262: Scott Belsky, how to avoid and recover from the distractions that can derail your progress


Hi! This is Scott Belsky. Author of the messy middle and you are listening to my quest for the best with bill wrinkle. Listen up small business founders, senior managers and rising stars Bill Ringel here hosted of my quest for the best where ambitious small business leaders discover, strategies and tactics unlock your broke potential on each episode. Bring you the inside stories from published and accomplished guests who want to share their knowledge and experiences, so you can be more successful in leading your people managing Your Business and navigating towards more growth, the more impact in a changing and challenging landscape. Let's dive in. Hi. This is Bill Ringel host of my quest for the best we're embiid small business leaders discover strategies and tactics to unlock the growth potential. Joining today's Scott Belsky Scott's passionate to make the creative world more productive, connected adaptive to new technologies. He founded be hance, the leading online platform from millions of professionals in the creative industry to showcase and discover creative work, and served as CEO Until Adobe. Acquired Be Hansen. Two thousand twelve he has serves as a dubious chief product officer Scot actively advises than invest businesses that crossed the intersection of technology and design and help empower people his an early advisor investor in Pinterest Uber Cardis Week Green and Periscope Tim. Tim, few, he splits his time between New, York and San Francisco and he's here to talk about his book. The messy middle finding your way through the hardest and most crucial part of any venture, welcome Scott Thank you bill to be her. Scott one thing I'd like to ask all high-performance. Come on, the show is when you were growing up who someone who influenced or inspired him? Well give an answer that sure other folks have given before, but my father. He was surgeon and just a hard working doctor that I found. You know two things really striking to me one is. He was driven by empathy and just the nature of his. Side manner his willingness talk to patients, whenever about whatever also just the late nights where he'd the opt doing his dictation where he would you know, write or transcribe his notes for the day, and it just was a very important kind of person for me. My life in terms of what work ethic would mean for me. I continue to think about those thoughts often it leaves an impression when you see apparent putting in that kind of time and carrying bettas patients to that degree, and I'm sure that's made. Made, impression on you. Can you remember a time either throwing up early in your career? When you refer back to an example that your dad set free freedom, there's I remember. When I would be waking up in the morning for school growing up in the six thirty am or whatever and I'd be kind of dilly dallying, and and a little bit like intimidated by the day ahead of me, therefore especially tired the start of that he would come in already to go to work data early and. Despite having been up really late tonight before he would always say like come on, let's go. What are you waiting for? What are you waiting for in? You know there's that's like A. Soundtrack I played in my head over the years as I. Have also been those moments where it's just endless exhaustion and having to push for another day, especially during periods of uncertainty building, my business and you know other volatile periods. It was kind of a helpful memory that stuck with me. You started out writing. The middle was that after you head transition from the hints to Adobe with a messy middle was actually a combination of a lot of different notes, observations from board meetings three am to am to conversations with insurance going through an acquisition the next day. Like just the at the fringes of the experiences that I had as a founder, also strapped his business, and then you know advising others and dealing with. Just watching other stories I just kept writing down things that I didn't want to forget, and at ended up culminating in an eight hundred or so notebook of insights in my evernote at the time that I one day said you know what I should probably start categorizing these and looking at them like a puzzle. Like how do the together in? What can I learn from them and in that process I that? that. There were three major themes one win. During those lows, the second was optimizing everything that works both in your product as well as how your team works in the third, the final mile, not screwing it up, and so those three themes it became kind of the sub sections of the messy middle, and and over seven plus years of Janis notes down. You know that was kind of those are the kindling. To of the buck, won't that charts that appears very early in the book is relative joy of creating, and it should was have jewelry rises and falls over time, and it's really illuminating. Can you describe it in words will also posted on your page, and with credit of course, but can you describe how you actually came to illustrate that and capture that really important concept well I just think that we are governed by short term. Term reward systems as people from the birth. We are kind of seeking our parents, affection and care. We're seeking ratifcation. Thumbs up checks on task grades in courses and exams, and then as the venture capitalist Fred Wilson One said if the two great addictions in life are heroin weekly salary, you know we are also addicted to that. As a form of reward, and the short term of words are necessary for us to move forward and. And as a result whenever we have a bad grade, we think we should quit whenever you have a good grade. We think we're winning. And and it's always in the moment, and of course, in retrospect of any bold journey, what you learn is that it's just a series of these ups and downs, and and maybe the competitive advantages to sticking with long enough to figure it out the curve that I show in the messy middle is. Is that? It is intended to dispel the mess that an idea is exciting, and then it gets extraordinarily hard, and it's kind of a linear path upwards finish. That's not true. It's actually more when I describe. It's series of ups and downs of moments of despair followed by moments of promise, and if you can aspire for a positive slope meaning, not get so up and down, but rather just focused on incremental progress or at least. At least highs that were higher than the ones that came before them both are less lows at that's actually the holy Grail, and and that's the cornerstone of the book. Yeah, it's actually when you say spire for posits slippages want to really get more granular than that. It's like an ekg. That's stilted rising as it goes from left to right. Damaging their. Exclamations either listen, we're not our best selves at the Lowes why because we make decisions out of fear, because we start to think that we are doing something wrong, and then we're hasty. And we're not our best selves at the highest, because we falsely attributed the things that we did the things I work, we become high on ourselves and our we become overconfident in we become somewhat narcissistic to some degree on an art capabilities, and so I think that's part of the realization as well so preparation for this interview of conversations with other CEO's business leaders, suffering team leaders and podcast subscribers. Everyone can relate to the situation. The title describes because products product launches team projects client relationships, even the response to the couvert nineteen pandemic feels like we're beginning, and not nearly at the end one thing, a lot of people wanna knows is about domestic middle this petty define when we're in the middle and start to share it as a way to help. People Orient to know that this is something that is a natural part of projects and to start looking for ways to make progress in when it seems like things are in a huge mess either way I will. Will back into that answer is to say that in one of the trickiest parts of being investor board member you know when you have a conversation with a leader about whether he or she should quit or stick with it and 'cause. There's difficult periods of time you go through where there's no end in sight where you're low on runway for cash, and you're not sure if you can pay your employees drew three months, and and so it's during those calls where I always try to determine one thing with the with the leader, the founder of advised. That is their level of conviction in the end state of what they're trying to do in the world what the brand is! They're trying to build the problem that they're trying to solve. And I always ask so given all that you've learned so far. Do you have more or less conviction in state or problem? The way you see the world being, and if the answer is well, you know I had a great idea what I want to do with the problem was, but then after the last two years of customer research in partnering with People in what have you I actually have less conviction like I actually think we were off. Off My question is. Why should you stick with it? Maybe you should quit. Don't waste time of your life doing something enduring yourself. You don't have conviction in the state of it. Tell ever, however, if know, oftentimes the answer is well actually we have even more conviction have more data in more research. We know this works. We know that works. However you know there's no end in sight struggling running out of money, whatever and in that case I remind they're just in the messy middle. They're experiencing. What is par for the course and don't Overdo Mattis, is it? Your conviction is as high if not higher than when you started. You're making progress, even though it feels like you may not be and I think that's the distinction you're asking about whether you're in the middle or not, and it really does come down to that sense of conviction. The leader based upon everything that here she's learned. That's really important to emphasize especially in these times when we're in a very volatile time, and we're not connected physically with people. Suffer developers have the experience of working with people in remote teams, and still there's a lot of uncertainty in the air and coming back to that sense of conviction is really important. We're some effective ways you've seen for people to harness that conviction when leading a team will mean two things I would just say run is that you have to be very honest with yourself I, think? Think the narrative and merchandising progress to your team merchandising your. Commissioner Team are important attributes. Things that a leader should do. However you can't do so at the expense of hard truths, and so the rule of thumb for me. Is that as leaders? We need to be extraordinarily optimistic about the future and do all the things I just mentioned, but also be pragmatic about the present. So for example. I think a meeting should be all right everyone. While like we tried this, and this did not work and now why didn't it work while? Maybe it was the experience Ab we had to go to market. Ron. Maybe you know so and so did not do a good job on the field like let's all own what our role may have been in this not working, unless really pragmatically say. Why are we behind? What tasks are not getting to? Why are we not working fast enough like really we should hammer ourselves over this, but then after that conversation and the next steps to come out of it, then leader needs to end the meeting leaving people with more energy than they had coming into is important to then. Then restate dot conviction, but here's how it looked like, but hey like. Let's take a step back from moment you know we know that x million customers are struggling with why every single day we know that our customer research is telling us that this is in need more than ever before we know the way this market is changing is in our favor. We know that this and this and that agree state a lot of these very optimistic Queens, so people kind of know their North Star like a flag is implanted in full resolution, and also people leave that pragmatic sense of why we're not winning I. Mean I think that is the kind of formula to both. Address, our truce ground us with the president, but also like really outfit us. You know to head in the right direction. I think that's really a great framework, because it matters that you state the conviction at the right place in the right time as part of a process, we've gone through and explored where the weaknesses are, and where performance may have fallen short as well as come up in mid expectations, and then you also in the book go through in fine to areas that you're exploring one is where the product may or may not be aligned with the needs of the customer, and those are expect failures or or shortcomings, and then the other is the implementation areas where engineering may not have carried. Carried out where you may have tried to take on something that was technically not easily solved, so there's a really good distinctions about that and I think that it it goes to the fact that as leader for team. You've got to keep your eyes focused on slowing the long game. What are some things that the leaders who you advise and have worked with learned from? Do to help? Keep themselves were needed in a long dream while also be able to change focus from the long view picture of problems. You'RE GONNA. Solve an address and it'll come back down and say listen. To make this dialogue the screen this interface work by the next build in two weeks. Yeah, well, let's talk about the long game for a minute. Without looks like one entrepreneur that I work with are known for years and Silverman. The the CO founder of. In he came from a family of doctors where you had to actually go to school for seven years and train for another three years in order to even legitimately call yourself. You know practicing doctor in so when he came out of that background into Silicon Valley where the mantra move fast and break things if something could be done in a week or two weeks sprint, something was wrong. He questioned the status quo of that he said Hey. Why can't you -cational bake something over time, but really accentuates technology are changes in industry. When so that is not something? I learned from him in one way he did that. Key every year would have a chapter for his company religiously merchandise give it a name in I, remember one year for Pinterest. It was the year of monetization right where they launch their AD product, and that was the one of the major disproportionate focus with the company. One year it was internationalization like going to pick our first region or to one year it was. was actually four categories of customer that they wanted to really rally around. It was actually a very helpful tool to consolidate all of the energy and focus of his teams, and it was a very different approach with a lot of other so Kabala leaders have we were always running all these different experiments and moon shots. You know in in different groups working on entirely. Communicating with one another, but it was an approach that I really admire I. Think was part of why interest one in their category and building really. Exciting Enduring Public Company. That's so true and so many of the small business leaders can benefit from having an annual theme or Mantra sometimes having that longer view, so it's not just focused on the day to day week to week month to month, or even quarter to quarter, but saying a year from now this is going to be the year of making sure that we monetize making sure that. That we scale to the certain level or dress, particular customer categories that is such a powerful idea that hope that listeners really embrace and spend time to develop their own themes. Are there any techniques or questions or insights that you've gained by listening to Ben? Talk about this with Pinterest that you could share well. I think that it's one thing to break down the. The enrolled aspirations in the chapters and help people know what to focus on, but I think it's also important to really be great merchandiser of that story and the analogy actually like to use personally is you're driving your team? Cross country with the windows blacked out in the backseat. So none of them know where you are the progress that you're making and so if If you, just keep at that not way without telling everyone about the milestones. You're passing the bridges you're on the state. Lines are crossing. People are going to go crazy and they need to feel like they are making progress, and they need to be narrated through this journey, and actually that analogy really holds when you're in a bold project or turnaround her new venture. Small Business, trying to crack something new starting from zero. It's really hard for your team to know that anything is going in the right direction and actually pull some research that was done by Teresa Ave professor at Harvard business school around motivation, and she did this big kind of diary driven research project where they handed out in had large groups of people in big companies do like a diary entry every day where they also measure their kind of level of motivation, the inputs and the outputs and she really found in other studies have also supported this. Is this notion that? That progress begets progress so when people feel like they're making progress. They're likely to be further motivated and are likely to make more progress in, so that actually goes to say that it. Your team is not feeling the progress that they're making their unlikely to continue doing so. What are the tactics for that? Wilkshire you put up completed to do lists or numbers, zero tickets, or another metrics that development teams, design, teams or retail teams mcadoo merchandise metrics to the teams. They're feeling like past is the tailwind for the future. What kinds of things you celebrate? Do you make? Fun Games in short term and of accomplishments along the way keep people focused on the long-term at the ants. We actually had some very fun. Creative ways of doing that such as such as I mean, do funny, little stories, you know one is been a lifelong vegetarian. Maybe for you know thirty of my forty years and my team, it would be fun to make me agree to eat certain types of meat off of certain people's forks at certain types of milestones, and I was like. Whatever sure you know? If we ever have half a million users, and of course L. Chicken off dates for you know what why not and never thought we'd actually get there and I figured if we did well, that would be a luxury problem that us, and in fact when Christmas dinner we finally did get there, and it was just one of those fun things we called them. Them slap bets in the team where we were just again like try to create these fine little milestones to keep us engaged another really interesting and find one was that the name hands is made up and so when we would would type in be Hansen the Google back in two, thousand, six, early, two, thousand, seven, it said. Do you mean enhanced? Enhance so we were a mistake. Was Literally viewed as a mistake by Google, the search engine, and so he said to ourselves. Yes, you know money revenue real user growth real noted notoriety is years and years away. However, let's try to be a legitimate search result in Google within the next three to six months. Let's put enough blog posts and portfolio alling acts malicious really ain't singularly focused on doing this and yellow, like five or or months later we typed in. Google and then it was a legitimate search result, and it was one of those moments who is in the right direction. It was pushing team in the right direction. It was a short term reward that could actually accomplish in a kid you not six months later beyond saying became super popular loss it all over again. But the point is that it's external validation that everyone was able to celebrate, and it also puts the fact that they're external factors. You can't control for rights exactly, but this is these are the types of games is that this is the merchandising efforts I'm referring to that leader must be creative with these are the types of things you don't necessarily think of as part of the job of a leader of a team by. By you are a sales in marketer more than anything else, you're always selling and marketing to investors, employees, perspective employees, but also plays to stay wants their end customers, and you also have to be agnostic as well. That's the other point. You can't just be a promoter in the people. Stop trusting, so there's a balance in. It is in one of the things that reminds me of his early book. You talk about how? are some managers who gets seduced into trying to keep morale up at the expense of hard truths or at the expense of underperformance. And what would you say to a project manager? If you were given the opportunity, he was at a meeting. It was appropriate to to talk to him, or he was on your team, who was seduced by the lure of celebrating fake wins, as a way of boosting morale was already fake wins at the expense of hard truce is probably what has led to a lot of the flameouts that we come to talk about in the media of start ups that set off. Off To do something bowls, and then proved to be disingenuous at or fraud at worst and I think that is the result of leaders failing to just acknowledge you know what the setbacks were, and what things are not working, and and be willing to make difficult decisions accordingly, luck favors decisiveness, and the reason is because when you're decisive, you can learn from your mistakes more quickly. You can get further resolution on the possibilities around you dot, start to connect and people. There's a gravity around indecisiveness and being honest I think that that's actually incredibly important thing in the long term house in by variety of. Reminds me of the book that was written about Elizabeth homes. Are you familiar with her? Yes, well bad blood, and she was an excellent marketer and a merchandiser of her message because I'm not going to call it a truth. But her message and shoes extremely powerful with that, and she also made some really profound mistakes that are easy to identify much closer to win. They're causing problems within teams and companies. What are some things that stand at about her story with Theranos Book that was about a bad blood, which is just a excellent book, what are some of the things that stand out about the way that she was very effective at telling her story, but also creating a horribly corrupt culture? Yeah, I mean, it's I, don't know her personally, and I was never involved with the company, but I'll tell you that I did see her speak ones at a Ted conference, so sort of like a Ted conference focus in the medical community that I'd gone to and he the one thing that threw me off was. there. Were you know? Watch someone, speak, and then there's a crescendo at the end like a moment where they say and this is why this is what we're. GonNa do in the world. This is the future whatever event if if it if it comes once at the end of talk from speaker that has really worked with a lot of facts in a lot of. More pragmatic can down to earth arguments than maybe you know it's. It doesn't come across as trite winning. Destruct me when I saw speak, which is how many of those moments were throughout? It sort of threw me off. I was like. Why is there so many these big picture? Promise moments at amid confrence. Especially where you'd think it's more about like the clinical trials say this is what it looks like. This is the data, and so I just wonder if again mode over indexing on that side of it I think that can be a real liability, and so it's are you promoting? Are you trying to make something look better than it is? That should be a real kind of warning. Sign that you're on a dangerous track, so if a project participant is listening to a project manager, who's overselling the progress that they're making either internally or externally? One of the things that they ought to do is say we need to talk about where we're falling short or missing her milestones, because we need additional resources or additional clarification or or external feedback, and to actually ask for those things had been a situation where you've empowered or surprised by employees. Asking for things that you thought didn't need to be covered. I'm not sure about that well I. I mean there's many many instances where as a leader I find that the role is kind of peel back all the corporate euphemisms and Lingo, and and really have some impatience for kind of bold statements and really get down to the granularity of what someone's actually saying and also make sure you have a culture where it's okay to say I don't know actually that didn't work as well as. As you're saying here's why I. How do you make sure that people feel comfortable doing that? You have to celebrate it. You have to say Oh. Thank you for when he met. Our listened like I'm glad you made that feedback after a conversation. I'm glad I'm glad you brought us down to earth and their. You're I'm glad you shared both the good and the bad data that really helped. Helped us make a better decision. I think those are the types of little training moments that you have to do a team. They seem obvious, but if you're trying to keep a team together despite all of the failure is your enduring in the lack of any late of the end of the tunnel. It's actually harder to do that sometimes because you want to feel you always be the cheerleader. Got Again. Can we do it? Angels Place. It's difficult also I think where there's managers who responsible for carrying out a decision that isn't entirely embraced by the team. I'm thinking of the story told in the book when you're at Adobe and you're making that huge shift from a software product in a box to subscription model, and it was difficult to have those conversations because it wasn't that level of clarity when you reflect back on that. That, what's one or two lessons that you learned from managing that process or be involved in a process? Sure a couple thoughts, their first of all alignment is everything in organization when you're leading change when when you, when everyone is fully aligned the speed at which you can move and the amount of trust, you can have anyone having any meeting in making any decision without you. You know that is what unlocks the potential of organization. When you don't have alignment, there are two ways of dealing with it well. I have to know that there's a lack of alignment and I like to say that everyone should be a whistle blower of lack of alignment. If you go into any meeting and you attack that people are not aligned with the strategy. You have to speak up like that's how you make your organization healthy. When people are out of alignment, there's two ways of dealing with it. One is to do the work to show something that no one can argue with you. Know an I love to use prototypes into me prototypes over thousand meetings. You have a really well baked customer journey. That, no one can argue it just so obvious and logical. This is a superior experience for customers that gets people align like a hot knife through the butter of bureaucracy. It's really powerful thing, and that's why I empowered designers in the product process in why always make sure designers are in the meetings or were discussing strategy? If you can't do that or comment that the other way of solving alignment or misalignment rather is to throw process at the problem in process slows down, but it is sometimes necessary when you have more people across more regions with more interests in different expertise, and you have to get them aligned soon as you just need to throw more process into the knicks were check in meetings more approvals and you know I. Try to do so sparingly because I think it's an easy solve, and I think it actually grows accumulates into what I like to call organizational debt. Debt. These processes were still going through because of the fact, they were thrown into the next two years ago, but are now the equivalent of craft. Also you have to kill processes as much as you create them, but anyways I digress, that's how we tackle alignment in an organization, perhaps only introduce those bureaucracies. Your auto always add an expiration date. Fine will go through this and the next two or three months, and then we'll review to see whether it should be sunset or renewed. Yeah Scott Are you ready for the my quest for the best way round sure. So early I asked about a person who inspired. You're growing up. What's a song that inspired you as a teenager? I was actually released by lantis recites tire album jagged upset when I was a teenager, I, remember in my early years of high school when that was all the rage, just dislike person who was a kind of pop star before she was on Disney channel whatever and then suddenly. Unleashes this soulful raw album that just catches everybody off guard in this profound way like to me. That was just like such a great statement on creativity motion. And I remember being really taken aback by it. I actually. Had silicones a lot of fun. If you could put a slogan about your work on a billboard that every executive and creative project team leader head to view each morning, what would it say well? You know what I would hope. It would be one of those digital billboards where I could change it based on what we were. Where we are in our in our mind that day, but It would probably be that. A Labor of love always pays off just not as we'd expect I. There is something to be said for knowing that. If you love what you're doing, your skills combined with your interests and your initiatives, you'll always land integrate. Place is just yet to be open to some surprises Lunghua. And having written the messy middle. What's the most important lesson idea or practice? You personally find valuable on a day-to-day basis these days well, there are a number. I think one thing I'd be whispered to myself in times where I'm forced to make difficult decisions. And you know in these days with the trading of resources in the covid crisis in having to really hunker down as a product organization that can't just invest as much as it typically wed one of the things that I you have to make decisions. Tell people those decisions into winky ball and. There's a part of the book where I say. There's this thing that I would wish her myself when I was going through very difficult times, hands and other entrepreneurs said similar things they would say to themselves which is do your job, and I'll spare everyone the Georgia. Someone's. You have to whisper to yourself to get up and just do it on. You know you need to. Do you know that until you do it? Everyone is looking at you as a bottleneck, and you just have to get up and do it and and that's something you have to whisper to yourself. Sometimes, that's really important. Especially given the fact that we don't have the normal cues that help keep us accountable on track with the a promises with made. Scott what's the best hundred dollar purchase you've made in the last three months? Oh, that's easy. I have awkwardly shaped in her ears. Apparently because I air pods have never really truly fit them, and I'm really into running these days. It's just always been very annoying. Finally found a tariff silicon. Airport adopters that actually make me use I para airplanes when I run without any fallout. Godsend. Is a great one. Little things can make such a difference, right. And what's the most important habit routine or That you've stopped in the last year. That's the most pleasure or personal satisfaction that I've stopped or started. Sorry well. Everyone thinks that things that they could start and often have a never ending list of things that we want to do to improve, but sometimes we improved by stopping things that are no longer appropriate. What's something that you've looked at reviewed and said you know what this doesn't fit anymore. I I like any normal human being eating. Every day or my whole life, the nights I this new intermittent fast regime and my allergies went away in a lot of things. Improved in my health, so I would say that I stopped. Eating before noon. That is fascinating. Scott I just want to thank you so much for contributing to quest for the best today you've. You've shared so many great ideas around the messy middle about your experiences and learning from your father who was an orthopedic surgeon, and how we need to adopt in stay true to some of the values we learn, and what you learned from him was the work. Work Ethic and being able to really care and have that empathy for in his case patients in your case customers and Co, workers and colleagues, the short term reward systems are so powerful. That's critical for us to embrace them rather than try to manage without them or to learn them. Just come out at through through thrown of Lucien but to steer them. WanNa be sure that when we working with teams that we aspire for positive slope with that feedback, because it's really important to look at it at the brand new level. And asking people, you know what appeared basis given all that you've learned in the intermittent process Jim more or less conviction at the end and being ridler time some of the difficult feedback, you have for a team to make sure that they leave with more energy at the end of the meeting, rather than trying to insert the positive news and convey the message as important as it is at the wrong time services best to leave people at the end of the meeting after you've gone through all the ways that they've had shortfalls. And for these in so many got WANNA. Thank you so much for joining me on my quest for the best today pleasure. Scott! Out More you and your work. Yeah, and I'm easy to find so at Scott Belsky on twitter or instagram I tried to accessible in in. We love to answer any questions in certainly try to share the latest. Things that I find interesting on those channels Scott, both also of the messy middle. Thank you once again for joining me on my quest for the best. Thank you bill. Hi, this is bill and I. Hope you've enjoyed this podcast interview. On my question, the best be sure to subscribe on Apple podcast Google play stitcher or your favorite up. So you never miss an episode. Full of stories tips insights for the ambitious small business leader now I have a quick request for you. Please go to apple podcasts and I tunes and give us a rating and review. My team and I really appreciate the feedback and we read every comment. Find out what you enjoy and what you want as we develop new content, course materials and a few surprises that we have in store for you when you rate and review my quest for the best you help other small business leaders find US subscribe to the podcast and join the community. You can get the insiders newsletter for small business leaders by. 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