The awkward truth of leadership

Leadership often begins at the very moment we would most like to step back. The tension is familiar to me. When I enter a room as the CEO, my silence can still carry weight. People look for cues, measure my stillness, and wonder if it means permission or warning.

With my own team, this has changed for the better. They know I am introverted and that I rarely chair meetings directly. I prefer to empower the younger generation or my COO to take that role, because empowerment is not a theory to me, it is culture in motion. Yet when newcomers or external partners join us, they come with different expectations. They look to the CEO’s chair and assume the CEO will preside. In those moments, if I hold back, the atmosphere tightens. Respect pulls me one way, responsibility pulls another.

This is awkwardness. And awkwardness, I am learning, is not weakness. It is the doorway into empowerment.

Two days that made the point

Sunday Evening. Ministry, an educator’s blind spot, and the weight of silence

The weekend closed with ministry. For five years I have joined the Business and Professional Ministry on Zoom. I may not always lead the discussion, but I show up. Consistency forms leaders in ways charisma never can.

Earlier that day, I spoke with one of our educators at Stellar. She is bright, articulate, and full of promise. Yet this is where leaders fall into a subtle trap. We see brightness and assume completeness. We think capability should equal readiness. That assumption is entitlement dressed up as expectation: I am entitled to be understood, I am entitled to be respected, I should not need to explain.

But empowerment does not start with assumption. It begins with curiosity. That afternoon, I slowed down long enough to ask about her story. Together, we traced a present struggle back to her upbringing environment. What she thought was simply her “weakness” was in fact a pattern formed long ago. She had never seen the link before. The moment she did, her posture shifted. Shoulders eased. Voice steadied. The Johari Window explains this space: what is unknown to self but known to others can become fertile ground when trust is present.

That conversation reminded me of the three voices a leader must practice: caring, charting, and challenging.

• The caring voice listens, empathizes, and creates safety.
• The charting voice provides direction and names purpose.
• The challenging voice stretches people when trust can carry the weight.

I am naturally strong in caring. I am learning to chart. I reserve challenge for covenantal trust, because challenge without care wounds and challenge without charting disorients.

And here is the nuance I live with now. My silence with my own team is no longer misunderstood. They know I do not need to chair every meeting, because I trust them to do so. I have empowered them to step forward. But when externals step into the room, they have not yet experienced this culture. They wait. They expect the CEO to preside. If I remain silent then, what I intend as humility can sound like hesitation, and what I hope is empowerment can feel like abdication.

This is why awkward initiation matters. Not to dominate the room, but to lower the fear of the unfamiliar and open the floor so others can contribute.

That evening, the educator messaged me with gratitude. Not for perfect answers, but for presence. For someone willing to sit long enough to link her behavior with her environment and offer a safe mirror. That was enough to unlock choice. And choice is where empowerment begins.

Sunday Afternoon. Family rhythms, UNO at a café, a jog that became futsal, and the shape of memory

Earlier that Sunday, the day had belonged to family.

After nearly two weeks apart, I finally saw my youngest son, Evan. He had gained weight and looked healthier, livelier. I felt deep gratitude for my mother, who had been caring for him. Leadership is never abstract when it touches the face of your own child.

My wife had been searching for enrichment opportunities and signed our children up for art and drawing classes. In the past, I might have dismissed these as unnecessary. But now I see something different. These classes create rhythms. They force me to fetch and wait, which turns into conversations. They anchor our days, giving us reference points for storytelling at the dinner table. They shape belonging.

Later, we stopped at a café and played UNO. We laughed, debated rules, and practiced the humility of losing. Afterwards, I jogged with my son, gently encouraging his fitness. Along the way, we invited neighbors to join us. Then came an interruption. A group of teenagers under fifteen asked if I could accompany them to the futsal court. They needed an adult above eighteen to sign them in. I agreed. My presence became their access to joy. We stayed until they were settled, then found a “prison-break” way out so we could still jog home in time for dinner.

After nap time, I edited photos from our Guangzhou trip. For each picture, I wrote a caption in Chinese. One word, one story, one memory. My hope is that my children will learn language through lived experience, not rote drills. One task carried three purposes: bonding, learning, legacy. Integrated living. Intentional legacy.

These are not distractions from leadership. They are the training ground. If I cannot initiate awkward conversations with my children, how will I do it wisely at work. If I cannot steward minutes with my family, how can I steward hours with my team. If I cannot notice details while walking, I will miss them while speeding down highways.

Respect, responsibility, and how the three voices work together

The paradox is sharper when new people are in the room. My team knows my rhythm. They trust my silence as empowerment. They expect to chair. But newcomers arrive with traditional assumptions: that the CEO must lead from the front. In those moments, silence creates confusion. Respect without responsibility looks like hesitation. Responsibility without respect looks like domination. The leader’s task is to hold both in tension.

This is where the three voices guide me.

• Begin with the caring voice so people feel safe, especially newcomers. As Mother Teresa once said, you touch the person before you ask for their hand. Maxwell calls this the Law of Connection.
• Then use the charting voice. One clear sentence to frame the purpose of the meeting and outline what good looks like. Maxwell names this the Law of Navigation: anyone can steer the ship, but leaders chart the course.
• Finally, bring the challenging voice when trust is strong enough to sustain it. As Purposebility reminds us: ninety percent of growth lies in ten percent of courage.

Awkwardness is not failure. It is the hinge. With insiders, silence can empower. With outsiders, initiation may be necessary. Either way, the leader’s choice to speak the first word determines whether the room becomes fearful or free.

World-class truths affirm this. Lincoln’s first taste of command ended in demotion because he could not yet command confidence. McDonald’s brothers had talent but lacked vision until Ray Kroc charted a bigger map. Gallup research shows that seventy percent of employee engagement is shaped by managers. Avoidance is costly. Awkwardness, embraced, becomes the soil of growth.

From presence to multiplication

I measure leadership not by the tasks I complete, but by the leaders I raise. My dream is to multiply one hundred thousand leaders in my lifetime. Not by my hand alone, but through ripple effects. If I empower 160 who embody faithfulness, availability, and teachability, and if a portion of them replicate that impact, the numbers grow exponentially.

Maxwell calls this the Law of Explosive Growth: if you want growth, lead followers. If you want multiplication, lead leaders. Multiplication begins with presence. It continues with culture before strategy, identity before position, and systems that protect what matters most.

For me, this looks like:

• Opening every meeting with a clear why.
• Naming whether I am speaking in a caring, charting, or challenging voice.
• Asking Johari Window questions that surface blind spots without shame.
• Helping people connect present behavior to past environment, unlocking agency.
• Stewarding my body as intentionally as my calendar.
• Guarding small family practices — UNO, jogging, futsal — as leadership lessons.
• Writing stories from Guangzhou photos as both memory and curriculum.
• Counting stewardship, not hours. 急性子 can be a gift when governed by purpose.

When these practices take root, leadership impact multiplies. People are not only inspired. They are equipped to raise others.

The reverse that reframes the whole piece

The greatest threat to leadership is not following. It is self-protection dressed as politeness. With my team, silence has become empowerment because they know the culture. With externals, silence can still confuse.

So I will continue to empower my COO and younger leaders to chair, because that builds ownership. And when newcomers are present, I will initiate first, then hand the room back to them. Both are leadership. Both begin in awkwardness.

Because empowerment does not start in confidence. It begins when a leader accepts awkwardness as part of the work, speaks the first sentence with presence, and opens the floor for others to rise.