Simon Sinek - Page 3 - The Optimism Company

Why Boredom Is a Leader’s Best Friend

Posted on January 9, 2026January 9, 2026 by Team Simon

Here’s a question for you: When was the last time you were truly bored?

Not frustrated. Not waiting in line scrolling through your phone. Not filling every micro-moment with a podcast or email check. But genuinely, profoundly bored—staring at nothing, thinking about everything, with no agenda whatsoever.

If you’re like most leaders, the answer is probably “I can’t remember.” And that’s precisely the problem.

At Team Simon, we love studying what makes great leaders great. We’ve explored the power of purpose, the infinite mindset, and why leaders eat last. But one of the most counterintuitive insights we’ve encountered is this: boredom itself is essential to visionary leadership.

The Boredom Walks That Changed Everything

Simon discovered this recently through a conversation with Elle Cordova, a polymath who transformed lockdown isolation into viral poetry and music. Elle shared her secret weapon with him: “boredom walks.”

“She calls them ‘boredom walks,'” Simon says, “leaving the phone behind to let ideas bubble up.” No destination. No podcast. No productivity goals. Just walking and being present with whatever thoughts emerge.

In our hyper-connected, hyper-productive world, this sounds almost rebellious. But here’s what Elle understood: creativity doesn’t happen in the frenzy. It happens in the gaps.

The Wisdom of Sitting Still

Simon shares another formative experience: “I once got advice to go to Central Park, grab a coffee, sit on a bench, and just watch people for an hour. No agenda, no notes. It sounded absurd at the time, but he was right.”

Think about what that advice required: giving up an hour of “productive” time to do absolutely nothing measurable. For most leaders, that sounds impossible. Our calendars are packed. Our teams need us. There’s always another fire to put out.

But that’s exactly why boredom is so powerful. It creates space for rumination—the kind where your brain connects dots it couldn’t under pressure.

Why We’re Addicted to Busyness

Remembering his conversation with Elle, Simon says, “we laughed about America’s ‘vomit reaction’ to boredom. We’re addicted to stimulation, convinced idle time is wasted.”

This addiction isn’t accidental. Our brains crave the dopamine hit of busyness—the ping of a notification, the satisfaction of checking off a task, the feeling of being needed. We’ve built entire cultures around glorifying “the hustle” and wearing exhaustion as a badge of honor.

But here’s what we’re missing: in a world of AI and endless productivity tools, human innovation comes from what machines can’t replicate—curious, unstructured thought.

Elle learned card counting for blackjack not from apps, but from daydreaming about probabilities. When Simon struggled writing Leaders Eat Last, it wasn’t another meeting or research session that unlocked his breakthrough. “A walk in New York and a friend’s call pulled me through,” he recalls. Boredom forced the clarity.

What Boredom Does for Leadership

A bored leader is a reflective leader. And reflection is where transformation happens.

When you create space for boredom, you:

Reconnect with your WHY: The daily grind can obscure your deeper purpose. Boredom strips away the noise so you can hear what truly matters again.

See patterns others miss: Your brain needs idle time to process information and connect seemingly unrelated ideas. Innovation lives in those connections.

Shift from reactive to visionary: You’re not just responding to the urgent—you’re envisioning what’s possible.

Model trust and confidence: Teams follow leaders who have the courage to pause and think deeply, not just react constantly.

Without boredom, we default to finite games—chasing short-term wins and metrics over meaning. But when you embrace the infinite mindset, boredom becomes your ally for trust-building and innovation.

One Leadership Habit That Will Transform Your 2026

Posted on December 23, 2025December 23, 2025 by Team Simon

Imagine a world where work doesn’t drain us, but fills us. Where Monday mornings feel like possibility, not punishment. Where we don’t just tolerate our teammates, we’d go to battle for them. That world exists. And it starts with the choice to stop building teams of stars and start building teams that trust.

There’s a stat Simon loves to cite, and it reveals everything about what makes teams truly great: teams of average performers consistently beat teams of high performers. Not sometimes. Consistently.

We obsess over hiring stars, the top 1% individuals with killer résumés and metrics. We chase the people who shine brightest in interviews, who have the most impressive achievements listed on LinkedIn. But here’s what happens when you stack them together without trust: they fracture. They compete internally, hoard wins, focus on personal glory.

Average folks? They prioritize the team. They serve each other, share credit, cover weaknesses. That’s the secret sauce for real outperformance.

Simon has seen it in action with groups he’s studied. The “stars” burn bright alone but dim in ensembles. The everyday players, bonded by mutual devotion, win marathons.

Why This Matters Now

We’re entering 2026 carrying the weight of years that asked too much. We’re tired. Our teams are tired. And in that exhaustion, there’s a temptation to look for the hero, the superstar who’ll save us all.

But salvation doesn’t come from one brilliant person. It comes from many good people choosing each other, again and again.

When Simon taught, he stacked his top performers on one team. They fought over credit, complained about slackers in his office. “My grade, my work,” they’d say. The average team? They covered for each other, focused on the group grade. They won every time because they trusted, they teamed.

Why does this surprise us? Because our metrics worship individuals. We celebrate the person who closed the biggest deal, hit their numbers, got the promotion. But leadership’s job isn’t to crown winners. It’s to build the container for collective magic. It’s to create the space where people feel safe enough to serve something bigger than themselves.

The Habit: Ask One Question Every Time

Here’s the one leadership habit that will transform your 2026, and it’s beautifully simple: every time someone on your team has a win, ask them one question: “Who helped you?”

Not as an afterthought. Not casually. But as the first response to every success.

Then, and this is critical, publicly recognize those helpers by name. In the team meeting. In the Slack channel. In the email to leadership. Make the assist as visible as the goal.

When Elizabeth closes the big client, don’t just celebrate Elizabeth. Ask her, “Who helped you?” Then send a message: “Elizabeth landed this client, and she says it wouldn’t have happened without Jake’s research, Maria’s introduction, and Tom covering her other accounts. That’s what winning looks like here.”

Do this every single week. Every win. Every milestone. Every success.

Watch what happens.

People will start helping each other more because they know it will be seen. They’ll stop hoarding information because collaboration gets recognized. The quiet contributors, the ones who always made others better but never got noticed, will finally feel valued. And your stars? The good ones will lean into it. They’ll realize their legacy isn’t what they achieved alone, but who they brought up with them.

What Changes

This one question reshapes everything. It shifts you from scorekeeper to culture guardian. It changes what people compete for. Instead of fighting over individual glory, they’ll compete to be the person others name when asked who helped.

You’re teaching your team what you value. And when you consistently value mutual devotion over individual brilliance, you build the trust where average people choose to serve each other. That’s how you create a real team, not just a group working together.

Teams that trust outperform every time.

The Choice Ahead

As we head into 2026, most leaders will keep doing what they’ve always done. They’ll chase the next superstar hire. They’ll celebrate individual metrics. They’ll wonder why their talented teams underperform.

You can choose differently.

You can be the leader who builds something rare: a team that actually cares about each other. Where people show up not just for the paycheck, but for the people. Where the work matters because we’re doing it together.

“Leadership is not about being in charge,” Simon says. “Leadership is about taking care of those in your charge.”

Your team doesn’t need more stars. They need you to see the constellation they’re already forming. They need you to illuminate the connections between them, to make visible all the quiet acts of service that make the magic possible.

One question. Every win. “Who helped you?”

That’s how you transform 2026. That’s how you build the world where work fills us instead of draining us.

What to Do When You’re Great at Your Job But Terrible at Meetings

Posted on December 19, 2025December 19, 2025 by Team Simon

You know your stuff. Hand you a technical challenge, a system that needs fixing, a problem that keeps others up at night, and you’re brilliant. Your work speaks for itself.

But then there’s the meeting.

You walk in prepared. You have ideas. You know what needs to happen. But the moment the conversation starts, something shifts. Your mind races. Should I say this now? Will it sound stupid? By the time you work up the courage to speak, the moment has passed. Someone else said what you were thinking—only they said it with confidence.

You leave feeling invisible.

Here’s the truth: Being great at your job and being heard in meetings require different skills. And the good news? Skills can be learned.

Being great at your job means solving problems. But meetings are about shaping problems with others. It’s a shift from finding answers alone to building them together. From proving competence to serving the room.

This isn’t a weakness to fix. It’s simply the next skill to practice.

The First Thing to Do

Stop trying to prove you belong there. That frame puts all the pressure on performance instead of contribution.

Shift from proving yourself to serving the room.

Before your next meeting, write one line: “My job here is to help us decide X faster and better.” Maybe it’s clarifying the problem. Maybe it’s surfacing a risk no one’s named. Whatever it is, name it.

This isn’t about you. It’s about what the team needs. And when you serve something bigger than yourself, the fear gets smaller.

In the Room: Ground, Then Contribute

Your nervous system can’t tell the difference between a high-stakes meeting and a physical threat. That’s why your heart races and your brain goes blank right when you need it most.

Here’s your reset: Feet flat. Slow exhale. Look around the room once. Your nervous system listens to your body. When you ground yourself physically, your mind follows.

Then speak early, even if it’s small. “Success today looks like leaving with two clear decisions and owners.” That’s it. You’re in the conversation now, not watching it happen without you.

When the Spiral Starts

Mid-meeting, the voice comes: That sounded dumb. Everyone’s judging me. I should stay quiet.

Here’s the move: shift from performance to service.

Ask out loud: “What would good look like from here?”

Watch what happens. People respond. The conversation moves forward. And you realize no one was judging you—they were waiting for someone to say something useful.

Or try this when uncertainty hits: “I may be missing something. Here’s what I see. What am I not seeing?”

This isn’t weakness. This is confident doubt, and it earns more trust than false certainty ever could.

To Be Heard: Make Your Ideas Travel

The difference between ideas that land and ideas that disappear isn’t charisma. It’s clarity.

Give people three things: the problem, the picture, the path.

“Onboarding takes three weeks too long. If new hires could do X by day five, we’d cut that by half. Let’s pilot a new system that can get us there.”

Clear beats clever. Every time.

After the Meeting: Build Your Reputation

Send a three-line recap: decision, owners, next check-in. Reliability creates presence. When people can count on you, authority grows quietly.

Then reflect for sixty seconds: What landed? What muddied? What will I try differently next time?

This is how you close the gap—not by being perfect, but by learning faster than everyone else.

You’ll Know It’s Working When…

You speak earlier with fewer words. People start asking you to frame decisions. Disagreements feel productive, not personal. You leave meetings tired but clear.

Leadership isn’t about being comfortable. It’s about being effective. And sometimes that’s exhausting. But that exhaustion means you showed up. You served. You led.

Start Small, Start Now

Your next meeting: bring one expanding question and one narrowing statement. Use them in the first ten minutes.

“What assumptions are we making that might be wrong?”
“Given that, what decision are we actually making today?”

You don’t have to transform overnight. You just have to show up a little braver than yesterday.

For more advice on being the leader you wish you had, explore The Optimism Library today.

5 “Terrible” Leadership Tips That Totally Work

Posted on December 12, 2025December 12, 2025 by Team Simon

Every leader faces a choice: do we manage people, or do we develop them? Do we extract performance, or do we inspire it? Do we build teams that need us, or teams that don’t?

The conventional wisdom has clear answers. Stay in control. Lead with data. Keep emotions out of it. Fix weaknesses. Beat the competition.

But here’s what we’re learning: the path to extraordinary leadership oftentimes runs directly through practices that sound completely wrong. Practices that make us uncomfortable. Practices that challenge every instinct we’ve been taught to trust.

With Simon’s insights and the latest research, we’ve identified five leadership approaches that people dismiss as reckless but that consistently create remarkable teams. Here’s what we discovered.

1. Leave Your Team Hanging When Asked Questions

This sounds like abandonment. Like leaving people stranded when they need you most.

But here’s the deeper truth: “When someone asks, ‘What should I do?'” Simon tells us, “Instead of answering them outright, try answering their question with a question: ‘What do you think?’ Then listen. If their choice is reasonable, back it. If it misses the mark, ask further questions.”

Why does this matter? Because leadership isn’t about having all the answers. It’s about building people who don’t need you to have all the answers.

Every time you say, “What do you think?,” you’re saying something far more powerful: “I believe in you.” And that belief becomes the foundation they stand on when you’re not in the room. This is how you build leaders, not followers.

2. Talk About Feelings at Work

This feels dangerous. Like opening Pandora’s box when you should be keeping things professional.

But research from Stanford’s Graduate School of Business reveals something profound. When leaders say, “You seem frustrated,” or, “I notice you’re upset,” trust skyrockets. The researchers found across six studies that emotional acknowledgment dramatically elevated trust, especially for negative emotions.

Why? Because people desperately need to know they’re not invisible. That their struggle matters. That someone sees them as a whole human being, not just a productivity unit.

When you name what you see, you’re saying: your humanity is welcome here. And when people feel their humanity is welcome, they bring their creativity, passion, and best work.

3. Be Soft on Performance

This feels like you’re avoiding accountability.

But consider why we’re here in the first place. “When someone misses a target,” Simon says, “start with care: ‘Are you okay? I’m concerned about you.’ Create safety first. Only then explore performance.”

Remember that people aren’t machines. They’re human beings trying to do good work while navigating a world that never stops throwing curveballs.

When you lead with, “You missed the number,” you’ll get defensiveness. When you lead with, “Are you okay?,” you get truth. And truth is the only thing that leads to real solutions.

4. Admit Your Competition Is Simply Better Than You

This feels like surrender. Like admitting defeat before the game even starts.

But Simon sees it differently: “Name the competitor who gets under your skin. Then identify one thing they consistently do better. Turn that into your next improvement sprint.”

Why does this help? Because the finite game (the one where you obsess over crushing your competition) has a ceiling. But the infinite game has no ceiling. When you stop competing to win and start competing to improve, you unlock humility that makes you teachable, curiosity that makes you innovative, and growth that never stops.

“Worthy rivals make us sharper, humbler, and more inventive,” Simon adds. They’re not obstacles. They’re mirrors showing us who we could become.

5. Stop Trying to Fix Weaknesses

This sounds irresponsible. Like ignoring problems until they become disasters.

But research from Zenger Folkman, analyzing over 100,000 leaders, reveals a fascinating truth: unless someone has a critical flaw, extraordinary performance comes from building strengths, not fixing weaknesses.

When you spend energy turning someone’s 4 into a 6, you’re telling them: “You’re not enough.” But when you invest in turning their 7 into a 9, you’re saying: “I see your gifts. Let’s make them undeniable.”

According to Gallup research, employees who use their strengths daily are six times more likely to be engaged. Not because they’re avoiding hard things, but because they’re doing work that energizes rather than drains them. People who are empowered to be excellent at what they’re naturally good at don’t need motivation. They need opportunity.

The Friends Who Drive You Crazy Are Actually the Ones You Need Most

Posted on November 19, 2025November 19, 2025 by Team Simon

Here’s something worth celebrating: the richest, most meaningful friendships in your life probably aren’t with people who are just like you.

Think about it. Your closest friend, the one who really gets you, is probably someone who drives you a little crazy sometimes. Who sees the world completely differently. Who makes you laugh at yourself. Who pushes you to be better without even trying.

And that’s not a coincidence. That’s the magic of friendship.

We live in a world designed to surround us with sameness. Algorithms show us more of what we already like. We gravitate toward people who think like us, laugh at the same jokes, share our worldview. It’s comfortable. It’s validating. It’s easy.

But easy doesn’t make us grow. And comfortable doesn’t make us come alive.

The best friendships? They happen when we stop looking for people who are just like us and start getting curious about people who aren’t.

The Friend Who Changed Everything

Swedish author Fredrik Backman knows this better than most. On a recent episode of A Bit of Optimism, the bestselling author of A Man Called Ove and Anxious People shared the story of a friendship that changed his life. A 30-year friendship built not on common ground, but on profound difference.

Backman’s best friend Riyadh couldn’t be more different from him. Fredrik is introverted and academic. Riyadh is extroverted and practical. Fredrik avoids people. Riyadh loves them. Fredrik gets lost in his head. Riyadh leads with natural charisma.

They’re opposites in almost every way that matters.

And yet, for over three decades, this unlikely pairing has been one of the most important relationships in both their lives.

“I was fortunate in the way that I stumbled upon people early on in my life that were very different from me,” Backman said. “And I found out very quickly that that was a good thing for me. I needed people who were not like me so that I could look at their best qualities and strive for them.”

Here’s the beautiful thing he learned: the people who annoy us most are often reflections of ourselves.

Backman once complained about how irritating certain people were at airports. His wife and kids were quick to point out the uncomfortable truth: “That’s how you are when you’re having a bad day. That’s how you are when you’re annoyed by something.”

When we only befriend people like us, we create an echo chamber that reinforces our existing patterns, both good and bad. We miss opportunities to grow, to be challenged, to see our blind spots through fresh eyes.

“If you hang out with people who are very different from you, you kind of learn how to make jokes about how different you are,” Backman explained. “You understand the way that you are different from the people around you.”

And perhaps most importantly: “You’re never bored.”

The Work of Understanding (And Why It’s Worth It)

Now, let’s be honest. Befriending people different from you isn’t always a walk in the park. Backman is refreshingly candid about this, both with his best friend and with his wife, who he describes as “very, very, very different” from him.

“We disagree a lot,” he admitted. “She’s way more extroverted. Very different people. We like different things.”

But the work required to bridge those differences creates something stronger than easy compatibility ever could.

Backman and his wife developed what they call “rules of fighting.”

These are boundaries about what they couldn’t say even in heated moments, because some words do damage that can’t be undone. After every argument, they’d spend hours talking through what happened, what hurt, what worked, and what needed to change.

“The work is not on the relationship,” Backman said. “The work is on you. I have to work on who I am, communicating better, explaining my feelings better, understanding me better so that I can explain myself better.”

This applies just as much to friendships. When we befriend people unlike us, we can’t coast on assumed understanding. We have to articulate our feelings, question our assumptions, and genuinely try to see through another person’s eyes.

That effort, that work on ourselves, makes us better people. And that’s a gift.

How to Find Your Unlikely Friends

If you’re wondering how to put this into practice, Backman’s advice is refreshingly simple: stop looking for people like you.

“Don’t go looking for the ones that you have the most in common with,” he said. “Go look for the ones who are different.”

This might mean:

Striking up a conversation with the colleague whose approach to work baffles you
Accepting an invitation from the neighbor who seems to run on a completely different frequency
Joining a group or class where you’ll be the outsider, not the insider
Staying curious about the friend of a friend who challenges your perspectives

It also means resisting the algorithms. Social media wants to show you more of what you already like. Dating apps want to match you with people who check your boxes. Even our neighborhoods and workplaces can become echo chambers if we’re not careful.

The best friendships, Backman suggests, aren’t found through optimization. They’re stumbled upon through openness.

Choose to Be the Friend You Want

When Backman described his friendships as “lucky,” Simon pushed back gently. After hearing how much work, communication, and intention went into maintaining them, Simon reframed it:

“I think the way you get one of those friends that you want is you choose to be that friend first.”

Backman became the friend he is because he chose to surround himself with people who challenged him to grow.

“The best relationships, the best marriages, the best friendships that I can think of around me are people who are very, very different from each other,” Backman observed.

Not because difference is easy. But because it’s worth it.

And in the end, those are the people you can’t imagine life without.

How to Actually Teach People to Care, According to a CEO Who Figured It Out

Posted on November 5, 2025November 5, 2025 by Team Simon

Many years ago, Bob Chapman sat in the pews of a wedding ceremony, watching a father walk his daughter down the aisle. Most people see a beautiful tradition. Bob saw something that would transform his company.

“A father who would give his life for his precious child was giving her away to another man with the hope that he will take care of her with the same love,” Bob tells Simon in the latest episode of A Bit of Optimism. “That’s when it struck me: Every single person who works in my company is someone’s son or someone’s daughter. Every employee is someone’s precious child who’s now in my care.”

Bob Chapman is the CEO of Barry-Wehmiller, a $3.6 billion manufacturing company. Before that wedding, he’d been trained as an accountant and ran his business like one. “People were functions for my success,” he admits. “I was a nice guy. We had a nice company, but I saw people as functions.”

That wedding changed everything. And what Bob discovered over the next twenty-plus years is this: “Caring is a teachable skill.”

Which may like corporate BS until you meet someone like Randall.

The Angriest Guy in the Building

When Barry-Wehmiller acquired Randall’s company in the early 2000s, he was deeply skeptical about his new bosses. “Just about everything” Bob said made him roll his eyes. “I just want to do my job,” Randall tells Simon. “Just leave me alone and pay me fairly.”

Randall wasn’t just cynical. He was angry. “I didn’t like anybody,” he says. “An engineer once told me I turned him around at 50 feet just by looking at him.” He’d literally built walls of steel around his work area to keep people away.

Today? Randall is one of the top-rated professors at Barry-Wehmiller University, teaching the communication and leadership skills he once dismissed as nonsense.

So how did they transform someone that angry? And more importantly, how did Bob build a system that could do this at scale across a company of 12,000 people?

How Randall Changed (And What It Reveals About Teaching Caring)

They showed up every single day. Two Barry-Wehmiller leaders came by Randall’s work area daily to say hello. Every day, Randall ignored them. “But they were so persistent,” Randall says. “Day after day.”

One day, one of them literally crawled over the steel barriers Randall had built around his workspace just to say good morning.

“I was stunned,” Randall says. “But that was the start of it.”

They didn’t call it “caring training.” Eventually, Randall signed up for an in-house course called “Communication Skills.” Not empathy training. Not “be a better human.” Just practical communication.

“This isn’t communication skills,” Randall realized halfway through. “This is self-reflection.”

The course didn’t ask Randall to change his values. It taught him concrete skills—listening, communication, self-awareness—and let him discover caring through competence.

The Broader System: 4 Principles That Make Caring Teachable

Randall’s transformation wasn’t a fluke. Bob built an entire system around making caring teachable and sustainable. Here’s how it works:

Model it relentlessly. You can’t teach caring in a classroom if leaders don’t model it in the hallways. Those two leaders crawling over steel barriers? That’s the real curriculum.
Make it skills-based, not values-based. Barry-Wehmiller built their own university. Not for product training. For “human skills”—communication, listening, self-reflection. “You can’t ask people to care,” Bob explains. “You have to teach them how to care.”
Trust people with real responsibility. When Barry-Wehmiller needed a new machine (budget: $750,000), they gave the project to Jared, a factory floor leader. His first move? He went to the two operators who’d actually use the machine. “I don’t know what we should get,” he told them. “You guys are the experts.” They found the perfect machine, saved $250,000. It’s still running 12 years later. Trust is caring made visible.
Don’t betray them when times get hard. In 2008, Barry-Wehmiller’s orders dropped 30%. Every business textbook says: lay people off. Bob refused. “What if we all took a little pain so no one had to take a lot of pain?” They implemented shared sacrifice. No layoffs. “My primary responsibility is to have a business model where you feel safe,” Bob explains. You can teach empathy skills all day. But if you lay people off when it’s convenient, you’ve taught one lesson: the caring was bogus.

The Test You Can Use Tomorrow

Bob offers a simple test for any leadership decision:

“Treat them like you would want your son or daughter treated.”

People usually respond: “Oh, that would be different.”

Bob’s reply: “Why is it different that it’s somebody’s son or daughter you’re treating?”

Before your next difficult conversation, performance review, or restructuring decision—picture their parent. Someone who loves them deeply. Who entrusted their child to you.

What would you say? How would you decide?

When Simon told Bob this after knowing him for 15 years, Bob started to tear up: “I know people who turn it on and turn it off. You can’t turn it off. It’s core to who you are. You take taking care of your people as seriously as taking care of your children. You deeply mean it.”

Bob’s response: “You can retire from a job, but you cannot retire from a calling.”

At the end of the day, you can’t teach caring if leadership doesn’t actually care. The techniques matter. The courses matter. But none of it works without genuine belief that the people in your care are someone’s precious children.

What You Can Try Right Now

Change one word: Stop saying “headcount.” Start saying “team members.” Notice how it shifts your thinking.

Show up for one person: Pick someone who doesn’t trust you. Say good morning. Every day. Don’t ask for anything. Just show up.

Give away one decision: Find someone doing the actual work. Give them real responsibility and real budget. Then get out of their way.

Ask the hard question: Next time you face financial pressure, ask: “What if we all took a little pain instead of a few people taking all of it?”

The way you see people affects the way you treat people.

And the way you treat people? That’s what you’re really teaching.

Bob Chapman’s book “Everybody Matters” tells the full story.

Is It Wrong to Be Friends with Your Coworkers? A Therapist Weighs In

Posted on October 22, 2025October 22, 2025 by Team Simon

We’ve all felt that awkward tension when a colleague asks about your weekend plans and you’re not sure how much to share. Or when someone invites you for after-work drinks and you freeze, wondering if accepting crosses some invisible professional line. In some industries, there seems to be a cultural rule that if someone is your colleague, they shouldn’t really know about your personal life. Keep it professional. Keep it distant. Keep it safe.

But is that really the healthiest approach?

In a recent conversation between Simon and Dr. Sara Kuburic—a therapist who specializes in workplace dynamics and teacher of our course, How to Handle Conflict at Work—they explored this exact tension. And, according to Sara, the challenge isn’t whether to befriend coworkers. It’s how to do it with intention, awareness, and healthy boundaries.

Here’s what we learned.

The Truth: All Work Relationships Are Personal

Let’s start by dismantling a myth. “All relationships are personal relationships,” Sara says. Even the most buttoned-up, strictly professional dynamic involves human connection, emotional dynamics, and personal investment. The question isn’t whether work relationships are personal—they always are. The real question is: what kind of personal relationship do you want to cultivate?

Sara’s own philosophy is refreshingly honest: “In my ideal world, I would work with all my best friends.” When choosing projects, she asks herself fundamental questions like: “Do I want to spend time with you? Do I find the dynamic meaningful enough for us to spend 40 hours, 100 hours, 200 hours working together on this project?”

Think about that for a moment. If you’re going to spend more waking hours with colleagues than with your own family, shouldn’t you actually enjoy their company?

The difference between work friendships and other friendships isn’t that one is “personal” and the other isn’t. It’s that the boundaries, expectations, and needs are different. And that’s where things get complicated.

How to Test the Friendship Waters (Without Making It Weird)

One of the trickiest aspects of workplace relationships is figuring out where you stand. You might think you’re developing a genuine friendship, only to realize the other person views you strictly as a colleague. So how do you read the room before you accidentally overstep?

Sara recommends testing it out casually and paying attention to the signals. Here are some practical ways to gauge interest:

Extend low-pressure invitations. Ask if they want to grab coffee during lunch or join you for a drink after work. These are casual enough that declining doesn’t feel awkward, but accepting signals openness to a more personal connection.

Pay attention to their responses. If someone consistently says no to social invitations without offering alternatives, that’s information. If they always give one-word answers when you ask “How was your weekend?” they’re setting a boundary—not because they dislike you, but because they prefer to keep work and personal life separate.

Accept the answer without taking it personally. As Sara puts it, “It can feel a little brutal, but now you know.” Some people are looking for friends at work; others aren’t. Neither approach is wrong. The key is reading the signals and respecting what you discover.

This testing phase isn’t about playing games or being manipulative. It’s about reading social cues and respecting people’s boundaries before you invest emotionally in a relationship that might not be reciprocated.

The Trust Factor: Watch for Ulterior Motives

Here’s an uncomfortable truth about workplace friendships: they come with a layer of uncertainty that friendships outside work don’t have. “Are they being friends with you because they want a promotion?” Sara asks. “Are they being friends with you because they need something from you?”

This isn’t cynicism. It’s realism. Work involves hierarchies, politics, competition for resources, and advancement opportunities. Sometimes what feels like friendship is actually strategic networking. And that’s genuinely difficult to navigate.

So how do you distinguish between authentic connection and professional calculation?

Look for consistency over time. Real friendship remains steady regardless of whether you can offer something. If someone is only warm when they need a favor or distant after they’ve gotten what they want, that reveals their true motivation.

Notice if they’re interested in you as a person. Do they remember details about your life? Ask follow-up questions about things you’ve shared? Show curiosity about who you are outside your job title? Genuine friends care about the whole person, not just the professional persona.

Trust your gut. If something feels transactional, it probably is. Pay attention to that discomfort rather than dismissing it.

The reality is that many work relationships exist in a gray area. They’re somewhat genuine but also somewhat strategic. And that’s okay, as long as you’re aware of it and adjust your expectations accordingly.

The Non-Negotiable: Never Bond Over Negativity

If there’s one hard rule Sara emphasizes, it’s this: “No relationship should be founded on badmouthing other people.”

We’ve all seen it happen. Two people connect by complaining about their boss. Or gossiping about a difficult colleague. Or competing to share the most outrageous story about someone who isn’t in the room. And in the moment, that shared frustration can feel like bonding.

But it’s not. It’s a false foundation that will eventually crumble.

“People can really connect by hating on someone, by hating their boss, by being really upset,” Sara says. She understands it might even be a starting point. But if you don’t want your relationship based on gossip or simply disliking another person, you need to redirect the conversation.

Her suggested script is direct but kind: “Hey, I totally understand why you’re upset, but I don’t feel comfortable talking about another coworker that way.”

Will it be uncomfortable? Yes. But it’s also how you establish yourself as someone with integrity—someone who doesn’t participate in the toxic alliances that can make workplaces miserable.

Sara warns that this is how we “unintentionally form teams and alliances, and it becomes this really intense, complex thing that ‘you can’t be friends with Billy because you’re friends with Joel.'” Sound familiar? It’s high school dynamics in professional clothing. And it’s time to move past it.

The better approach: If you’re genuinely upset about a workplace issue, address it directly with the person involved or escalate it to HR if it’s serious. Don’t let your workplace friendships become echo chambers of negativity.

Making It Work When Everyone’s Remote

The rise of remote work has added another layer of complexity to workplace friendships. As Simon points out, quoting violinist Isaac Stern: “Music is what happens between the notes.” In a work environment, trust is what happens between the meetings—in the hallway, walking out of the conference room, bumping into each other and saying, “Oh, I meant to tell you something.”

These micro-moments build relationships and trust. And in a remote environment, they simply don’t exist unless you create them intentionally.

Sara’s advice is to treat remote work relationships like long-distance relationships—they require extra effort and intentionality:

Over-communicate tone in messages. Add emojis to clarify how you mean something. Make messages slightly longer to provide context. What seems clear to you can easily be misinterpreted by someone reading without the benefit of your facial expressions or tone of voice.

Schedule video calls when you feel distant. If you sense a relationship cooling or communication feeling strained, suggest a quick video chat. Seeing someone’s face rebuilds connection in ways that text never can.

Create the “between the meetings” moments. Send a quick message after a meeting: “That was a really interesting comment—it made me think of this.” Share a relevant meme. Drop a virtual thumbs up. These tiny gestures matter.

Check in with genuine curiosity. It’s easy to check in when you’re in the same space and notice someone looks tired or stressed. Make that same effort virtually. A simple “How are you doing?” can make someone feel seen.

As Sara puts it: “We all just want to feel seen and heard, and sometimes it’s as easy as acknowledging someone.” And yes, she genuinely recommends sending memes. “All the best coworkers send each other memes. It’s just a really fun bonding experience.”

The key is recognizing that remote relationships won’t develop organically. You have to be deliberate about creating connection.

Setting Boundaries Without Being an Asshole

So you’ve decided to befriend a coworker, but you still need boundaries. How do you maintain them without coming across as cold or difficult?

Sara’s answer comes down to two things: what you say and how you say it.

“Sometimes what tips the scale from being firm to being an asshole is the extra eye roll or the really harsh tone or the crossing of the arms,” she explains. Body language and tone matter as much as your actual words.

Before setting a boundary, check yourself:

What’s your facial expression?
What’s your tone—calm and matter-of-fact, or sharp and defensive?
What’s your body language communicating?

Make sure it’s an actual boundary, not just a preference. Boundaries are about protecting your wellbeing, time, or values. Preferences are just how you like things done. Know the difference. A boundary might be: “I don’t discuss my personal life at work.” A preference might be: “I’d rather you text than call.” The first deserves firm protection; the second deserves flexibility.

Be honest and direct without insulting. You can be clear without being cruel. “I need to focus on this project, so I can’t chat right now” is firm but respectful. “I’m busy” with an irritated tone is dismissive.

The goal is to be someone who has clear boundaries but remains approachable and kind. That balance is what distinguishes healthy assertiveness from being difficult to work with.

So is it wrong to be friends with your coworkers? Absolutely not. In fact, given how much time we spend at work, cultivating genuine connections with colleagues can significantly improve your quality of life and job satisfaction.

But (and this is important) workplace friendships require a different kind of awareness than other friendships. They need:

Intention in how you build and maintain them, especially in remote environments
Boundaries that protect both the relationship and your professional reputation
Awareness of power dynamics, ulterior motives, and the difference between genuine connection and strategic networking
Integrity to refuse bonding over gossip or negativity
Respect for people who prefer to keep things professional

The healthiest workplace friendships are built on mutual respect, authentic interest in each other as people, and clear communication about boundaries and expectations. They’re not automatic, and they’re not always easy. But they’re possible—and often, they’re deeply valuable.

As Sara reminds us, all relationships are personal relationships. The question isn’t whether to make work personal. It’s how to do it in a way that enhances both your professional life and your wellbeing.

For more insights from Sara, check out her course, How to Handle Conflict at Work.

About to Explode on a Coworker? Try This Psychotherapist’s Simple, 5-Step Plan

Posted on October 21, 2025October 21, 2025 by Team Simon

You know that feeling when someone takes credit for your work in a meeting and you can literally feel your blood pressure spike? Or when you get that passive-aggressive email and suddenly you’re mentally drafting a response that would make your HR rep weep?

Yeah. We’ve all been there. (We’re only human, after all.) But if you’re finding yourself running hot at work on occasion, here’s a crazy fact we learned from Dr. Sara Kuburic, a psychotherapist who teaches the online course, How to Handle Conflict at Work.

That overwhelming emotion you’re feeling? Physiologically, it only lasts about 90 seconds.

We know, we know. If you’ve ever spent an entire weekend replaying an argument with your boss, this sounds completely wrong. But stick with us, because understanding why we stay angry for hours (or days) changes everything about how we handle these moments.

According to Dr. Kuburic, “The narratives we tell and retell ourselves retrigger these feelings over and over again. Instead of witnessing the emotion—noticing how we feel and how it’s being expressed in our body, and appropriately responding—we latched on to the thought that evoked it in the first place.”

Translation? You’re not still furious because the emotion never ended. You’re still furious because you keep replaying it, rehashing it, and basically hitting the “restart” button on those 90 seconds over and over.

So what do you actually do when you’re at that breaking point? Here’s what Dr. Kuburic recommends:

Step 1: Catch Yourself in the Replay Loop

Look, that first wave of anger or frustration or hurt? That’s real. That’s your body doing its thing. You get about 90 seconds of pure physiological response—heart racing, face flushing, all of it. That part isn’t really up to you.

But here’s where it gets interesting. After those 90 seconds? The choice is yours.

Dr. Kuburic explains it like this: “It’s the meaning we attribute to the thought that perpetuates the feeling, and keeps us hostage.” So after that initial reaction, pause and ask yourself: Am I actually still feeling this, or am I now just thinking about it? Am I replaying what they said on a loop? Imagining the perfect comeback? Catastrophizing about what this means for my career?

Why this matters: “At what point does how we feel become a choice?” Dr. Kuburic asks. “If we keep feeding or dwelling in the narratives that hurt us, is it on us? Does it mean we choose to feel this way? Yes. It does. After their 90 seconds have come and gone, you have the power to consciously choose your narrative.”

And before you think this is about blaming yourself for feeling bad—it’s not. She’s super clear about this: “This perspective is not meant to blame us for feeling hard things, but rather to empower us.”

It’s about recognizing that you have more control than you think. Which, honestly, feels pretty good when everything else feels out of control.

Step 2: Get Specific About What You’re Actually Feeling

Here’s something that sounds weird but actually works: when you’re drowning in one big emotion, don’t try to make it smaller. Make it bigger.

Dr. Kuburic suggests this: “When you feel an especially strong emotion, try to identify one or two other emotions that are also present. The more the better. Although it may seem counterintuitive to try and feel more when you are already overwhelmed, identifying multiple emotions can actually dilute the power of the consuming emotion.”

So yeah, you’re angry. But what else? Are you also embarrassed that this happened in front of everyone? Disappointed because you thought this person was better than that? Anxious about how to fix it? Maybe even a little relieved that the issue is finally out in the open?

Why this helps: Dr. Kuburic points out that “most of us usually won’t allow ourselves to feel something that’s seemingly contradictory. We struggle to hold both. A common combination, for example, is sadness and relief, yet we often ignore the relief because we don’t know how to make sense of these two feelings together. So we overcommit to sadness. Until we learn to carry it all, we will only see one side of ourselves.”

When you name all the feelings—even the contradictory ones—that one overwhelming emotion loses some of its grip on you. It’s like, oh, this isn’t just pure rage. It’s actually this complicated mix of things I’m dealing with. And somehow that makes it more manageable.

Step 3: Give Yourself Permission to Pause Before You Respond

This is the big one. The difference between sending that scorched-earth email and actually solving the problem.

Dr. Kuburic makes this distinction: “Responses are thoughtful and rooted in authenticity, reason, and values. They are aligned with who we are and who we want to become. They take context into consideration. Reactions are rooted in wounds, fears, insecurities. They are often our misguided attempt to protect ourselves.”

Basically? Reactions are what happen when we don’t give ourselves that pause. Responses are what happen when we do.

Real example from her course: “If a coworker accidentally insults you, reacting would be insulting them back. Responding, on the other hand, would look like taking a deep breath and setting a clear boundary.”

Why this works: That pause—that space between what happened and what you do next—that’s where all your power is. As Dr. Kuburic notes, “One problem that we encounter is that we often don’t notice our emotions until they overwhelm us. We have clever ways of sidestepping or ignoring our feelings so that we don’t have to deal with them… until we do. And the moment we are ‘forced’ to deal with emotions, we often react.”

So give yourself permission to take a beat. Walk around the block. Sleep on it. Whatever you need to create that space.

Step 4: Figure Out What Your Emotions Are Trying to Tell You

Here’s where Dr. Kuburic’s approach really clicked for us. She doesn’t want you to just stuff your emotions down or “manage” them. She wants you to actually listen to them.

“Emotions are not liabilities—they are tools,” she says. “Our emotions exist to tell us things that our rational brains miss. But in order to learn from our emotions, we must first be able to recognize, identify, and understand them.”

She suggests asking yourself these questions:

What is this emotion trying to tell me?

For example, “Anger often tells us 3 things: Our boundary is being crossed, our need is not being met, or our role or positions feel threatened.” So if you’re angry, which one is it? That actually gives you somewhere to start.

What can I learn from this?

“Every emotion we experience towards others is a mirror, reflecting not only our perception of them but also revealing deeper layers about our own beliefs and past experiences. Jealousy, for instance, speaks to our own insecurities or unfulfilled needs.” Ouch, but also… useful to know, right?

Which of my values is this touching?

Here’s an example from the course: “Let’s say you’ve been asked to work with a high-performing team that often cuts corners. You feel uneasy but you can’t immediately identify why. By asking yourself, ‘Which of my values is this emotion speaking to?’, you realize that one of your core values is integrity.” Suddenly that vague unease makes sense.

What story am I telling myself about this?

Why this matters: “Identifying the right emotion is so important because every emotion comes with a different message,” Dr. Kuburic explains. “We need to know what this message is in order to show up authentically and be able to communicate what we are experiencing with others.”

Your emotions are trying to help you. They’re just not always great at being clear about it.

Step 5: Decide Who You Want to Be in This Moment

This is the part that keeps us from doing things we’d regret. Dr. Kuburic frames it like this: “Every action and inaction shapes who we become. Deciding what we do with our emotions is a lot more significant than managing the situation, it’s about shaping your future Self.”

So when you’re feeling completely overwhelmed, ask yourself:

How do I want to handle this?
What am I actually trying to achieve here?
Do I need more time to think about it?
Do I need to sit with this feeling a bit longer?
Am I ready to talk about it?

And then, whatever you decide, own it. “Some expressive acts lead to deeper understanding and some can be harmful—this distinction is really important. Whatever we decide to express, we must take responsibility for our actions.”

Why this works: As Dr. Kuburic puts it: “Who do you want to be? You are defined by the choices you make. Now act like it.”

It’s not about being perfect. It’s about being intentional.

Want to go deeper? Check out Dr. Kuburic’s course, “How to Handle Conflict at Work,” by clicking here.

Why Being a “Nice” Manager Totally Backfires, According to Simon

Posted on October 14, 2025October 14, 2025 by Team Simon

You care about your team. You want to be a good leader: approachable, supportive, human. So you’re nice. You say yes to requests. You avoid hard conversations. You give people grace when they miss deadlines. You create a comfortable environment.

And your team is failing.

Deadlines are missed. Quality drops. Standards erode. Nobody seems to care anymore. And you’re left wondering: How did trying to be a good leader create such a mess?

Here’s the truth: Nice and kind are not the same thing. One keeps people comfortable. The other helps them grow. One avoids discomfort. The other leans into it. And confusing the two can derail your effectiveness as a leader and potentially your entire team’s performance.

This critical distinction came to light during our most recent Q&A session where Simon spent 90 minutes with members of The Optimism Library on the topic of “Leveling Up from Middle Manager to Leader.” With middle managers representing “the backbone of every organization” yet rarely given “the tools, training, or support to be great,” we tackled the real struggles of leaders caught between caring for people and delivering results.

Simon didn’t just teach this distinction. He confessed to living this failure himself and shared how learning the difference between nice and kind saved his company.

The Confession

Simon didn’t dodge or deflect. He owned it completely:

“This is my journey. Because of the books I write and the talks I give and what I put myself out there, I feel even greater pressure to be authentic, to be the leader that I write about, because I know a lot of folks like me who talk about one thing and they’re not like that, and I don’t want to be that person.”

But that pressure created a trap: “I was working so hard to be nice and likable and concerned and worried and caring. That literally I ran a company that couldn’t meet a deadline, couldn’t hit a goal, couldn’t get a product out the door on time. The quality was crap, you know?”

The result? “It became to the point where I realized that… I was being taken advantage of, people’s standards went down, people stopped caring about deadlines, and it got to the point where we had a real culture problem.”

This is exactly the kind of mistake that happens when you’re promoted to middle management without being taught how to balance care and accountability, two skills that seem contradictory but must coexist.

The Distinction That Changes Everything

This is where Simon made the breakthrough that transformed his leadership, a distinction nobody had taught him:

“I had to be very open where I’ve over indexed on nice and I started to make realizations that there’s a difference between nice and kind, right? And I was doing nice, I wasn’t doing kind.”

He clarified with concrete examples: “Giving someone hard feedback, it’s not nice, but it is kind. Being, you know, mushy mushy all the time, you know, it doesn’t get anything done. So… sometimes hearing hard feedback, it’s kind, but it’s not nice.”

“I made the distinction that I wanted to be human. I want to be approachable, but I would also say, like, guys, we have to do this, because the business is what fuels the mission.”

This is one of those leadership skills that’s essential for middle managers but rarely taught: how to be both supportive and demanding, both human and accountable.

The Business Reality

Simon used a powerful analogy to drive this home:

“I think about a business like a car, right? Which is you don’t buy a car simply to buy gasoline. That’s not the purpose of a car. You buy a car to go somewhere and you need fuel to go to those places. Well, that’s a company. We didn’t start a company simply to make money but we do need money to make the company go somewhere.”

This realization led to structural changes: “We just became much clearer about what deadlines were and what expectations were. And we do have goals.”

What Kind Actually Looks Like

Being kind, Simon explained, means giving people what they need to succeed, even when it’s uncomfortable. This is another one of those crucial middle management skills: setting clear expectations.

“Not giving people goals is actually demoralizing. People want goals. You wanna know what the finish line is. It’s actually very difficult to work without specific goals. Growth doesn’t help. Better is not a help. I need to go from here to here. I need be able to measure that we are doing well so that somebody can feel like their work matters.”

He continued: “If it’s just mushy, mushy and amorphous and better and more, nobody actually knows that they’re doing a good job. Again, not kind.”

As Simon emphasized throughout the session about the skills middle managers need: “I think the big thing is clarity. Because I think very often as a leader, it’s like, ‘Guys, let’s increase our performance,’ but nobody knows what the deadlines are. Nobody knows what the targets are. So clarity of deadline, clarity of target. And then how can I support you to help you hit that target or that deadline? That’s a huge, big thing. Be very, very clear.”

Implementing Kind Leadership

Simon’s framework became clear:

Set clear expectations: “I realized that I needed clear deadlines. I needed clean expectations. I needed clear metrics.”
Maintain humanity in how you reach them: “How we get there matters. Because ethics still matter, right? It’s not growth at any opportunity.”
Focus on support, not softness: “How do we support each other to hit those goals? And that’s where the humanity and the niceness shows up. You still have to treat people with kindness and respect.”

Giving Kind Feedback

When it comes to delivering hard truths (another skill middle managers need but aren’t taught), Simon shared his approach:

“When we do feedback sessions, when we did three 60s, for example, they can be pretty brutal. And we say this out loud, which is someone is going to give you feedback. It’s much easier for them not to tell you because it’s going to be hard to tell you some of these things. But the reason they’re going to tell you is because they care about you and they want you to grow to be the best version of yourself.”

His technique: “I always ask permission. I need to give you some hard to hear feedback. Can I give that to you?”

Nice avoids difficult conversations. Kind leans into them.

Nice prioritizes being liked. Kind prioritizes being effective.

Want to master the leadership skills nobody taught you when they made you a manager? Learn how to balance accountability with humanity in our course: How to Be the Leader People Actually Trust (and Maybe Even Love).