What to Look for in an Executive Coach (From Someone Who's Been on Both Sides)

I've been on both sides of executive coaching—first as a client navigating two decades of financial services and information services leadership, then as a coach myself. So I know that finding the right coach feels a bit like dating: there are a lot of options out there, and frankly, not all of them are going to be a good fit.

The stakes are high because this isn't just about getting advice. It's about finding someone you can trust with your career challenges, your self-doubt, and your ambitions.

So how do you know if someone's right for you? Here's what I tell people to look for—and what I've learned matters most after two decades in a leadership role in the financial services and information services arenas, employing an Executive Coach to address the tough challenges.

1. They Understand Your World

Generic coaching advice is fine for generic problems. But when you're dealing with compliance headaches, stakeholder politics, or market chaos, you need someone who gets it without a 20-minute explanation.

I spent my career in financial services and information services—building teams, navigating regulatory complexity, and managing through volatility. When a client tells me about a compliance nightmare or a manager and team that doesn't understand their strategy, I don't need a primer. I've been there. That context matters because it means we can get to the real work faster.

Questions to ask: Have you worked in my industry or a related role?

What challenges have you helped leaders in my sector navigate? (If they start talking in vague platitudes, keep looking.)

2. They Have Real Credentials (Not Just a Website)

Here's the thing: anyone can call themselves a coach. There's no licensing board. So credentials are your safety net.

I'm an ICF Professional Certified Coach (PCC), which means I've completed rigorous training, logged hundreds of coaching hours, and passed a pretty intense assessment process. It's not gatekeeping—it's assurance that I know what I'm doing and that I'm held to ethical standards.

Questions to ask: What credentials do you have? How many coaching hours have you logged? Do you keep learning, or did you stop after your first certification?

3. They Use Tools That Actually Help You See Yourself Clearly

Good coaching isn't just good conversation. It's backed by assessments and thoughtful questions relevant to what you have shared, that reveal patterns you can't see on your own.

I'm a huge believer in emotional intelligence assessments—I'm credentialed to administer them because I've seen how powerful they are. EQ often predicts leadership success better than IQ. When you can see your blind spots in data, not just in feedback, it changes everything.

Questions to ask: What assessments do you use? Are you certified to use them, or are you winging it? How do they fit into the actual coaching?

4. They Can Point to Results (Not Just Good Vibes)

Ask for examples. Not names—coaches can't share confidential details—but outcomes. Promotions. Team transformations. Successful pivots. Better work-life boundaries.

If a coach can't tell you about the tangible changes their clients have made, be skeptical.

Questions to ask: Can you share what kinds of transformations you've helped clients make? What outcomes have you seen? (Watch for vague promises without specifics.)

5. You Actually Like Talking to Them

This one's simple but often overlooked: Do you feel comfortable with this person?

Coaching requires vulnerability. and building trust through conversation. You're going to talk about failures, fears, and things you don't admit to most people. If you don't feel safe—or if something feels off during your first conversation—trust that instinct.

Chemistry isn't everything, but without it, nothing else matters.

Questions to ask: What's your style? How do you handle pushback? What does a session with you actually feel like?

Trust your gut: If you feel judged or rushed, move on. The right coach challenges you and makes you feel heard.

6. They're Clear About How This Works

You should know exactly what you're signing up for: How often do you meet? How long is the engagement? What happens between sessions? How do you measure progress?

A good coach gives you a clear agreement upfront. No ambiguity, no surprises.

Questions to ask: What's your process from start to finish? How do we track progress? What support do I get between sessions?

7. They'll Hold You Accountable (Even When It's Uncomfortable)

The most valuable thing a coach does isn't give you advice—it's hold you accountable to what you say you want.

I'll help you set goals, identify actions, and then I'll check in on whether you did what you said mattered to you. Not to shame you, but because follow-through is where change happens. Insights without accountability just fade into good intentions.

Questions to ask: How do you ensure I follow through? What happens if I don't? How do you help clients who get stuck?

The Bottom Line

Hiring a coach is a bet on yourself. Don't settle for the first person you find. Ask tough questions. Trust your instincts. Look for someone who has relevant experience, real credentials, proven results—and someone you'd actually want to talk to.

If you're a growth-minded leader, I'd be happy to talk. No pressure, no pitch—just a conversation about what you're working on and whether coaching might help.

Book a 30-minute discovery call: https://calendly.com/maryellendonlevy

Connect on LinkedIn: https://www.linkedin.com/in/maryellendonlevy/