Companies Don't Disrupt,
People Do

Featuring best-selling author, Whitney Johnson.

Today, we're going to be talking about how people disrupt. And I'm going to be interviewing you, which I am so excited about. I read your book recently, and as you know, became just so obsessed with it and with you. I'm just going to give people a little introduction to who you are. Whitney is one of the 50 leading business thinkers in the world according to Thinkers50. She is the author of the critically acclaimed "Disrupt Yourself", which is fantastic, and talks about the framework she developed after she co-founded the investment firm with Clayton Christensen. She's also a frequent contributor to the Harvard's Business Review as well as the host of the Disrupt Yourself podcast, which I was listening to this morning on my run, which was great.

So Whitney, why don't you tell a little bit to our viewers about these three books that we're going to be giving away at the end of our little interview?

Yeah. We just thought it would be really fun to ... Once we talked about this, Courtney and I agreed that a lot of people would want to read some of them, so we decided that if you stick around to the end and you raise your hand, we will have a mini raffle, and I will sign a book for each of you, and send it in the mail. We hope that you'll stick around and really enjoy this conversation that we're about to have.

Yes. And with that, please either tweet at us or mention in the comments. We have people paying attention to those, so we'd love to hear any questions that you have for Whitney as well as what you're thinking about. So let's just dive right in, Whitney. Can you tell us sort of where you are right now and what you're sort of up to?

Yeah. I'm actually in New York City today. The weather is beautiful here as well. I came to the city for a couple of reasons, but what I'm doing today is I've been doing podcast interviews for my Disrupt Yourself podcast. This morning, I had a conversation with Kara Goldin. She is the founder and CEO of Hint Water, which is amazing if you're trying to get off Diet Coke like I was about a year ago. Really fun. Then, I had another conversation with a fellow by the name of Patrick McGuinness, who is the 10% entrepreneur, but even more importantly, while he was at Harvard Business Review ... not Harvard Business Review. At Harvard Business School, he came up with the term "FOMO". You're going to hear all about FOMO on the podcast episode with him. It's been a lot of fun. Now, I get to have this conversation with you.

Fantastic. Well, I definitely have FOMO sometimes, so I'll be very interested to hear that podcast. Just to get into this idea of disruptive innovation, you discuss it a lot in your book, as well as becoming a major theme in your life, and the focus, really, of your entire second book. Can you tell us a little bit about the path you took to find disruptive innovation? And maybe give us a brief definition of really what disruptive innovation is.

Yeah. Great point. Great question. All right. So disruptive innovation. It's a term coined by Clay Christensen at the Harvard Business School. It's basically a silly, little thing that takes over the world. So for example, we had Toyota disrupt General Motors. We've had Netflix disrupt Blockbuster. We've had Uber now disrupting cabs. So that's what disruptive innovation is.

Personal disruption, which is what we're really going to be talking about today, is this notion of disrupting yourself. So you start at the bottom of the ladder, you climb to the top, and then you jump to the bottom of a new ladder. A great example of this actually is Lady Gaga.

If you think about Lady Gaga, here's a woman who worked really hard in New York. She goes to her first album 2008. She screams to the top of the charts. She's just over the top, bigger than life, or larger than life. Then, she gets the number one on the charts and she completely disrupts herself. She does things like records jazz with Tony Bennett. She does a Sound of Music tribute. She then does ... What else did she do? She ... oh, recorded a country album. So she disrupted herself, and it actually paid off, because the Super Bowl last year, the audience listening to her, it was the largest music audience ever.

So personal disruption, again, is starting at the bottom of the ladder, climbing to the top, and then jumping to the bottom of a new ladder. So how does that play out in my life? Well, I was disrupting before I knew I was. When I first graduated from college, I actually graduated in music from college. Came here to New York with my husband. He was in school. I didn't realize this then, but I wanted to work on Wall Street, right? And so for me, I was a music major, I hadn't graduated from an Ivy League school, and I was a female. So there was no way, absolutely no way I was going to be able to walk in the front door and say, "Hey, Merrill Lynch. Hey, Smith-Barney. Hire me."

So I started as a silly little secretary, but once I got a foothold on Wall Street, and I saw what was happening, and I started taking business courses at night, I was eventually able to move up to the top of a ladder, which was I was an equity research analyst, and very good at it. But then, I jumped to the bottom of the ladder. I disrupted myself again. In 2005, when I said [inaudible 00:05:55] Christensen's book. I had just read "Innovator's Dilemma". It was helping me understand what was happening in Latin America, how wireless was disrupting wire line. But I was also having this personal epiphany that if I, in fact, wanted [inaudible 00:06:09] in my own career, where I was at the time, I had gone to my boss and said, "Hey, I want to be in management someday." He was kind of like, "Yeah, that ain't going to happen." There were things that I wanted to have happen that weren't going to happen if I stayed there.

So I had to disrupt myself. I left Wall Street, which I don't always think is necessary, but I left Wall Street and became an entrepreneur, and then connected with Clay Christensen, and then moved up the new curve. So that's how it's played out in my life, but for everybody listening, think to yourself, "Silly little thing starts the bottom of the ladder, climbs to the top, and then jumps to the bottom of a new ladder like Lady Gaga."

Just like Lady Gaga. I love that. Not that I think I really want to be Lady Gaga, but it's a good example there. I think when I first started reading your book "Disrupt Yourself", I connected with it a lot, because I had recently gone through my own disruption. I had been living in Colorado. I had this nice life all planned out. I was going to work for an environmental non-profit. It seemed like I was at the top of this ladder and feeling really good. I decided that really wasn't going to be me. I jumped to the very bottom of a ladder here at HubSpot, and I entered as an entry-level Hubspotter. It wasn't exactly what I thought I was going to be doing, but that really connected with me when I started reading your book a few months ago.

That's a great example, Courtney. That's a great example. So how long ago did you start at HubSpot?

I've been at HubSpot now for almost two years, which is crazy. And ...

Okay. Now, you're climbing to the top of a new ladder, right?

Yep, so Brian Halligan, watch out.

Yeah, exactly, Brian, if you're listening. What's interesting, just to kind of play this out a little bit more, because I think often times, when I talk about the idea of disrupting yourself, people think I mean you have to change jobs. Now, in your instance, you did. You left the environmental firm, but in fact, what it's telling you is you just need to stay in a job three to four years, and at that point, it will be time to try something new. So another year or two, it'll be time for you to disrupt yourself inside of HubSpot, if they are smart, and what you do [inaudible 00:08:22] take on a new role.

Yeah. And I mean, I had joined the Academy team back in January and had gone through a mini-disruption, leaving my training role and then becoming an inbound professor. So I've already had a mini-disruption in the two years that I've been here.

There you go. There you go.

Yeah, and sort of building off this idea, in your new book, you do talk a lot about the S-curve, and jumping to a new S-curve. Can you explain to us a little bit about that S-curve? I know that we do have some slides here that display what it's going to look like.

Yes, please. Okay, so why don't you put up the very first slide, too, so that people can visualize it as we are talking about it?


So one of the things that I discovered is that the S-curve that was popularized by Ian Rogers in 1962, which is really focused on helping people figure out how quickly an innovation will be adopted. We use that S-curve when we were in investing. The way we looked at it is we said, "All right. When you first launch a new product, you're going to be at the bottom of the S. There's going to be a lot of work happening, but not a lot of results." Then, typically once you reach 10-15% market penetration, you're going to reach a tipping point. At that point, you're going to move into hyper-growth, where you don't have to work as hard and a lot is happening. Then, at 90%, or market penetration, you reach saturation. Which again, you might work really hard and not much is happening.

If you were to plot this against Facebook, which I do talk about in the book, you'll see that Facebook has mapped almost perfectly to the curve. Now, the big "Aha!" that I had as we were doing this investing is that you could also apply this S-curve to psychology of disruption. So for example, if you've started a new job, if you've started a new project, if you've started a new role, the S-curve tells you that initially, progress is going to be very slow by definition. And knowing this helps you ... and you can go to the next slide.

Oh, perfect.

Knowing this can actually avoid discouragement. Then, as you put in the work, you will start to accelerate into competence, and with this comes confidence. Now, if you're tracking against the 10,000 hour rule, that period of feeling completely incompetent, and you're only working 40 hours a week ... Only ... Then, you're going to be in that low end of the curve about six months.

Then, you'll figure out what you're doing and you'll move into competence, and with that comes confidence. And this is the exciting, exhilarating part of the curve, where all of your neurons are firing, and you want to ideally be in that place as long as possible. Typically, again, working 40 hours a week, you're going to be there for two to three years. Then, as you approach mastery, things will be very easy. Super easy. But because you're no longer enjoying the feel good effects of all that learning, you can actually get bored. So sometimes, when that happens, if you get bored, if you don't jump to a new curve, either because you're afraid to jump or your boss won't let you jump, that plateau can become a precipice.

So bottom of the curve, you can get discouraged. That's natural. Middle of the curve, you feel confident. You're supposed to. Top of the curve, it's easy, but you can get bored. Now, I put a little link up here. If you want to figure out or test where you think you are on the curve against where you are, you can go to my website and just take this quick S-curve locator. It'll take you just a couple of minutes. So that's where this came from.

That's great. I think-

Go ahead, Courtney.

Oh, yeah, no. I think this can really help. Finding out where you are on the S-curve for people, I think, when they are starting to see that uphill battle out of confidence, can really help them get that sense. I know it's something I struggle with personally. Where it's like, where am I? Am I close to mastering? Am I not? I feel confident, but I'm not yet bored. Being able to judge where you are on that S-curve I think can really help all of us. So thank you for putting up that link there at the top.

Yeah. So if you want to go to the next slide, let's just play this out. So, you've got this S-curve, and it helps you ... basically gives you a framework for managing change. And managing change not only in the sense of your own personal trajectory, so for example, Courtney, when you left Colorado to come to HubSpot, but also when you're managing people. And so, if you want to optimize it, and you've got a team of people who are working for you, you ideally want 70% of your people in the sweet spot of that curve at any given time. 15% of people at the beginning of the curve, so they're learning, they're asking lots of questions, they're wondering why you do it the way you do it, which opens the door to innovation, and then you want to have 15% of your people roughly at the top of the curve.

And so when you look at these S-curve locators from an organizational standpoint, you can say to yourself, okay, good. We're about where we need to be. But then you wanna focus on those people who are mastery level, and say, what are we gonna do with them next? Because they're a flight risk. You don't find a way for them to disrupt themselves inside your organization, they may go elsewhere.

Now, one other thought, and then I'll let you ask, you know. But what I wanted to do is say, all right, so here's our S-curve, but how do you move along the S-curve? And so I came up with seven accelerants, which are also for ways for people to think about how do I actually like to disrupt? So you take on the right kinds of risks, you learn to play not only to your strengths, but to your distinctive strengths. You embrace constraints. You actually discover ... and I think, actually, HubSpot, by the way, really fits this beautifully. You discover that in order to climb the curve, you not only need to embrace, but also if things are getting too easy, you gotta impose constraints. You battle entitlement, which is the belief that I exist there for I deserve.

Once you get to the middle of that curve, everything's so easy. You start thinking, oh, I don't wanna listen to other people's ideas, because things are going well. My margins are expanding. But it's precisely at that time when you want to be listening to their ideas. Then sometimes you gotta step back in order to grow. Courtney, your example of coming to HubSpot is a great example of that. Your step back had become a slingshot for you. Give failure its due. We'll talk about that, I hope, in a minute, and then the importance of being willing to be discovery driven.

And so these seven accelerants move you along the curve quickly, and every single one of us has one or two of these that we do actually really well, and then we all have one or two that we don't do as well. And the question is is just making sure you play to your strengths in terms of your different accelerants.

Yeah, and I think that's a great segway into sort of my next question here about giving failure its due. Recently, at HubSpot, we did put on a failure forum, and we discussed how important failure is. We discussed the different types, and you talk about this as an important aspect of failure, and I think this is the thing on the S-curve I struggle with most, really giving failure its due. What do you think are the most important aspects of failure? And do you have an actual definition for failure?

Yeah. So ... love it. Okay, so the first thing I would say is failure actually ... I mean, we all fail all the time, and we're all sort of, oh, I think I'll try this, and it didn't work, and so we iterate. So that's not really the kind of failure that I'm talking about. I'm talking about the kind where you try something, and you sort of ... your ego was attached to it working, and then it didn't work, and then how you feel around that.

Now, I wanna just editorialize for a minute on this, and why failure tends to be so hard for us. Most of the people that are listening to this podcast are probably pretty smart kids in school. And what happens when you're a smart kid in school, and this is based on the research of Heidi Grant Halvorson, is that people reward you for being smart. And so you're like, you get an A on a test, we're like, "Gee John, you're so smart!" Or, "Gee Jane, you're so smart!" And so you start to say to yourself, "Well, if I get an A on a test I'm smart. If I don't get an A on a test, am I dumb?" And so our world becomes very binary. And so when we get into the workplace, and we're trying to do something, and not everything can work, our brains immediately go to, "I'm dumb." And so it starts to go right to the core of our identity.

So what I'm talking about in failure is not the stuff that we sort of iterate on, and we all have areas of our life and our professional world where we're comfortable doing that. I'm talking about the failures that kind of get us at the core. And what I want to say here is that it's important, absolutely essential, that when something doesn't work that we want it to work, like we get fired, for example, which I have been, is to say to ourselves, number one, "What did I learn from this?" And number two, recognize that the failure is not a referendum on you, on your identity and your sense of self, and to ditch the shame, because shame actually limits disruption. It's not failure.

And so those are really, I think, the two biggest takeaways for me, is to recognize that it's hard because our identity tends to be attached to our being successful, but once we become aware of that, then we're willing to start saying, "Okay, how do I separate my core identity from the fact that it just didn't work?"

Now, one other thought there. In a workplace, sometimes we say to ourselves, "Well I'm willing to fail, but my boss won't let me." Right? That's the bigger piece. I would say to you, "You can't control whether your boss will let you fail, but there are a couple things you can do." You can manage their expectations. They can say to you, "Jake, I want you to take on this new project." And you can say to them, "Okay, I will. I want you to understand, there are some things that could happen here. Some may work, some may not. Let's experiment with this. Maybe let's not put very much money behind this. But I need to know that as we're experimenting with this, you'll have my back, and in order for you to have my back, here's how I need you to talk about it to management." So you're talking about it sort of improbabilities, so that when it doesn't work the way you thought, it was an experiment, and you got a lot of good information.

And so ... and the last thing I would say is that if you have people on your team that you are not willing to let fail, then you need to take hard look at that, because your star performers, you do let fail. And if you won't let them fail, then maybe they're not in the right job.

Hmm. No, I think that's a great point. For even us to hear as, you know, if we're the people working for someone, but for any boss or manager that's managing people, that's such a good quality. Make sure you have the right expectations set. I think, on the academy team, we do that very well, and some of our principals that we have, always be learning and never settle, they sort of combine those two things really well. Where we're pushing ourselves, we're trying these experiments, we're never settling, but if we fail, we're gonna learn from it. And we're always gonna be learning in that process.

And that makes it really fun, doesn't it?

It does! I love it. I just ran an experiment on the academy team that, luckily, worked out, but it could have not, and I definitely would have learned from it as well. But-

And it would have been okay. You wouldn't have [inaudible 00:20:59] it wasn't attached. Yep. Yep.

Exactly, because I felt that space where I could fail, if that was gonna be the way it was gonna go. And I think with this, there's another aspect on that S-curve, the last one, the number seven, the driven by discover. One of your chapters in your book is titled this, and you discuss the conventional planning versus discover driven planning. And sort of what are the differences here? Because I think a lot of us think in that conventional planning areas, not so much the discover driven.


And how do you sort of suggest us focusing more of the discovery driven?

Yeah. Discover driven. Okay. So I would start by explaining the rationale for this. So if you think about disruption, you are ... you're playing where no one else is playing, either because they haven't thought of it, or they don't want to. So by definition, you, excuse me, are in search of a yet to be defined market. Which means you're like an explorer. So you can't know where you're going, because you don't know where you're going. I mean, it sounds circular, but it works.

Okay, so this idea of conventional versus discover driven. A lot of my work here is based and derived from Rita McGrath at Columbia, so I want to give shout-outs to her. Conventional planning. Let's go back to when you were in school. So conventional planning is you say to yourself, "I am gonna take these courses, and I'm gonna study this much, and when I do all of these things, I'm going to get A's in all my classes. And if I don't get A's in all my classes, then the plan didn't work." That's conventional planning, and most of us are actually pretty good at conventional planning. Pretty good. You know, I do my work, I go to my classes, I'll graduate from high school, I'll graduate from college.

Now, discovery driven planning looks like this. You say to yourself, "You know what? I want to be a doctor when I grow up." So discover driven planning ... now, if it were conventional planning, you'd say, "I want to be a doctor when I grow up." You create a checklist. "In fact, I want to be pediatric surgeon." You create a checklist, and you do step, step, step, step, step, and at the end, if you don't become a pediatric surgeon, you failed. That's conventional planning.

Discover driven planning says, "I want to be a pediatric surgeon. What kind of grades do I have to get in college in order to do that? What classes do I have to get A's in in particular? Like zoology, biology, chemistry." You go, you take those classes, you get good enough grades. You say, "Okay, I want to go to medical school." You take the MCAT, you do well, you get into medical school. Now, once you get to medical school, you've got two years where you take courses, and you say, "Can I do this? Do I want to do this? Am I willing to take the time it takes to get the grades I need?" You say yes. You go another two years.

Now you get to discover again, because medical students do things called rotations. They look at dermatology, they look at orthopedics, they look at psychology, et cetera. They get to rotate into different disciplines. What they find out during that period is they may have thought they wanted to be a pediatric surgeon, but in fact, they don't like children. Well, they don't like working with children. So they discover that they still want to be a doctor, but they want to try something else, they may discover, "Wow, I just invented a medical device." So they become an inventor. Or they discover, "Wow, I love healing people, but I can't stand the site of blood." So they become a psychiatrist.

So at the end of all that, they have discovered their way. They take a step forward, they gather feedback, they adapt. So they don't become a pediatric surgeon. They become a psychiatrist. And you ... we all are actually much more discover driven than we think we are. But if you can take that approach in your career, especially with all the ups and downs of maybe losing a job or not getting the job that you want, but always recognize, once you take that step, you get feedback, you adapt, you go forward. You will be much more successful, because you're gonna be willing to play where others are not, and the theory of disruption states, "When you take on this kind of risk, you're six times more likely to be successful. The opportunity in 20 times greater."

So discover driven planning is essential to pursuing disruptive course.

Yeah, wow. Yeah, wow. That's amazing, and I think a good lesson for all of us. I got a degree in communications and conflict resolution. A lot of people would think that I was gonna be a therapist, because I had taken all these classes in conflict resolution. And that wasn't where I ended up going, and now I'm here, and I do marketing and sales education, which, yes, communication is part of that, but it wasn't the initial sort of goal of what I wanted to do after I graduated. And I think that discover driven is right there with my personal journey.

Absolutely. And if I can pick up on something you just said. So you studied conflict resolution. That's a great time to bring something out. So if you remember, on the slide, we talked about strengths and distinctive strengths.

Mm-hmm (affirmative).

So the conflict resolution for you is a strength, but conflict resolution isn't a distinctive strength if you become an [arbitrayer 00:26:45] or a mediator. But in a workplace, and an academy, and running a team, conflict resolution becomes a distinctive strength because you're able to assemble a team that can work together. And so that's one of the aspects of personal disruption, is figuring out what your strengths are, and then putting yourself in a situation where that strength is not a strength that everybody else has.

Yeah, no. And I think it's definitely been a strength that I've seen come out in a lot of different ways in like interviews, where it's like yeah, I actually have this as an additional to all these other things. I think it help sometimes [crosstalk 00:27:23] when dealing with my friends and family. That's a nice aspect.

Yeah. Absolutely.

Yeah, and speaking of family, over the weekend, while I was on a run, I was listening to the interview you did on your Disrupt Yourself podcast with, I think I'm gonna pronounce her name wrong, but [Krishula 00:27:44] Wagner?

[inaudible 00:27:44]. It's Chrysula Winegar.

Chrysula Winegar.


Awesome. And you guys talked a lot about her program, but also, on top of that, you're very successful, you're contributing to all these different things, you're an author, you're an innovator, you're also a wife and mother of two.

Mm-hmm (affirmative).

You have two teenagers, and I guess I wanna ask you, you know, Mother's Day just passed, how do you sort of handle that work/life balance, and what would be your advice to other working parents out there?

Such a great question. So, I think the first thing I would say is people do rear children on their own. I mean, there are a lot of single parents in the world. If at all possible, rear your children with someone else. In my case, I have a wonderful husband, and so I think that would be the first thing, is be very selective in who you decide to rear your children with.

So it's such a good question. I'm gonna answer it by think in a way that you hadn't quite expected. So we've got two children, our one son is 20, and he's actually in Brazil right now. And I made some notes, because I wanna look at this. Yeah, this is what I wanted to tell you.

So he's in Brazil. He's been there for almost two years, and he's coming back in three months, but he said to me for Mother's Day, "Mom, I wanted to tell you about a memory that I remember, and that I really appreciate." And so he proceeded to tell me about a time he was about seven years old, and we had gone skiing, and when we were riding up in the chair lift, and every time some kind of bump would happen, I kept putting my arm over to protect him. Even though there was a bar. And he got really mad at me. He kept saying to me, "Mom!" He's seven years old. "Mom! You're overprotective! You're overprotective! Stop!" And I remember feeling very embarrassed, almost. Like I was being a bad mom as he was saying this to me. And so he said to me, "But I realize now," So he's 20 years old. He says, "I realize now that you were trying to protect me. This is your way of showing that you loved me."

And so one of the things that I ... advice I would give with our children, because the reality is we're all gonna parent differently, but one thing I discovered is that don't always listen to your children when they're giving you feedback. It might be okay. I mean, you say listen to your customer, listen to your customer. But let it be okay that you're strict. Let it be okay that they don't always like you. Another thing my daughter said to me the other day is, "Mom," So she's 16. She said, "Mom, you know, whenever you give me advice, I know inside of myself that it's probably good advice, but I argue with you and try to make sure that I win the argument so that I don't actually have to act on your advice." Again, don't listen to your customer, right?

And so my advice to the parents out there is that if you feel strongly about, again, number one, partner with someone that you feel really comfortable partnering with, and then number two is be willing to be the parent you think you should be, and when you get feedback from your customers, like Henry Ford said, "If I gave them what I wanted, it would be a bigger, better buggy." If we always gave our children what they wanted, they wouldn't be who they want to be, and they will resent you for it.

So like my son, I'll tell you one other story, when he was seven, I let him quit piano. I shouldn't have.


And he still won't forgive me. So [inaudible 00:31:58]. That is my advice for the day. Don't listen to the customer when it's your child. Do what you think you need to do as a parent.

I think that's great advice. I'm just ... because Mother's Day just passed, I will give out a quick shout-out to my own mother, who I love very dearly. When I was going in to high school, she wanted to send me to a local private school. It ended up being Catholic, I didn't want to go, I complained, I yelled, I'm sure I was the worst child in the world. She didn't listen to me, and she sent me to it anyways, and I credit that decision to getting into the right college, and now ending up here, where I absolutely love. So I think she followed your advice to the teeth with her not listening.

Or you followed her. Whichever. Yeah. Exactly.

Parents, be willing to take a stand.

I love it. So kind of as we're sort of winding down here and leaving plenty of room for questions at the end, I did hear through the grapevine that you may have a third book coming out. Is there anything you can tell us about that? Or what might be in store?

Absolutely. Yeah. First of all, I'm super happy, because I met my deadline. I had to turn in the manuscript to Harvard Business Press on May 1st, and I did. So yay!


I have some really good editors, so I'm happy about that.

So what I decided to do in this book, and I kind of hinted in some of it in a conversation that we had, is the first book really talks about, "How do you disrupt yourself?" What does that look like? What kind of disruptor you are. But one of the things that I've had people say to me is, "Okay, this is fantastic, but how do I let my boss ... how do I get my boss to let me disrupt myself? And how to I get the people who work for me to disrupt themselves?" And so this next book is really taking this framework and putting it inside of a system.

So how do I manage my team as a collection of S-curves? How do I manage people when they're starting out, when they're in the sweet spot of the curve, when they're at the top of the curve? How do I manage it when it's time for them to jump to a new curve?

So that's what it's about, and I'm super excited about it.

I'm excited too. I'm excited to add that to the library that I'm quickly reading. So that'll be exciting. You'll have to let us know when that is bound to hit the bookshelves.

I will do that.

Awesome. So my last question for you, and then I'll turn it over to the questions that are coming in, is what would be one piece of advice for anyone looking to go through their own personal disruption that you would give them?

Hmm. Okay. So two pieces of advice. One is when you're in the sweet spot of the S-curve, and everybody will be at some point, is to at that point in time, push yourself to ask questions and figure out what you can do better. Allow yourself to be stretched. So that would be the first piece of advice. Dot get complacent, be stretched.

Second piece I would say is that because you're playing where no one else is playing, disruption ... well, textbooks aren't gonna tell you this, and actually no one's gonna tell you this, but I am, is that disruption by definition, it's scary, and it's lonely.

So if at any point in your disruptive journey you feel scared, or if you feel lonely, you are probably on the right path to disruption. That is my piece of advice.

I think that's a really good piece of advice. I definitely felt very lonely and a little scared as I moved to Boston, and it's definitely paid off, so I'm glad that I didn't listen to that loneliness and kind of retreat. And so with that, we do have a few questions coming in here. So I'll just read them off to you.


The first one that we have is, "As a manager, how can I inspire my team to think of their current S-curve and jump to the next if they are ready to do so?"

Great question. All right, so first of all, I would help them understand what the S-curve is. So they're kind of aware of what their trajectory looks like, so they've got a framework for thinking about where they are. Because if you go to them and say, "Hey, what are you gonna do next?" They'll think, "Are they trying to get rid of me?" And you don't want to do that.

So if you talk them through what the framework is and say, "All right, so here's where you are. You're in this sweet spot right now. Everything is working. In another year or so, you're gonna get to the high end of this curve, and you're gonna start to get a little bit bored. So what I want you to do," and especially if you're in a high growth company, "I want you to be thinking about who's gonna replace you, and what it is you think you want to do next so that you're preparing to move to that new role."

Now, a word on that. When you want to jump to a new role inside an organization or outside, you're saying to your boss, "I want to jump to a new curve." And when you jump to a new curve, you're also asking your current boss or your next boss to jump to that new curve with you. So you gotta pack a parachute for them and de-risk that jump by preparing as much as possible and connecting dots as much as possible so that they're confident that, in fact, you can take on that new role.

So recapping. Number one, make sure they understand what the S-curve actually is. Why right now they love their job, but at some point they won't. You want them to be thinking about what it is they'd like to do next, but also training their replacement. And then when it's time to jump, make sure, number one, that they're good enough that you, the boss, want to advocate for them, and then secondly, be able to connect the dots and make it make sense for people as to why [inaudible 00:38:21] makes sense, so that you're de-risking it for the hiring manager.

No, and that's great. I think with that, something that I've seen recently that HubSpot as a whole, as well as specifically HubSpot Academy had been doing, is having more conversations around professional growth, and being very transparent about what are the skills that you need to be accomplishing and be mastering or being proficient at before you can even think about jumping? Or what's gonna make that jump really successful? I think in my personal past, I haven't had that opportunity to openly talk about professional growth, and now that I have, it's making those jumps just feel a lot more successful, and a little less like I was falling through the air.

Right. Right. And then it ... because they're institutionalizing the change, right? And so it just ... and what I find surprising is how few managers actually will still be like, "Well how do I do this?" And I'll say to them, "Have you ever sat down and just asked the person what it is they want to do?" And they're like, "Well, no." I'm like, "Just ask them! They'll tell you." Right? They'll tell you.

So anyway, great. It's good to hear.

Awesome. And so we have a second question here from Jason. He says, "How can I best sell my spouse on the idea of personal disruption in my career?"

Okay. Well I would say if you're disrupting yourself inside of your organization, you don't need to persuade your spouse. You just need to persuade your boss. But it sounds like Jason's asking, "How do I persuade my spouse to go try a new job or something new that I haven't done before?" And that's kind of scary for her. I'm assuming it's a her.

So what I would say is that, Jason, the same rule applies here, is that when you want to jump to a new learning curve, you're asking your wife to jump with you. And so how can you de-risk that jump for her? How can you say to her, for example, and this is where the discover driven process can come out, "Honey, what needs to be true for you to get comfortable with me making this jump? What information do you need to have? How much money do you need to have in the bank? What kinds of things need to be true, and what would I need to do before i made that jump that would make you more comfortable?"

So really, battling your own sense of entitlement, like, "I deserve to jump to a new job," and saying, "I'm gonna get the buy-in for my spouse. And heres how I'm gonna do it." And again, taking that approach is saying, "What needs to be true for you to be comfortable with me doing it?"

It sounds so obvious, but we don't do it. So you do that, then your wife will be like, "You are the most awesome husband ever." Jason, that's my marital and couple's therapy advice for the day.

I like that. And I just want to point out to everyone that's listening, Whitney did dedicate Disrupt Yourself to my husband who always says jump, and when I first read that, I thought that was great, and gave me a lot of confidence in the fact that she was able to do this successfully and sort of keep these other aspects of her personal life afloat, which I think we all struggle with a little bit. So I just wanted to point that out real quickly before we move on to our next question here.

So we have another question that says, "What advice do you have for someone nearing the confident section of the S-curve?"

Oh, okay. Well, first of all, congratulations. It's about to get really, really fun. What I would say to you is as you move into this sweet spot of the S-curve is to, first of all, just enjoy it, right? You've been through six months of going home from work every day feeling like, "I don't quite know what I'm doing." And right now, you really do. And so I would say to yourself enjoy it, and then push yourself. So give yourself three months or so, and then look for ways to continually challenge what you're doing.

So for example, one thing you can do is you feel like you're doing the job pretty well and you could just kind of coast, start reaching out to other silos or other departments inside your organization and say, "Here's what we're doing. What could we do better?" And when you get naysayers saying, "What would you do? How would you do it differently?" So really, one of the ways that you battle entitlement and move up that curve is to open up your network and talk to people not like you. So I would say one tangible, concrete thing you can do moving to the sweet spot is to, now you feel like you got some grasp of what you're doing, open up your network and start cultivating opinions and ideas from people across in other silos, either internally or externally.

No, and I think that's fantastic. I mean, that's the whole reason why we're here today. I reached out to you, you were sort of in a different area than I was in, and I wanted to learn from you and open that up to the rest of these people here. So I think that's fantastic.

We have a few more questions here. One from Anna. She says, "What if there's just nowhere to go? If it's flag instead of a curve?"

Flat, maybe?

Yeah. So what if there's nowhere to go at all, if it's flat instead of a curve?

Okay. Great question, Anna. So when you're on a curve, remember I said a few minutes ago about how the odd of success are six times higher, well that's 6% of 36%, so there's still a 64% chance it's actually not the right curve. So we have lots of not right curves in our life. There are some big ones, some little ones. So here are four questions I want you to ask yourself to figure out if you're on the right curve, and then I'll explain what you should do if you're not.

Number one, ask yourself, "Am I playing where no one else is playing?" And that can be inside a job, so for example, you get hired to do a job that like there's someone else in the company already doing it, that's a red flag. Like probably not the right fit.

So number two, are you playing to your strengths, your distinctive strengths? Question number two, if you can answer yes, then stay on the curve.

Number three, is it hard but not debilitating? And what do I mean by that? If you show up to work every day, and you're like, "This is really hard, but oh, it's so fun," then growth is gonna come. But if you find yourself feeling exhausted, and you're actually maybe even getting sick, then that's a symptom that the curve is a flat line. It's just not a good curve.

And then question number four is are you gaining momentum? Now, there are lots of different metrics you can use. We see metrics all the time when you're trying to figure out how many leisures you have. The way you could use that metric for you at work is, for example, if this week, you went home from work one day ... see, you have one hour where you felt like you knew what you were doing, and next week you have four hours where you feel like you know what you're doing, then you're gaining momentum.

So take a market risk, play to your strengths, hard but not debilitating, and number four, are you gaining momentum? Now, if you can answer yes to all four of those questions, then you just need to persist. Sometimes you just have to work harder. If your answers to those questions are no, to three or more, then you need to jump to a new curve. Which means sometimes you have to change jobs. You just have to. And that's okay. But better that you figure out that you need to than you get fired. Although you might get fired, and that won't be the end of world either.

So ... but the good news is is that no S-curve, even if it's not working, is ever wasted. Because as you go through your life, and I don't know how old you are, but what I know is that every kind of little piece of things that worked or didn't work, they come together, and eventually all those little curves, they will come to the right curve for you. And maybe you'll figure it out sooner, maybe you'll figure it out later, but if you keep being willing to disrupt yourself, you will eventually find a pretty ideal curve for yourself.

No, and I think that's great advice for Anna. So hopefully she took some notes there, and is gonna be able to ask herself those questions to find her next curve.

We have a few more here, with just about 10 minutes left. we have one from Hunter. So he says, "If you're on a career path that you see moving differently than you want, should I disrupt yourself earlier on the S-curve than expected? Or wait until you learn what you can, and then disrupt?"

What a great question, Hunter. I think what I would say is if you ... so one thing I didn't say earlier, but there's a time when you know, deep right here in your gut, that you need to do it. If you don't listen to that, you will go awry. So what I would say to you is it always takes longer to find a new curve than you think it will, so if you ... the very fact that you're asking me that question would suggest to me that it's probably time for you to start finding a new curve. And it could take you three months, it could take you six months. But while you do that, then do the very difficult thing of when you're at work, staying engaged in what you're doing and learning whatever you can. It's hard. It's really hard to try to ride two horses, but that is what I would encourage you to do. Start putting in place the pieces now to do that, and at the same time, learn as much as you can while you're still there. Show up to work when you're at work, and then figure out what's next.

It's definitely hard. I did that when I was working for this environmental non-profit, and the environmental world is very different than what I was interviewing for, and sort of having those two sides of myself was difficult, but definitely worth it in the long run. One, because [crosstalk 00:49:07].

Yeah, because it's always easy ... Courtney, just ... it's always easier to get a job when you have a job. Always.

Always. Definitely.

Okay, go ahead.

And so we have one from Valentina. She says, "How do you fight the fear and continue on the path to be disruptive?"

Ah. So two things I would say, first of all, you fight the fear by getting information. So number one is you now know, because I just told you, that if you feel scared and lonely, you're on the right path. So that's helpful. The other way that you fight the fear is you know the data will tell you, is that whenever you go into ... when you try something new, when you play where no one else is playing, it feels really risky. It feels risky because it's uncertain. But what we now know is that when you take on competitive risk, that actually feels less risky, but it's more risky.

So for example, let me give you a better ... let me give you an example. So if you decide that you want to go after a job, and you see that there's a job posting on LinkedIn, you know that there's a job. You know there's a job, right? It's on LinkedIn.


But you have to figure out if compared to the 50 or 100 other people that are applying, you can compete and win. So you're taking on competitive risks. And the odds of winning when you take on competitive risks are six times lower than when you take on market risks.

So it feels more certain, but in fact, it's more risky. so then if you can tell yourself, all right, I'm gonna go try something. I see a need that this company, like HubSpot, needs to solve, and I see a probably that they have, but I don't ... but there's no job posting, but I'm gonna approach them, and actually, Valentina, listen to one of my podcasts. It's Sarah Feingold. She went to Etsy and said, "You need a lawyer. Hire me." This is a great example of this. So you don't know if there's a job, but if you can persuade them to create that job, to create that market, then you're gonna get the job. The odds are a lot higher. So the odds are six times higher.

So if you can arm yourself with saying, "I'm scared. Oh, I'm supposed to be scared." And, "Oh, this feels less certain, but I'm gonna be more successful if I'm willing to go where it's less certain as opposed to this place over here that feels really comfortable, which is more risky." So those two things can start to help you navigate that risk.

Yep. Sometimes it's all about just taking that deep breath and going with where it's a little more scary. But definitely check out that podcast. I loved it. I listened to that one recently, as well, so.

We've got a few more here. From Lawrence, "What's the best approach to broaching disruptive ideas with the boss?"

Oh. Thank you Lawrence for asking that. So what I would say is let's go back to the number four, and we kind of touched on this earlier, is sometimes ... whenever we have an idea, because it's our idea, it's brilliant. But our boss doesn't know it's brilliant. And so ... and yet, our tendency is to say, "Well I know it's brilliant, so therefore my boss should know it too." Well, they don't know it too. Again, you're asking them to jump to a new curve with you.

And so, when you're trying to broach these ideas with your boss, say to yourself, "How can I de-risk this idea so that my boss will want to adopt it?" What do I mean by that? You can de-risk it by number one, figuring out what language your boss speaks. Maybe your boss is a money person or a numbers person. Well then, don't talk about how this is gonna be good for your brand. Talk about how it's gonna be good for your bottom line. So figure out the language they speak. Speak that language.

Number two, start to gather data. Do research. Figure out what that idea is and why you think it could be helpful or beneficial, not to you, but to your boss and your team.

And number three ... I had a number three, and I can't think of what it is. I don't remember my number three, Lawrence. I'm sorry. If I remember what it is, I will come back to it. But that gives you a good start. Just remember that you're trying to de-risk this for your boss, and if you can put it in a language that they will understand and be humble enough to do the hard work of getting buy-in from them, then you are much more likely to get your ideas adopted.

Often, I think language is huge. We talk a lot about that with our customers, in making sure that we're speaking the language that they can understand. Whether they're a marketer or someone who's a little more technical, your language is gonna really shift between those two things, and it's gonna apply the same when you're going to get buy-in from your boss.

That's right. Exactly.

So i think we're gonna go with our last question here. It's from Kelly. She asks, "How do you counter people thinking you're overqualified when you're really just trying something new?"

So ... oh, okay. So I'm gonna extrapolate a little bit here. So what I think, let me assume, that you're saying you want to try something new and people are looking at you going like, "Why do you want to do this? You're qualified. You're gonna leave quickly." I think it's a fair question, because we know that you're gonna be a better employee if you're really challenged and engaged, and so I think that probably part of the narrative ... first of all, sometimes overqualified is code for, "We just don't want to hire you." Meaning you don't look like how you need to look, or you're too old, et cetera.

So you need to kind of tease out, what do they mean actually when they say I'm over ... or you're too expensive. What do they mean, actually, when they say I'm overqualified? And if you can tease that out, or figure that out, then from there, again, you gotta figure out a way to connect the dots for them to see why it will create value for them to have you there. But always go back to what is in it for this person to hire me? And why does it make sense for them to hire me?

And one of the things that's hard is when you're looking for a new role, we feel a little bit kind of needy, because we're ... just this sense of like, I don't get this job, I won't feel valuable again, talking back to the failure. But if you can always put yourself in their position, that will help. But I would begin again by trying to tease out what exactly do they mean when they say I'm overqualified? Is it code for something else?

Interesting. I think that's good advice for Kelly. And we're just about out of time here. So I wanna say thank you for reaching out to me when I very quickly tweeted at you after I fell in love with Disrupt Yourself.

Aww, thank you.

And for coming to our master class today.

So, who gets the books? Who gets the books?

So it looks like here, Jason was our first real question. I think Anna had a really great one, and Lawrence. It looks like these t our three potential winners here.

Okay, so Jason, Anna, and Lawrence, if you ... when you email Courtney, just make sure you give her your address, and if you want, just tell me a little bit more about yourself, and then she will pass that along to me, and I will send that off to you in the mail in the next week or so.

So thank you everyone for being here!

Yeah, no, this is great. So Jason, Anna, and Lawrence, please send me an email. You can find my information, you can tweet at me, CSembler. You can tweet at Whitney for sure. But you're getting some books coming your way!

Fantastic. All right, Whitney, you have a great rest of your day.

Thank you. All right, take care, Courtney. Bye bye.


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