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

by Scott Belsky

Genius is making the complicated simple and relatable.

and smart enough to make the complicated simple and accessible to everyone.

If you avoid folks who are polarizing, you avoid bold outcomes.

Creating something from nothing is a contact sport. The endless debates you endure iron out your team’s preconceived notions, and your vehement disagreements force you to explore unpopular options.

also didn’t aspire to assemble a team of peacemakers.

creative minds have their demons. After all, if creativity is born from struggle, you must be willing to tolerate the residue.

They also pissed off a lot of people, and part of my job was to blunt the pain they inflicted without blunting their impact.

The easiest way to deal with people who make you uncomfortable is to find fault with them; judging others is an easier and more cowardly path than reconciling yourself.

Instead, to build your tolerance of those you struggle with, ask yourself what it is about their behavior that scares you. How might you possess or fear the same characteristics you are resenting in the other person?

The most important part of a team’s immune system helps quickly identify and reject infections. Without a strong response to knowing when something isn’t quite right, small issues can quickly escalate into bigger ones before you have time to snuff them out.

When building a team, hire both doers and dreamers in relatively equal proportions.

During day-to-day operations, doers must be positioned to question new ideas and keep creative whims in check to ensure progress on the biggest ideas that will make the greatest impact. But when a new problem emerges or a brainstorm begins, doers—and their tendencies—need to be suppressed so the dreamers can do their thing.

With every new hire, and in every cycle of innovation and execution, be mindful of your team’s immune system. Let it do its thing, but in times of critical change, take the necessary steps to suppress it.

Don’t just recruit great members; graft them, too. This is about a lot more than onboarding new employees: It’s about identifying with their experience, shining the spotlight on their strengths, and becoming a thought partner, coach, and advocate for them.

One of the best ways to set up new talent to succeed is to align one of their specific strengths with an important task, right from the beginning.

Feedback and discussion provide a constant stream of data for the new employee to consider. For example, I try to foster ongoing conversations around expectations, what I am seeing, and a few things I suggest trying. When there is a gap I see between what an employee is doing versus what I expected, I express it rather than wait. As a new employee, there is no way to graft yourself onto a new team without a sense of how you’re doing and coming across to others and what you could do differently.

Foster apprenticeship.

Healthy teams find ways to have new engineers work with seasoned engineers, even if it means a short-term compromise in productivity.

All too often, the classroom and formal training underserve us. We become dissuaded by theoretical lessons, disenchanted teachers, and a reward system that is all about the grade and not about our love for the trade.

Shed the bad to keep the good.

But comfort also breeds complacency. As learning curves plateau, we lose interest in learning for the sake of learning, and our curiosity wanes.

We stay engaged as we attempt to master something that interests us, but we start to disengage as soon as we gain control over tasks and our interest dissipates. Periodic disruptions of various kinds provide perspective and make people stay fresh and alert.

people want to see opportunity ahead of them, even if they’re comfortable with where they’re currently standing. If you don’t give them that opportunity—or occasionally challenge them to step up to it—you lose the upward mobility of junior people who are waiting for promotions and new opportunities, and your senior staff can tend to get bored and start looking for new jobs.

Promotions and moving people to different roles is one way to push people out of their comfort zone and into a new growth period of their career.

Culture is created through the stories your team tells.

Tales from “in the beginning” tend to have an outsized impact on culture as they reflect the core, founding values of why and how this whole thing got started in the first place.

Culture is not something that begets success, rather, it is a product of it. All companies start with the espoused beliefs and values of their founder(s), but until those beliefs and values are proven correct and successful they are open to debate and change. If, though, they lead to real sustained success, then those values and beliefs slip from the conscious to the unconscious, and it is this transformation that allows companies to maintain the “secret sauce” that drove their initial success even as they scale.

Don’t underestimate the value of a story. Amid the daily grind and the gravitational force of operations, it is easy to ignore, miss out, or altogether obstruct story-making moments.

In large corporations, free radicals question the norms and are regarded as brutally honest and action-oriented individuals.

Be frugal with everything except your bed, your chair, your space, and your team.

don’t be frugal when it comes to paying your team. When you think about compensation, think about how indispensable someone is—or has the potential to become.

The products you use to create impact the products you create.

Amid the fast pace of a start-up relentlessly building and perfecting a product, who has time to invest in proprietary internal tools?

We vastly underestimate how much the products we use impact the products we create.

When you and the rest of your team know who did what, a natural intuition develops for pairing projects with people outside of traditional hierarchical structures. Each person’s expertise becomes clearer, and the team is naturally supportive of those empowered to lead certain projects, regardless of their seniority.

Rather than just publicly acknowledging the leader of every project, you should list the broader leadership teams of every project. By explicitly calling out the leader responsible for each function area—whether it be design, engineering, or legal—you can provide a sense of satisfaction for all levels involved and help the group track the output in each area to the person responsible for it.

The person who did the work should present the work. For example, if a product manager is presenting his or her team a series of mock-ups and wireframes that were designed by a designer on the team, the designer should present that portion of the deck. This gives your staff ownership over their work and also allows the most knowledgeable person to lead the discussion.

False attribution can wreak havoc in a team.

When your A players are playing their A game, you can be creative with how they work. In fact, you need to be. The extremely talented people you love and trust know how good they are, and they thrive working on their own terms. As the leader, you need to carefully balance the need for structure with the need to accommodate the autonomy and idiosyncrasies of your team.

Exceptions shouldn’t happen too often, but when they do, they could be differentiating and critical to your success.

long as you have the right people aligned around the right objectives, be flexible.

superstars insist on working remotely, let them. If two people with complementary skill sets make great candidates for the same leadership role, experiment with coheads. Observe, learn, and then adjust. Despite all the conven...

When you bring a small group of the right people together (and they all join the effort for the right reasons), you’ll find yourself free of burdensome process. When you’re all working toward the same goals and deadlines, fueled by real-time communication, transparency, and a shared sense of urgency, you’ll feel efficient.

as a team grows, misalignment happens. People’s engagement slips to varying degrees. Objectives are clear to some and less to others—and can change regularly. Deadlines need to be mandated rather than suggested. Communication is inconsistent by the sheer fact that everyone isn’t sitting together. As goals and priorities become crooked, performance suffers.

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 tha...

Process is how we force alignment when it doesn’t happen naturally. You schedule meetings, you embed systems for tracking and accounta...

But if not implemented properly, process slows down progress. It can be painful, especially as teams that grew up eschewing mandates mature. Nobody li...

Install process for your team, not for you. A lot of wasteful and painful processes are born from anxiety. When leaders feel insecure about losing touch with parts of their business, they’re liable to create more bottlenecks.

But when you introduce process to your team, do it to solve their problems rather than quell your own anxiety.