Chief Joy Officer

When was the last time you felt genuine joy at work? In Chief Joy Officer, Richard Sheridan challenges the idea that business success must come at the cost of human happiness. He argues passionately that joy is not a luxury—it’s a necessity for thriving organizations. For Sheridan, joy begins when leaders let go of fear-based management, put people before profits, and design workplaces where service, purpose, and human connection drive results.

Sheridan’s central claim is that leadership built on joy beats leadership built on fear. He contends that most leaders today, despite their good intentions, still operate under systems designed to control and intimidate—hierarchies, policies, and micromanagement rooted in mistrust. Joyful leadership, in contrast, fosters autonomy, empathy, and shared purpose. Joy, he insists, is deeper than happiness—it’s the lasting satisfaction of doing meaningful work that serves others.

The Problem: Fear-Based Organizations

Sheridan begins with a stark truth: most workplaces are built on fear. Fear of losing status. Fear of making mistakes. Fear of your boss’s reaction. He recounts his own burnout years at Interface Systems, where endless meetings, hero-worship, and chaotic product launches led him to dread going to the office. When his young daughter observed that no one could make a decision without him, he realized he had become the bottleneck. True leadership, he saw, isn’t about being indispensable—it’s about making others fully capable.

The Shift: From Fear to Joy

Turning fear into joy meant reinventing his workplace. Sheridan launched the first experiments at the “Java Factory,” where programmers worked openly in pairs, shared decisions, and eliminated titles. It was messy at first, but culture replaced control, and collaboration replaced hierarchy. This approach evolved into Menlo Innovations—a company built around joyful leadership. There are no private offices, no performance reviews, and no bosses in the traditional sense. Teams choose who to hire, and feedback flows daily, not annually.

Menlo’s mission, Sheridan explains, is to “end human suffering as it relates to technology.” Every system in the company—from pair programming to open-book finances—exists to support that purpose. Sheridan compares this to Peter Senge’s concept of the learning organization: a culture grounded in continuous growth and shared accountability rather than fear and blame.

The Foundation: Values and Authenticity

Joyful leadership starts with deeply held beliefs. Drawing on Gandhi’s idea that beliefs become thoughts, thoughts become actions, and actions become destiny, Sheridan lays out Menlo’s three guiding principles: create positive human impact, act with authenticity and integrity, and express care, hope, love, and joy. These are not marketing slogans—they are used daily to guide decisions. Leaders are expected to model these principles in their behavior, not announce them from the stage.

The Practice: Joy Is Action, Not Abstraction

Throughout Chief Joy Officer, Sheridan draws on stories—from CEO missteps to canoe trips with his father—to show that joy is inherently practical. He introduces practices like “Extreme Interviews” where candidates must help their partner succeed, and “Feedback Lunches” where peers guide each other’s growth. He encourages leaders to hand off control, clean their own offices, and turn up the lights themselves—acts that symbolize stewardship, humility, and service.

Most revealing, Sheridan describes how optimism and vulnerability sustain joy. When business dipped at Menlo in 2016, he didn’t hide the numbers—he shared them with the whole company. This radical transparency replaced panic with problem-solving and bonded the team. “Fear doesn’t make bad news go away,” his office posters remind employees. “Fear makes bad news go into hiding.”

The Why: Joy Creates Sustainable Success

The book ends by reaffirming that joy is not a soft concept—it’s a strategic advantage. Research from leaders like Shawn Achor (author of The Happiness Advantage) and Bob Quinn at the University of Michigan supports Sheridan’s claim that positive organizations outperform fearful ones. Optimism, service, learning, and storytelling create environments where people grow rather than retreat. Sheridan’s message is ultimately moral as well as practical: leaders must care for their people, teach others to lead, and leave their campsite—this world—better than they found it. That is the legacy of a true Chief Joy Officer.

Sheridan opens his first section on leadership values with authenticity—the cornerstone of joyful leadership. He asks every leader to confront the mask they wear at work. Too often, leaders show confidence while hiding fear and exhaustion. In a memorable story from Ele’s Place, a grief center where children decorate masks with their public and private emotions, Sheridan draws a parallel: leaders, like those children, display one side to the world and conceal the other.

The Courage to Be Real

True leadership, Sheridan insists, means revealing both sides of the mask. When employees show up afraid to admit uncertainty, culture becomes deceitful. Sheridan shares how transparency saved one of his team’s relationships: when a developer undergoing surgery spoke openly about his fear, a colleague embraced him—literally. Vulnerability builds bonds stronger than policy ever could.

Bringing Your Whole Self to Work

Authenticity also means merging life and work, not separating them with corporate pretense. Menlo’s “babies-at-work” policy emerged from this belief. When an employee mother lacked daycare, Sheridan encouraged her to bring her baby to the office. Within months, the space was filled with laughing infants and productive parents. The fear of “lost productivity” melted away—joy replaced anxiety.

Relationships and Trust Over Fear

Sheridan argues that the antidote to fear is connection. At Menlo, employees work in pairs, switching partners weekly. This forces collaboration and dismantles isolation. “Relationships can only be built by spending time together,” he writes. Unlike companies obsessed with remote oversight and metrics, Menlo prioritizes physical proximity and constant communication—face-to-face, not email-to-email. The result? Trust replaces fear, and authenticity flourishes.

Seeing Yourself Through Others’ Eyes

Finally, Sheridan introduces the University of Michigan’s “Reflected Best Self” exercise—a structured way for leaders to see what others value in them. Participants ask colleagues to describe moments when they were at their best, then synthesize those stories into self-portraits. The emotional impact, Sheridan says, can be transformative. Tears often flow as people realize that they are enough. Authenticity begins when leaders stop pretending to be perfect and start believing they are worthy just as they are.

After authenticity comes humility and love—two entwined virtues that define Sheridan’s human-centered leadership. He explains humility through an embarrassing moment with two team members, Tracy and Matt. When Matt admitted he didn’t know something about a project, Sheridan criticized him—under a poster that read “It’s OK to say I don’t know.” Realizing his misstep that night, he apologized publicly the next morning. Matt simply responded, “I forgive you.” That simple act taught him what humility feels like in practice.

The Power of Servant Leadership

Sheridan invokes Simon Sinek’s idea from Leaders Eat Last: true leaders serve, not rule. Humility means cleaning the dishwashers, answering phones, and seeing every task as noble. He describes his morning ritual—turning on the lights and washing cups in the Menlo office—as a way to remain grounded. Servant leadership, Sheridan says, is not weakness; it’s strength expressed through responsibility for others.

Love Wins Every Time

Sheridan then extends humility into love, echoing Buscaglia’s and Corinthians’ teachings: “Love is patient, love is kind.” Through dozens of anecdotes—mentoring younger employees, comforting sick colleagues, or welcoming babies—he shows that business runs best on compassion, not competition. In one anecdote, he recalls firing a young employee decades earlier. The man later approached him to say that conversation changed his life. Even hard decisions, Sheridan concludes, can be delivered with care, dignity, and kindness.

Rejecting Pride and Envy

Menlo’s structure resists the poison of ego. There are no corner offices or unequal bonuses—all profit shares are equal in dollar amount. Collapsing hierarchy suppresses pride and envy, focusing attention on collective achievement. For Sheridan, humility is practical: “Hire people with A grades in kindergarten, not MIT.” Children who know how to share are destined to become leaders who care.

Sheridan claims optimism is not naïveté—it’s courage in motion. His story of Menlo’s downturn in 2016 proves it. When revenue plummeted, he didn’t hide the truth; he shared every number with his team through open-book management. Transparency transformed fear into accountability, and soon optimism—not denial—pushed the company to rebound. Sheridan encapsulates this mindset in a poster: “Fear doesn’t make bad news go away; fear makes bad news go into hiding.”

Action Through Optimism

Optimism, Sheridan argues, always expresses itself through action. Inspired by Viktor Frankl’s idea of choosing response over reaction, Sheridan encourages leaders to pick hope when confronted with uncertainty. He uses Edward de Bono’s “Six Thinking Hats” metaphor to explain balanced leadership: great leaders combine realism (the Black Hat) and optimism (the Yellow Hat). Caution and joy are complementary, not opposites.

Run the Experiment

The most repeated phrase in Chief Joy Officer is “Run the experiment.” When unsure, try something—even if imperfect. Sheridan recounts how he ended a keynote at MassMutual with this call. Months later, he discovered they had launched dozens of joyful experiments—even attaching helium balloons to desks to mark innovation zones. In one experiment, a claims department cut its turnaround time from four weeks to thirteen minutes. Optimism, Sheridan shows, creates extraordinary results when paired with courage.

Learning from Fear

Optimism is not blind faith. Sheridan describes navigating a storm on Lake Huron as a teenager and choosing to reassure his friend despite real fear. Leadership, he says, is similar—you must manage fear without amplifying it. Balance courage and caution, just as a pilot balances turbulence. Optimism, for Sheridan, doesn’t guarantee a smooth flight—it ensures the plane keeps moving forward even through storms.

Purpose, Sheridan claims, is the oxygen of leadership. Without it, no culture can breathe. Menlo’s purpose—to end human suffering in the world as it relates to technology—guides every decision. For Sheridan, purpose answers two questions: who do you serve, and what joy do you want to deliver? Leaders who define these answers clearly can create self-sustaining cultures of empowerment.

Start with Why

Echoing Simon Sinek, Sheridan differentiates between task-driven and purpose-driven work. At Interface Systems, he once ran teams by command; they moved fast but without meaning. After discovering IDEO’s experimental, collaborative design methods, he learned that purpose—not process—drives innovation. Setting the right “why” creates organizations where empowerment happens naturally.

Envisioning Ten Years Ahead

Sheridan describes Menlo’s ten-year vision—a vivid story of a future where 200 joyful employees gather to celebrate Edison’s 180th birthday in 2027. This exercise, modeled on Ari Weinzweig’s “visioning” method at Zingerman’s, transformed abstraction into daily action. Employees embedded goals from the vision into weekly meetings and sales metrics, making the dream tangible in every decision.

Serve Beyond the Obvious

Purposeful service goes beyond customers and investors—it reaches beneficiaries you may never meet. Sheridan’s example of the life insurance company illustrates this perfectly: their true service is to grieving families, not policyholders. In the same way, Menlo builds software not for revenue but to ease human frustration. Purpose becomes sacred when directed outward.

Turning Vision Into Systems

Vision without structure is chaos, and process without vision is bureaucracy. Sheridan blends the two through simple systems—weekly check-ins, open finances, and storytelling. These rituals keep purpose alive. When purpose is embedded in action, leadership transforms from management to stewardship, ensuring every day moves the team closer to something bigger than themselves.

Sheridan defines systems thinking as the bridge between culture and execution. Borrowing from W. Edwards Deming and pediatrician-system theorist John Gall, he argues that joy requires structure—but simple structure. Bureaucracy kills joy through complexity. Systems, on the other hand, support human creativity. Gall’s Law states that a complex system that works evolves from a simple system that worked. That principle became Menlo’s mantra.

From Chaos to Order

Sheridan tells an intriguing story of rediscovering his daughters’ pediatrician years later and realizing that his perfectly calm waiting room represented intentional design. Gall had built time buffers for emergencies—a system that worked. At Menlo, Sheridan applied the same logic: systems should minimize fear, not maximize control. His open-office design and paper tracking boards make accountability visible without micromanagement.

Rules Without Fear

Systems thinking, Sheridan reminds leaders, isn’t about rules—it’s about trust loops. When a nonprofit wanted to replicate Menlo’s babies-at-work experiment, they suggested forming a policy committee. Sheridan stopped them: “Don’t make a policy. Run the experiment.” Small, simple systems encourage trial and learning. Bureaucracy fears mistakes; systems embrace them.

Reward the Right Behaviors

One major breakthrough came when Menlo applied VitalSmarts’ principle: “The systems you have are perfectly designed to produce the behaviors you see.” Sheridan helped a neighboring company solve its collaboration problem by dismantling its “Wall of Fame” of individual patents. By rewarding teams instead of heroes, collaboration flourished. Systems, he insists, must reflect desired values—teamwork, transparency, and trust.

Speaking Truth to Power

Systems also protect psychological safety. Menlo holds quarterly meetings where employees set the agenda and ask founders tough questions—about pay, turnover, sales, and culture. Sheridan welcomes these moments as the heartbeat of a healthy system. Bureaucracy hides hard truths; systems invite them into the open. For leaders, this is the simplest and most powerful structure for building joy.

Near the end of the book, Sheridan reveals one of his favorite leadership practices—storytelling. He learned it from his father during a childhood canoe trip down Michigan’s Manistee River. When their canoe cracked, his father repaired it using pine tar and birch bark, turning crisis into legend. Sheridan later realized storytelling is the glue of leadership: facts are forgotten, but stories live forever.

Stories Create Culture

Sheridan calls storytelling “the lifeblood of intentional culture.” At Menlo, leaders share stories of success and failure to teach lessons. The tale of a lost $60,000 client deal that saved them from ruin later became an internal parable about integrity over expediency. Instead of metrics, stories transmit memory, values, and purpose from generation to generation of employees.

Contagious and Collective

Stories spread far beyond company walls. Sheridan recounts how clients like Don—an executive visiting Menlo—retold their experience to others, turning visitors into ambassadors. Joyful stories are contagious. When leaders tell authentic narratives, they don’t just teach—they invite others to carry the story forward, multiplying its reach like ripples in water.

Everyone Becomes a Storyteller

As Menlo grew, Sheridan couldn’t lead every tour himself. The team began pairing him with others, sharing storytelling duties. Initially reluctant to give up control, he soon discovered joy in hearing teammates tell his stories in their own way. The goal wasn’t perfection—it was connection. Stories, Sheridan says, “hold us accountable to who we say we are.”

Preserving Joy Through Story

Ultimately, storytelling cements culture more powerfully than strategy. Sheridan encourages leaders to collect stories through internal TED-style events or founder talks, recording them so joy becomes part of the company’s mythology. A culture that tells its story well protects its purpose. Storytelling, in Sheridan’s words, is “how we remember the joy we’ve chosen to lead with.”