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

by Scott Belsky

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.

The more aligned your team is, the less process you need.

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. I’ve seen some leaders schedule redundant “sign-off” meetings, run daily check-ins, and implement other mechanisms just to achieve peace of mind—for themselves, not for the team.

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

Spend more time on achieving alignment than imposing process.

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.

Audit your processes frequently and always try to cut them down.

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

Knowing how to respect process while not letting it inhibit progress is one of the holy grails of management.

had to learn how to temper my bias toward action with a respect for the processes of those around me.

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.

If it’s memorable or big and in your field of vision every day, you’re more likely to do it.

If a picture is worth a thousand words, then a mock-up answers a thousand questions.

When it comes to strategy and planning, there is too much talking.

It’s as if buy-in and alignment come only from being anchored by something in the visual cortex.

to capture your audience’s attention, you should always couple abstract descriptions with concrete images or physical representations of your idea—as these visual aids appeal to and satisfy our most primal neurological instincts.

Without a mock-up, people are trying to interpret something in the dark by feeling one edge at a time. A mock-up or prototype is worth countless meetings 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.

Ben’s interest is still in studying what works and in fixing what’s broken. He wants to engage people, not impress them.

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

everyone is aligned with the mission and the market forces and is determined to do whatever they can to make the greatest impact, then the pressure to delegate should come from below as well as above. In such an environment, everyone is seeking control for what they think they should be responsible for—often

David Marquet, the former commander of the nuclear-powered submarine USS Santa Fe and author of Turn the Ship Around!, shared with our team at 99U his insights around delegation from his time in the military: The problem is that, in the heat of the moment of conversation, our leadership brains are wired to take control and give direction. It feels good. We get to solve problems, reduce uncertainty by giving instructions, and raise our level of status and authority. Unfortunately what feels good for us feels bad for our people. No one ever did anything awesome or great because they were told to. The degree to which we order people around suppresses any opportunity for greatness. Telling people what to do is the opposite of responsibility. . . . The danger is people are “doing” their jobs, not “thinking” them. Often these actions inadvertently have the effect of reducing the employee’s drive toward empowerment.

Great management is this delegate, entrust, and debrief cycle on repeat.

Aspiring to accommodate many needs and use cases will make it hard for anyone to identify your specialty and feel compelled to engage with it. I call it the “NYC Deli Problem.” If you have signs outside for a salad bar, pizza, Chinese food, and sushi, you’re liable to not be taken seriously for any one of those cuisines despite how good your food may actually be. By attempting to engage with too broad a customer base, you fail to engage with any one customer base deeply.

don’t shy away from being explicit about who you serve and who you don’t. What are you doing and what aren’t you doing? Don’t hedge—you must choose.

Be explicit, and you’re more likely to get what you want.

organizational debt is the accumulation of changes that leaders should have made but didn’t.

“This is the progress paradox,” Glei writes, “by dint of technology, it’s easy to see our progress when we’re doing relatively meaningless short-term tasks, while it’s quite difficult to see our progress when we’re engaged in the long-term, creative projects that will ultimately have the most impact on our lives.”

We need to combat such tendencies with an appetite for the meatier problems before us. Meaningful productivity starts by defining the things that make a big difference and prioritizing them one at a time. Some teams I have worked with call the difference between the big tasks and the little tasks “boulders” and “pebbles.”

I try to spend 80 percent of my time on boulders and 20 percent on pebbles.

Keeping the ship moving, and breaking ice at the bow, is a painful responsibility, but the person who does it is the person who transforms big organizations. Be the person who asks the persistent, and often annoying, questions.

Ambiguity kills great ideas, and great leaders kill ambiguity.

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.

we oscillate between trying to diminish our competitors, trying to copy them, and trying to ignore them. What we should be doing is using them to better understand our market and improve our execution.

Joyce Carol Oates once remarked, “Writer’s block occurs when the writer believes the idea is fraudulent.”

Entrepreneur and investor Paul Graham, founder of the start-up incubator Y Combinator, once remarked in an interview about Facebook founder Mark Zuckerberg: “It’s easier to tell Zuck that he’s wrong than to tell the average noob [new] founder. He’s not threatened by it. If he’s wrong, he wants to know.” Paul goes on to say, “What distinguishes great founders is not their adherence to some vision, but their humility in the face of the truth.”

If the uniqueness isn’t already baked in, and instead only gets sprinkled on top, it’s likely to taste bland.

As comedian Milton Berle once quipped, “A committee is a group that keeps minutes and loses hours.”

When working in a group, innovators must be willing to be the fool.

By having only one problem to crack over an extended period of time, your brain enters a state of deep crunching that is just not possible with too many projects and problems under way. When you’re all-in on one project or approach, you have a better chance of reaching escape velocity, when everyone is focused and aligned.

“Kill your darlings.”

the author Arthur Quiller-Couch was supposedly the first to make the suggestion, which he did in a lecture to a group of aspiring writers in 1914: “If you here require a practical rule of me, I will present you with this: Whenever you feel an impulse to perpetrate a piece of exceptionally fine writing, obey it—whole-heartedly—and delete it before sending your manuscript to press. Murder your darlings.”

You may be telling yourself about the benefits of keeping ideas alive as a way of preserving options, but the truth is that you’re failing to kill your darlings, just like an amateur writer would. Your best chance of succeeding is to consolidate your energy around a singular focus and work like hell to achieve it.

Aaron Levie, founder and CEO of cloud-storage company Box once noted, “To make everyone happy with the decision, you’ll make no one happy with the outcome.”

Don’t be creative for the sake of it, despite the urge to do so. Popular terms and actions are popular for a reason. Adopt simple patterns, proven to be successful, whenever possible, and train your customers only when it’s a new behavior that is absolutely core to what differentiates your product. Familiarity drives utilization.

studies conducted at Swarthmore College examined the psychological effects experienced by “maximizers” as compared to “satisficers.” These studies build on the term “satisficer” that economist Herbert Simon coined in 1956 to describe the decision-making style that “prioritizes an adequate solution over an optimal solution.” While satisficers make a decision once their criteria is met, “maximizers” want to make the best possible decision, and so they scrutinize every option even if they’ve found one that’s good enough. In the Swarthmore studies, as journalist Becky Kane summarizes on Todoist, maximizers reported significantly lower life satisfaction, happiness, optimism, and self-esteem, and significantly more regret and depression, than satisficers. Maximizers were also more likely to engage in social comparison and counterfactual thinking, experienced more regret and less happiness after making a consumer decision, and experienced a greater increase in negative mood when they didn’t perform as well as their peers.

The consequence of starting a project out of sheer passion is making decisions without considering those you’re serving. Empathy for those suffering the problem must come before your passion for the solution.

Big companies are just as bad, often outsourcing the narrative to the marketing department or an external agency. The narrative is not a description of what your product is or does, it is the story of how and why it must exist.

William Gibson is often credited with having said, “The future is here, it’s just not evenly distributed yet,”