When I walked into my skip-manager's office, I could immediately tell she was in a bad mood. We all have our hard days, and clearly hers hadn't gone well.
Jessica sighed and leaned back in her chair. "That sigh isn't for you. I'm just tired. What do you have for me today?"
I began to explain a communication issue I was encountering with a peer of mine in her organization.
She interrupted me. "I don't need or want to resolve conflicts between people in my org. You two need to figure this out. What else do you have for me?"
She might have been a bit short with me, but I deserved it. I had an opportunity to speak with my skip-manager, and I was wasting it. The topic wasn't interesting for her, and it wasn't useful for me. I was lucky she was candid in her quick feedback so that I could move to a better topic.
The most frequent question I've received recently is around how to take advantage of a skip-level meeting. That's a meeting with your manager's manager. This is valuable visibility if you're interested in career growth, and a fantastic way to see what topics matter to those two levels above you.
Scope of influence and time
The main thing to recognize is the difference between levels at a company. The higher level position tends to mean a broader scope of influence, and focus on a longer time horizon.
If an engineer influences a single web service, their manager is influencing a suite of services, and their skip-manager is influencing a long list of services and products. At each level, you are paying attention to the interconnections between a broader list of things. Due to the broader list of things you influence, it is necessary that you focus on fewer details.
The time horizon for the lowest level employee is the next week of work. They focus on what's in front of them. In contrast, the manager focuses on the next quarter of work, and the director and higher is focused on the upcoming years.
If you are invited to a skip-level meeting, the person you are meeting with cares about broader topics, and longer time horizons.
Discuss things at your level or theirs?
Sometimes people make an argument that skip-level meetings are useful for a senior leader to "stay in touch" with the details. I don't think that's a valid argument in most cases.
Is it useful for a senior leader to know which Java version you are using? It's not a useful fact for them. Is it useful for you to understand the business model for your product? Absolutely.
Is it useful for a senior leader to know what bug fix is launching this week? Generally it doesn't matter. Is it useful for you to know where your product is going 3 years from now? 100%
A skip-level meeting should provide insight and learning to the lower level employee. Along the way, the senior leader gets a chance to learn more about one of their employees, and this provides valuable visibility to employees interested in growth.