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Who’s the Boss? 5 Things to Ask Yourself Before Making the Leap Into Management

Who’s the Boss? 5 Things to Ask Yourself Before Making the Leap Into Management

We talk a lot about professional development these days—how to develop your speaking or writing skills to make you a better practitioner. But what if you’ve reached a certain point in your career and you feel it’s time for a change?

Do you stay a technologist, or do you make the leap to management? It’s a conversation I’ve had with many people over the years and a question I’ve wrestled with myself. Several years ago, I made the jump. At the time, it was the wrong choice. In the following years, I spoke with many leaders and gathered many thoughts on what makes for a successful and satisfied IT leader. Below are the top five considerations I wish someone had shared with me prior to taking the management path.

How in Love With Technology Are You?

We could debate the best course, but often the person promoted to management is the one who knows the most about their technology. Ironically, once in management, you aren’t as hands-on as you once were. If all you want to do is geek out on tech, I’d urge you to be cautious about moving into management. Talk with your boss and other leaders to understand how much tech will (or won’t) be a part of the new management position.

How “Confident” Are You?

This question is something of a misnomer. What I really mean is how are your soft skills and do you enjoy leveraging them? Once you drop into management, you’ll still need to be able to talk the talk and periodically walk the walk of a technologist, but your ability to communicate will become much more important. The same can be said of writing, presentation, and financial skills. Taking some time to evaluate what you truly enjoy doing and where your skills lie will make for a much more informed decision on whether you should take management plunge.

Do Your Thoughts/Ideals/Morals Align With Your Organization?

While it’s possible to make changes affecting your workplace once you reach management, I’d caution you against thinking you can solve everything wrong with the world and steer your company in a completely different direction. Take the time to look at how your organization treats people. Are other managers satisfied in their roles? Do you generally agree with the direction and leadership of your organization? Depending on the type of person you are, this isn’t a make-or-break question. Regardless of your role, it’s often easier and more effective to row in the same direction as your organization.

How Thick Is Your Skin?

This one is simple: when you lead a team, you’re ultimately responsible for the team’s actions and productivity within the organization. On the surface, this seems like a noble charge, and it is. However, there will be days where people just want to yell at whomever is in charge—you. I work within a fantastic, compassionate organization, and there are still days where “The Buck Stops Here” means I’m going to get earfuls from various corners of the org. It goes with the territory. Are you OK finding yourself in this position? It’s a question you’ll want to consider.

From What Do You Derive Value?

I’m not talking about financial reward of moving into management, although hopefully there’s something of a reward. What I’m talking about is how you motivate yourself, where the sense of accomplishment comes from. Basically, what makes you tick?

For me, this was the biggest adjustment in going from an individual contributor role to management. The reward systems can be very different. As an individual contributor, the feedback is often immediate in that, when you achieve or accomplish a task, there’s immediate satisfaction from completion. Many technologists love this aspect of IT—you’re constantly getting things done, you’re a doer. Depending on the size of your org, when you move into management, you’ll be removed from at least some of the day-to-day “doing.” So, where do the rewards come from?

I’ve had this discussion with leaders of varying sizes of organizations and a couple of themes come to the fore across these chats. Successful and satisfied managers talk about the joy from helping develop people. Being an empathetic person and seeing others succeed can become a powerful replacement for that sense of accomplishment. Having a strategic mindset and seeing your place in a larger puzzle can help ease the loss of the day-to-day tactical achievements.

Is Management Right for Me?

Well, nobody can decide if it’s right for you or not. I’ll share one final thought with you, though. At the start of this piece, I said I was wrong about going into management. That was true. In that role, I wasn’t a great manager, and I voluntarily went back to an engineering role. I’ve since made the jump again, in a situation better suited to me and for an organization who helps to develop my skills and wants to see me succeed as a manager. I have a better idea of what to expect and I’m much happier this time around. Whether you decide to make the leap into management or not, know it’s not a one-way street. Whichever way you decide to go, I hope the thoughts here help you on your journey.

I like sharing my thoughts on the softer side of IT. If you’ve found this article interesting, please check out my other articles The Most Important Skill You’re Not Hiring For and Know Your IT Department Frenemies (aka Why Can’t We Be Friends?).


Scott is a 20-year IT infrastructure professional with a focus on virtualization and scripting. Based in Vermont, Scott has spent time running the gamut from small local firms to some of the largest international corporations. When time allows, he tries to give back to the community that has meant so much to him through his blog, involvement with VMUG and speaking about PowerShell and PowerCLI.