The Startup
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The Startup

Be A Bad Boss

Becoming a bad boss might be the best move for your career.

The Conference Room

We’ve all been there. Your boss walks into the room, and you’re ready to quit. You swore to yourself heading into the office that if your boss brought up that thing just one more time you would storm out and quit on the spot. Not being seen or heard; Feeling like the company owes you for all the hard work that you’ve put in. Why is it that so many of us have experience working under bad bosses? I’ve been a bad boss myself. I’ve driven my teams to frustration and confusion, constantly putting everyone under pressure they were never meant to carry. One of the most perplexing things to me as the President & CEO of The Penn Group is the ability for one person to completely turn everyone’s world upside down. I constantly fret about the prospect of losing my team that I rely on. In my career I’ve been on the wrong side of both sides of the ball, and my recommendation for you is to be a bad boss.

The Paradox of Leadership

As a leader, it can be easy to turn into a draconian boss that demands respect by way of position. After all, you’re the boss. Who should be able to challenge you anyway? Maybe that isn’t you. Maybe you’re the kind of leader that doesn’t want to hurt anyone’s feelings. Maybe you want everyone to like you. It would be easier not to have the conversation with Robert who chews his nails in front of everyone and makes them uncomfortable. It would be easier.

Being a boss is easy. Being a leader is hard.

Being a leader, in fact, it is one of the toughest jobs in the world. My leadership tends to lean towards the latter of the two examples. I tend to be a leader who exercises restraint in order to ensure the preservation of people, feelings, and ego. By ego I mean, my ego. I want people to like me. I want to be the best leader in the world. While trying to be the best leader, I ignored situations that should have been addressed. By trying to preserve relationships, I actually further damaged my own creditability with my own people by not leading through the challenge. I call this self-deceit the “paradox of leadership”.

The Paradox of leadership: Our natural inclination is to avoid, mitigate, and transfer in order to protect emotions, ego, and perception. With these efforts, we actually further damage the things we are trying to protect. We might ignore the fact that Stephanie didn’t show up to a meeting to protect her feelings. In reality, the rest of the team’s morale was damaged because they showed up on time, and their time was not respected. From my team, what I get is a product of what I encourage and what I tolerate. If I don’t address for fear of hurting, I might hurt everyone. Have the conversation. Get into their business. Otherwise, you might be going out of business yourself.

When You’re A Great Leader You’re a Bad Boss

In my career, the happiest I’ve ever been working for someone else was when I had the trust and authority to do what I thought was best for the organization in my particular subject area. The most positive work environments I’ve worked in shared these characteristics. This highlights an interesting paradox. In contrast, the most frustrated I’ve ever been in an organization has been when I was not trusted or given the authority to carry out my job. Of particular frustration is when a boss tended to micromanage every move. This is typical behavior of a boss. In most situations, a boss is accountable to goals and metrics, and they are measured on how they meet those goals. A boss will typically get angry is something isn’t done, and it can be expected that you will be held accountable. That is a good boss.

What if instead of being a great boss, you become a great leader? What is the difference? Instead of managing goals, you inspire people. Instead of micromanaging the project through the end, you empower your team to get goals completed on time. Instead of angrily dismissing pushback, you embrace feedback from your team. The biggest transformation for the productivity of my teams came when I embraced being a leader, opposed to a boss. Being a great leader makes you a bad boss. When you’re a leader, you may not hit the metrics. When you’re a leader you’re not judged by the percentage of your output, but you’re measured by the value of your team. Leaders fight fights; bosses diminish conflict. Leaders embrace potential; bosses diminish hope.

Become a bad boss. Be a great leader.

Austin Harman is the President & CEO of The Penn Group. He currently holds the coveted CISSP certification, in conjunction with the CCSP, CAP, and Security+ certifications from ISC2 and CompTIA respectively. He resides in Columbus, Ohio.



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Austin Harman, CISSP

An experienced cybersecurity leader serving as the President & CEO of The Penn Group. I hold the CISSP, CCSP, CAP, and Security+ certifications.