PDF Summary:The Diary of a CEO, by Steven Bartlett

What if you could sit down with hundreds of the world's most successful people and ask them to teach you their greatest wisdom? One entrepreneur has done just that. In The Diary of a CEO, Steven Bartlett distills the business and life advice he’s gained from several years of podcast interviews, as well as his own extensive business experience. His tips are for anyone looking to make a difference in the world and live the most fulfilling, productive life possible.

In this guide, you’ll learn the five assets you need to maximize your impact on the world, how to turn stress into something exciting and energizing, and more. In our commentary, we’ll supplement Bartlett’s business advice with tips from books like Built to Last and The Lean Startup, and we’ll add to his life advice by consulting books like Outlive and Atomic Habits.

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Like Bartlett, Ries believes that the potential rewards of such experiments outweigh their sunk costs. That said, he also recommends ways to reduce the potential harm caused by internal startups gone wrong. For instance, any tests that internal startups conduct should only impact a limited number of the parent company’s customers. Furthermore, if at any point their experiments seriously threaten the parent company’s business, those experiments must be immediately shut down.

Tip #2: Focus on Tiny Upgrades

We’ve discussed how businesses that conduct frequent experiments often reap the reward of huge groundbreaking innovations, but Bartlett also contends that innovations don’t have to be big and groundbreaking to radically improve your business. Rather, a multitude of tiny upgrades can achieve big results over time. For example, an online marketplace may run thousands of small A/B tests to determine the effect of subtle design changes on user behavior. Over time, these tiny changes result in an irresistible website that gives the company a huge competitive advantage.

Bartlett insists that if you build your company’s culture around continuous tiny upgrades, eventually you’ll have a world-class business.

Likewise, Bartlett asserts that ignoring small details has the opposite effect: If you ignore little problems, their consequences will add up over time and cause major damage to your business. For example, a software company that dismisses every minor bug and user complaint as trivial will alienate its user base over time as the product becomes increasingly unusable.

Tiny Upgrades for Self-Improvement

In Atomic Habits, James Clear contends that tiny upgrades are also the key to self-improvement. By focusing on repeating one small healthy action at a time, you can turn this action into a consistent habit that requires minimal conscious effort to maintain. This allows you to continue improving yourself without draining your motivation or willpower. While these tiny upgrades may seem insignificant at first, their impact grows massively as you consistently apply them.

For example, if you eat a single serving of vegetables every day at lunch, this choice will become a habit, and it’ll be easier to start eating vegetables at breakfast and dinner, too. If you continue building these habits, you’ll eventually revolutionize your diet and feel much healthier.

Likewise, tiny oversights can accumulate into negative habits that hinder your progress. Consistent unhelpful actions, like leaving a few dishes in the sink or procrastinating on a quick task, can spiral into larger problems: habits of avoidance that significantly impede your self-improvement efforts.

Tiny Upgrades Are Motivating

Furthermore, Bartlett emphasizes that tiny upgrades serve as a powerful source of motivation for your team. As long as your employees feel like they’re successfully moving toward a goal, they’ll be motivated to keep going, even if progress is slow.

(Shortform note: Other experts support this idea: According to John Doerr in Measure What Matters, research shows making progress can be more motivating for workers than receiving a bonus, receiving public recognition, or even achieving the goal itself.)

Tip #3: Constantly Predict What Could Go Wrong

We’ve established that many companies fail because they overlook countless tiny flaws—but surprisingly, a good number of companies also fail because they overlook enormous flaws. According to Bartlett, people subconsciously push away thoughts and feelings about bad things that could happen because thinking about them is so unpleasant. This means that when you’re running a business, your first instinct would be to avoid thinking about potential ways your company could fail and ignore any evidence that it has major flaws.

(Shortform note: Subconsciously pushing away unpleasant thoughts and feelings is known as repression. Unfortunately, repression is a short-sighted strategy that typically causes greater long-term emotional distress. Additionally, some research indicates that chronic repression can even lead to physical symptoms such as high blood pressure, fatigue, and headaches.)

Bartlett recommends regularly conducting premortems to compensate for this bias toward denial. A premortem is a proactive analysis of a business strategy’s potential flaws—as opposed to a postmortem, which is an analysis you conduct after a strategy has already failed.

First, imagine in detail a future in which your strategy has failed. Then, come up with as many explanations as you can for why it failed. Finally, adjust your strategy to make this negative future less likely, and come up with backup plans to reduce the potential downsides of negative outcomes. The premortem is most effective when you walk many relevant team members through this process together, allowing them to contribute insights.

You Shouldn’t Try to Predict Everything

In The Dichotomy of Leadership, Jocko Willink and Leif Babin argue that although conducting premortems and planning for what could go wrong helps avert painful disasters, overplanning—attempting to prepare a detailed response for every possible setback—can also be harmful. Taking the time to predict everything that could go wrong will severely slow you down. At a certain point, this wasted time becomes more costly than it’s worth.

Additionally, overpreparing for unlikely events often causes its own problems. For example, Babin, a former Navy SEAL commander, discovered that when he assigned more soldiers than necessary to a task as part of a contingency plan, it endangered the mission—the team became more difficult to manage as it grew.

For these reasons, Willink and Babin recommend limiting yourself to contingency plans for three to four things most likely to go wrong, as well as a plan for your worst-case scenario.

Tip #4: Be Humble Enough to Hire People Better Than You

According to Bartlett, to build a successful business, you don’t need to master a vast range of skills. More than anything else, you need to be good at identifying, hiring, and retaining people with the skills you need. No matter how smart or capable you are, your business will be constrained by the limits of your knowledge, skills, and time. The only way to break through those constraints is by surrounding yourself with team members who shore up your weaknesses and expand your capabilities.

Many entrepreneurs make the mistake of overestimating the impact their skills and expertise have on whether their businesses succeed or fail. Consequently, they fail to invest enough effort in hiring the right people. Accept that you’re not as essential to your business’s success as you’d like to be, and focus your efforts on assembling the highest quality team you can. Additionally, make sure you create a working environment that allows them to do their best work.

Every Expert You Hire Saves You Time and Money

In Who Not How, Dan Sullivan argues that it’s not only impossible to learn and do everything necessary to build a successful business by yourself—it’s also a waste of time to do anything you’re not already an expert at. Hiring an expert saves you a significant amount of time that you’d otherwise spend painstakingly learning new skills, and you can use this extra time to improve your business in other ways.

Sullivan explains that although it’s inefficient to do everything yourself, many entrepreneurs fall into this trap—not because of pride, but because they’re hesitant to pay someone to do something they could do themselves for free. However, he contends that every dollar you spend on expert employees is an investment that kickstarts an ever-expanding cycle of growth. As long as you make the purpose of your business clear, your personnel will continue to optimize and improve whatever processes they’re engaged in, generating better results faster and further improving your business.

How to Manage Productive Teams

We’ve established that the success of your business rests in large part on your talented workers—but how do you nurture these talents and unlock your team’s full potential? Here are two of Bartlett’s tips on how to build a productive team culture and coach individual workers to do their best work.

Tip #1: Establish a Fanatical Culture, Then Transition to a Supportive Culture

Bartlett contends that organizational culture—the collective working habits and underlying philosophy of your team—determines the quality of your team’s work and, ultimately, your business’s success or failure. However, the ideal culture differs depending on what stage in its lifespan your business is in.

When launching a new business, encourage your core team to fanatically prioritize the company's success above all else. Intense devotion and single-minded focus are required to get a new business up and running. In this stage, treat your company like a cult: Make your employees feel like they’re all a part of the same special group that’s going to change the world. Position yourself as a visionary leader for whom failure is impossible so they can get excited to follow you.

(Shortform note: In Built to Last, Jim Collins and Jerry I. Porras also recommend establishing a “cult-like” company culture—not just at the beginning of a company’s lifespan, but in perpetuity. To make employees feel more like they’re a part of an exclusive, important group, create a unique vocabulary that only your company’s insiders understand. Additionally, Collins and Porras contend that you shouldn’t channel workers’ excitement toward yourself as a visionary leader. Rather, build up their passion for the company itself, and what it stands for. One way to do this is to highlight the importance of your company’s history and traditions when training new employees.)

Bartlett warns that although this kind of fanatical culture is effective at building momentum quickly, it’s impossible to maintain forever. People can only wholly devote their lives to a mission for so long before they get burnt out. For this reason, once your company is well-established, allow your culture to mature into one that’s more supportive of employees' long-term well-being and loyalty. Keep your team motivated and engaged over the course of years by giving them autonomy over their work and protecting them from excessive emotional stress—while ensuring that they’re still doing work they can be proud of.

Counterpoint: Prioritize Employee Well-Being From the Beginning

In It Doesn’t Have to Be Crazy at Work, business owners Jason Fried and David Heinemeier Hansson contend that it's crucial to establish a work culture that prioritizes employees’ long-term well-being from the beginning—and they’d likely argue that this is true even in the early stages of a startup.

They assert that most companies set ever-increasing revenue targets with the goal of achieving maximum growth at all costs. As a part of this process, companies accept investments and take out loans in an attempt to accelerate their growth as quickly as possible. However, this strategy puts unnecessary pressure on the team—if the company doesn’t hit its growth targets, it goes bankrupt. This pressure can cause employees to quickly burn out.

Fried and Hansson argue that instead, companies should pursue humbler goals: Be financially sustainable, deliver a great product or service, and gradually improve your business over time. Although your startup might not become the biggest company in the world, it can still become a great success—employees who aren’t overwhelmed can even be more productive.

Fried and Hansson’s strategy for supporting employees’ long-term well-being differs from Bartlett’s, too. Rather than emphasizing personal autonomy, they recommend providing generous benefits that directly support employees’ lives outside of work. For instance, they pay for their employees to take three weeks of vacation every year and subsidize personal education that has nothing to do with work, like cooking classes. Fried and Hansson state that when employees cultivate a fulfilling personal life, their overall quality of life improves, making them less likely to burn out on the job.

How to Shape Your Team’s Culture

Bartlett explains how to nurture your desired culture in your organization: Articulate the fundamental values that define your organization (at this stage), and ensure that they’re woven into every one of its operational protocols and routines. For instance, the CEO of a tech startup might adopt the mantra of "victory requires speed" and center the organization on rapid innovation. The company requires all meetings to be held standing up to ensure they’re as short and efficient as possible, and it crowns one employee every day as the “Momentum Maker” to recognize those who make the most rapid progress in a single day.

(Shortform note: In Excellence Wins, Horst Schulze contends that once you’ve articulated the values that define your organization and codified them into a set of protocols, you should require all teams to briefly meet and discuss one of them at the start of every work shift. This way, you ensure that employees understand the cultural values behind your rules and have them at the front of their minds every day.)

According to Bartlett, another way to shape your team’s culture is to identify employees who epitomize the culture you want to see and promote them to managerial positions so they can exert a stronger positive influence on other team members.

(Shortform note: In Radical Candor, Kim Scott agrees that managers have a strong influence over the culture of their team, and she adds that they need to be fully aware of what kind of influence they have. To learn this, managers can build open, honest relationships with their team members so those employees are unafraid to share candid feedback.)

Bartlett also recommends firing employees who are consistently unwilling to adapt to your desired culture. Although firing people is unpleasant, it’s necessary: Negative attitudes and habits spread easily, and if you don’t remove them, it’ll prevent many of your other employees from reaching their full potential.

(Shortform note: In No Rules Rules, Reed Hastings explains how Netflix takes a more proactive approach to maintaining an elite workplace culture. Netflix encourages managers to regularly assess whether they’d fight to keep an employee—and fire that employee if they wouldn’t. This does more than ensure that no negative attitudes or habits are poisoning the culture: It also ensures that there are only productive attitudes and habits, thus inspiring every employee to meet this high standard.)

Tip #2: Coach Every Individual Differently

Although the right culture can empower all your employees, it takes a more hands-on approach to maximize their individual potential. Bartlett states that every member of your team has unique personality quirks, motivations, and weaknesses. Thus, there’s no single coaching method that will inspire and motivate everyone in the same way. To be a great manager, you must know your team members at a deep, personal level and customize your management style to bring out their unique potential.

This kind of individualized management demands emotional intelligence more than anything else. Study what causes your team members to feel the way they do and discover ways to evoke positive, productive emotions.

For example, you may notice that one of your workers is remarkably efficient when given specific instructions, but they tend to get anxious when asked to engage in open-ended problem-solving. For this reason, you take extra time to break down complex projects into step-by-step tasks for them. This way, they feel confident that they’ll be able to do their work correctly and effectively.

Individualized Coaching Is Just One Management Style

In Primal Leadership, Daniel Goleman, Richard Boyatzis, and Annie McKee agree that emotional intelligence is necessary to be an effective manager. However, they argue that focusing on individualized coaching is just one option among many effective management styles.

For instance, a manager using the democratic style deeply involves their team members in the discussions that lead to major decisions. A manager using the commanding style provides strict directions in critical, high-stress situations. This style requires a high degree of empathy and emotional self-control to avoid intimidating team members.

According to the authors of Primal Leadership, the best managers know how to shift into any of these management styles, and they use whichever one would be most effective in a given situation. For example, a project manager might use a commanding style to ensure that everyone does what’s necessary to meet a tight deadline. However, after noticing that one of their team members seems overwhelmed, they might shift to a coaching style that provides individualized guidance and support.

How to Build an Irresistible Brand Image

Finally, Bartlett asserts that even the most well-run business will fail if consumers aren't excited about its offerings. Here are his tips for crafting a brand image that attracts attention and makes your product or service irresistible.

Tip #1: Create Value Through Presentation

Bartlett argues that the way you package and present your product or service can make a world of difference in how valuable consumers believe it is. People typically don't evaluate anything in a purely logical way—they use irrational mental shortcuts to determine how much they want something. This means that, often, small tweaks in presentation or design are enough to transform your brand image. For instance, a high-end vodka brand might exclusively sell their liquor in small bottles to make each drop seem more precious.

Present your product or service in a way that perfectly matches the idea of what a high-quality version should look like, and avoid adding anything that would detract from this narrative, even if it would technically make the product or service more valuable. For example, a high-end earbud brand might have discovered a way to make music sound crystal clear using extremely small, convenient earbuds. However, they choose to build their earbuds much larger because consumers assume that larger earbuds have better sound quality.

Tailor Your Presentation to Your Target Audience’s Worldview

Bartlett recommends modeling your product or service after the idea of “high quality,” but some argue that different groups have different ideas of “high quality.” In All Marketers Are Liars, Seth Godin contends that marketers find the most success when they align the presentation of their products or services with the worldview of their target audience. By “worldview,” Godin means the beliefs, values, and biases that define a particular group.

By appealing to a specific worldview, marketers can surround their product or service with a story that resonates with their customers and validates their beliefs. This approach helps marketers capture the attention of their target audience and communicate in a language they expect from the products and services they buy.

For example, a financial planning firm might target young internet-obsessed investors by calling their services "wealth hacking." This phrasing affirms their target audience’s beliefs that investing strategy should be approachable, innovative, and cool.

Tip #2: Stand Out From the Crowd

According to Bartlett, truly successful marketing does more than present a product or service as valuable—it’s so unusual and striking that it demands attention. People naturally get used to—and subconsciously ignore—the types of brands and marketing messages that they’ve repeatedly encountered in the past. This means that you need to find unique, attention-grabbing ways to advertise and present your brand.

Furthermore, Bartlett insists that the most engaging and shareable marketing messages are unusual in a way that’s impractical and ridiculous. Most companies rarely waste their marketing budgets on goofy messages, publicity stunts, or silly product features—so if you do, you’ll stand out. Ridiculous investments like this will make media outlets and consumers excited to talk about your brand online, giving you free word-of-mouth advertising.

For example, a car wash might enact a policy in which they’ll wash your car for free if you bring in a photo of you with a celebrity. They create a huge wall to display all these photos with a large banner that reads, “Friends of celebrities wash their cars here.” This memorable rule gets people talking about the car wash and reinforces the brand message that it’s a high-end, celebrity-worthy service.

Although unusual brands attract attention, your marketing shouldn’t be so unusual that it’s inconceivable. Generally, people prefer to engage with concepts that are somewhat recognizable, so your goal is to find the sweet spot between familiarity and novelty. Trends in marketing are always coming and going, so you need to be constantly ahead of the curve: Create marketing campaigns that are fresh yet understandable, and drop them before they become so commonplace that consumers ignore them.

Build Familiarity, Then Push for Sales

In Jab, Jab, Jab, Right Hook, Gary Vaynerchuk explains a social media-based marketing strategy helps brands strike a balance between familiarity and novelty. He recommends that branded social media accounts make two kinds of posts: “jabs” and “right hooks.” Jabs are pieces of content designed to build relationships with potential customers. They’re often entertaining, thought-provoking, or emotionally resonant—but crucially, they don't directly push for a sale. On the other hand, right hooks are posts with clear calls to action, designed to convert interest in a brand into sales.

For example, over the course of a week, a designer sneaker company on Instagram might post a series of retro pictures of the shoes major basketball stars were wearing at memorable games (jab). Then, they post a picture of their featured shoes for sale and offer a discount code for 20% off a customer’s first pair (right hook).

As in boxing, the effectiveness of a right hook knockout depends on the jabs that came before it. By consistently providing branded content that people find valuable or entertaining (jabs), you slowly get people familiar with your brand. This way, you leverage the human bias toward familiarity to make people more likely to buy something when you make a special offer (the right hook).

Since they’re not obligated to directly push for a sale, jabs can be more unusual than the average advertisement, making them more effective at cutting through the noise and grabbing attention. For instance, the Wendy’s account on X (formerly Twitter) replied to a user who asked “What’s the best thing to get at McDonald’s?” by simply saying “A refund”—entertaining users while making the Wendy’s brand more endearing. Although they’re not as high-profile as the ridiculous publicity stunts that Bartlett describes, jabs are similar in that they lack obvious business utility, making them more appealing in an environment where consumers are increasingly wary of advertising.