Mid-level Managers: how to communicate (upwards) effectively when you've been socialized to be hierarchical.
Mid-level management in a Tech workplace can be quite tricky. While staying technologically relevant so you can meaningfully support/guide your team with daily tasks, you also have to be adept at the human aspect of managing downwards (your direct reports) as well as managing upwards (your boss).
Interact with the person, not the "role"
Start by learning to interact with the person - not the role. Whether you manage someone, or they manage you, in the end, they are a person - just like you. Remind yourself that before and during every single interaction until it becomes second nature. You can learn to communicate without a specific "upward" or "downward" intonation (hierarchically speaking) and still be very effective in your job. I find that this approach helps to remove some of the irrational fears that come with perceived overstepping/offending.
Hyperfocus on the task at hand ("everyone is a contributor")
Don't be Overwhelmed
If this still feels uncomfortable or new to you, begin by watching how your own team interacts with you (who is their manager). How does your team "up manage" you? Can you borrow from their style and effectively apply those insights in "up managing" your own boss? Because you can learn from anyone, anytime, if you want to. It's never late to learn, or even unlearn, especially if old habits aren't helping you grow personally or professionally.