How To Choose The Right Leadership Coach

Reading time: 6 minutes

Let’s be real – there are a lot of leadership coaches out there.
Like… a lot.

It seems these days that any mid- to senior-level person without a job and with a strong opinion about leadership behavior is calling themselves a leadership coach. There’s no test you have to pass to hang up your coaching sign. The barrier to entry is basically “I’ve got time, I own a Zoom account and I’m pretty sure I can help people.”

Which means it’s not always easy to know how to choose the right leadership coach – and choosing the wrong one is a pretty expensive way to learn that lesson. So if you’re wondering how to choose the right leadership coach, this is the guide.

What I’m going to tell you is how to weed through the muck to find the diamond in the rough.
(I know, I’ve mixed metaphors, but how about we don’t get held up by that right now.)

First, Get Clear On What You Actually Need

To know how to choose the right leadership coach, you first need to know what the problem is that you’re trying to solve. Because “leadership coach” is a pretty vague term these days – it covers almost anything at work. More importantly, a coach who’s great at one thing can be a complete buffoon at another.

(For instance, my leadership coaching services focus on uncovering the unconscious patterns limiting your growth. So I’m probably not the best person to work with if you just want help interviewing for a new job.)

Are you a newly promoted leader trying to make the transition from individual contributor to manager? That’s a different type of conversation than a seasoned VP who keeps hitting the same organizational headwinds. And that’s different from a CEO who needs executive coaching to help with high-level strategic thinking.

It helps to understand your end goal before you start talking to coaches. The clearer you are on what’s not working and what you want to change, the easier it is to evaluate whether a particular coach has actually worked on that problem before – or is just telling you they can help.

(Be careful of the coaches who always tell you they can help, regardless of your need. That’s a red flag warning.)

How To Choose The Right Leadership Coach: What to Look For

They have a methodology, not just a philosophy. Every coach has a perspective on leadership. But that’s not enough. You want someone who can explain specifically how they work – what happens in the first session, how they diagnose what’s actually going on with you, what their process looks like over time, and how they measure whether it’s working. Vague answers about “meeting you where you are” and “co-creating the process” are not methodologies as much as they’re ways of avoiding the question.

(There’s your second red flag warning – people who don’t actually answer your questions.)

They can tell you what they can’t help with. This one is important – that’s why I mentioned it in the previous section and I’m repeating it again down here. A coach who claims they can help you with everything is a coach who can help you with nothing particularly well. The best coaches are clear about their strengths and will be direct with you about when they aren’t the best fit. If you ask a coach “what kind of clients are not a good fit for you?” and they struggle to answer – there’s your third red flag warning.

They push back. You shouldn’t hire a yes-person. Knowing how to choose the right leadership coach means hiring someone that can reveal to you the things you can’t see yourself – including all the uncomfortable things that are tough, and maybe a little cringy, to hear. If your first conversation feels like they’re just putting you on a pedestal, guess what? Yep, red flag number four. The most valuable coaching usually has moments of feeling uncomfortable. A coach who’s too focused on making you feel good isn’t going to make you better. Growth happens in the discomfort zone.

They’ve done the work themselves. Not necessarily in your exact industry or role – but they should have some real-world experience that isn’t purely academic. Coaches who’ve led teams, built companies, or navigated significant organizational complexity bring a different kind of credibility than those who went straight from a coaching certification into a coaching practice. The right leadership coach knows what the hard parts actually feel like.

The chemistry is real. You’re going to be telling this person things you probably haven’t told anyone else – so you better feel comfortable with them. If the trust and rapport isn’t there in the first conversation, it’s not going to magically appear after you begin working together. Sure, perfect chemistry isn’t required, but a lack of any chemistry? Red flag number five.

What to Watch Out

The coach who leads with frameworks. If the first thing a coach pitches you is their proprietary model – the Five Pillars of Pillar Creation, the Seven Habits of Yada Yada Yada – be skeptical. Frameworks can be really useful tools, but they aren’t all-in-one solutions. You are unique, just like everybody else. Though your issues may be the same as others, they probably manifest in different ways. It’s important they see you for who you are.

The coach who won’t tell you their results. Good coaches can point to outcomes. Not in an overly salesy “check out my testimonials page” type of way, but in a real conversation about what their clients have worked on and what changed. If a coach gets evasive or abstract when you ask about their success, that could be a problem.

The coach who’s too quick to say yes. If someone agrees to work with you without asking you the questions about what you’re struggling with, what you’ve already tried, or what’s gotten in the way before – they’re simply not doing their job. Good coaches are selective. They’re evaluating fit as much as you are. In fact, I’ve turned down my potential clients than I’ve accepted – simply because I know I’m not the right fit.

The coach who makes you feel a little too special. Feeling seen and understood is an important element when determining how to choose the right leadership coach. But some coaches use it as a front. They use it for sales and then you get a bait and switch once you start working with them. Here’s how to tell: If the conversation is mostly about how brilliant your challenges are, red flag. If they’re actually trying to understand what’s behind your challenges, that’s a good sign.

Questions Worth Asking in That First Conversation

Don’t just let the coach run the initial call. It’s better for both parties when you show up with your own questions. Their answers will tell you more than their sales deck ever will and it’ll really help you know how to choose the right leadership coach and not end up with the wrong one.

Here are some good questions to ask:

“What does your process actually look like?” You don’t want the philosophical answer – you want the practical one. To get more specific, you can ask,

  • “What happens in session one?”
  • “How do you diagnose what’s happening?”
  • “What does progress look like at 30, 60, 90 days?”

“Tell me about a client engagement that didn’t work out – what happened?” How a coach responds to this question reveals more about their self-awareness and integrity than almost anything else you can ask. Great coaches put thought into what worked and what didn’t with their clients. They know when things fell short and why.

“What would make me a bad fit for you?” You’re looking for specificity here. “You’d be a bad fit if you’re not willing to do the work” is a non-answer. “You’d be a bad fit if you’re really just looking for help to find a new job opportunity. If that’s the case, I can refer you to some good career coaches.” Now that’s a good answer.

“How do we measure whether this is working?” The right leadership coach can answer this clearly without a problem. After all, you’ll be investing your money and your time into this, there better be a mutual understanding of what success looks like.

The Credentials Question

You’ll notice I haven’t mentioned certifications yet. That’s on purpose.

Some coaches flaunt the credentials they got from passing tests or taking classes.

Don’t get me wrong, credentials from ICF, CTI, or similar organizations are signs that there is formal training and an adherence to a code of ethics. That’s not nothing. But credentials don’t tell you whether a coach is actually good at the work. Unless required by your employer, credentials should not be a major determining factor in how to choose the right leadership coach.

Some of the most certified coaches I’ve encountered have been the least effective in practice. I wouldn’t refer any business to them.

In fact, I’ve never even considered getting credentials, because my story involves 25 years in leadership roles at all size companies – start-up to global enterprise. I’ve made all the mistakes that I now I help my clients overcome. My credentials are my years of experience. The school of hard knocks.

So I wouldn’t treat credentials as a firm requirement or an end-all be-all. They help you answer the “did they bother to learn anything” question, but the bulk of what matters – insight, methodology, real-world experience, results – you have to find that out for yourself.

The Right Coach Is Worth It. The Wrong Coach Is Expensive.

Good leadership coaching will change the trajectory of your career, your team, and your organization. It’s not a matter of can you afford to get the right coach, it’s a matter of can you afford not to. For leaders at the right inflection point, it’s one of the highest-ROI investments you can make. (Check out Leadership Coaching ROI: Is It Worth The Investment?)

If you hire the wrong coach – the one who’s good at selling themselves, good at making you feel understood, but not so good at the real job of helping you see all those things you can’t see on your own – it will cost you six months, a significant amount of money, and the transformation you needed the coaching for in the first place.

So take the selection process seriously. Knowing how to choose the right leadership coach is half the battle – the other half is having the courage to be honest in those initial conversations. Ask the uncomfortable questions. If a coach can’t handle a little push back on during an introductory call, they certainly won’t be able to handle it when it’s you in the hot seat.

If you’re curious whether my approach might be right for what you’re dealing with, let’s have that conversation. I promise that I’ll give you the same direct answers I’m telling you to get from everyone else.

Related Articles

Jeff Matlow is a leadership coach and 3x entrepreneur who helps leaders spot the unconscious patterns keeping their teams dependent on them – then redesign the environment so everyone can actually perform. He’s spent 25+ years working with leaders at Disney, Porsche, Nestlé, and hundreds of high-growth companies. Think Ted Lasso meets Brené Brown meets a Navy SEAL. Learn more about working with Jeff or subscribe to The Best Leadership Newsletter Ever.