One-to-ones when there are no corridors
The conversations that happened incidentally in an office do not happen at all remotely, which makes the scheduled one carry much more weight.
In an office a manager picks up a great deal without meaning to: who looks tired, who has stopped contributing in meetings, who is having a difficult week. None of that transmits through a task board. For broader context on online meetings and collaboration, Microsoft Teams is a useful reference.
The one-to-one therefore has to do work it did not previously have to do, and treating it as a status update wastes the only channel available.
Keep project talk out of it
The one-to-one will fill with project questions unless there is somewhere else for them to go, because project questions are urgent and the other kind never are. For a practical software-side reference on documenting expectations and follow-up, this guide adds useful detail.
This means the fix is upstream: a separate rhythm for work coordination. Without it, no amount of intention keeps the one-to-one from becoming a status meeting.
Thirty minutes fortnightly surfaces more than ninety minutes quarterly. Long gaps turn the conversation into an occasion, and people prepare an appropriate account of themselves for occasions.
The agenda belongs to them
Start with an open question and leave enough silence for it to be answered. A manager arriving with a list gets a meeting about the list.
Questions that reach past the work: what has been more frustrating than it should be, is anything unclear about what you are meant to be doing, is there anything I am doing that makes your work harder. The last one is uncomfortable and produces the most useful answers, provided the response to a critical answer is not defensive.
Ask about isolation directly
Remote workers frequently do not raise isolation, because it feels like a personal failing rather than a work issue. Asked directly and matter-of-factly, most people answer honestly.
The practical follow-ups are concrete rather than sympathetic: who have you not spoken to lately, would a regular call with someone in your area help, is there a reason to travel that would be worth it.
Video, and be present
A one-to-one conducted while visibly reading something else is worse than no one-to-one. In a distributed team it may be the only sustained attention that person gets from their manager in a fortnight.
Do not cancel them
Cancellation is the most damaging thing a manager does to a one-to-one, and remote managers cancel readily because there is no social friction in doing so — no walking past the person afterwards.
After the second cancellation, people stop preparing. Reschedule rather than cancel, and if it is being dropped repeatedly, that is information about workload rather than about the meeting.
Write down what you said you would do
A short running note per person: what was raised, what was agreed, what happened. Reviewed at the start of the next conversation, it takes two minutes and is the entire mechanism by which the meeting acquires credibility.