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I manage a DevOps team of ca 10 engineers in ~150 headcount software development company. One of my team members (call him Joe) has been with the company pretty much since its inception 10+ years ago, longer than anyone else apart from the owner.

Joe doesn't seem to have any ambitions to move up to middle management, he seems to be happy doing what he's doing in the team. However because he's been with the company for so long he tends to ignore the rules, processes and even the company structure. And he gets away with it because when he needs an exemption, decision, or anything "nonstandard" he can go right to the owner and gets it approved on the spot. Or he simply ignores what he doesn't like.

Quite often that's against my and my team's decisions - for instance we settled on using Slack for communication, alerts, etc. He doesn't bother logging in most days and insists we call him or email him if needed. Or we have all-team work planning meetings every 2 weeks, but again he can't be bothered as he says he knows what he's got to do.

That puts me in an an awkward position - he's in theory my "subordinate" but in reality he ignores me, and everyone else in the management structure and goes right to the owner if feels like it. I'm not in a position to go to the owner's office and deal with it the same way Joe can. After all I've been with the company for only a little over a year, Joe has been here 10x longer. I can only bring it up with my direct line manager but he doesn't seem to be able to do much as Joe is under sort of "protection" from the owner.

What should I do? Even though I don't have any personal issues with him or his work performance it's causing some tensions in the team ("Why do I have to do XYZ when Joe doesn't") and I'm not sure how to approach it.

This is the owner's issue IMO. Right now he can't see the impact that Joe's ability to bypass structure is having on the rest of the business, and as a result, he is complicit in enabling this to happen.

If I were you, I'd recommend scheduling a meeting with the owner and explaining that, although Joe is a good team member, his resistance to following agreed process is disruptive to the team, and therefore not good for the business as a whole.

If the owner is a smart guy and values his company more than his personal relationship with Joe, he would see your position and ideally bring Joe back into line. If not, then you have a real problem on your hands - the only way forward from there would be to get tough with Joe on a personal level, document all the ways he doesn't follow the process (e.g. refusal to use Slack) and if he then goes to the owner to claim you are being unfair on him, you can back up your position with evidence that he is the one causing the problems, not you.

Bottom line: either the boss cares more about Joe having free reign, in which case I don't see a way to solve the problem, or he can see your position and will take steps to bring him into line. I don't think this is something you can solve directly, since even though you have apparent seniority, Joe is disregarding it.

Because [Joe's] been with the company for so long he tends to ignore the rules, processes and even the company structure. And he gets away with it because when he needs an exemption, decision, or anything "nonstandard" he can go right to the owner and gets it approved on the spot. Or he simply ignores what he doesn't like.

There is an inherent problem here: Joe isn't being a team player. A 150 person company can't scale if every engineer (regardless of seniority) is running off and doing his own thing. Some may argue because Joe delivers you should leave him be. But if Joe can't coordinate with other members of his team, he's actually hindering the work of 9 people. Unless Joe can be a 1 man show (and you can fire the other 9 people), he needs to learn to work with his team and within the confines of the processes and rules. If he doesn't like the processes and rules that are in place, he should use his power to change them instead of just ignoring them.

I've worked with a "Joe" at one of my previous companies. He was the first engineer hired at a popular startup and had a direct line to the co-founders. But as the company scaled, he too was ignoring processes and having difficulty working within the new org structure. Enough people complained about him that the co-founders ended up put him in charge of a R&D division and allowed him to hand pick the engineers for his team. He was very ineffective leading the R&D group. After 1.5 years, they didn't produce any meaningful research and he eventually left the company. His team was disbanded and absorbed into the engineering group. The moral of the story is that people like "Joe" may seem like an asset to the company, but they belong in smaller companies with less structure. They prefer the wild west of early stage startups where anything goes. They hinder the growth of the company by ignoring rules which builds dissent among the other employees.

I recommend having a talk with Joe about how his actions make it difficult to coordinate with him and hinder the work of his team.

Put your shoes into Joe's :

• You've been working here for 10+ years


• You've been good at what you are doing


• Directly in touch with the owner, satisfying his requests, etc...


• Now this new manager 'trendy', 'new wave' etc... is coming up and telling me what to do


• I don't care about these new techs, new structure, etc... it was working fine before, why change?

So that's basically how he feels, and you can't approach this as a pure manager, you have to understand him as a senior developer.

What I suggest doing?

I think the main point is to come up with incremental steps.
First identify all the weak points that you want to 'fix' :

• A- Doesn't come in Slack


• B- Doesn't attend team meeting


• C- Hit up the boss directly bypassing the whole process


• etc...

Then slowly (over weeks) come up to him with 2 choices (let's say A,B) and say something in those lines :

Hey Joe, we really need you in the team, you are a core member (pat him a little). We need your expertise and be in sync more frequently, I've noticed you don't use Slack where the team communicates nor coming to the team meetings, could you please at least do one of them? That would improve the team work and we would all really appreciate that. (basically give him power/choice and make him thinks that HE chooses what he can do) I know you are not into those things (approach with compassion), we are just trying to streamline the process and get everyone on board, in sync.

The key points here, are putting first the TEAM WORK and that you UNDERSTAND him, don't make it like it's coming from you or like a personal favor. Get him involved in the process by giving him the choice to join the process.

Keep asking for A + B until he does one of them, then keep going with B + C (or A+C depending of what he does), etc... The more steps he will be doing, the more he will feel involved and the better it will go.

In the case of him doing 0 efforts and being 100% stubborn, you don't have many choices, IMO, but escalating it to the boss and try to talk with the boss + Joe in a meeting to clear things out.

This team member does not believe that your novelties and reorganizations (like using Slack instead of E-mail) are useful and sees them as unnecessary waste of time that should be spent on the actual work.

He may be wrong; depending on your experience he may also be at least partially right. Other team members may share his opinion but be afraid to show it so openly. He does because he feels more protected.

You need to convince him, and probably also more of the team, that your suggestions on work re-organization are useful and important. You need to explain why do you want changes, how do these changes make work more efficient and why are they needed now when it was ok without them in the past. Also think maybe some of your proposals are not sufficiently thought about.

Quite often that's against my and my team's decisions - for instance we settled on using Slack for communication, alerts, etc. He doesn't bother logging in most days and insists we call him or email him if needed. Or we have all-team work planning meetings every 2 weeks, but again he can't be bothered as he says he knows what he's got to do.

Actually, it sounds like there are two problems here. One is that your examples for non-conformity sound weak. In your position, I also wouldn't bother going to the owners office, if you insist in using slack instead of the telephone. I mean, if Joe thinks he can replace slack with a telefone call, why to use slack in the first place? If there are real advantages over the telephone, you can highlight them a bit and maybe convince the owner.

Two, if the problem is, that Joe rejects anything and he gets backup from the owner, you cannot do anything anyway. Main problem here is that this destroys your authority because the employees see that you cannot influence anything. The solution would be to go to the owner and speak about this problem, so that he either stops undermining your authority or you look for another job.