Question Details

No question body available.

Tags

professionalism communication colleagues career-development manager

Answers (5)

Accepted Answer Available
Accepted Answer
June 26, 2025 Score: 10 Rep: 50,239 Quality: Expert Completeness: 50%

This really really REALLY depends on a lot of Context.

As others have pointed out - this is generally going to be poorly received by your direct Manager.

However, the reason I am giving this answer is there are some circumstances where this can be okay:

  • The person in question has talked about things like upskilling, cross-training or other such words that indicate that the company wants to foster the type of culture where this would be okay.

  • This is something your direct line manager has talked tangentially about in your 1:1 in regards to career goals.

  • There is a particular project that would require you to work closely with your Managers' Manager that you want in on and you have the skillset to assist.

And it is that last one that you could perhaps leverage. Say there was a particular aspect of your Manager's Managers workload that you wanted exposure to - say Contract negotiation with a 3rd party vendor.

You could have the conversation along the lines of:

"I am interested in being a fly-on-the-wall for Insert topic you want exposure for - as it is something I would like to experience for my professional development"

This is not the same as asking for direct 1:1 coaching, but in practicality - will have much the same effect. It doesn't carry the same implication of bypassing the management chain as a regular 1:1 coaching session does - as ostensibly the scope is smaller and just for whatever it is you cited.

Finally

Rather than push for it, keep and ear and an eye out for opportunities to have this time organically - for example: I work full-time remote, I am quite a loudmouth on Team Meetings (as in, I ask questions, banter etc.) so I am known to upper management.

About 2-3 times a year I will visit the Head Office (in another city - about 4-5 hours away) - I have family in that city, so I stay with them and work from the Office - and often when I come up (on my own dollar) - because it is a 'special' event, Some of the Senior Management Team will want to have a beverage with me over lunch or similar. Nothing too fancy - but at a local cafe a short walk up the road from the office and in an informal setting.

Those sessions are worth their weight in gold.

And the pretense is "Hey, I am up here visiting for a few days - let's grab a drink!"

June 26, 2025 Score: 14 Rep: 391,607 Quality: High Completeness: 10%

Would it be considered overstepping to request a skip-level 1:1 coaching session with my manager's manager?

It would be inappropriate.

It's not your manager's manager's responsibility to grow your career.

June 26, 2025 Score: 4 Rep: 941 Quality: Low Completeness: 20%

Some organizations (well-run ones IMO) have formal coaching or mentoring programs. If yours does not, the appropriate thing to do would be to suggest to your direct manager the idea of creating one - then let them take the initiative of moving the suggestion up the chain. Alternatively some organizations survey employees for engagement and morale purposes - that would be the appropriate time to raise such a suggestion.

In the absence of those arrangements, approaching your manager's manager for coaching runs the risk of not being well received. It could be perceived as bypassing the management chain or undermining your direct manager.

June 26, 2025 Score: 3 Rep: 1,209 Quality: Medium Completeness: 30%

You may think that this is a smart move in theory, but the reality is that a lot of managers would get defensive or feel disrespected about skip-level conversations, even if you frame it as career development.

Your intent even though it is somewhat reasonable and that you’re not trying to stir anything up or go around your manager. But the thing is, not everyone sees it that way. Specially if your organization doesn't have a culture for skip meetings (I have yet to see one, where it is). Your manager might feel you're questioning their ability to support your growth, because it's their job to support your career growth, not your manager's manager's.

So, in my opinion, weigh in what you stand to lose in case this doesn't go your way. The only possible way that comes to my mind is that you try to find a gap in your vertical that your direct manager doesn't support/isn't an expert in and with his blessings, you can explore a possible way for all three of you to connect and get some counseling.

July 2, 2025 Score: 0 Rep: 4,936 Quality: Low Completeness: 30%

My own experience is that this is usually fine. Seeing the other responses, clearly this is not universal, so I will also consider the limits to that advice.

I have worked in at least two firms where skip levels were a common practice. The first was a medium sized Australian firm, the second a large American multinational. It was not unusual to have a meeting or two a year with your boss's boss. I even had one or two meetings over my time there with the level up again. It was an encouraged practice, and a way for more senior managers to keep in touch with reality on the ground. Managers were considered responsible for the development of everyone in the organisation rolling up to them, and not just their direct reports. This is a philosophy of management I personally agree with.

In this context, requesting a skip level meeting was not seen as unreasonable, though it is a little forward. The specific request may still have been redirected towards other forms of development, such as training, mentoring, or links with groups solving the problems you are interested in. Blocking a skip level by default would have been seen as a strange, defensive behaviour by a weak manager with something to hide.

Given the other answers to this question that requesting a skip level meeting would seen as a personal attack of some kind, clearly this depends on the corporate culture of the organisation, and probably the society around it as well. So if you don't see an existing skip-level culture, perhaps tread carefully.

Even when there is a skip-level culture, people would sometimes use it as a way of lobbying for advancement rather than joint problem solving. This was usually not a good use of the time or something that impressed managers. What the meetings were good for was sharing constructive feedback and making problem-solving suggestions that people had direct experience of, but weren't able to solve within the scope of their everyday work. Thinking about bigger problems, design and problem solving discussion, and offering concrete improvements when given the chance, setup advancement opportunities. Straight lobbying did not.

Related to this, I would also add a bit of a frame challenge. You mention career planning as a motivation. You should ask your direct manager about career planning. Some form of formal or informal mentoring by a third person, not in the management chain, might also be a good option that might be more useful than a skip level meeting. It would also be less confrontational. In my experience, more specific suggestions and requests are easier for a manager to help solve than open-ended career musings, though.