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

Megan Gerhardt • November 16, 2025

you're going to love this.

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?

Why Generation A Might Just Be the...Analog Generation

By Megan Gerhardt • February 13, 2026
It has been said that everything old becomes new again on a long enough timeline. There's a fascinating generational trend I've been seeing among younger Gen Zs and the oldest of Gen A (Note: I am not calling that generation Gen Alpha, because that name is nonsensical and outdated already, and that generation is barely in their teens. More on that soon)--a craving for low-tech, no-tech, screen-free experiences. Gentelligence focuses primarily on generational dynamics in the workplace, and I do predict this will have implications for where and how these generations want to work. Despite the chaos surrounding back-to-office policies and experiments, our youngest members of the workplace (and our soon-to-be newest employees) are showing signs that they value time away from screens. I first noticed this last year among my own students, who were overwhelmingly setting change goals in my change management class focused on reducing screen time. Versions included "cleaning up my sleep routine" (putting the phone away at least 30 minutes before bed, eliminating blue light before bed, reading physical books), "reduce my weekly screentime", "stop doomscrolling", and "impose limits on TikTok and Instagram time". It was a sign that it was no longer just their parents or older generations who wanted them off their phones; they wanted themselves off their phones, too. For a wave of young people raised in an era of tech overload, it seems we have reached the point of maximum saturation, and they are pushing back. As one of my students astutely mentioned to me last year, "There are no boundaries now...our generation is just trying to figure out how to put some of them back." I've doubled down on the need for this in my teaching, having conversations with students about how to ethically use AI as a thought-partner while balancing protected time for our most scarce resource these days: deep thinking and connection. It was this need, coupled with the overwhelming research showing the improved retention and learning that occurs when students handwrite their notes and put away their laptops in class, that led me to declare our classroom a laptop and phone-free zone. We still use slides to guide conversations, but there are no longer 30 laptop screens popped up in front of them, distracting even those who are trying hard to focus. Surprisingly, I've had very little pushback. I was concerned they would feel like I was forcing them backwards, but collectively we seem to be exhaling. The discussions have never been better. As our younger Gen Zs reach young adulthood and our oldest Gen As become teenagers, they are emerging from a kind of social experiment they entered unwittingly — a life that has never known a world without constant screens. They are realizing how different they feel when they unplug. Gen Z and Gen A even have a term for this: touching grass. That's right, when the default is constant tech immersion, they had to come up with a phrase to represent the intentional effort it takes to step away. Whenever possible, I try to engage in some real-time generational anthropology, just to explore my hunches and (when possible) debunk stereotypes. Gentelligence is all about being curious rather than judgmental, and I am most definitely curious about these early signs that our younger generations are seeking a better balance between their tech and non-tech worlds. Last month, I was in Chicago for a keynote and found myself in a trendy food hall over lunch. There were little shops surrounding the food hall, including one of my all-time weaknesses, a stationery store . Pens! Journals! Paper! Notebooks! (I, too, love the analog. After indulging myself in a number of vital paper goods, I was tucking into a sandwich in the food hall and saw a (literally) noteworthy sight: a table of early 20-somethings, gathering on their lunch hour and...writing in their journals. Multi-colored pens, stamps, and conversation were plentiful. There was not a phone in sight. That in and of itself was remarkable. It turns out that stationary stores are experiencing a resurgence . Knitting, crocheting, embroidery, and sourdough baking are also all having a moment. Physical books ( and bookstores! ) are making a comeback. A few weeks later, I was at another event, this time a very trendy commercial interior design conference, where we were discussing ways to design spaces that promote intergenerational interactions (yes, it was as cool as you might be thinking). I saw a young designer at the cocktail hour and walked over to introduce myself. I asked if I could pick her brain on something, as I figured it was part of her JOB to be up on the latest trends. I asked her whether she was feeling a personal pull to use less tech, or if this was something she had seen among her peers. That's when she told me about Analog Bags . (I won't go down that rabbit hole here, but feel free to explore the link and know that I am absolutely creating my own Analog Bag as we speak). At that same design conference, a book was recommended to me: Megatrends by John Naisbett. The gentleman who suggested it said it changed his life. He thought I would find it interesting, given my interest in generational trends, behavioral cycles, and, of course, my classes in change management. I ordered it as soon as I got back to my hotel room (fun fact: it was published in 1982, so you'll have to find a vintage copy!). I've been devouring it, and among the many eye-opening insights was the observation that " the more 'High Tech' we become, the more we need 'High Touch.” Now, Naisbett was referring to the high-tech era of the early 1980s, when personal computers were entering the scene, but the relevance of the comment almost 45 years later, in the age of AI, was not lost on me. Those who have lived their entire lives as products of high-tech are now blazing the trail to meet their need for high touch. Let this be my formal declaration (for whatever it's worth) that I predict our youngest generations will lead us back to a balance between tech and high-touch: they are the proverbial canaries in the coal mine, and their message is clear. They are living, breathing embodiments of a life flooded with endless tech, fake news, constant connectivity, dopamine hits, and input dictated by algorithms, and it appears they may have had enough.

Out of Respect: Generational Differences Captured in One Sentence

By Megan Gerhardt • January 12, 2026
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When 'Common Sense' Isn't Common Across Generations: The Curse of Knowledge

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Maybe i do too.

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It wasn't a planned comment.

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I've always loved invisible ink.

Why Gen Needs to End That Text With an Emoji (haha, lol)

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the plot thickens.

Is Your Workplace Multi-Generational or Intergenerational? It Matters

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Generational Fish

By Megan Gerhardt • March 25, 2025
Here's the thing about water.
diverse students

3 Things HR Must Do to Build Gentelligence

By Megan Gerhardt • February 9, 2025
Is a multigenerational workforce an opportunity or a threat? It might be up to HR. Research is clear on this: it depends on how that age diversity is managed and the workplace culture that surrounds it. Really. That is the linchpin on all of this, which means it’s entirely up to your organization to do what it takes to turn what most see as frustration into an incredibly valuable human capital asset.