My Employee Used AI to Ask for a Raise. So I Used AI to Say No — Here's What Happened Next We're watching the death of workplace communication and the birth of a new kind of cowardice: one where being professional means being processed and where sounding smart means sounding artificial.
By Shayne Fitz-Coy Edited by Micah Zimmerman
Key Takeaways
- AI-mediated conversations create a "feedback loop from hell" where people stop talking to each other.
- When salary negotiations become algorithmic, both sides lose the nuance needed for fair resolution.
- Complex workplace situations like remote pay equity require human judgment that algorithms can't replicate.
Opinions expressed by Entrepreneur contributors are their own.
Last month, I stared at my screen as an email forwarded from one of my managers hit my inbox:
"According to available industry data, the average annual salary for a Coordinator in New York ranges from approximately 73k to 82k. Given my performance over the past year and the increasing scope of my responsibilities, I believe it is reasonable to request a salary adjustment that aligns with the value I contribute to the team and my ongoing commitment to the role."
I knew immediately that the text was AI-generated. Not because of the wooden phrasing or precise salary range. I knew because nobody asking for their own money sounds this afraid of wanting it.
My manager's response was equally robotic:
"Thank you for reaching out about your impressive progress and growing contributions. While we value the impact you've had, we are currently unable to accommodate the salary increase at this time. We remain committed to recognizing your growth and will continue to evaluate opportunities..."
Two emails, two different people, and every word sounded like it came from the same ChatGPT template.
Because it did.
Welcome to the feedback loop from hell
We're watching the death of workplace communication and the birth of a new kind of cowardice: one where being professional means being processed, sounding smart means sounding artificial and where the most human thing to do is let a machine speak for you.
AI isn't the culprit here. It's a mirror. It reflects a workplace culture that avoids discomfort in the name of professionalism.
Here's what happened: An employee working remotely in Portugal used AI to request New York wages (the employee's old address). The manager used AI to reject the request without addressing the geographic complexity.
It was like watching people argue through Google Translate, except the translation was into Corporate Speak and back again.
This is the ChatGPT generation's version of hiding behind email instead of picking up the phone, except now we're hiding behind algorithms instead of being ourselves.
I faced a choice: fire up ChatGPT for my own response or be a human being.
I chose humanity: "Let's chat live on Thursday. Copy HR."
The business cost of artificial communication
This isn't a story about AI making us lazy. It's about what happens when we use technology to avoid the conversations that matter most and that cost our businesses.
The employee who used ChatGPT wasn't trying to deceive anyone. She was trying to sound "professional" while navigating a complex reality that requires actual negotiation.
We avoided a conversation that needed nuance and ended up with a conversation that had none.
What are we afraid of when we avoid direct conversation?
But here's the harder question: What conditions did I create that made my employee believe only AI could speak for them?
This wasn't just about a fear of being direct. It was about a workplace culture where authentic requests felt too risky to voice. Where being 'professional' had somehow become more important than being human.
The manager could have broken this chain by responding to the person, not the prose. I could have broken it sooner by creating conditions where people felt safe asking for what they're worth in their own words.
Are we outsourcing judgment or just conflict?
But when an employee outsources asking for a raise to ChatGPT, what they're really saying is: "I don't trust my own words to be worth your time." And when a manager responds with AI, they're saying: "Your request isn't worth my authentic attention."
This is how relationships die in the workplace — not with conflict, but with the slow suffocation of genuine communication. And dead relationships don't drive business results.
Related: Different Types of Toxic People in the Workplace
The competitive advantage of human leadership
When I insisted on a live conversation, something remarkable happened. Within 20 minutes, we'd worked out a solution that acknowledged both the employee's contributions and the realities of our global compensation structure.
We discussed:
- The employee's actual value creation (significant)
- Geographic pay considerations (complex but manageable)
- Career progression opportunities (more valuable than immediate salary bumps)
- Performance metrics tied to future increases (clear and achievable)
None of this could have emerged from an AI exchange. The solution required human judgment about fairness, business constraints and individual circumstances.
While competitors let AI handle their "difficult" conversations, we're building stronger relationships with our people. In a remote-first world, authentic communication has become our secret weapon for talent retention.
Conversations about money, fairness and contribution are too important to delegate to code. They call for presence, humility and often, when there are people on the other side, live dialogue.
Why this matters for every business leader
We're creating a world where the most important conversations sound like they're happening between chatbots. When someone's livelihood is on the line, they deserve a human response.
The fix isn't banning AI from workplace communications. It's recognizing when the stakes are too high for artificial responses.
I didn't just end an AI feedback loop when I insisted on talking live. I reminded everyone involved that some problems are too complex for anything other than genuine human conversation.
In a world where we're teaching machines to sound human, the most radical business act is ensuring humans sound human when it matters most.
So here's our policy now: if the conversation feels hard, we have it live. If it involves money, fairness or the future, we show up in person or as close to it as we can. No scripts. No templates. Just two people, trying to get it right together.
