I have 1 employee that have a direct communication with my boss due to some paperwork or contract that she always needs my boss to sign among other things. Sometimes my boss will tell her things that he expect her to give me an update on it because my boss is the CFO of the company, he might just think its easier to talk on the topic with her while they’re talking. In the end, my boss always ask me if my employee tell me about it when he and I talk and most of the time I am clueless about it

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Your boss needs to share the info with you not your employee. Your direct report is not your boss’s secretary to relay info back and forth between you and your boss. Since you know your direct report cannot be trusted to share info, this is something you really need to discuss with your boss so the 2 of you can establish better communication between you. And leave your direct report out of that establishment.

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You need to get looped into the conversation so you can provide adequate support to your direct report, should politics come into play.

helpful

I talked with my employee once to basically keep me in the loop but I have found her to actually sometimes keep the information from me on purpose not because she forgot. What would you do if you are in my situation? TIA

I would first thank the boss, “thank you for making me aware so I can address the issue. This was not on my radar.”
It’s not the your boss shouldn’t also know, you need the opportunity to manage and support your team. I would work on finding out why you aren’t finding out about these issues in a timely manner. It could be a matter of trust between you and your staff. I would look at that relationship the same way as any personal relationship. Communication happens after there is trust.

Thatttttt's a tough one. It also depends on your relationship with your CFO. I typically tend to have a casual enough relationship to where I can be real down to earth and just throw my two cents in when I see an opportunity and say something like "hey... could you try to keep X out of the middle-man communication? They tend to forget to relay and I don't wanna put all that on them anyways. Can you just send me a text or an email or whatever is easiest for you?"

I wouldn't say anything to make the employee look bad to my boss, because my employees are a reflection of me... ultimately... and ALSO... this employee might have some sort of weird power issue that you need to squash. Maybe they truly just forget. Maybe they're being put in a situation that is inappropriate and not their job to remember all these things they need to lackey from your boss to you. Maybe they like being told things from a CFO and having this information that their direct boss doesn't have. .... I did have an employee like this. I quit giving this employee info, at all, and ONLY gave info to my lead who has the proper role, responsibility and exemplifies the emotional maturity to be privy to information that no one else has. No issues since. DO NOT enable bad behavior and TEACH people how to treat you. My two main mottos and words to live by as a leader.

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