Simon Sinek - Page 7 - The Optimism Company

The Three Simple Words That Could Elevate Your Career

Posted on March 18, 2025March 18, 2025 by Team Simon

There’s a scene that plays out in conference rooms across the world every day. A middle manager sits at the table while their boss asks a challenging question. The entire room turns to look. In that moment, despite not having a clear answer, the manager nods confidently and begins crafting a response that sounds plausible but isn’t entirely honest.

Sound familiar? It happens more often than anyone likes to admit.

During a recent leadership session, Simon shared what he calls “the single best thing” he ever learned in his career:

“I don’t have to know all the answers and I don’t have to pretend that I do. The single best thing I ever learned was the confidence to say, ‘I don’t know.'”

This insight can redefine your career, especially for middle managers. Caught between executives who expect expertise and team members who look to them for guidance, middle managers often become masters of appearing knowledgeable, sometimes at the expense of authenticity and growth.

The Weight of “Knowing Everything”

Consider the feeling of that knot in your stomach when asked something you’re not sure about. Perhaps during a strategy meeting or when a direct report asks for your take on a complex situation.

Simon describes how early in his career, he believed leadership meant having all the answers. His perspective changed dramatically thanks to a mentor named Peter, who “never answered a damn question ever.”

Instead, whenever Simon would approach him with a problem, Peter would respond with four simple words: “What do you think?”

Initially frustrating, this approach ultimately taught Simon self-reliance and critical thinking. It wasn’t about Peter avoiding responsibility—it was about him developing Simon’s capabilities.

The Middle Manager’s Paradox

Middle managers exist in a unique space. They’re close enough to the front lines to understand operational realities but expected to translate executive vision into actionable plans. This position can create a debilitating pressure to appear all-knowing.

We’ve seen this countless times in our work with organizations. A newly promoted department manager suddenly faces questions from junior team members about projects they barely understand, while the executive team expects unwavering confidence in progress reports.

The common solution? Pretending to know more than they do. Offering vague responses, redirecting conversations, or—worst of all—providing definitive but incorrect answers rather than admitting uncertainty.

The results are predictable: mistakes compound, trust erodes, and stress levels skyrocket.

The Liberation of “I Don’t Know”

What Simon emphasizes is that saying “I don’t know” isn’t a leadership failure—it’s a leadership opportunity.

He explains how psychological safety starts with leaders modeling vulnerability: “Psychological safety is very simple; it means that I feel safe to say I made a mistake or I don’t know, without any fear of humiliation or retribution.”

Here’s what happens when middle managers embrace “I don’t know:”

They build genuine trust. Teams appreciate honesty more than false certainty.
They create learning opportunities. When leaders don’t know, they can discover alongside their team.
They model the behavior they want to see. If managers can admit when they don’t have answers, team members will feel safe doing the same.
They reduce their stress level. The energy spent maintaining a facade of omniscience is exhausting.

From Theory to Practice

Simon often shares stories from leaders who’ve transformed their approach after embracing this principle.

One middle manager at a technology company was asked during a quarterly planning meeting about the expected ROI on a new initiative their team was leading. The instinct kicked in—make an educated guess, sound confident, move on quickly.

Instead, they took a breath and said: “That’s an important question, and honestly, I don’t have a reliable number for you right now. We’re still gathering data on several variables. I can pull together an analysis by Friday, but I’d rather give you accurate information than a hasty estimate.”

The room didn’t collapse. The CEO didn’t fire them on the spot. Instead, the CEO nodded and said, “I appreciate that. Let’s reconnect on Friday.”

That small moment changed something fundamental in how the manager approached their role. By Friday, the team had developed a thorough analysis that was far better than whatever might have been improvised in the meeting.

Making “I Don’t Know” Productive

Of course, there’s a difference between a thoughtful “I don’t know” and a dismissive one. Simon emphasizes that great leaders don’t just stop at uncertainty—they use it as a starting point.

Here’s how to make “I don’t know” productive:

Acknowledge the gap: “I don’t have that information right now.”
Commit to finding out: “Let me research that and get back to you by [specific time].”
Invite collaboration: “What’s your perspective on this? I’d like to hear your thoughts as I work on this.”
Follow through: When you promise to find an answer, deliver on that promise.

This approach transforms “I don’t know” from a perceived weakness into a demonstration of integrity and commitment to excellence.

The Ripple Effect

One of the most powerful insights Simon shares is how this approach affects the entire team: “If the boss lies, yells, screams, always has all the right answers, guess what you’re going to get from the team? You’re going to get pushiness, people jockeying to be right all the time.”

The opposite is also true. When leaders model the courage to acknowledge uncertainty, their teams follow suit. Decision-making improves because people bring real data rather than what they think leaders want to hear. Innovation flourishes because team members feel safe proposing ideas that might not work. Problems get addressed earlier because no one feels they have to hide challenges.

Middle managers are uniquely positioned to create this culture within their teams, even if it doesn’t exist throughout the organization.

Your Next Opportunity

The next time you’re facing a question you don’t have a clear answer for, remember that you have a choice. You can fall back on the comfortable habit of pretending to know, or you can embrace the opportunity to demonstrate authentic leadership.

Try responding with: “That’s a great question. I don’t have a complete answer right now, but I think it’s important enough to give it proper consideration. Here’s what I do know, and here’s how I propose we find out more…”

Then notice what happens—not just in the conversation, but in how you feel about yourself as a leader.

As Simon says, courage in leadership often comes from having “at least one person in your life professionally or personally to say, ‘I believe in you, you got this, and if everything goes south, I’ll be there with you.'”

Why the Best Leaders Know When to Keep Their Mouths Shut

Posted on February 26, 2025February 26, 2025 by Team Simon

Imagine you’re in a high-stakes meeting. The team is discussing a critical problem, and as the leader, everyone expects you to have the answer. What do you do?

If you’re like most leaders, you might feel pressured to speak up immediately. To demonstrate your value. To prove why you’re in charge.

But according to former Navy SEAL commander Jocko Willink, that instinct could be undermining your team’s potential and your own effectiveness.

“When I go in a room with my 10 subordinate leaders, I know that they’re going to have better ideas than me or at least they’ll have a point of view that I don’t have,” Jocko shared with Simon on this week’s episode of A Bit of Optimism.

This seemingly simple insight reveals a profound truth about leadership: sometimes the most powerful thing you can do is create space for others to step up.

The Power of the Leadership Vacuum

Jocko calls it “the leadership vacuum”—that uncomfortable silence when a decision needs to be made, but no one is immediately taking charge. Most leaders rush to fill this vacuum, but Jocko suggests a different approach:

“When that leadership vacuum occurs, I’m going to give it at least enough time that everybody feels it. I want everyone in the room to feel it.”

Why? Because jumping in too quickly sends a powerful, often unintended message: your ideas aren’t wanted here.

“If I jump in too early, there’s a couple people maybe who were about to—Simon had an idea he was about to say something—and I just cut him off. Now he’s going to be begrudgingly executing what I told him to do.”

That begrudging execution is the enemy of true commitment and high performance. When team members feel their perspectives aren’t valued, they might follow orders, but they’ll do so without the enthusiasm, creativity, and ownership that drives exceptional results.

Creating Space for Better Ideas

The practical application is simple but powerful:

Pause deliberately when decisions need to be made
Let the silence linger long enough for people to feel the need
Create space for different voices to emerge
Step in only when necessary

“If a decision needed to get made, I would make a decision, but I would make a little tiny decision,” Jocko explains. “If someone else makes the next decision, I’m fine with it.”

This approach accomplishes several things simultaneously:

It demonstrates humility by acknowledging others might have better ideas
It empowers team members to contribute meaningful solutions
It builds collective ownership of decisions and outcomes
It prevents the team from becoming dependent on a single leader

Balancing Decisiveness with Openness

This doesn’t mean abdicating your responsibility as a leader. Jocko, known for his decisiveness in the SEAL Teams, isn’t suggesting indecision or endless deliberation.

“I was known in the SEAL Teams for being very decisive,” he says. The key is finding the balance between making necessary decisions and creating space for others to contribute.

In high-stakes environments, this balance becomes even more critical. “In chaos of combat, when the leader starts barking orders, the good followers know when to contribute and when to follow,” Jocko shares.

The goal isn’t to abandon decisiveness but to use it judiciously—to be decisive about when you need to be decisive.

Building Trust Through Balance

This balanced approach helps build the trust that’s essential for high-performing teams. As Jocko emphasizes, “The components of a relationship are trust, listen, respect, influence, and care.”

By creating space for others’ ideas while maintaining the ability to make decisions when necessary, you demonstrate both respect for your team’s capabilities and your own commitment to the mission. You show that you care more about finding the best solution than being seen as the one with all the answers.

The result? A team that feels valued, engaged, and committed—not just to following orders but to achieving shared goals.

Putting It Into Practice

Ready to try this approach with your team? Start small:

In your next meeting, deliberately pause after presenting a problem
Count to 10 in your head before offering your own solution
Acknowledge and build on the ideas that emerge
If no ideas emerge, make the smallest decision possible to move forward

Remember, as Jocko points out, “The team that gets along, the team that has good relationships wins all day long.” And few things build better relationships than genuinely valuing each other’s contributions.

Because ultimately, leadership isn’t about having all the answers—it’s about creating the conditions where the best answers can emerge, regardless of who they come from.

The Hidden Cost of “Maybe:” How Unclear Requests Sabotage Your Team

Posted on February 25, 2025February 25, 2025 by Team Simon

Picture this: You’re wrapping up a team meeting when you say, “It would be great if someone could pull together those numbers for next week.” Everyone nods. You assume Joe will handle it—he usually does. But when next week arrives, no numbers. No Joe. Just a gap where you expected results.

What went wrong?

According to communication expert and Optimist Instructor Lori Zukin, this common scenario reveals a fundamental breakdown that happens in workplaces every day: the gap between what we think we’re asking for and what others actually hear.

“When we have unclear or incomplete requests, offers, and commitments, they can frequently cause breaches of trust,” Zukin explains in a class on clear communication in The Optimism Library. Even more challenging? “People who have perfect intentions” can still fail to deliver simply because the request wasn’t clear from the start.

The High Cost of Ambiguity

These misunderstandings aren’t just minor annoyances—they can erode trust, delay projects, and create unnecessary tension between well-meaning colleagues. When someone doesn’t deliver on what you thought you asked for, it’s easy to question their competence or commitment. Meanwhile, they may be completely unaware they’ve disappointed you.

This pattern repeats itself in meetings, emails, and conversations countless times each day, creating what Zukin calls “breaches of trust” that could be easily avoided.

The SMART Request Framework

So how do we fix this communication gap? Zukin recommends transforming vague wishes into SMART requests:

Specific: Exactly what needs to be done
Measurable: How we’ll know it’s complete
Attainable: Within the person’s capabilities
Relevant: Connected to important outcomes
Time-bound: Clear deadline

Instead of “It would be great if someone could pull together those numbers,” try:

“Joe, could you compile the Q3 sales figures into the standard report template by Thursday at noon? We need this for Friday’s executive presentation, and your expertise with these numbers would be really valuable. Is that something you can commit to?”

This approach answers the critical questions: the who, what, when, why—and most importantly—gets a clear commitment.

When “Yes” Doesn’t Mean “Yes”

Even when you make a clear request, Zukin warns about another common pitfall: hedging responses.

“Obviously, they leave ambiguity about whether the task is gonna get done or not get done,” Zukin notes. “I don’t know if I can trust them to get it done, and I don’t know if they’re really gonna follow through.”

Listen for phrases like:

“I’ll try”
“I’ll see what I can do”
“Let me see how things go”
“I should be able to”

When you hear these responses, Zukin suggests a simple approach: reflect back the hedge.

“Hey, I’m hearing you say that you’re gonna see how things are going. That sounds like a maybe.”

This gentle observation gives the person a chance to either commit firmly or decline honestly—both better options than a half-hearted maybe.

From Complaints to Requests

Perhaps most powerful is Zukin’s framework for transforming complaints into effective requests.

“One of my coaches noticed that I was complaining about something,” Zukin shares, “and she said, those gifts actually usually mean that you have a request that you are not making clear, or that you’re not making at all.”

The next time you catch yourself complaining, try this four-step process:

Identify what’s frustrating you
Clarify what you actually want
Determine who can help you get it
Make a SMART request to that person

For example, instead of complaining “This client keeps changing what they’re asking for,” you might request: “Can we schedule a 30-minute call with the client by Friday to confirm the final scope of the project?”

Making It Work for You

Start by auditing your own communication. Are your requests clear and specific? Do you check for real commitment? Do you convert complaints into constructive requests?

The payoff for this small shift in communication can be enormous: fewer misunderstandings, stronger trust, and teams that actually deliver on their promises.

Because in a world of constant communication, clarity isn’t just nice to have—it’s essential for teams that want to move fast without breaking things (or relationships) along the way.

For more insights on building stronger communication skills, check out Lori Zukin’s full class in The Optimism Library, where she shares practical frameworks for transforming how your team communicates.

The Surprising Skills Your Team Needs Most (They’re Not What You Think)

Posted on February 25, 2025February 25, 2025 by Team Simon

Picture your last team meeting. Was everyone truly listening to each other? Could difficult feedback be shared openly? Did people feel safe enough to be vulnerable?

If you hesitated on any of these questions, you’re not alone. In his recent conversation about high-performing teams, Simon highlighted a surprising truth: technical skills might get you hired, but human skills determine whether teams truly thrive.

“If you create an organization that doesn’t have psychological safety, where it is performance at all costs, no one will reveal any of those things because they fear it makes them firable or damages their promotability,” Simon explains.

The Hidden Skills Gap

Most organizations are laser-focused on technical capabilities—coding, analysis, design, marketing expertise—but often overlook the human skills that actually determine whether those technical skills can be effectively deployed:

Giving and receiving feedback
Having difficult conversations
Setting healthy boundaries
Creating psychological safety
Balancing individual needs with team needs

“Effective leadership involves teaching and developing human skills,” Simon says, “such as listening, giving and receiving feedback, and having difficult conversations.”

The Art of the Difficult Conversation

One of the most valuable skills Simon discusses is how to approach challenging conversations. His approach is refreshingly practical:

“Can I have a difficult conversation with you now? I might say the wrong thing, but bear with me because this conversation is more important than me doing it perfectly.”

This simple framework does three powerful things:

It asks permission
It acknowledges potential imperfection
It emphasizes the importance of the conversation over perfect delivery

The result? A much higher chance of the message being received as intended.

Balancing Agency and Boundaries

Another critical skill Simon highlights is the dance between personal agency and healthy boundaries. He shares a story about a young employee who was burning out because they never said no to colleagues who needed support.

“This person would always say yes to the phone call and would always be there to listen, to the point of burnout,” Simon recalls. The problem wasn’t just individual—it was systemic.

“We can create conditions that make it very hard for somebody to flex their agency, but we can also create conditions where they are allowed to step into it,” he explains.

For leaders, this means:

Teaching team members how to set healthy boundaries
Creating a culture where “no” is respected
Modeling balanced behaviors yourself
Recognizing when someone is overextending themselves

The Paradox at the Heart of Teamwork

Perhaps most importantly, Simon reminds us of the fundamental tension that every team must navigate:

“Every single moment of every single day we are both individuals and a member of a group. We must weigh decisions between putting ourselves first or the group first.”

Great leaders understand this paradox and create environments where both individual growth and team success are possible.

“The team is more important than any individual on the team,” Simon says, “but I have to protect every individual on the team to make the team flourish.”

Making It Work in Your Team

Ready to strengthen the human skills in your organization? Start with these steps:

Explicitly name these skills as valuable in your team
Create opportunities to practice them in low-stakes situations
Establish clear norms for how feedback is given and received
Celebrate when difficult conversations lead to better outcomes
Address violations of psychological safety immediately

Remember: Highly functioning teams aren’t just about achieving goals. As Simon explains, they’re about “the joy of the playing, the relationships built along the way, and the knowledge that their work is of greater value than simply the money they make.”

Because in the infinite game of business and life, the relationships we build and the growth we experience along the way aren’t just nice-to-haves—they’re the whole point.

For more insights on building stronger teams through human skills, explore our collection of leadership lessons in The Optimism Library.

Why Your Best Ideas Might Need a Waiting List

Posted on February 24, 2025March 19, 2025 by Team Simon

Imagine you’re launching a new initiative at work. Your instinct might be to make it as accessible as possible—open to everyone, easy to join, readily available. But what if that’s exactly why it might fail?

During a recent talk about innovation, Simon shared a fascinating story about launching a millennial training program at a large company. Instead of making it widely available, they did something unexpected: the company made people apply for it.

“They said, ‘We only have a hundred spaces, and they have to apply to be a part of it,'” Simon recalls. The result? Not just full enrollment, but something far more valuable: organic demand that spread like wildfire across the organization.

The Power of Purposeful Barriers

Here’s what happened next: “About two weeks later, my sponsor at the company calls me up furious,” says Simon. “He says, ‘I’m getting calls from across the country from all these managers screaming and yelling at me, demanding why their people aren’t invited into this thing.'”

No marketing. No PR. Just genuine demand created by making something slightly out of reach.

Why This Works

The psychology behind this approach ties into what Simon calls the Law of Diffusion of Innovations. Here’s the breakdown:

2.5% of any population are innovators
12.5% are early adopters
The rest need more convincing

“The way you talk to early adopters is by starting with WHY,” Simon explains. “Talk about what you believe, not what you do.”

Putting It Into Practice

Want to launch your next initiative with built-in momentum? Here’s how:

Start Small and Selective: Instead of trying to please everyone, create a pilot program with limited spots. Make it feel special—because it is.
Make People Work for It: Create an application process. Ask for essays. Request recommendations. As Simon found, “We made the application process wasn’t easy. We read the actual essays and chose 100 people.”
Focus on True Believers: Here’s the magic: when Simon asked these selected participants to volunteer extra time to help build the program—with no extra pay or promotion prospects—50 people raised their hands. Why? Because they believed in the vision.

The Counter-Intuitive Truth

“I built my entire brand with zero marketing budget and no public relations,” Simon reveals. “It’s because I made a decision that I was going to focus only on early adopters.”

This approach works because it:

Creates natural scarcity
Builds organic excitement
Attracts committed participants
Generates word-of-mouth buzz
Establishes genuine value

Making It Work for You

Next time you’re launching something new:

Resist the urge to make it immediately available to everyone
Create thoughtful barriers to entry
Focus on finding your true believers first
Let their enthusiasm create natural demand

Remember: Sometimes the best way to make something spread is to make it slightly harder to reach. As Simon’s experience shows, the right people will not only find their way in—they’ll bring others with them.

For more insights on launching new initiatives and building organic momentum, check out Simon’s full collection of leadership lessons in The Optimism Library.

The Secret to Staying Optimistic (That Nobody Talks About)

Posted on February 24, 2025February 24, 2025 by Team Simon

Ever caught yourself saying “everything happens for a reason” when things get tough? Or pushed away negative feelings because “optimistic people stay positive?”

Here’s what Simon suggests instead: let yourself feel bad sometimes.

“I just said, can you stop with all of this, please, and just tell me how you feel?” Simon recalls telling a friend who was forcing positivity during a difficult time. It turns out, true optimism isn’t about forcing a smile—it’s about something much more powerful.

“Optimism is not naive, nor is it blind,” he says. “It is the undying belief that the future is bright.” But here’s the crucial part: that belief can coexist with current struggles, doubts, and difficulties.

The Problem with “Toxic Positivity”

When we try to force ourselves or others to “stay positive,” we’re actually creating more stress. Why? Because we’re not just dealing with the original challenge—we’re also battling the guilt of not feeling positive enough about it.

“A healthy person has all the emotions,” Simon reminds us. “If you get stuck in sadness, that’s a clinical problem. If you get stuck in happiness, that’s not healthy either.”

How to Practice Real Optimism

Make Space for All Emotions: Instead of pushing away negative feelings, acknowledge them. This doesn’t mean wallowing—it means accepting that every emotion has its place in a healthy life.
Double Down on Relationships: “You double down on relationships, double down on friendships,” says Simon. Real optimism isn’t something we achieve alone—it’s something we build together.
Separate Current Reality from Future Possibility: “What I’m talking about is not the absence of stress,” says Simon. “It’s just clarity as you go through that stress.” You can acknowledge today’s challenges while maintaining faith in tomorrow’s possibilities.

Putting It Into Practice

Next time you’re facing a challenge (or supporting someone who is):

Start with Honesty: Allow yourself or others to express genuine feelings without rushing to “fix” them.

Build Connection: Rather than offering solutions, focus on strengthening relationships. Sometimes just being present is more powerful than being positive.

Maintain Perspective: Remember that acknowledging current difficulties doesn’t mean giving up hope for the future. As Simon says, “We can sit in the hell and darkness and struggle now,” while still believing in a brighter tomorrow.

The Power of Real Optimism

This approach might feel counterintuitive at first. After all, we’re often taught that being optimistic means always looking on the bright side. But true optimism is more resilient than that—it’s the ability to face reality while maintaining hope, to acknowledge struggle while believing in possibility.

“Relationships will always outlast everything else,” Simon reminds us. “There’s nothing certain about anything at work, but the strength of those relationships will carry you through.”

By making space for all emotions and focusing on genuine connections, we build an optimism that’s authentic, sustainable, and contagious. It’s not about forcing smiles or finding silver linings—it’s about creating a foundation strong enough to support both our struggles and our hopes.

Because real optimism isn’t about pretending everything is fine. It’s about knowing that even when things aren’t fine, we have the strength, the support, and the capacity to move through it together.

For more insights on building stronger relationships, explore The Optimism Library today.

How to Hook Your Audience in 30 Seconds, According to Simon

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

Picture yourself at your last presentation. You probably started with some context: “Over the past two years, we’ve been analyzing…” or “I’d like to talk to you today about…” Now imagine instead walking in and saying: “The year is 1963. January. Vietnam.”

Feel the difference?

“Most people start with stuff that doesn’t matter,” says Simon. “They tell you the lesson they want you to learn, then tell you the story as an example. But it works much more effectively when you start with the story itself—when you start with the emotion.”

It turns out, we might be overthinking our openings. Here’s how to grab your audience from the first sentence (and why it’s simpler than you think):

Start Where the Action Is

Remember writing essays in school? We were taught to start with background, context, the “setting up” paragraph. Simon suggests something different: Write that first paragraph—then delete it.

“Just start where the action happens,” he advises. “Don’t worry about the lead-up. Don’t worry about saying ‘I’ve been thinking about this for quite a while now…’ Just begin.”

Trust Your Audience’s Patience

Here’s something reassuring: You don’t need to explain why you’re telling a story right away. “People are patient,” Simon explains. “They’ll listen without knowing why they’re listening—if it’s a well-told story.”

In fact, that curiosity can be powerful. When people think “Where is this going?”—that’s not a bad thing. It means they’re engaged.

Three Ways to Start Strong:

Set the Scene Simply: “The year is 1963…” Sometimes that’s all you need. Let people’s imaginations do the work of filling in the fashions, the environment, the mood.

Jump Into Action: Skip the build-up. Start where something happens. As Simon puts it, “When we start a story where the action happens, I’m saying ‘This story is for you, and I want you to be a part of this with me.'”

Save the Lesson: Here’s the game-changer: Don’t start by telling people what they should learn. Start with the story that makes them want to learn it. “When you’re giving the explanation after,” Simon shares, “you’re not talking at them—you’re bringing them along with you.”

A Simple Test for Your Opening

Next time you’re preparing a presentation, try this: Write your introduction as you normally would. Now look at your second paragraph. Could that be your opening instead?

As Simon puts it: “There’s no right way to start a story—but there are more engaging ways.” The goal isn’t perfection; it’s connection. Start where it gets interesting, and trust that your audience will come along for the ride.

Let’s See This in Action

Here’s how a lot of people might start a presentation about a new team collaboration tool:

“Good morning everyone. Today I’d like to talk to you about improving our team’s efficiency. Over the past six months, we’ve been analyzing our workflow patterns and researching various solutions. Our studies show that teams spend approximately 23% of their time searching for information across multiple platforms, and…”

Cue the audience checking their phones.

Now, here’s how you could start the same presentation:

“Last Wednesday at 3am, Sarah from Marketing was in tears. The biggest campaign of her career was launching in six hours, and she couldn’t find the updated brand guidelines anywhere. Not in Slack. Not in Drive. Not in any of the 47 email threads she’d searched.

“Finally, she found them—buried in an email from last June, hidden in a folder called ‘Misc 2023.’ She’d been looking for three hours. The campaign was due at 9am. Later, she discovered three team members had the file all along, each working from different versions.

“Sarah’s story isn’t unique—it happened again yesterday to the sales team during their biggest pitch of the quarter, and it’ll happen tomorrow to someone else on your team unless we do something about it. Let me show you what that something could look like.”

Feel the difference? The second version:

Raises emotional stakes (tears, biggest campaign)
Adds specific details (47 email threads, biggest pitch of the quarter)
Creates more urgency (six hours, biggest campaign)
Makes the problem more personal (someone else on your team)
Maintains credibility (doesn’t go over-the-top)
Sets up solution more compellingly

The data, research, and context can come later. First, give your audience a reason to care.

Because in the end, a great opening isn’t about being perfect—it’s about making people look up from their phones and think, “Wait, this matters to me.”

Ready to tell better stories? Dive into “Storytelling Secrets from Simon”—out now in The Optimism Library.

Want Better Teams? Put Your Phone Down First

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

Think about the last time someone came to talk to you. Where was your phone? Be honest—was it face up on your desk, quietly demanding attention with each notification?

“When somebody walks into your office, put your phone away,” says Simon. “It’s so easy, but it sends a powerful message that they matter.”

It sounds almost too simple to be meaningful. But according to Simon, these small moments of complete attention are the building blocks of extraordinary team culture.

“It’s the little things that add up more than the big things,” he explains. “Like saying good morning in the hallway. It doesn’t seem to do anything, but when you do it every day, people start to feel seen and heard.”

The Power of Consistency

This isn’t about grand gestures or company-wide initiatives. It’s about the tiny choices we make dozens of times each day. Simon shares a story about his friend Bob Chapman, who learned from his priest that “consistency is more powerful than intensity.”

Think about that for a moment. We often believe leadership is about big moments—the inspiring speeches, the crucial decisions, the bold directions. But what if the real magic happens in those small, everyday interactions?

Making It Work (Really Work)

Here’s how to put this into practice:

Create a Phone-Free Zone

When someone enters your office or starts a conversation, make it a ritual to physically put your phone away—not just face down, but out of sight. This isn’t just about reducing distractions; it’s about sending a clear message about what (and who) matters most.

Make It a Daily Practice

“Leadership is a human enterprise,” Simon reminds us. “It’s about making people feel seen, heard, and understood.” This means showing up the same way, every day, in every interaction.

Watch for the Ripple Effect

When leaders model this behavior, it spreads. Team members begin to give each other the same undivided attention, creating a culture of genuine listening and respect.

The Parent Test

Simon offers a powerful way to think about this: “The closest analogy I can give to being a great leader is like being a great parent. Yes, I know you don’t get to pick your team sometimes, but you don’t get to pick your children either, and yet you show up with love every day.”

Would you check your phone while your child is telling you about their day? That same principle applies to your team.

The Real Impact

This practice isn’t just about making people feel good—though that matters. It’s about creating the kind of psychological safety that leads to:

More honest feedback
Better problem-solving
Increased innovation
Stronger team bonds

Because when people feel truly seen and heard, they bring their whole selves to work. They take risks. They speak up. They care more.

“Leadership is nothing about being in charge,” Simon reminds us. “It’s about seeing those around us rise.”

Sometimes, that rising starts with something as simple as putting your phone away.

Stop Chasing Happiness and Try This Instead

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

Imagine waking up tomorrow morning and, instead of scrolling through emails, taking a moment to appreciate the simple act of breathing. Not because a meditation app told you to, but because you truly understand how fleeting this moment is.

This shift in perspective is what Alua Arthur, a death doula and New York Times-bestselling author, calls “living like you’re dying”—and it might just transform your daily experience of life.

“I think the most effective practice of gratitude for this life itself is a reminder that I’m going to die,” Arthur shares in her conversation with Simon on this week’s episode of A Bit of Optimism. “When I can remind myself of that, it pulls me right back from the annoyances and the minor grievances and the frustrations.”

The Power of Perspective

It’s not about being morbid. It’s about using the awareness of life’s finite nature to heighten our appreciation of its everyday magic. When we acknowledge that nothing lasts forever—not even our frustrating morning commute or that difficult project—we can find grace in unexpected places.

Arthur discovered this truth through an unexpected encounter on a bus in Cuba, while she was battling burnout as a lawyer. A conversation with a woman facing terminal cancer changed everything. “I also took that invitation to start living like I was dying,” she recalls. The result? A complete transformation in how she experienced daily life.

Turning Awareness Into Practice

Here’s how to apply this wisdom to your own life, starting today:

Start with the Small Things

Notice the simple miracles: your ability to chew food, a roof that doesn’t leak, the warmth of sunlight on your face. These aren’t just nice moments—they’re extraordinary gifts that won’t last forever.

Use Minor Annoyances as Triggers

When something irritates you—traffic, a long line at coffee shop, a delayed meeting—let it remind you of life’s temporariness. As Arthur explains, “There’s a lot of suffering in the world, and yet when I can zoom out and think about what this life is for me at this moment, it allows me to snap back from the annoyances and minor grievances.”

Practice “Grace in the Present”

“Grace is allowing things to be as they are,” Arthur shares, “to be with the gratitude for what is, and for that thing that holds us through everything that we journey through.” This means accepting both the beautiful and difficult moments as part of life’s complete experience.

Finding Joy in Reality

Arthur shares a story about a 95-year-old client who, looking back on her life, said, “First of all, none of it made any sense, but it was one hell of a ride.” This perspective—embracing life’s mysteries and messiness—can free us from the constant chase for meaning and allow us to simply experience what is.

The Practice of Presence

Start small. Tomorrow morning, before you do anything else:

Take three breaths
Name three things that won’t last forever (good or bad)
Express gratitude for this moment, exactly as it is

Remember, this isn’t about achieving some perfect state of enlightenment. It’s about embracing life in all its imperfect glory, knowing that its temporary nature is exactly what makes it precious.

As Arthur reminds us, every moment—even the frustrating ones—is part of “one hell of a ride.” The question is: are you present enough to experience it?

See here for more from A Bit of Optimism.