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

Level 12

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 the 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?).

Level 9

Thank you for posting this, I really needed to see this right now. These really are questions you should ask yourself before even considering the idea of moving into management. And some I hadn't really even put much thought into.

Level 12

Thanks medleyp812​! It's not an easy decision and there are a lot of factors that go into making an informed decision, beyond what your pay structure will look like.

As I mentioned above, the hardest part for me (and it still is), is not having my hands in the tech on a day to day. I've had to find other ways to scratch that itch (like writing blogs), and I've found that if I can still have a little bit of tech in my life, I'm ok with that.

Level 14

This has been a huge gripe for me over the past few years.  People assume that being in management is a true illustration of success, and that fragile ego gets damaged so easily in some cases if someone is told that they are not a fit.  The truth is, being in management is a direct trade have to be willing to let go of technical aspects and trade it for the human aspects.  I like to refer to this as trading technical engineering for people engineering.  If you don't have the skill, patience, or desire to put your efforts into building relationships and helping people, then you should recuse yourself and stick with non management roles. 

Thanks for the article. 

Level 9

scott.driver I totally get that. After all, it is the reason most of us got into tech.

Your blogs are fantastic! I hope you're able to continue writing them both to scratch your itch and so we get to read them!

Level 12

You're very kind! You put a giant smile on my face. Thank you very much.

Level 12

You make excellent points! I especially like your analogy of people engineering.

The decision isn't an easy one to make, and it can have hidden landmines. I just hope that I've helped kick the dirt off some of them.

Level 10

I guess I'm lucky in that my company recognizes that there are technical leaders and people leaders. Someone may have great followership because of their technical prowess, but they simply don't have the desire or skills to provide other aspects of people leadership. I can also attest that it can take quite a long time to feel comfortable to completely transition out of the technical role. Someone making that transition needs a lot of coaching and guidance to be successful, but then they will make great leaders who have the respect of the technical people they lead.

One thing that hasn't been mentioned is the challenge of growing out of your team and then being faced with having to provide negative feedback or even disciplinary action to a friend. This can be difficult for both the leader and the team member to find the right tone, attitude and way of delivery to make sure it does not damage the team going forward.

Level 12

I'm considering a leap into management so this is very well timed. Thank you!

Level 12

You are totally right and I even meant to dive into your point. Becoming "the boss" impacts how you interact with the team socially. I never expected that on the first go around! Let's just say for now that having to manage or discipline what were formerly peers, is not for the faint of heart. It takes a little bit of steel and a lot of finesse.

Thanks for highlighting this point. It's a really important one to make note of!

Level 12

I'm happy to have helped! Make sure to check out alang​s response below. They make excellent points that adds to the conversation.


Gotta say, the step to mgmt isn't that bad and for me at least has been better suited to my style.

I'm a generalist that enjoys being very specific for many things, but going to mgmt has meant my skill at being able to see the much larger picture and include business needs along with the geek has meant I can now influence much more.

Overall - a pretty darned good move.

Level 12

Congratulations on the successful move!

Level 14

Made the move several years back.... Here are some observations of how to keep some order in your own universe....

1. Hire and promote smart people.

2. Be a good BS umbrella for your team.

3. Try hard to stay up to date... be ready to fall behind a bit.. it happens.

4. If you manage former co-workers be prepared for the change... sometimes it's easy, most times not so much.

5. It's not about the technology itself. It's about how the technology helps the business.


7. Help your people communicate!

8. Say thanks to your team, you succeed as a manager BECAUSE of them!

9. Find alternate ways to recognize and reward your team.

10. Be true to yourself.

Sometimes sweating the petty things can make for consistent and positive outcomes.

"Five things to ask yourself . . . "

  1. How in love with . . .
  2. How confident . . .
  3. Do your thoughts . . .
  4. How thick . . .
  5. From what do you derive . . .
  6. Is Management for  . . .
Level 14

Meant to comment earlier... Excellent article scott.driver

Sometimes mentors are needed but are lacking.... But in the end the right fit is what matters most.

Level 12

HA! I’ve been waiting for someone to point that out all day!

The last one was meant to be more rhetorical in nature.

Level 12

Thank you George. I appreciate the complement.

Level 13

Thanks for the Article. Tried management once but it wasn't for me. I enjoy the technical bits too much.

Level 13

Good post, thanks. I would like to toss in my 2 cents - it's not an either/or option, it's possible to do both, and become a working manager.

Now I must say there is a cap (or a possible cap at any rate) to that path.  It depends on the organization and what you can finagle, but it is possible.  I once worked with senior VP that was still very technical, to the point of designing his own hardware/software while still leading the team, but he was pretty extraordinary.

I've been able to be both management and technical for more than 20 years.  It's not for everyone, because you get the best and worst of both worlds, but I'm glad I did it and would do it again. The best part of being part of leadership is you can help to steer the ship, that's a great benefit.

I did have to turn down the career limiting (for me) promotion to VP a few times (the org structure was such that I wasn't able to negotiate the both tech and leader option) so I turned it down.  There are people that looked down on me for doing that, but for me it was worth it.  Just know what you want and stick to your guns.

Level 12

That's impressive df112​. I've seen many managers who aren't able to bridge those two roles. As you state, of course it's dependent on the org and the individual, but in my experience I think you're more the exception than the norm. Congratulations on this, it really is a feat that should be celebrated!

I am curious though, when you stepped into that dual role, did you have management experience already? I have found that the skillsets required for individual contributor, vs management are very very different.

Thanks for adding a valuable viewpoint to the discussion!

Level 12

It's not an uncommon feeling and kudos to you for being able to recognize what's important to you!

Level 13

I didn't have a lot of management experience when I started down that path, but I did have some great managers leading up to that, and I watched what they did and tried to duplicate it (and I had some real duds that informed the "don't ever do this" list as well).  Some of the stuff I tried didn't work, so I filtered that out and found things that worked for me.  At first it took some getting used to, but like a lot of things you get better at it over time and I've honestly enjoyed it.

Your list absolutely still applies though.  One of the toughest is when you start managing people that used to be co-workers.  Some of them don't take too kindly to not getting extra favors or special treatment.  Might cost you some friendships, but they probably weren't really friends anyway.

Level 12

Great stuff! Thanks again df112​!

Level 16

Thanks for the write up. For me, I will probably choose to remain an engineer. After years of being in Architectural / Engineering rolls I'm ready again to get back into the field and be more active than my desk job allows.

Level 12

Self-awareness is a critical skill to have when going through this process!


Thanks for the article.

I'm happy to be the picker of nits for you, Scott.

Level 12

Thanks for reading  🙂

Level 10

Great article Scott, I have made the jump previously and although overall I enjoyed it, the change in the way you have to work from being a techie to being a manager is pretty big. Becoming a leader and a manager of people is different from turning the nerd knobs all-day. Silly things that you never considered before like annual leave planning etc all take up time. If you are going into management as a "badge of honor" then that's the wrong reason. Going into to it to get a better appreciation of how all the cogs turn in a business is a better way to approach it I think.

Like George's list of points above, they all resonate, BS umbrella being very prominent!


Level 12

thanks for the post

Level 12

Thanks for reading!

Level 12

Thanks Ian! Your complement means a lot to me.

It's truly amazing how much time can be taken up by pushing paper. It's a necessary evil that goes with the territory, so it's something that also needs considering.

Thanks again Ian!

Level 14

22 years ago I had progressed as far up the techie path that I could in the company I worked for.  I would have to go into management to get any more pay rises (I was already two pay grades above my manager and had a better company car).  I refused so was forced out.  I went contracting for 20 years as a techie.  Now, thanks to the UK Tax man, I'm back in a permie role as a SysAdmin and doing my best to be a BOFH (Data Centre » BOFH • The Register ).  Still not management and still enjoying being a techie.  For me, definately the right choice.

Level 12

I'm glad that you were able to find success and fulfillment while sticking to your own path. Well done!

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