The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture
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When the odds are against you, without revenue or margin to protect you, teams and relationships are different. It’s not work; it’s survival and self-discovery.
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It requires immense perseverance, self-awareness, craftsmanship,
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We had to rebuild the Behance Network’s core technology three times.
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Despite the temptation, don’t focus on “good news” at the expense of what’s going south and how to deliver bad news.
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“Yet, uncertainty makes this task difficult. Claiming an unwarranted degree of control on uncertain situations can harm the reputation of the leader in the long run. Whereas a leader who is behaving in harmony with the uncertain nature of a situation would be judged as fair and competent even if sometimes the outcomes are unsatisfactory due to bad luck.”
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There’s no shortcut to deep thinking and crunching through scenarios in the basement of your brain.
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Strive to continually process it rather than let it cripple you, to accept the burden without surrendering your attention.
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What stands in the way becomes the
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way.” Indeed, the frictions we encounter help us find a better way so long as we face them.
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As a leader, you are your team’s window. You need to call out and describe the landmarks that you pass along the way, constantly reinforce the terrain you have already covered, and prepare folks for the map ahead.
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To get through the tremendous voids of nothingness in between the milestones, provide guidance. You’re the narrator of this journey.
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Storytellers make the past relevant to the future, even when it is dry and irrelevant.
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As a leader, you can’t always provide answers. And you shouldn’t, as the correct solution may still be premature. But what you can do is always add energy. This ability to turn negative conversations into positive ones is a trait I’ve always admired.
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But by doing so, it is more difficult to get the right people talking to one another. It’s more important to be collaborative than to be correct.
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Don’t blame yourself for feeling skittish. Avoiding conflict and
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through the uncertainty.” “It’s amazing what you can achieve if you refuse to be discouraged, refuse to let down your team, and you check your ego at the door,” Kegan added. Indeed, the possibilities are endless if you just keep going and, at your most difficult and trying moments, push yourself to do your fucking job.
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“Knowing your own darkness is the best method for dealing with the darkness of other people.” Being in touch with your own flaws helps you support others with their flaws. Discussing your flaws invites others to do the same.
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When front-running the future, the trick is to aspire for a small audience that loves your product rather than aim to please the masses.
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A big part of overcoming doubt is suspending your disbelief. You want to stay grounded as you make decisions, but sometimes you need to escape the gravity of reality to imagine the possibilities.
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You don’t know what you’re capable of. Whether it is
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navigating your career, starting a new business, or overcoming an illness, giving yourself a placebo of sorts that suspends your doubt is one of the greatest factors in making progress.
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It can be hard to see in the moment, but your struggle may mean you’re onto something new that is defensible from competitors and copycats.
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Insecurity work puts you at ease, but it doesn’t actually get anything done.
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When the right question was finally asked, everything became illuminated.
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question won’t spark discussion beyond its answer. 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.
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Every storm better prepares us for the next. Trying again after getting beaten down is never easy—but the important things never are. You will recover and thrive. Do it one step at a time.
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You and your team need to understand when expertise is an advantage and when it is a disadvantage. This all boils down to the industry norms you’re calling into question and whether or not key dynamics have turned such norms upside down. 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.
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It’s less about fixing what’s broken and more about improving what works.
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As you build your team, seek people who have endured adversity. Ask prospective team members about their most defining challenges. Life matures you a lot faster than time, and a lot of life can happen in a very short amount of time.
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Genius is making the complicated simple and relatable.
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Learn to tolerate the people you struggle with. There are many people I have hired over the years whose references included some warnings.
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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?
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As you graft new talent to your team, do whatever you can to attempt to see the perspective of your newest members, and act accordingly.
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Having a new staff member feel like they’re providing immediate value helps ease the team’s immune system.
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When people start to fear losing their bonus or getting dinged in a performance review, they stop toeing the line.
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As you seek to boost productivity and add structure and process to your team, be careful not to disincentivize the risk taking and expression of unique perspectives that got you up and running.
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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.
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you. Too much calm exacerbates any disruption, so building up your and your team’s tolerance for change is a positive long-term strategy for increasing tenacity.
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Your team must feel taken care of and must have no doubt that they are being rewarded as best as possible for their achievements—and then a little bit more.
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You need to allocate time for optimizing the tools your team uses, your internal communications, and the environment in which you create. If you don’t, the products you create will suffer.
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A mock-up turns the lights on.
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Great management is this delegate, entrust, and debrief cycle on repeat.
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We get in trouble when we choose to communicate the easy way versus the right way. As our channels for communication expand, we must endeavor to be more thoughtful about how and when we communicate.
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Leaders who can’t make tough decisions cause their teams to accumulate “organizational debt.”
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Sometimes you need to ask point-blank: Who is holding up progress?
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In this system, “any employee who encounters a policy or process that is hindering their ability to deliver value to the customer can submit the policy/process (and a recommendation) to the program website.”
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Ambiguity kills great ideas, and great leaders kill ambiguity.
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Disagreement is great, so long as the team shares conviction when a decision is made.
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Confrontation tends to be most needed when it is most uncomfortable. It’s the truly tough issues, the ones most likely to advance our potential the most, that we avoid. I am still determined to get a sign someday for my office that simply states NO ELEPHANTS. To eliminate all “elephants in the room,” your team must commit to as much front stabbing as possible.
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If you have conviction in your own ideas and approach, then you should be the most competitive with yourself. Your past personal best—your most productive week, your most efficient sprint, your best-executed event—is what you need to beat. Competing with your past is the purest and surest way to make faster progress without compromising your vision. The greatest successes are the aggregate of persistent optimizations of personal bests.
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