Navigating the Job Market with AI: Top Prompts for Your Job Search
AI isn’t magic, but it can be a really useful tool—especially when you’re job hunting. I’ve leaned on tools like ChatGPT and Otter.AI during my own search to write faster, prep smarter, and see my experience with fresh eyes. But let’s be real: it’s not perfect. It’s a jumping-off point, not a shortcut.
Let’s start with the biggest caveat: AI isn’t always accurate. It can make up facts, sound overly confident, or suggest things that just don’t apply to you. I always double-check AI content against my real experience. That said, it can still give you structure, language, and ideas that help you move forward faster.
Here are a few ways I’ve actually used it:
Interview Prep
I’ll ask ChatGPT to act like a career coach and help me come up with thoughtful questions—especially for roles where I want to sound sharp and strategic, not basic. Example: questions to ask a headhunting firm about a CRO role at a PE-backed company. Super specific. Way better than Googling.
Career Clarity
When I’ve felt stuck, I’ve used AI to look at my resume and suggest roles, industries, or growth areas I hadn’t considered. It’s helped surface transferable skills I’d overlooked—and made me rethink how I frame what I’m good at.
Emails + Outreach
I’ve used AI to draft intro emails to hiring managers, follow-up notes after interviews, and personalized thank-you messages. Pro tip: if you’ve recorded the interview with Otter.AI (with permission), you can even feed that transcript into ChatGPT for a more tailored follow-up. It’s next-level.
Tailoring My Resume
Probably where AI has saved me the most time. I’ve pasted in job descriptions and asked it to rewrite bullet points or draft a tailored summary. Sometimes it’s too fluffy or too formal, but as a starting point? Solid.
Cover Letters
Same idea—give it a job title, company, and your resume, and ask it to spit out a 150-word version. I always edit it down, but it helps get over the blank page hurdle.
Practicing for Interviews
I’ll ask for questions by industry or role and then generate CAR-style answers to get my brain in the right mode. It’s not a substitute for practice—but it helps you warm up.
Post-Interview Review
This is where Otter.AI comes in. I record my interviews (again: with permission!) and later run prompts like the ones below. It’s like watching game tape. I always catch things I wouldn’t have noticed in the moment:
What words or themes came up most?
How did I come across—confident, clear, rambling?
What answers hit? Which didn’t?
Bottom line:
AI can make you faster and sharper—but it still can’t speak for you. Your story, your experience, your voice—that’s what lands the job. Use these tools to support your process, not replace it. Keep your edge. Keep your authenticity.
Prompts I Actually Use (copy & paste, tweak, make your own)
Interview Prep + Career Clarity
You are a top-tier career coach. What are 10 insightful questions I can ask in an interview for a CRO role at a PE-backed company?
Based on my resume or LinkedIn, what roles or industries should I consider next?
What are my transferable skills and how can I use them elsewhere?
Where’s the growth in my field, given my background?
Emails + Follow-Ups
Write a short intro email to the hiring manager for [job title], based on my resume and the job description
Draft a follow-up note post-interview, highlighting fit and enthusiasm
(Bonus: use Otter.AI transcript for a more tailored response)
Resumes + Summaries
Tailor my resume to this [job title] at [company], using my background below
Which of these two resumes is a better fit for this job? Here’s the job description
Write five resume bullets with metrics based on the info below
Rewrite my resume for this [job title] using the job description, with 3–5 bullets per role and key keywords
Pull out eight skills to highlight for this role
Professional Summary
Write a compelling 150-word professional summary based on my resume and the job description
Create a version under 500 characters that includes metrics and total years of experience
Cover Letters
Write a 150-word cover letter for the [job title] at [company] using my resume below
Draft a cover letter that mirrors the top five keywords in the job description
Show how my resume aligns with this job description in cover letter form
Informational + Formal Interviews
List 10 thoughtful questions for an informational interview in [industry]
Suggest strong questions to ask in an interview for a [job title] role
Generate sample CAR-structured answers to those questions
Post-Interview Review with Otter.AI
What keywords or themes did I focus on most?
How did I come across—clear, confident, nervous?
Which answers were strongest or weakest?
What key job requirements did I miss?
What should I clarify or expand on in my thank-you email?