Jeremy Schifeling on Using Generative AI in Your Career Search

Leveraging Generative AI in Your Career Search with Jeremy Schifeling

Jeremy Schifeling, founder of The Job Insiders and author of Career Coach GPT and Linked: Conquer LinkedIn, Get Your Dream Job, Own Your Future shares his insights on how job seekers can leverage generative AI tools like ChatGPT in the job search process.

Jeremy and I have known each other for seven years and recently co-presented a session at the Career Services Employer Alliance Global Conference on how graduate business school career services can leverage generative AI in their work.

In this episode, Jeremy returns for a second conversation to discuss how business school students, job seekers, and professionals can use AI to tailor their resumes, cover letters, and interview prep, while staying authentic in their communication. Listen to my first conversation with Jeremy about his book, Linked, from May 2022.

Key Takeaways:

1. Get Hands-On with Generative AI: Jeremy emphasizes that AI tools like ChatGPT, Anthropic's Claude, Gemini and Copilot are easy to use, even for non-technical individuals. By interacting with these platforms, job seekers can quickly familiarize themselves with their capabilities—whether for refining resumes, helping to draft cover letters, or even brainstorming career paths based on personality tests like Myers-Briggs or CliftonStrengths.
2. Crafting Effective Prompts: Jeremy and talk about the importance of specificity in AI prompts as well as using meta prompting techniques. While a generic prompt like "write a cover letter" might yield basic results, being more precise—such as asking for insights into missing keywords or requesting tailored interview questions based on a job description—will lead to better outcomes. He also encourages users to iteratively refine outputs, ensuring the final result feels authentic and personalized.
3. Beyond Job Searching—Building Long-Term Skills: The skills you develop using generative AI tools can extend to developing AI literacy that is rapidly becoming a key asset in many industries. Understanding how to harness these tools for tasks like data analysis or marketing can make professionals more competitive in the long run.

Practical AI Tools and Strategies:

• Role-Playing Interviews with ChatGPT: Use AI to simulate job interviews, ask follow-up questions, and even offer feedback on your responses, preparing you for tough, real-life interview scenarios.
• Mining Job Descriptions for Insights: Paste multiple job descriptions into AI tools to uncover common skills, which can help you craft a LinkedIn profile that resonates across different career paths.
• Maintaining Authenticity: While AI can help draft resumes and cover letters, Jeremy advises against over-reliance on AI-generated content. Ensuring your voice comes through is essential, as recruiters are becoming savvy to AI-generated applications. Craft prompts that include your first drafts, or career highlights, feed your final drafts back into the chat so the bot can learn from the changes you make.

Resources Mentioned:

• ChatGPT
• Books by Jeremy Schifeling:
• Career Coach GPT
• Linked: Conquer LinkedIn, Get Your Dream Job, Own Your Future
• Ethan Mollick’s book "