4 Shocking Ways Leaders Bring Their Own Downfall

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A c-suite executive client gave me a ring from a payphone in San Francisco to fulminate on mistakes that destroy executive careers. 

Clearly, he knows his audience.

During our chinwag, we couldn’t help but write today’s edition of Execs and the City. 

Funnily, the lion’s share of the conversation centered around: 

“How damn stupid are executives lately? Why so many bonehead mistakes—and why are they repeated so frequently? What even is an executive? Damn whippersnappers and bitchy millennials, they’re entitled and haven’t earned it. BAH Humbug.”

I think it went exactly like that—or I’m paraphrasing. You be the judge.

And—yes, sometimes I, Jacob of all Jacobs, am a pretentious know-it-all barking about how smart I am and scoffing at the dumb things faker-ass executives do. But it fits the brand, so give me a break. 

Anyway, let’s talk about a handful of career suicide mistakes that other executives are guilty of committing (and obviously not you, you beautiful you).

#1 Prematurely Inflating Your Executive Presence

LinkedIn influencers and early-stage companies would have you believe anyone can become an executive. Seemingly overnight. 

You deserve a platform and must become a media company to elevate your personal brand. You’re told you must do it—even if most of your “thought leadership” is rudimentary and repetitive with no value added. 

Or noisy dribbles. 

While there are notable advantages to self-promotion—and I’m caught red-handed—positioning your expertise commensurate with your experience (or slightly raised) is vital. 

Stop over-inflating your self-worth if you can’t back it up. You impress the wrong audience and turn off those you aspire to be.

The problem with standing on a soap box you didn’t earn, elevated roles, your sense of entitlement to get them, and how Americans, in general, tend to be so obsessed with climbing the ladder—is that when everyone is saying they are a leader—it bastardizes the meaning of leader. 

You devalue what it means to be an executive.

I can see this mistake so clearly—because I did this to clamber up the ladder myself. And boy, am I embarrassed about how much of an asshat I’ve been to my former colleagues, bosses, and mentors. 

My executive acceleration wasn’t about making more money but getting more respect and jostling for a new social tier. Executives are highly respected, no? The world isn’t driven by greed; it’s driven by envy.  

With a baseline understanding that 90%+ percent of people claiming to be executives are not who they purport to be, you can understand why so many bonehead executive mistakes are frequently repeated.

#2 Mismatched Expectations

Too often, executive leaders hop into a new role on the wrong foot. Or, more likely, they were never true executive leaders after all. 

Your first mistake may have been during your interviews’ hopelessly optimistic wooing period. Or you naively accelerated your negotiation through lackluster due diligence and failed to challenge or set more obtainable expectations. 

Some executives master getting the role and can set aligned expectations with other senior leaders but fail to manage those expectations for their teams. 

All mismatched expectations cascade into confusion, misalignment, and your ultimate demise because your head is on the block. Worse, it’s your fault, and you probably did it to yourself. 

One of the most common mismatches on my desk is regarding the nuances between a coach and a player. 

Any executive worth their salt should raise a crimson flag if somebody persuades them into a player/coach role. You might as well pour your own concrete shoes for your executive career.

Employers and leaders need to learn the difference between strategy and tactics. Everyone loves the word strategy but almost always defaults to their tactics-based comfort zone when shit hits the fan. 

We all share the blame for this communication breakdown.

Companies say:

“We want a strategic leader to build everything from scratch. You’ll grow into the executive role later.” 


“We need to hand all of this off to someone with a lot of experience because we don’t know what we’re doing—we don’t have time to find OR handhold an up-and-comer that would be a better fit—AND we can’t afford your expertise, but we promise we’ll take care of you later. Deal?”

You may fail to push back because you don’t know the difference between strategy and tactics, are uncomfortable pushing back, or are so desperate for the work or title you’ll say anything to appease the oxymoron and bunko-garbage deal presented to you. 

So what do we do?

Executives say:

“I’m a strategic leader excited to build everything from scratch…”


“I’m not a strategic leader, I don’t have the courage or brains to tell you that you’re wrong, but I need this paycheck.” 

Sometimes leaders will strive to outwork the problem of mismatched expectations. These superhero try-hards shoulder the damn world because, deep down, we know we like it. 

40 hours quickly descend to 80 plus. Burnout transpires. Frustration toward the team festers as exhaustion begins to rear its teeth. “Why doesn’t anyone recognize how hard I’m working?”

You’ve seen this play out enough to know what comes next. 

Executives begin to micromanage. Then demotivated teams and decreased productivity erode trust in and from leadership. Bosses lose faith, fail to delegate tasks to their useless teammates—and further overburden themselves.   

If this is happening to you, what will you etch on your tombstone? I mean, LinkedIn?

#3 Forced Playbooks

I have a love/hate relationship with playbooks and templates. 

In grammar school, I treasured that all of my textbooks had answers in the back. It made school a breeze. I never understood why some kids had homework when the powers that be gave us all cheat codes to win the honor roll. 

Fast-forward to adulthood, where the cheat code generation is unlocked for everyone. We no longer need maps. Or libraries. Or schools. Or rights!

ChatGPT will someday emulate my cynical snark, and all my videos will be built with generative AI, perfected eyeball tracking, and a velvety smooth text-to-voice narration.    

Now take a moment to recognize how damn lazy we are. 

We are so used to everything coming easily that when faced with a new challenge, we have a proclivity to cheat. 

  • Why build a new strategy when I can copy how Google did it? 
  • Why think for me when I can ask someone else on Slack?
  • Why differentiate when I can be a zombie robot clone too? 

Getting the answers so effortlessly steals people from their ability to think on their own and work through hard challenges. 

But aren’t strong executives supposed to be admired for leading teams through tough times? Am I naive to value originality? Creativity? 

If you reinstate the same playbook that worked for a previous company—or copy and paste a strategy from a competitor—you lose. You’re behind the times, and the rate of modern innovation will kick your ass to the curb. 

Now more than ever, executives need to bring new perspectives. There is no shortcut to a fulfilling career, and if you follow the path created by another—by definition, you’re not a leader. You are a follower. 

#4 Joining An Incubus (Or Succubus) Startup

Today’s last point puts a big shit-eating grin on my face. Mainly because I get to display how depraved my mind is—after all, I did grow up as trailer trash watching South Park and playing Grand Theft Auto. What did you expect from me? 

I hope the following isn’t triggering. 

Yes, I dare to compare some (many) startups to shapeshifting demons who delight in the corruption of mortals through sexual temptation. 

In a world where tens of thousands of fresh Metavites, Amazonians, Microsofties, and other talented tech folk have entered the market—a bloodsucking opportunistic startup parasite you’ve never heard of appears to save the day.

Toxic leech (and usually bro-tech) startups are here to pick the bones of a shattered marketplace. They pray on great talent—and will eviscerate your once promising executive career. 

Don’t fall victim to joining a startup to ride a unicorn into battle and laugh at the Plebeians who aren’t sitting on a fat stack of coin in retirement. 

That will not be you. Instead, you’re more likely to be referenced by Pink Floyd here.

Startups have a 0.00006% shot at becoming a unicorn.

More often than not, a bad startup decision will gnaw your career to the bone while you wait for something better. In the meantime, you’re bent over while your market value diminishes, negotiation leverage falters, and the likelihood of you trying again with another startup increases. 

Now you spiral into mediocrity—or worse.

Before I get lit up with nasty comments—I love startups! Many startups are groovy for ambitious folks that can accelerate their experience and learning. When aligned, you can earn an MBA in 90 days.

Startups serve such an essential role in our economy and drive innovation forward. I owe much of my accelerated learning primarily to startups. 

But for seasoned executives? Is it worth it? 

In the “what have you done for me lately” world that we live in, can you afford to string together 2-3 lower-paying 18-month ‘executive’ tenures on a gamble that your options are worth more than funny money? 

Can your reputation—or mental state—sustain a losing streak? 

I guess if it doesn’t work out, you can always become a consultant or career coach on LinkedIn.

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