I’m currently investigating a new tool that might make resume customization simpler and faster. Yes it is an AI tool – not ChatGPT, but something more specialized.

Here’s what I know about job searching today.
- There are ever more tools, apps, services, and shortcuts proliferating like lichen across rocks – that may or may not be high quality;
- AI generated resumes may or may not help your resume get past any particular ATS gatekeeper (see above);
- Templates still have their own problems; and
- Human readers still want to read a resume and cover letter that feels like a human wrote it – a specific, individual human with their own personal take and point-of-view.
The point of customizing to make your resume both fit the job AND showcase you as a unique individual.
For this reason, the services that offer to submit to jobs for you and save you the work of customizing may not be as helpful as you would hope. Many careers pages still warn against “agency submissions”, and only including copied keywords and no personality does not advance your application – especially once a human sees it.
Plus, an AI resume writer responding to a job listing might be able to suggest the need for a metric (as I hope the good ones will) but won’t have access to that particular data/information that you will want to add – see my recent article on LinkedIn about keeping records for metrics.
No AI will replace your judgment and input to your resume and cover letter.
Style Mirroring
Something that you can do as a human is respond with gut feelings. Just as discovering pain points needs more art than just keyword counting, so is having a sense of the style of a job listing, and the language style of the organization, as shown in the website as a whole.
- Different departments within a company might have different styles. Think of the formality of language coming from any Legal department, no matter how lively and freewheeling the language style of social posts.
To confirm the style, I like to read the job listing aloud. Most of the time they tend to be conversational, but not casual. There is usually a balance between friendliness and the jargon of the particular department. I’m looking for clarity and consistency.
I also check for pronoun use – more pronouns means more casual. Most of the time I will see “this role” or “this position” or “the ideal candidate” rather than “you”. Then of course, there are those idiosyncratic expressions that are perfect opportunities to NOT use as keywords, but to find your own synonyms. This helps you keep your keyword match count at the sweet spot around 85%.
Here’s an example of a summary paragraph with some pronouns:
“You will be jumping right into existing projects, so you must be able to learn and adapt quickly.
We want to hear from you if you enjoy over-delivering rather than meeting expectations. You want to succeed, you are driven, efficient, organized and understand how fast paced this industry truly is. We want a leader and team player who can take pride in being part of something good.”
It’s the job listings that are outside of the “business conversational” norm that need the most attention when it comes to customizing for style.
Then there are those job listings that unfortunately appear to consider actual communication as optional. Sometimes the phrases are obfuscatory rather than expressive. Sometimes there is just too much jargon – they definitely are trying to shrink the applicant pool with esoteric language.
Sometimes the priority appears to be brevity rather than information. Does this mean the job itself is simple or maybe entry level? Possibly.
Here are all the duties of an entry level job that openly acknowledges that it is that – with no prior experience specified. The language is straightforward and makes sense with sensible verbs.
“Working alongside the team in the role of Assistant to CEO, your responsibilities will be as follows:
• Oversee and manage the CEO’s inbox, ensuring timely responses and appropriate delegation
• Maintain and optimize the CEO’s schedule, including prioritization of daily, weekly, and long-term goals
• Act as a gatekeeper and strategic buffer between the CEO and incoming requests or distractions
• Prepare agendas, follow-ups, and briefing materials for meetings
• Keep the CEO on track with pressing deadlines and priorities
• Handle confidential information with discretion and professionalism
• Assist with both personal and professional tasks as needed to ensure peak productivity”
By contrast here is an overly wordy job description that uses some fairly fancy language, that turns out at the end to be an entry level position (high school diploma only) with a fairly low wage. The language makes simple duties appear less so, and could make people turn their resume into a document that sounds inauthentic. The language might even discourage perfectly qualified people. (Plus a typo, but that’s not important.)
“WHAT THIS ROLE WILL DO
• Answer inbound calls to help resolve our customer concerns through analysis to determine the most effective resolution.
• Assist guests and staff with any questions or needs.
• Manage the filing and logging of lost and found items
• Support various show day projects, often times including tasks on Microsoft Word, Excel and Power point
• Deliver exemplary customer service to maintain customer loyalty
• Adapt to customer needs ensuring they are understood and appropriate action is taken to meet and exceed their expectations
• Keep records of customer interactions or transaction, recording details of inquiries, complaints, or comments, as well as action taken.
• Refer unresolved customer grievances to designated departments for further investigation
• Other duties assigned by the General Manager and Assistant General Manager”
Sometimes the feeling is “breathless enthusiasm”. This is characterized by multiple questions, plenty of assertions with exclamation marks, and a tendency to use many “You” pronouns. My first feeling on seeing these is wariness. While certainly not universal, some of these jobs remind me that “if it’s too good to be true, it probably isn’t.” I would take this as a cue to research the company more before applying.

Photos via Canva.
Sometimes the enthusiastic approach works. I notice that often these enthusiastic jobs are commission based, like this one that uses a lot of bold for emphasis. There is a slight disconnect between their number one need – your industry contacts – and their claim that they already have a “massive rolodex.”
On the plus side, the ideal candidate is absolutely clear both in terms of qualifications and the desired soft skills and personality. The whole listing uses the word “hustle” three times. This job is not for everyone, but the listing is written to attract exactly the right people.
“– ? We’re Looking For Someone Who:
* Is a seasoned celebrity talent booker or talent producer with authentic industry relationships and booking credits/real references to show for it
* Understands how to pitch premium talent, package deals, and negotiate win-win outcomes
* Is collaborative, trustworthy, and thrives in a team environment
* Is motivated by commission and sees the long game – not just the quick win
* Understands the pace and professionalism required to work with A-list talent
– This Role Is Not For You If:
* You’re not ready to hustle or prefer structure over initiative
* You don’t have real, working entertainment and other industry contacts and relationships
* You’re not interested in building with a fast-growing boutique brand”