Utilizing AI to Draft Your Job Applications

Megh Gautam, MS ‘12 and Mehul Patel, MS ‘99 established a friendship back in 2011, when Megh took full advantage of the Stanford Alumni Mentoring system to find a product management mentor and was paired with Mehul. They hosted an informative session covering this emerging use case of AI.

First - think about your personalized content:

• You have to think of job hunting as spear fishing, not net fishing. You need to  work on effectiveness before you can be efficient.
• Think about your passions. Your next career moves are generally as random as they are planned, because industries, markets and personal interests change.
• You should tailor your applications to each role and company.

Now - start using AI:

• Effectiveness and efficiency come together in the prompt. The prompt is everything.
• Use the context window.
• For a cover letter, or personalized email, Megh and Mehul have found that Claude is a better tool than Chat GPT.
• Are your prompts coming back with results that are too literal? 
  • Tell the AI to be succinct: this forces it to use fewer words, so it won’t just copy big blocks. 
  • Tell the AI to summarize: it won’t just copy big blocks verbatim. 
    1. In Chat GPT, you do this in the “how would you like Chat GPT to respond” box.
    2. In claude, you can send a bunch of documents along with your prompt, so it can match your style. You still have to quality control it.
• Did your prompt create an hallucination? (ie, did the AI add a bunch of random stuff?)
  • Tell the AI what *not* to drop.
• Adding more key words doesn’t necessarily help - you need to know your target audience to know what the recruiter or hiring manager will be looking for.
  • In advance of your applications, you should be having conversations with people who are hiring for the jobs you’re interested in, to research how companies in the field are conducting their hiring.
    1. You need a LinkedIn profile to help with this - people are more likely to positively respond to you if they can see who you are and what you’ve already been doing.
    2. Connect with people through LinkedIn, and/or Stanford Alumni Mentoring, unless you already have an address for them. Be specific when you contact them, with a clear ask. Don’t use a generic “can I pick your brains”, unless that is immediately followed with “about this specific topic”.
• You can’t lead the AI in a bunch of different directions and then be surprised if it doesn’t give you what you want! Use different threads for different industries that you’re targeting, or even a new thread for each company.
  • Tell the AI about the company you’re targeting, as well as the job. Use things like the ‘about’ page.
• Time saving efficiencies can be gained by feeding your template to the AI, and/or giving examples of resumes that you like, and then the job description.
• Remember there is only so much juice that you can squeeze from a resume.

Using AI in interview prep, and knowing its limits:

• Watch mock interviews on YouTube.
• Give the role description, company info and your resume, and ask the AI to list some likely interview questions.
  • Practice these the AI voice mode when doing things like driving.
  • But there is still nothing better than the human interaction, and communication is a requirement in every job - so also practice with your friends, classmates, others.
• Interviewers will be looking for teachability and connection. Interviews are a collaborative exercise. Be prepared for clarifying questions (in both directions).
• Know your answers to the classics - why us? Why this job? Why did you move from one job to the next?
• Companies are looking for people to join existing teams - how you fit is key. AI cannot help with this.
• Companies are hiring for potential. Be ready to explain why you’re a fit for the company and the role.

And finally, a general AI tip for once you’re in the workplace:

• Keep separate AI threads for different things, for example, one thread for things where you need to be succinct, such as memos to your supervisor or other leaders. Use a different thread for things that will have a different style, such as LinkedIn posts.