Is Your AI “Career Coach” Asking You the Right Questions?

Or should I say—is it asking you the hard questions?

Yesterday, one of my clients admitted to using Elon Musk’s Grok AI to figure out why his job search had stalled. I was slightly incredulous. We had already designed a proven job search strategy—a customized, efficient, and effective plan. At this point, all he needed to do was execute.

Yet there he was, endlessly scrolling job boards like a helicopter parent circling a playground. He told me that every LinkedIn job posting seemed to have over 2,000 applicants. Understandably, that’s discouraging. That's why spending hours on job boards wasn’t part of our strategy—and there’s a reason for that.

Why Job Boards Don’t Work (and What Does)

We already know that job boards have low response rates. Research consistently shows that 75% of jobs are found through networking, and about 50% of open positions are never even posted. So why was my client slipping back into the job board loop?

The answer: he was avoiding networking.

And that’s the real question an AI career coach doesn’t ask—why are you avoiding a particular action? That “why” is often the key to progress. Until we addressed the reason behind his resistance, he couldn’t move forward.

When AI Coaching Falls Short

As a coach, I can guide, strategize, and bring structure—but I can’t act on your behalf. Interestingly, my client told me that both Grok and ChatGPT gave him the same advice I had. For a second, I had flashbacks to my daughter—you know how kids only listen to advice when someone else says it!

Still, despite getting the same guidance from his AI career coach and his real-life coach, he remained stuck. Why? Because even though the AI wore the “career coach” persona, it couldn’t actually coach him as an individual.

The Human Difference: What Real Coaches Bring

This is where AI coaching and human coaching diverge. As a professional coach, I bring far more than strategies and checklists. I offer:

• Decision-making frameworks

• Accountability and structure

• Problem-solving systems

• Industry knowledge and insights into the job market

• An understanding of corporate politics

• The ability to read between the lines

Yes, AI tools like ChatGPT or Grok can generate a plan in seconds. But they can’t account for the human factors—your personal history, environment, mindset, and fears. Those elements shape your actions and, ultimately, your success.

Your individual story is the hidden key to unlocking your potential. When your story is understood and integrated into your strategy, that’s when you move forward—not just toward your goals, but beyond them.

Final Thought

AI career tools like Grok and ChatGPT can be incredible aids. They provide quick insights, structured plans, and even motivation. But when it comes to identifying what’s really holding you back—when you need someone to ask the hard questions, challenge your assumptions, and help you grow—that’s where human coaching still reigns supreme.

Because sometimes, what you need isn’t another plan.

You need someone who can see what you can’t.

(Orignal post on LinkedIn)