How to Talk to Your Skip Manager Without Going Around Your Manager

The first time I realized how much people underuse their skip manager, it was during a bad month.

We were in the middle of a release that had a regulatory deadline attached to it. The kind where “a week late” isn’t a joke, and “we’ll catch it next sprint” gets you a meeting with Legal. One of our teams was quietly stuck. Not blocked in a dramatic way. No incident. No escalation. Just slow, grinding friction: unclear priorities, a dependency that kept slipping, a product decision that kept changing shape. Everyone looked busy. Nothing moved.

I found out by accident.

I was the manager’s manager in this case. I dropped into a review meeting because someone was out, and I could feel it in the first five minutes. The engineers were polite, careful, and tired. The manager was doing that thing good managers do when they’re trying to protect the team and keep leadership calm at the same time. Everybody was “fine.”

After the meeting, one of the staff engineers caught me in the hallway and said something like, “I didn’t want to go around my manager, but… we’re not going to make it.”

That sentence shows up in some form every few months in most organizations. And it’s usually followed by a story where everyone was trying to do the right thing…