A Step By Step Guide to Tailoring Your Resume With AI

November 1, 2026

In today's hiring world, your resume is no longer a one-size-fits-all document. It's both expected and essential for your resume to be tailored to each role you apply to. But when you're applying to job after job on a weekly or even daily basis, making customizations gets tedious, resulting in you wanting to cut corners where you absolutely shouldn't. This is where AI comes in handy. Used correctly, it can save you hours of work while helping your application rise above the noise. But used carelessly, it can create a weak resume that gets dismissed as "AI slop". Let's avoid that and walk through the best way to use LLMs to your professional advantage. 

Step 1 – Upload your current resume (make sure it’s up to date) and include the following prompt: 

“I’m applying for a job (job posting pasted at the bottom) and I want you to tailor my resume to the job posting by highlighting my relevant experience, improving any formatting, and correcting any spelling or grammar errors you find. Highlight any changes you’ve made that may not be supported by the resume I provided. [Pasted text of job posting goes here]” 

Why this works: Allowing your agent to review your resume against the job posting will allow you to quickly surface the skills and experience that are relevant to the job so that hiring managers see the most relevant information about you first. If you are actively applying for or submitting your resume for many roles, the time it takes to edit your resume for every position can be prohibitive. Using AI prompts to reshuffle or resurface the right information can help prevent an errant dismissal by a hiring manager who is reviewing resumes quickly. 

Note that many job posting links end up being unreadable to AI agents due to gating or formatting issues. If you copy/paste the job details into the chat the first time, you’ll save yourself delays and potentially wasted tokens. As we know, LLMs can hallucinate, so make sure that you ask it to highlight any updates it made that may have been more art than science. Always carefully double check what it’s done. 

Step 2 – Review and iterate, include the following prompt: 

“Give me a list of skills and how they are commonly worded, that are most important for someone in this role.” 

Why this works: Usually the agents will just work with exactly what you’ve already given them, which is the text of your resume and the text of the job posting, but won’t consider broader context. You and the job poster may have both left out some key phrases that can help your resume go to the top of the proverbial “pile”.  

Step 3 – Now that you’ve had a moment to see all of this information. Take a moment and in the same chat, list every skill you can think of that you have picked up over the years and ask your agent to store them all (depending on your plan and tool this may or may not work), but only include the ones that are relevant to this role on the resume. The prompt looks something like this: 

“I’m going to list all of my legal skills and practice area competencies from my legal career to date. Store them all for current and future use, but update my resume to include and highlight the ones that are relevant to this opportunity. 

  • Litigation prep 

  • Depositions 

  • 2nd chair trial experience 

  • Defense-side litigation 

  • Etc.” 

Step 4 – Review and remove AI-isms so your application isn’t rejected as “slop”: 

Now it’s time for some hands-on editing. Download an editable version of your resume and check for the following hallmarks of AI to humanize your resume. 

  1. The “X & Y” format. AI loves to make a bullet point list of your core skills and make them all something like “Legal Research & Writing” or “Litigation Prep & Depositions”. You will end up with a long list of skills with suspiciously identical syntax. Get in there and give it a little more texture and put those skills in your own words. 

  1. “It’s not THIS, it’s THAT”. This one might not show up as much in resumes, but it’s the fastest way for someone to clock that your resume was an AI creation. Eliminate this entirely from your resume where needed. 

  1. Self-promotional language. Sometimes AI gets a bit carried away with self-promoting language. That may be fine for business roles, but it often rubs partners hiring attorneys the wrong way. They want a very straightforward and factual sounding resume, so go through and remove any language that seems too sales-y. You can also try including in your original prompt that you want the tone to be very straightforward. 

  1. Be wary of corp-speak injections. Look out for corporate jargon like spearhead, leverage, orchestrate, result-driven etc. A little bit is fine, but if your resume reads like PE Guy’s LinkedIn page, it’s time to replace those words or phrases with more plain language.  

Step 5 – One last review for hallucinations and accuracy, then send it off! 

If you store all of this information within the same chat with the same agent, then you can come back and just use Step 1 for each subsequent role. Saving you time, while also making sure your valuable work experience is not discounted.