Forever Employable Stories: Michael Bungay Stanier, best-selling author of The Coaching Habit

Posted on December 7, 2020.

What struck me the most from the time I spent interviewing Michael Bungay Stanier, author of the best-selling book The Coaching Habit, was how he has repeatedly reinvented himself throughout his career. Whether it was deliberate choices he made to push himself into new and unfamiliar directions or random black swan events like 9/11 that changed the trajectory of his career, Michael took each direction with enthusiasm. It wasn’t always perfect. It didn’t always work out like he’d hoped but he pushed through, persevered, learned new skills and applied them on his next assignment.

This aptitude and welcoming attitude to learn continuously, to explore willingly and to unleash his curiosity has taken Michael all over the world, helped him build his own company and more recently produce a series of well-respected books that help others grow their own work and businesses. On top of all of his success he continues to be one of the more generous authors and thought leaders today. I can personally vouch for using many of the tactics Michael has kindly shared publicly around book marketing and growing a coaching and consulting business. There is so much to learn from Michael we fit as much as we could in our ~30 min discussion. Video and transcript follow below.

Watch it now:


JEFF:    Hey folks. I’m super thrilled to be doing another one of the Forever Employable stories. This time we have an amazing and incredible guest. I can’t wait to dive into it because a lot of the stuff we’re going to talk about is stuff that I’ve learned from him and that I’ve put into action to help me continue to build my Forever Employable platform. I’m super excited to have Michael Bungay Stanier with me here today. He’s best known as the author of The Coaching Habit and you can find all his works over at Thanks so much for joining me.

MICHAEL:        That is awesome. I’m happy to be here. I think of myself as forever unemployable. I guess that’s a different side of the same coin. I’m glad to be here.

JEFF:    It’s interesting you say that because I hear that a lot especially from entrepreneurial folks. Folks who have broken the mold and are trying to make a living a different way. They say, “Why didn’t you call it Forever Unemployable?” Tell me what you mean by that.

MICHAEL:        There’s two phases to it in my experience. One is an endless, an increasing frustration with having a boss. When I worked, and I worked in different companies, I was generally liked by my clients, by my peers, by the people who reported into me, and I was generally annoying to my boss. At a certain point of being an entrepreneur where you’re used having a way of working, a sense of autonomy, a sense of creativity, a sense of responsibility, it becomes very hard to imagine not having that anymore and having to report into somebody and fit into a structure. At a certain point, you just get turned and you’re like, “That’s it. I can never go back to the dark side or light side” depending on how you want to frame it. It’s very hard to imagine anybody being able to employ me and be my boss.

JEFF:    In the book I talk about growing up I never felt entrepreneurial. I didn’t see myself as an entrepreneur. I was never the ideas guy. I was the execution guy. If you had a good idea, I help you get it done and that was the career path I followed and only getting pushed out of the mainstream world and kind of kicking and screaming dragged into an entrepreneurial venture did I kind of see this different side, the dark side, the light side, depending on which way you want to go.

MICHAEL:        There’s some baggage being an entrepreneur comes with which is around it’s about the money. It’s about the hustle. It’s about the grind. I would not have guessed I’d end up being an entrepreneur. I’m just as surprised as anybody else. I’m surprised I’m still an entrepreneur. I could have guessed I might have become a failed entrepreneur. I do think there’s times when we’re in a taste for autonomy is part of what drives you into that kind of entrepreneurial way of working.

JEFF:    For some folks, I think there’s a taste for autonomy and maybe there’s a little frustration as well. My background is design. Even in digital design, even today that career path is fairly limited. There’s not that many options once you hit director of design beyond that; SVP, EVP, C-level roles – there just aren’t that many of those. You kind of have to figure out what to do next and how to do it.

MICHAEL:        Of course, there’s always the danger of continuing to try and climb the mountain, getting to the top of the mountain and going, “It’s not the mountain I wanted to climb.” You’re like, “Wow, I wanted all my life to be the EVP of this and actually this isn’t…” It’s kind of that sunk cost fallacy which is, “Well, I’ve invested this much time in it so far. I might as well push for the next level because that’s where the reward is.” Of course, it’s never there. In some ways, I had a very good fortune – I became a road scholar in my mid-20s and it did three things. One is you immediately get a status and a degree of success by being a road scholar. More practically, it did two things. Most importantly, I got to Oxford where my immediately met my wife and we’ve been married for almost 30 years now. That’s a huge win. The other thing it really did was it stopped me becoming a lawyer because I was finishing a law degree in Australia and if I hadn’t got the scholarship that took me out of Australia, I would have gone – well, what they call College of Law which is kind of the work you do to become qualified to be a practical lawyer. It’s the gap year between finishing a law degree and starting a law career. Then of course, if you did College of Law, you’re like, “Well, I might as well do a couple of years being a lawyer.” Then you’re like, “Well, another five years and I could be a junior partner and that’s awesome.” Then before you know it, you join the many lawyers who have gone or had a 15 year career being a lawyer. I never actually wanted to be that. It’s just momentum swept me onwards. Sometimes you need a lucky break and it pulls you out of the stream that you’re in.

JEFF:    I’m going to double down on what you said about the sunk cost fallacy because it permeates everything. It’s easily applied in the work that we do when it comes to the projects. We’ve come this far – we’ve done six months in this direction and yes, all signs post this is going to be a disaster but we put in six months’; so we’ve got to get it done. The same kind of concept applies to your career, your aspirations, and life as well. I’ve put in this much time working towards becoming a lawyer. I should be a lawyer, shouldn’t I?

MICHAEL:        Exactly. You’ve got to keep making sure the hole you’re digging is the right hole. Digging faster just doesn’t fix the problem.

JEFF:    That’s really smart. Tell me a little bit about your story.

MICHAEL:        I finished doing a Master’s degree in literature at Oxford. I’ve now been in university for eight years. I’ve got three degrees. I have no idea what I’m doing with my life. I stumble into this job having nothing to do with any of the degrees I have in a world of innovation and creativity. I spend 5-6 years in a startup who are doing new product development. The guys who started it were mavericks. They came from Unilever, a big consumer goods company. They’re like, “Let’s just do things differently. Let’s invoice weirdly. Whatever normal is, let’s not do that.” That was very liberating as a first job for me. At the time, I had long hair and earrings and I made my own clothes. They’re like, “Cool. You’re weird. We like it. You’re smart and weird. It’s a nice mix. Come on down.” At a certain point, I went, “I don’t love spending my life inventing the next range of soup for Heinz. It’s not the impact I want to have on this world.” I also was curious to know why all the ideas we had tend to go back to the bigger company we were working for and they’d just die. Innovation struggles within corporate settings because corporations are bastions of homeostasis. Keep things as they are. Doesn’t matter what anybody says. Stability is the point of a big organization. I moved into the world of organizational development and organizational change. How do you make change happen in organizations? That took me from working in London to being part of a startup office in Boston which just was miserable for 2-3 years. We struggled. It was a poor, badly thought through decision with no real strategy. It was just terrible. That was miserable but it got me to North America. My wife and I, when I knew I was leaving that job, decided to move to Canada. I linked up another consulting job but my flight out of Boston was on 9-11. All sorts of mess and chaos and confusion around that but it also meant when I finally got to Canada, the job I had lined up  had vanished which was a lucky break because after six months in a transitioning job, I started the company that would become known as Box of Crayons. When I started it, I was just doing the desperate entrepreneur thing which is my business model is to find somebody with a wallet and a pulse and say yes to whatever they’re asking for. Over time, that company found its focus and it was to help teach practical coaching skills. The language they have now is helping organizations move from advice driven to curiosity lead. For a long time, our hook was we teach 10 minute coaching to busy managers. I kind of ran that for 15-17 years. About 1 ½ year ago, stepped away from being CEO of that and set up a new company called which you kindly referenced at the start. If Box of Crayons has where they say a B2B focus, has a B2C focus. It’s helping individuals become a force for change. Helping them not only evolve and grow themselves but make the world a better place at the same time.

JEFF:    And along the way, you’ve written some books and developed this entrepreneurial platform for yourself and you’re sharing your information. Inadvertently, you find yourself with this lucky break of starting your company shortly after 9-11. Then you start to spread beyond that. You start to write books and share your learnings and advice. Why?

MICHAEL:        It’s mostly a miserable experience writing a book. You have to know why you’re doing it. You’ve got to have a purpose to it. Sometimes that purpose is I see how it fits with my business model. The Coaching Habit book which is the one that’s really kind of taken off. It’s closing in on about a million copies sold now which is ridiculous. I didn’t need it to sell. That’s just a bonus. That’s just a miracle. I knew that with The Coaching Habit, if I could sell a thousand copies to the thousand right people, it would generate money for my company and it has. I can point to at least $10 million in revenue that that book has specifically generated for Box of Crayons. Somebody has picked up the book and gone, “I read your book. You do training around this.” We’re like, “Yes, we do.” There’s at least five clients which are worth more than a million dollars in revenue for us directly correlated to that book. The very first book I wrote called Get Unstuck and Get Going, it was not so much about fitting into a business model though I was like, this kind of reflects what I’m teaching at the moment and who I’m talking to. I got left a bit of money from my grandfather, $20,000, when he died. I thought, “What do I do with this?” I had this idea of a book that I’d been in and out of for about five years. My wife was kind enough to say, “Look, spend the money on the book.” I self-published this book. It was complicated. It was like a kid’s flipbook. You have a soccer player’s head and a ballerina’s body and a scuba diver’s legs and you can mix and match that. It brought a process for generating ideas and provocations using that as a basic technology. It was in 2005 that I did this. It was kind of just before self-publishing became a real thing and it involved us having to set up getting it made in China. It was a complicated thing. This was more of a I want to follow through on a project. I want to have a book written. I want to get this out in the world and I think it’s a good idea.

The first two books I wrote, Get Unstuck and Get Going, Do More Great Work, I could see them as being articulations and encapsulations of intellectual property and ideas that I had. Here was a sentimental moment for me. This is really essential to understand in the success I’ve had in growing a platform. There’s a guy here in Toronto who runs something called Strategic Coach. I went and saw a talk he gave. He said, “Look. There are three phases you go through as an entrepreneur.” He was talking about somebody who was a dentist. He says, “Phase one, you say, “I’m a dentist.” In other words, you collapse your identity into the job role. Phase two, you say, “I’m an entrepreneur who does dentistry. Now you understand that it’s not about how good of dentist I am. It’s about how good of an entrepreneur I am, how do I market, how do I sell, how do I set up systems, how do I be efficient, how do I be ambitious, how do I sell beyond myself? The third role is I create intellectual property around dentistry.” What this guy was saying is that this is how you scale. This is how you create impact. You start thinking about IP. The very first part of IP I created was called The Eight Irresistible Principles of Fun. I was giving a talk at my local coach chapter and I was like, “I’m going to try out this IP thing.” I created an idea, a model, and built out some language around it and turned it into a little video which slightly pre-YouTube but it had over a million views before I knew what I was doing. Now I would have captured names and moved people to an email list. I did none of that.  That understanding that creating intellectual property allows you to scale was a very powerful moment for me. Then you get to a point where you’re like now you’ve got to create good intellectual property. Of course, everybody knows that you want to create content to get known. Everything is full of – the noise is enormous and signal is hard to find. Now it gets into some of the stuff that you talk about which is what are you creating and how are you going to get out there into the world and how does it stand out from the crowd? How do you get  noticed? That’s hard.

JEFF:    It does feel like everything has been said and everything has been out there.

MICHAEL:        That doesn’t matter though. Old wine and new bottles.  My best selling book The Coaching Habit is like questions are good. I’m not the first person to figure that out. Start with Socrates and then go back another 5,000. The way I talk about it and the way I present it is interesting and different and curated in a certain way. You can’t use the excuse that it’s been said before because it’s like, yeah, of course it has. Everything has been done and said before and it can be resaid.

JEFF:    People lose that. I remember a few years ago I was at a design conference in Amsterdam. There was a thousand designers there. I was speaking to some of the organizers, just kind of, “How’s it going? How do you feel about the event?” They said it’s so difficult creating this kind of event because you’ve got the 15, 20, 30 year veterans of design who really want content for them and then you’ve got all these folks who are just coming into the practice and they’re looking for that entry level 101 level content. It’s one of the things that I think people forget is that there is always a market for entry level content. There’s always a market for 101 level content. What is the new bottle? The new bottle that you’ve had success if it’s old wine in a new bottle. What are the characteristics of that new  bottle that helped you stand out?

MICHAEL:        It starts with a commitment to try and find my own articulation of the thing. Years ago I came up with the acronym TABO. TABO stands for true and bleedingly obvious. It just feels like that what I see flowing through my feeds on an endless day. It’s like, “Here’s a bleedingly obvious statement about leadership.” How does that add to the good of the world? It’s like here’s a story about Southwest Airlines. I’m like, “Do we really  need to talk about Southwest Airlines again?” They’re great but where’s the new story? What’s the new angle? What’s a different way of framing that?

There’s this other great quote about finding simplicity on the other side of complexity. It’s a designer based quote. It’s a U.S. Supreme Court judge said, “I don’t care for simplicity on this side of complexity but I’d give anything for simplicity on the other side of complexity.” Part of the work I try and do, and it doesn’t always work but this is my goal, is to have kneaded the dough to get it so it’s like I’ve worked through all of that and what I present feels straightforward but also has a freshness and a difference that feels remarkable.

JEFF:    It takes experiments. It takes iterations to figure out what that new and remarkable packaging should be.

MICHAEL:        And failures. You’ve got to realize how much failure the successful people have.

JEFF:    It’s something that not enough people write about and not enough people share when it comes to sharing experiences. Folks like to talk about, “I did this and it kicked ass.” The 900 things I did leading up to that did not kick ass.

MICHAEL:        I saw a picture the other day of a guy who has published hundreds of cartoons in The New Yorker which is the acme of a cartoonist. That’s where you want your cartoon to get. He’s got these two piles and one is tiny which is the yes’. Then he’s got a pile this high and it has a sticky note saying  no’s. He’s had thousands of cartoons rejected. Seth Godin’s got a new book out called The Practice which is excellent. It’s about shipping creative work. It’s a great primer for anybody who is going, “How do I do this stuff?” One of the phases I heard Seth talk about the other day was he said, “I blog because it’s tomorrow, not because I have something to say.” He’s just committed to blogging every day. He’s like, “I’m a good writer. I create books and content because I blog every day.” It’s a commitment to process even over outcomes.

JEFF:    I’ve recently quadrupled my writing pace. I’m not every day; I’m every week. It used to be every month. Now it’s every week. There’s better blog posts than some at that pace.

MICHAEL:        I’m writing a new book at the moment. Every day, I write. Some days I write garbage. I’m in my first draft. Some days I write total garbage and some days I write partial garbage. It’s all garbage at the moment. It’s miserable but it’s part of the process.

JEFF:    I introduced you as best known as the author of The Coaching Habit. You’ve written several books. You’ve written a book more recently called The Advice Trap. However, based on the way you wanted to introduce yourself and what I know, The Coaching Habit is the most successful book. While I haven’t sold a million copies of it, Lean UX, the first book I co-wrote with Josh Seiden also was kind of a defining book for me. Regardless of how many books I’ve written since then, I’m the Lean UX guy. For folks who have had a bit of success, who have built a bit of a platform for themselves, who have scaled with IP and they’ve gotten known for a thing, and now either want to expand that or maybe move to an adjacent subject matter or maybe just take a sharp right turn and talk about something completely different, how are you getting beyond that? Do you want to get beyond being The Coaching Habit guy?

MICHAEL:        The first is the question to go, are you trying to double down on the success you’ve had? There’s a lot of good reasons to do that. It’s like this is what you’re known for. Just keep pushing money onto that process and investing in building that reputation. At a certain point, you might say, “Look, I’m tired of this.” I’m looking at Marie Forleo’s book there and she’s like, “I do my Marie Forleo MBA and I do it every year,” and she makes millions of dollars on it and she just keeps doing it. I think she’ll be fine to milk that cow for a long time. For various reasons, one of which being me moving out of Box of Crayons and a new CEO coming on board and her wanting to de-risk the company so it wasn’t all hanging on Is Michael alive or dead? Is Michael creating IP or not IP? She’s like, Box of Crayons is going to own the IP around coaching and curiosity because that’s the business model. I own that company and so, I want Box of Crayons to succeed. There was a strategic decision to have me opt out of that. For me, they’re involved first of all, a process of, let’s call it mourning; to let go of the identity around The Coaching Habit because I’d actually spent 15 years trying to build a reputation in this space and getting known for it. To not be going, “This is what I’m chasing and what I want to be known for” is a bit of an odd process.

Then what I found is even if you choose to kind of leave the hamlet which you’ve been living, you actually need to leave the valley in which you’re living; not just leave the hamlet. It’s hard to get away from the gravity of a reputation. It’s like Godfather II, “Just think you get out and they keep pulling you back in.” There was a defining process that really helped me. I worked with a  woman called Erin Weed. She’s based in Colorado. She has a process called “The dig.” What she does is she listens to your stories over two half day sessions and then she comes up with an operating system based on your language which she says, “This is what you stand for.” She says, “I’m going to give you your word. This is the word that is essential to your identity and impact you want to have on this world.” I was a bit skeptical about it but when I did it with her, the word she came back for me around was the word power. She’s very interesting and not what I was expecting at all. It’s too long to explain why that’s such a good relevant word for me but it kind of got me out of the valley, over the hill, and to the next valley. As soon as I had that word and permission to have power rather than coaching as my thing, it opened up all sorts of ideas around what I could write about and start a podcast on and what I could build as an entrepreneur.

JEFF:    Do you feel like she gave you the okay to make that shift?

MICHAEL:        I wouldn’t quite use that language. What she showed me was a doorway. It’s like up to me to walk through it and cross the threshold and do that. She’s like, “Here’s the path out of the valley. Let’s go with power. Walk this path a little bit, get over, see the sunrise in a new valley, see what changes and shifts for you.” I think that’s part of it. I think the other answer to this question is leaning into Jim Collins’ metaphor. He talks about strategy and he says, “The way you build a good strategy is you fire bullets and then you fire cannonballs.” Bullets being low-cost risks, small experiments, and cannonballs being the commitment to the bigger thing. In the last year, as I’ve been in between states, I ran a literary conference called “The Two Pages Festival” where in a day I had 20 authors do half hour interviews with me where they’re read two pages from their book and then we’d discuss it. It almost killed me because it was like a 15 hour event on LinkedIn Live. I ran it for four months – I did something called Cocktails and Questions where I’d invite a small group of people from my extended network and I’d host a one-hour conversation where we’d sit with a hard, vulnerable question and people would share and connect and build a network. Partly I did those because they’re interesting, creative projects I wanted to do but partly I was firing bullets to go, “Is there a business in me hosting intimate conversations?” I loved it but it’s too draining. It’s not sustainable. It’s not scalable. I can’t do that. Is it something around doing a two pages podcast? Maybe. How does it fit with the impact I’m looking to have in the world? How does it fit with this idea of power and unlocking power and challenging and upturning people’s assumptions around power? That doesn’t quite fit there either. Part of it is you can’t think your way through this. You have to run small experiments to see what feels interesting.

JEFF:    That’s the philosophy I bring from the product world. Forever Employable talks about running experiments. How do you know which direction to head into? You don’t. You’ve got some ideas.

MICHAEL:        It’s like IDEO. IDEO is like fail fast to succeed faster. It’s that core design process which is like do rapid iterations and you’ll get somewhere interesting faster.

JEFF:    One of the things I talk about in the book is giving everything away. Give it all away for free. The more you can give back, the more that comes back to you. It was unintuitive for me to learn. It was difficult for me to come to grips with. I think for a lot of folks, the idea of sharing their experience and sharing their challenges and how they overcame those challenges is vulnerable to some extent but more so, they see it as it’s my competitive advantage. I know how to do this now. If you don’t I can beat you to it. The example that comes to mind immediately is I read an article that you wrote where you were very specific and tactical about all the things that you did to promote The Coaching Habit and explicitly, the part that I recall most clearly is the part about how to get reviews for the book itself. Not only were you very specific, “Here’s the 10 things that we did and here are the templates. Go get the templates. Download those things…” I went and I did all of that. I followed the recipe. I grabbed your templates. We edited them to fit this content. We shipped them out and it worked and we’re getting review for Forever Employable and it’s amazing. Super grateful for you for that. How do you reconcile giving all of that away when, in many ways, that was your competitive advantage? That’s what made The Coaching Habit rise above the noise in theory.

MICHAEL:        I don’t buy into the theory of giving everything away. I buy into the Adam Grant framework of give and take which is there’s two ways of giving in this world. One is giving in a way that is fully generous but it also nourishes you. There’s another way of giving away which is that which depletes you. In Grant’s book Give and Take, he says the people who give in that poor way, in that depleting way, they come last at everything because all they do is be a victim to their circumstances and they get exploited. The people who tend to come to the top of the list are the people who give with a mindfulness around why they give. Not with a direct expectation, not with a “I’ll scratch your back and I expect something back immediately.” That article is a really good example. I wrote it 3 or 4 years ago now. I know thousands of people have read it and found it useful because people tell me. Sometime in the next week or two, I think this will happen which is a guy is writing a long blog post on the state of publishing at the moment which will get published on Tim Ferriss’ blog. My book The Coaching Habit will be one of the case examples in that. He knows about my book because I wrote that long article. I wrote that article as a gift to the world to go, “Look, book marketing is hard. Nobody tells you what to do. It’s a grind. Not all books deserve to flourish but if you’ve got a book that is great and you really want to get out in the world, I’d like to know what the really great books are and it helps if you know how to market it a little bit.” There’s nothing at risk for me to share that. What’s really helpful is to understand what your business model is. How do you make money? How do you protect how you make money? With, the way we will make money is by helping people make progress on work that matters to them. It’s like here’s how you get going, make momentum, make a difference in the way you show up in the world. I’m going to ask you to pay for the progress that I help you make. That’s going to be my business model. What that means is my teaching is free. My teaching invites you to become part of my community. When you’re part of my community, you’re invited to become part of a membership site which allows you to make progress on what works. I understand what I’m giving away and I understand what I’m not giving away. That creates a degree of freedom.

JEFF:    I love that there’s a very explicit and deliberate thinking, plan behind, “I’m going to give this away which is going to drive back some kind of activity that ends up generating income for me.”

MICHAEL:        To your point, almost everything you give away, A) somebody else has thought of it already B) they’re probably giving it away from free C) they probably really can’t implement. If they find it and they love it, they may call you up and go, “Hey, how do I do this?”

JEFF:    Thank you. This has been delightful. It’s been information. It’s been fun and tremendously valuable. I appreciate you generously giving away your time.