The Coaching Habit With Michael Bungay Stanier

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Join us in today's episode because my guest will paint today's conversation with multiple colors with his insights. Michael Bungay Stanier is the founder of the Box of Crayons and author of the best-selling book The Coaching Habit. Michael explores the role of persistence in his life journey, which allows him to disallow any rejection that will hold him back. He also explains the power of keystone conversation in unlocking deeper understanding and building trust within working environments as well as the contents of his latest book, How To Work With Anyone.


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The Coaching Habit With Michael Bungay Stanier

It is my honor and pleasure to introduce you to my guest in this episode, Michael Bungay Stanier. Michael is best known for The Coaching Habit, the bestselling coaching book of the century and recognized as a classic at this point. His book How to Work With Almost Anyone shows how to build the best possible relationships with key people at work.

Michael was a Rhodes scholar and was awarded the Coaching Prize by Thinkers50, the Oscars of Management. He's also the Founder of Box of Crayons, a learning and development company that has changed hundreds of thousands of managers to be more coach-like organizations from Microsoft to Gucci. It is truly a pleasure to welcome you to the show, Michael.

I'm happy to be here. I love a good campfire. If it is virtual, so be it. I'll take it.

I always like the in-person but we have to sometimes stick to the virtual for now. First of all, thank you for all that you do in the world. It's an inspiration and truly an honor to have you here because you've made an impact on so many lives, including my own.

I appreciate that. Thank you, Tony. For many years, I've had a bigger personal mission. It is slightly over-the-top language perhaps but it's to infect a billion people with the possibility virus. That feels impossible but the unexpected and delightful success of the coaching habit amongst other things is I'm not even close to a billion people but I've got a bunch of people who bumped into me in my work, which is pretty cool.

Looking Back

You do one person at a time and it starts to build from there. You hope that it's like the telephone game. One person passes it on to the other person and then they’re like, “You should check out this guy.” It's great. As we do in the show here, we reveal people's stories through what's called flashpoints. It’s points in your journey that ignited your gift into the world. I'd love to have a journey through your background and talk about your flashpoints. It’s what you call to share. Start wherever you like. I've had people share stories that predated their origin, which is interesting. I would like to hear what are the things that made you who you are making such a big impact in the world. We'll pause along the way and see what themes are showing up.

One of my favorite quotes is, “Inspiration is when your past suddenly makes sense.” It's not always the sliding door moment, a-ha moment, or I'm-walking-on-triumph-on-stage moment that makes the difference. It's this random amalgam of decisions and non-decisions, good luck and bad luck, and this and that person that nudges you to become the person that you get to be. I would pick three things that have been strongly influential in the shape of my life.

The first would be in having a strong role model as my dad in particular. Both of my parents are great but my dad was a gentleman who was committed to a community, was a volunteer, and was non-patriarchal. Even though he was the main wage earner in my family, he did half the cleaning and cooking. It was a real shed commitment to parenting from mom and dad. I look a bit and I sound a bit like my dad but I also feel like I've inherited a bunch of his good qualities. That's one.

The second one would be trying to win The Rhodes Scholarship and doing it twice. I played for one year and didn't even get an initial interview. I was like a bummer because they told me that everybody gets an initial interview. When I didn't, I was like, “That's disappointing.” I applied a couple of years later with more focus, determination, and commitment. Winning The Rhodes Scholarship pulled me out of Australia and out of a possible career as a lawyer, which would have been a disaster. I met my wife, Marcella, at Oxford University where I am studying. That was pretty significant.

The Virtual Campfire | Michael Bungay Stanier | Coaching Habit

The third one, which you probably would have to say, is The Coaching Habit. It’s a story of rejection. I spent 4 or 5 years pitching it to a publishing company that published a previous book of mine. They keep turning it down. Finally, I was like, “This is it. Publishers will be damned.” They're like, “We're still not going to publish it.” After a certain amount of licking my wounds, I self-published it. It was February 29, 2016. That book has been instrumental and shifting a bunch of good things in my life as well. Those are the three headlines for you.

Persistence is a word that you're very familiar with. It seems to be a theme that shows up for you and not taking rejection as something that's going to hold you back.

I've had plenty of rejection that has probably dented my confidence and held me back a little bit but mostly, where I am wired to go is about me. Often if they're rejecting me, they’re idiots. It's a good healthy self-esteem. I sign off my emails and newsletters, “You're awesome and doing great,” which has become something of a catchphrase for me.

That's true about me. I am awesome and I'm doing great. People are rejecting me. I don't typically take that as I'm not good. I take it as either I'm not right for this moment or they're idiots. There's been a number of times when I've backed myself to do the thing or be the thing, and they've paid dividends for me.

If all those people who rejected you in the past are reading, they're like, “Am I an idiot?”

The publishing company that rejected me published a book of mine called Do More Great Work. It sold close to over 50,000 copies certainly and nudging towards 100,000 copies, which is pretty good for a book. My first book sold less than 5,000 copies. It was not a bust-out hit but it's also a pretty solid book. In the end, they turned me down and it's probably because I had good business model reasons that they're like, “We don't do business books so much.” Maybe I was getting clear on that. At the same time, my books sell a million and some copies. A certain part of them is like, “You missed this opportunity of a book.”

It has me thinking about Daniel Pink's book WHEN, which is this sense of sometimes it's a matter of knowing, “Is it the right time for this to be coming to the world?” There's a lot of congo in self like, “When is the right time for two people to come together and two things to match up?” If you have patience and persistence, these things come together eventually.

A book I like is Seth Godin’s book The Dip. As with all assessment books, it’s pretty short. It starts with a key message to it. Its key message is we often quit too soon. To get to the other side, you often have to get through the dip. At the same time, I probably hold a slightly broad of you, which is most of us have a bias one way to be too loyal or flighty. We'll either stick with something too long. We're like, “No. I'm going to keep going.” No, you should have stopped that. “If it's the wrong hole, stop digging,” as the saying goes.

Some of us quit too soon. Trying to guess where the perfect moment is as easy as investing at the bottom of the stock market and selling at the top of the stock market. Everybody wants to do that in theory. In practice, that's elusive but it's useful to know what your bias is. Do you tend to stick around too long or leave too soon? When you're faced with the moment, which is hard, become aware of your bias and then make the best choice that you can.

You get better after a while. I think of it as almost reading waves. If you've ever surfed, you start to get to this place where if you're just getting started with doing something, you tend to be anxious like, “I'm going to jump in and start paddling like crazy.” You find yourself exhausted. What happens is after a while, you start to read better and say, “I’m going to slow down. This is not the right one for me. It’s time for me to take the next one because it's even better.”

Here’s the challenge. Surfing is famous for asking you to be in the moment and present to what's going on. You're like, “I am watching a wave and I am treating each wave as the next wave and making a choice if I buy my board and paddle or do I ride the swell and let it go?” Whereas with the stuff that's happening in our lives, it’s often harder to be present in that because it's messier, bigger, and more complex. What you're trying to do is become more present and notice yourself, your patterns, and the moment and go. “If I'm seeing this now, what is this telling me about me and my choices in the past? What is it suggesting to me that I might make a choice this time around?”

Becoming A Coach

How did you arrive thinking about coaching in general? You are amazing at this. Whether you like to own that or not, I'd love to hear about your journey into getting into the world of coaching.

There are two levels to it. One level is I am very good and one level is I'm pretty good. I don't coach a whole lot. I don't have a coaching practice or clients. I probably have lots of coach-like conversations because I'm inherently nosy and curious. I know how to ask a good coaching question. I don't self-identify as a coach, which is surprising because I've won awards and stuff in that field. What I am good at is teaching and making the idea of coaching and the tools of coaching a little more accessible and democratic if you like.

I tried to be a coach. I trained as a coach. I got certified. I built up a coaching practice and then went, “This isn't the thing I love to do.” It doesn't have the scale that I'm ambitious for. I can infect a billion people with the possibility virus by having a coaching practice of twenty people. It doesn't scale and reach like that. Whereas if I write a book or give a talk, it's more chance of it rippling out. The access to that world was as a teenager going to university and joining something called Youthline in Australia. It's a youth crisis counseling service.

I did some training with them on using Carl Rogers' work. It’s a Rogerian counseling. In effect, it is like staying curious. Expect that their first answer is not their only answer and best answer. There's probably more going on to slow down the rush to give advice. All of that is stuff that shows up in my teaching and then my philosophy to that. I volunteered there for a fair while. When coaching started becoming a thing, which is for me in the ‘90s, I was living in London but it was starting to take off in California or it felt like. I was like, “Californians are a weird bunch, woo-woo, hippie, touchy-feely types.”

I was in England, which is all that skepticism and cynicism are very non-Californian but I was conscious of it and interested in it. I started talking to my clients about coaching rather than consulting, which is what I was at the time. When I moved to Toronto in 2001, I trained as a coach. I built a practice and dismantled the practice. At the same time, what I was discovering is that I'm a better teacher, facilitator, and explainer of complex things and trying to make them feel simple and accessible for people, which is adjacent to coaching.

Coaching in some ways is another form of teacher. It's more interesting if you look to be a teacher or facilitator and use coaching skills as part of how you make change happen. I started writing books. The Coaching Habit is my fourth book or something. It wasn't my first crack at it but that became the breakthrough book in part because it simplifies what coaching is. I’m with coaching for people who aren't coaches.

If you're in the coaching world, you're like, “I love coaching. It's amazing.” That can be true. If you're not in the coaching world, it's like, “It’s full of DP woke, touchy, feely, and woo-woo people.” There are all sorts of reasons where you're like, “I'm not a coach or that type of person.” I'm like, “For me, coaching is staying curious a little bit longer.” Don't be a coach but be more coach-like. Make that part of the way you show up in the world. Part of the success of The Coaching Habit is it makes people go, “If this is what you're talking about, that's not too odd. I can give that a crack.”

Be more coach-like. Make that part of how you show up in the world.

The Coaching Habit

I think of it as almost being uncomfortably curious. Some people are not comfortable being that curious and asking questions that go a little deeper than normal. What I love about what you shared in general is this idea that people think of The Coaching Habit as being your entry into the world but the reality is it’s not. It's far beyond it. You've been doing a lot of other things that build up to that.

I’m like everybody. My overnight success only took twenty years. That's not even interesting. This is true for every overnight success pretty much.

There's an evolution that we all have to go through. Sometimes, we think, “It's X,” but X becomes Y and then Z. Before you know it, there's an evolution we have to go by. Starting on a path allows you to explore what's next. What I'm hearing from you is the sense of opening yourself up to see what might be possible once you start to pull the threads of things.

You can always construct that story in retrospect. It never feels quite that tidy when you're in the hurlyburly of it at the moment but somebody shared a metaphor with me, which I like. It's called the Helsinki bus route.

Tell me more.

If you look at the map of the Helsinki bus terminus, and I'm making all these facts up but metaphorically, this is true, for the first 5 miles, all of the routes cover 1 of 6 different routes. Every route in the first 5 miles goes along the same roads as most of the other buses. There's only after 5 miles the route starts to break apart, diversify, and head off to East Helsinki or Southeast or Southwest Helsinki. The point this person made was that often, we give up too soon.

We get off the bus like, “I've been on this journey already.” You hop off in the first 3 miles. There's a way where you persist and start going, “We're in new territory.” That's when stuff starts to emerge. You start to figure it out. The Coaching Habit came out in 2016. I probably was teaching stuff around coaching for many years before that.

If you told me, before I founded Box of Crayons, the training company, that it would have a focus on helping people with practical coaching skills, maybe but I don't know where you're getting that from. I had no specific interest in that. It takes us back to where we started, which is inspiration is when your past suddenly makes sense.

Personal Struggles

I love that saying too because inspiration is important to me. My business is called Inspired Purpose Partners. Inspiration is the core of what I do. You have to follow that and start looking back at that. It's cool. Tell me more about the struggles along the way to getting to what you're doing. Were there any other moments when you started to question like, “Am I on the right path? Should I have been a lawyer?”

I haven't had a lot of moments of self-doubt around that and maybe because of two things. One is I have a certain wiring in my brain that is very much about what's next, moving forward, keep moving. I don't spend a lot of time looking back with regrets. I love Jim Collins’ metaphor where he's talking about strategy. The way you figure stuff out is you fire bullets and then a cannonball. Firing bullets is like a little experiment. They figure out what the real target is. Once you hit the target, you're like, “I think this is it,” so commit to that.

I've had good moments of doing that. If I have moments of regret, it's like, “I half-assed that,” rather than committed to it. One of the reasons The Coaching Habit took off is I was like, “I'm committed to two years of pretty solid podcasting, showing up, and talking about this book.” I was committed to getting it out into the world. The second helpful thing is I'm pretty good at staying aware that if you commit to the process and outcomes, they work or don't work. What can you do?

If I think to myself we made the best choice we could and committed to it as deeply and powerful as we could, then I'm mostly happy. It's easy to look at my resume and go, “Here’s an award, a book, and a Rhodes scholarship.” There's a whole bunch of glittering things on the resume. It's the minor failures that fill my life. You call it a failure. Sometimes, it's mediocrity. It wasn't terrible but wasn't any good. Part of the deal is it accumulates scars and you try stuff out. You hold it all pretty lightly.

I said to my team, “It's quite hard to disappoint me. If you've given it the best shot, the failure doesn't disappoint me but at the same time, it's hard to make me content.” I'm always quite restless as to what the next thing is and where I'm heading. That's a difficult tension for people to manage who work with me because I'm like, “It's not that he’s worried about the success, yet his constantly curious about what the next success might be.”

When you think of an orientation to forward, commitment to process over outcome, or that ongoing answer if you like I have for me, which is I'm awesome and I'm doing great, it means that I don't take too many things personally because it's like, “Is it going well? I'm awesome and I'm doing great. Is it going badly? I'm awesome and I'm doing great. Is it not going anywhere particularly? I'm still awesome and I'm doing great.”

It's like you're not attaching your well-being to whether or not this new experiment is going to work out. I love your mentality about that because it's putting these experiments out there and seeing what happens. The worst thing that could happen is not trying. If people don't venture, then nothing gets gained.

That's true. It's the worst thing that can happen but it's a choice you have in your life, which is like, do you want to play the game or stay on the sidelines? You can make cases for both of those choices but for me, I'm trying to play a game and I'm more interested in hanging out with other people who are trying to play a game. I have two nieces and they’re very different. One is out there having adventures, making mistakes, finding herself in sticky situations, and extracting herself from her. She's fantastic and wise beyond her years. She’s somebody who I'm like, “Hanging out with you would be cool.”

I have another niece who's perfectly lovely. She's said to me once, “I only do things that I can win at.” That breaks my heart a little bit because that's the least interesting thing to do, the things that you can only win at. You don't learn anything there. You just win. It’s boring. I was like, “You're not yet that interesting because you haven't collected some stories and scars yet.”

There's something about what you shared. People stay in their comfort zone when they do that. Honestly, what we need to be able to do is get uncomfortable. I'm always playing with ideas for articles. I'm like, “People often say they want to get uncomfortable or get out of their comfort zone but do they really?”

It’s an intuitive thing to do. Your whole brain's modus operandi is to say stay in your comfort zone. Your brain is wide through tens of thousands of years of training. It's like avoiding danger and embracing comfort. It's all very well to go on or get out of the comfort zone but we are biologically wired not to want to do that. You have to hack your systems to find the courage to step out to the edge.

Hack your systems to find the courage to step out to the edge.

Before we move on to the next part of our conversation, is there anything else in terms of flashpoints or moments that you wanted to share stories, I'm sure billions of them, that have made you into the person you are?

I'm not sure. I don't think so in particular. I do think it's more the gradual accumulation of small things that you do that laid a foundation for who you are. John Gottman writes about relationships. One of his great books is called The Seven Principles for Making Marriage Work. It's a great book to read in general whether you're married or coupled up. It’s how relationships work.

His time is through their lab. They can tell in a couple of minutes whether a couple has a long-term future or not by the ratio of positive to negative interactions. Not just positive things that have been said but do they make a bid, do they accept the bid, give or take? It’s those small little things. It's not the wedding that is the turning point. It is the daily interactions.

There is a 7:1 ratio of positive to negative and that's what builds success. There's probably an analogy in terms of what it takes to live a good life, which is you have moments like winning a Rhodes scholarship, having a dad, or publishing a book that changes things. They change things and it's the day-to-day interactions where you cement what matters most to you. Your values are expressed.

If you think of it as the EKG of sorts, there's a spike but it's also how you're dealing with the times in between that make the difference and how you are navigating the space between that makes for the impact in your life. I want to shift gears and talk a bit about your book, How to Work With Almost Anyone. You always have had these long titles since The Coaching Habit. Tell us a bit about that book. It was fantastic but I want the audience to have a sense of like, “Why this book is so impactful?”

How To Work With Almost Anyone

The Virtual Campfire | Michael Bungay Stanier | Coaching Habit

The key behind it is that our working relationships determine to such a great extent the happiness and the success of our work. We spend most of our time worrying about the work and hoping that the relationship things sort itself out. People don't often have the tools to build better working relationships. Anything you can turn every working relationship into something is perfect. I do think every key working relationship has potential. Your goal is to try and find the best possible version of that working relationship.

Every key working relationship has potential. Coaches should try and find the best possible relationship and the best possible version of that relationship.

It's building on some of the ideas around psychological safety from Amy Edmondson and others and saying, “How do you build the best possible relationship?” The three core attributes are that it's safe, it’s vital, meaning alive, and it's preparable. I'm quoting John Gottman because I've been thinking about his work a lot in the context of the best possible relationships.

The key tool that's in the book is something called Keystone Conversation, which will sound obvious when I say it. Have a conversation about how you work together before you start working together or even have a conversation about how you work together in the middle of working together. Stop for a moment and go, “How do we do it? Are we bringing out the best in each other?”

In the book, there are five suggested questions you can ask and answer that can go to making up a keystone conversation. They give you a chance to say, “This is you and me figuring out how you and I best combine our experience, skills, strengths, weaknesses, and triggers to give us the best chance of a relationship that thrives, is fulfilling, and also gets the work done.”

I love the way you described it. This is one of those books that change the game for a lot of people because we go to work and expect, “If I don't like somebody or I don't get along with somebody, I'll avoid them or spend less time with them.” The reality is we spend so much time at work and oftentimes, we have to find ways to work better together. Instead of shying away, it's best to lean in and see how you can build a better foundation for that conversation.

You have a choice, which is, “I do nothing or do something.” Most of us do nothing so we have a whole series of slightly decaying and frustrating working relationships around us. If you think of your ten most important working relationships and you could make all of them 10% better, 10% more pleasant, effective, and thrilling, wouldn't that be good? He says rhetorically because yes, it would be good. That's not going to happen through good luck. It takes somebody to be brave enough to say, “Why don't we do something about this?”

That's a great way to look at it because a keystone is like a foundational piece. Having a foundational conversation that sets the tone for everything else is breaking the pattern that you ran. You're in a pattern of like, “This is the way things are, accepting it as is and doing nothing about it.” You're maybe carrying a burden of weight because of that and they're probably because of that. It's breaking that pattern and seeing why not make it easier. One of my favorite coaching questions to ask is, “What am I tolerating that I shouldn't?”

We have an amazing capacity to put up with a whole lot of BS. Sometimes, that's the name of the game but it's pretty useful to go, “What am I tolerating? Do I need to be tolerating this? Am I resigning myself to playing somewhat of a victim to a situation or a person that could be shifted in a way?”

You've gotten better with age.

Thank you.

Each book seems to build on each other and has gotten deeper into this sense that we can get better if we're willing to do the work and have those questions. What do you do next?

My problem is rarely, I don't have any ideas on what to do next. I have too many ideas on what to do next. Honestly, it comes a bit back to that infecting a billion people with the possibility virus. One of all the ideas I've got feels doable, difficult, and might be its best contribution to a billion people. One of the quotes from another book of mine called How to Begin is about helping people figure out what their next big thing is and what their worthy goal is.

At the end of it is a quote from Roca, the poet. His goal is to be deeply defeated by ever-greater things. I love this idea of coming back to this restlessness like we were talking about before. “What's the thing that's cracking me open, pushing me hard, and making me sweat?” In How to Begin, there's a line, “We unlock our greatness by working on the hard things.” I said, “How do I find the hard things that will keep trying to make me the next best version of who I might be?”

We unlock our greatness by working on the hard things.

It sounds like that book was written for you or one of those books that was targeted toward what you most wanted.

These books are written for me. You always end up writing the book that you need to read. I write it to figure out what the hell I'm thinking, learn from it as well, and try to embed some of these important tools in my life.

Advice From Michael

What is a lesson that you would like to share with others that you haven't shared already in the space?

Many of these useful lessons have been shared a bazillion times in different ways by different people because there are not that many essential truisms in the world that I've come across anyway. I have two things that I'm modeling over at the moment and who knows they may or may not be interesting or useful for people. The one is the more things I can say no to, the better I am able to say yes to the stuff that matters.

I'm easily distracted and tempted by all sorts of stuff. It goes against my nature to keep saying no to things but it turns out that being able to say no well is one of the great skills of life. You get a reputation for being strategic, being clear, and having boundaries. You create space for you to put your attention to the stuff that matters most to you.

The second being is I know lots of people a little bit. I'm always tempted to spend more time with the people that brought a sphere of my life but I realized that my happiness is more influenced by spending time with my top 20 or 40 people. How do I reorient to keep reinvesting the friendships I have and deepening them rather than keep adding new people to the, “I know this person a little bit?” I don't know how to do that. I'm still trying to figure that out. It's obvious and not obvious at the same time. That's the other piece of wisdom that I don't know if it's useful for anybody else but it's useful for me.

Book Recommendations

It was landing with me, especially the second one. It’s this feeling of having deeper relationships and connections with the people around us but also knowing that we can have an impact on others without having to artificially feel like we have to connect with them in that way. Instead, it's about knowing the people around you on an intimate level but also sharing messages with others to know that there's another way to be. First of all, Michael, this has been amazing. I have one last question to ask you and it's one that I asked every single guest. What are 2 or maybe 3 books that have an impact on you and why?

We’ve given a shout-out to a few already like John Gottman's The Seven Principles for Making Marriage Work and Seth Godin's The Dip. I'm a big reader. My wife's a big reader. I'm surrounded by books on the shelves or floors everywhere. There are three books that are significant for me. One is by an Australian fiction author, David Malouf. One of his early books in the ‘80s or maybe even the ‘70s is called An Imaginary Life.

It tells the story of Ovid getting exiled from Rome and moving to the ends of the Earth or empire, as it was then which is like in Romania, and his integration into a greater whole. It’s very poetic, short, and beautiful. It’s a nonfiction book, not a business book. I probably mentioned Bill Bryson's book, A Short History of Nearly Everything. It has this incredible gift of making science feel interesting. If you lost your love of science in high school because of the teaching, this will bring back some of the love because it's full of characters and metaphors. He's such a funny gifted writer. I might include that.

Self-help in business is the same as ones slightly differently framed. I might shout-out Austin Kleon's series of books but his first one is his most successful. It's called Steal Like an Artist. Anytime I'm writing a book, I'll often look at that book to go, “How do I write a book that's more like this?” It's wise, synced, playful, and beautiful. It's almost impossible not to finish it. If you pick it up, you will read the whole book because it's so short and compelling.

As an author, you're always going, “How do I get people to finish my books?” It’s hard to write it but it's hard to get people to buy them but even if they bought them, it's like, “How do I get them to start reading this?” We've all got books that we bought and have not started yet. “How do I get them to finish the book because everyone's looking to stop reading that book as fast as they can?” If I'm forced to read it from cover to cover, I'm impressed.

Closing Words

I love what you share. Everything was amazing. I resonate with a lot of things you shared but Bill Bryson has one that I haven't heard in a long time. I was a huge fan of Bill Bryson growing up. I've read every single one of his books. He's a brilliant writer.

His travel writing is laugh-out-loud brilliant.

There was one particular book that I remember about his childhood growing up in Middle America and it was so funny. I can't thank you enough for coming to the show.

My pleasure, Tony.

Thank you for sharing your stories and insights. I'm railing. My mind is blown up by all of the insights. Thank you for coming on.

Thanks, Tony. Thanks for having me along.

I appreciate it. Before I let you go, I want to make sure that the readers know where to find you if they want to learn more about you.

The hub is That's the website. From there, you get to all of my books and all the free stuff that comes with my books. You can find my social media stuff if you're interested in that.

Thanks again. Thanks, audience, for reading. I know you're leaving inspired and curious to go dig in and find out more. It's a wrap.

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