
There’s a problem with most AI assistants.
They’re too polite.
They hedge. They soften. They “suggest” instead of telling you what’s actually broken. You end up with something that sounds helpful, but quietly lets bad thinking, weak ideas, or flawed execution slip through.
At the other extreme, you’ve got the idea of full, unfiltered honesty. If you’ve seen Interstellar, you’ll remember TARS and the adjustable honesty setting. It’s a great concept, but in practice, 100% blunt honesty isn’t that useful either. It tips into abrasive, unproductive, and sometimes just noise.
What you actually want sits somewhere in the middle:
Clear. Direct. Honest. But still constructive.
That’s the gap I built a small AI “skill” for.
I call it: Hurt Me Plenty.
Why “Hurt Me Plenty”?
The name is borrowed from DOOM.
If you’ve played it, you’ll know “Hurt Me Plenty” sits in that middle ground. Not the easiest mode, not the most punishing either. Just enough pressure to keep you sharp.
And that’s the key point.
It wasn’t about being punished endlessly. It was about how long you could operate effectively under pressure. Stay focused. Stay accurate. Keep moving forward without getting sloppy.
That’s exactly the behaviour I want from AI.
Not brutal for the sake of it. Not soft to the point of uselessness.
Just enough intensity to expose mistakes early and force better decisions.
The Problem: Polite AI Is a Risk Multiplier
In engineering, product, or leadership, bad ideas don’t usually fail loudly. They fail quietly.
- A flawed architecture gets a “this could work” instead of “this will break under load.”
- A weak strategy gets “interesting direction” instead of “this won’t deliver commercial value.”
- A risky plan gets “worth exploring” instead of “this will cause problems later.”
Polite AI reinforces that.
It mirrors the worst version of corporate feedback loops. Everything sounds reasonable. Nothing gets challenged properly.
And if you’re operating in a high-stakes environment, especially regulated systems like iGaming or fintech, that’s dangerous.
You don’t need encouragement.
You need signal.
The Other Extreme: Brutal Honesty Doesn’t Scale Either
There’s a temptation to swing the other way.
“Just tell me the truth. No filter.”
Sounds good in theory. In reality, it breaks down quickly:
- It becomes performative bluntness rather than useful critique
- It lacks prioritisation (everything is “wrong”)
- It erodes trust instead of building it
- It doesn’t guide you toward a better outcome
Raw honesty without structure is just noise with attitude.
The Middle Ground: Precision Critique
What I actually want from AI is this:
- Tell me what’s wrong
- Tell me why it matters
- Tell me what to do about it
- Don’t sugar-coat it
- Don’t be a dick about it
That’s the design philosophy behind Hurt Me Plenty.
It’s not about being harsh. It’s about being usefully exacting.
What “Hurt Me Plenty” Actually Does
At a practical level, it’s a prompting layer / skill that changes how the AI behaves.
Instead of defaulting to “helpful assistant,” it switches into something closer to:
A senior technical reviewer who is accountable for the outcome.
The behaviour shift is subtle but important:
1. No Passive Agreement
If something is weak, it gets called out directly.
Not:
“This is an interesting approach…”
But:
“This will likely fail because X, Y, Z.”
2. Prioritised Criticism
Not everything matters equally.
The skill forces the model to focus on:
- Critical flaws first
- Then structural issues
- Then optimisation or polish
3. Reasoned, Not Emotional
It avoids tone for tone’s sake.
Every critique has to tie back to:
- risk
- performance
- scalability
- commercial impact
- delivery feasibility
4. Actionable Corrections
Pointing out problems is easy.
Fixing them is where value is.
Each critique is paired with:
- a suggested alternative
- or a direction of improvement
- or a decision framework
5. No False Positivity
If something is genuinely good, it says so.
But it doesn’t pad weak work with artificial praise.
Where This Becomes Useful (Very Quickly)
I’ve found this kind of behaviour disproportionately valuable in a few areas:
Architecture & Engineering Decisions
Cuts through “this might work” and gets to:
- will it scale?
- where will it break?
- what’s the real bottleneck?
Strategy & Commercial Thinking
Particularly in iGaming and regulated systems:
- does this actually deliver value?
- is this compliant in practice, not theory?
- where’s the hidden risk?
Internal Communication
Drafts, proposals, updates:
- is this clear?
- is it credible?
- would a CTO / CEO actually buy this?
AI-Assisted Development
Ironically, this is where AI often fails most.
Without critique, you get:
- syntactically correct code
- structurally poor systems
“Hurt Me Plenty” forces:
- better design decisions
- clearer trade-offs
- fewer hidden problems
Try It Yourself
I’ve put the skill up publicly so you can use or adapt it:
- GitHub repo: https://github.com/campbellchief-testy/fun-skills-repo
- Direct skill file: https://github.com/campbellchief-testy/fun-skills-repo/blob/main/hurt-me-plenty-mode.md
It’s intentionally simple. This isn’t about complex tooling. It’s about changing the behaviour of the system you’re already using.
Drop it into your workflow and you’ll feel the difference almost immediately.
The Key Insight: AI Needs Friction
Most people are trying to make AI smoother.
More helpful. More agreeable. More aligned.
That’s only half the story.
For real work, especially at senior levels, you need friction:
- something that challenges assumptions
- something that flags risk early
- something that forces better decisions
That’s what this kind of skill introduces.
Not hostility.
Not ego.
Just useful resistance.
Final Thought
If your AI always agrees with you, it’s not helping you.
It’s just accelerating your mistakes.
The goal isn’t an assistant that makes you feel right.
It’s one that helps you be right.
And sometimes, that means hearing exactly where you’re getting it wrong.






















