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AI, Careers & Confidence: How to Future-Proof Your Professional Path with Dr. Kyle Elliott

Updated: May 14


Lately, I’ve been speaking with more and more professionals - especially those in tech - who are feeling the pressure. Pressure to keep up, to stay relevant, to not get left behind as AI reshapes the world of work at lightning speed.


In this episode of The AI Grapple, I sat down with Dr. Kyle Elliott, a career coach who works with senior leaders at some of the biggest tech companies in the world. What started as a side hustle on Fiverr for Kyle has grown into a powerhouse brand - CaffeinatedKyle.com - where he now helps C-suite execs future-proof their careers. And spoiler: he’s not just offering résumé tips.


Will AI Replace Me?

That’s one of the most common questions Kyle gets from executives. And while the short answer is no - AI won’t replace senior leaders anytime soon - the reality is more nuanced. What’s happening instead is a shift in the type of work being done.


Rather than eliminating jobs outright, AI is transforming them. Data analysts are turning into data managers. Administrative tasks are being automated, but someone still needs to manage the systems behind that automation. It’s less about being replaced, and more about adapting.


Kyle gave the example of medical scribing. Where once a human would write up doctor’s notes, AI is now ticking boxes and summarising in real time. But someone still needs to design, test and manage that process.


Middle Management in the Firing Line

While C-suite roles might be safer for now, Kyle’s seeing major cuts in middle management. Roles are being restructured, broken up, or replaced by hybrid AI systems. But that doesn’t mean there’s no hope. It means professionals need to become proactive.


His approach? Start with what you actually want to be doing. Then, map that against what’s available in the job market. It sounds simple, but many people skip this part. He also encourages his clients to use LinkedIn for research - look at people who’ve held similar roles and see where they’ve moved.


Using AI to Power Your Career

One of the biggest takeaways from our chat: AI is a tool - not a crutch. Kyle helps clients use AI to support their job search and career planning, but he’s clear that it only works as well as the information you feed it. He recommends using documents like performance reviews, old résumés, or 360 feedback to train AI tools and get better, more personalised output.


We even chatted about a custom GPT I built for a friend - Jobby the Job Hunting Elf - that helped her evaluate jobs, prepare for interviews, and boost her confidence during a rough patch. Kyle loved that. But he was quick to note: you still need to do the thinking. AI won’t - and can’t - do it all for you.


Emotions, Motivation & AI

When fear is high, motivation is low. Kyle’s well aware of the emotional side of career disruption. His advice? Don’t overwhelm yourself. Treat AI like Duolingo - spend 10 to 20 minutes a day learning. You don’t have to master it all overnight.


He also stressed the importance of finding AI experts and learning from those already deep in the field. Just as you wouldn’t expect to master a language in a week, you won’t master AI that fast either. Be patient.


The Future of Recruitment

Recruitment is one area where AI is both exciting and potentially problematic. Kyle’s seen platforms that remove names or universities from CVs to reduce bias. Others are automating interviews, sometimes just summarising your résumé instead of reading it line-by-line.


But there’s a flipside. AI-generated job applications and recruiter spam are leading to distrust on both sides. Authenticity and disclosure are becoming critical. Are you using AI in your application? Did that recruiter actually message you - or was it a bot?


It’s murky. And while AI detection tools exist, they’re far from perfect. What’s needed, Kyle suggests, is a clearer framework around how AI is used and when it should be disclosed.


What Does a Bright AI Future Look Like?

To Kyle, AI is just another tool in the toolbox - like spellcheck or a calculator. It can enhance accessibility, productivity, and efficiency if used right. But it’s up to each of us to decide how we’ll use it.


He’s optimistic. And I am too.


As we closed out the episode, Kyle reminded us all to take it one step at a time. Whether you're a seasoned executive or just starting out, the best way to future-proof your career is to stay curious, keep learning, and use the tools available to you - AI included.


Final Thoughts from Kate

If there’s one thing I hope you take from this conversation, it’s this: AI isn’t just for techies. It’s for all of us. Whether you’re rewriting your résumé, preparing for a new role, or just trying to figure out what’s next - it can help.


But it won’t do the work for you.

Start with who you are. Get clear on what you want. Then use the tools - AI included - to move forward with clarity and confidence.


And if you need support along the way? Kyle and I are both just a click away.



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