Knowing how hiring works does not prepare you for what job hunting actually feels like right now. Today’s guest, Nicole, found that out the hard way. She has spent 30 years on the hiring side of the table. She has interviewed hundreds of candidates, read thousands of applications, and knows exactly what good looks like. So when she re-entered the job market after a six-month sabbatical, she found herself starting from scratch. 

Nicole, a senior executive, knew how the game used to work. What she didn't know was how much it had changed. AI-generated resumes flooding inboxes. Applicant tracking systems filtering on past performance. Three or four hundred applications for every role, most of them indistinguishable from one another. The playbook she had built over decades wasn't quite fitting the game anymore. 

This episode is part of The Work Edit, a new format on How I Work where I sit down with someone facing a real professional challenge and we work through it together. Nicole came to me wanting help with the part of job hunting that was giving her the most trouble: getting from application to shortlist. We get practical about what actually works right now, from why a written application might be the weakest version of your pitch, to how to use AI to run your own mock interview and genuinely sharpen your performance in ways most people never bother doing. 

If you are currently in the job market, or know someone who is, this one is worth sharing. 

We discuss: 

• Why the job market has shifted so dramatically in the last few years, and what that means for experienced candidates re-entering the workforce 

• How applicant tracking systems work and why they tend to filter out people with non-linear careers or future-focused skills 

• The case for treating your job search as a sales role, and what that reframe actually changes about how you show up 

• Why a short video pitch cuts through in a way that a written application simply cannot right now, and what makes the difference between a video that opens doors and one that falls flat 

• What AI fluency actually looks like in a resume or cover letter, and how to find and remove the tells that signal lazy prompting to any recruiter paying attention 

• How to use AI to run your own mock interview, and why stopping short of the critique step means leaving most of the value on the table 

Key quotes 

"If you're not AI fluent, why would you be considered for a job in this day and age?" 

"I think if you are purely relying on your resume and cover letter being the best out of 400 applications, that is a losing game."