
A reader named Irene left a comment that stopped me mid-scroll:
“I used ChatGPT to rehearse for a job interview last year. Had it play the interviewer and ask tough follow-up questions. I got the job.”
A few comments down, Ben added:
“I have a conference talk in two months and I’m going to try using ChatGPT to practice Q&A.”
Two people, same week, same idea — using AI not to write something for them, but to pressure-test them. That’s the distinction worth exploring.
The Old Way vs. the AI Way
Most people prep for interviews by reviewing their resume, googling common questions, and maybe doing one practice run with a friend who goes easy on them. Same with presentations — you run through your slides alone, time yourself, and hope for the best.
The problem: neither of these puts you under real pressure. Your friend doesn’t know enough about your field to ask the hard follow-ups. And talking to yourself in the mirror doesn’t simulate the moment an audience member challenges your data.
AI changes the equation. You can now summon a pressure-test partner at 11pm, for free, who never gets tired, never pulls punches (if you ask it not to), and can play the role of a skeptical panel, a hostile interviewer, or a confused audience member — on demand.
Setting It Up: The Right Prompt Makes All the Difference
The key is being specific about the role you want AI to play. Vague prompts get vague results.
For job interviews:
“I’m interviewing for a senior product manager role at a B2B SaaS company. You are the hiring manager. Interview me for this position. Ask me behavioral questions using the STAR format, then follow up with skeptical clarifying questions when my answers are too vague. Don’t let me off easy.”
That last sentence matters. Without it, most models will be polite. You want it to mirror what a tough interviewer actually does — push on weak answers, probe for specifics, challenge assumptions.
For conference talks and presentations:
“I’m giving a 20-minute talk on [your topic] at a technical conference. After I explain my main argument, play the role of an audience member who is skeptical of my methodology. Ask the questions that would make me sweat.”
Then actually deliver your explanation out loud or in text, and let the AI respond. You’ll be surprised how quickly the gaps in your argument become obvious.
Go Deeper: Scenarios Worth Trying
The hostile interviewer. Ask AI to be adversarial — to question your career gaps, challenge your accomplishments, or probe whether your “team win” was really yours. Uncomfortable? Yes. Useful? Very.
The confused audience member. For presentations, have AI roleplay someone from outside your domain who doesn’t understand your jargon. If you can’t explain it simply when pressed, you don’t know it well enough yet.
The panel format. Ask AI to switch between two or three different interviewer personas — one technical, one focused on culture fit, one skeptical of your experience level. Real panels do this; you might as well rehearse for it.
The post-talk Q&A gauntlet. After walking through your slides in text, ask AI to fire five hard questions in a row. Then review your answers and ask AI to rate which were strong, which were evasive, and what a better answer might have looked like.
What AI Can’t Replicate (and What to Do About It)
Let’s be honest: AI doesn’t feel. It won’t actually make your palms sweat. The physiological part of speaking in front of people — the adrenaline, the time distortion, the way your voice changes — that still requires humans.
So the move is to layer the two together:
- Use AI to stress-test your content and answers — the intellectual layer.
- Use actual humans (or video self-recordings) to stress-test your delivery — the physical layer.
AI gets you 80% of the way there faster than any other method. The last 20% requires getting in front of real people.
A Note on Using This for More Than Jobs
The same technique works for:
- Salary negotiations — have AI play a resistant manager and practice holding your position
- Client pitches — roleplay a skeptical client who has budget concerns
- Difficult conversations — rehearse how you’ll bring up a sensitive topic with a colleague or family member
- School presentations — students can use this to practice defending a thesis or project before a teacher does it live
The pattern is always the same: you need to practice being challenged, and finding a willing, knowledgeable sparring partner on demand used to be hard. Now it isn’t.
Try It Today
If you have an interview, presentation, or high-stakes conversation coming up, open your AI tool of choice and paste in one of the prompts above. Don’t wait until the night before.
And if you try it and something surprising happens — you found a gap in your argument you didn’t know was there, or an interview answer you’d been giving for years that actually doesn’t hold up — I’d love to hear about it in the comments.
That’s how Irene’s comment became this post.
Have a topic you’d like to see covered? Leave a comment or reach out — reader questions and stories are some of the best sources for posts on this site.


Leave a comment