The decision to work with an executive job coach isn’t just about getting help—it’s about choosing someone you’ll trust with your next chapter. Someone who understands what’s at stake when you’re aiming higher, pivoting strategically, or stepping into unfamiliar leadership territory.

It’s not always an easy decision. Coaching can be a powerful accelerator—or a complete waste of time. The difference comes down to the person you choose.

Here are 7 things worth considering before you commit.

1. Do They Work with Executives Like You?

“Executive” means different things in different industries. A coach who works with first-time managers may not be equipped to guide someone aiming for a board seat or negotiating a C-suite offer.

Look for experience that matches your level, not just a generic title. Bonus points if they’ve worked with people transitioning into roles you want.

2. Can They Help You Think Strategically—Not Just Polish Your Resume?

Good coaching isn’t about formatting bullet points. It’s about helping you see where you’re heading, how you’re positioned in the market, and what you might be missing.

Your coach should be able to zoom out and look at the bigger picture with you. If all they offer is job hunt tactics, they may not be the right fit for long-term growth.

3. Do They Know How the Hidden Market Works?

Most executive roles aren’t listed. They’re filled through introductions, quiet conversations, and strategic outreach. If your coach doesn’t understand how to access this “hidden job market,” you’ll be stuck chasing public listings—alongside thousands of others.

They should help you build visibility, not just edit your LinkedIn profile.

4. Do They Listen More Than They Talk?

The right coach won’t show up with a script. They’ll ask questions that challenge your thinking and help you hear yourself more clearly. If they do all the talking—or rely on templates—you’re probably not getting custom advice.

Coaching should feel like a conversation, not a lecture.

5. Can You Talk to Them Honestly?

This one’s personal. If you don’t feel comfortable being fully honest—about your fears, your career mistakes, or what you actually want—you won’t get much from the process.

You need someone who makes you feel heard and respected. If something feels off in the first conversation, trust that instinct.

6. Are They Willing to Challenge You?

The best coaches won’t just affirm you—they’ll push you. They’ll ask why you’re aiming for a certain role. They’ll call you out if your story doesn’t land. They’ll push you to raise your standards, not just your salary.

If it always feels easy, it’s probably not real coaching.

7. Do They Offer Real Value for the Price?

Executive coaching is an investment. It should offer a clear return—whether that’s faster job placement, better offers, more confidence, or smarter decisions.

Before signing on, ask yourself:

“If this works, what will be different three months from now?”
If you can’t answer that, the coach might not be right for you.

Final Thought

Coaching should give you more than advice. It should give you momentum.

Whether you’re changing industries, re-entering the market, or aiming for a bigger role, the right coach won’t just tell you what to do. They’ll help you lead yourself forward—clearer, stronger, and more prepared than before.

If that’s the kind of support you’re looking for, Executive Job Experts offers 1-on-1 guidance built for senior professionals who are ready to move.