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Talent Tip #170: 5 DOs and DON’Ts of Using AI to Help With Your Job Search

February 18, 2025

Do you remember when mobile phones came on the scene? (Insert blank stare from Gen Z. Just trust me, guys. It was a cool time to be alive.)

I was a kid when my dad got one in his new car. I thought for sure we were rolling in dough. Nevermind the phone itself was as big as a box of Rice Krispies and had a curly cord tethering it to the console.

Immediately, I knew it was going to change our lives. We could make calls from anywhere! No more being stuck at home waiting for the phone to ring.

But I quickly learned there were limitations of this family-size box of crisped rice. I once gave the number to a cute boy and he called when I wasn’t in the car….but my dad was. I never fully understood how the conversation went down, but I strongly suspect my father threatened him with bodily harm if he ever called again because it cost my dad $14 just to say hello. Lesson learned: share the mobile number wisely and instruct callers to hang up immediately if I don’t answer.

And here we are with AI.

Everyone is abuzz with excitement about how AI is going to change the world. Yet, there are plenty of people using AI in all of the wrong ways, especially when it comes to job seeking in the liberty movement.

So here are 5 DOs and DON’Ts to keep you on the right path!

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DO: Use AI to help with and proofread your cover letter
DON’T: Use AI to write your cover letter

I know what you’re thinking: writing cover letters can feel like being stuck in traffic with G.I. issues (downright unpleasant). But if you’re really excited about a job, you shouldn’t feel the need to take the next exit and head for the nearest Flying J.

Trust me when I tell you it’s not hard to spot an AI-written cover letter. They come across as impersonal, use canned language, and never fail to fail to grab my attention.

They say the best cover letters tell a story. And AI simply cannot write your story.

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DO: Use AI to help track your job applications
DON’T: Use AI to apply for jobs for you.

Having an AI assistant apply for jobs on your behalf might work if you’re aiming for a job as a barista, data entry specialist, or sales rep, but if you’re trying to land a job in the liberty movement, job bots aren’t going to be of much help.

Most free-market jobs require the level of thought the job bot simply isn’t capable of yet (God help us when it gets there).

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DO: Use AI to help you prep for interviews.
DON’T: Use AI to write your answers for you.

Using a simple prompt such as this can yield some great potential interview questions:

I’m going to interview for this job: [insert link to job description here]. What interview questions should I expect from the hiring manager?

The questions you get will be somewhat general in nature, but I suspect you will find all of them at least somewhat useful. Of course, AI doesn’t have a personal relationship with the hiring manager of any given nonprofit, so these suggestions have limitations. But this is a great way to get your brain thinking about the topics you’ll likely encounter during the interview.

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DO: Use AI to help you research aligned nonprofits working on issues you care about.
DON’T: Use AI as a substitute for tapping into your network.

Do you know what you’re passionate about but aren’t sure where to start? Using a simple prompt like this can point you in the right direction:

I am a conservative/classical liberal/libertarian who cares deeply about education reform. What organizations should I consider working for?

You’ll probably find a good list of organizations this way, but don’t stop there!

Be sure to ask your network for ideas. (Remember, the real-life humans you’ve built actual relationships with over the years? Yeah, those people.) Word of mouth is still our biggest source of talent. So, take advantage of it!

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DO: Use AI to help you frame your experience on your résumé
DON’T: Let AI turn your résumé into a mind-numbing list of generic buzzwords and hollow catch-phrases

AI might know how to create a résumé with all of the right jargon, and that’s great if you’re applying for a job in customer service.

But in the liberty movement, humans are still doing the hiring and humans tend to get annoyed with results-driven thought leaders managing cross-functional tiger teams leveraging synergy and outside-the-box thinking to move the needle on mission-critical projects.

Just….don’t.

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When I originally sat down to write this article, I thought it was only fair to give Chatty (my affectionate nickname for ChatGPT) a chance to write it first. She spits out a quite serviceable, if uninspiring, article in mere moments. I sat on it for weeks and finally decided it was a hunk of rubbish and completely unusable. Sorry, Chatty. There are some things humans can still do better.

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About Us

Claire Kittle Dixon
Executive Director

Claire runs the day-to-day operations of Talent Market, manages searches for clients, and oversees the organization’s fundraising communications, technology, administration, and cat-herding efforts…
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Katy Gambella
Director of Outreach

Katy oversees Talent Market’s outreach to young professionals and manages the outreach team. She also manages searches and executes outreach directly herself…
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Stephanie Keaveney
Senior Manager of Outreach
Stephanie splits her time between managing talent searches for free-market nonprofits, maintaing Talent Market’s social media presence, and engaging in outreach to young professionals interested in liberty-oriented careers…
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Bailey Drouant
Project Manager
Bailey assists free-market nonprofits with their hiring needs by helping them manage the search process from start to finish…
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Savannah Rupp
Project Manager
Savannah channels her expertise to manage searches for free-market nonprofits, ensuring they find the perfect match to drive their missions forward. She also supports Talent Market’s…
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Wait, You’re a Nonprofit?

Talent Market is a nonprofit. We’ll wait here while that sinks in. We know it’s a crazy concept, but it’s been working like a charm since 2009.

Talent Market’s mission is to promote liberty by providing talent for critical roles within the free-market nonprofit sector.

We provide consulting and recruiting services at no cost to 501(c)3 nonprofit organizations that clearly and directly focus on advancing the principles of economic freedom, free enterprise, free trade, free speech, property rights, rule of law, and limited regulation. (We do not work with political organizations, organizations with mission statements that do not clearly advance free-market principles, organizations that focus on social issues, or organizations that have a focus outside of the United States. We are not a job board. ) 

Talent Market believes that the road to prosperity is paved with freedom and that the success of our movement hinges on the talent that will take us there.

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