Greatness Requires Discomfort

David and Blair each share their own perspectives on how chasing comfort has kept them and their clients making the right decisions in both management and sales situations.


2Bobs Episode 2: Say What You Think

The Challenger Sale: Taking Control of the Customer Conversation by Matthew Dixon


BLAIR ENNS: David, you and I spoke at the same conference three, four days ago. It was really great to see you again.

DAVID C. BAKER: It's great to not see you again. I didn't see you, and the poor suckers, all the people that... they were exposed to you after me, which meant I could not correct all the misstatements you surely made. I heard that you were not all that respectful to me from the podium.

BLAIR: I am always respectful to you, but I do take a few potshots, so I just... I'm sure this happens to you where you're about to give a talk in a few days and the organizers say, "Hey, send us your introduction", so I sent them my introduction. I wrote it on the plane as I was flying there, and there's one of those situations where they ended up reading it exactly as I'd written it. Now, I'm not going to read it all, but I'll read the last line.

DAVID: Oh no.

BLAIR: So there's the usual background, and then it says, "Blair also cohosts with David C. Baker, the podcast 2Bobs: Conversations on the Art of Creative Entrepreneurship. As listeners know, Blair is the smarter, more successful, and better looking one." I got a round of applause. All of that is true, thought, too, so I...

DAVID: That was a fun... I really enjoy speaking at events and I know you do, too. It's like fresh victims all in one place. At a certain point in your career, you're not afraid of any question they might ask, and it's always interesting because people come up and throw some new ideas at you. I think I might die if I didn't have the opportunity to speak from time to time.

BLAIR: I'm with you, too. It was a fun event. I was arriving, landing just as you were taking off, so we didn't get to see each other.

BLAIR: Let's get to the topic of the day. Unlike some of the recent ones, I love this topic that you've come up with. Greatness requires living with discomfort. What do you mean by that? High level, what are we talking about? What's the principle here?

DAVID: I think maybe the idea came to me... I was part of this small Facebook Group for speakers and authors and somebody was talking about how they had just upped their fee on a proposal to somebody and they were sitting here anxiously waiting to hear back. I just wrote them a brief note and I said, "As soon as you start getting comfortable with your pricing, then you probably need to raise it a little bit."

DAVID: That's kind of a silly thing to say, but there's something about how once we get comfortable, then certain things stop happening. Certain good things stop happening, and it just got me thinking about how our desire for comfort keeps us from doing the right thing sometimes, and then as I was thinking about that a little bit more, I just tried to write it out. It was like, "Is that really true?" How many different places might there be in our lives and our businesses where our chasing of comfort keeps us from making the right decisions?

DAVID: I don't mean to be silly, stupid, bumper sticker "The only certain thing in life is that there is no"... that's bullshit kind of stuff. I just can't stand hearing those statements. I don't mean it quite like that. I want it to be a little bit deeper, but that's sort of the sense of it.

BLAIR: When you sent me a note on this with a few bullet points and said, "Well, let's just have a conversation on it and see where it goes", I immediately thought, "Man, this is a really big topic", because it ties into some of the things that we've talked about before. We were talking about how you define success, and at some point the conversations steer towards happiness and I said, "Maybe that's a more relevant question."

BLAIR: I don't remember if we talked about this point. The pursuit of happiness... happiness is something you need to pursue kind of obliquely. If you pursue it directly it doesn't really work, and then the question of happiness. When are you happiest? You're happiest when you're growing. What does it mean to grow? It means to push through the barriers, which is almost always uncomfortable. It's not the barriers through hard work, it's bringing yourself to do the things that you could not previously do, and we'll bring this back down to the specifics of our audience in a minute and how we see this play out in your consulting practice and in my training company. Really, growth, that's what I want out of life, is I want to keep growing.

BLAIR: I want to have an impact on people, but I want to keep growing and I know you value you that, too. Growth really is about pushing through these uncomfortable areas, so I think seeking to be happy in some ways maybe just means seeking to avoid discomfort, and that's not... Okay, now I'm like rambling. Stop me, save me.

DAVID: I understand exactly what you're saying, and I'm thinking about some of the political polarization that's happened how... In the morning, I don't want to read the publications that believe like I do. I already know what I believe. I want to read the publications that make me uncomfortable, and then I want to figure out, "Okay, where's the kernel of truth in here? Where are they maybe right and I'm wrong? Why do I feel uncomfortable about this?" It just carries over into so many different other areas.

DAVID: Maybe we aren't even living if we're not learning, and maybe we're not learning if we're not uncomfortable. Maybe we're not really running our businesses well unless we're uncomfortable in some way. If we just translate this into people for a minute, where everybody is kind of happy, nobody is pressing you for more money, you're winning the right number of proposals that you're making. You've got enough money in the bank. Everything... it almost feels a little bit fragile, and it's because you know it won't necessarily last and it's not hard to be happy in those moments. The leaders are the leaders who steer the ship ahead when everything is falling apart. That's what makes these amazing commercial pilots, the real pilots who don't lose their head and they do the most important things and they can push all of this discomfort aside and not lose their head.

DAVID: It just seems like we have to accept and almost embrace, not seek discomfort, but embrace and understand that it is a real part of life. If we try to push discomfort out, we're not really living.

BLAIR: I agree with you, and I immediately thought of all of these scenarios where I'm coaching somebody to do a specific thing in the sale. The big thing that I think might be hardest for most people is to accept the fact that the person that you're dealing with is not the right person and you need to get to a more senior decision-maker. You need to have an uncomfortable conversation with this person that essentially says, "Listen, I value this conversation, but I really need to speak to your boss or the people who are really going to have the authority for this", et cetera.

BLAIR: Everybody understands at some level that you want to be better at sales. You need to be able to have those conversations, but everybody comes up with reasons not to do it. It's hard. I often hear, "It's just not polite. It would be rude". The truth is, it's not an issue of politeness, it's an issue of discomfort. It's not an easy conversation to have, and if you look at people who are successful in life, they lean into the uncomfortable places and they have those difficult conversations.

BLAIR: There's a great book written on it, and I think I've mentioned it before, it's called Crucial Conversations. Oh yeah, I told the story about finally having a crucial conversation with my wife and I look over in the car and I think, "Wow, I feel so good", and I look over and she's crying and I realize, "Oh, okay, so maybe there's some nuance around this I got to learn to get better at it."

DAVID: "Maybe I should reread Chapter 7 or something."

BLAIR: We've talked about it. She's forgiven me. That's just an example of getting to decision-makers in the sale. That's not an easy one, and the easy thing to do is to politely respond to the RFP. It's to follow the procurement path or selection path that the client has laid out rather than push back, rather than challenge.

BLAIR: That's just one example, but let's talk about some more. Where are some other areas where this principle, this requirement to deal with discomfort if you want to be great, where does that show up?

DAVID: One of the places that I think our listeners will identify with really right out of the gate is not wanting to release a service offering or maybe release something that they've written that just doesn't seem quite ready for prime time. This isn't something that I've thought too much about. This comes from other people that I've read and listened to, and so many of them, the common theme has been partly what's made them successful in their businesses is that they are willing to throw things out in public before they are perfect. They're willing to live with that discomfort of possibly being wrong, possibly being questioned by a lot of people. This example is probably not where our listeners thought we were going to go first with it, but I think it's a really good example.

DAVID: I find myself, even though I haven't thought about this as a concept too much, in my own experience I find this happening. "Do I really want to hit "Send" on this thing that's going to however many people?" I'm not worried about a typo. Those happen, I don't like those, either. I'm more worried about, "Am I going to look stupid?" Or, "Am I in the wrong mood right now?" Or, "Am I trying to hard? I just keep second-guessing myself and not willing to live with some discomfort." That being the leader means you are living with some discomfort and you are calling things before clarity exists.

DAVID: Whether it's service offering or whether it's some new piece of insight, whatever it is or how you're leading the client, I think this is where our listeners will really understand what we're talking about here.

BLAIR: That's interesting. As you're talking, I'm thinking the notion of MVP, minimum viable product, which is... it can't be more than a decade old and it comes out of the software development world and it's been adapted into kind of the larger creative world to a certain extent when it comes to digital products, websites, et cetera. That's a new concept, the idea that you don't wait for it to be perfect to ship it, because with digital products in particular, you can refine the product once it's in the market.

BLAIR: There's even a point of view that, "Well, you use the market feedback for the refinement", so you just put the minimum viable product out there, then you iterate based on feedback. I think that's a concept Seth Godin talks about. You've got to ship, you've got to ship. Get something out there. You get to check the box that I've shipped, and then you're kind of reserving the right to improve it as you go.

BLAIR: I think people of a certain age, maybe our age and older, they're not as comfortable with that concept of... they want everything to be perfect before they press "Send" or put something out in the marketplace. It feels to me like it's a newer approach to business.

DAVID: It's more of an agile approach, for sure. Have you seen the movie Free Solo?

BLAIR: Yeah, yeah. I'm familiar with it. I haven't seen it. I've seen the trailer for it. I know how it ends.

DAVID: You know... Yeah. Hopefully this is not a spoiler moment for people who haven't heard that he died in the attempt. No, I'm just kidding. What did I say?

BLAIR: Why don't you give away the Game of Thrones ending, too?

DAVID: I don't go to theaters because I just can't sit still that long-

BLAIR: You're banned for life from most of them in Nashville, but go on.

DAVID: Every once in a while when I just don't feel like working or writing or whatever, when I'm on a long flight, I'll watch. I was watching that on a flight back into the U.S. last week. I was just absorbed in this thing. It was just amazing. I am not a rock climber, so I don't even understand some of the language, but I found it so fascinating that this guy just would never rest. I was thinking about how you climb up to a certain point and there's a base camp and then there's this rest area that you reach after five hours and you can camp there and then go the next day further. These people, they just never stop, and he... If you don't want the spoiler, then skip past this, but he did do it and he did it in like four hours and never stopped.

BLAIR: It's El Capitan. He's free soloing, so no protection, no safety net basically. He's not roped up. He's free climbing this thing, and one small slip and he's dead and it's all captured on film. I saw the Vice-President of something something from North Face Films do a talk a few months ago at a conference I was at and he was talking about the internal discussion that went on for months about the ethics of, "Should they film this?" It was fascinating. I cut you off, but talk about pushing yourself through discomfort.

DAVID: He was okay living with discomfort. He was okay living with the fact that he might fail. Living with the fact that he might die, that he might disappoint these other filmmakers who were all professional climbers. It was done by National Geographic, and there was just constant... there just was never enough discomfort for him, but it didn't mean that he was reckless. He was very, very careful, and he worked on his craft. He'd get up at 4 in the morning and hang by his fingers from this improvised little hanging thing in his van that he lived out of and do pushups. It wasn't like he was reckless, he just kept pressing against that and pressing against the level of success he had already reached, which was very significant.

DAVID: In our businesses, we reach this new level. We want our revenue to be $10 million this year. It's just kind of a crazy goal. There's no particular mathematical reason, it's just, "Let's all work together and let's do this", and then you reach it after a lot of hard work and then you think you've got two options at this point. Should I just kind of rest for a little while? That's really what most everybody else that works for you wants you to do, but you know... you say, "All right, what's next?"

DAVID: It's what makes you different is you're almost drawn to discomfort, which is different from risk, but there is a little bit of overlap. It's not one of the only things, but it's a really significant part of what makes great principals at firms is that they're willing to live with this discomfort. That means pressing the prices, having those tough conversations with employees, throwing a service offering out that we're not quite ready. I don't want to imply that they're being reckless, I just want to imply that they're pressing the boundaries.

BLAIR: That's the nature of leadership. Leadership is essentially saying to the team, "We're going in this direction", and then have everybody feel compelled and inspired to want to follow you. Now, that's super easy to do when there's no pain or discomfort associated with the direction. The mark of a great leader is you can say we're going in this direction seeking this seemingly impossible outcome or task and have people inspired to want to follow.


BLAIR: There's a famous line. It's some guy whose name escapes me. It's been around for years, but it's not so famous I can remember his name, or even directly remember the line, but I've repeated it in bastardized forms for many years now, and it's "Successful people do the undesirable tasks to get to the desirable outcomes." The vast majority of the people will avoid those undesirable tasks. It's really about pushing through that discomfort, and I've seen this. You look at people who are told by their doctor, "Listen, if you don't start exercising or change your diet, you're in serious jeopardy." The vast majority of people will accept their fate and not change their diet or exercise routine because it's just too uncomfortable, it's too difficult for them.

BLAIR: This idea that people can learn to do this, yeah, everybody can learn to do this, but how few people on the planet really do learn to lean into discomfort? I'm not claiming that I'm in that category. I have my successes and I have my failures. It is interesting to note how many people just cannot bring themselves to push through discomfort.

DAVID: You and I are going to dinner somewhere in London and the waiter brings a menu and says, "Hey, can I get you a drink?" While you're thinking... I immediately look at the special drink menu and try to find something fun and I'll send a picture of the menu to my oldest son who's really good at that stuff and he'll tell me what I should order, and you say, "Oh, I'm not taking any alcohol now." I'm thinking, "What?" For you, you're just experimenting with something else in your body. You just have this like laboratory. This is your hobby, right? I just think, "Oh, well, I don't know what the reason is, but that just sounds like too much work to me."

DAVID: Thinking about what kinds of discomfort might keep a principal from being successful, it might be what they really think is worth experimenting with on a positioning decision, but they don't really want to deal with employees who might be dissatisfied with that direction, or more likely, it's having somebody on staff who's a really good person deep down and who is very qualified, but they're not as self-aware as you'd like and you need to have one of those uncomfortable conversations with them. If you don't, the firm is just going to get stuck because this person is important in the organization.

DAVID: All of you fine folks listening, you know exactly who I'm talking about. This is a real person. You know who this is, and you've put this off because of the discomfort. Believe me, I understand. Anybody in any kind of relationship, it doesn't matter if it's official or not, you have these moments when this kind of thing happens. I was in a meeting yesterday and somebody said something that was kind of off the wall and painting with a broad brush and it made me cringe a little bit. There was this silence and everybody is kind of looking at each other and wondering, "Oh, okay-

BLAIR: Who's going to be the adult? Who's going to step and say what needs to be said?

DAVID: I waited a while hoping somebody else would.

BLAIR: That's what happens, right?

DAVID: Nobody else did, so I did, and I kind of used some humor and I just said, "That might be painting with a pretty broad brush, don't you think, folks?" Everybody laughed and we moved on, but that's just a very small example that's making light of some of the more difficult conversations that need to happen. It just... I don't even know where we're going with all of this stuff. It just feels like there's so much here that we just need to keep reminding ourselves, let's not run from discomfort.

BLAIR: As we talk about it, I think the vast majority of this discomfort that we experience that you and I are essentially counseling people to lean into, and if you're feeling uncomfortable, go towards it not away from it, the vast majority of it is in conversations we're having with other people. We did a whole episode on one of our core values at Win Without Pitching, which is say what you're thinking. That idea in that situation, you're struck with this thought that needs to be said, and so you bring yourself to say it.

BLAIR: Again, I think of the sales role. It's about getting access to decision-makers. It's saying no. It's pushing back on a flawed selection process like RFPs. It's difficult conversations with your employees. At the conference you and I were speaking at earlier this week, I did one of my absolute favorite talks, The Five Constraints, where I introduce the audience to the wonderful world of Blairtopia, and I say, "In Blairtopia, all firms not just succeed, but thrive, and they thrive because my rules are essentially the laws of nature. You have to follow them."

BLAIR: We do this series of constraints-driven exercises, and I give them five constraints, one at a time, and I try to get them to try it on. The first one... we've talked about this before, the first one is No Exit. You can never sell your business and you can never retire, and then I give them a minute and I ask them to close their eyes and think about, if you were going to live by this constraint, what are the changes you would need to make in your business, first of all? What are the changes you would need to make in your life? We have a discussion around it.

BLAIR: As I'm leaving the conference the next day, I'm in the elevator. I ran into somebody. She's got this steely look in her eyes. She said, "Thank you for a great talk yesterday. I'm going home to have some difficult conversations."

DAVID: Oh, wow.

BLAIR: It's really about, if you saw your business as a life sentence and there was no exit, what would you do? You would lean into discomfort. There are all of these issues that you're just kind of... especially when you're older. If you have a vague or specific idea of when you're going to retire, you quit making these decisions, and we talked about it before, but I think this is probably one of the most valuable skills that anybody can cultivate, is the idea that when you're feeling a little bit uncomfortable about something, you go for it. You lean into it rather than lean away from it.

DAVID: Yeah, absolutely.

BLAIR: I lean a lot, or I refer a lot to the book The Challenger Sale that's backed by some remarkable research that shows that in a B2B sale, and in particular, complex B2B sales, the type of salesperson most likely to succeed meets this challenger profile rather than a relationship builder profile. They kind of tested five different profiles and the hypothesis of the authors, of the research in the book going into this was they thought the research which showed that the relationship builders are most likely to succeed, and they showed that challengers are far more likely to succeed. In a really complex sale, they're more likely to succeed over relationship builders by a ration of about 11 to 1.

BLAIR: Now, the hallmark of a relationship builder is a relationship builder seeks to ease tension in the sale, and a challenger seeks to create tension in the sale. When you just put those two concepts on the table, people, their eyes just widen. There's this rigorous research that backs these findings, so you just imagine somebody who's smiling and nodding "yes" and who wants everything to be okay between them and the client, they are far less likely to succeed than the person who, similar to the situation you recently found yourself in, there's an uncomfortable moment, they lean into it and say what needs to be said. They push hard to get access to decision-makers, and now I am extrapolating from the research to other things that I see, but basically, just being willing to create tension in the sale gets you further ahead than trying to ease tension. I think it's very easy to extrapolate that concept from sales into broader success in business and in life.

DAVID: Let me pick up that mantle and translate it to managing people. I can't cite this as scientifically as that source does, but I have now read surveys from every employee that 1,340 principals manage. That's 1,340 principals. I've read a survey from every single person that answers to them, and one of the themes that I've seen in terms of how grateful these employees are for their particular manager and his or her style is that there's always the things that you would kind of expect, but the one that seems to be the most emotive for these people is that, "I always know where I stand. I don't always agree with it, but I always can count on knowing exactly what's in their head. I know where I stand. They communicate with me frequently and I really appreciate it."

DAVID: These people are not reading those uncomfortable conversations, some of them, not all of them are uncomfortable, but they're not reading that as bad. They're reading it as something that... it improves their career in a much quicker way than it would otherwise and they're so grateful for that kind of a manager that doesn't step away from the discomfort. They're not wanting their manager to always be right, they're wanting their manager to always be present and in those conversations with them. I think we can apply what you said on the sales thing, right to the management thing, too.

BLAIR: That's really profound. I'm not surprised to hear that, but I hadn't thought it would be kind of the number one insight that bubbles up through that. It reminds me of a few years ago I was doing some training with a client and then a couple of weeks later, he called me. He said, "Hey, can we have a conversation?" He said, "I've been warehousing some stuff", and I thought, "That's an interesting use of the term." He said, "You said two things", where essentially I either offended him or he felt like it was unprofessional. He just couldn't hold onto it. It wasn't an easy phone call for him to make, but I was so appreciative of the feedback, and I realized he was right on both instances. I was in the wrong to have said what I said in both cases.

BLAIR: We were fine after that and I continue to do a lot of work with him over the years. It just always stuck with me about how that was not an easy conversation for him to have, and I really appreciated that he picked up the phone and made that call, rather than continuing to warehouse, as he said, those feelings. I can see that, and as we're talking about it, I realize that I don't do this nearly enough. I think there are times when I'm pretty good at it. Probably almost everybody is like this is my guess. There's a time when it's like, "I'm just going to let this one pass."

BLAIR: I really respect those people who don't let even the little ones pass, and I'm not saying don't give people a free pass on behavior when they're having a bad day or something. Sometimes that makes sense. You know, if you have any level of emotional awareness and emotional intelligence, and nobody really understands how much or how little emotional intelligence they do or don't have, but if you have even a modicum of it, you should sense when it's time to lean into discomfort, whether it's a conversation or a decision about the business.

DAVID: Always with grace and with mercy, and sometimes maybe you wait for six months or maybe you don't say it at all, but you have to follow your instincts to get better and better at that, about, what does this situation call for? Not because of something I need, but because of something the greater universe needs or this person needs. Whatever it is, let's make sure that discomfort is not the reason why I'm not doing it.

BLAIR: I wrote down something you said back at the beginning of this conversation, and I just wrote down the word "fragile". You were talking about things are going well, clients are happy, et cetera. This moment where the climber would take a rest, but you don't rest. As you were describing that period of kind of grace or comfort or maybe complacency, I got this little knot in my stomach, and then you said the reason you don't rest, you didn't say this, you kind of implied it, is that you're just worried that it's not going to last.

BLAIR: We've talked about this before, so I just want to put a bow around that. The idea that, "I feel good about success when I'm still moving." Whenever I stop and think, "Oh, I'm just going to enjoy the fruits of my labor and the risks that I've taken and we're just going to coast a little bit", there's a little voice in my head that goes off that says, "Don't you dare stop."

DAVID: You're standing on a pile of fire ants and you just don't know it yet. Looking at the view, and you start to feel an itch and it's like, "Oh, shit!" You rip your pants off. That's what it feels like when you don't keep learning. We don't want to define success exclusively by money, for sure, or size. We want to define success by not moving and continuing to learn and doing the right things and the right environments and not avoiding things because they make us uncomfortable.

BLAIR: All of those things are uncomfortable. That's where we learn, that's where we grow. The joy is in the struggle. Let's stop there.

DAVID: Yeah, why not? Right?

BLAIR: This is great. Now, I'm going to go have a little rest. Lie on the beach and let everybody come for me.

DAVID: As soon as you fall asleep, I'm going to dump a pile of fire ants on you. Thank you, Blair.

BLAIR: Thanks, David. Talk to you soon.

David Baker