Note: While reading a book whenever I come across something interesting, I highlight it on my Kindle. Later I turn those highlights into a blogpost. It is not a complete summary of the book. These are my notes which I intend to go back to later. Let’s start!

Despite the circumstances and solemn sense of many of these meetings, David had a way of leaving every meeting on a high note. He would acknowledge the challenges before us while reminding each team why their work was important and what success would eventually look like. Even after painful meetings that lasted multiple hours without any sense of closure, David still managed to bring it together at the end in a way where we all left with energy—something along the lines of, “Hey, I know this is rough and we’ve got some serious work to do, but I also know we’ve got a good plan and the right people,” and adding something funny and uplifting at the end

Your job is to be an energy giver rather than taker, which is common among founders and leaders I admire.

The common theme across interactions with Jon is that he’s all-in, all the time. When Dunkin’ Donuts became a big Cheddar client, Jon started wearing Dunkin’ apparel, catering every meeting with Dunkin’ Donuts and coffee, and sharing weekend shots of his family at Dunkin’ on Instagram. What better way to infuse energy into a partnership and send a clear message to current and prospective clients that Cheddar values loyalty and service? He turns every milestone into a source of energy rather than a celebration

A friend who worked for Google cofounder and CEO Larry Page told me that when teams presented product and business goals to Larry, he would often reply, “What would it take to achieve 100x of what you’re proposing?” This was totally unrealistic, of course. Such questions would throw teams off their tracks, but the notion of aspiring for an entirely different magnitude of impact had some important side effects. First, whatever doubts teams came in with suddenly paled in comparison to the new concern. Second, teams were forced to question their core assumptions and untether themselves from reality’s gravity

Avoid insecurity work. Insecurity work—stuff that you do that has no intended outcome, does not move the ball forward in any way, and 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.

When you spend 30 minutes going down a rabbit hole to answer a particular question, be sure to ask yourself, “Why is this question important and how is the answer actionable?” If the answer is just self-assuring but not actionable, it is likely insecurity work.

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. When making a decision with limited time and resources (and stress), we’re liable to accept the original premise and charge ahead to create new products or features without even asking questions—or questioning the problem we’re trying to solve in the first place.

Whether learning about the transportation industry or oncology and urgent health care, Bill will explore an interest for many months or years without concern for when—or even if—the right investment opportunity will present itself. He’s not racing toward a transaction against a clock; he’s digging to learn.

Ben breaks up every period of his company into chapters, each with a beginning, goal, reflection period, and reward. 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

It 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). But interfering with the order of operations of those around you has negative consequences, even if you think your initiative will save time and effort in the long run. People incorporate process into their work as a patch for their own misalignments, and to override such mechanisms without considering why they are there is problematic.

The best leaders of productive teams are constantly devising new and clever ways to get us to act. This could come in the form of a graphic representation of milestones and deadlines hung on walls, a communications campaign that repeats goals and the progress to date, or in the form of pithy time-bound declarations, like Pinterest’s “Year of Going Global,” which pushed every team across the company to reprioritize efforts to internationalize the business, or Uber’s “Year of the Driver,” which they rolled out when they realized they had fallen behind on developing tools and better policies for drivers on their platform.

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

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.

Just a quick reminder: Shorter emails get faster response times. Fewer words go further (and are listened to more intently). Standing meetings (where your knees get weak) prioritize the point. The less preamble, the more focused your team will be on your message. Most attention spans don’t even make it to the end. Start with your point; don’t end with it

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. Boulders could be a major new feature, a new architecture for your service, or writing the initial draft copy for your website. By contrast, pebbles are the innumerable little tweaks and changes you could quickly make that are rarely differentiating. 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. Even though we know that time is best spent on the big and important challenges, we’re still drawn to the quick returns. Resist

Former CEO of American Express, Ken Chenault, once shared what he considers one of the secrets to a fast career progression and reputation as an innovator in a large bureaucracy. “I would make my bosses make decisions,” he said. “You can’t just sit around and let people think about stuff, you must make them make decisions.”

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.

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. Rather than passively surf the whims of people’s hesitations to take action, bring the conflict to the surface with questions

Every product or service in your life either helps you spend time or save time.

For extraordinary outcomes, seek conviction in your work and build teams that value conviction over consensus

Great teams implement change when it’s still uncomfortable to do so, ahead of the realized need. Don’t give those resistant to change false hope for things staying the same; when a decision is made, declare the implications and chop off the rearview mirror.

As I reflect on the new products that have improved my life the most over the years, they ultimately removed a daily friction. Optimizing the product you’re making is ultimately about making it more human friendly and accommodating to natural human tendencies.

Here’s a quick exercise. First, make a list of the key characteristics and values of the major players in your industry. (If you’re a freelancer, this could be other people your clients consider hiring. If you’re a start-up, it could be the industry incumbents or your competition.) Perhaps they can offer a cheaper price to their clients, a focus on customer service, the speed of delivery, or the variety of different services offered. These are the factors that customers and clients weigh when determining who to work with. Now, make the same list for yourself and your business, but focus on the things you want to be known for. Perhaps you want people talking about the quality of your work, but you don’t mind if it takes a little longer or is more expensive. Or perhaps you want to be the go-to provider for last-minute projects and refuse to take on larger projects that would compromise your flexibility. Conscious trade-offs are a competitive advantage when the result is dedicating more focus and energy to what you’re best at. This exercise should reveal some industry-wide values that you don’t subscribe to and others you aspire to be known for. The former is a group of things you can be bad at, so long as you outperform on the values you hold dear. Of course, it is important to identify and address your weaknesses. But spectacular achievements are ultimately the result of doing something different exceptionally well.

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. The earliest users of a new product tend to be more visionary and tolerant of friction than later users. Over time, you will need to remove the friction, in the form of killing or reducing parts of your offering, to keep growing. When I compare Behance’s network today to the one we had six years ago, I am struck by how much simpler the product is. We eliminated our “Tip Exchange” feature, our “Groups” feature, the ability to customize the colors of your Behance portfolio, and countless other features and experiments that didn’t serve the core experience. A small number of customers complained each time we reduced our offering, but a much larger segment of customers became more engaged as a result. The simpler our product became, the more it resonated with people. When we did add a feature that withstood the test of time, it did so by being essential rather than novel. The creative process is a little dreaming followed by endless editing—but the tendency to edit does not come naturally to creative minds. On the contrary, the discipline to cut and refine your ideas can feel demoralizing—but this is about the customers, not your creative genius. The paradox of product success is that when you focus on pleasing your most engaged users, you stop engaging new ones. The sad reality—and the opportunity for start-ups—is that most established products take their large user bases for granted and fail to maintain simplicity over time. In the introduction to this section, I outlined the “product life cycle” in which users flock to a different simple product after an existing product takes them for granted and adds unnecessary complexity. Products that retain their greatness over time tend to hold simplicity as a core design tenet. As a sweetgreen board member, I always admired the way our cofounders Jonathan, Nic, and Nate held on to their original values regarding simplicity, initially forced on them by circumstance, as the company grew along with the temptation to expand the offering. As Nate explains it, “We were lucky with the limitations of our first space, which was only five hundred square feet. We always knew we wanted to be really good at one thing, and the companies we admired were those types of companies. We talked about that, but then what forced the discipline was the space itself. In later years when we had more space, it was like, ‘Well, should we do a retail store? Should we add this, that, smoothies?’ These are all things that we can convince ourselves fit into the core, but that first restaurant demonstrated that they weren’t necessary and the brand was strong without it. We couldn’t do anything else, so I think it was a blessing in a way.” The original constraints that forced simplicity became a core value rather than a hindrance.

Why is it so hard to keep a product simple? A big part of the problem is that you become intimately familiar with your “power users,” the small number of customers who use your product the most. This group of customers is also often referred to as the “vocal minority.” Power users have so much to say about the product you’re responsible for, and as a result, you will start to consider their complaints and requests. If only to feel like you’re doing your job, you’ll explore solutions to the problems they voice instead of focusing on the opportunities to engage the customers you have yet to reach. In the process, your prioritization and judgment is liable to be taken hostage by the vocal minority, whose desires stem from a deep relationship with your product, and you fail to take your newest customers into consideration. You can defy this outcome only by devising ways to maintain simplicity. In the world of digital products, 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. Forcing yourself to have a “one feature in, one feature out” guideline will help you develop your product with a bias toward simplicity. While simplicity benefits your newest customers and the majority of your current customers, it also benefits your own process to grow your product and solve problems as they arise. The more dynamic your offering is, the harder it is to diagnose what’s working and why. But with fewer moving parts, you’ll have a better understanding of which levers to pull at which times for which outcomes. Your intuition is sharper when your product is simpler. For the sake of your own focus and ability to make great product decisions, reduce and add to your product in parallel.

The flaw with pursuing and preserving many options is that doing so stunts your progress in any particular direction. When your energy is split, so is your speed and focus, and the resources around you are harder to tap when your narrative is too broad. Instead of pitching one cohesive vision to your team, you confuse them with two (or more!). Instead of one fifteen-second elevator pitch to a potential investor, you muddle your story with a hybrid. Instead of your friends and professional network all spreading the word about the single thing you hope to achieve, they will be sending different messages. But the greatest cost of trying to sustain multiple initiatives is having too little thrust behind one goal. When a goal is simple and singular, every realization builds upon the one before it. 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.

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.

The only time you should force new behaviors or terminology is when they enable a unique and important value in your product. For example, Snapchat was the first social network that would open on the camera view when you clicked on the app instead of other competitive products like Instagram and Facebook that open on a feed of others’ content. This behavior struck new users as foreign, but it retrained users for an entirely different kind of social experience. Snapchat aspired to be more of a camera than an app, and launching the product in camera mode sent a strong and differentiating message to its users that helped distinguish Snapchat from other social apps—as well as the kind of content created with it

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.

Having a tight deadline and an overwhelming list of tasks to achieve can help keep you moving and stop perseverating. Rather than seeking more options, remind yourself that you make progress only once a decision is made, and you can always backtrack or adjust as you learn along the way. Don’t fall into the vortex of navel-gazing; keep moving.

The most effective designers are always solving a specific problem and seem to do so more by removing than adding.

Reduce elements—and any step requiring decisions—whenever you can. Fewer options, shorter copy, and simpler steps will always bring your product to a better place. In the moment, this will feel counterintuitive—you’ll assume that progress means new features and a visual evolution of your product. But over time, you’ll learn that the incremental reductions and refinements allow customers to flow through the experience with more ease than most new features or additional copy ever could.

The first mile of your customer’s experience using your product cannot be the last mile of your experience building the product.

The absolute best hook in the first mile of a user experience is doing things proactively for your customers. Once you help them feel successful and proud, your customers will engage more deeply and take the time to learn and unlock the greater potential of what you’ve created.

For digital applications such as Paperless Post, an online tool to create and send digital party invitations and birthday cards, that means providing customers with templates to choose from and edit rather than explaining how to create a digital card from scratch. For photography-editing applications like Instagram or Google’s and Apple’s photo products, that means providing smart filters that apply a sequence of effects to an image all at once rather than forcing customers to learn how to use different tools for contrast, brightness, and sharpness. In most of these cases, full personalization is available—but it’s not the first option.

The key to breaking incrementalism and escaping your local maxima is to swap out your underlying assumptions. For example, if your product was founded in the age of social media and mobile apps, what assumptions did you have then that you would now question as voice-activated devices enter our homes and augmented reality transforms our mobile devices?

When it’s the right time to make a bold move in product strategy, make a list of the core assumptions your product or service is based on. Many tech companies that spawned early in the internet era have had to reinvent themselves.

Strong denial is a signal for a hard truth.

In many ways, Behance was born out of a sense of frustration with the creative industry and our friends struggling to make a living. Our narrative acted as a compass for us, making it clearer which features we would develop (ones that boosted productivity and attribution) and which features we would not consider (ones that boosted creativity or marginalized attribution). Every product and marketing decision must fit the narrative.

While you’ll want to make every part of your product better, there is always a specific area of your product that needs your team’s energy the most. It may be a feature that has a disproportionate impact on your customer’s experience, or a potential single point of failure that could kill the whole product. When prioritizing tasks, focus your team on levers that have a disproportionate impact on your odds of surviving and succeeding.

Product development is typically driven by customer needs and nearly all features of a product are what I’ve come to call engagement drivers, intended to drive customer engagement of some kind. Such features can be measured by how often they are used or, when needed, how well they perform

On the contrary, the features that excite us most about a new product are often the most novel features that aren’t necessarily practical. I call these features interest drivers because their intention is not to spur ongoing product engagement or even be actively used, but rather to pique interest. 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. The true engagement drivers for every new version, whose importance can be measured in traditional ways, are the things that just make the product faster and easier to use on an everyday basis. But incremental improvements aren’t sexy and don’t make headlines, and prospective customers need reasons to get excited. When you’re launching new features, you need both interest and engagement drivers working in tandem. As you measure your product’s success, determine what every feature is intended to achieve and measure it accordingly. As you observe how customers use your product, you may be tempted to remove interest drivers, like HBO GO’s Game of Thrones integrations or a cool Photoshop feature, when you notice that they aren’t being used as much as you’d hope. But be sure to define the purpose of every feature in your product before determining its fate. Is it to strengthen engagement, appease a very small set of important customers, or get new customers in the door? Features with a different purpose require a different measure.

Loewenstein says that curiosity proceeds in two basic steps: First, a situation reveals a painful gap in our knowledge (like a BuzzFeed headline), and then we feel an urge to fill this gap and ease that pain (we click on it)

Ambiguous intrigue has a way of garnering interest better than any product description or list of features ever will. I call this force the “magic” of engagement. It’s an illusion, concocted to enchant your prospective audience and break through their rational selves.

The greatest brands were developed by playing at the far end of the spectrum and not trying to be everything to everyone. Playing to the middle makes you weak. You’ll never be an industry leader if you give up your edge to appeal to a broader audience. As you manage your brand and contemplate your own evolution, hold on to what makes you distinctive. Don’t compromise your specialty just to please your market—because if you do, it might not be there much longer.

Like Tim, we should all make a few bold bets early in our career to do something first and redefine a category. But throughout our careers, we should challenge ourselves to say yes only to things that bring our skills and network to a new level. Our natural drive to say yes to as much as possible, if only for optionality, may help us in the beginning of our careers but hurts us later on.

Vetting the true value of what you are afraid to lose is the first step to letting it go. Value is best measured by the resources you’d be willing to spend to do it again, knowing all that you know now.

The teams I admire most boil their business down to one or two of these core metrics that they believe represent progress in everything they need to achieve in a given year.

Sound judgment, achieved through aggressive truth seeking, is your most differentiating and deterministic trait.

Naivety yields an openness not yet tainted by—or bound to—the past.

The nonscalable artistic elements of a product keep it from becoming a bland commodity.

True innovators value art up front and compete against incumbents through the art of business—the stuff that doesn’t intuitively scale.

The beginning stages of a business are more art than science. You must try to solve problems with new ideas that will feel strange and are in no way economical. You must run manual experiments, spend endless amounts of your own time with customers, and tinker until you find something special. Give your customers something precious, something that cannot be easily scaled, automated, or commoditized. The greatest innovations in an industry are strange and artlike before they become the new standard. Do things that your competitors and incumbents wouldn’t even think of doing for lack of financial reward. Only through these explorations will you discover the key differentiator—the art—that surprises customers and builds a remarkable product and brand