| In JC’s Newsletter, I share the articles, documentaries, and books I enjoyed the most in the last week, with some comments on how we relate to them at Alan. I do not endorse all the articles I share, they are up for debate. I’m doing it because a) I love reading, it is the way that I get most of my ideas, b) I’m already sharing those ideas with my team, and c) I would love to get your perspective on those. If you are not subscribed yet, it's right here! If you like it, please share it on social networks! Share 💡JC's Newsletter
In the spotlight today is a riveting book I've just read, titled 'The Messy Middle’ by Scott Belsky. The content of this book revolves around the challenges of entrepreneurship and the necessity of perseverance. The essence of the book cannot be overemphasized for entrepreneurs and teams who are in the 'middle miles' of their venture, tackling everything from fear and uncertainty to crisis management and the mundanity of day-to-day operations. If you're interested in the struggles and triumphs of entrepreneurship, I highly encourage you to get a copy of this book. It's a powerful tool to equip you with the necessary mindset, techniques and perspective to navigate the entrepreneurial landscape.
Keeping our product functional was a game of Whac-A-Mole: Every fix seemed to break something else. But we were determined to get it right. The middle miles of a venture are full of ambiguity, uncertainty, fear, runarounds, crises, disagreements, and endless bouts of the mundane. Every time you untangle yourself and find your way out of a jam, you’ll fall into another one sooner than you think. Endurance is about much more than surviving late nights and laboring without reward. It’s about developing a source of renewable energy and tolerance that is not innate.
Notes: How would a skeptical investor look at your numbers? How would an impatient new customer attempt to navigate your product? What are competitors saying about your product? Actively seek out the negative trends as well as the positive, as your longevity over time will be determined by your awareness of weaknesses as much as your strengths. “You must tell the truth without destroying the company. To do this, you must accept that you cannot change the truth. You cannot change it, but you can assign meaning to it.
Notes: Be very open to understanding what people say negatively about us. It does not mean they are right or that we should optimise for it. In any case, we will learn. Never stop sharing the hard truth, and always explain why. It confirms my view that we should not celebrate accolades like getting “press” that we paid for or winning awards
No matter what your creative endeavor is, uncertainty will be lingering around every corner. There is simply no way around uncertainty and the angst it will cause for you and your team. Strive to continually process it rather than let it cripple you, to accept the burden without surrendering your attention. Society’s natural resistance to ingenuity surfaces in the form of doubt, cynicism, and pressure to conform. It takes tremendous endurance to survive such resistance. In order to fight against the resistance, you’ll need more than passion and empathy. You’ll need to commit to suffering for the years required to push your idea to fruition. Not just a willingness to suffer, but a commitment.
Notes: It is a long road, a road of pain to build massive companies. Let’s not hide it. We will be doubted, challenged, fought.
Whatever you do, don’t fear tension and confrontation. You are a storyteller. Your job is to make history more interesting and relevant when retold than when it happened.
Notes: Your team needs energy transfusions, especially in the middle miles when circumstances feel dire and there is no end in sight. Acknowledge the trials and uncertainty you’re facing, followed by reiterating your plan of how to climb out, what you’re aiming to achieve, reminding your team why you’ve come together to do that, and then add your own enthusiasm and confidence. In the final moments of every meeting and communication, you need to reiterate purpose and leave people with the energy to achieve it.
Notes: Turn every milestone into a source of energy Celebrate more our customers Share often why the work of each Alaner is important, and what success looks like
Whenever I needed to force myself to take action that would be painful in the short term but was for the greater good, I would whisper to myself, “Scott, do your fucking job.” Leading a team through enduring times requires many “rip off the Band-Aid” moments. Nobody wants to inflict pain on their team, but quick and controlled pain is better than a drawn-out infection. If the cost of waiting exceeds the benefits of acting now, you have a job to do—DYFJ!
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Notes: When you’re anxious about your business, there is no easier quick-relief antidote than checking things. The problem is that you could spend all day checking things and fail to do anything to change things. I call it insecurity work—stuff that you do that has 1. no intended outcome, 2. does not move the ball forward in any way, and 3. is quick enough that you can do it unconsciously multiple times a day.
Insecurity work puts you at ease, but it doesn’t actually get anything done. The antidote is a combination of awareness, self-discipline, and delegation.
Notes: We have all been through it. It makes the difference between being efficient and being overwhelmed. For me, it was a process of trusting the system, putting the important things in my to-do so I don’t need to check now, because I know I will check at the right time.
Whenever I meet with a team that lacks clarity or feels stuck, their breakthrough often comes from a new question or problem to solve rather than a better answer to the original question. If the original question plaguing you is “Why aren’t people signing up for our product?” maybe the better question is “What kinds of people would benefit most from our product?” When you feel lost in ambiguity, ask a different question
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There are so many people in the world with ideas to transform industries and build iconic brands. But very few people can stay loyal to a strategy long enough for their vision to materialize. To allow strategy to unfold, you need to refactor your own expectations and measures of progress while developing a culture and structure that ensures your team has the patience to stick it out with you. “If we have a good quarter, it is because of the work we did three, four, five years ago, not the work we did this quarter.” There is a huge lag between great innovations and results. A new program takes a ton of refinement and optimization, as well as the natural passage of time, to spread and perform. Designing the structure of a project or company to foster patience is ultimately an effort to limit our natural tendency to obsess over measuring progress with traditional near-term measures. Patience doesn’t mean tolerating inaction or slower progress: It means allowing alternative forms of measuring the impact of action.
Despite how much we intellectually understand the importance of pursuing a strategy with patience, few of us are willing to pay the price of patience. We’ll spend a year working on a project and then begin to question it just weeks after launch rather than allow enough time to pass for an idea to become relevant or a brand to become recognizable. Celebrate persistence over time as much as the occasional short-term wins you have along the way. When I find myself debating a road map with a product team at Adobe, or making decisions about the technical architecture of a product, there is often an “easy option” that provides most of the desired functionality and a “best option” that is inevitably a step function more difficult and costly to achieve. If you want to be the industry leader, sometimes you need to take the difficult path. Be wary of the path of least resistance. The long game is the most difficult one to play and the most bountiful one to win.
Notes: “Active patience” is the most important thing. Stick to your strategy, be really active in terms of efforts, be patient with the results. Take the time to see if an idea becomes relevant, the time to tinker, to iterate. Moats are built because you do the very hard things We should celebrate persistence more!
So much of excellence is about just doing the work—even when it’s not yours to do. So much energy goes into directing blame and expressing disappointment rather than just taking initiative to tackle what you’re criticizing. Everyone has an opinion, but few people are willing to do something about it —especially if it falls outside of their formal job description. Across so many teams I’ve worked with, I’ve marveled at just how quickly an idea takes hold when someone proactively does the underlying work no one else clearly owned. There is rarely a scarcity of process or ideas but there is often a scarcity of people willing to work outside the lines. Don’t talk: do. Care indiscriminately.
Notes: Very much agreed. It makes a huge difference and I really, really value this. “The man in the arena” speech from Theodore Roosevelt is really about this
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Notes: 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. Inexperienced yet smart people with initiative will almost always exceed your expectations. Initiative is contagious, expertise is not.
Notes: Debates and disagreements are fruitful only if your colleagues are determined enough to ruthlessly fight it out with you, with one another, and without apathy. The more you challenge one another, the more you will uncover. So long as they share your mission, these instigators are your greatest protection from groupthink and harmful compromise. Learn to tolerate the people you struggle with. Cultivate your team’s immune system, and occasionally suppress it
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Just as teams must challenge conventional wisdom to build extraordinary products, the same goes for building extraordinary organizations. 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.
Notes: If not implemented properly, process slows down progress. It can be painful, especially as teams that grew up eschewing mandates mature. Nobody likes more obstacles to doing the real work. The conundrum of process is we all need some, but too much is lethal. The more aligned your team is, the less process you need. Install process for your team, not for you. A lot of wasteful and painful processes are born from anxiety. Spend more time on achieving alignment than imposing process.
Notes: I totally agree that when you have the right team, you need 10x less processes. When we need to add processes is when we need to review our talent density. Spend more time sharing context, repeating the story. Focus on building alignment.
If a picture is worth a thousand words, then a mock-up answers a thousand questions. Sharing a design, a series of samples, or a rough prototype quickly aligns people. Without it, much of a discussion is spent orienting a group around a concept and addressing basic questions and misunderstandings. 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.
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Call the difference between the big tasks and the little tasks “boulders” and “pebbles.” The boulders are hard to move up the hill, but they materially impact your project and differentiate you from others. Boulders could be a major new feature, a new architecture for your service, or writing the initial draft copy for your website. 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.
Notes: Spending more time on the hard problem is what makes a true difference I like 80% of boulders and 20% of pebbles. It is really hard as we all want to open slack, and answer quick stuff. We need a strong will to focus on the hard things.
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. Rather than passively surf the whims of people’s hesitations to take action, bring the conflict to the surface with questions like the following: “Let’s talk this out—what is the worst thing that will happen if we launch a bit early? Is scrambling a little bit after launch really worse than punting the project for additional months?” “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 decision is made.
Notes: Do not avoid talking about problems Understand what kind of conflicts make topics progress Issues are resolved by knowing what they are Care about your work!
Instead, look at what your competitors do, and ask yourself a series of questions: “Are their strategy and goals the same as mine?” “Is their tactic better?” If so, you should consider taking the same tactic yourself. 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.
Notes: We have our own strategy, and we should not emulate the one from competitors We can take strategic frameworks from other industries When someone has a good tactic, we should steal it. Always take a step-back on what the competition is doing and is it sustainable.
Those aspects that differentiate your product are your chance to create something valuable and warrant a disproportionate amount of investment. Speed through the generic stuff, but take the time you need to perfect the few things that you’re most proud of. Remember that customers don’t engage with functionality. They engage with experiences.
Notes: Decisions based on consensus typically end up with an ordinary outcome because by seeking to please everyone, you boil your options down to their lowest common denominator: whatever option is most familiar to the most people and therefore gets the least protest and the fastest support. As British author Aldous Huxley once observed, “The vast majority of human beings dislike and even actually dread all notions with which they are not familiar. Hence it comes about that at their first appearance innovators have generally been persecuted, and always derided as fools and madmen.” When working in a group, innovators must be willing to be the fool.
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Great products don’t stay simple by not evolving; they stay simple by continually improving their core value while removing features and paring back aspects that aren’t central to the core. One of my favorite tactics is to compare every new feature on your road map to the features that already exist. For example, if you would choose to create this new feature instead of something you’ve already done, consider killing the live feature.
Notes: Should we do more subtraction? How much does it apply in B2B? I think the goal is to have a very deep product that is very simple to navigate and discover. The UX should be very simple. It is a risk for us to focus only on power users.
‘If you had to keep 10 percent, which 10 percent would you keep, and if you had to, absolutely had to, cut 10 percent, which 10 percent would you cut?’
Notes: Having to explain your product is the least effective way to engage new users. The absolute best hook in the first mile of a user experience is doing things proactively for your customers. That means providing customers with templates to choose from and edit rather than explaining how to create a digital card from scratch.
Notes: How to make our members even more successful? Should we have more templates in our surveys? The pre-filled feature for journaling is exactly about this.
The key to breaking incrementalism and escaping your local maxima is to swap out your underlying assumptions. “Just because you have product-market fit doesn’t mean you’re going to keep product-market fit,” he explained. “That’s actually a pretty scary notion. The world changes and people change and society changes and culture changes and moorings change.”
Notes: “Just because you have product-market fit doesn’t mean you’re going to keep product-market fit”. World change, competition change. Always discuss the trade-off between iteration and thinking for the very long-term, what assumption we need to prove at which stage.
Notes: While all aspects of your product or service should be evaluated, the measures you use will vary. While the data suggests that some of these buzz-worthy features are not widely used after launch, they play an important role in advancing the field and getting customers excited about new releases.
Notes: What are our rocket’s spent boosters? I love this principle. What are our interest drivers? Alan Map is likely an interest driver. Do we have features only for a few important customers? Or to get new customers?
Priorities change, and the best leaders change with them. You need to be confident to be willing to change your plan. Being willing to change your mind means you are still permeable and willing to learn. Business plans are a standard part of building a new venture, but they should be approached as a thought process, not a map
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