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

by Scott Belsky

How often are you merchandising your mission and road map to your team? Likely not enough. Are you ensuring that every new member of your team is adequately caught up? Are you proactively identifying people who seem misaligned and taking the time to get them up to speed? Such alignment will expedite progress and boost quality better than any formal process could.

Your challenge is to lead an efficient team that is fully aligned with as little process as possible.

As you can tell, I’m wary of adding processes as the perpetual solution for internal challenges. However, I have also learned over the years—often the hard way—how important it is to let people have their own process.

my effort to speed through—or steamroll—another team’s process would often backfire. Matias’s team had developed ways to explore different approaches to problems before choosing a solution.

is healthy to have some degree of process intolerance—an innate disdain for undue procedures and waiting; after all, waiting for a green light never gets you there first (though red lights certainly prevent accidents).

Merchandise to capture and keep your team’s attention.

Perhaps one of the most important unspoken roles of a leader through the messy middle of a project is that of internal marketer. For all the emphasis around obsessing over your customers and your public brand and message, there is surprisingly little focus on the internal brand and message. What do your employees think of their work, the team’s productivity, and their mission? Do they even know the mission?

Progress is the best motivator of future progress, but it must be merchandised sufficiently so that people feel it.

“The more frequently people experience that sense of progress, the more likely they are to be creatively productive in the long run. Whether they are trying to solve a major scientific mystery or simply produce a high-quality product or service, everyday progress—even a small win—can make all the difference in how they feel and perform.”

A mock-up or prototype is worth countless meatings and debates. A mock-up turns the lights on.

A very simple and common mistake I see among passionate founders and designers is to present a new idea in the best possible light to the point of promoting rather than explaining.

Something so polished, without any blemishes, is harder to grasp. The roughness of a new idea provides the texture your team or potential investors need to believe in and latch onto.

At Benchmark we called these CEOs “promoters.” They would come in with a seemingly perfect story, broad generalizations about their industry, and wou...

Whether you are sharing an idea with colleagues or pitching an idea to investors, be less polished and more real.

little texture in the form of uncertainty and admission of challenge is helpful for everyone. The right partners will see your challenges as potential rather than weakness, and your honesty will set the right tone for future collaboration and navigating the ups and downs of the journey together.

Only when your team members feel in control of their own projects will they feel sufficiently motivated and accountable for completing them.

He has long advocated for every function and project in his company having a “DRI”—a Directly Responsible Individual—whom the entire team knows to go to and rely on for that particular area.

Elon Musk says that you can stop anyone on the SpaceX factory floor and ask them what they’re doing and why it’s important.

When people know where their small part fits in the whole, they recognize how indispensable their work is. They feel more accountable.

My preferred method of evaluating delegated tasks is holding debriefs after both major milestones and fiascos.

For sensitive topics, the nonverbal cues you can see only in person are extremely important. However, sometimes the formal nature of a meeting or long email can make a small issue seem like a bigger deal than it actually is.

As the trope goes, “The medium is the message.”

Communication often contains too much couching and disclaiming. Everyone has a different style of working within a team dynamic, but the more you can just say it like it is and foster a working environment where people are straightforward and honest about where they stand, the better your team will function, and the faster you’ll solve problems.

Simple truths resonate; they stick in your mind, whether you like it or not. And that’s all the more reason to seek them and state them.

Most people’s natural tendency is to please and accommodate others.

Shorter emails get faster response times. Fewer words go further (and are listened to more intently).

Leaders who can’t make tough decisions cause their teams to accumulate “organizational debt.” Like the notion of “technical debt,” which is the accumulation of old code and short-term solutions that collectively burden a team over time, organizational debt is the accumulation of changes that leaders should have made but didn’t.

When you’re unsure about something, whether it be an email or a comment made in a meeting, act on it or ask about it. Stuff that sits idle, misunderstood by you and likely others as well, plagues progress. Handle something once, not many times.

A lot of big problems don’t get solved because we can solve small problems faster.

Extinguishing a small brush fire will make you feel accomplished more quickly than making a small dent tackling a forest fire. But one causes much more damage when left unchecked than the other.

In every project, there are a few boulders and lots of pebbles. The boulders are hard to move up the hill, but they materially impact your project and differentiate you from others.

I try to spend 80 percent of my time on boulders and 20 percent on pebbles. But that’s easy to say, hard to do.

we’re still drawn to the quick returns. Resist.

Too much process leads to bureaucracy, and any team of size is plagued by it. Bureaucracy is like a frigid ocean with an icy surface that is just about to freeze over.

If you work in or with a big company, it may be tempting to blame the bureaucracy—the company’s size, its excessive procedures, the layers of management needed to sign off on decisions—for the lack of innovation and agility you feel.

However, the culprit is often our own inability to keep projects moving. Big companies can innovate—it just takes small groups of people willing to sustain motion. The motion that keeps the ship moving is persistent questioning.

Be the person who asks the persistent, and often annoying, questions.

Don’t try to get everyone to agree. Instead, put people on the spot to share their objections. When there is ambiguity about the next step, call it out. Ambiguity kills great ideas, and great leaders kill ambiguity.

Conflict avoidance stalls progress.

“Critics won’t like it.” “The team is not fully confident in scalability.” “We haven’t tested enough.” Such proclamations yield a series of discussions about what still needs to be done to get us “ready.”

But your job as a leader of change is to challenge peace as a default. Create an environment where people can withstand a fight and engage in friction as it arises.

“Who exactly claims we’re not ready to launch this? What, specifically, needs to be done for us to be ready?” “What is our MVP? Have we not achieved that yet?”

Ultimately, you want a team that values conflict as a means to make bolder decisions and take the required risks for a more exciting end.

Disagreement is great, so long as the team shares conviction when...

“A good team does a lot of friendly front stabbing instead of backstabbing. Issues are resolved by knowing what they are.”

Competitors boost your productivity by keeping you on your toes. They help establish your market to attract capital and talent. And multiple teams competing to offer a better and more affordable experience is great for customers and healthy for your industry.

Sometimes the thing you admire most in your competitor isn’t smart or scalable. They may be doing something that is temporarily advantageous to their interests but, over the long term, unsustainable.

your competitors play a critical role in the health of your industry.

Over time, every company in a field builds on one another and helps expand the potential size of the market.

Be grateful to your competitors for never letting your product—and process—become too comfortable.