Voices in Leadership
Voices in Leadership begins with a regular column from our CEO, Henry Sanders. In these reflections, Henry shares his perspective on leadership, vision, and community — offering insights shaped by experience and grounded in Wisconsin’s future. Explore his latest columns below.
The Selfless Way: Start scared. Lead anyway.
One person’s belief. One idea. One person’s conviction that their vision matters. That’s all it takes to overcome fear and make an impact in the world.
The other day, a friend texted me about starting a business to help women feel seen, heard, and empowered. She had the idea, the name, the mission, and a lifetime of experience behind her. But then came the real question:
“I’m scared. Were you ever scared? How do you get over the fear when starting something?”
I paused before replying because I knew this wasn’t just about fear. It was about whether being one person was enough.
That’s the burden of faith in leadership: believing you are enough to take the first step, even when your impact feels small. We tell ourselves we’re not big enough, not loud enough, not ready enough. But here’s the truth:
You don’t need permission to begin.
You don’t need perfection to make progress.
And you don’t need an audience to make an impact.
Most people underestimate what one person can do when they move with focus and conviction.
When I started Madison365, I was terrified. I had a newborn at home and was about to walk away from a stable job and steady paycheck. I didn’t have a journalism degree. I didn’t even have media experience. What I did have was a deep conviction that every community deserved to be seen and every voice deserved to be heard.
The choice wasn’t safe. It wasn’t perfect. But it was necessary. We launched as a nonprofit because we wanted the community to own it. We were mocked for that decision. Competitors said it would never last.
Yet ten years later, Madison365 is still here. Not because the fear disappeared, but because we moved forward through the fear. One idea. One person. And two others who believed enough to join in.
That’s the part we don’t talk about enough: change rarely starts with a crowd. It starts with one person making one bold choice.
History is filled with people who started small and made a big difference. The teacher who decides every child matters, even when the system says otherwise. The single mom who works three jobs to create opportunities for her kids. The entrepreneur who sees a gap in the market and chooses to fill it instead of waiting for someone else.
Mother Teresa wasn’t famous when she began. She was just a schoolteacher in Calcutta who walked past people suffering on the streets until she couldn’t ignore it anymore. From her quiet acts of love, an entire movement of service was born.
Steve Jobs wasn’t a household name when he started either. He simply believed technology could feel human — intuitive, elegant, accessible. He followed that one idea until the world caught up.
Different stories. Same truth. Real change starts with a single conviction acted on with courage.
Fear will always be there. The greater danger isn’t failing — it’s never becoming who you were meant to be.
When we ignore that inner pull to act, we’re not just delaying a dream. We’re denying the impact it could have on others. The second you move, you give others permission to move too. Courage is contagious.
So if you’re scared? Good. That means you’re awake. If you’re nervous? That means you care. But if you’re waiting for the perfect moment? You’ll be waiting forever.
Perfection isn’t the starting line. Movement is.
Here’s where to begin:
Identify one challenge or opportunity you’re ready to tackle.
Take one small step today — no matter how tiny. Progress comes from doing, not just planning.
Reach out to someone who believes in you and can push you forward.
Set a clear deadline for your first move.
Celebrate progress, not perfection.
Momentum builds from small wins. Each step lays the foundation for the next.
So start the thing. Build the business. Speak the truth. Make the call. Write the policy. Stand your ground.
That’s how every meaningful change begins — not with certainty, but with conviction.
The world doesn’t just need more leaders. It needs more people who believe that one is enough. One person can shift culture. One voice can spark change. One choice can turn fear into impact.
About the author
Henry Sanders is the CEO of Madison365, founder of the 365 Leadership Summit, and an executive coach who helps leaders navigate transitions, build trust, and lead with lasting impact — not just surface-level performance. Just stepped into a new leadership role — or preparing for one? Start with a free 15-minute Leadership Audit: a no-pressure session designed to help you clarify your next 100 days and lead with presence, not panic. To schedule your session or learn more about executive coaching, email Henry@365nation.com.
The Selfless Way: Leadership is a contact sport
Before I became a CEO and executive coach, I was a boxer. Not a hobbyist. A real one. Regional amateur champion. Long hours. Real hits. Bloody noses. Quiet wins. Humbling losses.
And while I never expected boxing to follow me into boardrooms, coaching sessions, and leadership retreats, it did. Because leadership, like boxing, isn’t just about talent. It’s about toughness.
Not the kind that shows up on posters or in highlight reels. I’m talking about resilience — the kind that keeps you getting back up when everything in you says to stay down.
The First 100 Days: Leading with presence, not performance
Everything had gone to plan. You did the work. You got the job. Now what?
Everyone talks about the first 100 days in a new leadership role — but no one talks about how overwhelming that time can really be. That’s true for any leadership role, from a newly elevated Fortune 500 CEO to someone in their first management role at a small business.
I recently helped a high-profile executive prepare for a new leadership role in a different state. The hiring committee had bought into his vision, his goals, and his leadership style. On paper, it looked like the perfect fit.
But by the end of Week One, he was already overwhelmed. By Day 15, isolated.
The inbox was full. The calendar was packed. And despite his clarity going in, the pressure to perform quickly started replacing the purpose that got him there in the first place.
If he hadn’t walked into the role with a clear, strategic 100-day plan, he likely would’ve defaulted to survival mode. Instead, he had a strategy that helped him stay focused, grounded, and proactive.
There’s a lot of hype around “hitting the ground running.” But here’s the truth: Speed without strategy leads to misalignment. And misalignment can cost you trust, clarity, and momentum.
In nearly every leadership transition I’ve seen, four common blind spots show up early. In a world obsessed with speed and visibility, grounded leaders choose a different way. These four anchors won’t just get you through the first 100 days — they’ll shape the kind of leadership that actually lasts.
1. Presence Before Performance
Before you lead a team, shape a strategy, or cast a vision — pause. Not to prove, but to become present. Real leadership begins in awareness: Who are you becoming? What’s driving you? What’s the bigger story beneath the noise? The pressure to perform will be loud.
Performance without presence leads to burnout, disconnection, and shallow impact. Presence, on the other hand, builds trust. It creates space for truth. It reminds you why you’re here.
Then comes the silent thief: impostor syndrome. It sneaks in when leaders try to mimic others instead of leading authentically. You might feel pressure to fit into the existing culture, but don’t let the culture dictate his leadership style. Take the time to understand the culture deeply, then guide it toward a healthier version that honors your true voice.
2. Listen Before You Speak
In his first 100 days, your words matter less than your posture. Every room you enter is holding tension, expectation, and unspoken history — like a table already set before he arrives.
Don’t rush to fix. Don’t rush to impress. Ask better questions. Stay curious. Let people feel heard — especially the ones who rarely are. Listening is more than strategy. It’s how leaders build trust, and how teams reveal truths.
3. Build Trust, Not Influence
People can feel the difference between someone who’s performing what they think leadership looks like, and someone who’s consistently leading. In the first 100 days, great leaders don’t just say the right things — they do them. That’s how cultures shift — not with slogans, but with daily choices that build credibility.
Here’s the reality: no one leads alone. Every great leader needs great managers and a culture that empowers them. Leadership isn’t about doing everything yourself. It’s about building a system where trust runs deep, execution is shared, and accountability is everyone’s job.
4. Protect the Culture, Not the Calendar
You were brought in to lead, but you also inherited something. Maybe it’s healthy. Maybe it’s broken. He needs to pay attention to what’s already growing beneath the surface: how people treat each other, how conflict is avoided or handled, how truth moves (or doesn’t).
If your calendar is full but the culture is toxic, you’re not leading. You’re managing chaos. The culture will either support your leadership or silently erode it. Either way, it’s shaping your impact, whether you’re paying attention or not. The best leaders build environments that support long-term resilience over short-term results.
In that recent executive transition, his 100-day plan included one non-negotiable: stakeholder engagement.
His team created a list of key internal and external people to meet with. But he didn’t stop there. He did his own research to identify additional voices he might not think to include: staff at all levels, community leaders outside the usual circles, and stakeholders with honest opinions about the organization.
He looked for themes. He asked consistent questions across every department, so he could identify patterns, blind spots, and culture gaps. He wasn’t just introducing himself as a new leader. He was listening for insight. Listening for truth. Listening for what might be broken, and what might be beautiful if it were better supported.
Externally, the goal was trust-building, but also truth-finding. Those conversations reflected racial, cultural, and generational diversity — because if your leadership plan is built only on what insiders say, he’s leading an echo chamber.
The most effective leaders know that a big part of the job — especially in those first 100 days — is putting out fires. The key to success beyond those 100 days, though, is not to react to problems, but understand the patterns behind them. By the end of those first 100 days, you should have a much clearer picture: What fires remain? Where do they keep flaring up? And why haven’t they been addressed until now?
Sometimes, the fire points to a system failure. Sometimes, it exposes a leadership gap. Sometimes, it reveals a culture that avoids conflict. Whatever the root cause, you need to pay attention to what’s burning and decide whether you’re just managing problems, or truly leading change.
There’s a real temptation in the first 100 days to prove yourself. To perform. To justify the hire and show you belong.
But the most grounded leaders don’t lead from performance. They lead from clarity, purpose, and conviction. They know who they are, and they stay aligned even when the pressure mounts. They don’t just want to look good in the role. They want to be effective for the people they serve.
And that kind of leadership? It doesn’t happen by accident. It takes preparation. Reflection. Courage.
The first 100 days can define or derail your leadership. Don’t just perform. Lead with clarity, presence, and purpose — and build the kind of leadership that lasts.
About the Author
Henry Sanders is the CEO of Madison365, founder of the 365 Leadership Summit, and an executive coach who helps leaders navigate transitions, build trust, and lead with lasting impact — not just surface-level performance.
Just stepped into a new leadership role — or preparing for one? Start with a free 15-minute Leadership Audit: a no-pressure session designed to help you clarify your next 100 days and lead with presence, not panic.
To schedule your session or learn more about executive coaching, email Henry@365nation.com.
Calling, Not Clout: What Makes a Real Leader
Henry Sanders speaks at the 2022 Wisconsin Leadership Summit. Photo by Hedi Lamarr Rudd
I’m a CEO, executive coach, husband, and father, but one of the most meaningful things I do in my spare time is coach a 14U girls basketball team. Lately, I’ve found myself talking with them less about plays and more about leadership. What it looks like. What it costs. What it actually means.
And the more we talk, the more I notice something: a lot of them — like so many of us — are growing up in a world where leadership looks a lot like clout. The one with the most followers. The one who talks the loudest. The one who gets the most attention. But is that real leadership, or just visibility dressed up as influence?
That question led me to something deeper: What actually makes a great leader in a moment like this? Quietly, I found myself reflecting on what both my experience and my faith say about how we talk about leadership — and how much we get it wrong.
In this age of platforms, personal brands, and public recognition, visibility often gets mistaken for leadership. We equate influence with importance. Clout with calling. The loudest leaders — the ones with the biggest platforms or the most online visibility — often get the most attention. Not because they serve well, but because they trend well. We’ve tied leadership to clout instead of proven impact — and it’s costing us.
But if the last few years have shown us anything, it’s this: Clout might get you in the room. But calling is what keeps you grounded and reminds you why you walked in to begin with.
On top of that, we live in an era where we highlight and obsess over bad leadership more than we lift up the leaders who are doing it right. Across the country, new leaders are rising — younger, more diverse, more ideological. Their lens is political, cultural, and often shaped online. They’re not waiting their turn. They’re already changing the game — for better or worse.
But as the landscape shifts, so does the question: what kind of leadership are we actually encouraging? Leadership, at its best, isn’t about personal elevation. It’s about lifting others — even when no one sees it. It’s about being selfless, putting others before yourself, and helping teammates, coworkers, and communities thrive. But when leadership becomes more about prestige than responsibility, it’s just clout chasing with a title.
As Kendrick Lamar put it: “Clout chasing — hell of a disease, brother.” That line hits harder than ever, because clout is contagious. And in too many circles, it’s become the drug of choice. Clout is loud. It rewards the biggest voices and the most polished profiles. It’s about optics — short bursts of hype, fast-moving attention, and popularity that fades as quickly as it came.
True leadership requires depth. It invites you to wrestle with tough questions, to carry responsibility even when it’s heavy, and to sacrifice for something greater than yourself. The best leaders I know — across race, age, and industry — aren’t necessarily the ones dominating social media platforms. They’re focused on being effective, staying ahead of trends, and building healthy cultures. They mentor young staff, lead with empathy even when it’s not the easiest path, and turn down opportunities that don’t align with their convictions — even if it costs them.
They’re not clout chasing. They’re answering a deeper responsibility — one that asks more of them than it rewards. This moment calls us to rethink what leadership really means — whether you lead a team, a city, a classroom, or just yourself. It challenges us to reimagine leadership as service, not status.
We’ve seen what happens when clout leads — when charisma outpaces results. Institutions unravel. Trust evaporates. People get hurt. And in the rubble, we start craving something more lasting. More rooted. That craving is a clue.
Because the truth is: every great leader isn’t just talented — they’re anchored. Anchored in purpose. Anchored in people. Anchored in principle. They don’t just want to be seen — they want to be useful. They don’t just want influence — they want impact. They don’t chase applause — they answer a calling.
And often, that calling doesn’t come with a title. It comes with a burden. A vision. A quiet, steady pull toward what’s right, even when it’s inconvenient.
At its core, leadership demands honest reflection and purposeful action. You don’t need to be famous to be called to lead. You don’t need to be from a marginalized community to lead with justice. You don’t need to have the biggest platform to make the biggest difference. But you do need clarity and courage. You need an internal compass that keeps bringing you back to the deeper questions: Who am I accountable to when no one’s watching? Who benefits from my leadership? What do I stand for when no one’s clapping?
A better kind of leadership is possible. One that doesn’t rely on noise or image. One rooted in clarity, consistency, and care. The kind that earns trust over time — not through visibility, but through presence. Because what we need now isn’t more leaders chasing platforms. We need more leaders building something that lasts.
Clout fades. But proven impact remains. And calling still matters.
About the Author
Henry Sanders is the CEO of Madison365, founder of the 365 Leadership Summit, and an executive coach who helps leaders build themselves and their teams with clarity and impact.
Ready to lead with purpose, integrity, and real results — not just chase clout? Start with a free 15-minute Leadership Audit: a no-pressure session to help you assess where you are and where you want to grow.
To schedule your session or learn more about executive coaching, email Henry@365nation.com.