The Evolved Executive

Have you ever wished your team could consistently bring their best selves to work—showing up motivated, focused, and genuinely excited to contribute? In How to Be a Great Boss, Gino Wickman and René Boer argue that this dream is absolutely achievable. Their central claim is both simple and demanding: great bosses create environments where people love what they do, feel deeply accountable, and thrive under leadership that combines clarity with empathy. And being that kind of boss isn’t about charisma or authority—it’s about mastering specific practices that make your team great.

The authors contend that the world’s frustrations with work—low engagement, endless churn, and constant miscommunication—stem not from bad employees, but from bosses who never learned to lead and manage well. Drawing on decades of experience with thousands of leaders, Wickman and Boer distill their lessons into practical tools that any manager can apply, centered around a system called the Entrepreneurial Operating System (EOS). Their message: leadership isn’t theoretical. It’s concrete, measurable, and learnable.

The Core Challenge: Building Engaged Teams

The authors start with a sobering truth—most employees aren’t engaged. Gallup and Harris polls reveal that fewer than one-third of American workers feel motivated or connected to their work; nearly half don’t even know their company’s goals. This disengagement costs billions in lost productivity and morale. For Wickman and Boer, this isn’t just an economic problem—it’s a leadership one. A great boss can transform disengagement into enthusiasm by mastering the twin disciplines of leadership and management.

Leadership, they explain, is about vision, direction, and inspiration—it’s working "on" the business. Management is about execution, consistency, and accountability—it’s working "in" the business. Combined, they form the book’s key equation: L + M = A. Leadership plus Management equals Accountability. And accountability isn’t about cracking a whip—it’s about creating conditions where people deliver results because they understand why they matter.

The Journey to Becoming Great

The book unfolds as a practical roadmap. The first step is self-assessment: do you truly get it, want it, and have the capacity to do it? These three questions instantly separate thriving leaders from struggling ones. If you lack understanding, passion, or the emotional stamina to manage people, the authors suggest that you shouldn’t force yourself into leadership—you’ll only suffer and hold others back. But if you do “get it” and “want it,” and are ready to build your capacity, the rest of the book will equip you to act with confidence.

Next, the authors introduce Delegate and Elevate™, a tool for freeing your time so you can focus on high-value leadership activities. Instead of drowning in tasks, you assess everything you do using four quadrants—what you love and are great at, what you like and are good at, what you dislike but do well, and what you dislike and do poorly. The goal: delegate the bottom two quadrants. Delegation isn’t abdication—it’s elevation. It improves your people’s autonomy and your own effectiveness.

Once a boss creates that breathing room, the next step is people. Through The People Analyzer™ tool, Wickman and Boer help you ensure everyone on your team shares your company’s Core Values (the “Right People”) and sits in the job that fits their abilities (the “Right Seat”). Being a great boss doesn’t mean managing average performers—it means surrounding yourself with people at or above “The Bar,” your minimum acceptable standard for values and competence.

From Vision to Practice

Chapters five through seven are the heart of the book—the practices that translate theory into impact. The Five Leadership Practices teach you to give clear direction, provide tools, let go of control (what the authors call “letting go of the vine”), act for the greater good, and take regular Clarity Breaks™ to think strategically. Combined, they cultivate trust and confidence in your team. The Five Management Practices mirror that structure with concrete habits: keeping expectations clear, communicating well, maintaining the right meeting rhythm, conducting Quarterly Conversations, and rewarding and recognizing quickly.

In these chapters, the book’s tone feels conversational yet rigorous—packed with real-world stories from managers like Kris Marshall or Kelly Cuellar, whose simple changes transformed morale. It’s reassuring to see that these tools don’t rely on personality. You can be tough or gentle, introverted or extroverted—the key is consistency. Authenticity, not performance, earns trust.

Facing Reality: People Problems and Courage

Later, the authors tackle what bosses fear most: handling underperformers. They simplify the countless “people issues” into just four types—Right Person, Right Seat; Right Person, Wrong Seat; Wrong Person, Right Seat; and Wrong Person, Wrong Seat. Each one demands a different response, but all require courage. Often, the hardest choice is letting go of someone who shares your values but can’t perform. But as Wickman and Boer emphasize, keeping the wrong people poisons morale and undermines your credibility.

The closing chapters remind you that turnover can be a sign of health, not dysfunction. “Good turnover,” when wrong people leave, creates space for growth and strengthened culture. “Bad turnover,” when good people leave due to poor leadership, is what you must prevent. The goal is alignment—getting every arrow in your organization pointing in the same direction.

Why These Ideas Matter

Wickman and Boer’s message resonates because it combats the loneliness and overwork so many managers feel. They argue that being a great boss is not about working harder—it’s about working smarter, focusing your time where you have energy and value. Like Jim Collins in Good to Great or Stephen Covey in The 7 Habits of Highly Effective People, their advice empowers you to lead with clarity, discipline, and care. The difference is their simplicity: these tools aren’t abstract—they’re plug-and-play practices you can start tomorrow.

Key Idea

When you lead and manage well—when you elevate yourself by delegating, surround yourself with great people, and commit to accountability—you not only transform your department. You transform your life. You gain peace, autonomy, and joy. And one day, as the authors promise, someone you manage will look you in the eye and say, “You’re the best boss I’ve ever worked for.”

Early in the book, Wickman and Boer pose three deceptively simple questions that form the foundation of leadership success: Do you get it? Do you want it? Do you have the capacity to do it? These questions are so essential that they reappear throughout the EOS system. Together, they form a model for assessing both yourself and your team. If the answer to any is No, it’s time for a reality check.

Get It: The Intuitive Understanding

To get it means more than technical competence. It’s having innate understanding—the intuitive sense of how things work. The authors compare it to aptitude, a kind of leadership “biochemistry.” A manager who truly gets it anticipates problems, communicates effortlessly, and knows how to harness strengths. One example tells of a retail manager who turned around a failing store by rearranging roles based on personalities: distinguishing “box people” (who love order) from “people people” (who love customers). That instinct—not theory—saved the store.

Want It: The Passion and Commitment

Wanting it means possessing genuine desire for the responsibilities and challenges of being a boss. You don’t just accept the role—you embrace it. One leader featured in the book, John Eadie of Covenant Multifamily Offices, notes that even great training fails when people don’t have genuine drive. Wickman and Boer remind you: people who love leading don’t see obstacles—they see opportunities. They feel the “fire in the belly” that sustains motivation when times get tough.

Capacity: The Four Dimensions

Capacity covers emotional, intellectual, physical, and time dimensions. Emotional capacity means empathy and self-awareness; intellectual capacity is critical thinking and problem-solving; physical capacity is stamina and work ethic; time capacity is organization and prioritization. Great bosses master all four. Those who lack any one become bottlenecks or burn out. For instance, a leader who lacks emotional capacity erodes trust by ignoring the feelings of their team, while one without time capacity drowns in chaos. As the authors put it bluntly, “Life is too short to be a bad boss.”

Key Idea

Your ability to lead starts by asking: “Do I truly get the job? Do I want it? Do I have the emotional and time capacity to excel?” If the answer is yes, you’re ready to build greatness. If not, you must either grow—or let go. Great bosses start with radical honesty about themselves.

One of the book’s most transformative lessons is Delegate and Elevate™. It’s more than a time-management trick—it’s a mindset shift about letting go. The authors observe that many bosses drown in tasks they shouldn’t be doing. They put in 60 hours of work trying to accomplish what should take 40—only to end up exhausted and ineffective. The cure is learning to delegate and elevate yourself toward activities that match your unique strengths.

The Four Quadrants of Work

The Delegate and Elevate exercise organizes all your tasks into four quadrants: (1) Love/Great; (2) Like/Good; (3) Don’t Like/Good; and (4) Don’t Like/Not Good. The first two contain energizing work; the bottom two drain your energy. Your mission is simple: delegate tasks from Quadrants 3 and 4. This lets you spend your time in the upper quadrants—the activities that leverage your talents. As Wickman warns, routines easily become ruts. When you intentionally reassign tasks that drag you down, you elevate your performance and your people’s growth.

Why Bosses Resist Delegation

The authors list common excuses for not delegating—everything from “No one can do it as well as me” to “It takes too long to teach them.” They call these stories “personal head trash.” In truth, great bosses let go because they know their team can rise to the challenge. A Texas manager named Debra Hutson conquered her own resistance by hosting “Help Debra Day”: she shared her self-assessment with her team and discovered that tasks she hated were ones her employees loved. That delegation boosted morale and freed up time for strategy.

Elevating Yourself and Your Team

Delegation doesn’t just serve you—it elevates your team. When you hand off meaningful work, people feel trusted and valued. They gain autonomy, competence, and motivation (echoing Daniel Pink’s Drive). The authors argue that delegation transforms a boss from a bottleneck into a builder of capacity. Chris Beltowski of imageOne discovered that delegating what bogged him down helped both him and his team “grow exponentially.”

Key Idea

Stop doing everything yourself. By letting go of tasks that drain you and empowering others to take ownership, you create time for leadership, increase job satisfaction, and build a thriving, accountable team.

In Chapter 5, Wickman and Boer reveal the formula that defines everything else: L + M = A. Leadership plus Management equals Accountability. You can’t expect accountability—it must be created. This insight reframes leadership entirely: it’s not personality, pressure, or performance bonuses that drive results; it’s clarity and consistency in leading and managing simultaneously.

The Four Truths

Before diving into tools, the authors present four foundational truths: (1) being a great boss can be simple; (2) your style doesn’t have to change—authenticity builds trust; (3) you must genuinely care about your people; and (4) you must truly want to be great. Without these, no framework works. Caring, in particular, is non-negotiable: “People don’t care what you know until they know that you care.” This echoes Dale Carnegie’s timeless principle in How to Win Friends and Influence People.

Vision and Traction

Leadership and management represent two sides of a coin: Vision and Traction. Vision involves setting direction—working “on” the business. Management involves creating traction—executing that vision by working “in” the business. The authors quote Thomas Edison: “Vision without execution is hallucination.” Together, they make accountability inevitable. Great bosses don’t just inspire—they follow through.

Creating an Engaged, Accountable Culture

Accountability flows from clarity. When people know exactly what’s expected, when they have strong core values, and when they know their metrics, they don’t need micromanagement—they self-manage. Wickman and Boer emphasize that engagement comes from direction and alignment, not perks. A boss who communicates vision and provides traction gets results because their people understand the what and the why.

Key Idea

Leadership sets the vision; management makes it real. When you consistently deliver both, you create trust and accountability—the hallmarks of a culture where people perform at their best.

The book’s sixth chapter breaks leadership into five practices that transform how people follow you: Giving Clear Direction, Providing Necessary Tools, Letting Go of the Vine, Acting with the Greater Good in Mind, and Taking Clarity Breaks™. These aren’t abstract ideals—they’re behaviors you can put into action immediately.

Clear Direction and Tools

Great leaders give clarity and resources. You can’t motivate people with confusion. The authors urge you to share vision every ninety days and tie it to specific goals—the “Eight Questions” that define your company’s focus, target, and metrics. Then, give your team the tools—training, technology, and, crucially, your time. As one manager admitted, failing to spend time with his people was the real cause of poor results.

Letting Go of the Vine

Letting go of the vine represents the art of trust. Once you’ve provided clarity and tools, you must let your team run without micromanaging. The classic story in the book—a boss who prided himself on being the “answer man” until realizing he was the bottleneck—illustrates perfectly why autonomy matters. As Ken Blanchard said in The One Minute Manager Meets the Monkey, you can’t take every problem as your own. Your people must walk out of your office with their own monkeys, not yours.

Acting for the Greater Good and Taking Clarity Breaks

Leaders act for the greater good: they make decisions that serve the organization, not their ego. The authors describe Todd Sachse’s “10-10-10 Rule”—evaluate every decision over ten minutes, ten months, and ten years. When he prioritized reputation over profit, his construction firm emerged stronger. Finally, taking Clarity Breaks helps you regain perspective. Like Stephen Covey’s “sharpen the saw,” this habit pulls you out of chaos so you can think strategically.

Key Idea

Leadership isn’t about control—it’s about clarity, trust, and reflection. When you lead people with clear vision, give them the tools they need, let them run freely, and act with integrity, your culture thrives.

If leadership is vision, management is traction. Wickman and Boer detail five management practices that guarantee accountability: (1) Keeping Expectations Clear; (2) Communicating Well; (3) Maintaining the Right Meeting Pulse™; (4) Having Quarterly Conversations™; and (5) Rewarding and Recognizing Quickly. These habits turn managers into anchors of stability and trust.

Clear Expectations and Communication

Without expectations, accountability collapses. The authors urge managers to clarify roles, core values, rocks (quarterly priorities), and measurable metrics. Clarity gives people solid ground to stand on. Then comes communication—a discipline built on listening. Methods like the “Two Emotions” check-in or maintaining an 80/20 question-to-statement ratio ensure dialogue instead of direction. Avoid “thump-thump”—where what you say sounds perfect in your head but lands flat. Always echo and confirm understanding.

Meeting Pulse and Quarterly Conversations

Weekly meetings with consistent cadence keep teams connected. A sixty-minute meeting with metrics, issues, and follow-ups maintains alignment. Quarterly Conversations complement this rhythm. They’re informal, intimate discussions around what’s working and what’s not. This one-on-one time solidifies trust and course corrects before relationships fray.

Rewarding, Recognizing, and Correcting

Feedback must come fast—within twenty-four hours. Praise in public, criticize in private. Recognition fuels motivation more powerfully than money. Yet, when performance falters, apply the Three-Strike Rule: identify the issue, review after thirty days, and act after three strikes. Most will self-select out before termination. Discipline, consistency, and compassion are the cornerstones of great management.

Key Idea

Through clarity, connection, and quick feedback, great managers build self-sustaining accountability. They turn teams into trusted systems where progress never depends on pressure—it depends on mutual respect and rhythm.

Even great bosses must face uncomfortable truths: not everyone fits or performs. The authors compress hundreds of complex “people problems” into four universal types—Right Person, Right Seat; Right Person, Wrong Seat; Wrong Person, Right Seat; and Wrong Person, Wrong Seat. Facing these requires what Confucius called courage: seeing what’s right and doing it.

Right Person, Right Seat

Paradoxically, even this perfect pairing can become an issue if neglected. If you don’t invest time with your best people, they stagnate. One wise father-in-law in the book asked his son-in-law manager, “Who gets most of your attention—your best managers or your worst?” It’s a reminder that great performers need challenges and recognition, not just avoidance. Continuous praise and higher expectations prevent complacency.

Wrong Seats and Wrong People

“Right person, wrong seat” describes beloved employees who fit your culture but struggle in the role. Sometimes, a seat change—like Russell at Broder and Sachse Real Estate moving from analysis to property management—turns failure into excellence. But if no better seat exists, parting ways kindly and with dignity is the right course. “Wrong person, right seat” marks toxic stars—the “productive jerk” who hits targets but violates core values. Firing them, though painful, preserves the soul of the company. Finally, “wrong person, wrong seat” is the easiest call but most often avoided. Keeping them destroys morale faster than any external threat.

Raising the Bar

Courageous bosses maintain The Bar—the minimum acceptable standard. They blend empathy with decisiveness: offering help, delivering feedback, and ultimately taking action. HR policies shouldn’t replace courage; they should support it. True respect from your team comes not from kindness alone, but from integrity in addressing problems.

Key Idea

There are only four kinds of people issues. Handle each decisively, and you’ll keep your culture strong and your people inspired. Every time you close one chapter—whether through coaching or letting go—you open space for excellence.