May 18, 2023

Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance)

Brought to you by Braintrust—For when you needed talent, yesterday | Eppo—Run reliable, impactful experiments | Rows—The spreadsheet where data comes to life

Scott Belsky is an entrepreneur, author, investor, and currently Adobe’s Chief Strategy Officer and EVP of Design and Emerging Products. He founded Behance, an online platform for creative professionals to showcase and discover work, and served as CEO until its acquisition by Adobe. Scott is an early advisor and investor in several businesses at the intersection of technology and design, including Pinterest, Uber, Warby Parker, Airtable, and Flexport. He is also the author of two nationally bestselling books and founded 99U, a publication and conference focused on productivity in the creative world. In today’s episode, we discuss:

• How to strengthen your product sense

• Why you should only do half the things you want

• What it takes to build a successful consumer product

• Why you are probably underinvesting in onboarding

• The future of AI and how to prepare for it

• Advice for founders and PMs who are feeling stuck

• Why resourcefulness will take you further than resources

• Adobe’s current priorities and their exciting path ahead

Where to find Scott Belsky:

• Twitter:

• LinkedIn:

• Blog:

• Website:

Where to find Lenny:

• Newsletter:

• Twitter:

• LinkedIn:

In this episode, we cover:

(00:00) Scott’s background

(04:50) Why Scott shifted roles at Adobe

(08:29) Advice for PMs looking to build product sense

(10:43) The first mile

(13:18) How to develop more empathy

(16:33) How to build consumer products that work

(20:42) Scott’s philosophy that you should “only do half the things you want to do”

(26:15) Scott’s optimism about how the world will look in five years with AI

(29:44) How AI will impact product teams

(32:55) How the PM role will change as a result of AI

(35:09) How Adobe is leveraging AI tools

(36:59) What the term “golden gut” means

(38:15) Advice for PMs to stay ahead of the new AI trends

(41:02) How to start writing more

(41:49) The messy middle

(47:03) What Scott looks for as an angel investor 

(50:16) Why resourcefulness will take you further than resources 

(52:41) Adobe’s current priorities and the path ahead

(54:58) Lightning round 


• Adobe:

• Behance:

• Casey Winters on Lenny’s Podcast:

• Crafting The First Mile Of Product:

• Shishir Mehrotra on Lenny’s Podcast:

• Scott’s tweet on only doing half the things you want to do:

• Matt Mochary on Lenny’s Podcast:

• Adobe Firefly:

• Howie Liu (CEO at Airtable):

• ChatGPT:

The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture by Scott Belsky:

• Adobe Express:

Build: An Unorthodox Guide to Making Things Worth Making by Tony Fadell:

Cosmos: A Spacetime Odyssey on Netflix:

• Vinod Khosla’s prediction:

• Queue:

• Tome:

• Kevin Kelly on The Tim Ferriss Show:

Production and marketing by For inquiries about sponsoring the podcast, email

Lenny may be an investor in the companies discussed.

Get full access to Lenny's Newsletter at


Scott Belsky (00:00:00):

Yeah. I've had this conversation quite a few times over the years with founders and friends who were running a company going sideways or worse and have had this question, "Should I continue or not?" I always have the same answer. I basically say, "How much conviction do you have in the solution you're building?" I know in the beginning, before you knew all you know now, you had tons of conviction. That's what caused you to leave your job. Now knowing all you know, do you have more or less conviction in the problem and the solution you're building?


And I'll tell you, I get different answers. Some people are like, "Oh, Scott, I mean, I have more conviction. All that I've learned, all the validation I've received from customers, we just haven't figured it out yet. It's driving me crazy. We've tried three times, and it's still like each product fails. But I have more conviction than ever before." And for those people, I'm like, "You know what? You're just in the messy middle. Stick with it. This is par for the course." But oftentimes, I'll hear, "Honestly, if I knew then what I know now, I would not have done this. Holy shit."


I'm like, "Then, quit. Your life is short. You have a great team. Pivot. Do something completely different." If you've lost conviction, you should not be doing what you're doing in the world of entrepreneurship.

Lenny (00:01:15):

Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hard one experiences building and growing today's most successful products. Today, my guest is Scott Belsky. Scott is an absolute product legend. He's a former founder, starting a company called Behance that he sold to Adobe where he worked up the ranks to chief product officer, and more recently, to chief strategy officer and executive vice president of design and emerging products. He's also an author of the beloved book, The Messy Middle. He's also an angel investor in companies like Pinterest, Uber, Airtable, Flexport, Warby Parker, and many more.


In our wide-ranging conversation, Scott shares his advice on how to build product sense, why you should only build half the features that you want, what it takes to build a successful consumer product. And we spend a lot of time on how AI is likely to change the world of product and the world broadly. Scott is such an insightful and articulate thinker, and I learned a lot from this conversation. With that, I bring you Scott Belsky after a short word from our sponsors.


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Scott Belsky (00:04:52):

Hey, Lenny. And it's great to be here.

Lenny (00:04:55):

I don't know if you know this, but it's been a big goal of mine to get you on this podcast since the day I launched it. And so, I'm really excited that you're here. I wanted to start with your role at Adobe. So for the longest time, you're a chief product officer at Adobe. And then recently, I noticed you shifted to this very complicated sounding role. I'm curious what this new role is and then why you made that shift.

Scott Belsky (00:05:18):

Well, in this new role, I'm overseeing strategy and corporate development, all of design across the company and emerging products for the business. If you look back at the last five years or so, it really has been about getting our core products to the cloud, making them collaborative, making some critical and interesting opportunistic acquisitions over the years, ensuring that we have connectivity between the products that we launched, new web apps that meet new types of creatives.


And that was a incredible five-year-old chapter. Now with the advent of AI and new and emerging fast-growing businesses we have like the 3D and immersive space, the stock business and how that whole space is being changed by new technology, the idea of bringing that into an organization and being able to focus on that full-time was really exciting to me.

Lenny (00:06:13):

So what is it that you're doing day-to-day now, just even get it even more concrete? I'm curious what your days are looking like.

Scott Belsky (00:06:19):

Well, I think that it's the strategy of a company always needs to be iterated. And so being tasked with developing the strategy across the entire company, there's no shortage of opportunities and people to meet and things to think about there. Corporate development, certainly like new M&A stuff and integration, all that sort of stuff falls under me as well. And I have a lot of feelings about that having been an entrepreneur that went through integration myself. So it's kind of fun to be on the other side and try to improve it from that vantage point.


On the design side, I spend a ton of time reviewing the design across every product and really trying to raise the bar for the experiences we're shipping. And that's a hard thing to do in a company that has a lot of legacy products and a lot of baggage that comes with them. And on the emerging products side, it's really about the new products we're bringing into the market and how to make them win.

Lenny (00:07:12):

Something that comes up on this podcast a number of times is how CPOs rarely last at a company. They stay. Like Casey mentioned this and a few other people, they stay around for a couple years, and the best they can do is just take a few swings at how things work, improve a few things and then, the CEO's like, "No, this isn't great," and then find someone else. What do you think has contributed to you surviving and lasting and thriving and taking on more and more responsibility at Adobe?

Scott Belsky (00:07:38):

Well, in the chief product officer role, I oversaw design, product, and engineering. And I think part of the reason I was even interested in coming into the company and taking this role is that I felt like these boundaries between these functions are at best artificial, at worst really constraining. And I always have felt like a lot of products win not because of the technology but the user's experience of the technology.


And so, if you have an aligned team that gets that and makes decisions accordingly, I think you can ship better experiences. So a lot of the work I had to do was breaking some of these boundaries down over the years. And I think that a lot of chief product officer roles traditionally don't oversee engineering and sometimes don't even oversee design. And for me, that wouldn't be interesting.

Lenny (00:08:29):

Zooming into product, if there's a Mount Rushmore of insightful product thinkers, I feel like you'd be on it. And part of the reason is that you have this incredible product sense, whatever that means. It's clear that you have strong product sense. And PMs often talk about the importance of product sense and how to build product sense. And I'm curious, how do you feel like you built your product sense. And what advice would you give to younger PMs looking to build product sense?

Scott Belsky (00:08:56):

First of all, I think the biggest mistakes that teams make is they become very passionate about a solution to a problem they're trying to solve as opposed to do everything they can to develop empathy for the customer that's suffering the problem. And oftentimes, the empathy gives you the solution, whereas the passion you have for whatever you think the solution is might be 30 degrees off with the solution actually is.


And so, this development of empathy is a key part of it. And of course, as I think about the discipline of crafting product experiences, to me, it's all about psychology. It's about understanding the natural human tendencies that people have in their most primal moments. I talk a lot about the first mile experiences that we have across any product we use, whether we're a consumer or an enterprise user. In the first 30 seconds of using a new product, you are lazy, vain, and selfish.


You want to get it done super quickly. You want to look good to your colleagues or to your friends. You want to feel successful very quickly by engaging in this product. You don't want to have to watch a tour or read anything, really endure any learning curve whatsoever.


Of course, if you can get people through the first 30 seconds, you have so much opportunity to build a more lasting relationship with that customer and have them understand your mission and the full potential of your product. But we need to ground ourselves with the fact that that's really hard to do. It's fascinating to me that most teams spend the final mile of their time building the product, considering the first mile of the customer's experience using the product. If you can just get more customers through that top of funnel, you are a world-class product team. Let's anchor ourselves on just doing that, and let's use psychology to do so.

Lenny (00:10:43):

And just to make sure people understand, when you talk about the first mile, essentially that's the onboarding flow maybe to the activation moment.

Scott Belsky (00:10:50):

I think that's right. It's the onboarding flow. It's the initial experience. It's the defaults that you see. It's the orientation of where you are. So many products you actually don't exactly know how you got to where you are and how to get home and where to get help. So I would say it's the onboarding. It's the orientation, and it's the defaults.

Lenny (00:11:10):

You've been a constant and early advocate of investing in that part of the funnel. And it's interesting how often that comes up on this podcast when people think about how do we improve retention, how do we improve growth. Often, the biggest wins from stories that we get on this podcast are in that part of the flow. And so, another data point to spend more time there. And I wanted to ask you, are you finding even at the stage of Adobe, there's still lots of opportunity in the first mile or do you find that it becomes less and less and less, and then it's less important?

Scott Belsky (00:11:41):

The answer is lots of opportunity. The reason is because the customers change. Every new cohort of new customers is different. The new customers you have in the early stages of your product are typically more willing and forgiving customers. And you might nail the onboarding process for them, and then suddenly realize that, "Wait, it's not being as effective anymore."


And the reason is because now you're engaging more of those pragmatist customers, those later stage customers who are initially more skeptical, less forgiving, less willing to deal with your friction. And so, you have to reimagine the onboarding process all over again. I mean when you look at a product like Photoshop, for example, it used to cost hundreds and hundreds of dollars. Now, ow you can get Photoshop for as little as 10 bucks a month. And so of course, the funnel's a lot larger. A Lot more people come in with creative desires without the skills or the tolerance to develop them. And so, that dictates an entire change in the onboarding experience for a product like Photoshop.

Lenny (00:12:38):

It makes me think of something Shishir, the CEO of Coda, shared about how he's like, "I don't really buy this idea of product market fit because you have product market fit with your existing users that love it and know about it, and you always don't have product market fit with the people you want to be used the product." And it's related to what you're talking about. The newest people joining have no idea what you're doing.

Scott Belsky (00:12:57):

I agree with that, and I actually think that the role of AI going forward will be to have applications increasingly meet us where we are. To this day, we've always had to generalize onboarding experiences for the most part for everyone. And I'm really excited about the day when kind of products meet us where we are based on what type of user we are.

Lenny (00:13:17):

I have a billion AI-related questions for you. So I'm going to hold off just-

Scott Belsky (00:13:22):

No problem.

Lenny (00:13:24):

... a bit. And I wanted to double click on the empathy piece. So you talk about how to become better at product sense. Empathy and understanding the user's problems is really important. Do you have any advice for someone that wants to build that? What can they actually do to become more empathetic and build that part of their skillset?

Scott Belsky (00:13:41):

Well, the most humbling moments for me as a product leader have always been shoulder to shoulder to customers. Watching them actually go about their day, not just use my product but go about their day because what you end up getting is context for a lot of data that you're missing.


When customers are using your product, they're using it amidst everything else around them. In the enterprise, it's all their other meetings and other products and pings that they're getting throughout the day. And as a consumer, it's between dealing with their kids or their loved ones or watching Netflix or whatever the case might be.


And in order to really understand where the customer is and where their mentality is, you have to understand the context in which they're using your product. So part of developing empathy is being shoulder to shoulder and just encountering that reality alongside your customer. And that time, it just gives you better intuition. It helps you understand more. And with empathy, we can then better create quote-unquote, "for ourselves" because by developing empathy for others, we're feeling what they're feeling. We can then be the customer. And, of course, we all know some of the best product customers, some of the best products in the world are made when we are the makers are the customer.

Lenny (00:14:51):

It makes me think of Marc Andreessen as this awesome code that I always come back to that everyone's time is already allocated. They don't have time for your product. They're not-

Scott Belsky (00:14:59):

That's right.

Lenny (00:14:59):

How do I find a new app to [inaudible 00:15:01]

Scott Belsky (00:15:01):

And by the way, as a related note, since I know Lenny, you talk to a lot of guests around product-led growth. And sorry, if I'm skipping around here. But-

Lenny (00:15:08):


Scott Belsky (00:15:09):

... I think it's also relevant because everyone's trying to get their products to grow. And the other thing that perplexes me is that product leaders expect people to talk about a product being great. And people don't talk about a product doing exactly what they expected it to do. They talk about a product doing what they didn't expect.


And you look at a product like Tesla. People are not going and talking about how they had a great drive today, but they're talking about the Easter egg they discovered on the dashboard or the cool new feature that they discovered that is associated with Christmas or whatever.


And so, it always is interesting to me. In consumer and even enterprise products maybe especially so, why aren't we optimizing for those things that people wouldn't expect the product to do as a way to get that surprise and delight to talk about it, to develop a relationship with our products? I think that's another piece of the puzzle.

Lenny (00:16:08):

That is really interesting, and reminds me of something I just talked about with Gustav from Spotify whose episode might come out before this or after this about how every great consumer product pulls some kind of magic trick and feels like magic to you, like Spotify as an example. And-

Scott Belsky (00:16:23):

I like that, magic, sort of a little mystery, a little intrigue, a little surprise. It's a classic trick that Hollywood uses all the time. Why don't we use it in our own products?

Lenny (00:16:34):

So let me pull on that thread a little bit about just consumer products in general. You spent a lot of your career, maybe most of your career in consumer, imagine Adobe. There's a lot of B2B elements now as well. And you also angel invest and you help a lot of consumer companies. And tell me if you agree, but it feels like new consumer products basically never work.


And if they do work, there's a period where they work, be real, is going through this now clubhouse. Paparazzi went through this. And then, they fail or fade away. Maybe, they come back and then fade away again. I guess, first of all, do you generally agree that consumer is just so rarely successful in consumer products?

Scott Belsky (00:17:14):

Uber was a consumer product, but it built a network effect that was never there before. It leveraged excess capacity that was always there, but never tapped. It did something under the hood that gave it lasting power. I think of Pinterest, and I was Ben's first seed angel and product advisor.


And with that product, he had this unique insight into the consumer psychology where it was not as much about getting likes and portraying yourself through pictures of you and seeing pictures of friends and all of this sort of anxiety that is induced by that, but rather helping people collect and represent themselves with their interests.


And so again, that was kind of a new insight that I also think developed its own network effect that enabled it to be lasting. And there was a fascinating business component which was it drove a crapload of traffic to every source of every pin, which then got those sites to then put pin buttons themselves because they wanted more traffic.


So there were underlying things under the hood again that it's sort of tilting the market in his favor. I think that a lot of these other more recent consumer products are just kind of clever momentary interfaces. And they are in effect at the expense of venture capitalists, R&D for the platforms that already have the network effects and already have the distribution channels and the ad sales and everything else.

[NEW_PARAGRAPH]And so, I think that's why we're seeing B-reels capabilities now also in TikTok, and you're seeing a lot of flashes in the pan, especially in these creative consumer apps, which I've been paying very close attention to. They're fun and novel. But if they really work, those features are then brought into the native Apple camera, for instance.

Lenny (00:19:09):

So let's double click on that. I know this is a big question, but just what have you found is important for a new consumer product to work? You mentioned surprise would be great, network effects, maybe a new insight. What else do you find is important for a durable new consumer product to work?

Scott Belsky (00:19:30):

Yeah. And it's interesting because I think my answer 10 years ago would probably be different than my answer today. I think that there is a nimbleness. And maybe, it started in China with these super apps that were able to do everything. And that changed the idea away from the atomized experiences of a decade plus ago where you wanted a specialized product that did exactly what you wanted in a very reduced way.


I think Snapchat emerged under that world. I think Instagram became valuable to Facebook because of that phenomenon. Fast forward to today where all of us are far more technologically literate and we are able to manage a lot more cognitive load in our everyday technology lifestyles. And so suddenly, we don't mind five tabs. We don't mind features hidden and tucked away in menus because we're sort of used to that now.


And so, maybe that's one of the reasons why these established platforms get away with basically copying any novel new capability as opposed to those becoming apps in and of themselves.

Lenny (00:20:42):

So let me shift a little bit and talk about a tweet that you tweeted about one thing you've learned. You have this amazing thread of just things you have learned over the many years you've been thinking about products and consumer products. And one of them was about how you've learned that, you should do half the things that you want to do, half the features you plan to do, do half the features, offer half the options you want to offer, focus on half the market versus the market you're trying to go after.


Can you just talk about maybe how you came upon that learning and then also just how do you actually do that? It's like, "Sure, great. We're going to do half." But then, which half? And oh, but someone wants this feature so badly, shoot. We can't do them all." So do you have any advice in just how to actually execute that sort of approach?

Scott Belsky (00:21:29):

I mean one of the first comments I'll just make is whenever I'm asked by teams, what features need to be part of their MVP, how do they decide which features they need to ship first and whatever, I always tell them to optimize for the problems they want to have. You want the problem of customers getting through your funnel, feeling successful, using your product and getting value and then saying to you, "Oh, but I need it on this platform, or I need this capability, or I want to be able to share this." I mean you want those problems. So don't do those features now.


Only do the things that prevent people from getting to the point where they care enough to ask you for anything. Make sure they can get through the signup flow. Make sure they can connect their account. Make sure they can use Google login if they need to, or whatever the case may be.


So I always remind the teams, optimize for the problems you want to have, and make sure that you eliminate all the brick walls, the major catastrophe-type things that can happen. But in terms of the half, the half-half, I learned this the hard way.


When Behance was launching back in 2008, I was always trying to hedge us with product features. I wasn't sure if people would be coming to join groups or if people would be coming for the tip exchange where creatives share best practices with one another, or if people were coming to build their portfolios or just share work in progress.


Maybe, it's too much to build a whole project of your work. Maybe, we can allow people just to share snapshots of their work. And so, we actually launched with pretty much all of these features. And then, it was the most complicated form of Behance, was ironically at the beginning.


And then, what we realized is that some things were taking off, and some things weren't. So I remember when we decided to kill the Tip Exchange. And suddenly, the publishing of projects in the portfolio went up. And we're like, "Oh my gosh. Projects being published is the core metric and it's what drives the traffic back to Behance. Let's do this again. I don't know, let's kill groups."


And so, we killed groups. And lo and behold, more people published more projects. And it was like, "Wow." So actually if you make the whole product about one thing, everyone does that. That core crank operates at 10X the velocity and if that's the most important metric for the business, that's gold. And so, we basically went on a killing spree. And we just started killing things. And over the years, we have actually tried to have this sort of, and I pushed this on many products, things I worked with now whenever you're adding things, consider what you can replace. Consider what you can also remove.


When we updated the portfolio on Behance, I remember we used to have this ability to change the colors of your portfolio in Behance. When people clicked on your profile and saw all your projects, you could control that and add your brand element to it.


And so, we know. We were like, "You know what? What would happen if we just took this away? Would people again focus more on projects?" And so, we took it away. For 24 hours, we had people reaching out to us being like, "Damn you. How could you take away these controls for color of portfolio?" After that 24 hours, we basically never heard about it again. All the portfolios look cleaner and more consistent. And people did the core metric more. And so, I just took from that, try to kill things and everything you think you need to do, you probably only need to do half of it.

Lenny (00:24:57):

I wonder if in reality most of the time, you only realize this afterwards versus ahead of time. And that's just the way it is. And then, it's just the seal of sunset, things that aren't actually important.

Scott Belsky (00:25:08):

I do have to say though, Lenny, some of the best product leaders that I've worked with, I do feel like they have this great reductionist or minimalistic tendency by default. They're just very much... They anchor themselves on the one thing they want people to do and do well. And they just are pretty ruthless about everything else, being like, "Okay, but only if we have a problem with doing this core thing. Okay, put on the back burner." And so, it's something I've tried to get better at over the years.

Lenny (00:25:40):

What's really interesting is this is exactly like Matt Mochary who is actually the number one most popular podcast episode talks about when you let people go. And he's helped a lot of CEOs let people go that 100% of the time everything just starts moving faster as soon as you have fewer people. And so, it's the same exact model in people and products.

Scott Belsky (00:26:02):

I think that's right. And that's why I always feel like tough decisions almost always afterwards feel like a relief. And that's true for the product. That's true for people on a team as well.

Lenny (00:26:15):

Let's shift to talking about AI, which I'm really excited about because I know you've been spending a lot of time talking with people about AI, building AI products. You all launched Firefly, which a lot of people are really excited about. You also have this newsletter where you kind of just share your implications on how AI and technology is going to impact the world.


So I have a lot of questions I'm excited to ask you around this. And I'll just start really broad and maybe this is too big of a question, but just how different do you expect the world to be in, say, five years as a result of AI, both for product builders and then just people in general?

Scott Belsky (00:26:51):

Listen, I'm an optimist. And I feel like our human potential has always been held back by the laws of physics essentially. The mundane, repetitive labor you need to do to get anything done is what holds back our ingenuity. It's the friction. It's the work in workflows that wouldn't it be great if we could just have flow and no work?


And I think that that's what AI kind of does, is it gets us from workflow to flow. It gets us into this flow state where any idea in your mind's eye, you can start to develop it. I was having this discussion with Howie who runs Airtable actually just earlier today where we were talking about the leader at IBM who announced that he's not going to hire 8,000 people that he would've hired because AI is going to be able to do that work.


And what we were talking about was, and how he made the point, as engineers have become much more productive over the years, that doesn't mean that companies have wanted fewer engineers. It actually just means that they demand more of their engineers. And engineers have more possibility to do more.


And so, if human ingenuity goes up, maybe we actually want to hire more people because if you have more ingenuity per human being, maybe you can actually do more as a company. And maybe, companies that used to have three products will have five products or seven products or 30 products. And maybe, that's actually the trend that we're forgetting is that humans bring this level of ingenuity to every problem and every opportunity. Whereas computers remember like ChatGPT is basically just giving you what it would look like if, right? It's not truly finding edges that will become the center.


It's actually just mining the center. And it's trying to regurgitate the center, which is also very helpful by the way. So I'm optimistic. I think that there will be far more people engaged in delivering experiences. I'm very long the experience economy because I think that there will be some people liberated to focus more on the non-scalable things that really move the needle for experiences for customers. And then, I also am excited about humans having less grudge work to do.

Lenny (00:29:09):

I'm also excited for that. It reminds me it might have a TikTok account, and I have this team that helps with the TikTok and we haven't shared this, but a few of the TikToks are my voice generated with AI. And they just-

Scott Belsky (00:29:20):


Lenny (00:29:20):

... read script. And it's me reading this story. And it sounds sort of like me. And I showed it to a friend. And I was like, "Do you see anything? You feel weird about this video?" And he is like, "No, you sound great. You sound really a great speaker." I'm like, "Okay. Say hi."

Scott Belsky (00:29:35):

While you were reading, instead of reading a script, you can be plotting the course of the next episode.

Lenny (00:29:40):

Yeah, exactly. So I totally see what you're talking about there. In the product team, which function do you think will be the most disrupted and/or the most, I don't know, optimized through AI?

Scott Belsky (00:29:52):

We're entering the era where we collapse the stack in every organization where instead of having to go to someone for anything, you can kind of do more things yourself. It's very empowering to get the answer from data as opposed to having to go to a data scientist or a data analyst in the middle.


So there's going to be far less game of operator across the organization and far more empowerment for people to dig their own rabbit holes, answer their own questions and get things done.


I happen to believe that that's the advantage typically of small teams, is that they're flat. The stack is collapsed. People all can hear each other in an audible across the room, and that's how they run circles around big stodgy old companies that are dispersed around the world. So maybe, this technology allows cross-functional work and to happen. And I'm excited about that.

Lenny (00:30:51):

That is really interesting. So essentially, what you're saying is a PM will be able to do more design, more engineering, more data potentially. And maybe, one day, it'll be just as good as having a data scientist in your team. But essentially, everyone becomes kind of this unicorn cross-functional mini-team,

Scott Belsky (00:31:08):

Which sort of suggests this idea of meritocracy. It's almost like what if people get promoted an opportunity based on how creative and how much ingenuity they have as opposed to how many reports or bug things they've gone through or whatever else. So there's something about what you're saying that I do think, yes, it's disruptive to the degree that, well, you need a data analyst in the loop. But I also would suggest that again, that data analyst doesn't have to answer redundant requests all day. She can spend time on thinking of other things without the boundaries of functions like we just discussed.

Lenny (00:31:43):

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Scott Belsky (00:33:05):

Well, let me start by saying that I think that the greatest performers I've ever worked with, whether they're designers or product leaders, basically preserve the time to explore lots of possibilities. They call those possibilities down to fewer set. They get feedback on those. They refine them even further.


And then, they present to the team. These are the two or three things I think we should do. And that's the way a great designer works, for example. That is a function of time. If you have the skills and the capabilities, it's just how much time. How much time do you have to explore the full surface area of possibility and find the best possible option.


In my world, in my mind, generative AI and AI for all, when it talks to me about just product leaders exploring possibilities, this should expand the surface area. I was talking to a pretty well known director in Hollywood world, and he was telling me that he uses ChatGPT. I was like, "No. Are you serious? You do?"


And he was like, "Yeah, I don't use it to write any scripts." But sometimes when I'm developing something with a writing partner, I will ask ChatGPT, "What would you do?" And I'll explain the full instance, the full situation in extreme detail. And it will spit out five scenarios. And I actually don't use any of them, but it just gives me more surface area. It tells me the things that I wouldn't want to do, which is also good data. And I just thought that response is so interesting. And so when you ask about product leaders, I think that's what we're going to have, is we're going to have the superpower of exploring far more surface area in far less time.

Lenny (00:34:41):

It reminds me of something I always share about why do you need a PM? Why do you need a designer? Why do you need a researcher? It's not necessarily that they're just very good at these specific skills. It's that they just have time to do this one thing that needs to be done. You can have engineers do the PM role, but they don't have time. They want to code and they'd rather do that. And so, this is really interesting that it connects to. It'll give everyone a little more time to get better at the thing they want to be doing.

Scott Belsky (00:35:08):

That's true.

Lenny (00:35:09):

Is there anything you're doing with PMs at Adobe at this point that help them leverage these tools and just the ways of working that you're actually using today?

Scott Belsky (00:35:18):

One of my obsessions has been bringing design earlier into the process of product development. So it's not necessarily AI yet. But it's the idea of designers, first of all, being in the room, even being in the room with some of the customer research and some of the debates around even the value proposition to the customer and some of the things that traditionally happen only with the PMs. I just find that, again, collapsing the stack, if you will. Having the designer hear these things and contribute gives them a golden gut as they are then sitting down later and going through possible interfaces to solve the problem.


So I love bringing design upstream. In fact, that's probably been the cheat code of my career as a product leader, has just been disproportionately empowering design throughout the process. I think what we're going to start seeing is generative AI augmenting the designer's work in real time.


So right now, I mean in Photoshop, we're experimenting with instead of just reducing an image and cropping, you can also extend an image. And that's, of course, using generative AI for out painting. And so, you can imagine as you're doing edits in that as well as in other forms of design, getting kind of thumbnails of what you might be trying to accomplish and then touching them, almost like predictive text to go to the next step, to the next step, to the next step and take leaps in the creative process as opposed to incremental steps.


I think that that's going to happen far more. And hopefully, product designers, product managers will be involved to some extent in some of these decision points as designers have more options to choose from.

Lenny (00:36:59):

You threw out this term golden gut. What is that about?

Scott Belsky (00:37:02):

The golden gut is when you're designing an experience and a flow. You are playing around with all kinds of options. You're moving things around. You're saying, "Actually, that's too complicated. Maybe I'll separate this one page into three steps as opposed to one page with three steps in a row. How do I break this down? How do I simplify?"


You sometimes have instincts like, "Well wait, what if I just remove this all together? What if you didn't even have this whole series of steps? What if I just had a presumptuous default instead and customers could change it if they think they need to?"


And in some of those sorts of, I wonder if, I wonder if, I wonder if, to me is the difference between a very junior product thinker and a very experienced product thinker? I think experienced product thinkers with that golden gut of, "Oh my gosh. Wait, reduction of cognitive load." Maybe even if 10% of people get confused to get 90% of people far faster through this process is a big win and a great opportunity cost trade off. I think those sorts of little micro-decisions that we make in the process of building products, that's the golden gut.

Lenny (00:38:13):

I love it. I have not heard that term before. For PMs listening and they're like, "Okay, AI's happening. I don't know what to do," what would be your advice for them to stay ahead and be aware of where things are going and not be left behind?

Scott Belsky (00:38:28):

Quite simply in one word, play. We all have to be playing with this technology. We have to find ways. The risk of becoming more experienced in your career is you get stuck in your ways. And you're like, "Ah, no. I don't need to have that automatic draft in my email and get ChatGPT to suggest what I want to respond with. I'm fine without that." Make sure you try it. Make sure you play with it. Write poems for your friends. Try a lot of these various generative AI tools out there just to see what's possible and pursue every curiosity.


The reason I started the Implications newsletters is because I was seeing this high velocity of new stuff every day. And I'm like, "I have to force myself to make sure I understand all of this and think about how these implications will change my business as well as the world that I operate in." And there was no better way to do that than to have to write about it, and promise my readers I'll get a monthly thing out there. So I just think we all have to do some version of that.

Lenny (00:39:33):

Let's plug Implications while we're at it. How do people go subscribe or do they find it?

Scott Belsky (00:39:38):

Yeah. No. It's So it's easy to find, but it's a monthly exercise where throughout the month, I try to capture a few things I think are important. And I really try to go deep down the rabbit hole of what the implications are for various parts of our work and life. And it's been a fun exercise. And also, I get some good polarizing feedback in the process.

Lenny (00:40:02):

Oh you do? Interesting. You should share that. That'd be interesting, is here's what I'm getting in response to the stuff I'm writing. This also touches on a thread that comes up a lot on this podcast, is the power of just writing to help you think through stuff. A lot of people think my newsletters, I'm just sharing all these things I know. I'm just like, "I know it in my head. I'm just going to share it in the thing." But it's more. The writing helps me figure it out and gives me an excuse. And like you said, it's a forcing function to spend the time crystallizing it. And so, that's another reminder for that.

Scott Belsky (00:40:29):

And capturing those things, I think, the thing I've kind of learned over the years with writing and also with product development is sometimes you capture these little glimpses and things or sketches, and they become relevant years later. So don't always capture and write because of a foreseeable need for that content. Consider it almost like a back burner that you're constantly tending to. And imagine that three years from now, the stars will align, and this will become invaluable content or some crucial idea for a problem you're facing at the moment.

Lenny (00:41:03):

There's a lot of people actually in your shoes that want to write more and put content out, but that also have a full-time job with a lot of things on your plate. Any advice for actually getting it done the way you've been getting it done?

Scott Belsky (00:41:15):

Listen, there's no hack to it other than ruthlessness of time and prioritization saying no to most things. This morning, I went for a run and I was like, "I have 40 minutes exactly until I have to get in the shower and I have to be somewhere in 30 minutes from that moment." I'm going to take those 40 minutes or at least 35 of them, and I'm going to write. I don't care if I write five words or five pages. And it's just a great... Without that discipline though, as you said, it's super hard to get it in the seams of the schedule.

Lenny (00:41:49):

Speaking of discipline, you wrote a book called The Messy Middle. And without even talking about what it is, title's pretty... I think people feel like, "I get it." And imagine many people listening are founders or PMs that are feeling like they're in this messy middle. What is one piece of advice for people in this period that you think might help them through the messy middle?

Scott Belsky (00:42:12):

The bottom line is that these years in the middle of whether it's a venture, [inaudible 00:42:19] new startup, old turnaround within a big company, they are messy because they are full of lows. It's very volatile. When you're in those lows, you need to find a way to endure them. You need to endure the anonymity and uncertainty and anxiety.


I'm sure a lot of listeners, whether they're in big companies or starting their own company, it's hard to be doing something that no one knows or cares about. And I always like to remind myself that the life expectancy of humans a hundred plus years ago was 25 years old. So the idea of spending three to five years of your life on something, especially if it might fail, was a bad decision. And I think biologically, we feel the need for constant rewards and affirmation to stick with something long enough.


And in fact, most of your listeners were all building things that take many, many years to defy the odds. And we have to overcome our natural human tendencies in this instance by sticking together long enough to figure it out. So how do you do that?


I mean, obviously, part of it is culture, wanting to serve the customers you serve and working with the team you are working with and that being enough to kind of stick it long enough. I think part of it is short-circuiting the reward system, finding micro goals and milestones that are mutually agreed upon. We're going to celebrate these even though in the greater scheme of things, they don't matter much.


I think that's a key part of keeping the team and keeping the dream alive. I always like to use the analogy of we're driving our teams across country as product leaders with the windows blacked out in the backseat and everyone's sitting in the backseat. And so, if they don't know what we're doing that we're making progress, this traffic is clearing, we just cross state lines. If they don't receive the narrative, they will go stir-crazy. And so there's a lot of research around progress, be getting progress and how progress is a source of motivation. And so as product leaders, we have to merchandise progress. We have to be the steward of this narrative.

Lenny (00:44:19):

And you touched on this a bit as you were just talking, but there's also this moment where it makes sense to quit like you shouldn't stay with things endlessly. And I guess any advice on just when something is like, "Okay, you should probably move on from this." Makes me think a little bit about there's all these companies that just keep going that maybe shouldn't keep going because they have enough money or they're just like, "No, founders never quit." Any advice or thoughts that you share there?

Scott Belsky (00:44:46):

Yeah. I've had this conversation quite a few times over the years with founders and friends who were running a company going sideways or worse and have had this question, "Should I continue or not?" I always have the same answer. I basically say, and I really ask, "How much conviction do you have in the solution you're building?"


I know in the beginning before you knew all know, you had tons of conviction. That's what caused you to leave your job. That's what caused you to take all this risk and hire people and raise money and all this stuff. Now, knowing all you know, do you have more or less conviction in the problem and the solution you're building? And I'll tell you, I get different answers. So some people are like, "Oh, Scott, I mean I have more conviction. All that I've learned, all the validation I've received from customers, we just haven't figured it out yet. It's driving me crazy. We've tried three times, and it's still like each product fails, but I have more conviction than ever before."


And for those people, I'm like, "You know what? You're just in the messy middle. Stick with it. This is par for the course." But oftentimes, I'll hear, "Honestly, if I knew then what I know now, I would not have done this. Holy shit. " I'm like, "Then quit." Your life is short. You have a great team. Pivot. Do something completely different. If you've lost conviction, you should not be doing what you're doing in the world of entrepreneurship.

Lenny (00:46:19):

Sometimes, there are moments of that, I imagine. And so, there's probably some spectrum of just how little conviction and how long you felt that, right?

Scott Belsky (00:46:27):

I think so. But at the same time, listen, we all have ups and downs. We all have good days and bad days. However, I do think that great founders are just... They absolutely know in their core that something needs to exist, and they will just be ruthless and relentless until it does. But if you lose that, I actually don't know if you have the fuel to continue. So listen, you're right. Don't make a bold decision on a bad day. But if the conviction generally dissipates, be open-minded about other options.

Lenny (00:47:03):

You do a lot of angel investing, talked to a lot of founders. What is it that you look for? What do you think is important for a startup to show you for it to feel like a good bet that it'll likely work out? What are some of the important attributes that you look for?

Scott Belsky (00:47:18):

I'll talk for a few things on team and then a few things on product.

Lenny (00:47:21):


Scott Belsky (00:47:22):

On team, I really value founders who listen, who really learn, who long to shake shit up a bit, and also value the mission that they're on more than the money that it yields because I do think that especially during a period of time where you don't have revenue, you're going to need to be motivated by something grander and bolder than revenue.


I also have an allergic reaction to founders that are real promoters who are constantly trying to sugarcoat the truth, who like to gloss over the hard parts. I've always admired leaders that are optimistic about the future but very pragmatic and somewhat pessimistic about the present. So the founders that I have a great sort of chemistry with are people who are like, "This is how big the market is. This is how amazing this is. I know this needs to exist."


But we've got a lot to figure out. There are things that are not working. We don't have these data sets. These are the major obstacles we're struggling with. These are the things that keep me up at night. Those are real people. And you know that in that volatile messy middle that they're going to inevitably go through that their team, their investors are going to have the real truth and they're going to be able to engage and find solutions.


So I really love finding those types of founders, and I'm very wary of the name-dropping overly promoting folks who are unlikely to be able to partner in that way. On the product side, I'm looking for an object model way of thinking about a product that I am confident the will scale and as they solve their problem. And when I say object model, what I mean is it clear whenever you're seeing the product, how it works, where you came from, where you're going?


Those are the three questions I always ask when I'm doing product reviews. It's like, "How did I get here? What do I do now? And what do I do next?" And I feel like every screen and every product experience, you should be able to answer those three questions. Sometimes, I'll be talking to a team that says they're design driven, says that they're building a incredible product, and they'll show me a demo and I'm like, "This is all over the place." There's no clean clear breadcrumbs and object model for how this thing works. How are they ever going to get people through their funnel? Clearly, they don't value this as a core principle, and that's also always a red flag. And then finally, I just obviously have to believe in the problem they're solving. So those are some of the things I think about.

Lenny (00:49:53):

And you focus primarily on consumer or do you invest all over the place? And I'm asking in case people want to reach out and maybe, "Hey Scott, you want to [inaudible 00:49:59]."

Scott Belsky (00:49:58):

Yeah. No. I'm pretty agnostic. I look for product design-oriented teams making things that need to exist. Beyond that, I try not to be too prescriptive.

Lenny (00:50:06):

Okay. Excellent. Any last words of wisdom that you think impact the way people build product in the world that tens of thousands, hundreds of thousands of listeners listening? Is there anything else you want to share before we get to our very exciting lightning round?

Scott Belsky (00:50:20):

Two quick things. One, for the moment that we're in, and then one for why we do what we do. For the moment that we're in, we're in a resource-constrained environment. Let's face it. We're all going to have less money, fewer headcount, all that kind of stuff.


And I've always found that resourcefulness brings you further than resources despite the fact that over the last seven to 10 years, we've basically thrown resources at every problem. Oh my gosh, this is not scaling. Throw more money at servers. Oh my goodness, we need more people on the social media team. Throw more money at headcounts. We've had a resources way of solving our problems as opposed to a, well, let's refactor how we run that database, or let's refactor how that team answers customer service requests. Let's bring a new technology to make it more efficient. Let's leverage and play with AI to see if that can help us.


We are in this era now where we're being forced to be resourceful and to refactor as opposed to hire and throw resources at problems. I think that's a great opportunity. I feel like this is where the best teams are going to build that muscle, that are going to go the distance. That's why all these VCs say it's so cliche that the best companies are always built in errors like these.


So my point number one is capitalize on the crisis, everyone. If resources are carbs, resourcefulness is like muscle. It stays with you. It makes you stronger, and it helps you have a better intuition and better performance over time. And then, I guess taking a step back, I would just encourage folks to recognize that anything amazing in the venture world is ultimately an exception.


And with all of the best practices, Lenny, that you and I just discussed and all the stuff that we read and books and whatever else, I always try to remind myself that at the end of the day, sometimes, exceptions are the rule when it comes to doing something truly transformative and that nothing extraordinary is ever achieved through ordinary means. And so, while we should always take these best practices and, sure, listen to some of the lessons I learned the hard way and whatever else, but at the same time if everyone says you're crazy, you're either crazy or you're really onto something. So take that with a grain of salt.

Lenny (00:52:41):

Love that. Speaking of extraordinary, I thought it'd be cool to just give you a chance to talk about what you're doing at Adobe. What are some of the products that you're working on? What should folks know about potentially what's happening in Adobe they may not be aware of?

Scott Belsky (00:52:53):

Yeah. No. Thanks for asking. For us, I would say there's really three trends that are driving or three waves of transformation, I would say, that are driving the strategy right now for us. One is just that people are becoming more creatively confident. It's kind of wild that we're like most confident as five-year-olds creatively when we're drawing and our parents are like, "Oh my God, that's beautiful. That's amazing. Let's put it on the fridge." And then creative confidence kind of goes down from there for most adults, and that's really sad.


And with generative AI and tools, we have something called the Adobe Express in market, and our generative AI offering is called Firefly. These types of tools make people feel more creatively confident right away. It's pretty amazing to see people that would never pick up a pen and draw or suddenly feeling confident. So I would say that's like wave number one.


Wave number two that we talked about a little earlier is the fact that creative professionals can now explore 10X the surface area of possibility. These tools are making them so much more efficient. And some people are like, "Oh my gosh, creative pros are going to be replaced." No. No, no, no. They're not. They're just going to find 10X better solutions. They're going to have that capability to explore more possibilities. And that's what makes design great, is finding, exploring more surface area.


And then, I would say the third wave that's fascinating to me is personalization. I think we talked about this a little bit, our apps will meet us where we are. I think that every marketing experience will be increasingly personalized for each of us. Every commerce experience, they'll know who we are. They'll just show us our shoe size and no one else's.


These sorts of transformations will really change the entire world of commerce, and content, and media, and everything else. And Adobe has a big digital marketing business that is focused on enabling some of that. So those are factors of strategy that I would say are driving some of the new products we have under development. And now, it's all about let's talk more shit.

Lenny (00:54:50):

I love that. You need a banner of that. It's been amazing to watch Adobe's rise over the last decade. It just felt like it was going nowhere. And all of a sudden, it's a juggernaut. And so, great work, Scott and everyone else involved. But with that, we've reached our very exciting lightning round. I've got six questions for you. We'll try to go through it pretty fast. Sound good?

Scott Belsky (00:54:50):


Lenny (00:55:09):

Okay. Sound excited. Here we go.

Scott Belsky (00:55:12):

Sounds good. Let's do it.

Lenny (00:55:12):

Let's do it. What are two or three books that you've recommended most to other people?

Scott Belsky (00:55:19):

First is Build by Tony Fadell. Tony is just an amazing, charismatic, deeply pragmatic, product builder. He's been brave enough to do both Adams and Bits as he says. And his book is just chock-full of wisdom. I do appreciate some of these kind of laws of nature, laws of power type books. I love psychology books.


I'm trying to think of some offhand that have really struck me. But understanding the natural human tendencies of people, I think the laws of power talks about tons of wars over centuries and what sorts of natural human tendencies or inequalities drove massive rebellions and revolutions. These sorts of insights, believe it or not, parlay into decisions we make in products and making people feel successful and productive. So I don't know. I love those books just because I think that they remind us of the limitations and opportunities or possibilities of humanity.

Lenny (00:56:27):

What is a favorite recent movie or TV show?

Scott Belsky (00:56:29):

What I love is these documentaries about the cosmos and about the edge of our understanding of black holes and what happens out there in space. So I don't remember. I know one is called Cosmos on Netflix. There are a few of them. But in my downtime, I get lost in some series like that.

Lenny (00:56:49):

You have kids, one or more kids.

Scott Belsky (00:56:51):


Lenny (00:56:52):

What are you doing to help them plan for this future?

Scott Belsky (00:56:54):

I think about this all the time. What are our children going to do in a world where if you believe Vinod Khosla's prediction that 80% of the work, of 80% of jobs will be replaced by AI, what will people do? As we talked about their ingenuity will be unleashed, that's great. But ultimately, I always revert back to this one belief that if people are passionate, they become successful in something.


So I've always just been focused on trying to make sure that they find something they're super passionate about. And it doesn't even matter if the thing they find now is the thing they do later because I do believe that passion in itself and taking initiative on your passion is a muscle memory that once you develop it... I have a daughter who loves horseback riding. I don't know if she's going to do horseback riding forever or whatever. But I think that the passion that she has for it, and this desire to be better and to constantly learn more and do more, that in itself is like a replicable muscle memory. So I don't know what the future holds, but I believe that passionate people will always have a path.

Lenny (00:58:01):

Love that. What's a favorite interview question you like to ask when you're interviewing people?

Scott Belsky (00:58:05):

There's a real one, and there's a snarky one. So I do love trying to understand if people are introspective. And so, I like asking about something people have learned about themselves that reveal the limitation in how they work. It's a way to test introspection. And once this person hits their limits or struggles, can they be open and introspective or are they going to blame and point fingers? So I do ask that. I also like the question, like, "Do you consider yourself lucky?" I think it's a fascinating question because also some people who are super insecure about where they are and how they got there and might decline admitting luck, those who are comfortable should admit that they were lucky, I mean, I think the truth is we're all very lucky and certainly privileged. And I just think that that's always an interesting conversation.

Lenny (00:59:05):

What's a favorite reason product you've discovered, app or physical product? Anything that comes to mind?

Scott Belsky (00:59:10):

I've been playing with a product called Queue. And it's Q-U-E-U-E, I think. And it's basically a way to keep a queue of all of this content you want to watch across every streaming platform because there's so much content across so many streaming platforms and to make your own queue and then to see your friends queues and to see what content is in most of the people you know queues, it's actually an incredible graph of kind of stuff that people want to watch or have liked that I think we're going to need in this world where there is just a billion sources of content.

Lenny (00:59:44):

I'm definitely going to check that out. I've been looking for an app like that of I'm sitting in the evening, "What the hell should I watch?" I've seen everything that exists on the internet. So that's awesome. What's a favorite AI tool that you've recently discovered or find useful that isn't something Adobe has made?

Scott Belsky (00:59:59):

Okay. Well, I will mention if it's okay a product that I did invest in.

Lenny (01:00:05):


Scott Belsky (01:00:05):

But it's a product called Tome. And they can take a narrative that you want to put into a presentation, and with AI basically create just a draft of this presentation with imagery and compelling points. And it's almost as if you handed this off to an intern and said, "Come back to me with something I can work with." And suddenly, it's instantly there. So that's been like a fun one to play with.

Lenny (01:00:34):

I will check that out. We'll link to that. Also reminds me Kevin Kelly on Tim Ferriss was talking about how AI and ChatGPT is basically an intern. That's like the level of their skill right now. They're just this intern that's helping out with stuff.

Scott Belsky (01:00:46):

I think that's right. And that's why we have to see it as a resource but not a constraint because, again, it's answering that question like what would it look like if as opposed to doing true distinct thinking per se.

Lenny (01:01:00):

Scott, this is the first time we've ever chatted. But I feel like I know you. You are wonderful. Thank you so much for being here. Two final questions, where can folks find you online if they want to reach out, learn more? And how can listeners be useful to you?

Scott Belsky (01:01:13):

Yeah. No. Awesome. Listen, thanks, Lenny. And your podcasts and your emails are probably among my more forwarded pieces of nuggets and resources that I send to product teams I work with. So thank you for elevating the field for all of us, I should say. And it's an honor to be on this podcast. I'm easy to find, just or @scottbelsky on your favorite social network of choice. And is where I'm writing these days.


And then, you know what? I welcome folks to share what they're working on. I just love taking as much data points as possible. I love connecting dots for people and making introductions. I feel like that can be a contribution to this whole world of better and better products, and I welcome you to reach out.

Lenny (01:02:04):

Awesome. Scott, again, thank you for being here.

Scott Belsky (01:02:06):

Thanks, Lenny.

Lenny (01:02:07):

Bye, everyone.


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