The Day I Learned the Difference Between Being Important and Being a Leader

Years ago, I was at a conference where a former U.S. Undersecretary of Defense was giving a talk. He was a man who’d held one of the highest offices in the country, responsible for thousands of lives and billions of dollars. He stood on stage, but his story wasn’t about power or strategy. It was about a cup of coffee.

He told us about the first time he attended that same conference while still in office.

He flew first class. Someone met him at the airport, carried his bags, and escorted him to the venue. Backstage, before he spoke, someone handed him a cup of coffee in a beautiful ceramic mug. He was treated with deference, respect, even a little awe. He was, after all, the Undersecretary of Defense.

A few years later, after he’d left office, he was invited back to the same conference. This time, he flew coach. No one met him at the airport. He carried his own bags. When he arrived backstage, he asked for a cup of coffee. Someone pointed to a coffee machine in the corner. He poured it himself, into a paper cup.

He paused, looked out at the audience, and said, “The ceramic cup was never meant for me. It was meant for the position I held. When I left that position, they gave the cup to the next person. The perks, the attention, the respect—they’re not for us. They’re for the seat we temporarily occupy.”

That story resonated with me. Because it’s so easy, especially as you climb the ladder, to start believing the perks are a reflection of your worth. The corner office, the fancy title, the invitations to speak—they feel good. But they’re not really for you.

They’re for the role you play, the responsibility you carry.

The real test of leadership is what you do when the perks are gone. When you’re pouring your own coffee into a paper cup, do you still show up with humility? Do you still serve? Do you still care about the people around you, even when there’s no applause?

His story reframed leadership as stewardship, not status. It reminded me that the job of a leader is to serve the people and the mission, not your own ego. The perks are fleeting. The impact you have on others… That’s what lasts.

Since then, whenever I find myself enjoying some privilege or recognition, I try to remember the ceramic cup. I ask myself: Am I using this moment to lift others up, or am I just enjoying the view? Am I building something that will outlast me, or am I just collecting perks that will disappear the moment I step aside?

The best leaders I know are the ones who never forget the paper cup.

They’re the ones who give away credit, take responsibility, and serve quietly, even when no one’s watching. They know that leadership is not about being in charge. It’s about taking care of those in your charge.

So, next time you’re handed a ceramic cup, remember: it’s not about you. It’s about the people you serve, and the legacy you leave behind.

And maybe, just maybe, the real mark of leadership is how you act when you’re holding the paper cup.

5 Things Managers Do That Leaders Never Would, According to Simon

Picture this: Two people walk into the same crisis. The project is behind schedule, the client is furious, and the team is falling apart.

The first person immediately starts assigning blame, calls an emergency meeting to “get to the bottom of this,” and sends a tersely worded email about “accountability and expectations.” The second person takes a breath, gathers the team, and says, “This is tough, but we’re in it together. Let’s figure out how to make this right.”

Same crisis. Same pressure. Completely different responses.

It’s a pattern at so many organizations: when the heat is on, people either retreat into management mode or step up into leadership. The difference isn’t about job titles or org charts—it’s about fundamental choices in how we treat people when it matters most.

Simon has spent years studying what separates managers from leaders, and the distinctions are both subtle and profound. Here are five critical differences that reveal whether you’re managing or leading.

1. Managers Hoard Information. Leaders Overshare.

We’ve all worked for that manager who treats information like classified intelligence. They keep key details close to the vest, thinking it gives them power or control. It’s like they’re running a secret club, and you’re not on the guest list.

Simon puts it this way: “A classic manager move: keep key details close to the vest, thinking it gives them power or control… Leaders? They go the opposite way. They’ll walk into a meeting and say, ‘Here’s everything I know, here’s what I don’t, and here’s what keeps me up at night.’ Why? Because trust is built on transparency, not secrecy.”

The contrast is striking. A manager might send out a vague email about a “change in direction” but won’t explain why. A leader calls the team together, lays out the business challenge, and says, “I want your ideas. Here’s what’s at stake.”

Simon’s advice? “Next time you’re tempted to hold back info, ask yourself, ‘What’s the worst that happens if I share this? What’s the best?'”

2. Managers Weaponize Policy. Leaders Bend Rules for People.

Every organization has rules, but how we use them reveals everything about our leadership philosophy. Managers quote the handbook word for word, using policy as a shield to avoid difficult decisions or uncomfortable conversations.

Leaders see it differently. As Simon observes: “Leaders see policies as guardrails, not handcuffs. If someone’s struggling, a leader asks, ‘How can I help you succeed—even if it means flexing the rules?'”

The practical difference is profound. When someone hits a wall, a manager says, “Sorry, you missed the PTO deadline. Nothing I can do.” A leader responds, “You’ve had a rough month. Let’s see if we can make this time off work. I’ll talk to HR with you.”

Simon’s challenge to managers: “When someone hits a wall, don’t just say ‘that’s policy.’ Ask, ‘What’s really going on here, and how can we solve it together?'”

3. Managers “Fire Fast.” Leaders Coach, Then Help People Land Softly.

The business world loves the mantra “hire slow, fire fast,” but Simon has observed a crucial distinction in how managers versus leaders handle departures.

“Managers love the ‘hire slow, fire fast’ mantra,” Simon says. “But leaders know that letting someone go isn’t about making an example—it’s about dignity. I’ve seen leaders spend weeks helping someone find a better fit, even making calls to other companies. They don’t destroy confidence on the way out; they build a bridge to what’s next.”

A manager might say, “You’re not meeting expectations. Today’s your last day.” A leader takes a different approach: “I’ve noticed you’re struggling. Let’s talk about what’s not working. If this isn’t the right fit, I’ll help you find something that is—even if it’s not here.”

Simon’s reframe for anyone facing this situation: “If you have to let someone go, ask, ‘How can I help you find a place where you’ll thrive, even if it’s not here?'”

4. Managers Avoid Hard Conversations. Leaders Run Toward Them.

Perhaps nothing separates managers from leaders more clearly than their relationship with difficult conversations. Managers might sugarcoat, dodge, or hide behind email to avoid discomfort. Leaders understand that avoidance only makes things worse.

Simon’s observation: “Leaders pull people aside and say, ‘This is tough, but I care about you, so let’s talk.’ They know candor is kindness, not cruelty.”

In practice, this looks like a manager noticing tension between team members but saying nothing, hoping it’ll blow over. A leader sits down with both people and says, “This is awkward, but we need to talk about what’s going on. I care about both of you.”

Simon’s practical advice: “Next time you want to avoid a hard talk, say out loud, ‘This is going to be uncomfortable, but it matters.’ Then do it anyway.”

5. Managers Reward Compliance. Leaders Reward Dissent.

Managers love yes-men and yes-women—people who nod along and follow orders without question. Leaders actively seek out the people who will challenge them.

As Simon explains: “Managers love a good yes-man. Leaders? They want the person who says, ‘I think we’re making a mistake.’ Because that’s how you get better.”

The behavior difference is clear: a manager praises the person who always agrees in meetings. A leader publicly thanks the person who says, “I think we’re missing something,” and asks them to elaborate.

Simon once shared a story about a leader who sent a handwritten note to someone who challenged them in a meeting, saying, “Thank you for making us better.” That’s not just surprising. It’s unforgettable.

His advice: “When someone challenges you, say, ‘Thank you. Tell me more.’ Even if it stings.”

The beautiful thing about leadership is that it’s not about your job title or where you sit on the org chart. It’s about the daily choice to see people as humans rather than resources, to build trust rather than demand compliance, and to create an environment where people can do their best work.

Every interaction is an opportunity to lead. The question isn’t whether you have the authority—the question is whether you have the courage.

For more, explore The Optimism Library today. 

One Simple and Effective Leadership Skill Nobody Teaches

Picture walking into a project kickoff meeting where everyone is polite, slightly guarded, and waiting for someone else to break the ice. Or imagine starting a new role where your team is watching to see if you’ll pretend to know everything or admit what you don’t. These moments happen daily in organizations everywhere, yet most leaders have never been taught how to navigate them effectively.

We train leaders to be decisive, confident, and clear—all essential qualities. But we rarely teach them one of the most powerful skills for building trust and accelerating team performance: how to be strategically vulnerable in a way that strengthens rather than weakens their leadership.

Beyond Traditional Leadership Training

At Team Simon, we’re constantly exploring how managers can develop the nuanced skills that can turn them into exceptional leaders. One of the most surprising and impactful skills we teach is something Simon calls “calibrated self-disclosure,” and it has the power to change how leaders build psychological safety without sacrificing authority.

“The skill: calibrated self-disclosure in the first five minutes,” Simon says. “Not radical transparency. Not keeping a stiff upper lip. Calibrated. It’s the leader saying one true, useful thing about their own limits early, tying it directly to the mission, and pairing it with a clear, confident request. Done well, it lowers threat and raises initiative. It makes the room exhale without making the room parent you.”

Simon paints a vivid picture of how this works in practice: “Picture a project kickoff. Everyone’s polite. Slightly guarded. You go first: ‘Quick context before we dive in. The AI piece is new territory for me. My worry is I’ll slow us down by asking basic questions. Our goal is still speed to learning, not speed to launch. Here’s my ask: if I drift into jargon soup, stop me. And if you see a faster path, say it in the moment.’ That’s it. Twenty seconds. Specific fear. Clear why. Concrete request. Confident tone. Then you move on.”

The result, according to Simon, is immediate and powerful: “What happens? People start telling the truth faster. The data scientist admits a dependency risk. The PM raises a timeline constraint. You just bought candor without drama.”

Simon identifies three critical elements that make this approach effective: “First, specificity. Vague confessions invite caretaking. Specific disclosures invite partnership. ‘I’m overwhelmed’ is a burden. ‘I’m behind on approvals; I’ll need 24 hours to respond’ is coordination. Second, sequencing. Do it in the first five minutes, before norms calcify. Whoever goes first sets the edge of what’s sayable. Third, tone. Confident vulnerability. Own the limit without collapsing into it. You’re not asking for permission to be weak. You’re modeling how strong teams talk.”

Why This Skill Is So Powerful

The genius of calibrated self-disclosure lies in what Simon identifies as its surprising nature. “Why it’s surprising: we teach leaders to be clear, not necessarily self-revealing, and when we talk about vulnerability, we swing to extremes,” he says. “Overshare, and you spook the room. Undershare, and you freeze honesty. Calibrated self-disclosure threads the needle. It sends three signals simultaneously: I’m human, I’m responsible, I’m here to serve the goal. That combination builds psychological safety without lowering standards.”

Most leadership training focuses on projecting confidence and authority, which often translates to leaders feeling pressure to appear infallible. But this approach actually creates distance and prevents the kind of honest communication that drives high performance.

Common Pitfalls to Avoid

Simon is clear about the mistakes that can derail this approach: “Common mistakes. Turning it into a monologue. Keep it under thirty seconds. Making it about your feelings without linking to the mission. Always tie your admission to why it matters for the work. Asking for rescue. Don’t do that. Make a crisp request that enables others to contribute. And performing it once, then reverting to perfection theater. Consistency builds trust; a single moment doesn’t.”

The key is understanding that this isn’t about emotional dumping or seeking sympathy. It’s a strategic communication tool that creates conditions for better collaboration and faster problem-solving.

One Framework You Can Use Tomorrow

Simon provides a practical template that any leader can implement immediately:

“A simple template you can use tomorrow,” he explains, breaking it down into five steps:

  1. “Name the context: ‘Before we start…'”
  2. “State the specific limit or fear: ‘I’m likely to…'”
  3. “Tie to the why: ‘Because our goal is…'”
  4. “Make the request: ‘So I need you to…'”
  5. “Reaffirm confidence: ‘If we do that, we’ll…'”

Simon offers a concrete example: “Before we start, quick flag. I haven’t run a launch with this many regulators. I may miss a compliance nuance. Our goal is a clean, on-time approval. So if you hear me skip a step, call it immediately. If we do that, we’ll move fast and stay safe.”

Scaling the Impact

But Simon doesn’t stop at individual application. He sees this as a team skill that compounds when adopted collectively: “Teach your directs to do the same. Start meetings with one calibrated disclosure from the leader, then one from the owner of the riskiest workstream. Two reps. Ninety seconds total. Watch the quality of discussion jump.”

This approach transforms team dynamics by establishing a new norm where honesty and strategic vulnerability become the foundation for high performance rather than barriers to overcome.

What makes this skill so powerful is that it represents a fundamental shift in how we think about leadership authority. Traditional models equate leadership strength with having all the answers. Simon’s approach recognizes that true leadership strength comes from creating conditions where the best answers can emerge from anywhere in the room.

“You’re not asking for permission to be weak,” Simon emphasizes. “You’re modeling how strong teams talk.”

For more ways to level up your leadership skills, be sure to check out more advice in Simon’s Optimism Library

6 Shocking Stats That Prove Middle Managers Are in Crisis

Imagine being promoted to manage people, only to discover you spend less than half your time actually managing them. Picture feeling so unsupported in your role that you’re secretly planning your escape, even as your company depends on you to bridge the gap between senior leadership’s vision and your team’s daily reality.

These are more than hypothetical scenarios. They’re the lived experience of middle managers across industries worldwide. While organizations focus on retaining top talent and developing senior executives, an entire layer of leadership is quietly struggling, burning out, and planning their exit strategies.

At Team Simon, we recently surveyed 971 middle managers across scores of industries around the world. The findings, detailed in our new report, “The Top 10 Things Middle Managers Desperately Need (But Are Afraid to Ask For),” reveal a crisis that most organizations don’t even realize they have.

The data tells a story about colleagues, friends, and perhaps even ourselves—people caught between the ambitions of becoming senior leaders and the daily reality of getting things done with actual humans, all with very little training or support from the companies they work for.

These statistics represent the hidden struggles of the people who make organizations run, and they reveal why so many companies are losing their most valuable asset: the leaders who actually lead. Here are six stats from the report that may change how you view middle management.

1. 75% Are Experiencing Burnout

Making them the most stressed level in any organization

Three out of four middle managers are burning out. Not stressed. Not overwhelmed. Burning out. This isn’t a temporary challenge. It’s a systematic crisis that’s making middle managers the most miserable people in corporate life. They’re absorbing pressure from above while shielding their teams below, all while managing their own emotional overwhelm with little to no support.

Why this matters: Burnout is more than a personal problem. It’s contagious. Research shows that managers account for 70% of variance in employee engagement, meaning burned-out managers create burned-out teams in a cascading effect throughout the organization.

2. They Spend Only 41% of Their Time Actually Managing People

The rest is consumed by administrative tasks

We promote people to management positions, then bury them in spreadsheets, reports, and administrative duties. Middle managers are spending most of their time on tasks that don’t require management expertise, while the actual work of developing people, building culture, and driving performance gets squeezed into the margins.

Why this matters: When managers can’t manage, everything suffers. Teams become directionless, talent goes undeveloped, and the single biggest factor in employee engagement—quality of management—deteriorates.

3. 27.2% Are Actively Working on Their Exit Strategy

More than 1 in 4 are planning their escape

While companies focus on retention strategies, over a quarter of their middle managers are actively looking for the door. These aren’t disgruntled employees. These are the people organizations promoted because of their performance and potential. Yet they see no future at their current companies and are planning their professional escape routes.

Why this matters: Replacing a middle manager costs up to 200% of their salary. When you factor in lost institutional knowledge, team disruption, and the time to rebuild relationships, the true cost is astronomical.

4. Nearly Half (43.2%) Are Fundamentally Disconnected from Work

23.6% feel uninspired, 10.8% actively dislike the culture

This isn’t about having a bad day or needing a vacation. Nearly half of all middle managers have lost their connection to their work entirely. They’re going through the motions while feeling uninspired, dealing with interpersonal conflicts, or actively disliking their company culture.

Why this matters: Disconnected managers create disconnected teams. When the people responsible for motivating others have lost their own motivation, the ripple effects reach every corner of the organization.

5. Self-Confidence Is Both Their #1 Challenge AND Their #1 Goal

27.2% identify building confidence as their most critical need

The irony is staggering: the people we’ve entrusted to lead others feel fundamentally unsure of themselves. Nearly a third of all middle managers report that self-confidence is simultaneously their biggest challenge and their most important goal. They’re expected to project authority and make decisions while secretly feeling like imposters.

Why this matters: Insecure leaders create insecure teams. When managers don’t trust their own judgment, they can’t inspire confidence in others or make the bold decisions that drive business results.

6. Organizations Lose $15.4 Billion Annually Due to Middle Manager Turnover

With replacement costs reaching 200% of departing managers’ salaries

The financial impact is staggering. This isn’t just about the cost of recruiting and training replacements—it’s about the lost productivity, disrupted projects, and damaged team morale that comes when middle managers leave. Yet most organizations continue to treat middle management as a cost center rather than a strategic investment.

Why this matters: The same research shows that organizations with strong middle management see 3-21 times higher returns. The choice isn’t whether to invest in middle managers—it’s whether to profit from that investment or pay the cost of neglecting it.

The Opportunity 

While these statistics paint a grim picture, there’s reason for hope buried in the data. Middle managers aren’t giving up. They’re asking for help. 40% are desperately seeking purpose in their work. 22% want to level up their leadership skills. They’re not just going through the motions; they’re actively seeking meaning and growth.

The organizations that recognize this moment as an opportunity rather than just a crisis will be the ones that emerge stronger. Because when companies invest in developing confident, purpose-driven, well-supported middle managers, everything else gets easier.

If you’re looking for ways you can support your own middle managers, shoot us a note here. And feel free to read the report here

The Leadership Trick That Takes 3 Minutes and Changes Everything

Picture this: You’re a distribution center leader with engagement scores in the basement. Your team feels invisible, disconnected, and frankly, like they’d rather be working anywhere else. But there’s one team in the building that’s different. Their engagement scores are through the roof. They would do anything for their leader.

So what’s her secret?

A notebook and three minutes.

During a recent Live Session for Optimism Library subscribers, leadership researcher Zach Mercurio, Ph.D., revealed a deceptively simple practice he once observed that has the power to profoundly change workplace relationships. The leader in question kept a notebook where every Friday, she’d write down her team members’ names and note one thing each person mentioned during the week—a struggle, a complaint, something they were worried about.

Come Monday morning, she’d check in: “Hey, I remember that equipment wasn’t working for you last week. Did we get that fixed?” Or: “You seemed nervous about that meeting. How did it go?”

As she told Mercurio: “There’s magic in being remembered.”

Why This Works (And Why We Usually Don’t Do It)

The science backs this up. When someone shows us we matter through remembering details about our lives, it releases oxytocin—the trust hormone. But here’s the kicker: most of us are terrible at doing this naturally. We’re too busy, too hurried, too focused on the “what” and “how” of our work to remember the “who.”

As Mercurio explained, “Hurry and care can’t coexist.” When we’re rushing from meeting to meeting, multitasking during calls, or racing through our email backlog, we miss these opportunities for connection.

Making It Practical: Your Monday Morning Game-Changer

Here’s how to implement this practice starting tomorrow:

  1. Ask better questions: Instead of “How are you?” try “What has your attention today?” or “What’s been taking your energy this week?” These questions actually get answers.
  2. Actually listen: When someone shares something – their kid’s soccer game, a presentation they’re nervous about, a project that’s frustrating them – mentally note it. Better yet, jot it down after the conversation.
  3. Follow up: This is where the magic happens. Next time you see them, reference what they shared. “How did Jamie’s soccer tournament go?” “Did that presentation go as well as I knew it would?”

The Trust Fall Myth

Here’s something interesting that came up during the Q&A: Remember those corporate trust falls and team-building exercises? Mercurio had some thoughts on those, too. The problem isn’t the trust fall itself—it’s when your daily reality doesn’t match the symbol.

“No amount of symbolic action, ritual, platform, program, perk, or promotion can make up for daily interactions in which you don’t feel that you matter,” he said.

In other words, skip the trust falls. Do the check-ins instead.

But What If You’re Too Busy?

One Q&A participant asked the question we’re all thinking: “How do you find time for this when you’re swamped?”

Mercurio’s response was perfect: “Name one financial metric that is not impacted by a human being and how they feel.”

After all, even automated sales through a website originate with a person.

The truth is, we often underestimate our impact. Research shows we consistently undervalue how much small gestures mean to others. That quick check-in you think is too minor to matter? It might be the thing that keeps someone engaged, productive, and loyal to your team.

Start Small, Start Tomorrow

You don’t need to revolutionize your leadership style overnight. You just need to remember one thing about one person and follow up on it. That’s it. Three minutes on Monday morning to show someone they’re not invisible.

As that distribution center leader discovered, there really is magic in being remembered. And unlike trust falls, potluck lunches, or employee of the month programs, this one actually works.

Because at the end of the day, people don’t need another pizza party. They need to know they matter. And sometimes, all that takes is someone remembering to ask about their kid’s soccer game.

Want to be the type of leader people want to work for? Explore Simon’s Optimism Library today.

Would You Still Lead If No One Ever Knew Your Name?

There’s a story I love to tell about leadership, but it doesn’t start with a CEO or a general. It starts with someone you’ve probably never heard of—the person who holds the elevator when your hands are full, who notices when you’re struggling and quietly asks, “Are you okay?” The person who makes the coffee and remembers birthdays, who gives away credit and takes responsibility when things go wrong. The person who leads, not because of a title, but because of a choice.

We live in a world obsessed with recognition. Social media, awards, promotions—they all tell us that leadership is about being seen, being celebrated, being known. But real leadership, the kind that changes lives and shapes cultures, often happens in the shadows. It’s the leadership of service, humility, and courage. The kind that asks: would you still lead if no one ever knew your name?

Let’s be honest. That’s a hard question. Most of us want to be noticed. We want our efforts to matter, to be acknowledged. But the best leaders I’ve ever met are the ones who don’t need the spotlight. They’re the ones who understand that leadership is the awesome responsibility to see those around us rise. It’s not about rank or authority. It’s about caring for the person to your left and the person to your right. It’s about making the choice, every day, to help others succeed, even if no one is watching.

I’ve seen this kind of leadership everywhere. In the nurse who stays late to comfort a patient. In the teammate who covers a shift so someone else can go to their kid’s recital. In the manager who listens—really listens—when someone is struggling. These are not grand gestures. They’re small, consistent acts of service. And over time, they build something extraordinary: trust.

Trust is the currency of leadership. It’s what makes people feel safe, valued, and willing to take risks. When we lead without needing recognition, we create a “Circle of Safety”—a space where people know someone has their back. That’s when teams thrive. That’s when innovation happens. That’s when people go home at the end of the day feeling fulfilled, not just employed.

But here’s the thing: this kind of leadership is hard. It’s often thankless, sometimes lonely, and almost always invisible. If everything goes right, you give away all the credit. If everything goes wrong, you take all the blame. It’s like parenting in that way—exhausting, frustrating, and full of moments where you wonder if anyone even notices. But then, out of nowhere, you catch a glimpse of what you’ve built. A team that rallies together. A colleague who steps up for someone else. A culture where people feel safe to be themselves. Those are the glimmers that make it all worth it.

So why do it? Why lead if no one ever knows your name? Because leadership isn’t about you. It’s about the people you serve. It’s about the legacy you leave, not in headlines or awards, but in the lives you touch. The best leaders I know are students of leadership. They’re always learning, always growing, always looking for ways to help others rise. They know there’s no such thing as an expert leader—just like there’s no such thing as a perfect parent. We’re all figuring it out as we go.

And here’s the paradox: the more you focus on serving others, the more your influence grows. Not because people know your name, but because they trust you. They follow you. They become leaders themselves. That’s how cultures change. That’s how movements start. Not with a single charismatic figure, but with countless quiet acts of courage and care.

If you want to lead—really lead—start small. Hold the door. Make the coffee. Ask, “How can I help?” And mean it. Look for the person who’s struggling and offer a hand, not because you’ll get credit, but because it’s the right thing to do. Build trust, one act at a time. Create a Circle of Safety for those around you. And remember: leadership is a practice, not a position. It’s a choice you make, every day.

The 3 Skills 57% of Middle Managers Are Desperately Missing

The story plays out everywhere: brilliant individual contributors get promoted to manage people with nothing more than “figure it out as you go.”

No wonder middle managers are the most miserable people in any organization. That’s not our opinion. It’s theirs.

We surveyed 971 middle managers worldwide for our new report, “The Top 10 Things Middle Managers Desperately Need (But Are Afraid to Ask For).” The findings were heartbreaking: 57% are actively struggling with fundamental leadership capabilities that were never part of their training.

They spend just 41% of their time on actual people management. The rest? Administrative busywork.

But here’s the hope: they’re hungry for growth. They want to be the leaders their teams need. They just need someone to show them how.

Our research identified three critical skill gaps that, once addressed, transform both manager confidence and team performance. 

The 3 Skills That Change Everything

1. Human-Centered Communication

The skill 55% struggle with most

This is about more than writing better emails. It’s about the conversations that keep managers awake at 2 AM:

– How do you correct someone without crushing their spirit?

– How do you motivate someone who’s checked out?

– How do you disagree with your boss without career suicide?

Most learn through trial and error, leaving damaged relationships behind. Managers see themselves as “coaches,” yet reality forces them into taskmaster roles, buried in spreadsheets instead of building people.

In practice: Master courageous conversations. Deliver feedback that grows people. Create psychological safety where team members feel heard and valued. (If you’re looking to level up skills like these, feel free to explore The Optimism Library, home to all of Simon’s great leadership frameworks.)

2. Virtual and Hybrid Leadership

The challenge facing 43.4% of managers

Hybrid work changed everything about managing people. Most managers still apply in-person techniques to virtual environments, creating “productivity paranoia”—disconnected leaders who micromanage and erode trust.

“Management by walking around” dies when half your team works from different locations. Managers need new frameworks for building culture, maintaining performance, and fostering relationships across screens and time zones.

In practice: Master “management by checking in”—frequent, shorter, purpose-driven conversations. Read virtual body language. Facilitate engaging online meetings. Create rituals that maintain team connection across distances.

3. Emotional Intelligence and Resilience

The foundation 75% are missing

The most overlooked skill: managing your own emotional state while helping others navigate theirs. Our research shows 75% of middle managers experience burnout—making them the most stressed level in any organization. Nearly half (43.2%) feel fundamentally disconnected from work.

When managers can’t handle their own overwhelm, they can’t support their teams. This cascades downward: Gallup research confirms managers account for 70% of variance in employee engagement.

In practice: Build stress management systems beyond “take a deep breath.” Learn to absorb pressure from above while shielding teams below. Develop emotional stamina for leading people through uncertainty.

The Path Forward

Middle managers aren’t asking for miracles. They want practical training in the human side of leadership. Skills that can be learned, practiced, and mastered with the right support.

Organizations that see this as opportunity, not crisis, will win. When companies invest in developing these capabilities, they see dramatic improvements: better strategy execution, stronger culture, higher retention, improved results.

The question isn’t whether your middle managers need these skills—the research proves they do. The question is whether your organization will provide the support they need.

Because when you have confident, emotionally intelligent, communication-savvy middle managers, everything gets easier. Strategy gets implemented. Culture strengthens. People stay. Results soar.

The potential is already there.

We just need to notice it.

No One Learns to Swim on the Shore

We all know how to do something completely new if we absolutely have to.

When we or a family member is diagnosed with an illness, for example, we talk to doctors and do research and become quite well-versed in the relevant medical science.

If we do a renovation to our home, we become quite fluent in construction terms.

In both cases, we wouldn’t seek out this knowledge or even think we could learn it as quickly as we do until we have to learn it. And we do more than learn it. In many cases, we get good at. We find new ways of solving problems, ways the experts never thought of.

Entrepreneurs do the same thing, the only difference is, they do it by choice.

When an entrepreneur with no prior experience in manufacturing clothing decides to open a clothing business, they fast learn about supply chain and how clothing is made.

When an entrepreneur with no prior knowledge opens a cookie company, that have to learn about food regulations, what ingredients are shelf stable and industrial food manufacturing.

In all these cases, the people involved, at some point, will say to a friend, “I never expected to know so much about….”

So for anyone who thinks they don’t have what it takes to do something wildly new or different, it turns out, we’ve all got that ability in us already. The only difference is if you want to learn to swim when someone pushes you in the pull or when you decide to jump in yourself.

What Most Leaders Miss When Looking at Their Data

Have you ever noticed how easily numbers can replace people in our conversations at work?

“We need to improve customer satisfaction by 20%.” “Our retention metrics are down this quarter.” “The data shows we’re losing market share.”

These statements represent valuable business insights. And according to Simon, complementing them with the human element can elevate your leadership to extraordinary levels.

The Human Behind the Number

During a recent talk at Brandeis University, Simon shared a powerful story that perfectly captures one of his most compelling leadership insights:

A university was running a scholarship fundraising campaign with volunteers making phone calls to potential donors. The results were disappointing—numbers were flat or declining despite their best efforts.

Then, something remarkable happened.

The organizers brought in a scholarship recipient—let’s call her Stacy—to speak to the volunteers for just five minutes. Stacy shared how the scholarship had changed her life, the opportunities it created, and the profound impact it had on her future.

What happened next? The fundraising numbers skyrocketed.

Why? Because suddenly, the volunteers weren’t just dialing for abstract “dollars” or “metrics.” As Simon explained, “They were doing it for Stacy over there. I’m calling you because I’m damn well going to get more money for people like Stacy. And it became deeply personal.”

The Opportunity of Ethical Clarity

This story illustrates what Simon calls “ethical fading”—a pattern Simon identifies where leaders can benefit from reconnecting with the human impact of their business decisions.

“Ethical fading is when people make decisions while still believing they are within their own ethical framework,” Simon explained.

We see this opportunity for greater ethical clarity when pharmaceutical companies describe pricing changes as “optimizing pricing strategy” or when financial institutions focus exclusively on “meeting sales objectives.”

The business language we often use—externalities, optimization, metrics—presents an opportunity to bridge the gap between our decisions and their human impact.

The Simple Practice That Changes Everything

The solution Simon offers is beautifully straightforward and powerful: Put a human face on your data points.

Here’s how you can implement this practice starting today:

  1. Invite customers to team meetings: Have a real customer share how your product or service impacted their life, either in person or through video.
  2. Create “impact moments:” Share specific stories of how your work affected someone, not just aggregate satisfaction scores.
  3. Use names alongside numbers: When discussing data, connect it to individuals: “This means we can help 270 people like Sarah access healthcare next month.”
  4. Reimagine your metrics: For every performance indicator you track, ask: “What’s the human story behind this number?”
  5. Field visits: Regularly get your team out to meet the people they serve, whether customers, patients, students, or communities.

The Ripple Effect of Rehumanizing Leadership

When you consistently connect your team to the humans behind their work, remarkable things happen:

  1. Performance improves: Like those scholarship fundraisers, your team becomes motivated by purpose, not just metrics.
  2. Ethical decision-making strengthens: It’s much harder to make choices that harm people when you can picture their faces.
  3. Innovation flourishes: Understanding real human needs sparks creative solutions that data alone might miss.
  4. Team cohesion deepens: Shared purpose creates stronger bonds than shared targets ever could.

A Leadership Challenge for You

This week, try this simple experiment: Before your next team meeting, find one story that illustrates the human impact of your work. Share it at the beginning of the meeting, then notice how it shapes the conversation that follows.

Does decision-making feel different? Does problem-solving take on new dimensions? Does the energy in the room shift?

As Simon reminds us, leadership thrives when we focus on serving people alongside managing metrics. When we connect with the humans behind our data, we become both better leaders and better humans ourselves.

And in a world increasingly dominated by algorithms and analytics, that might be the most important leadership skill of all.

Curiosity is essential
                for progress.
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A spark is something quite small and, by itself, not very powerful. But a spark has the ability to ignite. An idea is like a spark; alone it is just a set of words, but it too can ignite. A great idea can inspire others to dream bigger. Let us all work together to ignite something greater than ourselves.

Let us all be a Spark of Optimism.