Mastering the Hunt: 10 ChatGPT Strategies for Job Seekers

May 19, 2023
Kirk Clyne & Suzanne Reeves
A detailed illustration of a mountain view from a wilderness camp. A map, compass, laptop and other gear are spread around a wooden deck, suggesting a home base of an adventurous hiker.A detailed illustration of a mountain view from a wilderness camp. A map, compass, laptop and other gear are spread around a wooden deck, suggesting a home base of an adventurous hiker.

Mastering the Hunt: 10 ChatGPT Strategies for Job Seekers

Hello fabulous designers!

A big welcome to all our new subscribers. We’re grateful to have you with our growing community.

We talk a lot these days with designers about whether the robots are going to change our jobs or just take our jobs.

(They are certainly messing with a lot of other people’s jobs in adjacent industries. Copywriters are losing their jobs to clients with ChatGPT on the daily. Even the feverishly optimistic Forbes took notice. And 3D modellers are becoming prompt-writers instead, whether they like it or not.)

But, in this post, we’re going to flip the script and talk about how the robots can help get you a job.

For those of you we’ve chatted with who are (willingly or unwillingly) on the hunt for a new job or who are seriously thinking about it — you touched our hearts. We’re thinking about you and sending lots of good energy your way for the journey.

This post is for you. 💗


ChatGPT as Career Coach & Navigator

When it comes to finding a job in 2023, ChatGPT is a secret weapon.

People think of ChatGPT primarily as a copywriter — and it is: one that can help you craft resumes, cover letters and networking emails. 

But it’s also a research assistant and a career coach.

Whether you’re just starting out, or making a change, here are a few different ways ChatGPT can help you out at various stages of the job searching process.

Lookin’ Around

Not sure where you want to work, or what you can even do? 

Tell ChatGPT all about yourself. Share your education, experience and interests; your values; your short- and long-term career goals; the things you love — and hate — doing. 

Then ask it for a list of suitable jobs for someone like you. Crazy, right?

A screenshot of the ChatGPT interface. The user has stated they love design but have social anxiety, and ask how they might make a living while avoiding people. ChatGPT responds with a list of roles that begins with Freelance Designer and Remote Designer.
Share it all. ChatGPT doesn't judge!

If one of those jobs sounds appealing, dig in with more questions: what skills does it require, how does one get started, what sort of experience matters most — and who are the top companies that offer jobs like this?

Company Research

Sure, you’ll visit their website, and creep their socials. 

But it’s 2023: don’t Google them and hunt through web pages of other web pages about them.

In a few seconds, ChatGPT will give you a few paragraphs of background, summarized neatly on a silver platter.

A screenshot of the ChatGPT interface. The user has asked to be told about the company behind the design tool Figma. ChatGPT reponds with several paragraphs of text, detail the year it was founded, the founders' names, that its HQ is in San Francisco and more.
You could compile this info from a bunch of Google searches, but why would you?

What else do you want to know? You might ask who their primary competitors are, or what sets this organization apart in the industry, or how they got started. 

What does the company value? What are the founders like? What’s their reputation among the staff? 

If you know who’s in an upcoming job interview, ask for a biography on them, too. Maybe you’ve even got something in common that you can find a way to bring up in the interview, Sneaky Pants.

Just remember to vet what ChatGPT tells you, as it can get a bit creative with the facts.

Job Searching

Job searching is never exactly fun, but ChatGPT can help make your efforts more effective. 

Ask which websites post jobs in your particular industry, or for your specific kind of role. (For the most up-to-date results, you’ll need ChatGPT Plus and the WebPilot plugin so it can search the internet.)

A screenshot of the ChatGPT interface. The user has asked where UX jobs are posted online, and ChatGPT has provided a list of site with short descriptions that includes LinkedIn, Indeed and Glassdoor.
It’s like Googling, but way better

Ask it for the best search terms to use for your type of roles, and for tips on how to make searching more effective when using a specific service like Google or LinkedIn.

In fact, remember that no single answer from ChatGPT is ever the final answer. If it says Dribbble is a good place to look, but you aren’t familiar with using Dribbble that way, just ask it more questions! 

Cover Letters

There are many ways to take advantage of ChatGPT to improve your cover letters.

You can ask it for a good format that you can follow, one that ensures you're ticking all the right boxes.

A screenshot of the ChatGPT interface. The user has asked what the best format for a cover letter is, and ChatGPT has reponded with a list of items, and details about each one, including Header, Salutation, Opening Paragraph and others.
If you prefer to DIY, just ask for a basic format and do the rest yourself

Or you can give it a list of bullets, or thought-starters, and ask it to flesh it out into a letter.

You can feed it a draft letter of your own, and ask for revisions. 

Or get crafty: copy and paste the job description, and your resume, and ask it to write a cover letter for that job description that relies on the resume for evidence of experience.

A screenshot of the ChatGPT interface. The user has asked whether ChatGPT can write a cover letter based on the user's resume and a job posting. ChatGPT replies that it can help create a customized cover letter that highlights their qualifications and aligns with the role.
ChatGPT is always eager to help

Of course, for cover letters and emails, you’ll want to ensure they still sound like you and have a personal tone, so be sure to edit and revise (not just copy and paste).


As with cover letters, ChatGPT can improve your resume in a number of ways.

It can create a draft from some bullets or notes; it can edit an existing draft, or suggest ways to improve the format or content. 

You can also use it to rewrite work experience sections piece by piece. 

A screenshot of the ChatGPT interface. The user has pasted a single line from their resume and asked ChatGPT how they could improve it. ChatGPT has responded with a list of detailed suggestions, such as quantifying any achievements, highlghting any specializations or unique curricula, showcasing innovative teaching methods, and more.
This is good advice — it’s not generic or general, but specific to the role

This is good advice — it’s not generic or general, but specific to the role

LinkedIn Bio

Feed ChatGPT your resume and ask it for a bio that includes the most important skills and highlights a few accomplishments.

Tell it to make it SEO-friendly, while you’re at it.

If there’s a character limit, tell it that too.

You can do the same for all of your social platforms. Ask it to vary the focus or tone of voice to make it more appropriate for how you use Twitter vs. Instagram vs. Slack.


Not sure how to write that cold email or unanticipated LinkedIn message?

Tell ChatGPT who you’re writing to and why. Explain that you don’t want to sound needy or desperate — or whatever your concerns are — and see what it says. 

If you don’t like the suggestion, just tell it why, and ask it to try again. You might be amazed at what the two of you can accomplish with just a little collaboration.

You can also get ChatGPT’s help as a networking coach: Ask it how to make a good impression at an upcoming event, or how to move past your nerves. Ask it the best ways to follow up with folks after the event, too — and what to say.

Brushing Up

Do you expect to be asked interview questions where you’ll need to demonstrate expertise in a particular area? Ask ChatGPT for a refresher.

Sometimes, we get so used to a discipline or field of expertise that we forget how to step back and talk about it objectively.

Want to know more? Just ask. You can go deep or stay on the surface.

A screenshot of the ChatGPT interface. The user has asked about the basics of adult learning theory. ChatGPT has replied a short summary, then a list of key concepts with short explanations, including Self-Directed Learning, Prior Experience, and Goal-oriented Learning.
Want to know more? Just ask. You can go deep or stay on the surface.

Hearing the “101” on a topic can remind us of the big points we’ll want to nail when sharing our knowledge.

Interview Practice

Wondering what they’re going to ask you about in the job interview for that new Senior Product Designer role over at ACME Digital?

Ask ChatGPT for a list of 20 common interview questions for that specific role, and practice answering them out loud.

Better still, you can literally copy-and-paste the entire job posting into ChatGPT, and ask it for sample interview questions based on the posting itself. Then go a step further and ask ChatGPT for an example of a good answer for each one. 

But why stop there? Just ask ChatGPT to role-play the interview with you. (Seriously.)

Heck, you can even play the interviewer next time: ask ChatGPT some tough questions, and see how it handles the hot seat.


Having any kind of starting point for The Money Discussion can be invaluable.

ChatGPT's information isn’t entirely up to date, but you can still get its take on the expected salary for a given role. (Or, if you’re using ChatGPT Plus, add the WebPilot plugin and have it search the internet for the relevant information.)

Or get specific, and remind it of your experience, the job description, and the company, and see what salary it thinks you could command.

Or ask it to ask you a series of questions to determine an ideal salary.

A detailed illustration of a mountain view from a wilderness camp. A map, camera, thermos and other gear are spread around, suggesting a break taken mid-hike.
Job hunting isn’t easy. Take a break when you feel overwhelmed. Try touching a tree.

Follow Up Emails

After every interview, it’s important to send a formal note to thank the interviewer for their time. 

Ask ChatGPT for a draft. Make it personal by telling it how you feel about the job after the interview, or what you’re looking forward to. You want something personal, but not gushy or overly-excited.

If you don’t hear back after a couple weeks and want to ping the company for a follow-up, ChatGPT can help you write that cold email, too.


The Last Word

The job search can be made more painless with ChatGPT in your corner.

From writing emails, to practising interviews, to pitching to investors, you’ve got a super-experienced career coach you can rely on at every step.

Of course, your new partnership doesn't have to stop once you land a job. After all, you never know when you might need help editing an email…

Who says robots can’t be empathetic?

Until next week,


A creative leader, designer, teacher and artist with a 20-year career, Kirk Clyne is well-positioned to help designers master new technologies and build exceptional careers in the creative industry. He co-founded Art & Science, a digital design agency that landed on the Globe & Mail’s Growth 400 list, and spent the better part of a decade teaching digital design courses at San Francisco State University and the Academy of Art College.

Suzanne is an experienced entrepreneur and design leader fascinated by AI's transformative potential. She's run her own successful design firm for the past 10 years, built and mentored design teams, and has degrees in Psychology and Fine Art. Passionate about nurturing the next generation of 'design unicorns', she helps teams and individuals leverage strategy, design, and building skills, believing AI tools can exponentially expand our creative potential.