The 7 Deadly Sins of Senior Leadership: How Executives Sabotage Their Lives (and Their Bottom Line)

I’ve sat in three chairs: the CEO’s office with its leather everything and persistent anxiety, the therapist’s chair listening to high-powered executives unravel, and now the consultant’s hot seat where I help leaders avoid the mistakes I made and continue to see repeated like a bad sitcom rerun.

Here’s the thing nobody tells you when you’re climbing the ladder: the view from the top can be spectacular, but it’s also where you’re most likely to step on a rake and smack yourself in the face. After years of being that person, treating that person, and now advising that person, I’ve identified seven patterns that consistently destroy both businesses and the people running them.

1. The Focus Fiasco: Death by a Thousand Priorities
   Bad focus doesn’t just harm your business—it murders it slowly while everyone watches.I once worked with a CEO who had seventeen “top priorities” for the quarter. Seventeen. His team had a running joke: “Everything is important, which means nothing is important.” They weren’t wrong. Even the most charismatic, inspiring leader becomes a source of confusion when their team can’t answer the simple question: “What are we actually doing, and how does my work matter?”

   Here’s the brutal truth: whether you’re chasing 100 initiatives or can’t commit to even one, the result is identical—paralysis. Your talented people show up every day not knowing if they’re moving the needle or just making noise. That’s not just bad strategy; it’s psychological torture.

   The fix: Pick three things. Not seventeen. Three. If everything is on fire, you’re an arsonist, not a firefighter.

2. Burnout vs. Boredom: The Executive Identity Crisis
   This one hits different because nobody talks about it. Burnout gets all the press, but boredom? That’s the silent killer of executive effectiveness.Many senior leaders are creative types who built something from nothing. But businesses, once established, become repetitive. Same meetings, same problems, slightly different PowerPoint templates. You might love what you built, but you’re bored senseless running it.

   Here’s what I see constantly: An executive takes a weekend in Napa, comes back “refreshed,” and by Tuesday afternoon is staring at their calendar wondering if this is just… it. That wine country reset cured their burnout for about 48 hours, but the boredom? Still there. And trust me, your team feels it radiating off you like existential dread.

   I had one client who started every Monday meeting with visible enthusiasm and by Wednesday looked like someone had replaced him with a very expensive, very bored robot. His team’s engagement scores plummeted because apathy trickles down faster than champagne at a New Year’s Eve party.

   The reality check: Time off treats burnout. Only change treats boredom. Sometimes loving your company means knowing when to hand it to someone who’s excited about operational excellence while you go build the next thing.

3. Mission Without Margin: The Innovator’s Delusion
   We all want to change the world. I get it. I’ve been in rooms where people get tears in their eyes talking about disruption and innovation. Beautiful stuff. Know what’s not beautiful? Bankruptcy.If your core product isn’t making actual money—not projected money, not theoretical money, not “if we just get Series C” money—you cannot innovation your way out of negative cash flow. I’ve watched leaders treat funding rounds like they’re playing Monopoly, mortgaging properties to buy Boardwalk, forgetting that unlike Monopoly, you can’t just flip the board when you lose.

   One founder I worked with had a gorgeous mission statement and burn rate that would make a SpaceX rocket jealous. When I asked about path to profitability, he said, “Once we scale—” I stopped him. “Your core product is your foundation. If the foundation is crumbling, building a second story just means more rubble.”

   The hard truth: Make your first idea work and generate real revenue before funding your tenth idea. Creativity requires capital. Capital requires profit. There’s no hack around this.

4. The Disappearing Act: When Leaders Ghost Their Own Teams
   Nothing—and I mean *nothing*—tanks morale faster than executives who don’t show up to meetings they scheduled.Sure, you’re busy. Sure, you’re important. Sure, you have seventeen (there’s that number again) things happening at once. But when you no-show a 1:1 or roll into your own meeting 20 minutes late scrolling through your phone, here’s what your team hears: “You don’t matter.”

   I’ve sat with countless employees who’ve said variations of: “I spent three hours preparing for that meeting. They canceled via Slack fifteen minutes before. For the third time.” One executive told me his assistant managed his “meeting amnesia.” His team called it “being professionally ghosted.” Guess which label stuck?

   The wake-up call: Your calendar is a contract. Your presence is currency. If you’re too busy for meetings, you’re too busy to lead. Cancel your subscription to things, not people.

5. Strategy Theater: All Planning, No Playing
   Lord, save me from another leader who wants to “workshop the framework for our KPI alignment session.”Strategic planning is essential. I’m not anti-strategy. I’m anti-strategy-as-procrastination. I’ve watched executive teams spend eight weeks refining metrics for a product they haven’t even launched. They’ve got spreadsheets color-coded by priority, RACI matrices laminated for posterity, and OKRs tracked to the decimal point. What they don’t have is customers, because they never stopped planning long enough to execute.

   One team I consulted for had a Slack channel called #strategy-fatigue. That should’ve been a clue.

   The formula: 10% focused planning, 90% execution. Not 50/50. Not “let’s do one more offsite to align.” Do the work. You can course-correct while running; you can’t steer a parked car.

6. The Humanity Deficit: When Leaders Forget People Aren’t Widgets
   This isn’t about memorizing everyone’s kids’ names or pretending to care about fantasy football. It’s simpler and harder than that.I once asked an employee what was bothering them when they seemed off. “My cat is sick and I’m worried about the vet bill,” they admitted. I knew about their cat’s health crisis before I knew they had kids. Why? Because I asked them how they were doing like I actually wanted to know the answer.

   Compare that to the executive who opens every meeting with: “Let’s dive into the numbers.” No hello. No “how’s everyone doing?” Just straight to the data. His team was productive on paper and hemorrhaging engagement in reality. People aren’t machines you feed numbers into until output appears. They’re humans who work better when they feel seen.

   The two-minute rule: Start every interaction by seeing the person first, the employee second. The ROI on basic human decency is staggering, and you can’t even track it in a spreadsheet (though I’m sure someone’s tried).

7. The AI Trap: When Tools Become Crutches
   I love AI. I use it daily. But I’ve watched it turn smart leaders into glorified prompt engineers who forgot how to think.Here’s the trap: AI can draft your email, summarize your meeting, generate your report, and probably make your coffee if you prompt it right. But it can’t replicate your strategic thinking, your relationship with your team, or your ability to read a room. When leaders use AI as a replacement for human innovation rather than a tool to enable it, they become curators instead of creators.

   I worked with one executive who used AI for everything—meeting notes, emails, even feedback to his direct reports. His team started joking that they could probably replace him with a ChatGPT plugin and a Slack bot. They weren’t entirely wrong.

   The balance: Use tools for the mundane so you can focus on the meaningful. My 50/50 rule: For every hour you gain back through automation, spend 30 minutes on more work and 30 minutes on yourself or human connection. Technology should make you more human, not less.

Leadership isn’t complicated, but it’s hard. The mistakes that tank businesses are usually the same ones that tank the people running them. Stay focused. Stay engaged. Make money before you spend it. Show up. Execute more than you plan. See your people. Use tools wisely.

And if you found yourself in this article? Welcome to the club. I’ve been every one of these mistakes. The good news is they’re all fixable. The better news is you don’t need another strategic planning session to start fixing them.

Just close this article and go talk to your team.​​​​​​​​​​​​​​​​

Written by Erin Pash. Have you read?
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