EntreLeadership - #315: Learn to Navigate the Messy Middle of Business with Scott Belsky

Episode Date: April 22, 2019

As any entrepreneur will tell you, bringing a new idea to life can be unpredictable, but best-selling author Scott Belsky says there is one thing you can always count on: a messy middle. And that’s not necessarily a bad thing. In fact, Scott, who has worked with former start-ups like Airbnb, Pinterest and Uber, insists that this volatile time between the start and the finish of a project is the most crucial part of any venture. Tune in to find out why, as well as how to endure the tough moments and optimize the successful ones.   entreleadership.com/podcast Buy the book: The Messy Middle Scott Belsky's website #192: Scott Belsky—Making Ideas Happen Making Ideas Happen Necessary Endings Get your Summit Backstage Pass   Want expert help with your business question? Call 844-944-1070 and leave a message or send an email to [e-mail]. You could be featured on a future podcast episode! Learn more about your ad choices. Visit megaphone.fm/adchoices

We're not our best selves at either the lows or the highs. At these lows, we tend to make decisions out of fear. And at those highs, we tend to falsely attribute the things that we did to the things that work. Helping business leaders grow themselves, their team, and their profits. This is Entree Leadership. Now, here's your host, Ken Coleman. Coming to you from the Music City, this is the broadcast of leaders by leaders for leaders. Thank you so much for joining the conversation.

Our feature conversation is with Scott Belski, and we've got the Summit Backstage Pass. But let's start off with Scott Belski. Scott's one of the most, I think, bright thinkers in the country. The guy has been somebody that I've followed for a very long time. He's got a new book out called The Messy Middle, finding your way through the hardest and most crucial part of any bold project or new venture. He's currently the chief product officer for Adobe and executive vice president, of Creative Cloud and, of course, a best-selling author.

If you're one of those folks that likes to go back and kind of tie in the episodes, he returns to us, of course, this episode, but he was on episode 192. So, without any further ado, here is my conversation with Scott Belski. It's always fun to talk to you, Scott. In fact, it's almost eight, nine years ago that we first met a Catalyst podcast program that I was hosting at the time. And I'm so excited about this book, specifically the top. topic, The Messy Middle, because you shared this concept with me that many years ago,

and I think it's absolutely brilliant, and I think it's a vital conversation that we've got to have. So before we dive into the book and the content, we've got to start with what is the messy middle? You know, I think a lot of the greatest projects are inspired by a sense of frustration. And for me, my frustration was with our obsession with the starts and finishes of everything. and the lack of airtime spent on discussing the volatility in between the start and the end. Very bold projects or entrepreneurial ventures or turnarounds or, you know, just journeys without an end in sight. And it is volatile. There are tons of ambiguity, uncertainty, anxiety, anonymity that you're working through.

And those are the low points of the volatility. And then there are the highs, the things that work that you just need to do more of, whether it's how the product or service is working, how you're working, how you're team is working. And the funny thing is this, is that we're not our best selves at either the lows or the highs. At these lows, we tend to make decisions out of fear. We tend to get lost. And then at those highs, we tend to falsely attribute the things that we did to the things that work. And so whether we're at the low or the high, there are a lot of things that we need to think about in terms of how to endure those tough moments and how to optimize everything that works. And that, you know, that to me is

the messy middle in a nutshell. And I thought we needed to talk more about it. All right, Scott. talked about the fact that I'd heard this idea years and years ago. Now it's a book, and you just shared a great experience. But at what point does it become the content that you now teach other entrepreneurs and now you've written in this book? Well, I'll tell you the truth. When I came out with Making Ideas Happened in 2010, I said, I'm never doing another book. So, but what I started doing right at that time in 2010 is I started to capture the insights or the observations that I had either on a 2 a.m. phone call with someone, you know, a leader, going through a difficult decision or an acquisition or a bankruptcy or, I know, firing somebody,

that kind of thing. My observations in boardrooms, working with a number of other high-velocity startup companies. And also certainly my own experience, bootstrapping our business, Behance, and then going through a process of getting financing and then going through an acquisition and then being integrated into a big company, you know, and then leaving and then coming back. I mean, there was a lot that happened. And so I actually started writing down these insights and they had an Evernote file filled with about 820 or so of these things that really meant something to me. And at one point, I said, I should probably organize these. And that's where the Endure, organized, and finish, themes emerged.

And with that, I figured, okay, I should probably sign up and commit a couple of years to put this together and something that's helpful to others. And that's what became the messy middle. All right. So let's start with the first section of the book, and this is obviously a process. Endure. you talk about short-circuiting the reward system. This is if you're a booknote type of person. Pages 24-25 is where you really get into this. How do we short-circuit the reward system? Well, I think it starts by realizing that we are all governed by short-term rewards.

You know, from the moment of birth, we want our parents love and affection. We want to check on the test. We want to grade in the course and then the exam. I remember this somewhat crude point that was made in one of our 99-U conferences years ago by venture capital. New York named Fred Wilson, who proclaim that there are two great addictions in life, heroin in a weekly salary. And the notion that when you unplug yourself from something that you need to keep yourself going, you know, you're getting that salary, getting that paycheck, that's really hard. And I think we're actually fooling ourselves to think that we can be motivated by something that we want to achieve in five to seven years. Yes, it's enough to get us to start something, to take a new job, to take some risk in our career. But then when the reality kicks in, you realize

that you're falling behind on everything else in life. No one understands what you're doing or why. And it's actually very hard to stay loyal to a project for that long to keep the team together long enough to figure it out. And so I actually believe you have to short circuit their reward system in order to be able to do that. I remember two things that we did that were kind of funny back in the early days of Behance and bootstrapping our venture. One was I've been a lifelong vegetarian and the developers and the team figured it would be funny to get me to agree to eat certain types of meat at certain milestones that we might achieve over the next year. And I said, sure, you know, we probably will never get there. And lo and behold, you know, there was a Christmas

dinner or I was eating chicken off of a developer's fork. Wow. Did you get sick? I think people want to know. We can't move any further until we know if it made a little sick. I certainly felt a little sick. I don't think I got sick. The other funny one was that whenever we typed in Behance into Google, it always said, do you mean enhance? Do you mean enhance? And so we were determined to no longer be a mistake at one point. And then, you know, six months later, after a lot of SEO work and getting stuff done, one of our team members typed in B Hans. It came up as a legitimate search result. And that was like one of those, again, like short-term rewards we could celebrate to feel like we were making progress. And the last thing I would just say is there's a big

insight around the research that demonstrates that progress begets progress. It's a chicken and the egg scenario. We have to narrate and actually identify things we can feel we're making progress around in order for the team to make more meaningful progress in the future. Love that. Okay, so now let's move into Optimize. This is section 2. Pages 100, 102 is where you begin to see content on resourcefulness. This is actually a quote from the book. I'll just get to read it and let you teach on it. When it comes to scaling, the easiest path most leaders default to is to hire. But the best managers know that growing the team is not always the answer. Too many teams hire when they should be optimizing the people they've already got.

I think that's a mouthful. I think we stepped on all kinds of toes, which is good. Why is that temptation to just move to, okay, we got to scale, we got to hire? Well, listen, I think it's easy to solve any problem with resources. When we have more work to do, let's just hire another person, hire another person. And the problem with that is that that doesn't make something scalable. It doesn't make you more efficient. It doesn't allow you to do a little more with a little rest resources.

And so I've always firmly believed that resourcefulness is a greater trait than resources. In some ways, you could argue that resources is like carbs. You know, it just kind of goes away. But resourcefulness is muscle. It kind of stays with you. And if you develop it as a team, it sticks with you over time and gives you kind of superpowers and all the challenges you'll face ahead. And so as a leader, when your team is telling you we need more resources, we need more people.

I think the answer is oftentimes to refactor before you hire. Great. So you need more help. You know, find a new way to make your process more efficient. And let's go through another round where we are doing more with less before we choose to just throw more people or more resources at the problem. All right. Now, let's look about how they can actually begin to truly optimize. And you touched on that, but I want to dig a little deeper here. So we have a lot of small business. men and women owners that are listening to this program. And I think it's easier for them to jump into that trap of, okay, I'm going to hire some people.

But if they sit down and they go, okay, I'm going to listen to this Scott Belski guy. I think he's probably right. But how do they go about actually assessing the current team, maybe the individual, Scott, the roles to truly go, okay, where can I optimize versus, okay, this is not a situation where I can be resourceful, maybe I need a resource. I think that there's an art and a science to this. On the science side, it's, you know, in all forms of optimization in a team,

I'm a big proponent of the idea of A-B testing, which is typically used when we're building a website or something, and you make the button blue instead of green, and you see if it performs better, and then you revert to the previous version if it doesn't, and if it does, you just do another test and keep making the product better and better and better. There's a version of how we do that as teams,

where we stop meeting every Tuesday just because it's Tuesday and then we reevaluate three weeks later, did that make us more efficient or less? And then we revert to the previous version or we adopt the change and do another test. And I think it's important to do that in terms of who's leading different things as well as how you go about the work itself.

I would say that is a part of it. I also think it's important, obviously, to have an environment where you're constantly evaluating people. As a leader, being very forthright with folks about, you know, here's what I'm seeing and here's what I would have expected to see. Like, let's discuss the delta of that. And recognizing that everyone needs to move on at some point, whether it's internal or external. The truth is that as leaders, we love it when there's no change, when everyone's happy doing their job.

Yet the funny thing is that the only source of continuity and, like, growth as a company or an organization as a team is discontinuity. You have to move people around. You have to make sure people feel like their learning curve is steep. I mean, that's the only way you optimize the product that you're developing. And I think the greatest leaders get uncomfortable when everyone else is just comfortable because they recognize that maybe we're not pushing ourselves at the edge. That right there's a great statement, folks. Go back, rewind, play that, listen to that again.

Hold yourself to that standard. I think that's a great statement about the great leaders get uncomfortable when everybody else is comfortable. That's really, really good. Scott, you also say in the book that successful founders swear that hiring for initiative over experience is the way to go. I believe this too, but why do founders swear by this idea that you should hire for initiative over experience? I would say passion over proficiency. That's how I would say it. Yeah, it's funny. When my venture was started, we didn't have the luxury of hiring the most experienced people because they were too expensive. And a lot of organizations out there, especially non-professional. organizations, faith-based organizations. You're hiring people based on their passion for the solution, their passion for the problem, and you can't necessarily always hire the top people in the field for every single function. And so there's a luxury in not being able to do that, which is that you end up hiring people based on their initiative,

their past history of taking initiative and what's interesting to them, and your bet that they'll continue to do so. But as soon as you start becoming more successful, you get the luxury of being a resume snob. You suddenly start to want to hire the people with the right companies on their resume, the right experiences, the right titles. And that's when we start to sometimes end up hiring people that may have tons of skills, but aren't those who, you know, have the infectious initiative. It's interesting, you know, within an organization, initiative is infectious. It's contagious. Everyone sort of gets it from one another. But expertise is not the same way.

Like that sort of stays siloed. I've learned over the years that I try to optimize our. on the initiative side, because I find that in that situation, there's a resiliency in the team. People are developing each other into the roles that they need to play, as opposed to making the bet that if you just get everyone with the right skills, you're going to figure it out, which, you know, more often than not, doesn't actually work. How often do you see, Scott, when you get some people in with some serious initiative, that those that may be already there, and they start seeing that initiative, because we can all see it

and smell it, and then they see the results that those new, you know, excited energizer bunnies are getting and the recognition they're getting. How often do you see that it does rub off? Is that what you were referring to, that it becomes very contagious? I've seen a lot of culture change. My current role as chief product officer at Adobe. I oversee some new products. I oversee some products that have been in the market for 25 or 30 years. And some of those older products have people who've been with the company for decades in some cases. And I have, I have, found that when you bring kind of new perspectives and people with fresh energy and modern practices into a team, as long as there is a sense of respect for one another and a

really strong sense of alignment that what problem we're trying to solve, I do believe it's infectious. And I have seen a lot of people change as a result of that sort of mix. Okay, before we leave the optimized section, my favorite part of it is kill your darlings, just because I like the way it sounds, you know, it kind of gets your attention. It's certainly provocative. But it's also very practical. I'll let you unpack what in the world. Why are we killing our darlings? Who are the darlings? And again, why should we kill them? Right. It's an insight into the fact that especially the most creative among us, we love new ideas. We love getting excited about our work. Creatives, higher creatives, and it becomes this intoxicated, you know, crazy group thing that, you know,

never results in anything actually happening. Whereas the greatest productive teams in my experience, they are very good at building a very strong immune system in the team where you have the dreamers who are constantly thinking of the new ideas and new exciting things to bring to their colleagues next day and you have the doers who are sort of like the Debbie Downers of the world who are saying, hey, not on budget, not on timeline, put that in the parking lot we're never going to go back to and that if you can have the doers and the dreamers empowered at the right times,

then actually 90% of the time you have this strong immune system, the doers, that keep the team. team on track. And 10% of the time, it's sort of like the organ transplant where the doctor suppresses your immune systems. You can take on something new and sort of change who you are. And that's when you empower the dreamers to take hold. And so this immune system is very important in a team. And if you have it, then you are able to, what writers call kill your darlings. You're able to find those really exciting ideas that actually are liable to get you off track in order to focus on the most material, important stuff that is really going to make a difference and help you,

you know, change your world. In the writing world, sometimes this means the plot points, you know, the characters that are, that you're in love with, but really detract from the central story that you're trying to tell. And that equivalent of darlings that you must kill exists in every context, in every product or service or event, and the challenge is to identify them and to kill them with this strong immune system that I described, a team must have. All right. So we've talked about obviously two of the first three sections, endure, optimize. Now we're going to talk about finish. Oh, boy, everybody loves a good finish. Everybody, you know, it's a old modus, finish, strong, you know, finish, finish, finish. And I love this. You make a point very early on.

The final mile is a different sport. And I think that's absolutely really insightful. I don't think we think about it that way very often. Why did you use that language to frame it that way? Well, the final mile is indeed quite different. And it's interesting. We, we, spend so much of our time on making something happen. And then suddenly, the game changes. You either are about to launch the product or you're about to put on the event, you're about to sell the company, or you're about to wind it down. There are always these punctuating moments in life and in projects where everything does change. And the first thing that we oftentimes make a mistake with is we think we can still play the same playbook. You know, we think we are qualified, given the years that

we've been doing this to suddenly lead this next chapter when in fact we need to surround ourselves with different types of expertise and people and oftentimes empower different people to help us in this stage. Another insight around the end is there's a lot of strange sort of self-sabotage that actually happens in that final mile as well. As small as when a product or an event or anything goes live, you know, there's always these people who suddenly say, oh my gosh, we have to change this and change that and there's this notion of churn. that is more psychologically driven than anything else. And then in a more extreme side,

I've seen people go through an acquisition or some big moment in their work where they actually subconsciously don't believe they deserve it. And as a result, start to do things that destroy their likelihood of succeeding. It's sort of a scary pattern to see. And the reason I mention this is because, again, as leaders, we have to look at ourselves and our team around these finishes and try to notice anything that starts to go awry

because of these kind of final mile tendencies, as I like to call them. Now, there's a point in time, and you've moved on, obviously, and leaders have to at some point decide, okay, where are we going to finish, how are we going to finish? And you write about, if you can't end wonderfully and gracefully, this idea, you know, we never know how it's going to turn out, but if the end is necessary, our good friend Dr. Henry Cloud wrote necessary endings, you know, a wonderful book. Yep. So what's the best way to identify? okay, it really is, just in your experience, it really is time to end.

Now, I've seen a lot of different ends, especially as a person who advises many entrepreneurs through their journeys. I would say some of the worst ends are people who refuse to face the fact that it's ending. Right. And they just kind of go radio silent and there's no debrief. There's no post-mortem. There's no closure. Everyone's kind of left lost and carrying around this weight of something that isn't finished but is, you know, in the cognitive distance that comes with that. And then the best endings I've seen in even bad outcomes, but the best way, the graceful endings, if you will, are people who are very communicative in real time and they are willing to say, like, let's, first of all, make sure we get value from

this. You know, what are the relationships we've built that we now can say are an outcome that's positive? What have we learned? What should we have done? Let's spend the time on that. And let's really proactively communicate with all of our stakeholders, our customers that are going to get affected by shutting down a product, our investors who are going to lose their money. Let's really just be inclusive. And in those situations, in fact, I always leave with more admiration for the leader than I may have had when I originally got involved with the product or the team. So it's important to think about the graceful endings because, you know, it sounds cliche, but it's true that every ending is a new beginning because it changes your reputation. it changes your network, and you can either leverage all of what you just went through, the people and the lessons, or you cannot, and that's up to you.

That begs the question. I love the title, the book, The Messy Middle. So I'll ask a messy question really on subject with what we just talked about. And that is, sometimes it's so hard for leaders or just quite frankly, let's just talk about humans. It's hard for us as humans to want to walk into a situation that's not working, broken, messy, whatever you want to call it. And it's just not fun. And we tend to kick the can down the road. We'd rather not think about it. I was guilty of this just the other night, Scott, just as a parent. I got three kids, you know, 13, 11, and 10. So do I. And I was dealing with not a crisis,

but a behavior situation. And my wife was telling me about it. And it's 10 o'clock. And I'm in bed reading. That's what we do, you know, wild and crazy nights here at the Coleman house. And she comes in and his husband, wife, will do. And she says, you know, this is going on here and just want to make you aware of it. And I just said, you know what, I can't, I can't think about it right now. I'll talk about it tomorrow. I can't deal with it. I'm exhausted mentally, emotionally, good day, but just nothing there. And I put it off. And I think we all are there, whether the situation is business or relationships. Here's my point. I was trying to call myself out, Scott, that when I actually, though, dive into it and put the effort to get into it, it's not as crazy, scary or

crazy, messy as I thought it was. And I actually have to be uncomfortable. I have to put myself in that situation to actually find out what is the real solution going forward. But ignoring it, it's not going to make it go away. So why do we do this in business? What's the temptation? Well, the easy answer is that the easiest decision to make is to not make a decision yet. And we see that all the time, you know, in teams and products and organizations, large and small. And it results in what I like to call organizational debt, which is the accumulation of decisions that should have been made but weren't. And that debt slows down people. It demoralizes people. It hurts customers or constituents. It just sits in the workplace. And in the world of technology, there's this term technical debt,

which essentially grows over time and makes developers slower and actually ultimately hurts the product and the ability for it to get better more quickly. It's the same thing in how an organization functions. And so to combat this organizational debt, we have to adopt a few behaviors. I mean, one of them that I think is really very crucial in fighting bureaucracy and preventing organizational debt is to ask the annoying questions when you have them, despite the fact that they may come across as annoying. You know, if you're discussing something with your colleagues and someone says, oh, you know, legal says we can't do that or, you know, or the dates don't work.

And then someone just sort of caboshes the whole conversation. And are you the type of person that says, well, who? Who said that? And can we get a meeting with them on the calendar right now? Oh, they're out? Like, let's actually call their assistant and get a meeting for next week when they're back. Or the fact that failed before. Like, why does that mean we can't try it again? Let's dissect that. Let's not so easily dismiss this. You know, these questions that we ask are what keep the ship moving. And in an organization, you can always get to a great end. It's just a matter of keeping motion. And I like to think of that frigid ocean that's just about to freeze over. and that big ship that if it stops for any more than a moment at time, it's stuck and lost forever.

But you keep asking those questions and you keep that ship moving, you will get there. And if we can't get a decision, get a decision and when I'll have a decision. Good stuff. The book is The Messy Middle, Finding Your Way Through the hardest and most crucial part of any bold venture. He is Scott Belski. He's been on the program multiple times. He's a great thinker, folks. This concept has been alive for a long time, and now he puts it out in a book that, by the way,

a it's big Scott I gotta give you credit it's big it's thick but it's actually really digestible short chapters you're moving along through it I think it's a great read folks and we have a lot of guests on the program and I got to tell you something Scott ever since I first met you those catalyst days I don't even know if you remember that back in I do I do of course of course I do I gotta give a pitch to making ideas happen too I I think that book and this book is required reading for anybody who believes they're created to do something and that it matters and it must be done because this stuff is not just practical. It also is inspirational. So, Scott, you know you got a lot going on, but we always love talking with you. We're better for having you

on. Thank you so much for having me. Really enjoyed it. Always love having Scott. Hope you enjoyed that as much as I did. We love giving you the access to leaders like Scott Belski. And so since we like to give you access, how about giving you access to our premier event, the Entree Leadership Summit? We do this with the Summit Backstage Pass. I've told you about this before. I want to remind you that this event has been sold out for many, many months, but we want to give you our podcast listeners some access to the event. Through the Summit Backstage Pass, we're going to give you the keynote addresses from Dave Ramsey, Chris Hogan, and yours truly, along with a digital copy of the workbook. So as you're listening to the talks, you can follow along and take notes just like the attendees. If you'd like to

take us up on this special offer, it's free. Text the phrase, Backstage, Pass, no space, backstage pass, text that to 33444. That's 33444, or you can click on the link for the backstage pass in our show notes. Well, I want to say a big thank you as we do every episode, but I want to say a special thank you because you, the audience, are the reason we do this program and you are the reason we continue to get to do it. If nobody's listening, we're not doing it. And you are listening and the program is growing. And we appreciate that. And if you are a regular consumer of this program, we would like for you to consider subscribing. Now, you've got all kinds of podcasts that you have the opportunity to listen into.

But we'd love for you to subscribe in Apple Podcasts or wherever you get your podcast. That would be a huge favor to us. That helps us continue to grow. And we'd ask you to consider doing that. Thank you, thank you, thank you for that. Well, that is going to do it for this episode. So on behalf of the entire Entree leadership team, thank you so much for listening. We'll talk with you again very soon.

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