Don't skip the skip-level meetings
Whether managing up or down, the benefits of communication, trust, and insight go beyond your direct managers and reports.
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As if you didn’t think you had enough meetings already, however, this is one you don’t want to miss — and on both sides.
A skip-level meeting is a meeting between an employee and their manager's manager (i.e., someone who "skips a level" in the chain of command).
Albeit many engineers might see this as a waste of time, this may have more to do with your team culture and its leaders. No doubt, many engineering leaders (Directors and above) incorporate these meetings into their schedule simply as a box to check and spend a few minutes to let reports know their efforts are valuable to the company. I can assure you, this is even worse than not having them at all — and likely why so many engineers find them useless. But let’s look at a few of the benefits, and ultimately understand why these connections matter not only for the business, but for your own growth, impact, and visibility into the manager in the middle — which is in fact the primary person that puts you on track for promotion.
Speaking directly with a higher-level manager can be particularly valuable if there are concerns or issues that they feel are not being addressed by their immediate manager, or simply wouldn’t have enough context to answer. Here are a few things you might consider:
My manager has me working on X but I feel Y is more important, can you tell me about this?
What are the larger key priorities for our team/department/company right now, and how does my role fit into that? This is especially valuable if you feel stuck working on the same project, but lack context and understanding of your own impact.
Is there any feedback or guidance you can provide on my performance or development? Understandably, asking for feedback might always be awkward, but make this a habit. If it’s only positive, or negative — ask specifically for something constructive. Challenge your leaders.
It’s also a good idea to come prepared with written questions (almost like an interview). You can let your higher-level manager even know near the beginning of the meeting that you have a few topics you’d like to bring up. And remember, this is also a great opportunity to be candid, whether it be excitement, frustration, or lack remorse. And word of advice, to avoid sounding “too emotional,” especially on sensitive topics, ask for permission to to be candid. Your answer will unequivocally always be yes.
At this point in your career, you’ve likely been used to managing already. But it’s good to keep in mind that these are still some of the most important meetings in your entire schedule. Have empathy, and remember that many of your skip-level reports might likely have been thinking about this meeting for days, or weeks, or even months depending on the size of your org and cadence. Therefore do not cancel it, or if you absolutely must, reschedule for as soon as possible.
Nevertheless, As a higher level manager, here are a few types of questions you might consider asking your skip-level reports during a meeting:
What’s on your mind? I frequently use this as a starter because it immediately triggers a thought process beyond how their day is and avoids a delivery of a status report. Plus it’s a little more direct than What’s up or How’s it going — which tend to yield answers like Nothing much or I’m fine.
Is there anything you need from me or the team to be more effective in your role? What challenges are you facing, and how can I help you overcome them? It might also be a good idea to clarify that you’d love to hear it, even if they think you’re not specifically capable of being able to make it happen (right away). For example, discussions around education budgets, or finances in general, might be better suited for VP’s or CTO’s, but it’s important to capture this information anyway
Tell me about your experiences with your manager. This is a great opportunity to understand first-hand the performance of your reporting manager. If you can, avoid aspects of feeling and emotion. i.e. How do you feel about Amanda, is she treating you ok? Instead, focus on events and have them walk you through interactions of things that actually happened.
The frequency of skip-level meetings can vary depending on the organization and the needs of the employees and managers involved. Some companies may hold skip-level meetings on a regular basis (e.g., monthly or quarterly), while others may hold them less frequently or on an as-needed basis. Personally I prefer monthly as the maximum time. Anything longer might be an indicator that the org is too flat and you have too few managers, leaving potential problems linger longer than they should.
In general, it may be helpful to establish a regular cadence so that employees know when they can expect to have the opportunity to speak with a higher-level manager and be prepared.
Remembering the why
Keeping in mind the goal is to build trust, foster community and open communication, and drive engagement to gain insight. Skip-level meetings are a useful tool for managers and reports alike to get a more holistic view of the organization and identify areas where they can support their team more effectively. Never miss an opportunity to talk to your people!