Lessons on product sense, AI, the first mile experience, and the messy middle | Scott Belsky (Adobe)

Scott Belsky is a true product legend. From founding Behance and selling it to Adobe, where he rose to Chief Strategy Officer, to writing the acclaimed book The Messy Middle, his insights have shaped how a generation of builders thinks about creating great products. He’s a sought-after investor and an articulate thinker on the intersection of technology, psychology, and creativity. In a wide-ranging conversation, he shares hard-won lessons on developing product sense, navigating the brutal middle stages of a startup, and how artificial intelligence is set to redefine the very nature of our work.

Key Takeaways

• Conviction is Your Compass: When deciding to persevere or pivot, the only question that matters is whether your conviction in the solution has grown or diminished over time. If it has faded, it's time to move on.
• Empathy Over Passion: The biggest mistake teams make is falling in love with their solution. Instead, cultivate a deep, psychological empathy for the customer suffering the problem; the right solution will emerge from that understanding.
• Master the First Mile: Most teams design the customer's first 30 seconds of experience last. Mastering this "first mile"—onboarding, orientation, and defaults—is critical and must be continuously re-evaluated for new customer cohorts.
• The Power of Subtraction: Aim to build half the features, offer half the options, and target half the market you initially envision. Removing features can often increase engagement with the core value proposition of your product.
• AI Augments Ingenuity: AI won't replace creative professionals or product thinkers. It will act as a powerful tool to eliminate mundane work, collapse functional silos, and expand the surface area of creative possibilities, leading to better outcomes.

Navigating the "Messy Middle": When to Pivot and When to Persevere

Every founder eventually faces a moment of truth. The initial excitement has faded, progress has stalled, and the path forward is unclear. Should you keep going? Scott Belsky offers a simple yet profound framework to answer this question. It all comes down to one thing: conviction.

He advises founders to ask themselves, "Knowing everything I know now, do I have more or less conviction in the problem and the solution I'm building?" The initial passion that led you to leave your job is one thing, but the conviction forged in the fires of early struggles is what truly matters.

Some founders, despite numerous product failures, find their belief has only deepened. They've seen validation from customers and learned invaluable lessons. For them, the advice is clear: stick with it. You're in the "messy middle," and this struggle is part of the process. But for others, the journey has revealed fundamental flaws in their original thesis.

If I knew then what I know now, I would not have done this.

When a founder admits this, Belsky's advice is equally direct. "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." While you shouldn't make a rash decision on a bad day, a persistent decline in conviction is a clear signal that it's time for a change.

Developing World-Class Product Sense

Product sense is an almost mythical quality attributed to the best product leaders. Belsky demystifies it, grounding the concept in two core pillars: deep customer empathy and a mastery of human psychology, especially during a user's initial interaction with a product.

The Power of Empathy

The most common pitfall for product teams is becoming passionate about a specific solution instead of the customer's problem. "Oftentimes the empathy gives you the solution," Belsky explains, "whereas the passion you have for whatever you think the solution is might be 30 degrees off."

True empathy isn't built from data sheets and survey results alone. It requires direct observation. Belsky describes his most humbling moments as a product leader as those spent "shoulder to shoulder with customers, watching them actually go about their day." This provides crucial context that data misses. You see how your product fits into the chaotic reality of their lives—amidst other meetings, notifications, and distractions. This immersive understanding builds intuition, or what he calls the "golden gut," allowing you to truly build for your customer because you can feel what they're feeling.

Mastering the First Mile

Belsky is a vocal advocate for perfecting the "first mile" of the user experience. This is the critical first 30 seconds where a new user is, in his words, "lazy, vain, and selfish." They want to feel successful immediately without enduring any learning curve.

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.

The first mile encompasses three key areas:

• Onboarding: The initial sign-up and setup flow.
• Orientation: A user's ability to understand where they are, how they got there, and how to get "home."
• Defaults: The pre-selected settings and initial state of the product.

This isn't a one-time effort. As a product grows, the customer profile changes. Early adopters are often forgiving, but later, more pragmatic customers are skeptical and have less patience for friction. Products like Photoshop, which went from a high-cost professional tool to an accessible subscription, must constantly reimagine their first mile to cater to a broader, less-trained user base.

The Art of Subtraction: Why You Should Build Half of What You Want

In a world that constantly pushes for more, Belsky champions the discipline of less. His counterintuitive advice is to do half of what you want: build half the features, offer half the options, and target half the market. This philosophy was learned the hard way during the early days of Behance.

The initial version of Behance was a complex product with features for groups, a tip exchange, work-in-progress snapshots, and full portfolios. The team was hedging its bets. But they soon realized that some features were cannibalizing the core action they wanted users to take: publishing portfolio projects.

They started a "killing spree." First, they killed the tip exchange, and portfolio publications went up. Then they killed groups, and publications went up even more. "If you make the whole product about one thing," Belsky realized, "everyone does that one thing. That core crank operates at 10x the velocity." This ruthless focus on the single most important metric is what propelled the business forward.

His advice to teams struggling with their MVP is to "optimize for the problems you want to have." You want the problem of customers loving your core product so much that they demand it on new platforms or ask for more sharing capabilities. Don't build those things upfront. Instead, focus only on what's necessary to get users to the point where they care enough to ask for anything at all.

The AI Revolution: Reshaping Product, Design, and Work

As a leader at Adobe, a company at the forefront of generative AI with tools like Firefly, Belsky has a clear and optimistic vision for the future. He believes AI's greatest promise is its ability to liberate human potential by eliminating mundane, repetitive labor—the "work" in "workflow." This allows us to move into a state of pure flow, where ideas can be developed and explored with unprecedented speed.

How AI Will Transform Product Teams

Belsky predicts we are entering an era of the "collapsed stack" within organizations. Instead of going through a data analyst to get an answer, a PM will be able to query the data directly. Instead of waiting for mockups, a designer will be able to generate dozens of variations instantly. This empowerment reduces the "game of operator" and allows small, cross-functional teams to run circles around larger, more bureaucratic organizations.

This shift fosters an "idea meritocracy," where influence is based on ingenuity and creativity rather than title or team size. A data analyst, freed from redundant requests, can now spend their time thinking more strategically about the business. A PM can do more of their own design and data work, becoming a more versatile and effective leader.

The Future of the PM Role

For product managers specifically, AI will be a superpower for expanding the "surface area of possibility." Great product development involves exploring many potential paths, culling them down, and refining the best ones. AI drastically reduces the time required for this exploration. Belsky shares an anecdote about a Hollywood director who uses ChatGPT not to write scripts, but to generate five different scenarios for a scene. He doesn't use any of them directly, but the output expands his creative palette and helps him identify paths not to take.

For PMs looking to stay ahead, Belsky's advice is simple: "Play." You have to use these tools—write poems, draft emails, generate images—to build an intuition for what's possible. Curiosity and hands-on experimentation are the only ways to understand how this technology will reshape our work and the world.

Conclusion

Scott Belsky's career is a testament to a set of core principles that stand the test of time. He reminds us that enduring success is built on a foundation of unwavering conviction and a deep, psychological understanding of the user. It requires the discipline to subtract rather than add, focusing relentlessly on the core engine of your product. As we enter a new era powered by artificial intelligence, his optimism is a powerful call to action: to embrace these new tools not as replacements, but as catalysts that can unlock unprecedented levels of human ingenuity. Because, as he notes, "nothing extraordinary is ever achieved through ordinary means."