How I’d Use AI to Run a Smarter Job Search
I use AI in my own work. If I were looking for a job today, I’d use it there, too. But the first thing I’d give it would be one job posting and three accomplishments I could talk about in an interview. I’d ask it which of those accomplishments would matter to the person doing the hiring, and why.
After years in executive search, I can tell you that a polished résumé still leaves me with the same questions. What did you actually do? What was yours to own? What happened because of it? If I have to dig through two pages to find that out, you’ve made it harder for me to make your case.
A Threads post from @zephyrhq got me thinking about where AI can help at each stage of a search. Here’s how I’d use it.
1. Find out what a recruiter can actually see
When you know your own career inside out, it’s easy to assume a reader will connect the dots. “Oversaw operations” could mean you ran a five-person office or led a restructuring across six locations. Those are different stories. If the scale matters to the job, put it where someone can see it.
Try this prompt
Compare this job posting with my anonymized career summary. Identify the three responsibilities that appear most central to the role. For each one, show which example from my experience supports it, what I’ve left unclear, and what appears to be a genuine gap. Ask me a follow-up question when the evidence is thin.
A chatbot can compare what’s on the page. The employer may have priorities you’ll only learn from a conversation. Treat the comparison as a way to decide what to clarify and what to ask. For a fuller version of this exercise, see how to build a career intelligence system before you apply.
2. Build a list of employers you’d actually want to work for
I’d rather have five organizations I can explain my interest in than 50 names in a spreadsheet. Start with the work you want to do, the problems you know how to solve, and the conditions you need to make a move.
Try this prompt
Help me build a list of 10 organizations to research for [role or type of work]. My priorities are [mission or industry, geography, work arrangement, and scope]. For each organization, explain what makes it worth investigating, suggest one adjacent job title, and tell me what I should verify on its website before acting.
Keep your research list separate from your list of active openings. An organization can be a great fit even when it has nothing posted. When AI suggests a specific opening, check the employer’s careers page before you spend an hour tailoring your résumé.
3. Put your best evidence at the top of the application
If you’re moving from a corporation into a nonprofit, I’d want to know what carries over. Maybe you managed a tight budget, kept a team together through a merger, or persuaded people who didn’t report to you to support a change. Tell me what you did in terms the new employer will recognize. If you’ve never worked with a nonprofit board, be straightforward about it.
Try this prompt
Using only the experience and outcomes I provide, draft a short résumé summary and suggest which three accomplishments to feature for this role. Then outline a cover letter around why I want this particular job and one example that shows what I’d bring to it. Flag any claim I need to verify.
Read the draft aloud. If you wouldn’t say it in an interview, change it. If the tool turns “helped implement” into “led,” put your actual role back in.
4. Give someone a real reason to talk with you
If you’re going to ask someone for 15 minutes, give them a question worth answering. “I saw that your organization expanded its community programs. How did your team decide what to keep centralized as it grew?” gives the person something specific to respond to.
Try this prompt
Help me write a brief note to [person or role]. I’m reaching out because [one specific thing I verified about their work]. I’d like to ask [one question I genuinely want answered]. Give them the option to reply by email or talk for 15 minutes. Keep it in my voice.
If someone gives you their time, listen. You may learn something about the job you wouldn’t have known to ask in an interview.
5. Prepare an example you can defend
For a leadership role, I’d start with a decision you actually made. What did you know at the time? Who disagreed? What did you do next? If you’re changing fields and need a work sample, give yourself a small, fictional problem and show how you’d work through it. A prospective nonprofit COO might write a one-page memo on how they’d handle a midyear budget shortfall. The interesting part is what they’d ask before deciding what to cut.
Try this prompt
Help me design a one-page work sample for [role] using fictional or public information. Give me a realistic decision to make, two competing priorities, and three questions an interviewer could ask about my reasoning. Leave the decision and the writing to me.
You should be able to explain every choice in the sample. If you use it in an interview, say how you created it.
6. Figure out what you still need to know about the offer
If you’re considering an executive director role, for example, you may want to know who sets your first-year goals, what authority you’ll have to make staffing decisions, and what support you can expect from the board. Those answers can change how you feel about the job.
Try this prompt
Here’s a summary of the offer and what matters to me. Separate the terms the employer has confirmed from my assumptions and open questions. Help me choose the three questions that would most affect my decision. Draft a short reply that asks them plainly.
Before you use any of these prompts, take a minute to decide what the tool actually needs. It can work with an anonymized résumé, a fictional scenario, or a summary of offer terms. Leave out your home address, references’ contact details, confidential employer information, and the signed offer letter. You can give it enough context to help without handing over your whole file.
If you try one prompt this week, make it the first one. Pick a job you’d genuinely take and see whether the strongest reason to interview you is visible on the page. If it’s buried halfway down your résumé, you already know what to fix.
If you run a nonprofit team, read What Nicolas Rodes Gets Right About ChatGPT for Nonprofits for how I’d use AI drafts at work without losing track of who checks them.