That's the question one of my employees asked my then roommate who attended the Art Institutes, where I was just getting started as a Technology Support Supervisor in early 2001. I had just been promoted from Apple Technician (a role I got while still attending the college) to being the head of the IT department. I may have been an exceptional Macintosh technician but that clearly didn't translate to being an exceptional leader.

I don't recall what my roommate's response was, but upon hearing this I was surprised to find that my employees thought of me as Darth Vader when what I was going for was Steve Jobs. Not Steve 2.0 (1997–2011) but the original, brash, arrogant wunderkind of the early 1980s. You see, I didn't have any role model for how to be a young technology leader so I read books like Steve Jobs: The Journey Is the Reward and Apple: The Inside Story of Intrigue, Egomania, and Business Blunders.

Looking back, obviously it was a bad idea to model my leadership style on stories of egomania and business blunders, but I was young and naive. I may have been very smart about computers, but I was not very smart about people. Unfortunately, my new role was less about leveraging technology and more about having people skills — and I was in way over my head!

No Instruction Manual

Nostalgia is an interesting thing. In some cases we view the past through rose-colored glasses and at other times we tend to be overly critical of our former selves. I am usually more of a citric because I often wish I would have handled things differently (or better) than I did. Hindsight is 20/20 as they say. Cutting myself a little slack, I would say that I was trying to do my best with the limited tools available to me.

First off, I was too young to be in the role I was in. I started as a professional manager at age 20 and I lacked any kind of real world experience that would have instilled some empathy or compassion for my staff. It's hard to figuratively walk a mile in someone else's shoes when you've barely walked down the road in your own. Second, I didn't have any positive role models or mentors around me that could demonstrate what a good leader was supposed to do. I didn't get a lot of support from other managers and my inspiration for being a successful young leader was Steve Jobs circa 1983, the guy that got fired from his own company for being a jerk.

Sure, I took the requisite basics of supervision training course but that was really more about the tactical aspects of management. How to interview new employees, how to give them performance reviews, and how to supervise them around the technical aspects of the job. All of these are important skills, but they don't really get to the heart of what it means to lead people.

Learning the Hard Way

When you don't have a mentor and you don't have a solid roadmap to follow what do you do? Figure it out the hard way, of course! What that looked like for me was a series of leadership challenges that had profound consequences for my career. Here's just a few of the pitfalls I experienced on my path to becoming a better leader.

• Hiding behind a persona based on toxic role models (see above) rather than being my authentic self.
• Failure to build a positive working relationship with cross-department teams, undermining my effectiveness as a team leader.
• Failure to delegate appropriately and taking on all tasks myself rather than trust my employees to do a good job.
• Caring more about my own advancement than developing and supporting my direct reports.
• A fear of failure that lead to burnout, stress-related health issues, and divorce.

I don't think these are particularly unique to my leadership journey. I would imagine that most leaders struggled in these areas and others. Leadership growth for a lot of us looks a lot like trial and error, wandering around with a blindfold on and trying not to step on rakes.

Becoming Authentic

I'm no Steve Jobs, but one thing we do have in common is spending a decade in the career wilderness. Like Steve leaving Apple in 1985, I had to leave the Art Institutes and get a fresh start somewhere new. This lead me to the Cincinnati area and after several years of struggling, I started to improve as a leader. I didn't do this alone and it didn't happen overnight.

First, I was lucky enough to be surrounded by people who demonstrated what good leadership is. Second, I had to let go of some control and start to trust my employees for a change. Third, I hired employees who were better than I was and supported the work they were doing. Finally, I learned how to be a manager who set themselves apart from their team without trying to be someone I wasn't.

That last one was a major unlock for me. I'm not sure if it was some form of imposter syndrome but I recognized that I went out of my way to pretend I was someone I wasn't at the office. In real life I'm a warm, fun, and relatively easy going guy but at work I pretended to be the exact opposite. I thought if I was kind I'd appear weak. I thought if I was easy going that my team would take advantage of me. I thought if my employees didn't fear me, they wouldn't perform. I couldn't have been more wrong.

As luck would have it, I eventually ended up back to work with the Art Institutes several years later and had the opportunity to put my new leadership principles to work. It was a challenging environment for sure, but now I was ready to lead people the right way and my team accomplished some amazing things.

Several years later, when I started working at Eastern Gateway Community College, I made the conscious effort to be my authentic self from the jump. Instead of cosplaying as an executive director in a suit and tie, I walked into my first meeting with my brand new team wearing my red Vans and carrying my 'Pod Save America' coffee mug. I smiled and laughed and made the effort to get to know each of my new employees and more importantly I let them get to know me. Not this fake "manager guy" but actually me. We talked about music, movies, video games, politics, my kids, their families, and we developed a real relationship based on mutual understanding and care for each others' wellbeing.

This wasn't about being chummy with my employees or wanting them to like me as a 'cool boss'. I still maintained the required professional distance as a manager. But what this was about was developing shared goals, supporting their professional journey, and building a team where every employee cared about each other and strived to do their best work.

This authenticity had a transformative effect that kept paying off downstream. For example, when I had to give an employee critical feedback they understood that it came from a good place. We had already established trust, shared goals, and they were safe in the knowledge that I wanted them to do their best work. That allowed me to provide honest feedback and it allowed them to receive that feedback in a constructive way.

This is totally based on anecdotal data but I think my team was the highest performing one in the whole organization. Interestingly enough, we experienced the least amount of turn-over through out the many years we were a team. It's obvious to me that the success of my department was due to hiring great people, trusting them to do their job well, and building an authentic bond with them by being myself — warm, caring, and mission driven.

The Missing Manual

It took more than a decade for me to finally understand how to effectively lead people. I wish there was an actual manual on how to do this that could have shortened my learning curve from years to months. This is the reason why I created my latest course — Modern IT Leadership: How to Build Strategy, Align Teams, and Execute in Real Organizations.

I took all of these lessons that I had to learn the hard way and compiled them into a roughly ten-hour self-paced course that new managers can use to fast-track themselves to becoming the leader they were born to be. This course includes case studies, frameworks, and assignments that you can do within your own organization to begin leading more effectively right away.

On side note. I noticed the other day that LinkedIn just published their annual list of in-demand skills for 2026 and leading people was ranked as #1. As a result, I'm doing a special offer right now discounting the course to $14.99 for a limited time. You can view the full course outline and access the first few lessons in the course for free. If you find value there, then simply use the coupon code LINKEDINSKILLS at checkout to claim this special discount.

Special offer: Enroll in my new course — Modern IT Leadership: How to Build Strategy, Align Teams, and Execute in Real Organizations for only $14.99 using coupon code LINKEDINSKILLS at checkout.

© 2026 Drew Smith — Automata Technology Services

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