How to Manage “the Messy Middle” of the Innovation Process, According to the Chief Product Officer of Adobe

We tend to celebrate the kickoffs and successful completions of big projects. But the real success factors must happen in the middle, the messy middle.

I recently connected with Scott Belsky, author of The Messy Middle and the current Chief Product Officer at Adobe, to discuss how entrepreneurs and corporate innovators can find their ways through the hardest and most crucial parts of any bold new venture. Here’s an excerpt of my discussion:

We all celebrate the launch of a venture or project, and again its completion or sale. Why did you write about “the messy middle” in between? 

Belsky: I wanted to dispel the myth that the journey to make something great is linear. Even the greatest success stories are remarkably volatile and flush with struggle (and when they are shared publicly, they’re drastically edited for egos and sound bites). Developing the muscles for enduring and optimizing your way through the middle stages of a bold venture or project starts with understanding tactics for navigating the lows and capitalizing on everything that works.

What signs do you look for when evaluating the potential of a start-up and their ability to persevere through “the messy middle”?

Belsky: Leading a team through the messy middle requires a tremendous amount of self-awareness and commitment to growth, a willingness to suffer, and an obsession with optimizing not only how a product or service works but also how a team works and how you, as a leader, operates. As an investor, I look for founders that value empathy with their customers (and the work it takes to develop it), recognize the magnitude of the challenges they will face in building a company, and value design, brand, and other success factors that I believe are important.

What are the most common mistakes entrepreneurs make during “the final mile” with their companies, and what strategies can circumvent them?

Belsky: As you enter the last phase of a big project or a company nearing an end, you learn pretty quickly that “the final mile” is a different sport. A great founder or leader or product manager isn’t necessarily a great finisher. With the finish line in sight, your instinct may be to keep doing what you’re doing and race toward the light. But at the end of a venture, everything changes. No matter how accomplished you’ve become over the course of your journey, you’ll need a new set of tactics and a ton of guidance. Instead of enduring and optimizing, you’re closing.

Psychologically, you’ll ponder the implications of finishing and likely have mixed feelings. You’ll start to question yourself and your motivations. As people start to define you with what you’ve created, you’ll need to remember that you are not your work. And most of all, you need to mentally stay in the early innings. I explore these angles and tactics, among many others, in the book.

You write that “the messy middle” is the hardest stage to get through. What separates endurance from simply slogging through?

Belsky: Endurance is about much more than surviving late nights and laboring without reward. It’s about developing a source of renewable energy and tolerance that is not innate. Without any customers or evidence of progress, the continuous validation and encouragement that motivates teams will be absent. Without a steady stream of rewards, you will feel empty. You must supplement this void with manufactured optimism. You will have to endure anonymity and a persistent state of frustration. You’ll have to generate a unique and intrinsic sense of belief in yourself as you manage the blows to your plan and ego.

Sure, your passion for the problem you’re solving will help. But running a marathon while hungry requires supernatural sustenance in the form of some key insights and convictions that I try to cover in the book.

What would you most like anyone stuck in the middle to realize and immediately apply?

Belsky:We all must recognize that the middle stages are intended to be mined. What you learn from the volatility enables you to reach the finish. You must value the hardship as the experiential education you need and the source of the moat around your product or business that makes you competitive. I also advise anyone feeling stuck to focus on the few things that are working and optimize them. When it comes to building products, teams, or processes, you win by iterating whatever is working.