The short answer
Reply on the same thread three to five working days after your first email. Add one thing they didn't have before and ask a single question they can answer in a line. If there's a real deadline, go a day or two before it instead, and say so.
That's most of it. The rest of this page is timing, wording and when to give up. (The timings are what we'd do ourselves. We haven't seen a study on this that we'd trust.)
Why it feels awkward, and mostly isn't
People put off following up because it feels pushy. We get it. But think about what usually happened on the other end: they opened your email between two meetings, thought "I'll answer that properly later", and later never came.
You're not interrupting a considered silence. You're picking the message back up off the floor.
What makes a follow-up annoying is how it's written. A third "just bumping this!" with nothing new in it is annoying. A short note with the date they need to know about isn't.
When to send it
For a routine request we'd wait three to five working days. Any sooner and it can read as if you didn't trust them to answer.
If you gave a deadline, follow up a day or two before it and mention the deadline again.
Sales and cold outreach are their own thing. Wait a week, maybe send one more a week or two after that, and then stop. Past two or three it starts to feel like a campaign.
After a meeting, send your own recap the same day. Then chase the open items on whatever dates you all agreed.
How to write it
Reply to your original email so the history sits right under your note. If you start a new thread with a new subject, they have to go digging, and digging is exactly what they didn't get round to the first time.
Then add something. A new fact, the attachment, a firmer date, or the ask cut down to one line. "Just checking in" doesn't count, because there's nothing in it to respond to.
Ask one thing. Ask two and you'll often get an answer to neither.
Make the answer cheap to give: yes or no, Tuesday or Thursday, this version or that one.
And give them a way out. Something like "If this isn't a priority right now, tell me and I'll close it on my side" works well on people who were stuck and didn't want to say so.
Four sentences is usually plenty. If yours runs longer, the first email probably did too.
Here's one we'd send:
Hi Maya, following up on Thursday's call. I've attached the two-page scope so you don't have to dig for it. Can you confirm by Friday that we're on for the 12th, or tell me what's in the way? If the timing's changed, a one-line reply is fine and I'll adjust.
A few common situations
After an interview or a pitch:
Thanks again for Tuesday. You mentioned you'd decide by the end of the month. Is there anything else I can send that would help?
When you need a document back:
Could you send the signed form by Thursday? I can't book the room without it. A photo of the signed page is fine if that's easier.
That last line does more than it looks like. People put forms off because finding a scanner is a chore.
For an unpaid invoice:
This invoice was due on the 3rd. I've attached a copy in case the first one got lost. Could you let me know when it'll be paid?
Attach the invoice every time, even if you sent it before.
For a colleague who owes you their part:
I'm sending the draft to the client on Friday at noon and I still need your section. Can you get it to me by Thursday evening, or tell me what's blocking it?
What we'd avoid
Sending the exact same text again. If it didn't work once, change something about it.
Copying their manager in to "help things along". Everyone can tell what that is, and it turns a reminder into an escalation.
Following up every day. Space them out, and decide before you start how many you'll send.
"Per my last email." You know what it means. So do they.
The real problem is remembering
Most follow-ups that go out late weren't held back on purpose. Somebody forgot. So decide when you send the first email, not later. Put it in your calendar, flag it, whatever you'll actually look at.
Plenty of mail apps will do this part for you. Superhuman says it brings a thread back if nobody replies by a time you pick, and SaneBox has reminders for messages that don't get a response. We haven't tested either for this page; that's how they describe it.
Otto does it too (it's our app, so weigh that). Set a follow-up on a thread and if a reply comes in, the reminder cancels itself. If nothing comes, the thread comes back to the top. You can also ask the assistant to set one for you. The snooze and follow-ups guide has the details.
When to stop
Two or three follow-ups over a few weeks, then let it go. We'd still send one last short note, so it isn't silence on your side as well:
I'll take this as a no for now. Happy to pick it up again whenever it suits you.
Oddly, that's often the one that gets a reply.
First published on the Otto Mail blog.
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