Account Management

My boss is bogged down with EOY work but my first 100 days are coming up and when I started, they said we would do an evaluation then. Is it pretentious for me to put in a calendar invite a month out?

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I think it’s admirable that you are acknowledging your boss’ current workload. Work happens and, often, it can come first. If someone on my team put time on my calendar for a chat a month out, I’d welcome it. And be thankful they took care of it and respect that my team member’s growth is just as important as the work on my plate. But that is me. It’s important for you to look out for you in the sea of business.

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Just tell them you're planning on doing it as an informal FYI/"that's okay, right?" kind of way and then go ahead and schedule. In the off chance they could take it as a slight that you'd assume you can dictate to them how this goes. You never want to catch bosses off guard. But being proactive in thinking and checking in with them to ensure a blessing is totally fine and a great idea. And btw, you may also be surprised to hear they've also been thinking about it already or started collecting feedback from others and haven't told you yet.

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It’s a good practice to politely ask before scheduling a meeting. A good manager will make time for this.

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(cont) I don't want to come across annoying but I want to put it on their radar well in advance so they can at least think on it when they can. WWYD?

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