The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture
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What I like about Ben’s “chapters” approach is that each one applies to everyone in the company and embodies a goal rather than a tactic. Each chapter requires a fresh perspective on the product, renewed empathy with the product’s users, and a candid assessment of the team you have and the team you need. A chapter is a clear goal, underscored by why it is important, and then every team determines its tactics. As a chapter comes to an end, Ben believes teams must be reflective and rewarded.
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Chapters help break down the long timescale it takes to build something extraordinary.
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Ben aspires to provide a narrative. “It’s the dream, the drama, the ups and downs—these are the moments and stories that keep us all engaged,” he explained to me. “But you need a mission that can generate the many mini narratives required to carry you throu...
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Of the first dozen or so people on our team, ten of us were still working together seven years later. The degree of loyalty, tolerance, patience, and shared commitment to a mission was admittedly our team’s only advantage executing in a space that we knew very little about.
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Cofounder of project management software company Basecamp, Jason Fried, makes the point that the best start-ups are really just “stay-ups.” As he explains it, “Outlasting is one of the best competitive moves you can ever make.”
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You should be proud of what you’ve accomplished, but never satisfied.
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If your team is not in a good place or your office culture is lacking, your most valuable resources will not be able to make great products or execute well over time. Your team genuinely needs to be as important to you as what you’re making. I have met many founders who obsess over product and steamroll their team. Most of them have failed. Team comes first.
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I’ve seen many startups shift from doing more with less to doing less with more once they’ve raised funding. It’s
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As you assemble your team, look for people with excitement about the idea, ability to contribute right away, and the potential to learn. What your team lacks in experience they can make up for with initiative. One common principle successful founders swear by is hiring for initiative over experience.
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Malcolm joined us as the third member of our dev-ops team, which is a group of engineers dedicated to the infrastructure, stability, and security of Behance’s platform.
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The dev-ops team is at the front line of every nightmare situation: spam problems, security breaches, latency in the speed of millions of portfolios loading for millions of visitors every day, and, when the site goes down, the dev-ops team diagnoses the problem and fixes
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Skills may be shared, but sheer initiative (and the energy and enthusiasm that comes along with it) helps the culture and spreads like wildfire—the good kind of fire.
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In an interview with John Maeda on his blog, technologist Nicholas Negroponte said it best: “Where do new ideas come from? The answer is simple: differences. Creativity comes from unlikely juxtapositions.”
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Closing the confidence gap of your newest hires is more important than closing the skills gap. You can always provide more formal skills training over time, but building confidence up front is a critical ingredient in unleashing someone’s potential in a new team.
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Healthy teams find ways to have new engineers work with seasoned engineers, even if it means a short-term compromise in productivity. They seat new designers next to experienced designers to foster the ambient knowledge exchange that only happens in proximity to one another.
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I recall Netflix’s Reed Hastings at an event called Founders in Dublin, Ireland, talking about the differences between a family and a sports team. In a family, he explained, you accept people for who they are—and you can’t change them. If you have an uncle who shows up every Thanksgiving and gets inappropriately drunk, for better or worse, he’s still your uncle. But in a sports team, you have high expectations of one another and have an obligation to change and improve the inner mechanisms of the group. Everyone needs to pass the ball. Your position is never set—and you’re always out to win. ...more
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If you don’t weed out the sources of angst, you risk losing your key players. People join an exciting project or high-performing venture to do the best work of their lives. If they’re not working with people they admire—creators who are fully committed to one another and to the work—they leave. If you’re hesitant to let underperformers go, you’re punishing the best performers by limiting their potential, and you’re strangling the team’s prospects.
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As you lose people who aren’t a good match your team becomes stronger. Be great at retaining your A players, and less so with your B players.
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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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Culture is created through the stories your team tells.
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The stories a team recalls and shares about itself serve as a continual reminder for everyone of why they’re there and what makes the team special; they reinforce the foundations of a business and the aspirational elements that tie people together.
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Every team has a few “culture carriers” that are especially good at capturing great stories and retelling them. Culture carriers embody the themes that these stories represent, and their unique abilities to reinforce team culture need to be encouraged and celebrated.
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We make stuff often, and we therefore fail often. Ultimately, we strive for little failures that help us course-correct along the way, and we view every failure as a learning opportunity that’s simply part of our experiential education.
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how you locate and design your space is as important as your team’s skills, because your environment impacts how focused, motivated, and creative you are.
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Pixar’s “town square concept,” an area located at the building’s center that also housed the bathrooms. The idea was to pull people together every day, whether they liked it or not, to promote “serendipitous idea exchange” when nature called. Collisions between people from different teams, Steve felt, were core to Pixar’s creative process.
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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. Many companies wrongly focus on one’s past salaries and assigning people to “salary bands” that allow themselves to be subconsciously biased by age, years of experience, gender, and other characteristics that don’t correlate with indispensability. While these companies may get away with underpaying someone in the short term, great talent tends to recognize their own value over time. When they do, their teams pay the price in either ...more
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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
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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.
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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.
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There was a comfortable tension I was optimizing for having a leadership team that had to work together to build out our various engineering functions, such as front-end development, back end, systems architecture, and mobile.
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When you have the right people, there are no rules for how the team must be structured. 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.
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Small teams run circles around big teams not because they are so small but because they are so aligned that there is only thought and action without anything in between. It’s a beautiful thing.
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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.
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The conundrum of process is we all need some, but too much is lethal.
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when you introduce process to your team, do it to solve their problems rather than quell your own anxiety.
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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?
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Creating the equivalent of billboards, commercials, and hypertargeted subliminal advertising within your team helps foster alignment and productivity. Seriously!
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When you must implement a new process, give it some beauty. Loyalty to a new system comes from believing in it and being attracted to it.
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If a picture is worth a thousand words, then a mock-up answers a thousand questions.
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Ideas are misunderstood unless they can be visualized. Doubts and confusion can be cleared in one fell swoop by a simple image of visualizing a potential solution. When a visual is put up on a screen or a prototype is passed around, the whole conversation becomes more productive and specific.
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Matias started taking the random concepts we had been sketching on a dry-erase wall and mocking them up in an Adobe Illustrator document. (We always used Illustrator at the time for mock-ups; now we use AdobeXD.)
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I realized that a few hours of work on some thoughtful mock-ups would probably save us many more days of wayward deliberation.
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Ben was visiting New York City to bring on some seed investors with product and design experience.
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Employees struggle because they don’t have control over what they are ultimately responsible for.
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Great management is this delegate, entrust, and debrief cycle on repeat.
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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.
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In the early stages of articulating a product vision, 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.
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For example, when I get emails from founders I’ve invested in asking for help with networking and hiring, I am far more engaged by a specific question like “Do you have any leads for a junior designer with experience developing brand identities?” than “Any talented people I should meet as I build the team?” Be explicit, and you’re more likely to get what you want.
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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.
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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 decision is made.