In this episode of The AI Grapple, Kate vanderVoort is joined by Dr Kyle Elliott, a career coach to tech executives and founder of CaffeinatedKyle.com. From humble beginnings offering £5 CV reviews on Fiverr to coaching leaders into top roles at Meta, Google and Amazon, Kyle shares what’s really happening in the job market - and how AI is shifting everything from CVs to C-suite expectations.

Whether you’re a job seeker, business leader or simply watching the AI wave roll in, this episode delivers grounded, practical advice to help you stay relevant, empowered and ahead of the curve.

What We Cover:

👉 Why middle management is most at risk - and what to do about it
Kyle shares what he's seeing across his client base: mid-level roles are often being consolidated or automated. It’s not about roles disappearing completely, but shifting into jobs that involve managing AI-powered processes instead of performing tasks manually. He explains how professionals can identify emerging opportunities and pivot early.

👉 The AI tools job seekers should be using now (and how to train them)
AI isn’t magic - it only knows what you give it. Kyle explains how his clients use tools like ChatGPT to write CVs, simulate interviews and even explore new career paths. But success depends on input: the better the data you provide (like performance reviews or personal profiles), the better the output AI delivers.

👉 How AI is changing executive-level hiring and job strategy
Even at the top, AI is having an impact. Kyle explains how senior leaders are being assessed differently, what they’re worried about, and how they're learning to talk about AI in ways that show leadership, not fear. It’s about knowing when to use AI - and when to lean on your human skills.

👉 The emotional side of job searching in the age of automation
Being made redundant or feeling threatened by change brings real emotional challenges. Kyle talks about the role of mindset coaching and shares an example of a custom GPT built to motivate and coach a client through job hunting - including cheering them on when things got tough.

👉 Why the best AI results come from knowing yourself better
To get personalised, useful help from AI, you have to start with self-awareness. Kyle talks about the importance of building a “professional me” document - a profile of your background, skills, preferences and values - that can train AI to reflect who you really are and what you need next in your career.

🔗 Connect with Dr Kyle Elliott:

Website: CaffeinatedKyle.com

LinkedIn: Dr Kyle Elliott

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