I asked AI to rewrite my email like a Gen Z. And a Millennial. And A Gen Xer. And a Boomer. Watch What Happened.

The idea came to me last week during a keynote. I was sharing my most sticky, crowd-favorite example of the Gentelligence practice of Identifying Assumptions: that Gen Z tends to interpret periods at the ends of text messages as harsh and sour, whereas people my age and older tend to see them as necessary and professional (if you missed this life-changing discovery, you can read all about it here. It became part of a CNN quiz. No big deal). Without exception, this example sets the room abuzz. Once you see it, you can't unsee it. Scroll your texts: Gen Zs don't use the period to end the message. Sometimes an emoji. Sometimes an LOL or a hahaha (check out why here). But never a period.

During the Q & A session, an audience member identified herself as a Gen Z and admitted she is a generous user of the exclamation point in her emails, trying to keep the tone light and upbeat. "Should I...remove some?" she asked. "To be taken more seriously?"

This was a fascinating question, and I am so hip these days that my first thought was "I wonder what AI would do if she asked it to revise her email to be less...Gen Z?"  Now, if you're new here, you may not know that I abhor all Generational Stereotypes and push back on generalizations, but at the same time, I embrace and research generational norms like it's my literal job. It's a delicate distinction, so while I did not suggest she use AI for this and instead told her authenticity and self-awareness were important in any communication, but so was knowing her audience. If she was realizing she may disproportionately use explanation points to "soften" her tone when compared to her older colleagues, this was interesting data and perhaps she could experiment with whether that was helpful. But my brain was already spinning.

Twenty minutes later the keynote was over and I was back in the car. My amazing husband had offered to drive me the few hours over to Indianapolis for this talk, so I had barely closed the door before I grabbed my trusty Claude AI app and went to work (note: Claude and I are close. He is my favorite AI thinking partner. He needs a lot of coaching and feedback, but I enjoy experimenting to see how well he can do with questions, and also like seeing where I am still convinced he cannot replace me). By the time we pulled in our driveway, I had finished my experiment.

Here was my question: we know AI is biased. Humans have trained AI, and humans are inherently biased. We are already seeing evidence that AI is ageist and all other kinds of ists. But I have yet to see anyone ask if AI has generational bias.  Today, dear readers, that person will be me. What has AI learned from us about generational communication styles? Would I be delighted by the nuance or horrified by the stereotypes?

I jotted off a quick, generic draft of a work email (or was this really a Gen X style email, because I am a product of my generational norms?)

Hi Megan, Hope you are doing well. I have had a long week and have been dealing with a lot of personal issues, so unfortunately, I am not going to get the project in by the deadline. Thanks for understanding.

Thanks, Sarah

Then I told Claude: Edit this email to write it like a Baby Boomer.

(My favorite part is when Claude explains his process to me: Analyzing Baby Boomer communication habits. Thinking.

Result:

Dear Megan,

I hope this email finds you well and that you are having a good week.

I wanted to reach out to you personally regarding the project that is due. I am writing to sincerely apologize, as I will not be able to meet the deadline we discussed. This week has been particularly challenging for me, as I have been dealing with some unexpected personal matters that have required my immediate attention. I realize this puts you in a difficult position, and I take full responsibility for not being able to deliver on time.

I truly appreciate your understanding and patience during this time. If possible, I would welcome the opportunity to discuss this with you further, either by phone or in person, at your convenience. I want to assure you that I remain committed to completing this project to the best of my ability and would like to work with you to establish a new, realistic timeline.

Again, I apologize for any inconvenience this may cause, and I greatly appreciate your support and understanding.

Warm regards,

Sarah

Claude explains his work to me:

Key changes: More formal tone, longer and more detailed explanation, explicit apology multiple times, offers to discuss by phone/in person, acknowledges impact on the other person, and uses more traditional business letter language.

Now I tell Claude to edit it to sound like a Gen Xer:

Hi Megan,

I need to let you know I'm not going to make the deadline on this project. I've had some personal stuff come up this week that I needed to deal with.

I can get it to you by [specific date]. Let me know if that works or if you need to discuss alternatives.

Thanks,

Sarah

Key changes: Direct and to the point, minimal explanation without oversharing, solution-oriented (proposes new date), no excessive apologies, maintains professional but casual tone, and gets straight to business. Gen Xers tend to be pragmatic and efficient communicators who don't feel the need to over-explain or apologize profusely—they state the problem and move toward a solution.

Now I'm getting cranky with Claude and his generational stereotyping. (Note I was less cranky when he was stereotyping Boomers, but now he's stereotyping my generation so it's getting real).  Do I disagree with this in terms of my own personal email style? No. I infamously am not chatty or overly friendly in my emails. My sample size of Gen X colleagues and friends is vast, and there is of course variance based on all those other layers of our identity: personality being the most impactful. My colleague and good friend Dan is the living embodiment of all the best parts of Ted Lasso, and he would never send a message without genuinely wanting to inquire how I was and expressing gratitude for whatever we were resolving in the communication. Other friends of mine that I will not name fall even further on the range of terse and non-interested in the chit chat. But as a Gen X norm? Yes, I would hypothesize Gen Xers use fewer words per email than your average Baby Boomer, based likely on norms around formality and definitions of professionalism, as well as when email was introduce as a form of work communication. It's an empirical question. My favorite.

Moving on. I know you are waiting for the Millennial version. Millennials are the largest generation in the workplace, and the ones that have gotten the roughest treatment. I love Millennials. (You can verify this is true because I even have a TEDx about it, which you should watch, because mine has about 18,000 views and Brene Brown's first TED talk has about 18 million views, so I'm a little behind). Would Claude share my positive view, or was this about to be another generational shaming?

I asked Claude to rewrite that email like a Millennial:

Hey Megan,

I hope you're doing well! I wanted to reach out because I need to be transparent with you about the project.

This week has been really rough—I've been dealing with some personal stuff that's honestly taken more out of me than I expected. I hate to do this, but I'm not going to be able to hit the deadline. I'm really sorry and I know this probably throws things off for you.

I'm wondering if we could potentially push it to [specific date]? I want to make sure I can give this the attention it deserves rather than rushing through it. I'm totally open to hopping on a call to talk through the timeline and see what works best for both of us.

Again, I really appreciate your understanding and flexibility. Let me know what you think!

Best,

Sarah

Key changes: Casual but warm tone, transparent about mental/emotional impact ("taken more out of me"), apologetic but explains reasoning, emphasizes quality over speed, offers to collaborate on solution, uses phrases like "hop on a call" and "be transparent," and shows concern for both parties' needs. Millennials tend to be more open about struggles while still maintaining professionalism.

Dear readers, let's all pause to note that for once, Millennials were not abused or on the shame end of generational generalizations. Claude believes they are "casual but warm", "transparent", care about "quality over speed", and are "concerned about both parties' needs"!  Is this because Millennials are responsible for inventing and training most of our AI? Or because these are stronger Millennial communication norms? Questions abound.

To round out this impromptu experiment, I tell Claude it's time to rewrite the email like a Gen Z. His thought process tells me he is "architecting a casual, authentic communication framework":

hey megan,

so this is awkward but i wanted to give you a heads up that i'm not gonna be able to hit the deadline for the project. ngl this week has been A LOT and i've been dealing with some personal stuff that's really been affecting my mental health.

i know this isn't ideal and i feel bad about it. would it be possible to get an extension? i just want to make sure i can actually do a good job on this instead of turning in something half-baked that neither of us will be happy with.

lmk what works for you and if you want to chat about it!

thanks for being understanding <3

sarah

Key changes: Very casual tone (lowercase, "hey," "ngl"), directly mentions mental health without hesitation, acknowledges the awkwardness upfront, shorter and more conversational, uses phrases like "lmk" and "A LOT," includes a heart emoji to soften the message, focuses on authenticity and quality, and has a more stream-of-consciousness feel. Gen Z tends to communicate more like they're texting—informal, genuine, and comfortable being vulnerable about struggles.

Oh my. Now, it's worth pointing out that Gen Z is 13-28 years old this year, so Claude is scraping the communication habits of teens along with young adults, so we have a mixed adolescent/adult situation going on here. I do appreciate Claude's positive framing of the casual approach as informal and genuine, as my own exploration of this from the texting example aligns with this interpretation. I was curious how a Gen Z young professional would react to this though, so I sent it to Hannah, my amazing Gen Z social media director (if you see good content on Gentelligence on LinkedIn, that's usually Hannah. Unless I'm really on my game that day).

Hannah was not pleased. Maybe it was the faux heart emoji?

"The Gen Z one is simply just NOT! COOL!"

"And it’s all in LOWERCASE."

Hannah is wonderful and professional and has fantastic energy, and never once has she sent me an email with a faux heart emoji or used "ngl". Her point was taken, if this was an email to her boss, I do believe Hannah would understand that the formality needed to be taken up a notch. But Claude isn't sure.

This is fascinating. This isn't a matter of clever anticdotes, gathered by yours truly at various workshops and keynotes. This is systemized generational...bias? Observation? Gathered perceptions?  Programmed or learned through humans, now providing other curious humans with these patterns and beliefs. And so it goes.

I'm off to start some formal academic research on this, folks. This is what gets me out of bed in the morning these days-stumbling upon these questions out in the field where the people are navigating these challenges, and then going back to the Gentelligence Research Lab (okay, this is actually my desk, but we are going to call it the GENTELLIGENCE RESEARCH LAB, everyone on board?) to see what shakes out if we launch our academic research approach. I have so many questions.

Can't wait to see what you all think. Is Claude right? Biased? Dangerous? Helpful? Can Claude be an ally in separating generational norms from stereotypes, or is he part of the problem?