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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.

Put yourself in Joe's shoes:

• 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 meetings


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


• etc...

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

Hey Joe, we really need you in the team, and 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.

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. Even better talk to the owner and put Joe into a one-person team under the owner.

Promote him to special agent.

My understanding is that at this point in time his status is independent of the team, his processes are independent of the team, his work allocation is independent of the team. He's not really a member of the team, and there's no compelling reason why he should be. Also, he's highly valued as an employee by the company/owner.

You already tried changing all that separates him from the team, and it didn't work. The only thing that makes him part of your team is the org chart. So try changing the org chart instead.

Ideally, you can talk with him and owner so he gets his special status acknowledged and he gets to fill his own specialized custom-fit role. If that doesn't work, just make his position special within your team - he's on your team's org chart and you're his manager but otherwise he's his own team, if possible with some title to end the "Why do I have to do XYZ when Joe doesn't".

You have in your team one of 2 people who grew this company from an idea to 150 employees. Instead of thinking how to get him to obey you, think how to use his proven abilities to grow small projects for your company and your personal advantage. It won't be harder than making him a team player - which as others who worked with that kind of employees suggested is next to impossible.

Putting him on fictional R&D role (like in anecdote in one answer) just to make him leave is effective but short-sighted. Think Woz - while working under Jobs leadership, he co-created biggest company in the World. But working without proper leadership was unable to make it again.

Some people are great at starting startups but bad at working in structured companies. But making them leave is stupid given the fact that the same structured companies pay millions or billions to buy small startups build by that kind of people.

Try to build with him a valuable startup within your company. If it works, you will gain big time. If not - you probably won't loose anything given Joe's position and respect from CEO. Anyway your team and relations with Joe will be better.

Write a memo to CEO (through your manager):

--

"After working with Joe for X, I came to understand, that his potential is misused - it's a wrongly allocated asset - like a race horse put in a carriage or Han Solo held in Rebels HQ [use an example tailored for CEO's interests].

As our company and it's structure grows we are more and more efficient but also prone to miss important trends or innovations - like Netflix. Leaving Joe in his current status is almost certain to make his usefulness for this company to vanish and even make him leave in the future.

Please let me work with him to find a innovative side project that he (under my supervision) could try to grow with limited resources into something bigger - just like this company grew. Preferably it should be something potentially disrupting our modus operandi - It is better to cannibalize your own business than letting some new obscure competitor did it to us.

It worked 10 years ago, we should try to work it again. Every smart company (not only Google) knows that one man with enough time and given resources in correct moment can disrupt whole industry.

It won't interfere with my team work - as a matter of fact it would also make my team work and morale better. Because Joe is mostly self-manageable, it also won't make my deadlines suffer.

I'm quite sure Joe will also prefer this more than to accept strict processes in my team and start to obey them."

--

I'm not a native English speaker so please correct any mistakes. Also remove examples that are "to much" for your CEO. The last one is not very subtle suggestion that he does not obey, so consider carefully if it's needed. If you can't get it to CEO through your manager, take this idea to Joe.

Here's the problem. Joe is right. It's just annoying that he is right.

• Joe has been doing his thing for 10 years.


• Joe has a proven track record of making choices that benefit the company


• Joe has a proven track record of making choices the owner approves of

I am sorry it falls to you to deal with Joe, but every company needs a few Joes. Your job as a manager is not to control but to enable. If you find yourself trying to control your team then "you're doing it wrong." Instead, try to enable Joe to do what Joe does best.

Joe doesn't want to log into Slack. That's fine. Enable him to find a way to communicate, that gives you and him what you both need. Have the slack feed email him. On this example, chat programs like slack can be a good form of communication but they can also kill productivity. Too many people expect an instant answer, or us it as a "sign" that someone is present so it's ok to go talk to them IRL. Maybe he doesn't want to deal with that. Maybe you can figure out why he doesn't want to slack and come up with an alternative.

Just remember you should be enabling your team, not controlling them. So you have to find a way to make it work. He has 10 years of doing things in a way the company and owner approve of, and the company has flourished because of it. If I was an owner I would do pretty much anything to keep Joe happy, just because he had been here so long, has shown loyalty, and success.

Promote Joe

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.

So in a nutshell, Joe isn't really the problem, it's the attitudes of the other team members. That's not to say they aren't justified. They probably are completely justified. Rules are rules, after all, and Joe is a peer.

The simple answer is to remove that justification. Promote Joe to a position where the rules really don't apply to him. For example, he could be chief scientist or vice president.

You don't even have to pay him more, or change his job. Just the title should silence the haters. And the dotted line on the org chart will relieve you of any responsibility if his recklessness breaks something.

Owner thinks Joe has special value. Make it formal.

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.

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.

If he is still with the company he has demonstrated he is capable of delivering time and time again.

when he needs an exemption, decision, or anything "nonstandard" he can go right to the owner and gets it approved on the spot.

The owner trusts his decisions and wants "Joe" to deliver as he sees fit.

Even though I don't have any personal issues with him or his work performance it's causing some tensions in the team.

It should not be too difficult to let the team understand his position as the senior member of the company.

At the end of the day everyone is getting paid for the value they are delivering to the stakeholders. As the person managing this person, your job is to make sure he delivers value and seems like he is already doing that. If you try to work against him you will be

1. Blocking him from delivering value and so failing at your job


2. It will not work since owner is the owner and calls the shots

Work with him. Unless he is intentionally disrupting the team give the guy the space to do his job. Do not cause undue stress just because he does not use some messaging app.

If having your "subordinate" work autonomously from you is bothering you too much I would look into another job. The situation is the owner's call and from what you re saying like he is happy enough with it. There is not much you can do unless, again, he is being overtly disruptive.

Here is a Joe. Not your Joe, but somebody else's Joe and I have Joes in my team, and I am working a customer team with an extreme amount of Joes.

Did you ask Joe why Slack is problematic for him? Very often Joes have good reasons to follow a certain procedure. Potentially these Joes are the ones who get shit done, and potentially they are very stubborn if people wants to bring them away from getting shit done.

This may now sound harsh, but yes, a single technically highly qualified and talented person can, if left alone in the right moment, sometimes out-weight a whole team. It can be a reasonable decision on Joe's behalf to increase the threshold at which people communicate to him. Potentially he found, for the tasks which he typically does, that the input of the others is not relevant (which may be true). So if Joe doesn't want to use IMs to communicate, I would accept it. Potentially he likes if people think about emails when they contact him.

My advice is:

• Address only the biggest issues first (to me that seems that a senior person doesn't join a planning meeting)




• Try to figure out which problems he has with Slack (probably the expectation to answer directly and the workflow disturbance)




• Try to figure out if he actually has an independent problem (like being disappointed on his career development) - maybe he doesn't have a goal career-wise any more.

As to answering the questions of your team "Why do I have to if Joe doesn't?", you should clearly answer that it is none of their business to look at what Joe does or does not.

I work as a team lead in a similar company with similar colleagues and I tried them as not entirely part of my team. Team membership is a bit of a fluid thing and some people exist more or less at the periphery (we also have parts of the company where it's normal that people are part of multiple teams).

For the part of this team member's activities that are part of your team, notably those where close co-operation with the rest of your team is essential, you have to be very strict with him on the way your team does things. On things that he does where he can function as a one man team, he's free to do as he pleases. He's probably most useful on that kind of work anyway, as that was the sort of thing he did from the beginning.

Of course I would inform both him and my own superior about the way I treat him.

That puts me in an an awkward position - he's in theory my "subordinate" but in reality he ignores me,

That's only on paper, but in reality you have no power over Joe. If you are no power over him, you aren't his boss no matter what your contract says. You have to understand as long as Joe has support from the owner who pays your own salary, there is nothing you should do.

You will not disagree Joe, anything he has support from the owner is the laws. Breaking his laws/beliefs is a crime. Apparently, you've been breaking the laws often by going against Joe's wills.

Manage your team as if Joe was you direct manager. Make him happy so the owner would praise you. The only thing that defines right/wrong in an organization is power, unfortunately you lost the power struggle battle.

... 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...

As long as Joe has support from the owner, it's your own fault for settling on Slack. Joe, who is your de-facto manger had not approved your idea. Please do what exactly Joe demanded you to do.

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.

Again, had you asked for permission from Joe for a regular fortnight meeting?

Please note Joe must have contributed significantly for the company to make it a 150+ company. The owner has the trust on him. Please thanks Joe for his works leading to your current job.

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.

Check out Manager Tools‘ „Corky Story“. It highlights the only way you can deal with an ineffective long-term direct report who is well-connected with your bosses.

TL;DL: Do your work as a manager by giving constant constructive feedback in regular 1-on-1‘s, document Joe‘s performance over sensible timespan (>6 months) with the explicit goal of getting him back on track to be an effective team member. Termination should be the absolute last resort for you exercising your role power after you have done your homework — which, let’s be honest, at this point you have not.

The problem is that you're making too many excuses for Joe. If he is expected to follow the same rules and procedures as the rest of the team, and you are his manager, then it's your job to enforce them. It's irrelevant that Joe been at the company longer than you. Failure to do this has the potential to weaken your position with the team.

You need to sit down with Joe and have a conversation about what it is that you expect from him and the areas that you feel he is not delivering. If he fails to make the necessary changes, you must be willing to take disciplinary action as his manager. I see no reason why you should need to involve anyone else, unless for some reason you don't have the actual authority associated with being a manger, which is another problem entirely and something you'd need to address (you can't effectively do your job otherwise).

The only other option here would be to somehow redefine his role as such that he doesn't follow the same rules and procedures as the rest of your team. This could be tricky/dangerous to pull off, however, and I wouldn't recommend it.

Finally, if Joe has legitimate issues with any of these procedures, they should be brought to the entire team and worked out together. There's no excuse for simply deciding not to follow them personally, especially from a senior member of the team who should be expected to set a positive example.