3 Qualities of Great Coaches and Therapists

Recently, I was asked to do some executive coaching but ended up saying no.

But after receiving my note, the person asked a follow-up question I couldn’t stop thinking about:

What specifically would you look for in an exceptional coach?

I started reflecting on the handful of coaches and therapists I know personally that I admire and consider truly great at their craft.

I came up with three qualities or attributes that I think all the very best coaches and therapists have.

Note: For simplicity sake, I’ll just refer to coaches from here on out. But everything I mention applies to therapists and counselors as well as coaches.

1. Clarity

It sounds obvious, but it’s hard to make progress when you don’t know what’s holding you back.

A lot of people go into coaching with some idea of the problem:

Confidence issues are holding me back professionally…
My anxiety and insecurities are sabotaging my romantic relationships…
Insomnia is ruining my life…

But these initial theories are often either too vague to be helpful, missing a deeper root cause, or sometimes just completely wrong. All we really know is that we’re struggling and not where we want to be. And we hope that a coach can help.

The mistake that both clients and coaches make is thinking that the coach will be able to achieve insight into the problem themselves, hand out some tips and tools to make progress, and off we go. But in reality…

A coach’s ability to accurately understand the problem is constrained by the client’s ability to accurately describe it.

Of course, any good coach will have some intuitive sense for the issue based on pattern matching and past experience. But that intuition is frequently incorrect because no matter how much client X resembles client Y, individuals are wildly complex and far less predictable than we coaches want to believe.

Now, you’re probably thinking to yourself:

But if clients aren’t good at understanding their problems, and coaches aren’t good at intuiting their problems, is the whole thing just a waste of time?

For a lot of people who do coaching, yes—I think it is basically a waste of time (and money) because they never achieve the clarity required for meaningful progress.

But that doesn’t mean it always is.

The way to resolve the dilemma above is to realize that while neither client nor coach alone can understand the problem, if they know how to work together well, they can usually get there. But client and coach working together—being genuinely collaborative—is much harder and more rare than people realize because it requires an attribute that most coaches don’t have:

The ability not only to think clearly about complex issues, but to help their clients do the same.

The real magic of great coaching happens when the coach teaches their client how to start thinking more clearly themselves. This leads to more accurate insights about their experience, which then helps the coach deliver more helpful recommendations.

Sadly, coaching often leads to more confusion, not less.

When I start working with a new client, I usually ask them to tell me a bit about what their previous experiences in coaching were like. And almost universally I hear some version of the following:

Well, my coach was really nice and supportive. And it felt good to have someone to talk to. They even gave me some good tips and techniques. But at the end of the day, I’m not sure anything really changed.

That lack of meaningful progress isn’t because the client or coach weren’t well-intentioned, motivated, or smart. It’s because most coaches, while they’re taught to diagnose or assess a problem on their own, are rarely taught how to help their clients think more clearly. It’s a totally different skill set and most simply don’t have it.

A great coach doesn’t tell you what’s wrong; they teach you how to see what’s wrong yourself.

A hallmark of working with a great coach is that you genuinely start to understand yourself better. Not in the superficial sense of my therapist told me I’m anxiously attached and now I feel validated for decades of insecurity in romantic relationships.

That’s not insight. That’s just jargon.

Genuine insight is when you can explain what you’re struggling with and why without the use of jargon or therapy/coaching speak.

Now, it’s very hard to predict ahead of time whether a coach has this quality of clarity. Which means you’ll likely have to test drive a number of coaches while specifically looking for this quality of clarity.

Luckily, if you know what you’re looking for, I don’t actually think it’s that hard to identify…

As I work with my coach, do I genuinely feel like things are getting clearer? Or do I feel like things are just getting more confusing?

Of course, even with a great coach, this won’t happen overnight. It usually takes at least a handful of sessions. And sometimes things do need to get more confusing before they become clear.

Still, the overwhelming feeling you should have with a great coach is that you are thinking more clearly about yourself, not less.

2. Empathy

If you ask ChatGPT to list the qualities of great coaches, empathy will be at or near the top of the list.

So why include it here if it’s so obvious?

First of all, just because it’s obvious doesn’t mean it’s unimportant.

But more importantly, I included empathy because I actually don’t think it’s so obvious—at least not in the way that most people imagine…

Most people hear the term empathy and they think of someone who’s kind and supportive. And while kindness and support are often side effects of someone who’s empathetic, true empathy is a different thing entirely.

A good definition of empathy comes from Theresa Wiseman, who says that empathy is a complex skill involving four distinct components:

Perspective-taking. The ability to see a situation from the other person’s viewpoint. It takes high levels of imagination to do this well.
Non-judgment. The ability to dispassionately acknowledge the thoughts, feelings, behaviors, and experiences of another person without your own biases or ego interfering.
Emotional identification. The ability to accurately sense or identify what the other person is feeling in the moment.
Communicating understanding. The ability to demonstrate to the other person that they are understood in a clear and compelling way.

Note that these are all abilities, not intentions. Most coaches genuinely strive to be empathetic, it’s just that their ability is decidedly average. Because as you can see from a careful reading of the above, being exceptionally skilled at empathy is quite a high bar! And like any skill—from playing the violin to investing in the stock market—very few people are exceptionally good at that skill.

Great coaches need to be exceptionally empathetic because to truly understand their clients and work productively with them, they have to be able to suspend their own biases and beliefs to see things objectively. And this is very difficult. Much more difficult than most coaches assume.

So, how do you know if a coach is high in empathy?

Here are a few suggestions:

Don’t confuse nice with empathetic. Your coach should absolutely be supportive and respectful, but what you’re really looking for is evidence of genuine empathy. Stay mindful of that distinction. It’s also worth noting that you can have a coach who’s not exceptionally kind but is exceptionally empathetic.
Look for intense curiosity. I’ve found that genuine and intense levels of curiosity about you, your struggles, and your goals is a very good predictor of high levels of empathy. And if a coach seems apathetic, uninterested, or not especially engaged, that’s obviously a bad sign.
They’re “in your head.” If your coach consistently says things that make you feel like they’re reading your mind or describing things even better than you could, that’s a good sign.
Watch out for excessive sympathy. Sympathy is when one person feels the emotional pain of another. While a little bit of sympathy is normal and potentially helpful, excessive sympathy frequently interferes with empathy.
Shared metaphors and inside jokes. One good sign that a coach is especially empathetic is that they quickly and easily pick up on your metaphors and distinctive language patterns and use them with you. This often takes the form of a coach using metaphors or analogies you’re especially familiar with to explain or explore a complex idea or topic.
Oversharing is a strong counter signal for empathy. Be very careful of coaches who tend to overshare about their own experiences or feelings. This can be an indicator that they have too many of their own unaddressed emotional issues to maintain the boundaries required to empathize objectively. In other words, you don’t want a coach projecting their issues onto you and thinking it’s empathy.

3. Courage

I hesitated to include this one because most of the time in coaching it’s not especially important. But there often comes a time—especially in longer-term coaching engagements—when the coach is faced with a dilemma:

They have a strong conviction that the client needs to move in a certain direction but they’re afraid to bring it up.

Here’s a recent example from my own experience:

I had a client who would routinely cancel our sessions last minute.
I suspected this was the result of a deeper pattern where they would get upset about something, but because they were afraid to state it directly, they used passive-aggressive behavior like chronic lateness and cancelling appointments to try and indirectly express their anger.
I guessed this was going on because I’d noticed a similar pattern when they described several examples of relationship conflicts, both at work and in their personal lives.
Still, I was anxious to bring it up. Partly because I was afraid of them getting angry—I liked this client and wanted them to continue liking me. But they also paid really well, and if I’m being honest, I was afraid to lose them as a client if this issue blew up.
Now, I’m not proud of it, but there have been similar situations in the past where I essentially stayed quiet about an issue because, as a coach or therapist, I was afraid of upsetting my client and having to deal with the aftermath. I would rationalize it to myself by saying things like “It’s not my place” or “I shouldn’t be too directive.” But deep down, I believed speaking up was the right thing to do.
In moments like this, I try to remember something an old mentor told me: “A great therapist is willing to lose the relationship in order to do the right thing by their client.” The longer I work as a coach, the more strongly I believe that and try to live up to it.
So, in this situation, I did bring up the issue with my client. And while they did get initially defensive and angry, they came back the next session and thanked me for being willing to call them out on that behavior.
We then went on to have our most productive phase of coaching because, having cleared the air on that pattern in our relationship, my client felt much more confident doing the same in several other relationships—including with their CEO at work which ended up leading to a pretty major breakthrough in my client’s career.

Of course, the way a coach goes about doing this is important: Courage without compassion or humility, for example, is much more likely to backfire.

Still, the bigger point remains: It sometimes takes a great degree of courage for a coach to help their client grow in the most important things.

So how do you know if a coach has this quality of courage, especially if it’s not something that needs to be demonstrated frequently?

Here are a few ways:

Ask for an example. When you’re interviewing a coach initially, ask them about a time when they had to give their client some difficult feedback and they were scared. If a coach has done this, they’ll have plenty of examples. If they seem to struggle with the question or avoid it, that’s usually diagnostic.
Criticism without judgment. Most coaches aren’t critical enough because they conflate being critical with being judgmental. And while they rightly want to avoid being judgmental, they end up throwing the baby out with the bathwater. It’s a coach’s job to be critical! And it’s perfectly possible to do so—to observe, theorize, and communicate critically—without being judgmental. If you have evidence of them doing this in small ways, the odds are better that they’ll be willing to do it in big ways when necessary.
Lack of defensiveness. You want a coach who’s confident enough to be courageous in their feedback when necessary. But it’s hard for a coach to be confident if they’re insecure. And a lot of coaches are very insecure—broadly and about their abilities as a coach specifically. So how do you tell if a coach is confident or insecure? One good proxy for insecurity/confidence is how they handle criticism or negative feedback. If you give your coach some negative feedback or criticism, how do they handle it? If they get defensive, that suggests a high level of insecurity, and as a result, I’d be skeptical about their ability to courageously give you difficult feedback in the future.

Of course, none of these will tell you for sure whether a coach is willing to be courageous or not. But it’s a hard problem and these are some of the best indicators I’ve found.

All You Need to Know

I’m not claiming that these three qualities are sufficient for a great therapy or coaching experience. Obviously there are plenty of other factors that matter like professionalism, self-awareness, emotional intelligence, communication skills, etc.

I’m not even sure they’re necessary. Depending on the specifics of the client and their issues, you could probably get very good results out of coaching even if your coach strongly lacked one of these qualities.

But if your aim is to work with an exceptional coach, your odds are much better if they have these three qualities to a high degree:

Clarity. They have an uncanny ability to think clearly about complex issues and they help you to do the same.
Empathy. They are exceptionally skilled (not just well-intentioned) at perspective-talking, non-judgmental assessment, as well as emotional identification and communication.
Courage. They are willing to risk the relationship to help you grow when you need it most.