The deploy is stuck, or a customer is asking about a contract clause, or a certificate is about to expire, and the one person who knows the answer is on a beach for another eight days. Their out of office says contact the team. You are the team, and you do not know.
Most of the time, the right message to someone on holiday is no message. Before you write anything, honestly try to avoid it. Search their old messages and documents. Ask whoever covered for them last time. Ask whether it can wait eight days, and if the answer is that waiting would be unpleasant but survivable, it can wait.
Sometimes it cannot. Then the way you write the message decides whether you cost them two minutes or their afternoon.
Make it answerable in one line. Not a summary of the situation and a request to take a look. A single question with the choices laid out. Is the renewal password in the shared vault or only on your laptop? If it is the vault, I have what I need.
Say what you will do if they do not reply. If I have not heard by noon tomorrow, I will roll back to Tuesday's version and we can sort out the rest when you are back. That sentence matters most. It tells them they are not required, and it lets them stay away without feeling they abandoned you.
Choose the channel they would choose. Many people mute work chat on leave and would prefer one text message. Others would be upset to get a text at all. If you do not know, use the quietest channel that still reaches them, and send it once.
Keep it to one message. Do not follow up with updates unless they reply and ask for them. Every extra notification pulls them back into work.
When they return, thank them, and then fix whatever made the message necessary. Write the answer down where it belongs. Make sure two people know it next time. A holiday that had to be interrupted tells you something about how the team works, not about the person who was away.
Monday: list the questions only one person on your team can answer, and pick one to get written down this week.
– Asael Shinder
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