Taylor Desseyn on Using AI to Start Conversations, Not Just Send Applications

Taylor Desseyn on Using AI to Start Conversations, Not Just Send Applications

In a recent interview, Taylor Desseyn, who runs the AI Job Search Tips & GC 2.0 Podcast and maintains a free job search coach that people can text, shared his perspective on how AI fits into a job search. His answers challenge some of the most common advice and offer practical steps for job seekers.

When Standard AI Advice Doesn't Fit

Desseyn points out that most advice starts with rewriting your resume using AI, but that can be the wrong first step. He described a conversation with a director of engineering who works in hardware, not SaaS. "I asked him, have you just thrown your resume into AI and asked it what job boards you need to be on? He hadn't even thought of it." Desseyn calls this "basic blocking and tackling" that people skip. Instead of polishing a resume first, he suggests using AI to figure out where people like you actually get hired, building a target list from there, and then worrying about the resume.

The Missing Piece: Follow-Up

While everyone says to talk to more people, Desseyn notes that nobody tells you what to do with the 90 people you already talked to. "Follow-up is one of the single most important parts of the job search, and it's exactly what AI is good at." He recommends having AI log who you talked to and what about after every coffee chat, and remind you to follow up in three weeks. He also highlights the emotional weight of the search: "I built a free job search coach people can text, and a lot of them use it to vent. Honestly, I'd rather they vent there than on LinkedIn."

The Wrong Decision: Focusing on Applications

Desseyn warns that people decide too quickly that AI's job is to send more applications. "AI on its own is not an edge. It's how you use it." He tells the story of Connor, who instead of applying, messaged engineering managers at Netflix about a tool his team was trying to implement. One thread turned into ten conversations, and ten conversations later he had a job at Netflix. "Now AI can find those people and draft the first message for you. You still have to spend the time talking to humans."

Practical Takeaways

• Use AI to identify where people in your field actually get hired, not just to rewrite your resume.
• After every conversation, have AI log the details and set a reminder to follow up in three weeks.
• Measure your search by conversations started, not applications sent.
• Use AI to find and draft messages to hiring managers, but remember that the real work is in talking to people.

For more from Taylor Desseyn, visit his website.