You're already ahead — here's how to keep sharpening

Why ask this

It's easy for a 1-on-1 to quietly turn into a status update that only serves the manager, and this question checks for that directly instead of assuming the format is working. A flat yes is worth pushing on with a follow-up, since most people won't volunteer that a recurring meeting has stopped being useful to them. Asking this every few months also gives you permission to actually change the format if the answer is lukewarm.

Why ask this

This is a narrower, more actionable version of asking how someone is doing, because it's scoped to right now and to something you can actually act on. People are often more willing to name a concrete blocker than to raise a general complaint, especially when the question implies you're ready to go fix it. Asking it every session also builds a habit of surfacing blockers early instead of letting them sit.

Why ask this

Development goals set at the start of a quarter are easy to lose track of once day-to-day work takes over, and this question forces an honest look back instead of letting the goal quietly expire. Naming the gap between what was planned and what actually happened is more useful than the goal itself, since it usually points at what got in the way. It also gives you a natural moment to reset the goal if it's no longer the right one.

Why ask this

Managers often assume they already know what kind of help someone needs, when the honest answer might be something small like protecting their calendar or something bigger like advocating for them in a room they're not in. Asking directly instead of guessing means the support you offer actually matches what they need instead of what you assume they need. It also signals that helping them succeed is something you're actively thinking about, not just a line you say once a quarter.