Being a Bad Boss/Leader

What do Steve Jobs, Michael Scott, and 2017 Jordan Ostroff have in common?

Let’s dive in.

Steve Jobs, the legendary founder of Apple, was known for his brilliance and innovation. However, he was also infamous for being a difficult boss, often demanding the impossible and expecting nothing less than perfection.  One of his go-to lines was "this is shit!"  Jobs's abrasive style led to moments of genius but also left a trail of disgruntled employees.

Then there's Michael Scott from The Office, the well-meaning but often clueless boss of Dunder Mifflin’s Scranton branch. Michael’s antics are legendary – from his cringe-worthy “Diversity Day” seminar to his ill-fated attempts at becoming a motivational speaker. His heart is in the right place...sortof, but his execution? Not so much.

And then there was me, Jordan Ostroff in 2017. I cringe now thinking back to some of my early management missteps. While I may not have organized a charity run to cure rabies or faked sadness for attention, I made my fair share of mistakes. 

I will be honest - when The Office first came out, I didn't think it was funny (as I had never worked in an office).  Then after being an Assistant State Attorney I found it funny.  And now...I will admit I subscribe to Peacock...so I have been watching the Superfan Episodes...and wow re-watching The Office now as a seasoned boss, I can weirdly see some Michael Scott traits in my former self. 

So, let’s take a page from Michael Scott’s playbook – but this time, let’s learn from his mistakes. Here are five things Michael Scott does that make him a terrible boss, with references from The Office:

1. He Makes Everything About Himself

Example: Remember when Michael faked sadness over his former boss Ed Truck's death just to get sympathy and attention? Classic Michael. Instead of focusing on his team's grief, he made it all about himself...and then also sort of forced them to grieve...

Lesson: Being a great boss means putting your team first. Focus on their needs, not your own. Ensure your decisions and actions benefit the team rather than seeking personal glory.  And while this sounds like the right thing to do anyway...it's also an easy way to increase productivity.

1) people don't leave jobs due to pay...they leave due to bad bosses AND

2) the more you put them first and help them solve problems the more you achieve as a company.  You only have 168 hours a week (and hopefully 40 or so at work)...you can't scale that.  However you can scale the amount of Jim's, Pam's and even Dwights you have putting in the 40 hours every week.

Okay, okay...Dwight isn't scalable there is only one.

2. Lack of Professionalism

Example: Michael’s inappropriate behavior often leaves his employees in uncomfortable situations. From his inappropriate jokes to his mishandling of sensitive issues like diversity training, Michael often blurs the lines between professionalism and personal conduct.

Lesson: Maintain professionalism in the workplace. Set clear boundaries and ensure a respectful and inclusive environment. Your team looks up to you, so lead by example.  I am not against a curse word here and there...but there's a difference between saying the team needs to get their shit together and calling someone a shitty employee...don't make it personal until you need to and then do so in private.

3. Wasting Time

Example: "Everyone in the conference room now!"  Michael’s impromptu meetings, often without a clear agenda, lead to confusion rather than clarity and are a huge waste of time.  My all time favorite line from him on this is when Jan finds that they have been doing 30 minutes of movies and then he says well the team needs to work harder the rest of the day to make up for the 30 minutes they all wasted watching the movie.

To be honest, there is some research about the benefits of those breaks and the team building...I just think it's funny that he doesn't know that, and instead thinks that giving them less time to work will make them work better.

Lesson: Hold structured meetings with clear objectives (LINK TO OUR NEWSLETTER ON THIS).  Turn needless meetings into quick email check-ups.  Try to maximize the time your team members have to do the work they need to do.  AND make sure your team knows what’s expected of them and encourage open dialogue.

4. Proper Handling of Difficult Conversations

Example: Michael often avoids necessary but uncomfortable conversations. Other times he spills the beans too early.  Remember when he immediately told his branch they were shutting down?  Half the time, his shooting from the hip causes needless issues, the other half of the time his avoidance of the issue exacerbates problems rather than solving them.

Lesson:  Tell people what they need to hear when they need to hear it.  Be honest and direct, and work with your team to find solutions when it involves them.  But it's okay to handle some things yourself and not burden them with it.

Really so much of this boils down to this though -

5. Inconsistent Decision-Making

Example: Michael’s decision-making process is erratic at best. One minute he’s canceling Casual Friday, the next he’s reinstating it because he feels guilty. His inconsistent decisions leave his team unsure of what to expect.

Lesson: Be consistent in your decision-making. Your team needs to trust that you will make fair and predictable decisions. Consistency builds trust and a stable work environment.

Sometimes this is trying something new and scraping it...but if you do that ALL the time...no one will ever really buy into any changes.

As I reflect on these traits, I realize how important it is to recognize and rectify such behaviors. Hopefully, this can help others see these issues in themselves and strive to do the opposite.

Next week, we’ll dive into (NEXT WEEK'S TOPIC). Until then, keep your cape ready and your team focused!

Warm regards,

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