Author: Team Simon - Page 3

Hate Your Company’s Culture? Here’s One Thing You Can Do About It

Posted on May 16, 2025May 21, 2025 by Team Simon

We’ve all been there—loving what we do but dreading the environment we do it in. The angst-filled meetings, the pessimistic colleagues, the general feeling that everyone would rather be anywhere else. What if you could change that, even without a fancy title or formal authority?

Recently, one of our Optimism Library subscribers wrote to us asking what to do in this situation: “I love what I do, but I can’t stand the vibe at work. Is there any way I can create a little bubble of sanity with my immediate team without coming across as exclusive or weird?”

We took this question to Simon. Here’s what he said.

You Don’t Need Authority to Create Culture

The first myth Simon busted was the idea that you need a formal leadership position to influence culture:

“Yes, it’s called initiative—taking responsibility for the culture without needing any authority,” Simon said. “You can take responsibility for making the four people you work with have a freaking great time at work!”

So, instead of waiting for leadership to fix the culture from the top down, you can start creating the environment you want right where you are.

Small Actions, Big Impact

Simon shared one example that illustrates how simple actions can create meaningful change:

“Recently I had some work done at my house, and I would always announce ‘Pizza Fridays.’ I always tell the foreman, ‘Hey. Every Friday I’m buying pizzas for everybody.'”

The result? “Strangely, more guys seem to work on Fridays,” Simon laughed.

But the impact goes beyond just having more workers show up. “If I have a little thing that I need, everybody says yes. That’s not why I do it, but it is one of the benefits.”

Ideas You Can Implement Today

Simon suggested several simple ways to start creating a positive bubble:

End meetings with a fun tradition: “At the end of a call when you have an extra three minutes… I could do something silly and fun that made it so we all got off the call with a smile.”
Celebrate successes in tangible ways: “One of the companies I know, when they hit their numbers, management makes popcorn in the morning. And so you know when you walk in, if there’s a smell of popcorn, we did well.”
Create moments of connection: Ask team members during lulls in meetings to “tell me one thing we don’t know about you.” Simple, but it makes everyone smile and builds connection.

You don’t need a budget or permission for this sort of stuff—just creativity and initiative.

Will People Think You’re Weird?

The subscriber’s concern about “coming across as exclusive or weird” is valid.

“Will you be seen as weird?,” says Simon. “If you’re the first person dancing, probably. But people get it if you’re trying to do it for the good of everyone. And if you make it voluntary, it’s fine.”

Frame your efforts as “for the good of all,” make them fun, and keep them voluntary. Most people will appreciate what you’re trying to do—even if they’re hesitant at first.

There’s also a perfectly acceptable “selfish” motivation for creating a positive bubble:

“At the end of the day, the selfish part is you’re trying to make it more fun for you to come to work by doing these things,” says Simon.

Making the workplace more enjoyable for yourself by making it more enjoyable for everyone is a win-win approach to culture change.

Simon did add an important caveat: maintain professional boundaries. When someone suggested asking colleagues to share “deep dark secrets,” Simon quickly said, “No, don’t ask that. You still have to be professional.”

The Bottom Line

You don’t need to wait for someone else to fix a bad work culture. With simple, consistent actions focused on bringing people together and celebrating successes, you can create a bubble of positivity that might just grow to transform your entire workplace.

These don’t have to be grand gestures—sometimes it’s as simple as the smell of popcorn in the morning or a genuine question at the end of a meeting.

Facing a challenge at work? Maybe Simon can help. As an Optimism Library subscriber, you’re invited to our exclusive quarterly Live Q&A sessions where you can ask Simon your questions directly.

Competing Against a Coworker for the Same Promotion? Try This Surprising Move

Posted on May 15, 2025May 21, 2025 by Team Simon

The conference room energy shifts the moment HR announces it: one senior position, eight qualified candidates. Suddenly, your lunch buddy or work spouse becomes your rival. That collaborative project you were excited about? Now it’s a showcase where every contribution gets silently scored. Coffee conversations turn into intelligence-gathering missions. Everyone pretends nothing’s changed, but everyone knows everything has.

It’s professional Hunger Games with better lighting and dental coverage.

“How do I manage my relationship with peers who might be competing for the same promotion?” An Optimism Library subscriber sent us this question after finding themselves in this situation. So we took it to Simon, expecting strategic advice about standing out or playing politics. Instead, he referenced a baking show.

“I think that The Great British Baking Show, The Great British Bake Off, is the model for how we should compete,” Simon said.

Wait, what? The show where contestants share ingredients mid-crisis and help each other troubleshoot collapsing cakes? The one where competitors literally assist their rivals?

“Every week somebody gets voted off the island,” Simon said. “There is a winner declared at the end.” Yet despite the high stakes, “they help each other.”

This isn’t just feel-good TV magic. Simon believes it’s the secret to navigating workplace competition.

The Counterintuitive Strategy

“If you’re competing with somebody for the same promotion, then help them. I know it sounds strange and counterintuitive, right?” Simon said.

He illustrated this with actors at auditions, who typically “come in and they all scowl at each other” and “maybe they sabotage each other, cause they see that they’re in competition.”

But Simon advocates for the opposite approach: “The person who comes in who’s like, ‘Hey, really supportive of somebody else, you got this, you’re better for this role than I am,’ helps them read their lines, gives them good notes.”

Why This Actually Works

When you help your competition, several things happen:

“At the end of the day, that person’s confidence is way up, that person’s stress level is way down,” Simon said. “Because they’ve let go of the outcome and they’re in the moment, the odds are their performance is going to be better.”

The benefits extend to you too: “The more you actually help other people, your stress goes down. The more you help other people, your confidence goes up, the more you’re a team player.”

Reality Check on Workplace Promotions

Simon offers perspective on how promotions actually work: “Unless it’s a running race, it’s not always a meritocracy anyway. We don’t know if somebody’s brother-in-law is the son of the… who knows?”

This isn’t cynicism—it’s freedom. “Sometimes the best person does get the promotion and sometimes it doesn’t,” he said. Accepting this allows you to focus on what you can control.

The Essential Mindset

Here’s the crucial part: “You can’t do it to get the promotion. You do it to be a good person and help somebody else,” Simon said.

The approach only works when genuine. “Showing up as the best version of yourself, being a team player and helping somebody else rise” paradoxically “increases your odds” if the system is merit-based.

Putting It Into Practice

Simon recommends starting small: “Try it once in a small scale. Trust me, it actually really works.”

“I have always found in these things that a sense of humor is the best way to go,” he said. Maintaining perspective helps—wish everyone good luck and remember that careers rarely follow straight lines.

The bottom line? “Even when we’re helping each other, the person who deserves it will get the promotion and the person who doesn’t deserve it won’t,” Simon said.

By focusing on collaboration over competition, you often end up performing better while building relationships that last beyond any single promotion cycle.

99 Rejections in a Row? How to Turn Sales Nos into Your Secret Weapon

Posted on May 15, 2025May 21, 2025 by Team Simon

Ever had one of those days where the 15th “no” in a row makes you question your entire career choice? You’re not alone. Recently, one of our Optimism Library subscribers reached out to us, wondering if there’s a better way to handle the constant rejection that comes with sales.

We took this question to Simon, and here’s his response.

When Rejection Becomes Your Laboratory

So many salespeople have been there—staring at the phone after yet another rejection, wondering why they put themselves through this. But what if those “nos” could become your greatest asset?

Simon suggests a subtle mindset shift: “When you get that many nos in a row, it’s an amazing opportunity to start experimenting. If you’re getting rejected anyway, try wildly different approaches and have fun with it.”

Think about it like a sports team rebuilding. They know they’ll lose games in the short term, but each game teaches them something valuable for future wins. Simon encourages sales professionals to “commit to a week of experimentation”—you’re getting rejected anyway, so why not try something completely different?

Learn from the Winners

“Talk to colleagues who get mostly yeses,” says Simon. “During your experimentation, skip making calls and instead sit in on successful colleagues’ calls.”

Sometimes the best lessons come from watching others succeed. If someone in your office is landing 14 out of 15 calls, there’s something to be learned there. What language are they using? How do they open the conversation? What questions do they ask? This kind of observation can be invaluable.

Fishing with a Rod vs. Fishing with a Net

Simon described two fundamentally different approaches to sales:

“There are two different sales approaches: fishing with a rod versus fishing with a net. The rod approach is targeted research and personalization. The net approach is volume-based like call centers.”

If you’re struggling with the volume game—what Simon calls “fishing with a net”—perhaps you’re better suited to “fishing with a rod.” This means fewer, more targeted calls with deeper research and personalization.

“Years ago, I read about a company in Fortune magazine that I thought was incredible and I desperately wanted them as a client,” Simon says. “So I sent them a massive box with a message card rather than a typical envelope that was the usual size. I did this to get noticed—they received this huge box, but in it was only a little letter. When I called the COO to follow up, my opening line was: ‘I’m having a minor love affair with your company.’ He smiled because nobody says that!”

The result? “He asked me to tell him more about myself—I was in.”

Finding Your Approach

Not everyone has the personality to handle constant rejection. If you’re feeling burned out by the “no” parade, Simon suggests considering whether you’re using the wrong approach for your personality type:

“If you’re not comfortable with constant rejection, become a spearfisher instead—make fewer, more researched calls.”

This might mean making just 2 calls a day instead of 15, but spending the rest of your time researching, reading industry publications, and crafting personalized approaches that stand out.

The Bottom Line

Rejection in sales is inevitable, but how you respond to it is entirely up to you. Will you continue the same approach expecting different results? Or will you use rejection as an opportunity to experiment, learn, and perhaps discover an entirely new approach that works better for you?

As Simon says, the goal isn’t to win today—it’s to win more games later. So the next time you’re facing a string of rejections, remember: this might be your perfect opportunity to try something wildly different.

What’s the most unusual approach you’ve tried in sales that actually worked?

Facing a challenge at work? Maybe Simon can help. As an Optimism Library subscriber, you’re invited to our exclusive quarterly Live Q&A sessions where you can ask Simon your questions directly.

The Single Best Way to Handle a Colleague Who Seems Out to Get You

Posted on May 15, 2025May 30, 2025 by Team Simon

Have you ever had that unsettling feeling that a coworker is actively working against you? The colleague who mysteriously leaves you off important emails, speaks over you in meetings, or subtly undermines your ideas to leadership? It’s that gut feeling that something’s off, but addressing it directly seems risky.

One of our Optimism Library subscribers recently brought up this thorny situation: “What should you do when you feel strongly that you have a colleague who does not like you, they’re threatened by you, and you truly feel like they would connive to get you out?”

We took the question to Simon. Here’s what he said.

Is It Real or Is It Your Story?

Simon explained that this sort of workplace tension exists on a spectrum:

“Sometimes it’s misperception driven by our insecurities, sometimes it’s their insecurities, or somewhere in between.”

Before assuming malicious intent, it’s worth considering whether our perception might be colored by our own insecurities or past experiences. As Simon noted, when we’re in a certain frame of mind, we tend to find evidence that reinforces our existing narrative.

Making the Implicit Explicit

Rather than letting tension simmer beneath the surface, Simon advocates for a direct—but careful—approach:

“The best way to relieve tension is to make the implicit explicit—but without making accusations.”

The key is how you frame the conversation. Simon suggests a specific approach that focuses on your perceptions rather than their behavior:

“Have a conversation where you say: ‘Can I talk to you? There’s a story in my mind. I don’t know that it’s true, but I need to share it because it’s affecting how we interact. My story is that you’re out to get me, and I’m seeing things as evidence—like that email you left me off of or that meeting I wasn’t invited to.'”

It’s important to own your perception as a “story” that may or may not be accurate. You’re making it about your experience rather than their intentions.

“Make it about you and not them,” says Simon. “Because if you accuse them, they’ll get defensive.”

This way, you create space for a conversation rather than a confrontation.

Reading the Response

Regardless of how the other person responds, you’ll get valuable information.

“Most of the time, this approach will lead to a productive conversation,” Simon says. But even if it doesn’t, “If they get aggressive in response, you’re getting valuable data.”

An overly defensive or aggressive response might actually confirm your suspicions, giving you important information about how to proceed.

The Strategic Escalation

If the direct conversation doesn’t resolve the tension, Simon suggests a strategic approach to involving leadership:

“If needed and you have a good relationship with your boss, you might say: ‘I need advice. I’m struggling with this colleague relationship, and it’s bad for the company. I don’t know what to do.'”

This puts the tension on your boss’s radar without coming across as tattling or undermining your colleague. You’re positioning yourself as solution-oriented rather than complaint-driven.

The Toxic Culture Exception

There’s one scenario where a different approach might be necessary:

“If you find yourself in an organization with a culture of backstabbing, that’s a poorly led organization,” says Simon. “We’ve seen it at places like Wells Fargo, where fear drives behavior and good people do horrible things to survive.”

In truly toxic environments where unethical behavior is normalized, Simon’s advice is clear: “If you’re in such a toxic environment, you should get out before you do something you’ll regret.”

The Hopeful Reality

Despite the drama that workplace tension can create, Simon offered a reassuring perspective: “The good news is that truly toxic colleagues are not that common. Most issues are misperceptions.”

This reminds us that in most cases, what feels like targeted undermining might actually be miscommunication, different working styles, or even a colleague dealing with their own insecurities.

The Bottom Line

Workplace tension with colleagues is inevitable at some point in most careers, but how we address it can make all the difference in the outcome. By owning your perception as a “story,” initiating a non-accusatory conversation, and being strategic about escalation if needed, you create the best possible conditions for resolution.

And remember—while the occasional toxic colleague does exist, most workplace tension stems from misperception rather than malice.

Facing a challenge at work? Maybe Simon can help. As an Optimism Library subscriber, you’re invited to our exclusive quarterly Live Q&A sessions where you can ask Simon your questions directly.

That Gut Feeling Your Job’s at Risk? Here’s What to Do About It

Posted on May 15, 2025May 30, 2025 by Team Simon

We’ve all had that moment, when something at work just feels off. You’re being left out of meetings. Important emails no longer include your name. Your manager’s tone has subtly changed.

It’s a deeply unsettling experience. And it often leads to a paralyzing question:

How do you talk to your manager about it without sounding paranoid…or making things worse?

One of our Optimism Library subscribers recently asked us this exact question:

“When you have that gut feeling your job might be in danger, what’s the best way to bring it up without putting a target on your back?”

We turned to Simon for guidance. His response might surprise you.

The Fraying Rope of Trust

Simon shared a story about a friend who had been in this exact situation:

“My friend started noticing weird things at work—being left off key emails, excluded from meetings he’d normally be part of.”

His friend described trust as a rope: when you first join a team, you don’t put your full weight on it. But over time, as trust builds, you begin to lean on it more and more.

“He said, ‘I looked to the left, I looked to the right, and I could see my rope fraying.’”

The Common Mistake We All Make

When we sense our job might be in trouble, the knee-jerk reaction is to work harder. Stay late. Say yes to everything. Prove your value.

According to Simon, that’s exactly the wrong approach:

“He made the biggest mistake—he tried to shore up their rope instead of taking the weight off his.”

It’s like trying to save a failing relationship by overcompensating: cooking more dinners, buying more flowers—when what you really need is a conversation.

The Better Approach: Take Weight Off the Rope

Simon suggests a counterintuitive but powerful move: stop guessing, and start talking.

“What my friend should have done was knock on the door and say, ‘Can we talk?’”

The trick is to frame the conversation in a way that’s not accusatory or defensive, but constructive and vulnerable:

“I have a story running in my head. If it’s not true, I need to clear it up. But if it is true, we need to talk. I want to be valuable here—and if I’m not, let’s figure out a plan to grow or a way to exit with dignity.”

Why This Works: From the Manager’s Perspective

Many managers avoid difficult conversations because they’re unsure how you’ll respond. Fear of conflict or backlash often keeps them silent longer than they should be.

That’s why initiating the conversation yourself can be so powerful:

“If you say, ‘If something’s coming, it’s okay. Just help me leave with dignity and some lead time,’ you make it easier for them to be honest.”

Managers Are Human Too

Simon shared his own experience:

“I’ve had to let someone go and wished I’d told them sooner. But I hesitated—because I didn’t want to be the bad guy.”

Understanding that managers are human—and that silence often comes from discomfort, not cruelty—can help you approach the situation with empathy.

Build a Bridge of Empathy

Yes, it may seem unfair to make your manager feel safe about potentially letting you go. But that’s the reality in many workplaces.

“A lot of employees say, ‘I shouldn’t have to do that.’ And you’re right. But this is the real world.”

By creating safety in the conversation, you increase your chances of getting the clarity and respect you deserve—whether it leads to a plan for improvement or a dignified departure.

A Script You Can Use

If you’re not sure how to start, here’s a version of the conversation Simon recommends:

“I can only imagine the pressure you’re under. And I get that letting someone go might alleviate some of that. If that person might be me, I understand. I’m not angry. I just want to be part of the process, so it’s easier for both of us.”

This simple, human approach fosters honesty, dignity, and even collaboration—qualities that stand out no matter the outcome.

The Bottom Line

When you suspect your job might be in jeopardy, ignoring the signs or over-performing can often backfire.

Simon offers a third way:
✔️ Acknowledge your gut feeling
✔️ Start a respectful conversation
✔️ Position yourself as a partner, not a problem

You may not be able to control the decision—but you can control how you handle the uncertainty. And sometimes, that shift in approach is enough to change the story entirely

Want More Career Advice Like This?

As an Optimism Library subscriber, you get access to our exclusive quarterly Live Q&A sessions—where you can ask Simon your questions directly.

Facing a challenge at work? Bring it to the table. You might be one conversation away from clarity.

What Most Leaders Miss When Looking at Their Data

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

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

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

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

The Human Behind the Number

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

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

Then, something remarkable happened.

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

What happened next? The fundraising numbers skyrocketed.

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

The Opportunity of Ethical Clarity

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

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

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

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

The Simple Practice That Changes Everything

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

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

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

The Ripple Effect of Rehumanizing Leadership

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

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

A Leadership Challenge for You

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

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

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

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

The Leadership Secret Hidden in Plain Sight

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

Imagine this scene: a remote air base in Iraq, the constant hum of aircraft and generators punctuating the dry desert air. A young officer, recently promoted and given her first command, sits alone in her trailer after another grueling day where nothing seems to be working. Six months into a year-long deployment, she’s crying herself to sleep night after night, questioning every decision, regretting her career choice, and feeling like an absolute failure.

This was DeDe Halfhill’s reality during what would become the most defining leadership experience of her career.

DeDe spent 25 years in the Air Force, rising to the rank of colonel in a profession dominated by men. As a public affairs officer, she served as a strategic advisor to some of the military’s most senior leaders, including Chiefs of Staff and the Chairman of the Joint Chiefs during critical moments of the War in Iraq. After retiring from the military, DeDe has become a highly sought-after leadership consultant, helping organizations navigate the same challenges she faced throughout her military career.

This week, DeDe sat down with Simon in the latest episode of A Bit of Optimism (which you can view in full here or click to listen here).

As DeDe shared with Simon, she faced a perfect storm of leadership challenges. She had been:

Promoted early (about four years of experience behind her peers)
Given her first command (while her peers were on their second)
Deployed to Iraq for 365 days
Put in charge of a squadron with operations she had no experience in
Made responsible for “feeding, fitness, and fun” for an entire air base

“Everything I had envisioned about who I would be as a leader did not show up in that experience,” DeDe said.

For six long months, she battled against what felt like inevitable failure. Nothing worked. Her inner critic ran at “max volume,” constantly telling her she was “the absolute worst thing that has ever happened to leadership.”

Then came the breakthrough that would change everything.

The Unexpected Power of Acceptance

One night, after another discouraging day, DeDe had what she calls her “mini breakdown” followed by a moment of clarity.

“If I have failed—and maybe I have, maybe I’m not meant to be a commander—what impact do I really want to have? What do I want these people, who I have been entrusted to care for, to know?”

The answer came to her with surprising simplicity: “I want them to know they matter. I want them to know what they’re doing here is not in vain.”

With this shift in thinking, everything changed. Instead of continuing to fight against her perceived failure, she accepted it and moved her focus entirely to making her people feel valued.

At first, the results were subtle. DeDe felt better, which meant she wasn’t as stressed or “barking as much.” She wasn’t tied to outcomes anymore because she was more concerned about the people. Then something magical began to happen.

“You could see a tangible shift in the way they laughed with one another,” DeDe said. “The way they came to me with opportunities and new ideas. I could see the way my own officers took a breath.”

The stress level of the entire organization dropped noticeably. And almost as a side effect, performance improved. The command that DeDe thought she had failed to turn around began to thrive.

By the end of her deployment, she had built a team that would “willingly follow her anywhere.” What had started as her greatest professional disappointment became her proudest achievement.

When We Make People Feel Like They Matter, Everything Else Follows

Our conventional thinking often gets this backward. We focus on metrics, targets, and performance, hoping that achievement will make people feel valued. But as DeDe discovered in the crucible of combat leadership, the path actually runs in the opposite direction.

This isn’t just a “feel-good” philosophy—it’s practical leadership wisdom born from one of the most challenging leadership environments imaginable.

Bringing This Insight to Your Leadership

Here’s how you can apply DeDe’s transformative insight in your own leadership context:

The Morning Intention:
Start each day by asking: “How will I show my team they matter today?” This simple question reorients your focus before getting caught in the whirlwind of tasks and targets.
Create “Recognition Rituals:”
Develop consistent ways to recognize not just what people achieve, but who they are. DeDe’s team members were constantly “taking the brunt of everyone else’s stress.” Your recognition can be the counterweight to the difficulties they face.
Practice the Pause:
When you feel yourself becoming overly focused on metrics or disappointed by performance, pause and ask: “What would change if I accepted where we are right now and focused solely on making my people feel valued?”
Make Space for Stories:
Create opportunities for team members to share their experiences and challenges. As DeDe learned, when people feel seen and heard, their entire relationship with work deepens.

The Ultimate Leadership Paradox

What makes DeDe’s story so powerful is that it was only when she stopped trying to be an exceptional leader that she became one.

By accepting what she perceived as failure and shifting her focus to making her people feel they mattered, she achieved everything she had originally set out to do—and more.

As Simon reflected after hearing DeDe’s story: “If you take care of them in the good times, they will take care of you in the hard times. That’s how leadership works.”

Ready to show your team they matter, but not sure where to start? Simon and Zach Mercurio developed a course that teaches the essential leadership skills you need to inspire trust, empower others, and become a leader others believe in. Check it out here.

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.

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