Think Your Skip-Level Is for "Visibility"? That’s Cute. It’s Not.
Levels in an organization garble communication. A skip-level meeting is an opportunity to communicate clearly. Most importantly, it helps low-level employees see past their blinders.
Welcome to the Scarlet Ink newsletter. I’m Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers and tactical leadership advice.
Free members can read some amount of each article, while paid members can read the full article. For some, part of the article is plenty! But if you’d like to read more, I’d love you to consider becoming a paid member!
For a quick terminology sync, a skip-level meeting is one where you “skip” a level in your management chain, and talk to your manager’s manager (your skip-manager). This is a common practice at most companies I’ve interacted with. And for both people in the meeting, it’s important to know the point behind this practice (which I’ll get into later).
I’m going to open with a brief story. For some Amazon context, it’s relatively famous for not being gentle with people’s emotions. The assumption is that being gentle with people is slow and inefficient. It’s faster to transmit opinions and feedback directly and quickly, and the recipient can swallow their ego’s tears and move on.
The reason I’m explaining this is that I remember this next story partially because it taught me a valuable lesson. And you should probably have context on how people at Amazon communicate.
When I walked into my skip-manager’s office, I could immediately tell that she was in a bad mood. I think a valuable soft skill at work is being able to quickly gauge if someone is having a good or bad day. It gives you some hints of where your conversations might go.
Jessica sighed and leaned back in her chair. “That sigh isn’t for you. I’m just tired. What do you want to go over today?”
I started to explain a communication issue I was encountering with a peer of mine in her organization (not under my manager). One of those standard Amazon problems of someone refusing to do work we really needed done.
In my mind, the communication issue was awkwardly far away in the organization, and talking to her might help. Perhaps she’d volunteer to get the problem solved.
She interrupted me. “I don’t need or want to resolve conflicts between people in my organization. You two need to figure this out. What else do you have for me?”
Ouch, shut down hard. I quickly pivoted to another idea of a topic I had, and we moved on with our meeting.
She was a bit short with me, but she was also right. I had the rare opportunity to spend private time with my skip-manager, and I was wasting it. The topic wasn’t interesting for her, and it wasn’t useful for me. It was better for me that she was open and honest in her quick feedback, so I could learn to choose better topics.
I’ve regularly gotten questions about how to improve people’s skip-level meetings. I think most people can recognize that it’s a great opportunity to talk to a more senior leader, but they don’t know how to take advantage of it. So let’s get into it.
Think of your skip’s scope.
The main thing to think about is the difference between levels at a company. Getting promoted rarely just means increased compensation. Higher-level positions almost always 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 every level up in the management chain, you pay attention to the connections between an ever-increasing list of people and things. Due to the broader list of things you influence, it is necessary that you focus on fewer details.
The time horizon for employees changes in a similar way. An entry level engineer might care about their next week of work. They focus on what is in front of them. Their manager might focus primarily on the next quarter of work, and the director and higher are focused on the upcoming years.
This means that whenever you go up your management chain, that person cares about a broader area, and a longer time horizon. They also (rightly) care less about details. In fact, at the skip-level, they may not care too much about anything you personally do.
As a quick math problem, imagine as a Senior Manager I could have 9 managers reporting to me, and each of them could have 9 engineers reporting to them. That means meeting with an engineer is talking to 1/81 of my team, or 1.2% of my organization. That can give you an idea of how much your personal work influences your skip.
This means a skip-level meeting shouldn’t be about you. That’s not the point. So what is the point?