What To Do When You’re in the Middle of a ‘Bad’ Coaching Session

Not all coaching sessions are going to go well. Some will feel full of life and inspiration like you’re sitting in the midst of endless possibilities and inspiration. Some coaching sessions will feel boring and challenging like you’re fighting through quicksand with every step.

I wouldn’t recommend you try to make every coaching session great, you won’t succeed and you won’t really be serving your clients. Still finding yourself in the middle of a bad session can be tough so here’s what I do when I feel like I’m in a session that feels like I’m dying a slow and painful death.

1) Admit the session isn’t going very well –

If you’re brave share this with your client. Say hey I notice this session isn’t going the way I thought it might. How is it feeling for you?

They might agree or disagree with you. But by bringing it out into the open you will offer some relief if you’re both struggling a bit.

If that feels too edgy for you then simply admit it to yourself.

2) Remind yourself that everyone has ‘bad’ sessions –

Every performer, artist, master, teacher, and coach has bad days and bad sessions. It’s ok, you’ll survive. So long as you’re not being a total asshole, verbally abusing your client, or sexually harassing them, you’ll survive this session.

If you are doing one of those things please stop immediately and get some support so you won’t do that stuff again. But if you’re reading this article you probably aren’t doing that stuff so don’t worry too much.

3) Take a breath –

When I watch coaching sessions go bad 90% of what’s happening is momentum. The coach gets on the wrong foot, but they just keep going. They keep asking awkward questions. They keep interrupting their client.

So pause. Take a breath. Tell your client you need a minute to review some notes. This small break can give both of you a chance to reset and recenter.

4) Figure out (or remember) what the client wants –

The #1 piece of feedback I give coaches is that your session would have gone better if you had taken the time to find out what your client wanted.

It seems so simple. So basic. But most coaches miss this. They get to coaching and they don’t really discover and confirm what the client really wants. And even then sometimes they lose track of that in the middle of the client’s session.

So if you realize you don’t know what your client wants, pause and ask them. If you think you know, pause and confirm it again.

Just connecting with this simple anchor of desire can make all the difference in the world.

5) Let go of your agenda (or whatever else you’re holding onto) –

I once had a client that I felt was totally uncoachable. Every reflection I offered was met with a correction. Every question I asked was answered in the most disconcerting way. It felt so hard to figure out what to do next.

Then one session I simply let go of how I thought our sessions were supposed to go. I relaxed. I made each of their answers brilliant. I expressed gratitude for each of their corrections.

It was the best session we’d ever had.

Challenging your client as a coach is important. And sometimes you’re going to feel in conflict with them and the sessions may feel crunchy as a result. But it’s incredibly easy for your commitment to your client’s growth to become a grasping attachment to them being different.

If your session is going to crap start looking for what you’re holding onto. It might be an idea about how the session is supposed to be or it might be that you’re trying to hide how lost you feel. Find it and let it go.

6) Don’t decide the session is a failure –

I have literally had sessions I thought were total dumpster fires and my client said to me “Wow that session was so powerful!”

The truth is we don’t know the impact of our work. We’re not even in that much control of it. Our clients do a LOT of the work of coaching. So even if you think the session sucked don’t be too attached to that opinion.


Your job as a coach is to stand up for your client’s dreams, to be there with them as they make those dreams a reality, not to grade every session you have with them.

YES you should try your best to be a good coach and learn from your mistakes but in the moment the most important thing to do is stay with your client.

In some ways being willing to show up when the work is hard, your client is resistant, and the conversation is challenging is what being a coach is all about.

So be brave, take a breath, and do your best to land the plane anyway you can.

Managing Upset

The difference between breakdowns and problems

A problem is something wrong with the world. A problem happens to us, they land on us, and we have no choice but to complain about them and how unfair they are.

A breakdown is something we can declare. It’s something that has interrupted our commitment to something. For example I may be committed to waking up at 9am. A party might happen outside my house the night before, I wake up late and complain about this problem. Or I might notice that I had an unrealistic expectation (“nothing will get in the way of me going to bed”) and so I declare a breakdown in my commitment by acknowledging that something is occurring to me isn’t the way that it should be.

Once I declare my breakdown I can acknowledge my upset, I can record the facts about what happened, and I can get into action around my commitment.

Very often the breakthrough is on the other side of the breakdown I’m avoiding. For example I might want a breakthrough in intimacy with my partner, but I’m afraid to talk to them about it because they might get upset or defensive. This would be a breakdown. One that I’m avoiding. So I survive the problem. Once I’m willing to be with the breakdown (the difficult conversation, my partners feelings, etc) then I can get access to the breakthrough created by having a conversation around intimacy.

Breakthroughs are a creation of something beyond the context of what I currently see is possible. They are something that get created when I expand or deepen my context through declaration, commitment, being with breakdowns, and revealing blindspots.

Part of why breakthroughs follow breakdowns is because it’s in the breakdowns that our blindspots get revealed.

The Most Common Types of Black and White Thinking for Coaches

It’s never ok to give your clients advice.
You should never ask the questions why?
You should never deal with matters a therapist might.
You shouldn’t promise results you’re not sure you can deliver.
You should never work with a client that’s hard to coach.
You should never talk more than your client.
Your worth and your fees are related.
You should always be good when you coach your clients.
It’s a bad thing if a client wants to quit.
It’s a bad thing if you hurt your client’s feelings and you should avoid it at all costs.
The best coaches make the most money.
Coaches that charge a lot don’t care about their clients.
Making money and being of service don’t mix.
If you have a motive to sign clients it ruins your attempts to serve.
If you raise your fees you’re limiting who you can serve.
Coaches that market themselves are only out for money.
Coaching and consulting are totally different and consulting should never happen in a coaching session.
Coaching and teaching are totally different and good coaches don’t teach their clients.
Every coaching session should end with a homework assignment.
Every coaching session has to start with a clear desire and end with a clear outcome.
Accountability is key in coaching.
Accountability has no place in coaching.
The coaches with the most training are the best coaches.
The longer you coach the better you get.
I should be smooth when I sell to my clients.
It’s bad to be awkward when I coach or sell to my clients.
Being a beginner coach is bad and means most people won’t trust you.
Certifications are crap/essential.
If there’s something in it for you it can’t help your client.
You should never bring your personal life into your coaching.
Good coaches never upset their clients.
Making six/seven/eight figures means something about who you are as a coach.

(share your favorite one below)

None of these things are absolutely true about coaching. Some point to places to start, but in the end, all of them limit you as a coach. A master learns the rules so they can break them. A beginner treats rules like religion and never learns to let them go. Please insist on becoming a master coach.


Black and White Thinking — A Common Problem With New Coaches

Often when I talk to new coaches they get caught in black and white thinking about what good coaches should and shouldn’t do. 

– You should never ask a client why? 
– You should only ever ask questions. 
– You should never teach a client.
– You should never give advice. 

These guidelines are helpful when you’re starting as a coach.

– It’s easier to talk at a client than explore with them. 
– It’s easier to give advice than be curious. 
– It’s easy to ask why when you can’t think of something better to say. 

But these guidelines are simply guidelines and too often they become a religion for new coaches. Soon enough they are zealots preaching the gospel of pure coaching and the ICF standards. 

The best coaches I know push the boundaries of coaching while acting with a high level of integrity. Sometimes from habit but more often with conscious choice. Generally, they abide by the principles of what makes coaching work, but they aren’t bound to them. 

They see all the gray in between the lines. So if you’re new to coaching YES listen to the guidelines, try them on, if they feel hard to implement GOOD! That means you’re getting better as a coach. 

But don’t fall into black and white thinking. There are no rules to coaching and that’s the best and worst part about it. Your clients need you to be flexible enough to help them while maintaining enough integrity not to get lost. And learning how to make your way through the gray is essential is you’re going to truly become a masterful coach. 

What To Do When You Want To Quit Coaching

At least a couple times a year, I want to quit coaching. 

The clients are so annoying, they don’t want to do the work, they don’t want to change, and I start to feel like being a coach is pointless. 

The money (while good) is unreliable, it feels like I’m always just a few canceled contracts away from being stressed about money. Sometimes I’ve got plenty of prospects other times it feels like I only have a few. 

The work (while rewarding) is super difficult. I have to be the constant stand for deep possibility for each one of my clients. Even when those clients are being asshats. I have to do this even when I feel like I’m not present to much possibility in my own life and in the world in general. 

Wanting to quit is a normal part of life. 

During my marathon, I wanted to quit. 
During most of my long term relationships, I’ve wanted to quit. 
Hell even while writing this post, I wanted to quit. 

Stepping into anything worth doing creates tension. 

There’s the desire to complete the task, to keep going, to do the work, and the desire to get out of the tension, to take the day off, and do something easier or more enjoyable.

Getting out of the tension always feels pretty good. At least for a moment. 

Before the desire to quit shows up I feel this pressure to execute, then a thought occurs to me I could quit! and a wave of relief comes over me. I could be free of this whole thing if I just walk away. 

But of course, whenever I do this I eventually look back and wonder, “Why did I quit?” If I had just kept going I would have:

  • Written that book
  • Learned something about myself
  • Created something I was passionate about

So while the tension is uncomfortable, removing it as a strategy rarely leads to lasting satisfaction. And yet in the moment, it feels so tempting. A temptation I’ve given into so often I can hardly imagine listing all the things I’ve quit, though I can start with a sample:

Singing in groups
Writing my first book on coaching
My last engagement
Brazilian Jiu-Jitsu
Rock climbing
Learning german
Learning Spanish

I could go on . . . and on. . . and on. . . 

This brings me to my desire to quit coaching. . . or anything else

Coaching as a profession is all about sitting in tension. 

I sit in the tension of my client’s desires. 
I sit in the tension of conversations around commitment.
I sit in the tension of a client having paid me and a sense that now I owe them some form of transformation. 

Like I said. A lot of tension. 

And if I think of that tension as a burden. If I come from a place of needing to prove myself then it’s not worth it. 

There are a lot of easier ways to make money. A lot of easier ways to prove myself. 

But when I let all of that go. When I just remember what it’s like to be with someone as their life and the way they think about the world changes. My desire to quit fades. 

And that’s because I’ve found my calling, a practice where my purpose can fully manifest, a path that demands everything from me. 

My desire to quit is a part of that. A human part. And it’s a part I’ve learned to love and accept. 

So when I want to quit I remind myself that the reason I love coaching is because of the tension, the pressure, and the possibility. 

But you’ve got to decide if that’s enough for you or not. 

So my advice for you. If you want to quit sometimes is this:

First, let go of any idea that you’re a failure if you quit. 
Quitting takes courage and commitment. So let the shame go, it will just cloud your judgment. 

Next get really clear on why you’re quitting. 
Maybe it’s because you’ve decided that you feel called to a different kind of work.
Maybe it’s because you actually prefer working for someone else (which by the way most people secretly prefer).
Maybe it’s because coaching asked you to become someone you don’t want to become. 

The reason doesn’t matter. What matters is that you get clear on it. 

You were creating yourself as a coach. Now you’re going to create yourself as something else. Not because creating yourself as a coach is hard, but because you feel called to create something else. 


Don’t quit. Even a little bit. 

Go outside, take a walk, and remember why you started this. 
Feel the tension of what it means to be a coach. 
The annoying, hard, challenging, tension of it. 

Feel the heartbreak of clients who resist change (just like all humans do). 
Feel the discomfort of asking people to commit to something. 
Feel the challenge of declaring you’re going to help someone change their lives. 

Feel it all and choose it. 
Shake off the excuses. Love yourself. 
And choose it. 

The whole big ball of wax of it. 
And get back to work. 

There’s nothing wrong with wanting to quit. 
It’s normal. 
Expected really. 

It’s why you need a coach. 
It’s why you need a community. 
It’s why you need other people standing up for who you are. 

If you want to quit, do it. 
And if not, choose back in. 

It’s this simple act of choosing back in, that separates those who make it from those who don’t. 
It’s an act I do every day and have to do in real earnest a few times a year. 

Every path worth walking will give you the desire to quit. 
It’s what you do with that desire that matters. 

Whatever you choose. I believe in you. I hope you remember to believe in yourself too. 


You Don’t Have To Be An Expert To Be A Great Coach

How can I help someone build a multi-million dollar business if I’ve never done it?
How can I help someone with their law firm if I’m not a lawyer?
How can I help someone have a dope relationship if I’m still single?

I hear this kind of thing a lot from coaches. I get it. I mean I wouldn’t want to learn how to cook from someone who couldn’t make toast. I wouldn’t want to learn guitar from someone who can’t play basic chords.

But coaching isn’t like cooking or guitar.

To be a good cook you need to do cooking. Because you have to learn the nuances of making food in order to teach it to someone else.

With coaching you’re not teaching someone a skill. You’re using a totally different set of skills to help them improve their skills.

Skills like:
– Observation
– Curiosity
– Contextualization
– Empathy
– Analysis

Just to name a few.

But even more important than those skills… you’re being someone for your client.

You’re being a stand for possibility. Which just means you choose to stand in a place where you can see that so much more is possible than your client realizes.

In the movie, a Star is Born the famous singer sees a young singer with talent performing somewhere and takes an interest in them. The famous singer is standing in possibility. They see that so much more is possible for this young singer then they even realize. More so, they have the ability to draw it out of them.


And you don’t need to be a famous singer to do it.

What you need is an intimate understanding of possibility. What you need is an experience of someone standing for your possibility.

What you need is practice in the art of being with someone, finding out what they want, figuring out what’s in the way, and supporting them to take on the steps and beliefs. It’s a whole different set of skills than building a million dollar business or running a law firm.

And it’s why I coached a CFO at Nokia.
A CEO of a digital marketing agency in Peru.
A writer with work in the NYTimes
without ever doing ANY of these things.

The skill they needed to do their job was irrelevant to the skills I needed.
I never let a client’s desire for something I can’t do, stand in the way of what I see as possible for them.

If you’re wondering how you can help these people.
The deeply felt confidence you get when you realize you can choose to stand for anybody’s life, and possibility is irreplaceable.​


PS The Spring Dojo is already over half full. If you want one of the five remaining slots. Please let us know. It’s the ONLY dojo we’re running in 2021 right now.

Is This The Year?

You’ll become the coach you dreamed of . . . making a living, doing the work, hiring that coach you admire?

You’ll become the leader you pretend to be . . . empowering others, stepping outside the pocket and taking a risk, putting yourself on the hook?

You’ll become responsible for not just who you want to be, but who you are right now, fame and flaws?

It may be and it might not . . .

But one thing is for sure, it won’t happen through grand pronouncements or resolutions. It won’t happen because you made a big post about it on JAN 1.

It will happen through a thousand little choices, a thousand little practices. And perhaps the most important practice of noticing when you’re not being it, without shame, without judgment, without avoidance, and then choosing to return.

Performance is NOT morality.

Failure is not a sin. It’s not even that significant.

I wish for you a year of practice, more than victory, or success, or millions of dollars, or followers.Because there is no separation between Practice and Mastery. Practice and Success. Practice and Liberation.

Practice is mastery, success, and liberation.

It’s all the same.

May you practice well.

And thank you in advance for supporting my practice and very often without even knowing it, for being my practice as well.


The Best Coaching Sessions Are Boring

Don’t get me wrong. I love it when a session with a client is full of emotion. Maybe they burst into tears and are on their growth edge, or they are so fueled up with energy that they cannot wait to take on a new challenge.  If I’m honest the best coaching sessions—the ones that have the most lasting impact—are the boring ones. But this is hard for most coaches to understand, especially new coaches.


The difference between swings and homeruns. 

If you want a truly masterful coach you’ll likely be impressed by their ability to cause big tectonic shifts with relative ease. In the world of coaching, you might call these home runs. 

They are:

  • The questions that crack a client open
  • The reframes that shift perspective in a big way
  • The words of appreciation that open a client’s heart

I love home runs. I remember watching coaches like Rich Litvin, or Steve Chandler, or Michael Neil, or Byron Katie and many others. And being blown away by their home runs. 

And I remember going out and trying to replicate them. 

I’d stare intently at the client willing them to cry
I would pluck on heartstrings
I would give bold speeches

A lot of this ‘worked’ in that it created a reaction in my clients. 
But much of it wasn’t great coaching. 

Slowly I began to notice something. While the home runs were great, they didn’t lead to change. 

So I went back to the drawing board. I began watching sessions in a new way. 
I stopped looking for the home runs. I started watching in between them. 

Eventually I began to see what these great coaches were doing.
They weren’t trying to hit home runs at all. 

They were trying to take swings. 
They would listen and take a swing. 

Sometimes it hit, sometimes it didn’t. 
But that was ok. 

They would learn from the last swing. 
They would listen even more closely. 
They would lean into the client. 

And then they would swing again. And again. And again. 

With each swing, they would notice what landed or what didn’t. 
No one swing mattered that much to them. Their swings were graceful, elegant. 
They were mostly unattached to hitting a home run, they swung because they loved to swing. 

That’s when it hit me. 

If I want to be great, I need to learn to swing. 
Even when I don’t hit the ball. 
Maybe even especially when I don’t hit the ball. 

I need to learn to swing. 

And sure enough, the better I got at taking swings the more home runs I hit. 

But it was only by letting go, by not needing to hit home runs, and by letting myself be boring that I saw the results. 

So now, when I have a session that’s all swings and no hits, I don’t worry about it as much; 
I simply let myself swing. I feel the motion of the conversation. I enjoy the sound of dialogue. I know that if I keep swinging and paying attention, eventually something will open. 

A whole session of swinging can feel boring. But these sessions are often the ones that create the momentum, lay the groundwork, and inspire the big changes that come later on. 

Please don’t get attached to hitting home runs, or making your clients cry. 
Focus on the swing, the being, and the way you stand for your client. 
If you put your attention there not only will you get better home runs, but you’ll also enjoy being a coach so much more. 

Coaching Only Takes 3 Steps

The Surprising Truth: Coaching Is Actually Very Simple

If I want to sell you on coaching, I will make it seem like it’s super difficult. And then like a magician (or a con artist) I’ll remove the barriers. I’ll tell you that I’ve got a magical map through the forest. One where all the traps and beasts are marked on it. If you use my map, you’ll be nice and safe.

But this is a lie.

Coaching isn’t complicated. It’s actually very very simple.

This is how coaching works.

First, you become possibility. You don’t talk strategy and offer suggestions. When you sit in front of the client you believe in and embody that anything is possible for them.
You breathe it. You embody it. You express it.

Second, you sit across from someone and you ask them what you want.
And you keep asking them until you can feel you’ve got it. You’ve got a hold of what they really want. Not the strategy, the thing they think they can get, or the thing they think they should want. But the thing they actually want.

Third, you find out what keeps them from getting it. What stops them or how they stop themselves. You explore it until you understand it completely. Until both of you know this thing with the intimacy of your own breath.

That’s it.
Be possibility.
Find out what people want.
Becoming intimate with what’s in the way.

It’s not complicated.

All the tools, questions, and processes are really just designed to help you do that.
Be possibility.
Find out what people want.
Become intimate with the obstacles.

So simple and also quite challenging. The simplicity itself is perhaps the biggest challenge.

That’s why at some point learning more doesn’t help.
The only thing that helps is practice and being.

The practice of keeping it simple.
The practice of being possibility.
The practice of standing for your client no matter how they show up.

Don’t make it complicated so you can avoid the challenge.
Keep it simple, so you can fully embrace it.


PS If you are ready to embrace the simplicity and become a master coach, apply for the spring 2021 dojo here.

The Origin Story of the Dojo

I remember the second coaching intensive I ever attended. I was full of myself. I had just crossed the six-figure threshold. I was a member of the high-level mastermind everyone wanted to be a part of. I had expensive new shoes. 

And I noticed something. There were a lot of coaches around me who didn’t feel that way. Coaches who had been coaching for a long time, years more than me, and yet they were stuck. I couldn’t figure it out. Part of me thought well I’m just hot shit that’s why I’m doing so well, but another part of me knew that wasn’t true. I knew I was good but I didn’t think it’s because I was super good, I figured there had to be a reason, but I couldn’t figure out why. 

Until we did speed coaching. 

We sat in opposite rows, we coached, one row got up, moved down one seat, and we coached again. It took me three sessions to realize that most of the coaches were not great. I mean they were fine. They asked interesting questions, they leaned forward with a tentative eager look, but beyond that, there wasn’t much. 

Each session felt formulaic, heavy, constructed, and boring. There were a few highlights but mostly I was blown away that the majority of the coaching I experienced was at best, mediocre. Yes, I was being cocky. Yes, I had absurdly high expectations (especially then). Yes, I know fast coaching isn’t the same. But the impact was the same and I had my answer. 

The reason why most coaches were struggling was because their coaching was just fine. Not bad, not great, but fine. 

And I started to wonder how I could fix it. 

After all, the enrollment techniques most of us were using—sometimes called relationship selling or the prosperous coach method—put A LOT of attention on your coaching. 

The idea was that you connect with people, find an opening, invite them to experience coaching, and then sell them based on that experience. Which works great if you 1) have a super charming personality and/or 2) you create a really incredible coaching experience. 

If you don’t do either your results will end up being as mediocre as your coaching. 

So I started to think about how I could help people get better.


The Motivation of Debt

A few months later I formed a small mastermind group focused on retiring debt. The 3 of us all had built up a fair amount of credit card debt investing in various programs. So we started to meet on a monthly basis to talk about our money, how we spent it, and what we might do to earn our way out of the hole we had found ourselves in. 

I noticed that I was mostly focusing on signing one-on-one clients, which was fine, but I was only paying off debt slowly. I wanted to pay off my debt fast. So I came up with the idea to build a program, something that would allow me to pay off a big chunk of debt all at once. 

I thought about creating something for coaches. A short group program that would have a big impact on them. I wanted to help coaches get better. I wanted to give coaches a taste of what I had experienced at the monastery, but I wasn’t sure how. 

I shared the idea with the group and they liked it. My partner at the time, Christina (who was also a member of the group) said she’d be down to collaborate with me on it. 

At first I just wanted to have people practice coaching. I also wanted them to meditate daily and learn to study their own mind while simply sitting. It wasn’t much more than that. Just meditation and practice. 

But Christina pushed me to create more structure. So we started talking about what had helped us become better coaches. We remembered some of our conversations where we had traded sessions and spent a long time afterwards talking about what did and didn’t work in the sessions. 

We shared feedback with one another and that feedback, which was honest, kind, and curious helped us so much. 

I had encouraged her to be more forceful, to tell clients that she wanted to work with them, and to add more structure to her sessions. She had invited me to be more playful and to bring more joy and laughter into my sessions which could often feel very heavy and serious. 

This feedback grew over time and became more precise as we got to know each other’s coaching. 

We considered how we could combine this element with my monastic experience. Soon we were riffing on ideas. We talked about the icons of Zen and which icons invoked this kind of practice. That was when we started talking about Samurai and how they were both rooted in the zen tradition while also focused on improving their skills in community. 

It became the seed of what would become the Samurai Coaching Dojo


Happily Ever After? 

Of course that’s not the end of the story. Christina and I spent years refining the dojo. We learned a lot each time we ran it. Christina left the dojo, and Matt came on as a Sensei.  Matt and I have continued that tradition of simplifying and clarifying the message. Finding new ways to express this simple idea that it’s through practice and feedback that mastery is created. 

But it all started with a simple observation and intention to help coaches while also helping myself. 

I still believe deeply in the core of what the dojo is: an idea rooted in Zen. In Zen they call sitting Zazen. It’s often called practice realization because they don’t see any difference. Practice is enlightenment, enlightenment is practice. 

And that’s what I’ve always tried to keep at the center of the dojo. It’s not about the teachers, or the other students, or the model of coaching, or the tools and techniques. It’s about the practice. 

When you engage in the wholehearted practice of coaching, you can’t help but get better. You can’t help but feel more confident and deep. The trick is the wholehearted part. 

Most things simply engage your mind, but I’ve always tried to make sure the dojo engages every part of each coach that steps inside it. I haven’t always succeeded, but the core of the mission feels just, if not more, important than it ever has been. 

So that’s the origin of the dojo and that’s why I keep choosing to do it every year.