How can leaders build a culture where people discover their potential, develop it, and multiply it through others?
How do you create an environment where every employee feels inspired and empowered to solve the problems that matter most? These are the defining challenges facing today’s leaders and company founders.
A handful of books have deeply influenced my own answers to these questions over the years and helped us shape a culture at Milestone that I am incredibly proud of. These books gave us a shared language and have strengthened our leadership philosophy. They have shaped our career pathing and leadership development frameworks. Today, more than 300 people across diverse geographic locations come together daily to solve some of the toughest challenges, learn from one another, and inspire each other every day.
Leadership Is Never About “I”
We’ve seen what happens when leaders focus too much on repeating “I, I, I” rather than on bringing people together. Departments become siloed war rooms, and people spend their energy proving a point instead of solving the problem. Even a brilliant leader can hold themselves and the company back. A leader’s core responsibility is to help other leaders and employees succeed.
This belief is the foundational thread of our leadership fabric. It brings us together to prioritize what matters, create clarity and focus, develop talent through deliberate practice, and break down departmental silos, all while leading with optimism, perseverance, and adaptability. This fabric of enablement matters most during periods of massive transformation. It rests on one simple truth: success multiplies when we work together toward a shared purpose.
Great cultures do more than hire brilliant people. They create an environment where people can discover their brilliance, develop it, and bring out the best in others.
I like to think about that environment in three parts: Manage Me, Manage My Organization, and Curate My Future. Each part is inspired by books that have shaped my approach to leadership. Along the way, I’ll share those books and the ideas that changed how I think and lead.
1. Manage Me: Lead Oneself Before We Lead Others
Leadership starts long before a title. It begins in the moments when pressure rises, certainty disappears, and we must choose whether to react or respond. Building Milestone over the past three decades has taught me some valuable lessons about managing myself before anyone else. Managing ourselves comes down to five practices.
A. Find Calm Clarity – Slow down and rise above the noise. Write your eulogy, not just your resume.
Before we can find calm clarity, we have to recognize what pulls us away from it. There are three traps I see time and again that hold us back: combat mentality, a victim mindset, and losing sight of what matters. Each pulls leaders away from clarity.
The way out is a choice. A can-do mindset answers excuses with solutions, blame with ownership, scarcity with possibility, and limits with potential.
Due Quach’s Calm Clarity framework describes three patterns of brain activation. Under threat, we react from fear and self-preservation (Brain 1.0); chasing reward, we turn anxious, impulsive, and restless (Brain 2.0). At our best, we lead from Brain 3.0: calm, centered, connected, and creative.
Strong leaders learn to recognize these patterns and intentionally shift towards Brain 3.0.
Intentional leaders slow down, rise above the noise, and regulate their reactions so they can make better decisions and lead intentionally. Staying in Brain 3.0 is a critical part of our leadership fabric. It is how we address the real issue instead of amplifying the emotion of the moment.
Calm clarity also raises a deeper question. Are we building only a successful resume, or a life and legacy we would be proud to be remembered for? Writing your eulogy, not just your resume, keeps today’s decisions anchored to what matters most.
B. Growth Mindset – Choose to be a learn-it-all, not a know-it-all. Discovery fuels growth.
Capability is not fixed. People grow through effort, feedback, learning, and persistence, and every failure is an opportunity to come back stronger. A know-it-all protects what they already believe. A learn-it-all keeps discovering, and discovery is what fuels growth.
How each mindset responds to failure, challenge, and the success of others.
C. Unleash Your Infinite Game
A growth mindset changes how we see ourselves. Simon Sinek’s ‘The Infinite Game’ changes how we see the game we are playing. Leadership is not about winning a quarter or beating a competitor. It is about building an organization capable of adapting and thriving over time.
The famous Navy SEALs Simon Sinek video, which talks about performance verses trust shows what that looks like in practice. Teams that win are not the ones that gather the smartest people on the planet. They are the ones that take their weakest members along with them. Nobody finishes unless the whole team finishes.
That is one of the biggest challenges in any company. Smart people often move quickly but don’t always take the time to help others. As leaders, we need to slow down and bring people with us. Transcendental Meditation has helped me learn to pause and lead more thoughtfully.
D. Practice Deeply – Brilliance is not simply born. It is practiced, nurtured, and built.
If the infinite game is about where we are going, The Talent Code by Daniel Coyle is about how we get better along the way. Talent is developed through deep practice, effective coaching, and the right environment. Break skills down, practice deliberately, get rapid feedback, and keep improving. Deep practice is not about speed. Sometimes slowing down and practicing every day is what unlocks the genius within us.
E. Grit Wins Over Talent
Practice builds the skill. Grit keeps us practicing. Angela Duckworth’s research in Grit shows that extraordinary achievement comes not just from talent, but from passion and sustained perseverance toward long-term goals.
Chip Conley, my mentor for the last 30+ years, has done great workshops on how to Adapt and stay in the flow zone at Stanford. Talent may give you a head start, but it will not take you very far on its own. What takes you the distance is grit: showing up, practicing, learning from setbacks, and staying committed to long-term goals. That is what turns potential into achievement.
2. Manage My Organization: Build Heart, Trust, and Resilience
Managing ourselves creates personal effectiveness. Managing an organization means multiplying that capability across a system. I focus on three commitments: build heart, build trust, and build resilience with relentless focus.
A. Build Heart
How do you build an organization that is self-sustaining? It starts with heart. People contribute their best when work gives them belonging, meaning, recognition, and a connection to purpose. Chip Conley’s PEAK gave us a way to see this clearly. I think of motivation as three pyramids, one each for employees, customers, and owners. Each starts with a transaction and rises toward something far more powerful:
- Employees move from money (base motivation) to recognition (loyalty) to meaning (inspiration).
- Customers move from having their expectations met (satisfaction) to their desires met (commitment) to their unrecognized needs met (evangelism).
- Owners move from transaction alignment (trust) to relationship alignment (confidence) to legacy (pride of ownership).
Heart sits at the center, connecting employees, customers, and owners.
The heart at the center gets created when all three triangles connect. Creating a unique corporate culture builds an enthusiastic staff, an enthusiastic staff develops strong customer loyalty, and loyal customers sustain a profitable business. Values that connect everyone hold that chain together, and building heart never means lowering standards.
B. Build Trust – Heart gives people a reason to care. Trust gives them the confidence to act together. Two books by Patrick Lencioni helped shape our culture, in which we truly care for each other by enabling every team member, aligning them, and helping them focus.
Start with clarity. The Four Obsessions of an Extraordinary Executive taught me that a leader’s most important job is to build a healthy organization. That means a cohesive leadership team, clarity about what matters, and overcommunicating that clarity until it is reinforced through people and operating systems. A sentiment I repeat in just about every meeting: until something is clear to every team member, it is not clear to anyone. The question is never whether leaders understand. The question is whether people understand. Aligning and enabling people, creating clarity, and breaking down department silos are all critical to building an organization that can execute and succeed together.
Building trust is super critical for high performing teams. How do you do that when teams are remote? The Five Dysfunctions of a Team shows how high-performing teams are built. Trust enables healthy conflict, conflict supports commitment, commitment makes accountability possible, and accountability keeps the focus on results.
The pyramid I always come back to. Each layer depends on the one beneath it.
Have the courage to be direct. Trust is not possible without authenticity. Brené Brown’s Dare to Lead shows how courageous leadership requires vulnerability, difficult conversations, clear values, and trust. Avoiding uncomfortable conversations may feel safer, but clarity and accountability require leaders to address issues directly. Hard conversations held with empathy are what break the pattern of artificial harmony.
Multiply, do not diminish. Trust also grows when leaders step out of the limelight. Great leaders do not need to be the smartest person in the room; they amplify the intelligence and capability of others. They create ownership, ask better questions, and build leaders, not followers.
Wiseman’s research found that Multipliers accessed nearly twice as much of people’s capability as Diminishers.
C. Build Resilience with Relentless Focus
You cannot focus on noise. Great organizations turn strategy into execution by defining what matters most and measuring the outcomes that prove they achieved it. At Milestone, we have yearly and quarterly OKRs based on measuring what matters by John Doerr. OKRs create focus, alignment, transparency, and accountability, connecting every team’s work to meaningful business results.
Resilience comes from five disciplines working together: strategic clarity, scalable talent, disciplined execution, relentless focus, and an energized culture. Each one poses a question every leadership team should answer honestly.
The 5x CEO’s five disciplines, five honest questions.
We have put these ideas into practice through cross-functional PODs, OKRs and goal alignment, revenue and metrics clarity, and a leadership posture of enablement rather than delivery. Above all, we celebrate cross-functional teams rather than individual heroics.
Leadership scales when intelligence, ownership, and confidence grow beyond the leader.
3. Curate My Future: Build What Lasts
Leadership is not only about managing today. It is intentionally shaping who we are becoming, and what our organization can become. Curating the future comes down to four practices.
A. Wisdom at Work: Turn Experience into Wisdom
Past experience becomes truly powerful when we apply it. That is the central idea behind Chip Conley’s Wisdom @Work. How do we use the years of knowledge our leaders have accumulated to help teams make better decisions, take calculated risks, and avoid repeating mistakes?
At Milestone, every leader owns a portion of their goals based on cross-functional success. Leadership is not just about succeeding within your own function. It is about enabling others and helping the organization succeed together. Most employees also have access to customer sentiment signals. That keeps them close to customer friction and helps them proactively identify where we need to improve.
For a company with nearly three decades of history, now navigating another major wave of transformation, one of our hardest leadership challenges is connecting everyone around a common thread while we continue to evolve. That is why staying ahead, customer delight, collaboration, and high performance have become critical pillars of our leadership philosophy and career pathing.
Wisdom also grows when we lean into our strengths without becoming trapped by past success, and when we learn to play the role of an intern and a coach at the same time. As leaders, our goal is to be curious enough to keep learning and generous enough to share experiences, judgment, and perspective with the next generation.
Experience gives us knowledge. Application turns that knowledge into wisdom. Sharing that wisdom helps the entire organization move forward.
B. Optimism, Focus, Resilience, and Adaptability
Last year, I had the privilege of attending an intense two-day leadership workshop at Stanford taught by Roberta Riga. This year, we did another workshop with her around Mindskills leaders need to be successful. One lesson stayed with me: mindset is more important than expertise. In times of rapid transformation, technical skills alone are not enough. Leaders must learn to manage their own psychology and how they respond to uncertainty. The future rarely unfolds as planned. Optimism keeps us looking for possibility, and focus keeps our energy on what matters most. Resilience helps us recover from setbacks, and adaptability helps us change as circumstances change.
Resilience and adaptability matter most when markets move fast. Efficiency is important, but speed is often more important. The key is knowing when to move fast, when to accept calculated inefficiency, and how to redesign people, processes, and leadership as we grow.
C. Self-Compassion – Self-compassion is different from optimism. Optimism looks forward to what is possible. Self-compassion is how we treat ourselves when things go wrong. It lets us learn from mistakes without losing confidence. Leaders who are harsh with themselves tend to avoid risk, hide errors, and stop learning. Leaders who practice self-compassion recover faster and come back ready to try again. None of these are traits we are simply born with. They are skills we can intentionally practice and strengthen. When transformation accelerates, our ability to lead ourselves becomes the foundation for our ability to lead others.
D. Portfolio Life: From Doing to Being
A career does not have to be a single ladder. I think of it as a portfolio of roles, interests, mentoring, and giving back, all contributing to who we become. Over time, leadership moves from doing to being. It is less about what we personally achieve and more about who we are and what we enable in others. A career is measured in roles and results; a legacy is measured in the people we helped grow.
One Bold Step at a Time
Leadership is a staircase, not a leap. This is the core concept of my non-profit, “My BoldSteps“. Clarity builds courage, courage builds confidence, confidence practiced consistently creates impact, and sustained impact becomes legacy. Each step is a small choice: pausing before reacting, asking a better question, or naming the issue everyone is avoiding.
These lessons inspired us to help people unlock their full potential. The Bold Steps journey is simple but powerful: Reaction to Clarity to Ownership to Purpose. It is about moving beyond self-doubt, discovering your strengths, developing your craft, and finding the courage to realize your potential.
Through Taking Bold Steps, we bring together remarkable leaders, inspiring them to share stories of perseverance, mindset, grit, and passion across the same three themes: managing yourself, managing organizations, and curating your future. Together, we climb the staircase of leadership and weave a fabric built from threads of calm clarity and trust. Explore Taking Bold Steps: Leadership Fabric and Staircase to watch the sessions on demand.
When enough people take those steps together, culture changes. People stop waiting for brilliance to arrive from the top, and start discovering it in themselves, developing it through practice, and multiplying it through others.
The Books Behind Multiply Brilliance
None of these ideas began with me. These are the books that deeply influenced me and shaped our leadership fabric at Milestone, with the value each one added.
Manage Me
1. Calm Clarity by Due Quach.
The source of the Brain 1.0, 2.0, and 3.0 model, with practical tools for catching yourself in a reactive state and returning to calm. Read it if pressure tends to make your decisions for you.
2. Mindset by Carol Dweck.
The research behind the fixed versus growth distinction, including how the way we praise and give feedback shapes which mindset people adopt.
3. The Infinite Game by Simon Sinek.
A compelling case for leading with a just cause and measuring yourself against your own progress, not against your competitors.
4. The Talent Code by Daniel Coyle.
Shows how deep practice actually works, including why struggling at the edge of your ability is what builds skill.
5. Grit by Angela Duckworth.
Explains how passion and perseverance develop over time, and how leaders can cultivate them in the people around them.
Manage My Organization
6. The Four Obsessions of an Extraordinary Executive by Patrick Lencioni.
A leadership fable that makes organizational health concrete, and the clearest guide I know to overcommunicating clarity.
7. The Five Dysfunctions of a Team by Patrick Lencioni.
Another fable that brings the trust pyramid to life through a leadership team you will recognize, with practical ways to strengthen each layer.
8. Dare to Lead by Brené Brown.
Turns courage into teachable skills, from embracing vulnerability to living into your values. Essential for leaders who avoid hard conversations.
9. Multipliers by Liz Wiseman.
Profiles the disciplines that set multipliers apart, and the “accidental diminisher” habits well-meaning leaders fall into without realizing it.
10. Measure What Matters by John Doerr.
Real stories from Intel, Google, and others showing how OKRs are written, tracked, and used to keep teams aligned.
11. Radical Candor by Kim Scott.
A simple framework of caring personally and challenging directly that gives teams a shared vocabulary for feedback.
12. The 5x CEO by Samantha Allison and Taavo Godtfredsen.
Built around CEOs who drove outsized results, it frames the five disciplines as questions a leadership team can use to pressure-test its strategy.
Curate My Future
13. PEAK by Chip Conley.
Conley’s account of applying Maslow’s hierarchy to steer Joie de Vivre Hospitality through a downturn, and the origin of the three pyramids. Especially relevant for anyone in hospitality.
14. Blitzscaling by Reid Hoffman and Chris Yeh.
Maps how a company changes as it grows from a family to a tribe, village, city, and nation, and how leadership must change at each stage.
15. Wisdom at Work by Chip Conley.
Conley’s story of joining Airbnb in his fifties as both mentor and student, and the origin of the Modern Elder idea.
