One millennial’s struggle moving into management

7 min read

I first stepped into a leadership role at the age of 28. At that time, nobody I was close with had really managed a team before. Like many people, I saw this opportunity as the obvious next step, a move in the right direction — up. It would be a great opportunity for me to build a skill set I didn’t have. My career up to that point had been focused on getting computers to do what I wanted them to do, in an efficient way. I was good at it too. Every job I had, I would collect all of the boring work I was expected to do and I would automate it so that a computer would do it for me. This made my productivity and effectiveness skyrocket, which is what probably led to this promotion in the first place. I remember someone early in my career warning me though, “with computers you tell them what to do once, and they do it, exactly as you told it. People, not so much…”. What I want to talk about today are some of the unexpected challenges I ran into moving away from leveraging computers and into leveraging people. By no means do I regret it, and I’m not telling you to dissuade you from moving into management, but I want to share my story to help prepare others for their journey ahead.

It’s Lonely at the Top

Early in my career I never bothered to stick around a company for more than a year. That meant that people came and went, without the opportunity to really get to know them. My whole career I was always the youngest in every team I worked with. By a lot. That meant that we didn’t have a lot in common. I have fond memories of all of my coworkers, but I never really crossed paths with people that I ended up going out with after work — they were workplace proximity associates.

After being promoted into a leadership position, and sticking around a company for long enough to form some bonds, I realized that my relationship to my coworkers would need to remain professional. Wherein before I never knew anyone well enough to see after hours, in my new position it wasn’t really something I could do even if I wanted to. I promised myself I would be a non-traditional leader — someone who didn’t care about what the typical picture of a manager was. But that doesn’t change the fact that it’s easy to form the appearance of favoritism. Having lunch with the same team member every day, grabbing a beer with someone after work, casually texting or messaging people outside of work… Yikes! Those would all have significant consequences at the end of the day.

In an organization, the pool of people that you can be friends with is typically your group of peers — the people on the same level in the hierarchy as you. Most hierarchies shrink near the top, which means the higher up you get, the less people you have to draw on. This can be challenging, when you run into a tough situation that you just want to vent about, when you want to talk through a problem with someone else.

You’re involved in everything

I remember a time when someone would bring me a problem and I would say “oooooo that’s a tough one, you should talk to the boss about that”. All of the hard stuff gets kicked up to management. That means that there’s a filter. Problems float upwards in an organization. Hopefully there’s a filter, so that you aren’t dealing with every problem in the organization. If there is, you reduce the over all number, but that filter only eliminates the easy stuff. It’s the hard stuff that gets through. If your team has a lot of problems, or aren’t used to solving problems on their own, then day after day, hour after hour, you’re going to be working on solving really hard problems. In Star Trek they have a test called the Kobyashi Maru — it’s impossible to win, and it’s used to assess your decision making when faced with a no-win scenario. It’s not uncommon for leadership to be filled with these scenarios, and it can get taxing on your brain, and your confidence. When you’re always focused on just getting by, it can feel like you’re never doing a really good job, unless you have the perspective and headspace to step back and see the big picture.

Your brain never stops

This is a by product of the above challenge. Gone are the days of performing a task. With your new found promotion you don’t perform tasks, you solve problems. Sounds exciting right?! Problem after problem, day after day. Have you ever had a really intense debate with someone where you were constantly challenged and had to keep thinking of ways to get your point across? Or have you ever played a challenging game like chess with an opponent worth your time? Remember in school where you had 5 papers, 3 exams and a presentation all due in the same week? That’s what leadership is — all the time. When you think of manual labor it’s clear to understand the soreness and pain that comes from working with your hands, standing, lifting and moving all day. Your muscle ache, your joints hurt. Everybody can empathize with that. Your brain is a muscle too, and if you spend all day every day flexing a single muscle, that things going to get sore. It’s going to ache. It’s going to fatigue. Take care of your brain. Don’t strain it, recognize when it’s tired and give it a break.

You only have so much emotional energy

Emotional intelligence is becoming an increasingly popular skill for leaders. That’s because to be a good leader in the 21st century, you need to care. You need to empathize with your team. You need to care about the customer. You need to take people’s feelings into account when making decisions. The challenge is that you need to save up your emotional energy for your home life. Your family deserves to see you at your best, and if you’ve tapped out your emotional energy for the day at work, you may not come home in the right frame of mind to give your family the support, caring and love that they need. This can be very painful for your loved ones, and it’s something I think leaders will struggle with as we continue to learn the value of emotional intelligence as a skill for successful leaders. If public speaking is something that you aren’t good at but need to do as a leader, you can learn to give speeches and exhaust that part of you at work with little/no impact on your family. If you’ve given all of the fucks you have at work, and have none when you come at home at the end of the day, you’re going to be grumpy, short tempered, and unable to empathize with your loved ones.

Is it all doom and gloom?

Of course not. The best way to combat these challenges is to surround yourself with people that care about you. People that you can be honest with. People that will listen to you. But even with these people in your life, your problems won’t magically go away, you need to talk through them. Share your challenges. Don’t feel badly about complaining about your fancy new role, with all of the extra money and perks it brings. Those things don’t matter if you aren’t happy. Success doesn’t only bring joy and happiness, it brings new challenges and hardships, and it’s ok to talk about those things

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