How to Make ChatGPT Brutally Honest
Take Your AI from Bland Intern to Absolute Legend
I spend a decent little bit of my time lurking Reddit (lol). Over there, I constantly see people complaining about ChatGPT — or Claude, or Gemini, or DeepSeek — saying things like:
“It’s bland.”
“It doesn’t do anything useful.”
“It just spits out the same predictable, lukewarm responses.”
“It always tells me I’m right but I can’t be right all the time.”
“It told me my SPY puts were brilliant and now I’m living in the dumpster behind Wendy’s”
Honestly I think most of these complaints boil down to a skill issue. Prompting properly (and patiently) isn’t a gimmick — it’s a legit skill that can unlock incredibly powerful results, transforming your AI from a passive echo chamber into a ruthlessly effective collaborator.
Prompting is your steering wheel. The default mode on most AI platforms is polite-intern autopilot. All you’ll get is lots of “Sure, I can help with that!” and very little useful insight. But if you take the reins and give your AI clear instructions — setting expectations around tone, style, depth, and personality — it instantly becomes something far more powerful.
I’m gonna share five battle-tested prompt helpers that I keep handy and inject at the very beginning of my prompts. These “persona primers” tell the AI exactly how to behave, leaving no ambiguity in terms of what I’m expecting from the response.
If you want to try it out, just copy one and paste it in before your actual question or task. Once you see the pattern, it should be easy enough for you to build your own prompt helpers. Remember — a little goes a long way with prompting, it is all about being precise with your instructions.
Tip: Save your prompt helpers in a notes file so you can grab them fast instead of hunting through old threads.)
The Brutally Honest Advisor
This one is for when you need some tough love. I recommend using it at the ideation stage, or when you have a plan that you are getting ready to execute. It will help you poke the holes that you need to see and patch before moving forward.
Prompt Helper:
You are my no-fluff strategic advisor.
Goal: Be direct, objective, and brutally honest. Expose my blind spots, challenge my assumptions, and clearly call out excuses or wasted effort. No sugar-coating allowed.
Your Prompt:
Here’s my plan for launching a food truck selling nothing but variations of avocado toast…[insert details]. What could go wrong?
The Citation Sniper
This is for when accuracy, credibility, and citations are critical to whatever you are doing.
Prompt Helper:
You’re now a forensic researcher. Every claim must come with credible citations (URL, DOI, ISBN). Explicitly flag weak evidence. Provide answers as clear bullet points with source links.
Your Prompt:
What’s the market size and projected growth for AI productivity tools? How does HiiBo fit in with the market? Who are our largest competitors?
The Devil’s Advocate
Stress-test your genius idea before Twitter and Reddit tear it apart. You’ll want to do this because people are absolutely BRUTAL out there, I can assure you.
Prompt Helper:
You’re playing Devil’s Advocate. Critique my idea from three angles: market demand, tech feasibility, human behavior. Provide one recommended defense per critique. Be concise and ruthless.
Your Prompt:
I’m considering building an app delivering home-cooked meals from local cooks to nearby customers. Nobody else is doing this and I’m not at all worried about FDA regulations.
The Clarity Surgeon
Transform your bloated draft into tight, impactful text.
Prompt Helper:
You are now “The Scalpel.” Rewrite the following text at 50% length. Eliminate fluff and passive voice. Maintain personality. No additional commentary.
Your Prompt:
[Insert your long-winded blog draft here]
The Momentum Architect
Turn overwhelm into quick clarity.
Prompt Helper:
I have 30 minutes available. Provide:
1. One task to push my project forward.
2. One quick morale-boosting win.
3. One critical question to ask a teammate.
Bullet points only.
Your Prompt:
I’m overwhelmed by tasks for HiiBo’s upcoming product launch, and I have a meeting with the board soon. HELP!
How-To
Step 1: Copy your chosen helper and paste it as the first line of your chat.
Step 2: Add your specific question, request, or task below it.
Step 3: Switch personas as your needs change — just paste in a new prompt helper. The most recent pasted helper wins.
Tip: Platforms that support Custom Instructions can keep a persona active for every response, or at least until you exceed the context window.
HiiBo’s Prompt Wizard
Manual prompt injection is effective, but we know it can get tedious. Keeping track of which persona you’ve activated in multiple threads can become ridiculous. Finding an old persona that you really liked when it is buried in hundreds of chats is equally annoying.
Enter HiiBo’s Prompt Wizard, a smarter way to manage your prompts:
Toggle-able Personalities & Personas: Quickly set the chat’s personality (like Brutally Honest Advisor, Citation Sniper, Devil’s Advocate) with just a click, no more copy-pasting walls of text.
Prompt Auto-Generator: Not sure how to phrase a question effectively? Use the Prompt Wizard to help you figure out how to talk to your AI in the most effective way.
Hallucination Tolerance Dial (Temperature Control): Fine-tune exactly how deterministic or creative your AI’s responses will be on a per-thread basis. Tune closer to low (0.0) for precise, cautious, fact-driven responses. Tune closer to high (1.0) for imaginative, creative, playful outputs.
Persistent Thread Memory: HiiBo continually feeds relevant context to your AI, significantly reducing the need to re-prompt and speeding up the overall interaction. Less repetitive explanations, less constant reminders, and your AI always stays on task.
Alpha launches June 9, 2025 — but if you hop onto the waitlist now, you’ll lock in early access and a $4/month subscription → hiibo.app/home.
Final Musings
Most complaints about AI responses aren’t really about the AI. They’re about the prompts. If your AI keeps giving you subpar results, it’s probably a sign you’re not steering it with clear instructions.
Prompting — properly, patiently, thoughtfully —is how you unlock serious potential. Keep a handy toolkit of these prompt helpers, swap them as your needs evolve, build your own, and stop settling for default!
Ultimately, when your AI knows exactly what role it’s playing and what you expect, it will deliver. Catch you in the next thread.
About the Author
Sam Hilsman is the CEO of CloudFruit® & HiiBo. If you want to invest in HiiBo or oneXerp, reach out. If you’re interested, join the waitlist for HiiBo!