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JumpCloud Alumni
JumpCloud Alumni

A long time ago in a land far, far away I had this vision of being at the top of the corporate ladder. Because I’m always truthful with you, dear readers, I honestly thought that a person worked hard, got to the top of the heap, and then spent most of their time vacationing. 

And then I grew up. I worked in the trenches at a couple of different jobs. Serially-speaking, I did data entry, I programmed PBX systems, I ran phone cable through drop ceilings, I beta tested modems, I got married, I had kids, and then I opened a tech business where I did all those things (less the married and kids parts) again. You know, the usual. 

The difference was that the second go ‘round with all those task-oriented operations was for myself. And there was the addition of all the business functions to boot. I really enjoyed doing the tech. I enjoyed being the expert and I enjoyed mastering new technologies. 

But as my company grew, I hired people. And over time, I did less of the day-to-day tech, but didn’t eliminate that aspect completely. I lacked the time, the financial resources, and marketing knowledge to grow my white glove consulting business into a large MSP, so I maintained it at a smaller scale with a few team members. That was ok with me. Until it wasn’t. Things happened, life changed, and I was once again thrown into the day-to-day tech support functions as well as still handling the business side of the business. 

This time, though, I didn’t enjoy the hands-on part nearly as much as I had when I started out. While I wasn’t living my younger self’s illusion of non-stop beach vacations, I realized I preferred the management part of my business over the tech part of my business. Maybe it was that I had been away from tech and fell behind. Maybe it was that I just really enjoyed business management itself. 

No idea. What I did know was that owning this particular business was no longer satisfying for me.


To Management or Not To Management

Today I’m basically working at the bottom of the proverbial ladder. And I like it. There’s little to no stress. I get to do my work without being micromanaged because my leadership team believes we are all capable and responsible adults who have good ethics and produce quality work that nets us the right results. I get the opportunity to do lots of “odd jobs” as well. This is great (for me) because it keeps me from getting bored doing one thing over and over again. 

But when I think about where I could (or would) go from here, I wonder what a “next step” would look like. I know many of you think about this as well. 

Companies will, typically, have a prescribed path for moving upwards — or at least forward — in tech. We’ve all seen the job postings and we all pretty much know the promotion paths and how to go about reaching a management level position.

But is that the goal? Does everyone jockey for that one management spot? Does everyone even want to make that move up? And what does it say about you if you don’t want to move into management? 

I don’t know the answer to any of these questions, of course. So while I’m writing this for your consumption, of course, I’m also writing it selfishly; as a way to suss out the things to consider when setting career goals.

Show Me The Money!

Experienced IT Admins are — generally speaking — paid pretty well. If you’re being paid poorly, you probably should consider job hunting. Your skills are in demand and if you’re any good you should be getting paid your worth. 

When I was doing the job search dance, one of the things that surprised me was that management jobs weren’t always being paid at a higher rate than the people they were managing. 

If you are looking for a move out of tech and into management I, obviously, don’t advocate taking a salary cut to get the promotion. That would be ridiculous. But sometimes a lateral salary — for a very defined and agreed-upon period of time — might work for you. It really depends on how much you want to pursue the career path.

Out of Day-to-Day Tech

Yep. I said it. I know that some management positions are still hands-on. That’s the best of both worlds, for sure. But today I’m not talking about those positions. I’m talking about leaving the intricacies of managing systems behind in order to move into management. 

It’s a big decision. 

Because if you love the tech part, the sad reality is that the longer you’re away from the day to day, the more you forget. It’s simply a use it or lose it kind of proposition. If you are cool with leaving shell scripting behind, then a shift in your path won’t leave you pining for the good ol’ days. If you really want to keep your skills sharp, it might not be the right time. Yet.

Time Management

Another thing that will change with a promotion out of an engineering-type of job, is your time. 

If your company is doing a good job of making everyone feel valued, you will move into leadership in a way that feels like a natural move. 

What might not feel natural is the time management transition. Your work will no longer be influenced by how many tickets are in the queue anymore. You will be managing the ticketing process rather than ticketing system users. It’s a big switch from micro to macro time management. Your time as a manager is more fluid, you need to be more flexible, and your thinking needs to be more strategic than tactical. 

Managing People Not Systems

Not only are you going to have to look at time differently, you’ll have to look at people differently. 

Your role might include more than simply managing others’ workloads — it might include teaching or mentoring your team.

You won’t be chatting across the desk partition, asking for a hand with a powershell command from someone with a complementary skillset anymore. Now you’ll be dealing with your people, which means: 

  • Regular 1:1 meetings 
  • Mentoring your team to help them grow in their careers 
  • Performing periodic reviews of their progress 
  • Recognizing when someone is struggling and offering an ear 
  • (Probably) multiple team meetings each week 
  • Assigning work (or facilitating the process of getting work assigned); and, 
  • Creating programs that further the mission of your department 

And you’ll be responsible for hiring and firing. 

You’ll have to manage all of that along with having the time to meet for your own 1:1 with your manager, departmental meetings, project leadership, and other assorted time and people managing tasks.

If you have discovered that you like working with people and you like helping people succeed, a promotion like this might be just the right career move for you.

Letting Go and Trusting

Good bosses have teams that meet KPIs. Great bosses trust that their team will reach (and exceed) goals and make great stuff. Amazing bosses will have your back. Which kind of boss will you choose to be?

Some have let me know that I can be a bit, shall we say, controlling. Maybe, maybe not. But, as a boss I hired people who had amazing work ethics and who cared about the quality of their work and the clients’ success as much as I did. I felt comfortable letting go and letting them work their magic with as few check-ins as possible. I feel great that in all my time managing people I only had one person who was a bust. One employee left me for a career change, telling me I was the best boss he’d ever had. He was an amazing employee and I felt fortunate to have helped prepare him for that career change. 

If you want to be amazing, you’re going to have to trust your team. Micromanaging their efforts is no way to gain trust. Your team has been hired because they have the requisite skills to do a job. Presumably, you’ve been hired (or promoted), even if you’re still learning and growing, for your skills too. 

You’re Growing Too

Whether or not you choose to pursue or accept a promotion, remember: it’s not just a promotion. It’s really a job change. It will be a new “career” to you. You’ll be starting - sort of - at the bottom again. Know what’s important (people over process) and keep an open mind. Be willing to learn from those above you and from those who work for you. 

And if you choose to not take a promotion, to remain an Independent Contributor, it’s important for you to understand that even though you aren’t moving up the ladder you are still absolutely  engaged in personal and professional development. While progress into management will be met with more money, you will still get raises as an IC - with a caveat. At some point, you will likely hit a salary ceiling and that will be the time for you to decide whether you stay where you are, take that promotion, or search out another company. 

All of which is okay! Nobody demands that you increase your workload for the sake of increasing your workload. Work is only part of your life…not its entirety.

Whew! That was a LOT. You probably need a cocktail now. When I could imbibe in brown alcohol without a headache, my absolute favorite drink was a Classic Old Fashioned (with rye, not bourbon).

The Recipe

Classic Old Fashioned

1 1/2 oz Rye whiskey

1 Sugar cube 

2 dashes Angostura bitters

Few dashes plain water

Directions: Place sugar cube in old fashioned glass and saturate with bitters, add a dash of plain water. Muddle until dissolved. Fill the glass with ice cubes and add rye. Garnish with cocktail cherry and an orange slice (or orange peel slice)Serve on the rocks; poured over ice.

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