What’s the easiest way for clients to send large files?

A link where they can upload directly, rather than email attachments, which often fail above 20–25 MB.

How often should I follow up on a file request?

A first reminder about three business days after asking, then weekly, mentioning only what’s still missing. Stop as soon as everything is in.

Do clients need an account to upload?

They shouldn’t. Every login you add means fewer files back. A private link per client is enough.

How to request files from clients (without the back-and-forth)

Asking a client for files sounds simple until you’re three emails in, holding half of what you need. The method you use decides how much chasing comes after. Here are the five common ways to request files from clients, what each is good for, and how to make whichever you choose actually work.

1. A plain email with attachments

The default. It works for one small file from a client who’s quick to reply. It falls apart with several files: attachments get split across replies, large files bounce, and you end up searching your inbox to see what’s still missing.

If you use email, put every item in one message as a numbered list, and say which format you need (“PDF, all pages”).

2. A shared folder link

Google Drive, Dropbox or OneDrive folders give clients one place to put things, and big files aren’t a problem. The catch: a folder doesn’t know what’s missing. You still have to open it, compare it to your list, and email the client about the gaps.

3. A form with upload fields

Forms with a field per document make the list explicit, which helps. They suit one-off intake (a new client’s ID, W-9 and signed agreement). They’re clumsy when things arrive at different times, because clients have to find the form again for each file.

4. A client portal

Portals keep everything per client, with a login. They’re thorough, but every login is friction: clients forget passwords, and many simply email the file to you anyway.

5. A request with automatic follow-ups

The method that removes the chasing: one request that lists everything you need, a private link where the client can upload or reply without logging in, and reminders that go out on their own until each item arrives. The reminders stop for anything already sent, so clients are only nudged about what’s left.

This is what Follow Up With does, with one addition: an AI assistant writes each email for that client, reads their replies, and checks each file (right month, all pages) before it reaches you.

Whichever method you use

Ask once, for everything. One message listing every item beats a drip of separate requests.
Say exactly what “done” looks like. “September statement for the account ending 4411, all pages” gets the right file first time.
Give a date. A real deadline (“by Friday the 10th”) gets answered; “when you get a chance” waits.
Make it one step. No account, no app, no hunting for the original email.
Follow up on a schedule. Most files arrive after the first or second reminder, not the first ask.