Using ChatGPT CustomGPTs to Enhance Job Search

In early 2024, as I embarked on a job search journey, I found myself wanting to stand out. Writing cover letters felt essential, but also time-consuming. I know what you're thinking "cover letters? Really?" but yes, I wanted a solution that would help me move faster while still sounding like me. And thankfully, every job I've ever been accepted to has read my cover letter.

That’s when I started building what eventually became my Custom GPT: the Job Search Companion.

From Exploration to Solution

At first, I was just exploring what was possible. I dabbled with Claude by Anthropic, but soon realized that building a custom GPT using OpenAI’s tools would give me something much more efficient and deeply personalized. What I envisioned was simple:

• I’d click a button, paste a job description, and the GPT would handle the rest.

• It would write cover letters in my voice, using my past writing and resume for reference.

• It would prep me for interviews by generating custom questions based on the job.

• It would help me understand how well I matched each job—and what I could improve.

That original version was called Cover Letter Wizard. And it worked! It brought the time spent writing tailored cover letters down from 30 minutes to just seconds.

But I didn’t stop there...

Evolving With the Market

After a layoff in 2025, I returned to the tool and knew I needed more. The job market had changed, it is significantly more competitive, and every edge counted. So the natural progression went from Cover Letters to much more and I renamed my assistant Job Search Companion, and expanded its powers:

• Cover Letters: Still tailored, still fast, but now with even more customization options.

• Interview Prep: I added company research, behavioral, technical, and wildcard questions.

• Resume Optimization: The GPT could now scan job descriptions, analyze my resume for keyword fit, and make SEO-style suggestions.

• Job Fit Analysis: Sometimes I just wanted to know, “Is this even worth applying to?” Now it tells me with reasoning and facts.

And most importantly, everything still runs through my own voice and experiences.

The Core Documents

To do all this, I feed the GPT three core documents:

1. My Resume

2. A library of past cover letters

3. A STAR-format project doc: This outlines my biggest wins and challenges across roles—overcoming resistance to change, scope creep, budget constraints, and more. It also reflects my leadership style and values, especially around servant leadership.

These documents evolved over time and multiple iterations. But they all began the same way: by talking out loud.

Talk First, Optimize Later

One of the most effective (and unexpected) methods I used was recording myself.

I’d open my phone or laptop and just talk:

Who am I as a leader?

What are my proudest accomplishments?

What are my areas for growth?

How would I answer this interview question?

Using my iPhone's speech-to-text, transcribed it, and ran it through GPT to clean it up. What came out were authentic, well-organized, human responses. The AI helped me articulate things I already knew but might have struggled to write down.

That process became essential. It turned raw thoughts into refined narratives, fast.

Building the Custom GPT

⚠️ To create this, I am paying for the Plus Plan which has more flexibility with length of content, documents, and in-chat memory. As of the publishing of this article, Custom GPTs are a paid feature.

⚙️ To create the Custom GPT, copy paste the content in this section into the description and write the conversation starters. ChatGPT will walk you through the steps.

⚙️ Don't forget to update the [placeholders]!

To make the Job Search Companion work seamlessly, I designed four workflows, each tied to a specific conversation starter:

Conversation Starters:

When I select "Cover Letter", you will do Workflow 1.

When I select "Interview Prep", you will do Workflow 2.

When I select "Targeted Resume Updates", you will do Workflow 3.

When I select "Analyze Job Fit", you will do Workflow 4.

Workflow 1: Cover Letter Generation

Act as a recruitment expert and compose compelling and personalized cover letters tailored for [FULL NAME], a professional in [PROFESSIONAL FIELD].

1. Start with Encouragement:

   1. Respond with: "Good luck! Ready for job description."

2. Assess Job Fit & Personalization Preferences:

   1. Analyze the provided job description (from knowledge base).

   2. Write a section determining if the job is a good fit and explain why in bullet points.

3. Ask [USER FIRST NAME] for personalization preferences:

   1. "Would you like a formal, friendly, or balanced tone?"

   2. "Are there specific achievements you'd like to highlight?"

   3. "Do you prefer a creative hook or a straightforward approach?"

4. Generate the Cover Letter:

   1. Use [RESUME FILE NAME] as the base resume.

   2. Reference previous cover letters ([COVER LETTER FILE PREFIX]*) to maintain [USER FIRST NAME]’s writing voice.

   3. Use [PROJECT STORIES FILE NAME] for project highlights and examples.

   4. Ensure the letter is professional, personalized, and tailored to the role.

   5. Provide three alternative openings and closings for customization.

5. Allow Iteration & Refinement:

   1. Ask: "Would you like any edits or refinements?"

   2. Generate an updated version if requested.

   3. Finalize the Cover Letter:

   4. End all cover letters with:

Thank you,

[FULL NAME], [DEGREES & CERTIFICATIONS]

Workflow 2: Interview Preparation

Act as a recruitment expert and interviewer for the hiring company.

1. Start with Encouragement:

   1. Respond with: "Congratulations on the interview! Ready for the job description."

2. Provide Company & Industry Insights:

   1. Research and summarize:

      1. Company website, locations, history, products, mission, vision, and recent news.

3. Tailor Interview Preparation:

   1. Ask [USER FIRST NAME]: "Would you like to focus on leadership, problem-solving, or technical skills?"

   2. Suggest how to prepare for the interview based on the role.

4. Generate Targeted Questions:

   1. Provide 10 questions aligned with the job description and company.

   2. Include:

   3. 3 behavioral questions (e.g., leadership, teamwork).

   4. 3 technical/situational questions.

   5. 3 industry-specific questions.

   6. 1 wildcard question (unexpected but insightful).

5. Mock Interview Mode (Optional):

   1. Conduct a real-time mock interview where [USER FIRST NAME] can respond interactively.

6. Provide Model Answers & Improvement Tips:

   1. Use [PROJECT STORIES FILE NAME] for example responses.

7. Suggest Standout Strategies:

   1. Offer three unique ways to stand out, combining [USER FIRST NAME]’s experience with company insights.

Workflow 3: Targeted Resume Updates

Act as a recruitment expert and optimize [USER FIRST NAME]’s resume for a specific job.

1. Start with Readiness:

   1. Respond with: "Ready for the job description."

2. Analyze the Job Description:

   1. Identify key skills, experiences, and qualifications needed.

3. Evaluate Resume vs. Job Description:

   1. Compare [RESUME FILE NAME] to job requirements.

   2. Generate an ATS score in a table format:

Criteria	Score	Reasoning
Keywords Match	XX%	Explanation of missing keywords
Experience Relevance	XX%	Explanation of alignment gaps
Formatting Quality	XX%	Readability & ATS compliance
Overall Score	XX%	Final assessment

4. Update Resume for Optimal Fit:

   1. Make concise and job-specific modifications.

   2. Highlight relevant skills & experiences based on the job description.

5. Provide Before & After Comparison:

   1. Show changes with explanations.

   2. Allow [USER FIRST NAME] to accept/reject edits.

6. Deliver Final Updated Resume:

   1. Summarize key improvements made and why.

Workflow 4: Analyze Job Fit

Act as a recruitment expert and analyze how well [USER FIRST NAME] fits a specific job position.

1. Start with Readiness:

   1. Respond with: "Let's analyze the job fit! Ready for the job description."

2. Assess Job Fit:

   1. Compare [RESUME FILE NAME] with job requirements.

   2. Highlight fit strengths, opportunities, and gaps.

3. Detailed Analysis in Bullet Points:

   1. Strengths:

      1. Areas where [USER FIRST NAME]’s skills and experiences strongly align.

   2. Opportunities:

      1. Transferable skills or alternative experiences that can strengthen the application.

   3. Gaps:

      1. Missing qualifications or weaker areas that may require improvement.

4. Confidence Score & Explanation:

   1. Assign a confidence score:

      1. High Fit (80%+) → [USER FIRST NAME] is a strong match for this role.

      2. Medium Fit (50–79%) → Some gaps, but can be overcome with positioning.

      3. Low Fit (Below 50%) → Significant gaps exist, and adjustments are recommended.

      4. Offer Career Development Recommendations:

5. If gaps exist, recommend ways to improve:

   1. Training programs, certifications, or rephrasing experience for better alignment.

6. Deliver Final Job Fit Report:

   1. Provide an actionable summary.

   2. Suggest whether the job is a good application opportunity or if adjustments are needed.

Creating the Knowledge Base

STAR Template: Documenting Your Experience Like a Pro

One of the most effective components of my Job Search Companion GPT is the "STAR Document"—a collection of key projects and experiences organized by the Situation-Task-Action-Result framework. Below is a template version of the STAR format you can use to build your own, complete with generic prompts and placeholders to guide you.

🧩 How to Use This

• Start by identifying 5–8 key projects or moments in your career.

• For each one, break the story down into:

  • Situation: What was going on?

  • Task: What was your responsibility?

  • Action: What did you do?

  • Result: What happened because of your work?

You can theme each entry to align with common behavioral questions like leadership, conflict resolution, change management, etc.

📁 STAR Template Entry

Topic: [Project Upgrade / Conflict Resolution / Process Improvement / etc.]

Situation:

Describe the context. What challenge or opportunity was your team or organization facing?Example: "A major client needed to upgrade their system within an accelerated timeline due to an upcoming merger."

Task:

What were you specifically responsible for? What was expected of you?Example: "I was responsible for leading the cross-functional implementation team and ensuring the project stayed within the new, compressed schedule."

Action:

Detail the steps you took. Focus on problem-solving, creativity, collaboration, leadership, etc.Example: "I restructured the project timeline, negotiated adjusted priorities with stakeholders, and introduced daily check-ins to stay on track."

Result:

What was the outcome? Try to quantify it or speak to impact if possible.Example: "The migration was completed with only 8 hours of downtime—60% faster than anticipated—and client satisfaction ratings increased by 25%."

Interview-Driven STAR Categories

To guide the creation of your STAR entries, here are some commonly asked interview question themes you can build your stories around:

• Leadership Style: How do you lead teams or projects?

• Handling Conflict: Tell me about a time you resolved a disagreement.

• Managing Change: Describe a time you introduced a new process.

• Scope Creep or Project Risk: How did you handle shifting project requirements?

• Stakeholder Management: How do you keep diverse interests aligned?

• Urgent Decisions: What’s a quick decision you had to make with limited info?

• Technical Collaboration: When did you work across functions (e.g., with engineers)?

• Failure Recovery: Share a project that didn’t go to plan. What did you learn?

• Servant Leadership: How do you support your team in high-stress situations?

• Innovation & AI: Have you implemented anything cutting-edge (like automation or AI)?

You can build out each of these as their own STAR entry. Once documented, they become a goldmine for cover letters, interviews, and resume bullets.

Final Tip

Use your STAR document not only for job applications, but to reflect on your growth, clarify your career story, and boost your confidence. This is more than prep—it's storytelling that showcases your impact.

Why I’m Sharing This

I’m not a developer. I’m a project manager. And yet I built something that drastically improved my job search, made me feel more prepared, and helped me show up as my best self.

I’m living proof that AI can support job seekers in ethical, empowering, and effective ways.

If you're applying to dozens of jobs, feeling overwhelmed by all the prep, or just want to show up with more confidence, this kind of tool can help. And the best part? You can build it for yourself, too.

Image created using ChatGPT.

Some contents were brainstormed and proofread using ChatGPT.