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by
Scott Belsky
While difficult to withstand and tempting to rush, the middle contains all the discoveries that build your capacity. The middle is messy, but it yields the unexpected bounty that makes all the difference.
What’s in the middle? Nothing headline-worthy yet everything important. Your war with self-doubt, a roller coaster of incremental successes and failures, bouts of the mundane, and sheer anonymity.
You’ll become mired in logistics and daunted by the unknown. You’ll frantically attempt to level out your overworked synapses. You’ll be in a freefall without knowing how far away the bottom is—and that’s when the headwinds kick in. Everyone will doubt you. You will struggle to see your own progress. You’ll realize that your industry, your team, and your competitors don’t like change—and society doesn’t, either. Not even your customers.
The Start
Volatility is good for velocity. The faster you move and the more mistakes you make, the better your chances of learning and gaining the momentum you need to soar above competitors. Moving fast means conducting lots of experiments—many of which will fail—and making quick turns that are liable to leave you and your team dizzy. This volatility can hurt morale and cause anxiety, but you have a better chance of extraordinary results.
When you make your way through “Endure,” you’ll be greeted by a more optimistic and actionable “Optimize” section that is all about capitalizing on your strengths and improving every aspect of your team, product, and self. Enduring and optimizing is the rhythm of making—the pattern of ups and downs that every journey takes you through.
In Zen, the Buddha says you cannot travel the path until you have become the path yourself.
The middle miles of a venture are full of ambiguity, uncertainty, fear, runarounds, crises, disagreements, and endless bouts of the mundane. Every time you untangle yourself and find your way out of a jam, you’ll fall into another one sooner than you think.
You can get the important stuff right and still lose by not enduring long enough.
With a commitment to suffering, teams are able to tolerate struggle and overcome major psychological challenges like, for example, throwing everything away and trying again.
Your story has more gravity than you realize. Your job is to help your team make sense of the strategy—what they’re seeing, doing, and working toward. You are the steward of your team’s perspective, and there is always a way forward so long as you explain it.
If an organization doesn’t let politics and burdensome processes get in the way, then size becomes an advantage. If not, well . . . big companies become couch potatoes while the future of their industry passes them by. Of course, this all comes down to the leaders themselves and whether or not a culture supports people stepping out of their traditional roles. Fight corporate obesity by gathering the right people in a room and depoliticizing process as much as you can.
If the cost of waiting exceeds the benefits of acting now, you have a job to do—DYFJ!
One of the worst tendencies of the messy middle is pulling wildly fresh insights back toward the mean of normalcy. Don’t let this happen to you. While society wants you to conform, it needs you to break the mold to help us see differently and make life better for the rest of us.
A question informs the answer more than we realize.
The perfect question is a key to clarity. It unlocks truth and opens minds. It is distilled by having empathy for your customers’ struggles and ignoring sunk costs and past assumptions to get at the root of a problem. When you’re building something new, focus on asking the right questions instead of having the right answers.
Strategy is nourished by patience.
This!
While a great strategy can be conceived quite quickly in a vacuum void of time and reality, it can be executed only over a long period of iteration, agony, and harsh reality (the messy middle!). To allow strategy to unfold, you need to refactor your own expectations and measures of progress while developing a culture and structure that ensures your team has the patience to stick it out with you.
Teams must therefore build systems to nourish patience, culturally or structurally, and you must be willing to defend your long game.
Designing the structure of a project or company to foster patience is ultimately an effort to limit our natural tendency to obsess over measuring progress with traditional near-term measures.
If you want to be the industry leader, sometimes you need to take the difficult path. Be wary of the path of least resistance. It may look compelling in the short term but often proves less differentiating and defensible in the long term. Shortcuts tend to be less gratifying over time. The long game is the most difficult one to play and the most bountiful one to win.
Innovation happens at the edge of reason, and you can’t reach the edge with a team of similar people.
the 70/20/10 model for leadership development. The model suggests that when it comes to training leaders, only 10 percent happens in a classroom through formal instruction, 20 percent is all about feedback exchange and coaching, and a whopping 70 percent is experiential.
proactive changes that feel premature are far better than reactive changes that feel inflicted upon you.
The best teams are more credit sharing than credit seeking; rather than shine a spotlight at the top, they try to trickle the credit as far down as it goes. Be meritorious by assigning credit truthfully. As you recognize people who work for you, assign credit as you would influence. Ultimately, you want the people who really did the work to get rewarded and have more influence next time around.
While you may think assigning credit is about rewards, it’s really about assigning influence for future decisions.
it is hard to build something new within the confines of a structure built for the past, or later stage products.
What’s the solution to the misalignment that comes with growth? Process—the very thing you didn’t need in the early days. Training programs, daily staff meetings, organizational structure diagrams, approval processes: These are the mechanisms we throw at misalignment to ensure that a group of people think and act in tandem. Process is how we force alignment when it doesn’t happen naturally. You schedule meetings, you embed systems for tracking and accountability, and you install more managers.
The conundrum of process is we all need some, but too much is lethal. The more aligned your team is, the less process you need.
Spend more time on achieving alignment than imposing process.
Refer to this for the impact method. First we look at big goals related to mission alignment and values aignment, then we look at org functions, then peopl in tthisnfunctions and then processes
Perhaps one of the most important unspoken roles of a leader through the messy middle of a project is that of internal marketer.
This!
When it comes to strategy and planning, there is too much talking. I recall meetings at Adobe, board meetings at nonprofits like the Cooper-Hewitt National Design Museum, and brainstorming sessions with countless start-ups where all people do is pose questions in different ways: “Maybe it should do X?” “Maybe the better approach is what Y company does?” “Why don’t we try doing Z instead?” Often the different parties aren’t even in agreement on what exactly it is they’re trying to answer. The discussions therefore stay at a very abstract, conceptual level until someone has something visual or
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The roughness of a new idea provides the texture your team or potential investors need to believe in and latch onto.
Great management is this delegate, entrust, and debrief cycle on repeat.
Take great care to ensure past assumptions and old truths never obstruct new discoveries. Be open, humble, and eager to learn that you’re wrong—before someone else does.
You will look to groups for decisions when you should be looking to them only for guidance.
Hesitation breeds incrementalism—the tendency to make changes too muted, too slowly, and too late. You need to attack the hesitation and galvanize the troops to move forward without looking back.
Don’t give those resistant to change false hope for things staying the same; when a decision is made, declare the implications and chop off the rearview mirror.
It’s easier to disrupt the norm by being familiar.
Countless studies have shown that overscrutinizing drains our working memory, which we desperately need to complete cognitively demanding tasks.
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
the first mile of a product experience is increasingly neglected over time despite becoming more important over time. As your product reaches beyond early adopters, the first mile will need to be even simpler and account for vastly different groups of “newest users,” not just the power users you were originally hoping to attract.
Your challenge is to create product experiences for two different mind-sets, one for your potential customers and one for your engaged customers. Initially, if you want your prospective customers to engage, think of them as lazy, vain, and selfish. Then for the customers who survive the first 30 seconds and actually come through the door, build a meaningful experience and relationship that lasts a lifetime.
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.
Willing > Forgiving > Viral > Valuable > Profitable As you roll out a new product, you should target different types of customers at different stages. At first you want customers who are more akin to testers, willing to try, and likely suffer through, the barely viable version of your product. Then you want customers who may not be testers, but are forgiving of the inevitable bugs and gaps in a new product. Once your creation is ready for prime time, your most valuable customers will be those who are viral—customers most likely to share their experience with everyone they know. As your
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Scott Adams, the creator of Dilbert, calls Systems Thinking: choosing your projects based on the skills and relationships you will develop.”
Tim goes on to explain, “This is important because the skills and relationships you develop persist beyond the failure of any single isolated project,
we should all make a few bold bets early in our career to do something first and redefine a category. But throughout our careers, we should challenge ourselves to say yes only to things that bring our skills and network to a new level. Our natural drive to say yes to as much as possible, if only for optionality, may help us in the beginning of our careers but hurts us later on.
I am struck by how great advice in one context is horrible advice in another. Not only must you discern criticism from cynicism, you must also determine when “best practices” become antiquated.
The best advice doesn’t instruct—it provokes.
the real value of advice comes from reconciling its contradictions.
