my manager sucks at his job — should I talk to his boss?

A reader writes:

I am looking for some advice on how to deal with my manager.

I have worked in this organization for about three years, and my manager, Mark, started a few months before me. Out of all of the managers I’ve ever had, he is by far the kindest and most flexible (he’s very hands-off). After a few months, I realized he is not great at his job. Over the past three years, more and more of his job responsibilities have been put onto my plate. I am supposed to be in a more technical role, but I end up dedicating a lot of my time to managing, due to him … not managing. Some examples:

* Interns: We have a small team of interns — 6-10 in any given year. When I first started, they were pretty unprofessional, always late, and had not been trained. I asked Mark to implement training for them moving forward. What was supposed to be a team effort turned into me developing an onboarding manual and training presentations, completely on my own. At this point, all of these interns consider me their boss, because Mark is so hands-off with them. When I ask him to intervene on issues that affect my work (no-showing, unprofessional conduct), he makes excuses for them, because he feels bad for them.

* Budget: My role is very much shaped by our budget. When I was onboarded, no one shared any numbers despite my repeated requests, and at the fiscal year end, I learned that we underspent by quite a lot of money. Meanwhile, Mark had actually led me to believe that we were short on funds! Since then, I am now our team’s go-to budget person. The only part Mark is involved with is signing off on expenses (he doesn’t do his due diligence on these either— he comes to me to ask if he should sign off on them!).

* Disorganized: My boss is extremely disorganized, to the point where I am cc’d on emails from my grandboss, other managers, etc. so I can respond or remind him to. People often message me to ask if I can follow up with him in-person to check his email. Last year, my grandboss had me do one of our annual reports with limited notice because Mark had taken vacation while it was due, without ensuring it was done beforehand.

* Bad at technology: About once a month, Mark claims that all of his calendar invites disappeared (he refuses to go to IT). It is not uncommon for him to come into my office on the wrong day a scheduled meeting (like a week before or a day after) and ask when it will be starting. Outside of calendar issues, he has over 5,000 unread emails. Most of my emails to him go either unanswered, or he tells me his reply in person, which is unhelpful when I am emailing him to get a paper trail. When I do receive an email from him, they often have numerous spelling mistakes and spell people’s names wrong (or misname people entirely).Several times, I have found him tallying our reporting numbers by hand in a notebook, despite them being in a spreadsheet. This is after I’ve taught him basic Excel formulas that could do this for him in five minutes.

* Unprofessional: I often overhear him watching YouTube videos and movies at his desk. He has fostered an “us versus them” environment in our office, often bashing other teams, giving our team members the impression that our organization is against us. He is very open about some of his political beliefs that explicitly don’t align with our organization’s values.

These are just some of the larger issues that I am working with. I have been managing up (or at least trying to) but it has turned into me managing. I talked with my grandboss about it once about a year ago, and they agreed with all of my concerns and told me they were struggling to manage him. The problem is, Mark is a sweet old man (well past retirement age) and people have a hard time telling it to him straight.

I really love my job, but these extra responsibilities have taken me away from the role I was hired for. I have tried talking about this directly with him, but nothing ever changes.

If I’m being completely honest, I would like to see him let go. My company is in a financial crisis, he makes well over six figures, and after years of intervention and training, he has shown no improvement. Is there any use in talking to my grandboss for help or should I just look at opportunities to leave?

Sure, you can try talking to your grandboss again — but I would assume nothing is going to change, until and unless you actively see evidence to the contrary.

It’s still worth another conversation with your grandboss because you never know. It’s possible that he’s been hearing other complaints too or has an increasing number of concerns of his own, and your conversation could be the tipping point. Or it’s possible that he’ll realize you are at a tipping point and he’s likely to lose you if he doesn’t act. Sometimes that does happen.

So have the conversation, and be very explicit about the problems. If you pulled your punches last time, be more direct this time. Just don’t expect real change, and let it be a pleasant surprise if you get it. (Also, an added advantage to going in expecting nothing to change is that it can help you come across as more detached / not particularly emotionally invested, and therefore more objective and credible.)

Simultaneously, while assuming nothing is going to change, think about what you want to do about that. If you knew everything would be the same a year from now, would you wish you’d launched an active job search earlier? If so, do it now.

Alternately, would you be interested in staying if you could turn your boss’s incompetence into an opportunity for yourself — like by pitching your grandboss on a formalizing a more senior role for you where it becomes your official job to do some of the work you’re having to do for your boss now (and are paid and titled accordingly)? Sometimes there can be opportunity (and pay-off) in being the person who steps in to make things run when a Mark isn’t or can’t. Other times, it’s just thankless work that you’re never compensated for. If it could be the former, would you want that? Or would you rather just get out regardless?

Any of those routes are reasonable ones. Just assume you need to start pursuing one of them, unless that conversation with your grandboss bears unexpected fruit.

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