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The millennial generation is split in 2: an older crowd with boomer-style comfort, a younger set going 'back to the early 1900s'

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CommentaryGen Z

Gen Z is using ChatGPT to practice salary negotiations and tough conversations before they happen

By
Phillip Miller
Phillip Miller
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By
Phillip Miller
Phillip Miller
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March 22, 2026, 7:00 AM ET

Phillip Miller is a 20+ year edtech executive and CEO of Skillwell, where he's building the future of immersive learning for the enterprise.

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"Hey ChatGPT, have a difficult conversation with me."Getty Images
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Young professionals are using ChatGPT to rehearse salary negotiations, deliver tough feedback, and navigate workplace conflict — before the conversations ever happen. From entry-level employees to mid-career managers, workers are turning to AI tools to prepare before stepping into their manager’s office.

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Why This Generation Needs a Practice Gym

For a generation that came of age amid remote work, economic uncertainty, and rapid technological change, preparation feels less optional and more essential. Deloitte’s global survey of more than 23,000 workers found that Gen Z and millennials are intensely focused on growth and skill development as workplace expectations evolve, and another study showed that 56% of Gen Z workers use AI to help figure out how to communicate with a boss or colleague.

For many early-career professionals, the toughest part isn’t the content of the conversation—it’s the experience of having it. That’s not a character flaw; it’s the product of a world where fewer interactions require real-time conflict resolution, emotional regulation, or face-to-face persuasion. If you’ve spent years communicating through screens and asynchronous channels, the first time you have to deliver tough feedback or negotiate on the spot can feel like showing up to a championship match without a single practice rep.

How to Try It Right Now

For the first time, that kind of practice gym is within reach. Advances in large language models have dramatically lowered the cost of creating personalized, high-quality dialogue that lets employees rehearse difficult conversations on demand.

Here’s how to start: open ChatGPT and switch to voice mode. Give it context on an upcoming situation you’re anxious about, then ask it to simulate the conversation. Tell it to challenge your assumptions, interrupt you the way a stressed manager might, or push back hard on your reasoning.

It will feel awkward at first — like your first day back in the gym after a long layoff. That’s fine. Fluency comes from repetition.

  • Listen first, then reflect.Prompt ChatGPT to listen without interrupting, then summarize what you said in three key points. This exercise alone often brings unexpected clarity.
  • Roleplay the other person.Prompt: “Pretend you are [coworker X] and help me rehearse the conversation I need to have with them.”
  • Repeat until it feels natural. The first session will feel strange. By the third, it won’t. Consistency is the only requirement.

The Next Frontier: Team-Level Training

But individual practice is only the beginning. A new generation of AI-enabled corporate trainers can now bring this kind of preparation to entire teams.

These trainers will develop adaptable lessons geared to what an employee needs to know — not what they already know. They’ll surface the conversations employees didn’t know they needed to have, tailoring training for distinct roles and seniority levels.

This isn’t theoretical. Organizations like Skillwell — which I lead — are already demonstrating that EQ leadership skills are not innate traits Over the next decade, I expect the number of people practicing professional skills via AI-enabled simulation to expand by several orders of magnitude. The tools exist. The adoption curve is just beginning.

The Gym Is Open

Real-world experience remains the best teacher. But organizations no longer have to wait for high-stakes moments to arrive — and hope their people are ready. AI-powered simulation gives every worker a place to train, build fluency, and show up prepared when it matters most.

The practice gym is open. The only question is whether your organization will walk in.

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

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