How to deal with the new boss's power-tripping sidekick [closed]

Question

I'm a software developer in a small company. Recently the company hired a new department head after the previous one resigned. Thereafter the new department head hired his friend/colleague from his last job.

It didn't take long for dynamic between the boss and his new sidekick to alienate me and some others in the department. While not officially or in practice anyone's superior, the sidekick clearly fancied himself second-in-command, and engages in a kind of status-climbing, condescending behavior (though subtle enough to be imperceptible to those not on the receiving end):

• attempting to micromanage other employees, including senior ones
• scheduling a daily meeting, serving no apparent purpose, which had the structure of him asking each team member in turn "what are you working on today?"
• casually dropping facts in to conversation that emphasize his in status with the boss, including company details he was privy to
• using the royal "we" as a status differentiator: we really appreciate your work on this project
• eagerly taking credit for others' work, not thinking to give credit to others where due
• expecting junior members of the team to account for their whereabouts, yet not bothering to inform the team when he himself will be away from the office

All this might not be so bad, except that the boss clearly plays favorites with his sidekick. Again, the behavior is subtle, but it clearly suggests a kind of two-man clique. Furthermore, the sidekick has (wisely) schmoozed with other departments and has them in his corner. The resulting dynamic has been quite frustrating for me and for the majority of the dev team. Our only solution has been to try and leave as quickly as possible.

I'm trying to learn from this experience and gain some perspective. These are the questions I have.

1. Regarding the sidekick: Is this a common type of character in office environments? I'm reminded of Dwight from The Office. If so, what is the best way to deal with or neutralize someone intent on ingratiating themselves to superiors, and going on creepy power trips? My approach has been to try and ignore him, but of course that was not productive. Do I have to become the office Jim, using sarcastic humor to take the office Dwight down a peg?

2. Regarding the boss: To me, the fact that he needs such a sidekick indicates that he's insecure as a leader and the fact that he overlooks his sidekick's officious behavior suggests that he's not serious about building a cohesive team. I would like a reality check: is there some kind of etiquette that my boss is breaching by appearing to play favorites with his sidekick? Or am I being too sensitive?

3. Lastly, do you see any resolution that doesn't involve me either being miserable, or leaving the company? Would it be advisable to talk to the boss and relay my feeling that I am not in the "inner circle"? Would it be better to go to HR and openly communicate my concerns?

Answer 1

First, to continue the riff on The Office, let's refer to the boss as Michael.

(Before we take this too far, though, recall that The Office is a work of fiction, written by people who probably never worked in a real office. To your question #1, if you play the role of Jim to Dwight and Michael, things are unlikely to turn out well. The real world is less funny than fiction, and the stakes are higher. Things are, however, often more absurd in reality than in fiction.)

I'll take your complaints at face value instead of second-guessing them like some of the other answers. I can see how this is an uncomfortable situation. You guys have been at the company for a while, and you get a new boss Michael, and he brings in his buddy Dwight. If Dwight has the authority to call a daily status meeting, and he's ingratiated himself with the other department heads (Michael's peers), he probably really is in a position of some power. Michael brought him on board so it's clear he thinks Dwight is a great guy. If you get into some kind of political battle with Dwight, you will most likely lose.

It may also be that Dwight really is an asshole. But bear in mind that nobody thinks they're being an asshole, even actual assholes. You should try to consider things from Dwight's perspective. I'm not sure this will actually help anything, but you might gain some insights.

To your question #2, it might or might not be the case that Michael is insecure. I'd guess that Michael has brought Dwight in to run the dev team (your team) while Michael focuses on coordinating with other departments and with his management ("managing upwards"). Suppose Michael really is insecure, and he can't face up to a team full of whiny, prima donna engineers like you. (J/K!) What are you going to do about it? You still have to deal with Dwight.

On question #3, the only reason to go to HR with an issue about your management is if something like harassment or criminal activity is occurring. HR's official responsibility is to protect the company from legal liability. (At least, this is true in the U.S.) Sometimes they view themselves as a sort of ombudsman to sort out interpersonal conflicts, but I believe this is rare. Obviously you're more aware of the specific role of H.R. at your company.

On what to do, I can think of a number of approaches.

1. Just hunker down and stick it out. Things might get better. Then again, they might get worse. They rarely stay the same. If things get worse, leave.
2. You could try to develop a relationship with Michael. If things are as I speculated above, he'll probably just tell you to take your concerns to Dwight and work them out with him. He might tell you what he thinks the direction is for the organization, though. For example, if he sees the dev team doubling in size, it's perfectly sensible to delegate a supervisory functions to someone like Dwight. Then again, sometimes managers puff up their status by adding layers of hierarchy within their organizations.
3. You could try to develop a relationship with Dwight. Yes, you probably find this distasteful, but man up and take a shot. Schedule a meeting with Dwight, or perhaps go to lunch with him, and bring some specific, objective business concerns. For example, the daily status meetings interrupt your work and the time spent in them isn't worthwhile. He'll probably want to keep the daily status meetings, but you can gauge from his response whether he's a reasonable guy. In case he asks, be prepared with suggestions on how to streamline the meeting or alternative ways to accomplish the goals for which the meeting is intended. On the other hand, he might get all authoritarian on you (e.g., "This is how we're running things now.") in which case you probably have your answer: leave.

Answer 2

I feel the question is still too fuzzy but will try to help with what I can.

Just curious but why are you letting the sidekick affect you?

Most of the issues that you have mentioned don't really seem to be issues at all to be honest.

Calling a daily stand up is normal practice in Agile/Scrum, maybe that's just how they are used to operating and want to carry it over to the new environment, nothing wrong with that.

Casually dropping facts might be him trying to ensure that everyone is on the same page, that seems pretty normal. If it's not "facts" then I can see how it might affect your work but since they are, the point is moot.

Using "we" a lot when it comes to spreading praise is pretty normal as well, how can you know if he's not referring to the whole team?

As for micromanaging, I can think of many cases where anyone could be perceived as trying to do it. Most of us even do it subconsciously when we are trying to affect change.

The last two regarding claiming credit and double standards might be problems, but those are common in any workplace regardless of the person's rank or job title in my opinion.

All in all I think you might be a little sensitive. There is really no way to tell without more detail.

In any case, if he was employed by the new Head than he should be there for a reason. I would assume that one of the reason is to affect change and to help mould the environment into something that the new head is more comfortable with. Again, nothing really wrong with that. You can't really expect a change in leadership and have everything stay the same, else there would be no point in changing in the first place.

This also doesn't mean that the new boss is insecure. cases like this is often the exact opposite. It takes a lot of confidence to delegate something out knowing that higher management will look to him for accountability if his "friend" fails.

If you don't like the changes or the way the new "sidekick" is doing things. You will need to earn the new Head's trust so that he will try things "your" way. Whether you get this done by sticking to their changes and proving you know how to run that system better or by dialogue and discussion depends on your working environment and relationship.

In the meantime, I would suggest you try to develop a useful working relationship with BOTH of them to the point where you can feel comfortable about voicing your opinions.

Answer 3

1. Yes, there are always plenty of assholes in the world. However I think it's a bit naive to think that using sarcasm to "take him down a peg" is going to accomplish anything useful in this situation.

2. From your post it doesn't sound to me that the boss is necessarily aware of the other guy's behavior at all. It seems a bit presumptuous for you to assume that your boss is intentionally treating his friend as a "sidekick". The only thing you've indicated that your boss has actually done is discuss business details with his friend. But there's really nothing wrong with that by itself. If the guys are friends then probably they make small-talk from time to time, and possibly they hang out together outside of work and talk about whatever they feel like. It seems possible that your boss would tell you the same sort of information directly if you made an effort to talk to him about it.

3. I think talking to your boss is a reasonable first step. As I noted above, it kind of sounds like he may not even be aware that he's doing anything to create the impression that an "inner circle" exists. He might also be completely unaware of the superior attitude that his friend has adopted behind his back.

Also, some of your complaints might not really be valid:

• Scheduling a daily meeting, serving no apparent purpose, which had the structure of him asking each team member in turn "what are you working on today?" - I'm surprised you haven't encountered this before in your career as a software developer. That sounds like an entirely standard "daily standup" meeting. The typical agenda for such meetings is to go around the room and have everyone briefly describe 1) what they worked on yesterday, 2) what they plan to work on today, and 3) if there's anything keeping you from getting your work done. The purpose is to make sure that everyone on the team knows what everyone else is doing, to avoid situations where you have two developers simultaneously working on the same task, and to identify problems/blockers early so that they can be dealt with. Such meetings are a very common facet of agile development practices, and as I said, I'm surprised you haven't encountered these before.
• Casually dropping facts in to conversation that emphasize his in status with the boss, including company details he was privy to - Are you sure that's his motivation for doing that, and that he's not just trying to make sure you know the same information he does? Maybe he's trying to bring you into his circle, and you're just misinterpreting the gesture as one of superiority. Obviously this guy isn't here to defend himself, so I have to give him the benefit of the doubt. Dropping facts is not an act of superiority in and of itself.
• Using the royal "we" as a status differentiator - Maybe that's just how he talks? I wouldn't make too much of it. Some people are just like that.

That said, the rest of your points sound like legitimate issues, and probably the best way to resolve them is to take it up with your boss.