Is this what we want? To automate our interactions with other human beings?
Like most other things, we seem to be divided here. Some are fine with it - a lot of workplace communication requires neither thought nor style, so Al summarizing an email and responding âReceipt Confirmedâ can save time and energy.
On the other hand, what happens when the line gets re-drawn again? When the emails arenât so simple? When AI makes mistakes (which they do often) resulting in serious miscommunication, or people stop reading them because of the repetitiveness (resulting in human mistakes), or everyone starts sounding the same and some of what made you stand out at work suddenly levels the playing field?
This last concern may sound selfish, but itâs legitimate, both for employees and employers. And thatâs what todayâs edition is all about: the importance of personality / originality in an AI-assisted workplace.
Letâs talk about it âŹď¸

I was reading an article from YourTango recently with the headline âWorkers Who Have This Deceptively Simply Habit Usually Get Promoted Faster,â doing some recon for my students. Most are business majors, so why not?
The article ended up being about remembering co-workersâ names (which is both a good communication tip and something thatâll be outsourced to Meta Glasses in the near future), but this paragraph really stood out to me:
Most people put more stock in their skills and experience when it comes to professional success, but as the job market becomes more cutthroat, personality is becoming a more desirable trait. Often labeled a soft skill, the ability to connect with co-workers and colleagues isn't just an added perk when it comes to strong candidates and employees anymore. It's a desired trait.
Thereâs a way to let your personality shine even when using AI to write (which Dan will go over below), but to me, this means your actual face-to-face conversation skills - whether in-person or via Zoom - are more crucial than ever.

So how can you make sure you stay you and make sure your personality shines? I have a few ideas:
Spend Less Time With Your LLM - In a recent group convo with some college friends, one sent a message to which three of us responded, Did AI write this? My friend assured us it hadnât but followed up with âProbably the result of using so much AI over the past year.â
The more you digest AIâs generic language (remember: itâs default isnât stylized language; itâs summarizing information), the more it will impact your communication style (written or verbal). So moderate your LLM usage, prioritize human interactions, and read other things to keep your language intake varied.Keep Telling Stories - Humans will always do this better. AI tries to fake it, but their stories lack that certain something. They may be technically polished, but theyâll never be as relatable or emotional as a well-told human narrative. Instead of making dry AI-styled arguments or presentations, use anecdotes or examples grounded in personal experience to both get your points across more effectively and connect on a human level to those around you.
Lean Into YOU - If youâre a great storyteller, keep telling; if youâre funny, let your humor shine; if youâre self-deprecating, by all meansâŚeven if itâs just certain phrases that are unique to you - the way you greet or say goodbye, the way you express excitement when hearing something surprising, etc. - think about what your bring to the conversation table and what others typically respond positively to and keep doing it.
This is where Iâll pass it off to Dan, because I think itâs a good transition: communication style is something worth thinking about. What is my style? How do I want my personality to come across? Itâs possible youâve never thought about it, that this is just who you are and how you speak naturally. Thatâs fine. But as AI rises around us, and we try to avoid the inevitable homogenization of language that will claim our peers, taking some time to reflect on it can make a big difference.


I would make a bet youâre accustomed to using LLMs like ChatGPT, Claude, Gemini, Copilot, etc. on a weekly, if not dare I say, daily basis đą
Whatever your usage, your LLM is being trained on what you ask it so it can deliver better results to you. More investment into the tool = better ROI for you.
Now, if youâre using LLMs to help you with typical asks around the house, with your travel plans, or even with issues with your car - thatâs all good and great. It helps you get to answers faster with detailed reasoning. But let me ask, do you need to showcase your personality when prompting that? My answer would be, probably not. You simply prompt your question. You get a response. You hope to get an answer that satisfies you and you continue about your day.
Now, what if youâre using the LLMs in other personal endeavors? Like writing an email? Or figuring out a DM to someone youâre trying to connect with? Or fixing your LinkedIn bio? Or writing a toast or a speech?
Sure, you can write out your response organically, or you can use an LLM to help you. Letâs say you choose the latter, how do you ensure the bot provides you with a response that keeps your personality in check?
Well, thatâs by design. And the best part? Youâre in control of that.
Only you know your personality. Only you know how you want to respond to someone. Only you know you better than anyone else. You know what sounds like you and you know what doesnât. I think you get the gist.
I would make another bet to say that you do not want to sound like an LLM - you want the LLM to sound like you in its response. That's what creates a faster workflow between you and the bot. Less editing. Less cringing at a paragraph that reads like a robot wrote it. Less talking to the dang thing and more of your actual voice showing up on the first try.
So How Do You Actually Do This?
The best way to have the bot respond like you is to give it something you've already written. Emails you've sent, posts you've published, messages you've written - basically anything that captures how you naturally communicate.
Quick disclaimer: Please don't share any personal or sensitive information. But anything you feel comfortable providing? Hand it over.
Then, enter a prompt like this:
"I'm going to share a few samples of my writing. I want you to study my tone, word choice, sentence structure, and overall voice. Once you have a feel for how I write, I want every response you give me to match that style. Don't be overly formal. Don't add fluff. Write the way I write."
From there, share your samples and let the LLM do its damn thing!
You'll notice an immediate difference. Seriously, like the responses will start to feel more like something you'd actually say - not something a bot generated for you.
The Takeaway
LLMs are powerful tools, but they're only as good as the direction you give them. If you're getting back generic and just weird robotic-sounding copy - that's not the bot's fault. That's a prompting problem. So give it your personality upfront and it'll give you back something you can actually useâŚlike right away.
Stop editing AI outputs to sound like you. Start prompting so they already do.

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Before You Go!
Thanks for reading. Next week, weâll be back with an AI-forward edition that weâre really excited about.
In the meantime, if you canât go a full week without us đ¤Ł, check out my LinkedIn post (that actually went viral) about my 10 lessons in underwriting.
As always, see you next Tuesday.

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