What to do when two timezones have no overlapping working hours

Take any pair roughly twelve hours apart and standard working hours produce an empty intersection. There is no clever slot hiding in there. Someone is going to take a call outside their working day, and the only real decisions are who, how far outside, and how often.

Quantify the compromise before you argue about it

'Early' and 'late' are not comparable units, which is why these conversations stall. Convert to something measurable: how many hours outside their normal window each person sits, and whether that lands in the range where people are simply up earlier than usual or the range where they are being woken. An 08:00 start and a 23:00 finish are both an hour outside a 9-to-17 day, but they are not the same ask — and a 02:00 call is not on the same scale at all.

The planner scores exactly this: distance outside each person's stated hours, weighted so that being far outside costs disproportionately more than being slightly outside, with an extra penalty for slots landing in the middle of the night. That is why its top suggestion is often not the mathematical midpoint — the midpoint frequently puts both people in a mildly bad place when one person taking a mild hit is objectively better.

Prefer edges to middles

When no overlap exists, the best slots almost always sit just past the edge of someone's day — the hour before they usually start, or the hour after they usually finish. These are cheap, because they're adjacent to time already committed to work. Pushing an hour deeper into the evening is much more expensive than it looks: it collides with dinner, childcare, and everything else a working day is bounded by.

Alternate direction on recurring calls

For a one-off, pick the cheapest slot and move on. For anything recurring, alternate which side absorbs the cost. Consistently loading one side breeds a quiet resentment that never shows up in a scheduling tool but does show up in attendance.

Ask whether it needs to be a meeting

• Status and progress: write it down. Nobody should be awake at 23:00 to hear a status update.
• Decisions with clear options: circulate the options in writing, and only meet if the discussion doesn't converge.
• Anything ambiguous, relational, or contentious: meet. This is what the awkward hour is for.
• Onboarding and pairing: meet, but schedule it as a dedicated block on a day when the person taking the hit has a lighter load.

Reserving the expensive hour for the conversations that genuinely need to be live is the highest-leverage thing you can do here. No scheduling tool can find an overlap that doesn't exist — but it can tell you precisely what the least-bad option costs, which is enough to decide whether the meeting is worth it.