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Related: What is the purpose of 1-on-1 meetings with your direct leader/boss?

On a weekly or sometimes just bi-weekly basis I have a 1-on-1 with my manager. However once a month I have a 1-on-1 with my manager's manager.

At first I thought the topics I could bring up with my manager's manager would be somewhat similar in the 1-on-1's I have with my current boss, but that doesn't seem to be the case:

  1. When I bring up career planning, he says that's something I need to work with my manager on.
  2. When I bring up higher level company goals he more or less tells me the same thing my boss tells me.
  3. When I try to get more sense of prioritization of certain projects he tells me my boss is in the same meetings as him so there isn't much more insight he can give me.
  4. He doesn't and can't really give me feedback on what I am doing because he doesn't see any of the work I do directly.

I guess I'm just confused as to what conversations I should be having with him? If it's about my current boss well that seems a little trivial and I have found questions that recommend not doing that i.e. My boss is blocking my growth, should I bring it up in my 1-on-1 with his boss? so I'm just having trouble what I should bring up.

I don't want my 1-on-1's to feel like a waste of time to him and the past few have somewhat felt that way.

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    Why are you having these meetings? It's incredibly uncommon to have these as upper management should typically trust the managers below them to handle their own reports. I can't imagine these being useful if they're monthly. Who set this up? Have you asked this guy about the purpose of these meetings? – Lilienthal Apr 26 '16 at 8:32
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    I have these once a month just because of my boss's boss preference. He prefers hearing directly if there's any problems or if any has suggestions/improvements. We usually talk about what I'm working on, what could be better, and then just small talk after that. He's pretty laid back so I don't know what your situation is like. – Lexi Apr 26 '16 at 11:19
  • @Lilienthal Yeah I guess I was wondering this as well. He did serve as my boss for a period of time while we were looking for someone to fill my boss's role so there was a time I had weekly 1-on-1s with him but now it seems a lot less relevant. This is something that is done throughout my company though so I don't think this is just something specific to my team or my boss's boss. – Kevin Xu Apr 27 '16 at 0:56
  • @user14287117 Then it's best to just ask him directly what he wants to use them for so HedgeMage's answer seems like the way to go. – Lilienthal Apr 27 '16 at 7:09
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Ask your boss's boss what he thinks the best use of this time is.

The format of these sorts of things tends to vary a lot based on the culture and organization of a specific company. Unless the company is exceedingly dysfunctional, simply asking directly what your manager's manager would like to get from these meetings, and what he thinks you should have in mind in preparing for them, just shows that you're being thoughtful and asking the right questions.

It may be as simple as, "I've been trying to think about how to best use the time we've set aside for these 1-on-1's, but I'm not really sure what you hope to get out of them. Would you mind talking a bit about what caused you to start the practice?"

  • I guess I'm wondering how to phrase this in such a way that doesn't come off weird? The thing is I've had I would say at least 5-6 of these and some of them were helpful but most more or less felt like a waste of each other's time. I also have turned down some 1-on-1s (I feel so terrible but there was a lot of stuff on my plate those days so I asked if he could reschedule and he was open to it.) I want to be careful how I ask this because I can see it coming off the wrong way but maybe I'm overthinking it? – Kevin Xu Apr 27 '16 at 1:05
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    @user14287117 If he seems like a generally reasonable human, don't sweat it. Reasonable people don't hyper-analyze your phrasing. It may be as simple as, "I've been trying to think about how to best use the time we've set aside for these 1-on-1's, but I'm not really sure what you hope to get out of them. Would you mind talking a bit about what caused you to start the practice?" – HedgeMage Apr 27 '16 at 2:21
  • @HedgeMage That's a very good way to phrase it, consider adding it to your answer. – Lilienthal Apr 27 '16 at 7:08
  • Thanks I went ahead and accepted the answer. On my next one-on-one I plan to ask him and comment on what happens. Appreciate the advice everyone! – Kevin Xu Apr 27 '16 at 21:22
  • Just had a 1:1 with him and brought up the question and it went pretty well. In case people are curious, he said the point of the meeting was more for my sake to check in on how things are going for me and, more importantly, also to give me an opportunity to talk about my current boss if I needed to. If things are not going well with him and I didn't feel comfortable to bring it up directly, this was an opportunity to do that so he could step in if necessary. Thanks everyone! – Kevin Xu May 20 '16 at 1:58

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