The 7 Books Every CEO Must Read in 2026 to Lead in a World of Risk, AI, and Rapid Change
As we head into a new year and wrap up annual planning season, every CEO is thinking about AI, talent, and economic uncertainty.
But those are table stakes. If you want to set yourself and your company apart, you need to add some new ideas to your 2026 playbook.
How about a little game theory? Or sailing instruction? Restaurant management? The latest in biochemistry? The San Francisco 49ers?
To spark some outside-the-box thinking, we recommend CEOs add these seven books to their reading lists — once they’ve finished their annual reread of Making BIG Happen, of course.
1. Against the Gods: The Remarkable Story of Risk by Peter L. Bernstein
This comprehensive history of man’s efforts to understand risk explains how humanity moved from feeling at the mercy of fate to mastering and improving our odds.
Why Now? From geopolitical instability and supply chain fragility to AI-driven market disruption and emerging competitors, CEOs will face many volatile variables next year. Instead of trying to avoid risk, leaders need to learn that risk is actually a choice — and an opportunity.
Key Ideas:
- Separate Probability from Uncertainty: There’s a BIG difference between a calculated risk and a blind gamble.
- Account for the Human Element: Separate unpredictable human behavior from hard data so that you can manage both people and processes better.
- Risk is an Engine: Taking the right chances the right way can lead to innovation and growth.
“We pour in data from the past to fuel the decision-making mechanisms created by our models, be they linear or nonlinear. But therein lies the logician’s trap: past data from real life constitute a sequence of events rather than a set of independent observations, which is what the laws of probability demand. It is in those outliers and imperfections that the wildness lurks.”
2. The Score Takes Care of Itself: My Philosophy of Leadership by Bill Walsh
Legendary coach Bill Walsh transformed the San Francisco 49ers into a dynasty. But he didn’t start by obsessing over the Super Bowl — he started with a three-page memo on how receptionists should answer the phone. In Walsh’s classic manifesto on performance, every detail matters.
Why Now? CEOs who don’t have enough data are in the same boat as CEOs who have too much: the scoreboard can be paralyzing. Walsh coaches leaders to shift their emphasis from scorekeeping to process. The better your inputs, the more desirable your outputs will be.
Key Ideas:
- Standardize Performance: Define exactly what excellence looks like for every role and task in your organization, no matter how small.
- Success is a Disease: The most dangerous moment for any team is the first game after a BIG win. Avoid complacency by continually aiming higher.
- Teach, Don’t Demand: The best leaders inspire their teams to grow by focusing on improvement, not punishment.
“The culture precedes positive results. It doesn’t get tacked on as an afterthought on your way to the victory stand. Champions behave like champions before they’re champions; they have a winning standard of performance before they are winners.”
3. Sailing to the Edge of Time by John Kretschmer
A world-famous sailor recounts crossing oceans, weathering storms, and contemplating what it all means while alone on the waves. This memoir can reawaken the sense of wonder and the broader perspective CEOs often lose in the hustle and bustle of running a business.
Why Now? Most CEOs are overoptimized, overscheduled, and mentally exhausted. As a result, it’s easy to forget that business, and life, are about meaning and not metrics. Kretschmer is a philosopher with a sailing tiller in his hand, and his experiences will help CEOs connect their companies to a higher, more rewarding purpose than pure profit.
Key Ideas:
- Embrace Solitude: Planning is for the boardroom; dreaming is for those moments of quiet when leaders can be alone with their thoughts and goals.
- Calm the Storm: Great sailors learn the difference between a challenging situation and a dangerous one. It takes a different skillset and mindset to navigate through both.
- Live in the Moment: Shift your view of time from a resource you spend to a medium you experience.
“The very idea that my time could be owned by someone else, monitored by a clock, and traded not for freedom but for money struck me as lunacy. Where did happiness factor in, and what about the desire for a meaningful life defined not by your possessions but by your experiences?”
4. Unreasonable Hospitality by Will Guidara
Will Guidara took Eleven Madison Park from a decent brasserie to the top restaurant in the world with bespoke service that elevated every meal into a memorable experience.
Why Now? AI can optimize processes and answer FAQs, but it cannot make your customers feel special. As more and more businesses automate their customer experience, five-star service is a luxury that folks in both lanes of the two-speed economy will be willing to pay for.
Key Ideas:
- One Size Fits One: Standardize quality but personalize your products and services.
- The Rule of 95/5: Manage 95% of your business down to the penny; spend the last 5% on the extras that create emotional impact and build brand loyalty.
- Service is Culture: Your team members should treat each other with the same care that they give to customers.
“‘Black and white’ means you’re doing your job with competence and efficiency; ‘color’ means you make people feel great about the job you’re doing for them. Getting the right plate to the right person at the right table is service. But genuinely engaging with the person you’re serving, so you can make an authentic connection — that’s hospitality.”
5. Whoever Tells the Best Story Wins by Annette Simmons
Facts and figures are forgettable. Simmons explains how a good story can bypass skepticism and land directly in the listener’s heart.
Why Now? “Data” may be the buzzword of the moment, but stakeholders inside and outside of your company are craving a full story they can believe in. A clear, compelling narrative is the only way to cut through the white noise on your media channels, reach people, and align your team on a shared vision.
Key Ideas:
- Connection Before Content: Good stories establish trust before they try to convey information — or make a sale.
- Tell Your “My Why” Story: Connect your team and customers to your mission and values and they’ll follow wherever you point.
- Reframe the Future: In these uncertain times, a story that’s positive and hopeful about the future will resonate emotionally and rally people around your company.
“Most of us in business are conditioned to believe that business communication must be clear, rational, and objective. If that is true, there is no place for emotion or personal connection. Sharing a personal story, telling a story that makes a complex idea simple, or transforming an implementation plan into a living breathing future — that’s the secret to motivation. People float in an ocean of data and disconnected facts that leave them feeling often overwhelmed and suspicious of choices. In this ocean of choice, a meaningful story is like a life preserver you offer to grab onto something meaningful: a trace of humanity in a world of facts.”
6. The Master and His Emissary by Ian McGilchrist
McGilchrist argues that Western society has become dangerously dominated by the left brain (the “Emissary,” focused on detail, categorization, and utility) at the expense of the right brain (the “Master,” focused on the whole, context, and meaning). Restoring balance between how we think — and lead — is essential to managing our rapidly changing world.
Why Now? As AI increasingly automates the Emissary’s strengths — analysis, categorization, optimization — a CEO’s comparative advantage falls squarely into the Master’s domain. Refine your vision, storytelling, intuition, moral judgment, and holistic thinking to set your company apart.
Key Ideas:
- Put Context over Calculation: AI can provide words and numbers, but the CEO has to imbue them with meaning.
- See the Whole: Great companies see the whole by embracing nuance, ambiguity, and lived reality instead of collapsing everything into dashboards, metrics, and abstractions.
- Redefine Intuition: Look for opportunities in high-level patterns and trends rather than just “going with your gut.”
“Our talent for division, for seeing the parts, is of staggering importance –- second only to our capacity to transcend it, in order to see the whole. These gifts of the left hemisphere have helped us achieve nothing less than civilisation itself, with all that that means. Even if we could abandon them, which of course we can’t, we would be fools to do so, and would come off infinitely the poorer. There are siren voices that call us to do exactly that, certainly to abandon clarity and precision (which, in any case, importantly depend on both hemispheres), and I want to emphasize that I am passionately opposed to them. We need the ability to make fine discriminations, and to use reason appropriately. But these contributions need to be made in the service of something else, that only the right hemisphere can bring. Alone they are destructive. And right now they may be bringing us close to forfeiting the civilisation they helped to create.”
7. Lifespan: Why We Age—and Why We Don’t Have To by David Sinclair
Harvard geneticist David Sinclair challenges the view that aging is inevitable. He believes aging is really just a symptom of the body losing information and discusses science-backed protocols to slow, stop, and even reverse the process.
Why Now? You’re already exhausted. But the leadership demands of 2026 will require the stamina of an elite athlete. And if work demands all of your available energy, then you won’t have enough left over for your loved ones, or yourself. Sinclair’s book is a CEO performance manual with insights on improving executive function, sharpening mental clarity, building energy and stress tolerance, and regulating emotions with intention and intelligence.
Key Ideas:
- Embrace “Good” Stress: Exercise, intermittent fasting, and cold plunges can activate your body’s survival circuits and boost resilience.
- Longevity is Strategy: If you want to live longer, view your personal health span as a critical asset you need to manage.
- Numbers Don’t Lie: Take your biometrics as seriously as your company’s KPIs.
“This might be the least considered societal advantage of prolonged vitality, and it might just be the greatest advantage of all. Perhaps when we’re not all so afraid of the ticking clock, we’ll slow down, we’ll take a breath, we’ll be stoic Samaritans. I would like to emphasize the word ‘perhaps,’ here. I will be the first to say that this thesis is supposition more than science. But the small-sample Princeton experiment both followed and portended a lot of other research demonstrating that humans are a lot more humane when they’ve got more time. All of the studies, though, take stock of how people behave when they have a few more minutes, or perhaps a few more hours, to spare. What would happen if we had a few more years? A few more decades? A few more centuries?”
About CEO Coaching International
CEO Coaching International works with CEOs and their leadership teams to achieve extraordinary results quarter after quarter, year after year. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, CEO Coaching International has coached more than 1,000 CEOs and entrepreneurs in more than 60 countries and 45 industries. The coaches at CEO Coaching International are former CEOs, presidents, or executives who have made BIG happen. The firm’s coaches have led double-digit sales and profit growth in businesses ranging in size from startups to over $10 billion, and many are founders that have led their companies through successful eight, nine, and ten-figure exits. Companies working with CEO Coaching International for two years or more have experienced an average EBITDA CAGR of 67.8% during their time as a client, nearly four times the U.S. average and a revenue CAGR of 25.5%, more than twice the U.S. average.
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