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The 3 Skills 57% of Middle Managers Are Desperately Missing

Posted on August 25, 2025August 27, 2025 by Team Simon

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

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

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

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

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

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

The 3 Skills That Change Everything

1. Human-Centered Communication

The skill 55% struggle with most

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

– How do you correct someone without crushing their spirit?

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

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

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

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

2. Virtual and Hybrid Leadership

The challenge facing 43.4% of managers

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

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

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

3. Emotional Intelligence and Resilience

The foundation 75% are missing

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

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

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

The Path Forward

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

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

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

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

The potential is already there.

We just need to notice it.

7 Things Gen-Z Employees Shouldn’t Say to Their Bosses

Posted on July 10, 2025July 10, 2025 by Team Simon

Imagine a time when newspaper headlines are absolutely roasting an entire generation of workers. They’re calling them lazy, entitled, and fundamentally allergic to hard work. The media is having a field day tearing apart these young employees who just don’t seem to “get it.”

Sound familiar?

Plot twist: Those headlines weren’t about Gen-Z. It was the early 1990s, and they were about Gen-X.

“The paradox is that on one hand, members of this generation don’t want to be ruled by the company. They want to have a life. On the other hand, they’re impatient waiting for job promotions and want all the perks associated with ‘paying one’s dues.'”

“The boring twenties: grow up, crybabies, you’re America’s luckiest generation.”

“They crave entertainment, but their attention span is as short as one zap of a TV dial.”

Welcome to the timeless tradition of workplace moral panic. Every generation gets the same treatment with slightly different vocabulary. Gen-X was “slacking.” Millennials were “entitled snowflakes who needed participation trophies.” Now Gen-Z is “too authentic” and “doesn’t understand professionalism.”

As Mark Twain never actually said (but definitely should have): History doesn’t repeat, but it sure does rhyme.

Here’s What’s Actually Happening

If you’re a member of Gen-Z, you grew up in a world where authenticity was currency. Your parents told you to “just be yourself,” social media rewarded realness over perfection, and then COVID hit. Suddenly everyone was working in sweatpants for two years. Meanwhile, your bosses grew up watching movies where people wore actual suits to work and said things like “synergy” without a trace of irony.

Add to that the fact that you witnessed the 2008 financial crisis at a formative age, watching parents and loved ones navigate layoffs and economic uncertainty. Of course you approach work differently. You’ve seen how quickly “company loyalty” can evaporate when budgets get tight.

But here’s the thing: those older generations? They were once workplace rookies too, figuring it out as they went along. They’re not trying to crush your spirit. They’re just operating from a different playbook while trying to keep their own careers intact.

So let’s bridge that gap. The following seven phrases might feel natural to say, but they’ll make your boss’s eye twitch, and potentially derail your career trajectory. This is about more than selling your soul to corporate culture; it’s about strategic communication.

1. “That’s Not My Job”

Why it backfires: Every generation before you heard this phrase as code for “I’m not a team player.” Even when you’re technically right about job scope, it lands like a brick wall.

The reality: Boundaries are crucial, and you shouldn’t be expected to do everyone else’s work. But there’s a way to protect your time without sounding inflexible.

Try this instead: “I’m happy to help with that. Can we discuss how this fits with my current priorities?” You’re still protecting your bandwidth, but you’re doing it in Corporate Speak™.

2. “I Don’t Check Email After Hours”

Why it backfires: Boundaries are beautiful, and work-life balance is essential. But announcing this like you’re leading a revolution can come across as inflexible, even when you’re just trying to set clear expectations.

The reality: Different roles and industries have different norms around availability. What matters is being clear about expectations upfront.

Try this instead: “I typically handle emails during business hours to ensure I can give them my full attention. If something urgent comes up after hours, feel free to call me at any time and I’ll jump right on it.” Same boundary, more professional packaging.

3. “Can We Do This Remotely Instead?”

Why it backfires: You’ve experienced the productivity boost of working from home, and you know that commuting two hours for a 30-minute check-in doesn’t make sense. But asking to work remotely for everything—especially when you’re new—can signal that you’re not invested in team culture.

The reality: Remote work is still being figured out by most organizations. Some things genuinely work better in person, especially relationship-building and complex problem-solving.

Try this instead: “I’m flexible on location for this. What works best for the team?” Show that you’re thinking about effectiveness for everyone, not just convenience for you.

4. “I’m Not Really a Morning Person”

Why it backfires: Here’s some tough love: no one cares about your circadian rhythms in a 9-to-5 world. Your boss probably isn’t a morning person, either.

The reality: Most workplaces still operate on traditional schedules, and being present (mentally and physically) when you need to be is part of the job.

Try this instead: Work on solutions rather than announcements. Develop a morning routine, adjust your sleep schedule, or find other ways to be alert when it matters. If you genuinely need accommodation, discuss it privately with HR.

5. “This System is So Outdated”

Why it backfires: Yes, you’re probably right. Yes, there’s definitely a better app for that. Yes, you could build something more efficient in your sleep. But leading with criticism makes you sound like you think everyone before you was incompetent.

The reality: Sometimes organizations change slowly for good reasons, whether it’s legacy systems, budget constraints, training costs, and the risk of disrupting workflows.

Try this instead: “I’ve been thinking about ways we might streamline this process. Would you be open to discussing some options?” Same observation, but now you’re a problem-solver instead of a critic.

6. “I Saw Your Personal Instagram/TikTok/Facebook”

Why it backfires: Just because your boss accepted your follow request doesn’t mean their weekend kayaking trip or their kid’s graduation photos are appropriate conversation starters at work. The lines between personal and professional are blurry enough. No need to make them worse.

The reality: Social media boundaries at work are still evolving, and many people prefer to keep their personal lives separate from their professional relationships.

Try this instead: Keep the social media observations to yourself, even if their vacation photos from 2019 were genuinely amazing.

7. “This Could Have Been an Email”

Why it backfires: Look, you’re absolutely right. That 45-minute meeting about the meeting you’re going to have about the project timeline definitely could have been a Slack message. But saying this out loud is like pointing out that someone’s expensive haircut looks terrible. In other words: It’s accurate, but not helpful.

The reality: Your boss probably knows it too, but they’re dealing with their own boss who loves meetings about meetings. Sometimes the meeting exists for political reasons you’re not seeing.

Try this instead: Just smile, take notes, and save your energy for battles that matter. If you want to suggest more efficient communication, do it privately and focus on solutions.

The Bottom Line

We’re not trying to turn you into a corporate robot. Your authenticity, fresh perspective, and ability to see through outdated systems are genuinely valuable assets. But learning to translate your thoughts into workplace-appropriate language is simply strategic communication.

Think of it like code-switching. You probably talk differently to your grandmother than you do to your college friends, right? Same energy, different audience.

Your ideas matter. Your perspective is needed. Your generation is already reshaping how work gets done. You just need to package it in a way that is effective for everyone, especially you.

For more ways we can help you grow at work, you can explore Simon’s 250 career-building lessons here.

The Simple Weekend Habit That Makes You Less Unhappy

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

Picture this: You’re scrolling through your phone on a Saturday morning, already feeling the weight of the week ahead pressing down on your chest. Your mind is racing through your to-do list, replaying last week’s stressful moments, and somehow managing to worry about Monday’s meetings all at the same time. Sound familiar?

We’ve all been there. But what if we told you that one of the world’s leading happiness experts has a simple practice that could help you, and it only takes half a Saturday?

When Google’s Former Chief Business Officer Discovered the Power of Doing “Nothing”

Mo Gawdat is more than your typical happiness guru. The former Chief Business Officer of Google X—the guy who helped open Google’s businesses worldwide—knows a thing or two about the relentless pace of modern life. But after experiencing unimaginable loss and depression despite his massive success, Mo discovered something profound: sometimes the most productive thing you can do is appear to do nothing at all.

In a recent episode of A Bit of Optimism, Mo shared what he calls his “Saturday practice,” a simple routine that has become the cornerstone of his happiness philosophy.

The Magic of Saturday Until 2 PM

Here’s Mo’s game-changing approach: “Most Saturdays, my alarm clock is set to 2:00 PM. Doesn’t matter when I wake up, but I am in reflection mode until 2:00 PM.”

But this isn’t just lounging around (though honestly, that sounds pretty great too). Mo has turned this time into what he calls “mini silent retreats.”

“I’m completely alone,” he told Simon. “No interaction with time pieces. So I don’t know what time it is. No interaction with the internet. No interaction with news. I’m not checking my WhatsApp. I’m completely with my little remarkable, or paper and pen. And basically thinking.”

The Stress Audit That Actually Works

During these Saturday sessions, Mo does something most of us avoid like the plague: he actually deals with his stress head-on. But not in the way you might think.

“I do a stress stock taking, basically I write down everything that stressed me the week before and I basically scratch out the shit that I don’t want to stress me the next week.”

So… you can decide what gets to stress you? According to Mo, absolutely.

“For example, you know, this annoying friend that’s constantly negative will probably receive a text saying, ‘Hey, can we make our interactions a little more positive or maybe make them less?'”

The man literally addresses his stressors one by one. That friend who always complains? That meeting that serves no purpose? That news app that sends you into a doom spiral? He tackles them systematically, like a happiness detective solving the case of his own wellbeing.

Meet Becky: The Technique That Silences Your Racing Mind

But Mo’s Saturday practice gets even more genius. He’s developed what he calls the “Meet Becky” technique, and we’re slightly obsessed with it.

“I call my brain a third party name. Becky was the most annoying girl in school. So literally, you know those people that walk to you all the time and just say annoying things and then walk away with no solutions? That’s your brain.”

Here’s how it works: Set a timer for 20 minutes. Write down every single thought your brain throws at you. But with one crucial rule: no idea gets repeated twice. Mo explains what happens next:

“I guarantee you, normally around minute 11 or so, you go like, ‘so what else?’ And your brain goes like, ‘um, that’s it really.’ And it completely runs out of ideas. I promise you this is as close to heaven as you’ll ever get. Total silence.”

The result? “A few minutes later it starts to tell you nice things… It’s run out of crap.”

Why This Isn’t Just Another Self-Care Trend

Look, we know what you’re thinking. Another wellness guru telling us to meditate and journal? But here’s what makes Mo’s approach different: it’s ruthlessly practical.

This is about more than achieving some zen-like state. It’s about recognizing that “we think that life should be stressful, especially busy ones because, you know, it’s a trophy.” But what if that trophy is actually weighing us down?

Mo puts it perfectly: “You become more productive with silence sometimes. You become more productive by doing nothing sometimes.”

The Science Behind the Silence

What Mo discovered aligns with what neuroscience has been telling us for years. Our conscious brains can only process about three feet of information around us, but our subconscious brains have access to the equivalent of about 11 acres. When we’re constantly “thinking,” we’re actually limiting our problem-solving capacity.

This is why our best ideas come in the shower, during walks, or in those quiet moments when we’re not actively trying to think. Mo’s Saturday practice creates intentional space for this kind of processing to happen.

Your Saturday Challenge

So here’s our challenge to you: try one Saturday until 2 PM. Not the full 40-day silent retreat Mo does annually (though if you’re feeling ambitious, go for it), but just one Saturday morning of what he calls “the activity of doing nothing.”

Set your alarm for 2 PM. Put the phone away. Grab a pen and paper. Do Mo’s stress audit. Try the “Meet Becky” technique. See what happens when you give your brain permission to empty itself out.

As Mo says, “Everyone can” find this time. It’s just a matter of choosing to prioritize it.

The Single Best Way to Be a More Assertive Leader

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

Imagine you’re leading a strategy meeting. Your team is split on a major decision. Half are pushing for a bold, expensive pivot, half are advocating for a safer, proven approach. Everyone’s looking at you to make the call.

Your instinct screams for the bold option. You could shut down the debate right now and move forward with confidence. But what if you did something else?

“Before I share my thoughts, I want to make sure I truly understand both sides. Joe, you’re advocating for the conservative approach. If I were completely convinced that option B is right, what would my strongest arguments be? What risks am I seeing that others might be missing?”

Then to the other side: “And Caitlin, if I were absolutely certain that option A is wrong for us right now, what would I be most worried about?”

Instead of a tug-of-war where everyone digs deeper into their positions, you get something more productive: people reveal their real concerns and genuine insights. They feel heard. And you make a decision with complete understanding of every angle.

This isn’t indecision. This is what real assertiveness looks like.

The Practice That Changes Everything

Learn to argue both sides of every important issue.

Before advocating for any position that matters, spend time genuinely understanding and articulating the strongest possible version of the opposing viewpoint. This isn’t about playing devil’s advocate. It’s about doing the intellectual work to comprehend why reasonable people might see things differently.

Why This Works

Most assertiveness training teaches us to be more confident in our own position. But confidence without understanding often comes across as arrogance. When leaders can argue both sides of an issue:

We become more credible. People trust leaders who’ve considered multiple perspectives before reaching conclusions.
We become more persuasive. Understanding real concerns means you can address them directly instead of talking past them.
We become more collaborative. Teams feel safer challenging leaders who’ve already challenged themselves.
We become more decisive. Decisions made with full understanding of trade-offs are stronger and more sustainable.

How to Practice This

Choose Your Issue: Pick something you’re advocating for: a strategic direction, policy change, or resource allocation.
Build the Opposing Case: Spend real time researching the strongest arguments against your position. What legitimate concerns exist? What risks might you be overlooking?
Practice the Opposition: Articulate the opposing viewpoint out loud until someone who holds that view would say, “Yes, that’s exactly what I believe.”
Integrate What You Learn: When advocating your position, acknowledge legitimate concerns: “I know some of us are worried about X, and that’s valid. Here’s how we can address that while moving forward with Y.”

The strongest leaders aren’t those who never doubt themselves. They’re those who doubt themselves privately so they can be confident publicly.

Instead of: “We need to implement this strategy because it’s clearly the right approach.”

Try: “I know there are legitimate concerns about the risks and costs of this strategy. I’ve considered alternative approaches, and here’s why I believe this path gives us the best chance of achieving our goals.”

The difference is night and day. One approach shuts down conversation. The other opens it up.

When leaders combine thoughtfulness with the courage to speak up for what they believe, they become leaders worth following.

No One Learns to Swim on the Shore

Posted on May 27, 2025May 27, 2025 by Simon Sinek

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

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

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

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

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

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

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

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

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

12 Words That Kill Trust (And What to Say Instead)

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

We’ve all been there.

That moment when your boss looks you in the eye and says “just trust me” before completely tanking the project. Or when someone starts a sentence with “with all due respect…” and you brace for impact because you know respect is about to leave the building.

Last Tuesday, we started tracking these trust-destroying phrases in our office. By Friday, we’d filled an entire whiteboard. That’s when we realized: these aren’t just annoying corporate-isms. They’re relationship killers disguised as professionalism.

We dove deep into the research, talked to communication experts, and discovered something amazing: for every trust-killer, there’s a trust-builder. Simple word swaps that transform bad conversations into productive ones.

Here are the twelve phrases murdering trust in offices everywhere—and exactly what to say instead:

1. “Just trust me”

Why it kills trust: The verbal equivalent of “don’t look behind the curtain.” If someone needs to ask for trust, they probably haven’t earned it. Real trust is built through actions, not demanded through words. Trust must be earned through consistent actions and transparency.

Say instead: “Here’s my thinking…” or “Let me show you why this will work…”

2. “With all due respect…”

Why it kills trust: Nothing respectful has ever followed these words. It’s a warning shot that disrespect is incoming.

Say instead: “I see it differently…” or “From my perspective…”

3. “No offense, but…”

Why it kills trust: Spoiler alert: Offense is absolutely intended. This phrase is like saying “I’m about to insult you, but I’m giving myself a free pass.”

These types of disclaimers can appear passive-aggressive and diminish trust.

Say instead: “I have different thoughts on this…” or just share your perspective without the disclaimer.

4. “I’m just being honest”

Why it kills trust: Code for “I’m about to be cruel and call it virtue.” Honesty without kindness is just brutality with a bow on top.

Note that this phrase can imply previous dishonesty and be used to justify insensitive comments.

Say instead: “My perspective is…” or “I want to share some feedback…”

5. “That’s not my job”

Why it kills trust: The ultimate team killer. It says “I’m here for me, not for us.” Nothing screams “not a team player” louder.

This phrase can cause lasting damage to working relationships, making the speaker appear unhelpful and disengaged.

Say instead: “That’s outside my expertise, but let me connect you with…” or “I can help you find the right person…”

6. “I told you so”

Why it kills trust: Nobody likes a retroactive genius. This phrase prioritizes being right over being helpful.

Say instead: “What can we learn from this?” or “How can we prevent this next time?”

7. “It is what it is”

Why it kills trust: The shoulder shrug of phrases. It signals you’ve given up and expect everyone else to do the same.

This phrase communicates resignation and a lack of accountability, which can demoralize teams.

Say instead: “Given our constraints, here’s what we can do…” or “Let’s work with what we have…”

8. “That’s above my pay grade”

Why it kills trust: Translation: “I don’t care enough to help.” It’s passing the buck in a fancy wrapper.

Be warned that this can come across as deflective and undermine your credibility and influence.

Say instead: “I’ll need to bring in [specific person] for that decision” or “Let me find out who can help with this…”

9. “Let’s take this offline”

Why it kills trust: Often code for “I don’t want witnesses to this conversation.” It can make others feel excluded or suspicious.

Say instead: “This deserves more time. Can we schedule a follow-up?” or “This needs a deeper dive. Who should be included?”

10. “It’s not personal, it’s just business”

Why it kills trust: Everything at work involves persons, so it’s all personal. This phrase is often used to justify treating people poorly.

Say instead: “I know this impacts you. Let’s talk about how we can move forward…”

11. “I don’t have time for this”

Why it kills trust: What people hear: “You’re not important enough.” It dismisses both the issue and the person raising it. This phrase makes employees feel undervalued and like their concerns don’t matter.

Say instead: “I want to give this proper attention. When can we dive deeper?” or “This is important. Let me check my calendar…”

12. “Whatever you think is best”

Why it kills trust: Passive-aggressive surrender. It sounds supportive but often means “I disagree but won’t engage.”

Remember: Vague agreement can be more harmful than disagreement—it signals disconnection and lack of support.

Say instead: “I trust your judgment on this” (if you do) or “I have some concerns. Can we discuss?”

The Trust-Building Alternative

Trust isn’t built through perfect words—it’s built through consistent actions. But words matter because they reveal our intentions. Instead of these trust-killers, try:

“Help me understand…”
“What would success look like to you?”
“I’m curious about your perspective…”
“Thank you for bringing this up…”
“Let’s figure this out together…”

And the most powerful trust-building phrase in any language?

“I was wrong.”

Use it wisely. Use it honestly. Watch trust grow.

And for better ways to communicate at work, check out Simon’s Optimism Library.

Tired of Soul-Crushing Corporate Jargon? Help Us Bury the Worst Acronyms

Posted on May 19, 2025June 10, 2025 by Team Simon

Listen, we need to talk. Pull up a chair, grab your coffee (or emotional support beverage of choice), and prepare yourself for what might be the most cathartic experience of your corporate life.

We’re officially opening what we’re calling the Acronym Cemetery, and we need your help filling it.

But first, a confession: We work for Simon Sinek, and he has a rule that drives new hires (usually the ones who used to work at big corporations) absolutely bonkers for their first month—no acronyms allowed. Zero. Zilch. Nada.

“PDP” for product detail page? Nope. Write it out, marketing guy.

“AOP” for Simon’s product The Art of Presenting? Absolutely not.

“EOD?” You better specify 5pm, pal.

We actually measured it (because what else would we do with our acronym-free time?), and we’re 79% happier as a result. That’s a real stat we definitely made up while writing this.

The Breaking Point

Recently, some of us were in a meeting with a vendor who said something along the lines of, “We need to leverage our KPIs ASAP to maximize ROI on our B2B SaaS platform while ensuring our SMEs align with the RFP requirements EOD.”

We blacked out. All of us. Simultaneously.

When we came to, we were standing in a misty graveyard, surrounded by weathered tombstones. But these weren’t ordinary graves. No, these were the final resting places of acronyms that had been worked to death in conference rooms across America.

The Grand Opening

Here’s the thing: We’ve got plots ready, shovels sharpened, and eulogies half-written. But we need your nominations for which acronyms deserve burial first.

The inaugural residents include:

COB (Close Of Business) 1997-2024

“Died of ambiguity, leaving everyone guessing when the deadline actually was”

Last words: “Is that New York time or Pacific?”

RTO (Return To Office)

2020-2024

“Died from causing anxiety in countless company-wide emails”

Last words: “Please refer to the updated hybrid work policy for your RTO schedule”

OTP (On The Phone)

1998-2024

“Succumbed to obsolescence when chat statuses made it redundant”

Last words: “BRB, OTP with client”

Send Us Your Worst

But we know you’ve suffered more. We know there’s an acronym out there that makes your eye twitch every time it lands in your inbox. The one that makes you question your career choices. The one that haunts your Slack notifications.

WE WANT THEM ALL.

Submit your most hated corporate acronyms in the comments. Tell us:

Which acronym hurt you
How it died (overuse? meaninglessness? passive-aggressiveness?)
What its last words were

Feel free to submit your worst acronym offenders to [email protected]. Be specific. Be brutal. Channel all that repressed rage from years of not understanding what anyone was talking about in meetings.

Together, we can create a world where communication actually… communicates.

Because here’s the truth: This whole cemetery project might seem like a joke (and it mostly is), but it’s really about something bigger. Every acronym we bury is one less barrier between what we mean and what we say. Every spelled-out phrase is a tiny victory for clarity. Every abandoned piece of jargon brings us closer to the radical idea that work communication should actually make sense.

We believe that when people understand each other, magical things happen. Trust builds. Ideas flow. Work becomes less about decoding corporate hieroglyphics and more about doing things that matter.

So yes, we’re building a cemetery. But really, we’re clearing the path for better conversations, stronger connections, and the revolutionary notion that when someone says something at work, everyone should actually know what they mean.

The cemetery gates are open. The burial plots are ready. We just need your victims.

With love, properly labeled shovels, and a dream of jargon-free meetings,

Team Simon

P.S. – If you’re still using “low-hanging fruit,” that’s not an acronym but we’ll bury it anyway. Some things just need to die.

P.P.S. – Seriously, Simon will personally engrave the tombstones if we get enough submissions. (He probably won’t, but we’re hoping he will.)

Submit your acronyms to [email protected].

And for better ways to communicate at work, check out Simon’s Optimism Library.

What to Do When Your Company Has Zero Promotion Path

Posted on May 19, 2025June 10, 2025 by Team Simon

Most of us who’ve worked at a small company know this moment: You’re two years in, basically running entire departments, but your title is still something vague like “marketing coordinator.” There’s no org chart on the wall because there are only twelve of you. The CEO sits ten feet away but has no idea what a promotion would even look like because they’re too busy keeping the lights on.

So what do you do when you want to advance but there’s literally nowhere to advance to or any plan for advancement at all? Such was the frustration of an Optimism Library subscriber who wrote in this question: “My company doesn’t have clear promotion criteria. How do I navigate this ambiguity and still position myself for advancement?”

We brought it to Simon to get his take on navigating career growth when your company treats promotion paths like jazz improvisation rather than corporate ladders.

Simon’s response was direct: Ask for clarity. But how you ask makes all the difference.

“This is very common in smaller companies,” Simon said. “Bigger companies, because they’re corporate, they tend to be a little more organized for this kind of thing.” In contrast, “entrepreneurial ventures are kind of like, woohoo!, right?”

He added that personality and relationships often factor into these decisions: “Sometimes it is and sometimes it isn’t” fair—but that’s the reality.

The Assumption Problem

“One of the worst things you can do if there’s ambiguity is assume that it’s somebody else’s responsibility,” Simon said. The dangerous part? Your boss might think everything is perfectly clear.

Simon has been on the other side of this confusion: “I’ve definitely been guilty of this, you know, where I’ve been the leader of a team, and I think everything is crystal clear.”

Then reality hits at year-end: “I’m missing key information. I promote one person but not another. I give bonuses to some but not others, and everyone’s like, ‘What?’ I’m thinking, ‘You knew this was coming, right?’ But they’re like, ‘We had no idea.'”

The Solution Script

Instead of criticizing the company’s lack of structure, Simon suggests positioning your request as asking for help:

“Hey boss, I need help, right? I want to be the best version of myself. I want to outperform. I want to do right by this company. I want to hit all of my goals, all the goals you have for me, and it will really help me if you and I could spend a little time and actually write down what your expectations are of me, if we can have that discussion so that I can give you everything you expect of me and more.”

The key elements:

Ask for help
Focus on excellence (not just promotion)
Take ownership of performance
Create written documentation

This perspective changes the conversation from confrontation to collaboration.

Alternative Approach

Simon offers another version that acknowledges your boss’s existing expectations:

“I need your help. I know you have expectations of me. I know you have expectations of us. It would be really helpful so that I meet all of your expectations, that I can find out what’s in your mind and put it on paper so that I can give you what you want and more.”

This script:

Validates that expectations exist
Positions you as eager to exceed them
Creates concrete documentation
Benefits both parties

“So ask for help, instead of complaining about what’s wrong,” Simon said. When faced with organizational ambiguity, the person who creates structure often benefits most from it.

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.

How to Make Your Boss Notice Your Work (Without Looking Like You’re Bragging)

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

“How do I make my contributions more visible to leadership without coming across as self-promoting or bragging?”

This question from an Optimism Library subscriber touches on a universal workplace challenge—getting recognition without seeming like you’re fishing for it.

Simon’s answer reframes the approach: “Nobody cares about you, right?”

Before you take offense, hear him out. His point is about shifting focus from personal recognition to organizational success. “How do you help your boss succeed?”

Understanding Your Boss’s Style

Simon admits he’s often that boss who doesn’t track daily operations closely. “I tend to not have my finger on the pulse cause I’m very laissez-faire,” he said. “And so I sometimes don’t know what people are up to, and so that’s why I like status meetings. I’m like, tell me what you’re up to.”

If your boss operates similarly, Simon suggests positioning visibility as a contribution to their success:

“Hey, I thought of an idea. In an effort to help you know everything that we’re doing so that you can share with your boss, like the stuff that you’re getting done in your department, what do you think about some sort of status meeting or status report where all of us can show you what we’re working on?”

The Accountability Approach

Simon’s second strategy might seem counterintuitive: Ask for more accountability.

“Scorecards or OKRs or something like that, asking if you could do scorecarding or some sort of technique so that you can be held accountable for the things you’re being asked to do,” Simon said.

This serves dual purposes: “It lets somebody know what you’re doing,” while adding “a huge amount of transparency, so nobody thinks you’re lazy if they’re not seeing your work product.”

The Perception Problem

Simon shared a revealing story about his first job that illustrates why visibility matters. His boss gauged productivity by stress levels—a metric that worked against Simon’s naturally calm demeanor.

“The way that she gauged whether you were busy or not is how stressed you were,” Simon said. “So I’m pretty relaxed even when I’ve got tons of work—this is what I’m like when I have nothing to do today, this is what I’m like when I have a lot to do today.”

Meanwhile, a stressed colleague was perceived as the busiest team member: “She would be always stressed out, and even if she had like two things to do, she’d be walking down the hall looking wound up… and our boss thought she was always the most, the busiest one on the team.”

Young Simon even experimented with acting stressed: “I did an experiment where I walked down the hall and pretended to be super stressed, and my boss was like, ‘Hey, nice job getting all your work done.'”

“You have to learn your boss’s style,” Simon said. The lesson isn’t to fake stress, but to understand how your boss measures productivity.

Three Scripts for Visibility

Simon offers three specific approaches to create visibility without seeming self-promotional:

Priority Alignment: “Hey, can I sit down with you go through my priority list to make sure I’m focusing my time in the right places?”
Accountability Request: “Hey, can we do scorecarding so that I can be held accountable for you?”
Status Update System: “Hey, can we do status reports so that you know everything?”

“The point is all of those things are telling somebody what you’re doing,” Simon said. “And it does create accountability tools, which is good too.”

By framing visibility as a tool for your boss’s success rather than your own recognition, you transform what could seem self-serving into organizational improvement.