tl;dr:"Progressing, in general, is a two-stage problem: you need to discover where it is that you’d like to go, and then you need to take positive action to work towards it. In my experience, many people over index on the prescriptive “how” before spending enough time on the “what”. The search space of possibilities for your career trajectory is effectively unbounded, and can rarely be predicted over long enough periods of time. This is a feature, not a bug, and should be embraced."
tl;dr:(1) Start with a "micro-yes:" e.g. “I’ve got a couple of ideas for how we could improve. Can I share them?” (2) State your data point: e.g. "we said we’d ship this change by midday, but it’s 4pm.” (3) Make your impact statement: e.g. “our support staff are getting inundated with tickets because we said that it would be fixed earlier.” (4) End on a question: e.g. “what are your thoughts?” As a rule of thumb, most feedback should be positive.
tl;dr:Focus one-on-ones on coaching, less on status updates, which can be done asynchronously. Coaching should gravitate towards your report's conscious or subconscious interests in a situation and push them to answer the questions they raise themselves.