Chris Grouchy:

Hey everyone. Welcome back to another episode of the Legends of Retail podcast, brought to you by Convictional. We talk to leaders in retail and in eCommerce so you can learn from them about retail strategy, leadership and team management, and take their insights back to your company. I'm your host, Chris Grouchy, Co-founder and President of Convictional, the supplier enablement platform that helps retailers onboard drop ship vendors in minutes, so they can curate product assortments faster. We're doing something a little bit different in this week's Legends of Retail podcast. We recently hosted a small in-person dinner with retail and eCommerce leaders in New York City, retail leaders from companies like Nike, Estee Lauder, and Condé Nast joined us to discuss all things commerce. During that event, I had the opportunity to host a Q&A with a close advisor of mine, Scott Belsky. Scott Belsky is the Chief Product Officer at Adobe and Executive Vice President at Creative Cloud.

‍

He's an executive, entrepreneur, author, investor, and all around product-obsessive. He co-founded Behance in 2006 and joined Adobe after they acquired Behance in 2012. He's an early investor in companies like Warby Parker, Outdoor Voices, Flexport, Pinterest, Uber, and of course Convictional. During our live conversation, Scott shared his wisdom around how leaders should merchandise progress in their teams, how they can hack short-term reward systems to motivate progress. All right. Here's my conversation with Scott Belsky, Chief Product Officer at Adobe, live from New York City.

‍

Every quarter our leadership team at Convictional gets together and we do a lot of planning. We look back on the previous quarter and look ahead, and we talk about product, we talk about market and culture. And as a remote team, we find these moments together to be pretty magical. And so, when we started planning this week's leadership meeting in New York City, a bunch of us are from Canada, some of us are from different parts of the United States, we thought, "Oh, it'd be so cool to get our customers in a room together and just jam over dinner and good wine and good cocktails."

‍

And then we had an idea, "Well, why stop there? Why not invite investors and partners and other retail leaders to be able to hear the story and share ideas with one another?" And so, the challenge was we had three weeks to make it happen, and the team pulled it off. So huge shout out to them. Also, as part of that three week planning process, I asked Scott to come do a little Q&A on his entrepreneurial pursuit and his journey, and Scott graciously agreed to come have a chat. And so we'll get into that. So for those of you who don't know Scott, Scott is an executive, entrepreneur, author, and investor and all around product-obsessive. He's currently Adobe's Chief Product Officer and Executive Vice President of Creative Cloud.

‍

Scott's passion is to make the creative world more productive, connected, and adaptive to new technologies. He co-founded Behance in 2006 and served as CEO until Adobe acquired Behance in 2012. Millions of users, a few amazing conferences, so we were just chatting about event planning and how important that is for building communities. He was/is an early advisor and investor in Pinterest, Uber, Sweetgreen, Carta, Cheddar, Flexport, Airtable, Convictional, and we are so lucky to have him, but he's also the best selling author of two books, Making Ideas Happen and The Messy Middle. So give it up for Scott Belsky.

‍

Scott Belsky:

Thank you.

‍

Chris Grouchy:

All right. So let's jump into it. I read Making Ideas Happen when I was at Shopify in 2016, and Messy Middle shortly thereafter, when Roger and I started Convictional. And at the time, we were riding that high of a new idea and then of course that fades, and then you get into the wiggles of false hope. One sort of theme across both is this idea of self leadership. And in The Messy Middle, you quote Angela Duckworth of Grit. She says that the people with the most grit tend to be highly metacognitive. These are people who are aware of their own tendencies, they're very reflective, they know how to get out of their own way. And so I'm curious from your experience, how did you learn to develop self-leadership? What are some kind of formative experiences that you had, whether it was building Behance or at Adobe, where you've had to learn how to cultivate this quality of self-leadership?

‍

Scott Belsky:

Yeah, well first of all, I mean thanks again for having me.

‍

Chris Grouchy:

Yeah.

‍

Scott Belsky:

It's really amazing when a company actually creates a community that in some ways transcends the company. And just the nature of conversation and the fact that it was even hard to get people to sit down is a good sign. On the topic of this notion of knowing your strengths and weaknesses, I mean, I always like to say self-awareness is probably the competitive advantage in any career. And it's easy to say, but it's hard to actually conjure up at moments when you feel defensive, when you feel worried, and act out of insecurity, when you act out of fear. I've always been fascinated by how many companies just move on from anything that they do, whether it succeeds or fails, and just kind of moves on to the next thing. We also have a tendency to not fix something that's working.

‍

We only tend to fix things that are broken because our time is limited every day. And yet, we also know that every great product succeeds because they kept iterating and making it better and better and better. Yet why don't we do that for the way that we work? If you have a meeting every Tuesday morning just because it's Tuesday, and it seems to be working for your team, maybe you'll never touch it. But why don't you make it every other Tuesday and see if it actually is just as good, if not better for the team? And if not, revert to the previous version. So this obsession with optimization is something that I observed in... And writing The Messy Middle, I talked to a lot of teams that I felt were outperforming, especially through difficult periods, which is a nice time I guess to have this conversation for us because we're probably entering one. As you called it, the hopeless swiggles or whatever.

‍

I like that term. But I think that it comes down to a culture of a learning organization. Do you have an obsession with debriefing things? Whether they go right or wrong. Do you actually go around the table and say, "Okay, why didn't this meet our expectations?" Or, "What went wrong?" Let's really boil our brains to figure this out as opposed to just kind of move on to the next thing. Which is, by the way, super, super seductive, because quarter by quarter, it's always facing forward, always moving forward. It's just the natural tendency that we have, I feel. But the leaders that I admire most are ones who actually force that postmortem and really are always trying to build the culture of a learning organization where you're constantly figuring out what went wrong.

‍

Chris Grouchy:

That's a great segue into my next question, which is all about merchandising progress. I've already used this phrase, I've started saying it, I think it's incredible. And folks in this room are experts at merchandising products but may not know how to merchandise progress. At Convictional, Roger, my co-founder, came up with this segment that we use during Townhall called The Weather Report, and we talk about the rain and the sunshine. The rain's all the shit that's just going bad, right? Just laying it on the team. And then we also talk about the sunshine, some wins, right? Can you say more about what it means to merchandise progress inside of an organization, large or small?

‍

Scott Belsky:

A couple thoughts on this. So when I went to... At business school, I took my second year and I worked under a professor named Teresa Amabile at Harvard Business School, focusing on creativity in business. So she basically did a lot of the research around creativity motivation within the big enterprise. And a lot of her research stemmed on these journals that people kept, and would report back in terms of what they were doing and whether they felt like they were making progress and whether they felt motivated, and then what ended up happening in a longitudinal study. And to save you all the time, basically the TL;DR on this is progress begets progress. When we feel like we're making progress, we make more progress. When we don't feel like we're making progress, we stop making progress. So there's a bit of a chicken in the egg thing going on here. Which is why I think it's important in your weather report to say this is what's wrong, but also this is what's working, because that's what we feed off of.

‍

I mean, we need to know both, but we definitely need to know both, right? Any sort of bold journey or entrepreneurial venture, I always describe as driving a team cross-country with the windows blacked out in the back seat. And they're all sitting in the back seat and everyone's going stir crazy. They have no idea where they are, when they'll get there, why they're sitting still. But if you narrate the journey to them, "Oh, we're just crossing the bridge." Or, "We're now in a little traffic, but I see it opening up." If you narrate the journey, it becomes a lot more tolerable for the people that you're carrying along with you. That narration to me is the merchandising piece and the progress begets progress is the necessity for that. Now, let's talk about the advertising industry. This is a fascinating $100 billion plus industry annually that simply creates compelling ways for us to take action.

‍

Billboards, ads, whatever the case may be, all the ways you sell your inventory, these are just tricks to get people to feel moved and to take action on something. To know that something exists and to feel compelled to do something about it. And it's fascinating to me how we use those tools and amazing design and art and cleverness and creativity to get people to take action when it comes to buying stuff. But what about taking action at work? What about understanding the progress that you're making or the problems that need to be addressed? I remember when I was starting Behance back in 2006, really close by actually on 17th between 5th and 6th was our first office, I didn't know what I was doing. And we had two engineers on the team, one designer, me kind of overseeing product in the company, we had a big sort of easel board where we would put the big check boxes of things that needed to be done.

‍

So all the bugs and stuff like that that we'd found before people use software for that stuff was all written down on these big post-it sticky note things that we use on easels. And when we would check those boxes, it was very gratifying, right? It was over making progress. And at first, I was throwing those sheets away when they were all checked. And then I realized, wait a second, instead of throwing them away, let's throw them all up on a wall and let's call it the done wall. And so we just kept throwing more and more and more of what was done and it became kind of absurd, but it became this decoration of progress. And it was one of the most motivating things for us through 2008, 2009, was a very difficult time for our team and for the economy, because we just felt like we were making progress every day. The done wall kept changing, and I think we need to do that for our teams in creative ways.

‍

Chris Grouchy:

The done wall. Love that. And underrated competitive advantage in business is just surviving long enough to figure it out. And you talk about how Jeff Bezos, the 1997 letter that gets attached to every earnings call report, constantly comes back to building for the long-term. Very easy to say we're long-term thinking, much harder to do. My question is actually about the possibility of burnout in the pursuit of a long-term mission. How do folks avoid burning out through the difficult phase of a project or venture in pursuing that long-term mission? Has that been something that you've experienced in the past?

‍

Scott Belsky:

Yeah. Well, first of all, I would say that if the personal career success thing is around self-awareness, the competitive advantage for a team is simply sticking together long enough to figure it out. And I think that's particularly hard these days where, when every headline makes us feel like some other brand or some other cool company is making more progress than we are, and people are constantly fleeting and the average tenure of folks, at least in Silicon Valley in the technology world, is going down. People just rotate much more quickly, which is the antithesis of what I think works best, which is a team kind of building that sense of communicating without speaking, finishing their own sentences, having gone through tough times together so we can use that muscle memory to endure the next round of tough times. It's sad, but the question is how do you defy that cycle?

‍

How do you keep people together long enough? How do you endure the lows? And the true journey of making anything happen is extraordinarily volatile. It has highs and lows. You have to endure the lows, and we'll talk about that. You have to optimize the hell out of anything that works, and then hopefully you have a positive slope, and you just keep going up and to the right, with volatility. That's probably par for the course. That's the best it can possibly be. On the indoor side, we have to hack our short-term reward systems. I mean, that's what I would ultimately say. We are all born with a very heavy short-term reward system for survival purposes. So we look for the gratification of our parents and then teachers and then bosses. Another Union Square reference is Union Square Ventures, the famous VC Fred Wilson, who at one of our conferences said to everyone, "The two greatest addictions in life are heroin and a weekly salary."

‍

And I was like, "Okay." But he was basically making the point that you have to unplug yourself from this short-term reward system that we're governed by in order to do something amazing over the long-term. I don't think that just having a long-term goal or objective is enough. It's enough to get someone to join your team or to maybe inspire you to quit your job and start something or whatever, to take a career risk, but I don't think it's enough on a day to day basis, week by week, month by month, ups and downs, it's just not enough to keep us engaged. So what does? How do you hack the short-term reward system? I think it's about, part of it is culture, people loving working together. I think part of it is also making synthetic sort of milestones that are directional. So two examples real quickly.

‍

Number one is I'm a vegetarian, and my team back in 2006 basically made me sign something that said, "When we crossed 100,000 members on Behance, I would eat meat." And I was like, "Whatever. If that happens, no problem. I'll cross that bridge." And lo and behold, two years later, something like that, at a Christmas dinner, I had to eat a piece of chicken off of our first engineer's fork. And that was a moment for the team for some reason. It shows you we had a real healthy relationship. Another one was when we started Behance, we typed in Behance into Google and it always said, "Do you mean enhance? Do you mean enhance? Do you mean enhance?" We were always a mistake in the world's eyes as opposed, according to Google, right? And so we were so freaking determined to defy Google's algorithm by having enough blog posts, enough link backs from people's portfolios, etc.

‍

And then I think it was late 2007, someone came in and sort of typed in Behance just to try it again. And lo and behold, we were actually no longer a mistake. And then early 2008, Beyonce became super popular. We lost it all over again. True story, but these are the types of things that we did, right? These were milestones, in number of members, number of this, number of that, because we weren't making any money, no one knew what we were doing. We were working in its complete anonymity, ambiguity and uncertainty. And so I think that as all of us kind of bring our teams together, reminding them sticking together long enough is a competitive advantage. That's something that no one else will be able to do, so let's be the team that does that, number one. And number two, obviously culture. Number three, bring some of these milestones and rewards that you think are directional and orient ourselves around them and merchandise the hell out of them.

‍

Chris Grouchy:

I love the we embrace being a mistake and we actively want to change that mindset from the early days. I mean, people still think Convictional is a service to hang out with prisoners or something, like convicts. So I mean, totally hits home. When you sold Behance, you'd been working on it for many years, to Adobe, it was a great outcome. But were there moments of, "Oh shit, what now?" How did that impact your identity because your identity was so, I would imagine, caught up in being an entrepreneur, a founder, a CEO, and then this baby of yours is now part of a much larger organization and it's lots of other people's baby now. I'm curious about this because on the surface it's incredible, but I'm sure that, or perhaps maybe it was actually a little traumatic. Can you say more about that?

‍

Scott Belsky:

Yeah. I think it was. I think that some different members of the team dealt with it in different ways. But yes, some of us commit ourselves to something for 10 years and then it sort defines, it becomes part of our identity. And in that... And feeling like you suddenly don't have, technically don't have control over something, that is so much a part of you is hard. And I also saw some strange things in my team in the final mile of this journey. People do crazy things. There's some self-sabotage because some people don't think they deserve it. There's the same sort of things you see before you do a product launch where there's all of a sudden this big amount of churn. Suddenly people are questioning everything and it's like, "Okay, this is the psychological stuff that's going on and let's orient ourselves on what's really happening." So there was some of that for sure.

‍

But at the same time, we always wanted it to be bigger than us, and we felt like there was no better way to achieve that than have a company that's just going to be around for a very long time that makes all these incredible tools integrate Behance fully into the entire system. I think when we sold, we were a little over a million members, now it's 32 million members. So I think that Adobe certainly helped us bring Behance to a far broader amount of the creative world.

‍

Chris Grouchy:

Amazing. Thank you so much, Scott, for taking the time. Really appreciate that. This is incredible. Thanks man, appreciate it. All right.

‍

Thanks again to Scott for taking the time to come to our event and speak with our community of retail leaders. And thank you for listening to the Legends of Retail podcast. If you want to get notified about future episodes of the show, subscribe on Apple Podcasts, Spotify, or wherever you listen to your podcasts. You can also stay updated by following Convictional on LinkedIn and on Twitter. If you've been enjoying the show so far, please consider rating and reviewing the show on Apple Podcasts or Spotify. It really helps us get the show in front of more listeners. Finally, we're currently developing season two of the show, and so if you'd like to be involved in any way, please reach out to me on Twitter or on LinkedIn, or you can just send me an email. I'm at chris@convictional.com. Thanks again for listening.