The HR Cassandra Problem
The other evening, I was reading Legends of Olympus to my son—one of those kids’ books that somehow ends up explaining your whole career back to you. We got to the story of Cassandra: the prophet cursed to speak the truth but never be believed.
And I just sat there, book half-closed, thinking: oh. That’s it. That’s how I sometimes feel in HR.
👂 Let me explain.
⚠️ Note: This series pulls from dozens of convos with HR leaders, founders, and the ghost of startups past. Any resemblance to real companies—living or flailing—is purely systemic.
🧵 TL;DR: Sometimes being in HR feels like being Cassandra from Greek mythology: you can see the problems coming, you warn people, you even show them the data—and they still ignore you. Until it breaks. This is about what it’s like to be early, how to stay effective anyway, and why it’s not you—it’s the system.
I once ran a workshop that started like a brainstorm and ended like a group therapy session. People were cracking jokes at first, but thirty minutes in, we were in deep systems territory: misaligned incentives, unspoken resentment, lack of clarity, feedback loops that went nowhere. It was like lifting a floorboard and finding an entire colony of termites just chilling under your org chart.
We used sticky notes, but not the performative kind. These were real. Honest. One person wrote, "I feel like my job has been redesigned three times without anyone telling me." Another said, "I can’t push back on my manager because they’re clearly drowning too."
By the end, we weren’t just diagnosing—we had a clear picture. The root causes were structural, not personal. Role confusion. Broken escalation paths. A leadership style that rewarded short-term delivery and ignored long-term burnout.
So I did what HR people do. I summarized it. I made it visual. I framed it in business terms and sent it up.
And leadership?
Leadership squinted, shrugged, and said:
👉 "Hmm, I’m not sure it’s really that bad. Let’s wait and see."
⏳ Wait and see.
Welcome to the Cassandra Problem of HR.
🧠 When You Know Too Much and Can Do Too Little
In Greek mythology, Cassandra was given the gift of prophecy and the curse that no one would believe her. She tried to warn the Trojans not to bring that shiny wooden horse into the city walls. She told them it was a trap. They ignored her. And we all know how that ended.
If you’ve ever tried to warn your CEO that their favorite Head of Sales is actively driving attrition, you get it.
This is the power paradox in HR:
We have proximity to the truth, but not the power to act on it.
We know where the bodies are buried—but not always the political capital to excavate.
And the systems thinker in you can see the loop forming:
🔁 Dysfunction → burnout → attrition → hiring freeze → overwork → more dysfunction
But until something breaks— until the funding round falls through, until Glassdoor goes radioactive, until the engineer everyone liked rage quits mid-sprint— nothing changes.
Because most leadership teams don’t move based on risk.
They move based on pain.
🚨 HR Is the Smoke Detector, Not the Fire
And let’s be honest: half of our job is smelling smoke before anyone else even registers heat.
We are the early-warning system. The canary in the coal mine.
Which means: we notice the invisible stuff.
⚠️ Micro-frictions
⚠️ Withheld feedback
⚠️ Trust decay
⚠️ Morale corrosion that doesn’t show up on the metrics dashboard
But if your exec team only acts when there's a bonfire, then of course they’ll see your concerns as "soft."
It’s not that they disagree with you.
It’s that they don’t feel it yet.
Data might tell a story, but most leaders don’t act until the problem becomes personal—until a top performer walks, or a client complains, or the board starts asking questions. Until then, your well-researched HR deck is just background noise to their immediate priorities.
🔧 So What Do You Do When You're the Only One Seeing the Cracks?
You can't force people to care.
But you can change how you make them feel the risk.
Here’s what actually helps (some of the time):
✅ Translate people problems into business consequences.
"Lack of clarity" doesn’t land.
"3 out of 5 top performers are considering leaving because they don’t trust their manager" might.
✅ Frame it like a product problem.
Founders get customer churn. They get leaky funnels. So speak their language.
“Imagine spending thousands to get a new user, and then they delete the app by day 28. That’s what our onboarding looks like right now—people join, but they bounce before they ever get to value.”
✅ Stop asking for permission to do small, reversible things.
Redesign a retro. Pilot a better feedback loop. Run a one-off manager coaching session. Prove it works before pitching it big.
✅ Build allies, not just cases.
Get a few respected team leads or middle managers to echo what you’re seeing. It sticks better when it comes from someone "in the business."
✅ Track your receipts.
You don’t need to say “I told you so.” But you do need to quietly document what was flagged, when, and what changed after it was ignored.
🥶 Here’s the Hard Part
Some cultures need to break before they’re willing to change. They won’t touch the system until it fails in public—or on a P&L.
And sometimes your job isn’t to prevent the crash—it’s to pad the landing, salvage the trust, and make sure someone remembers what went wrong so it doesn’t happen again.
In HR, you’re not powerless. You’re just early. And early feels lonely.
You’re not powerless. You’re early.
And in HR, being early is both a curse and a superpower.
Just don’t mistake being ignored for being wrong.
👉 Forward this to someone who smells smoke but isn’t being heard yet.
