Can Chatbots Help You Find a Job? Here Are 7 Things I Learned About ChatGPT Limitations

Stacy Garrels.
13 min readMar 3, 2023

As a marketer I’ve long been fascinated by chatbot technology. I’ve even worked with a handful of chatbot tools over the past few years to help write articles and optimize webpages.

From a content marketing perspective, chatbots aren’t bad and they’re getting better. Think of them as creative, robotic brainstormers who talk pretty, but can’t think critically. Ask them to solve problems and chatbots are, at best, elegant spewers of gobbledygook.

Yet what is job-hunting, if not elegantly spewing gobbledygook at scale as you cast a wide net in your bid for work that’s at least mildly satisfying?

And as a writer and digital marketer in a current state of joblessness, I wondered if chat AI could help me rapidly scale my job hunt. The hunt is a tedious, slow-moving process. I look for jobs and companies that appear appealing, do some research, and then craft cover letters with memorable closings (like “Yours in mediocrity”). It’s digital hand-to-hand combat. On repeat.

But what if I could automate part(s) of the process with chatbots? Could ChatGPT scour job openings for me, find relevant positions, and/or write riveting cover letters?

I had to find out.

Feeling hopeful, I put chat AI to the test. I spent several hours today putting the technology through its paces, asking ChatGPT to help with seven repetitive tasks that come with looking for work.

Here’s how ChatGPT fared.

7 Job search tasks I asked ChatGPT to do for me

1. Write a short bio

I asked ChatGPT to write a short bio selling me to prospective employers based on the link I shared to my LinkedIn profile.

Since its first output was a misfire, I asked the chatbot to produce two different versions.

Version 1

Meet Stacy Rebeck, the human dynamo with a pen (or keyboard, as the case may be). Stacy’s writing skills are so top-notch that even the most sophisticated AI chat bot couldn’t hold a candle to her word wizardry.

Sure, some people might say that chatbots are the future of content creation. But let’s be real here: do you really want your content to be created by a robot with no sense of humor or creativity? We didn’t think so.

Stacy is the real deal when it comes to writing. She’s got the kind of wit and charm that can’t be replicated by an algorithm. Whether she’s crafting a killer blog post, whipping up a catchy tagline, or crafting a compelling story, Stacy’s got the skills to pay the bills.

Plus, let’s be honest: if you hired an AI chat bot to write your content, you’d be missing out on all the fun of working with a real human being. Stacy’s got personality for days, and she’s not afraid to use it to make your content shine.

So if you’re looking for someone who can write better content than a soulless robot, look no further than Stacy Rebeck. She’s the human touch your content needs.

This version is repetitive, overly loquacious, and full of hacky wordplays.

Also, my name is wrong. LinkedIn allows users to display previous names or aliases including maiden names. Based on visual display, a human reader would have understood that Garrels is my current last name.

I asked ChatGPT to fix the bio, using the correct last name and to reference specific job skills and work experience.

When I asked the chatbot to give me a more accurate description, I was given a result even more inaccurate.

Version 2

Introducing Stacy Garrels, a writing wunderkind whose skills are so finely honed that she can outperform even the most advanced AI chat bot.

With a Bachelor’s Degree in English and a Master’s Degree in Communications, Stacy has the education and experience to back up her writing prowess. She’s worked as a freelance writer, copywriter, and content strategist for over a decade, and has a proven track record of delivering engaging, effective content to a wide range of clients.

Stacy’s specific skills include an ability to distill complex information into clear, concise language, a talent for crafting killer headlines and taglines, and a keen eye for detail that ensures her writing is always error-free.

But perhaps what really sets Stacy apart from the AI chat bots of the world is her creativity and personality. She’s not afraid to inject a little humor or personality into her writing, which makes it stand out from the dry, soulless content that machines churn out.

Stacy’s experience working with a variety of clients and industries has also given her a unique perspective and a broad knowledge base. Whether she’s writing for a tech startup or a non-profit organization, she’s able to quickly get up to speed on the subject matter and deliver content that resonates with the target audience.

So if you want content that’s written by a real human being with real skills and personality, look no further than Stacy Garrels. She’s the writing dynamo you’ve been searching for.

This second version also fails. The chatbot spelled “chat bots” wrong (both versions), referenced zero employers when several are clearly indicated on my profile, and cited a “Master’s Degree in Communications” that I do not possess.

Even when directed to a specific set of facts, Chat AI fails. A master’s degree is just a common, sounds-good attribute that Chat AI decided to make up.

Takeaway: ChatGPT cannot write your professional bio or work summary.

2. Write me a cover letter

This was the capability I was most excited to test: cover letter writing. Surely the powers of Chat AI can outclass a flawed human.

I asked ChatGPT to write a cover letter for me to apply for a “Content Writer” opening at a computer software company. I shared the specific job posting and my LinkedIn profile.

ChatGPT’s efforts are a sadly comical misfire.

Dear Hiring Manager,

I am excited to submit my application for the Content Marketing Specialist position at your organization. As an experienced writer and content strategist, I believe I would be an excellent fit for this role.

Throughout my career, I have honed my skills in writing, marketing, and strategy. With a Bachelor’s Degree in English and a Master’s Degree in Communications, I have a deep understanding of the nuances of language and the power of storytelling. I have worked as a freelance writer, copywriter, and content strategist for over a decade, and have developed a talent for crafting engaging, effective content that resonates with audiences.

In addition to my writing skills, I am also well-versed in marketing and strategy. I understand the importance of creating content that not only engages audiences, but also aligns with business objectives and drives results. I am adept at conducting research, analyzing data, and developing content strategies that meet the needs of both the audience and the organization.

Furthermore, I am a skilled collaborator who enjoys working with cross-functional teams to achieve shared goals. I have experience working with designers, developers, and other content creators to bring campaigns to life.

Finally, I am excited about the opportunity to work with an organization that is committed to making a positive impact in the world. I am passionate about creating content that inspires and educates, and I believe that this position would allow me to do just that.

Thank you for considering my application. I look forward to the opportunity to discuss my qualifications further.


Stacy Garrels

Again, Chat AI decided to upgrade my educational background. Beyond that, Chat AI didn’t reference the employer’s name, got the job title wrong, and didn’t address the needs and skills outlined in the description.

Takeaway: Chat AI cannot analyze and synthesize data (think like a human being) or write your cover letter.

3. Scour classified ads

Based on my LinkedIn profile and resume, I asked ChatGPT to find 20 open jobs for me on LinkedIn.

The 20 jobs that ChatGPT suggested I apply to sounded like they were related to my career field.

The job titles sound pretty good, filled with relevant keywords and interesting companies.

But I just did some research on LinkedIn and not one of these suggested jobs is real. Every single one is made-up.

Thinking that ChatGPT may need more explicit direction, or that my research skills were lacking, I asked it to provide me with links for all 20 of the job suggestions.

Here are the links to all 20 job listings on LinkedIn that align with your skills and experience:

1. Content Marketing Manager at Salesforce:

2. Senior Copywriter at Wunderman Thompson:

3. Digital Marketing Manager at Patagonia:

4. Social Media Manager at Nike:

5. Communications Manager at Microsoft:

6. Content Strategist at PayPal:

7. Marketing Communications Manager at IBM:

8. Content Marketing Specialist at Google:

9. Senior Copywriter at Airbnb:

10. Social Media Coordinator at Sephora:

11. Communications Specialist at Cisco:

12. Digital Content Creator at Adobe:

13. Marketing Communications Coordinator at Dell:

14. Content Writer at American Express:

15. Digital Marketing Coordinator at The Home Depot:

16. Marketing Copywriter at Amazon Web Services:

17. Communications Coordinator at Intel:

18. Content Marketing Coordinator at LinkedIn:

19. Digital Marketing Specialist at Verizon:

20. Social Media Strategist at Facebook:

Great there are links — except none of these links work. All of the links are completely unrelated to the preceding job titles.

ChatGPT told me that this webpage was for an open job at LinkedIn in content marketing. The page is for an unrelated, on-site job in Texas, over 1,200 miles from my location — and closed to new applications.

The job links are broken or take you to unavailable job postings at different companies. For example, I visited the link for the content marketing position at LinkedIn and found it was a job post for a Regional Sales Manager in Houston — and applications are no longer being accepted.

Takeaway: ChatGPT cannot analyze the job listings for you. If you ask for links to specific job listings, you will receive a list of useless drivel.

4. Write me a resume

I asked the chatbot to write a resume for me to apply for a marketing manager role based on my LinkedIn profile.

Nothing in the resume remotely resembles the LinkedIn page I referred the Chatbot to. It even invented a new address, phone number, and email address for me.

Stacy Rebeck

1234 Main Street | Minneapolis, MN 55401 | (555) 555–1234 |

Marketing Manager

Innovative marketing strategist with 7 years of experience in developing and executing successful marketing campaigns. Proven ability to manage teams, collaborate with stakeholders, and exceed business objectives. Passionate about driving revenue growth, customer engagement, and brand awareness.


Marketing Manager, XYZ Corporation | Minneapolis, MN | 2019 — Present

Manage a team of 5 marketing professionals to develop and execute digital marketing campaigns, resulting in a 30% increase in website traffic and a 25% increase in lead generation

Collaborate with sales teams to create targeted marketing content that aligns with sales goals and supports lead generation efforts

Lead the development and execution of email marketing campaigns that resulted in a 20% increase in open rates and a 15% increase in click-through rates

Develop and implement SEO strategies that increased organic search traffic by 40%

Manage the company’s social media accounts, resulting in a 50% increase in engagement and a 20% increase in followers

Marketing Specialist, ABC Corporation | Minneapolis, MN | 2016–2019

Managed the development and execution of marketing campaigns across multiple channels, resulting in a 15% increase in website traffic and a 10% increase in lead generation

Collaborated with product and sales teams to create product launch materials and sales collateral that supported business objectives

Coordinated the development and distribution of monthly newsletters, resulting in a 25% increase in engagement

Managed the company’s social media accounts, resulting in a 30% increase in followers


Bachelor of Science in Marketing, University of Minnesota | Minneapolis, MN | 2016


Marketing strategy development and execution

Team management and leadership

Digital marketing and advertising

Social media management and strategy

Content creation and management

Email marketing and automation

Search engine optimization (SEO)

Data analysis and reporting

Sales collaboration and support


Available upon request.

Except for implying I’m 29 years old, there’s nothing I like about the resume. I do possess some of the skills outlined, but that’s purely by coincidence. ChatGPT is writing what they think a marketing manager’s resume should sound like, and it’s drawing inaccurate inferences based on its limited understanding of my profile.

If I didn’t know how to structure a resume, I could draw inspiration from this format. But really, the chat AI output itself is utterly unusable.

Takeaway: Do not let chat AI write your resume, but you could use the basic template that it provides.

5. “Why were you laid off?”

Many job seekers fear this question and practice their measured response. I don’t find this question particularly scary or threatening (nine years was an awfully long run), but many people do.

So I asked ChatGPT for three good ways to respond to that question.

Example 1

“I was laid off due to a company-wide restructuring that resulted in a reduction in workforce. Although it was a difficult decision for the company to make, I understood the reasoning behind it and respected their decision. I took the opportunity to reflect on my skills and experience and have used this time to further develop my professional skills.”

Example 2

“My previous company was experiencing financial difficulties, which unfortunately resulted in a round of layoffs. I was part of the impacted team, but I appreciated the open communication from management about the situation. During my time off, I have been actively networking, seeking out professional development opportunities, and keeping up with industry trends.”

Example 3

“Due to the pandemic, my previous company faced significant business challenges, which resulted in a reduction in force. I was one of the impacted employees. Although the situation was difficult, I appreciate the opportunities that the layoff gave me to reflect on my career goals and pursue new avenues for professional growth.”

These answer are pretty good, but they sound canned, cliche, and rehearsed. You could borrow any of these examples and fare just fine. But if the employer asks you to “elaborate” on your response, your inability to think on your feet or speak like a human being will be revealed.

Takeaway: ChatGPT is effective at offering you elegant-sounding job cliches that meet the moment, but you will still have to think on your feet.

6. “What are your biggest weaknesses?”
Thanks for the Michael Scott meme.

The last time I was asked this question was during college. I was interviewing to be a part-time shoe sales associate at Herberger’s in Fargo, North Dakota. (Yes, I got the job.)

Many job hunters dread this question. ChatGPT suggests some decent talk-offs you can try. Here’s one of the examples that the chatbot recommends:

“One of my biggest weaknesses is that I tend to take on too much at once. I have learned to prioritize my workload and delegate tasks to others when necessary to ensure that everything is completed efficiently and effectively. Another weakness I have is public speaking, but I have been taking steps to improve this by attending public speaking workshops and practicing in front of colleagues.”

Takeaway: If you don’t know how to spin your biggest weakness, ChatGPT can help you find a way to eloquently excuse it.

7. Memorable ways to close a cover letter

I asked ChatGPT to share 10 memorable and original salutations you can use to close your cover letter, and the results were better than I had anticipated.

1. Looking forward to bringing my skills and enthusiasm to your team!

2. Thank you for considering my application. Let’s take the next steps together.

3. I’m excited about the opportunity to discuss how I can contribute to your company’s success.

4. I look forward to the chance to prove myself as a valuable asset to your organization.

5. Thank you for the opportunity to apply. I am eager to show you what I can bring to the table.

6. Here’s to a successful collaboration. Let’s make great things happen!

7. I’m passionate about the work your company does and would love to be a part of it.

8. I believe I can make a positive impact on your team, and I’m excited to explore this possibility with you.

9. If you’re looking for a creative, motivated problem solver, look no further.

10. Thank you for considering my application. I look forward to discussing my qualifications further in an interview.

This is where chat AI shines: ChatGPT excels at providing popular truisms and stock phrases.

Some of these suggestions are pretty good. While not especially memorable, these closings are professional, safe, and more creative than a single-word sign-off. (I myself have adopted a cheekier approach to closing cover letters in order to maintain brand consistency.)

Takeaway: ChatGPT can offer you some good ideas for how to close your cover letter.

Chat AI can’t find your next job

The bottom line is that chat AI can’t find your next job.

I’d be lying if I said I wasn’t relieved that robots can’t (yet) replace me, but I’m also disappointed. I wanted to offload some of my resume-writing, job-hunting chores. And with AI technology improving every day, I had thought chatbots could be (more) useful if I fed them enough data and explicit instruction.

But right now, chatbots don’t have the ability to analyze and synthesize the data that you provide, and then come up with original, fact-based content.

Still, chat AI isn’t completely without merit. If you need someone to write a very generic cover letter or other light marketing copy, ChatGPT is an excellent writing assistant.



Stacy Garrels.

“Confident in my ability to outshine mediocre people everywhere who have jobs they are not even qualified for.” Humor. Sarcasm. Ballsy copy. Meandering essays.