Confessions of an IT Director

A New Boss

There isn’t much in the professional world that is more anxiety-producing than getting a new boss. This can be when you switch jobs, or someone is promoted above you, or a reporting relationship change, or a myriad of other situations where your direct (or indirect) supervisor changes. I’ve been on both sides of that equation, and it makes my stomach turn thinking about it. I’ve also watched it happen around me, and rarely, if ever, does it go smoothly.

I believe there is this pressure to make changes as the incoming boss. Not specifically because changes need to be made, but changes are the barometer for which an organization can measure your performance as the incoming boss, right? Because if things were going smoothly and running without issue, why bring in a new boss?

This is especially true in the IT world. Because there is… ambiguity…  about what we (as IT folk) do, very often the (incorrect) assumption is that we’re not doing anything. You’ve heard the metaphors… IT is like the plumber.. You don’t think about them until the toilet is clogged. I like to have privacy screens on my monitors, not because I am doing anything nefarious, but because with my level of access as the IT Director, I’m very often dealing with things that are confidential in nature, or have access to data that not everyone has access to. Yet, there are fewer things that produce more buzz than the dude who’s screen you can’t see. “What’s he hiding?” “He’s watching Netflix” “I saw him streaming video” – all of which have been said to me from bosses who have fielded complaints. Point is, because they don’t know what I’m doing, they assume I’m not doing anything…. 

I digress. 

What I’ve found in my career is that it is just as anxiety inducing to BE the new boss, as it is to GET a new boss. It’s made me think about what kind of boss I want to be. Here are a few I’ve encountered along my way: 

“Great boss, horrible manager” This boss was extremely flexible to me, giving me full autonomy to get done what I thought needed to be done. When executives questioned my actions or methods or proposals, this boss backed me unequivocally. Did I need to leave early? Check. No problem. “Can I work from home today?” Check. No problem. “We need to buy this <insert IT initiative here> because it improves such and such.” Check. They agreed and took it to the executives. This boss put full trust in his team and let them use their skill set. 

Admittedly, personally, I felt that I did my best work under this style of leadership. However, there’s a sharp decline to this style, one that I didn’t think about. I mean, who doesn’t want a boss that leaves you alone and lets you do whatever you want to do? The main issues present themselves when management begins to notice that the boss isn’t really doing anything, but that his (or her) reports are actually running the show. When asked a question, this boss would always respond with, “let me check with (insert me here) and I’ll get back to you”. Soon, management questions what it is that the boss is actually doing, and eventually the cost benefit of having that boss there becomes more than what management feels the boss is bringing to the table. The boss is let go, and another is brought in to “reign in” the department. The “great boss, horrible manager” never really managed. No direction on projects, no discipline in meeting goals, no performance indicators (I don’t think I ever got a performance review under this type of boss), and ultimately, no accountability. This boss either takes the fall for a department, or blames the shortcoming on members of the department (I’ve been there, too). Ironically, if this type of boss is able to effectively dodge a bullet for a shortcoming, it usually doesn’t last for long, as the pattern repeats itself even with the next person up. The boss’ inability to manage comes back to bite them, and people are burned along the way.

“What were you doing between 11:17 and 11:34am?” Also known as the extreme micromanager. I started with the boss type that I did the best under, but now I give you the one I performed the worst under. Every movement is scrutinized under a fine-tooth comb. I had a boss who asked for daily reports of my activities, with to-the-minute accounts of my time. This was for a MSP (or Managed Service Provider). I understood that time spent on client activities was billable to the company we were providing service to, but this went above and beyond. GPS tracking on my work phone to track travel time between clients, reporting of bathroom breaks, utilizing CCTV systems we supported to verify I was where I needed to be, doing what I was supposed to be doing, when I was supposed to be doing it. Checking connection logs to verify that the IP addresses matched where I was supposed to be connecting from. 

This type of management was demoralizing, suffocating, and just all around awful to be around. A polar opposite of the first type I mentioned, this type of boss over managed, and was not a great boss. 

“I want it all, and I want it now” Queen is stuck in my head. This is the boss who I feel I’ve run into the most in my career in IT. The boss who is somewhere in between the other’s I’ve mentioned, in some ways. Usually this is when IT reports to someone who is not in IT, and so they don’t have a clear understanding of the requirements set forth. The IT Director (me) makes a proposal, and it’s like a merger negotiation, we go back and forth for weeks. When this boss finally accepts and signs off on the proposal, the expectation is that said project will be done, now. “I want it done by…” Or, “When are you going to be done with that thing we signed off on last week”

There are more, but I won’t go too much into them.

The boss that knows enough to be dangerous. Usually has had some exposure to what you’re doing, and knows enough to get into trouble, but not well versed enough to know how to exactly do something.

The new general manager. Like when a sports team gets a new GM, usually they fire the coach, the staff, the players, and bring in everyone new.

Book smart, but practically not so smart. The academic. Knows what needs to be done by the book, has no idea how to actually do it. Lacks practice.

Notable things said to me by former bosses: 

“I was making nine figures before I came here” (why did you come here?)

Boss: “I need you to give me something like this.” 

(Shows me document)

Me: “Can I get a copy of that so I can recreate it for you”

Boss: “No, it’s from my old company and it has to be heavily redacted” 

Me: “So you want me to give you something like what you can’t show me”

Boss: “You’re being difficult”

Before my current assignment, I read Michael Watkins’ book, “The First 90 Days: Proven Strategies for Getting up to Speed Faster and Smarter”. While I wish I could tell you that I’ve been able to put into practice everything the book has said, it’s been my experience that things like that aren’t super cut and dry. That being said, there are good nuggets in there, and if nothing else it helps me focus on things I need to work on. Here’s one of the nuggets:

Fundamental Propositions (From the first 90 days – taken from HERE)

1. Transition failures happen when new leaders either misunderstand the essential demands of the situation or lack the skill and flexibility to adapt to them. 

2. There are systematic methods that leaders can employ to both lessen the likelihood of failure, and ensure that they reach the breakeven point faster. 

3. The overriding goal in a transition is to build momentum by creating virtuous cycles that build credibility, and avoid getting caught in the vicious cycles that damage credibility As a vicious cycle takes hold, the organization’s immune system gets activated and the new leader is attacked by clumps of ‘killer cells’, encapsulated, and finally expelled; it’s not nice, and it can get messy. 

4. Transitions are a crucible for leadership development and should be managed accordingly. They are an indispensable development experience for every company’s high-potential leaders. 

5. Adoption of a standard framework for accelerating transitions can yield big returns for organizations.

Regardless of whatever book you read, one thing remains clear. A new boss is anxiety-inducing for both the boss and the employee. However, you (and I) are 100% responsible for your relationship with your boss. Sometimes those relationships don’t work out, and that’s okay. I’ve had to learn what type of boss I want to be, and I’m still learning. Sometimes those lessons are hard, but with each opportunity to either get, or have a new boss, there’s a new opportunity for education and growth. Knowing it affects both the boss and employee, acknowledging this, and working within that framework during the transition will ease the transition. And if not, you’ll be working for a new boss, soon enough.

3 thoughts on “A New Boss”

  1. I think that being a new boss might be worse than getting a new boss… because when you become a new boss, odds are you probably get getting a new one too and have to deal with both sides simultaneously.


  2. The challenges of being the new boss are not the same for everyone, but all new bosses have them – whatever field you are in. I have read that the #1 reason people seek new jobs is due to the stress of their relationship with a supervisor. If that doesn’t cause added stress to the new boss reality, it will probably mean even more for the subordinate as the new boss is basically saying, “I am running the show now and you better remember that at all times!”

    Another issue for the new boss is expectations. Assuming YOUR superiors have been honest and forthcoming in their expectations of you does not mean you have the smallest inkling of what your new subordinates expect. Those hidden expectations can be land mines, to say the least!


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