Someone owes you something. A document, a decision, a number you need before you can do your own part. It was promised on a call two weeks ago, it has not arrived, and you have not asked about it.
You know exactly why you have not asked. Every version of the message you draft in your head sounds either passive aggressive or pathetic, and neither seems worth it for something that will probably turn up anyway.
It usually does not turn up anyway. Here is how to ask.
Why this feels more expensive than it is
Chasing someone costs you something that sending them a document does not. You are asking them to account for themselves, which puts them briefly in the wrong, and most people would rather absorb a week of delay than do that to a colleague.
That instinct is not weakness and it is not misplaced. It is the same instinct that makes people pleasant to work with. The problem is that it scales badly. One unchased thing is patience. Six unchased things is a quarter where you were blocked on other people the whole way through and nobody, including you, could say who was holding what.
There is also a smaller and more annoying reason, which is that by the time you get around to it you are no longer sure of the details. Was it two weeks or ten days. Did they say Friday, or did they say they would try for Friday. That uncertainty is what turns a thirty second message into a task you keep moving.
The timing question, answered plainly
The honest rule is that you can ask as soon as the date they gave you has passed. Not a polite buffer after it, not once it has become obviously unreasonable. The date was their number, not yours. Asking about it the day after is not aggressive, it is just treating the date as real, which is what they meant when they gave it to you.
If there was no date, and often there was not, then the trigger is the moment it starts blocking something. That is the thing worth saying out loud, because it converts the ask from a complaint about them into a fact about the work.
Where people go wrong is waiting for the delay to become large enough to justify the message. That logic runs backwards. The longer you leave it, the more the message has to carry, and the more it has to carry the harder it is to write. A week late is a one line question. A month late is a conversation.
The four sentences
A chase that works has four parts and fits in a short paragraph. No preamble about hoping they are well, no apology for bothering them.
Name the thing, and when it was due. Specific, not general. The pricing sheet for the Q4 renewal, due last Thursday. This is the part most chasing messages skip, and it is the one doing the work. Vagueness invites a vague answer.
Say what it is holding up. One clause. Without it the proposal cannot go out. This is the difference between asking someone for a favor and telling them where they sit in a chain, and the second one is much easier to answer.
Give them an easy out. Offer the reduced version. A rough draft is fine, or the number alone without the writeup. Most delays are not refusals, they are someone waiting until they can do it properly. Removing that requirement releases more stuck work than any amount of politeness.
Ask for a date, not for the thing. This is the one that changes outcomes. If you ask for the document you get either the document or silence. If you ask when you should expect it, you get an answer almost every time, and an answer you can hold them to.
That is the whole message. It should take you longer to decide to send it than to write it.
When it is the second chase
The second one is where people either give up or overcorrect into something stiff and formal, and both of those are worse than the alternative.
Keep the same tone and change one thing: reference the date they gave you last time. They said Tuesday, it is now Thursday, is it still coming this week. You are not escalating, you are showing that the previous answer was recorded. That alone changes how the third answer gets given, and it does it without anybody being told off.
If there is a third chase, stop chasing and change the shape of the thing. Offer a call, propose doing without it, or say plainly what you will do if it does not arrive by a date you pick. A commitment that has survived three reminders is not a commitment that needs a fourth one, it is a commitment that has quietly ended and nobody has said so.
The part that actually makes this easy
Everything above is technique, and technique is not usually what is missing. What is missing is the record.
Almost nobody can answer the question of what they are currently owed. Not roughly, and definitely not with dates attached. The promises other people make to you arrive scattered through email and chat and meetings, they are made in passing, and they leave no trace anywhere you would look later. So chasing becomes an act of memory, and memory is exactly the thing that fails under load.
This is the half of accountability that gets almost no attention. There is an entire industry built around organizing what you have to do, and essentially nothing built around what you are waiting on. Your task manager holds your work. It does not hold Sarah's promise to send you the contract by Friday, because you never typed that in, because at the time it did not feel like a thing you needed to type.
Wasp reads your incoming mail and meetings and pulls those out as they happen. Who promised what, to you, and by when. It errs on the side of asking rather than assuming, because a wrongly recorded promise means chasing someone for something they never agreed to, which is worse than missing one. When the date passes, the item is there with the original message one click away, so the chase takes thirty seconds and reads precisely rather than approximately.
The technique matters less once you have that. Most unsent chases are not a failure of nerve. They are a failure of recall, dressed up as a failure of nerve so that leaving it feels like a decision.