The Messy Middle

“A leader that embraces uncertainty would be open to experiment with different ideas and let others experiment, too, rather than claiming to know the correct answer all the time.”

Steve was the embodiment of the famous advice to have “strong opinions, weakly held.” Only by letting go are you able to truly attempt a new perspective of your venture before you quit.

Whether you’re an author suffering from writer’s block or a start-up team struggling to satisfy its customers, the solution is to change the question you’re asking. If the original question plaguing you is “Why aren’t people signing up for our product?” maybe the better question is “What kinds of people would benefit most from our product?” When you feel lost in ambiguity, ask a different question.

Rather than believe you can just “do it better” than your incumbents, anchor your thesis on what you believe everyone else is wrong about. More important, your team must value the benefits from sticking together long enough to ramp up expertise, gain velocity, and allow a long-term thesis to play out.

The Product Life Cycle Customers flock to a simple product. The product adds new features to better serve customers and grow the business. Product gets complicated. Customers flock to another simple product.

Products that retain their greatness over time tend to hold simplicity as a core design tenet.

Why is it so hard to keep a product simple? A big part of the problem is that you become intimately familiar with your “power users,” the small number of customers who use your product the most. This group of customers is also often referred to as the “vocal minority.”

Forcing yourself to have a “one feature in, one feature out” guideline will help you develop your product with a bias toward simplicity. While simplicity benefits your newest customers and the majority of your current customers, it also benefits your own process to grow your product and solve problems as they arise. The more dynamic your offering is, the harder it is to diagnose what’s working and why. But with fewer moving parts, you’ll have a better understanding of which levers to pull at which times for which outcomes. Your intuition is sharper when your product is simpler. For the sake of your own focus and ability to make great product decisions, reduce and add to your product in parallel.

“The question that I find most helpful to ask is, ‘if you had to keep 10 percent, which 10 percent would you keep, and if you had to, absolutely had to, cut 10 percent, which 10 percent would you cut?’ The interpretation of the responses is just as important as the responses. It only requires one vote to cut.

Some decisions are consequential and irreversible or nearly irreversible—one-way doors—and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before. We can call these Type 1 decisions. But most decisions aren’t like that—they are changeable, reversible—they’re two-way doors. If you’ve made a suboptimal Type 2 decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through. Type 2 decisions can and should be made quickly by high judgment individuals or small groups.”

It’s easier to disrupt the norm by being familiar.

The only time you should force new behaviors or terminology is when they enable a unique and important value in your product.

Familiarity drives utilization.

Rather than seeking more options, remind yourself that you make progress only once a decision is made, and you can always backtrack or adjust as you learn along the way.

The best design often goes unnoticed because something is removed that wasn’t meant to be there in the first place.

When we spend so much time focusing on making what’s behind a locked door so brilliant, we sometimes forget to give the user the key.

You need to prime your audience to the point where they know three things: Why they’re there What they can accomplish What to do next

This lazy-vain-selfish principle is true for all kinds of product experiences, online and offline. In the first 30 seconds, your visitors are lazy in the sense that they have no extra time to invest in something they don’t know. They are vain in that they want to look good from the get-go when they engage with your product or service. And they’re selfish in that despite the big-picture potential and purpose of what your product stands for, they want to know how it will immediately benefit them.

If you feel the need to explain how to use your product rather than empowering new customers to jump in and feel successful on their own, you’ve either failed to design a sufficient first-mile experience or your product is too complicated. Having to explain your product is the least effective way to engage new users.

The absolute best hook in the first mile of a user experience is doing things proactively for your customers. Once you help them feel successful and proud, your customers will engage more deeply and take the time to learn and unlock the greater potential of what you’ve created.

When it comes to the adoption of new products and ways of working, novelty often precedes utility. As you’re building new products and experiences for customers, consider how they will be novel before they prove useful. Don’t bury a certain feature or functionality merely because it isn’t essential for the intended use of your product. Your most important feature may be whatever gets people through the door. Sometimes the initial reason to use a product, and get through the first mile, is to have fun.

As Jerry Seinfeld once explained in an interview with Harvard Business Review when he was asked where his best ideas come from, “It’s very important to know what you don’t like,” he explained. “A big part of innovation is saying, ‘You know what I’m really sick of?’ … ‘What am I really sick of?’ is where innovation begins.” What frustrates you likely frustrates many others.

At this stage of your project, you will benefit most from customers who expect rough edges and are willing to share feedback, and continually give your product more tries as it evolves.

You don’t want too many, because you want to get to know them. These early customers get what you’re doing and are willing to participate.

The narrative is not a description of what your product is or does, it is the story of how and why it must exist.

The narrative should always be framed in the context of life itself. How does your product empower people? Does it help people save time or make them forget time? How does it take natural human tendencies into account, like the desire to look good or make better (and fewer) decisions? And most important, what about your creation will eventually be taken for granted? There’s nothing more impressive than inventing what becomes obvious. The only way to create something that withstands the test of time and becomes a critical part of your customers’ lives is to understand the broader narrative around your product.

You’re running a race to be the very first team to get it right, not the first to cross the finish line.

Were these features a failure? It depends on whether you’re measuring them as an engagement driver or an interest driver. This feature may have failed in engaging users on an ongoing basis but may have been wildly successful in getting customers to download the HBO GO app in the first place.

Any great advertising mind will tell you that a great narrative about your product or service is not a tell-all: It must be short and, more important, it must tap into the natural human tendency to want to learn and understand something that is not fully revealed or infinitely available.

Loewenstein outlines five curiosity triggers that alert people to information gaps. They consist of questions or riddles, unknown resolutions, violated expectations, access to information known by others, and reminders of something forgotten. The best advertisements, and most-clicked headlines, play on most if not all of these triggers.

Business plans are a standard part of building a new venture, but they should be approached as a thought process, not a map. Adaptability and instincts make all the difference. You make progress by planning, but you succeed by deviating.

Tim had a simple litmus test for the commitments he made: Was it something that could be “a first” or a “category killer”? He wanted to hold out for projects that could really redefine a category rather than keep him in a competitive space.

‘Will I develop relationships and skills that will persist beyond this project and help me even if this project fails?’ That is really the hurdle for me saying yes to new options and opportunities.”

One of the world’s greatest experts in decision making is American psychologist Barry Schwartz. In his revered 2004 book The Paradox of Choice: Why More Is Less, Schwartz details how considering more options often makes us less satisfied with the eventual decision we make, not more certain in it.

“endowment effect.” This describes how we have an inclination to disproportionately value things because we own them.

Common sense and near-term metrics help you optimize your product incrementally and reliably—but iconic and breakthrough product insights are not the result of trying to improve a metric. In contrast, great inflections are the result of instincts for what will serve your long-term goals; they’re about feeling, not thinking. In some ways, instincts precede awareness and help you make a decision months or years before that data prove it obvious.

The cost of expertise is familiarity and becoming biased against new ways of doing it.

Your lack of experience actually gives you the confidence to question assumptions that industry experts wouldn’t dare defy. That inexperience can make you more open and confident with subjects you’re naive about—but that naivety will become a disadvantage over time as your success is determined less by openness and more by execution.

One of the best ways to maintain (and reclaim) the benefits of naivety is to surround yourself with different people. A team of people from different backgrounds and industries will keep you questioning assumptions.

In order to become aware of what you can’t see, attempt to determine how you’re coming across. For example, ask people, “If you were me right now, what would you be doing differently?” This question not only yields advice but also gives you a sense of how others view your position and actions.

A great litmus test for whether you should do something is if it distracts you. Something that doesn’t distract you from everything else in your life is unlikely to ever get sufficient attention from others, never mind the attention it deserves from you. Distraction is a form of natural selection.

The invigorating sensation you get from a jam-packed schedule is nothing more than a gamble against the odds. A full schedule, without any margin for error, puts your entire day at risk. When you get away with it, you feel lucky. But when one thing goes wrong, the whole day piles up.

At some point, relentless focus blinds your peripheral vision, and your determination becomes a liability.

It is humbling to realize how myopic your perspective is, and it is inspiring to contemplate the expansive terrain of possibility that surrounds you. Distancing yourself from your daily battles and pursuits restores your energy and refreshes your imagination.

Imagination happens only when your mind has the freedom to run rampant. When you’re always connected and able to find an answer, you stop wondering and wandering. Unfortunately, in the modern day of reactionary workflow, our minds seldom run free.

To keep perspective and nourish your imagination, create windows of nonstimulation in your day, rituals for disconnection, and periods of time in your life where you get out of your element and allow for new questions and curiosities to take hold.

Keep reminding yourself that success doesn’t mean you know what you’re doing. Success means that many forces aligned in your favor, that your team outperformed itself, and that you kept yourself from screwing it up.