Work Dilemma Advice

Give him more responsibility. Maybe let him work the fries station?

Is this sincere or a troll? I’m tired and busy.

Is Carl a high performer or just needy?

just go talk to Todd and lay it out. You aren’t going to be able to do anything without his signoff any way. Best solution is to transfer Carl to another dept where that is more suited for his personality.

You can stop now, Carl. Carl, you can stop now. Gimme that wa-wa, Carl

invite Carl into the office. ask him if he is familiar with the term 'WFH'. at this point have the following track fade in.

as he tries to interject, rip off your shirt and join in on the chorus... you can work from home oh oh ohhhh

mic drop and usher him out of the office.

acquire a large amount of red dye and arrive at the office early morning. you will need to recruit a couple of assistants, does anybody else dislike carl? if not, pay them some money to be your accomplices. ask carl to arrive 30 minutes early when the office will be empty apart from you and your collaborators. as carl pulls into the carpark have them lie on the floor in unnatural positions with red dye pooled around them and splotches of dye leading to carl's desk. place a kitchen knife on his desk with more red dye. wait until carl enters the office and then emerge behind him and exclaim CARL WTF MAN WHAT HAVE YOU DONE

if all goes to plan, carl will run out of the office fearing for his liberty, go home, shave all his facial hair, don a wig and live the rest of his life 6 hours drive away as a maid named beatrice.

You're style may be laid back, but it shouldnt be lazy. If Carl has good ideas, there is no reason not to bounce them up the chain yourself (not as your own) and have those conversations yourself with Todd. Bring attention to Carl as a potential high performer. Also, if he is a high performer or psycho squirrel, leverage them. Let them tackle that pita project no one has touched for 5 months. Alternatively, if they're a douchnozzle, bury them in mind numbing but necessary tasks until they wither away or come back with Stockholm syndrome.

He should become a success in life and draw welfare.

Is your real problem Carl? Or is it Todd?

The more people you have reporting to you the greater the chance one of them will be a real pain in the neck. With 34 people reporting to you the probability if almost 100%. Todd ought to realise this basic fact of management and react accordingly. He should know that Carl is high maintenance and work with you to keep him on track and minimise his potential for disruption.

I don't like either of your proposed options (a) give him more freedom. b) lay down the law) as they appear to be you acting unilaterally. Whereas in fact you and Todd should be a team where Todd knows what you are going to do and approves it. That way you have cut-off the going over your head option right at the start.

You're not going to change Carl, he is what he is, all you can do is channel work in his direction that fits his personality. If he is a go-getter and likes to be thorough give him a project with multiple aspects running in parallel. The more balls he has to juggle the more occupied he will become - and maybe he will learn something about himself in the process.

I feel like I might be Carl.

If a subordinate of mine went around my back to my superior without my knowledge, undermining my authority over my team, I would fire them.

Carl may not have a full view of department or company drivers. Without that context he may not know how to self-select his demands.

For example: My company moved to 'unlimited vactaion' recently. In the old model where an employee had a defined 3-5 weeks off they would govern themselves and limit their vacation requests. Now that we have 'unlimited vacation' some staff members have no problem asking for time off because they don't experience the impact on projects or on company profitability. They only know that their next trip is to Hawaii. It puts the managers, like you, in a tough spot to approve/deny excessive vacation requests.

You could provide some transparency to Carl on how your department makes decisions. You might share the overall budget, for example, to help him limit requests to attend conferences or to purchase specialized equipment.