Converting this from a Facebook comment to LW Shortform.

A friend complains about recruiters who send repeated emails saying things like "just bumping this to the top of your inbox" when they have no right to be trying to prioritize their emails over everything else my friend might be receiving from friends, travel plans, etc. The truth is they're simply paid to spam.

Some discussion of repeated messaging behavior ensued. These are my thoughts:

I feel conflicted about repeatedly messaging people. All the following being factors in this conflict:

• Repeatedly messaging can be making yourself an asshole that gets through someone's unfortunate asshole filter.
• There's an angle from which repeatedly, manually messaging people is a costly signal bid that their response would be valuable to you. Admittedly this might not filter in the desired ways.
• I know that many people are in fact disorganized and lose emails or otherwise don't have systems for getting back to you such that failure to get back to you doesn't mean they didn't want to.
• There are other people have extremely good systems I'm always impressed by the super busy, super well-known people who get back to you reliably after three weeks. Systems. I don't always know where someone falls between "has no systems, relies on other people to message repeatedly" vs "has impeccable systems but due to volume of emails will take two weeks."
• The overall incentives are such that most people probably shouldn't generally reveal which they are.
• Sometimes the only way to get things done is to bug people. And I hate it. I hate nagging, but given other people's unreliability, it's either you bugging them or a good chance of not getting some important thing.
• A wise, well-respected, business-experienced rationalist told me many years ago that if you want something from someone you, you should just email them every day until they do it. It feels like this is the wisdom of the business world. Yet . . .
• Sometimes I sign up for a free trial of an enterprise product and, my god, if you give them your email after having expressed the tiniest interest, they will keep emailing you forever with escalatingly attention-grabby and entitled subject titles. (Like recruiters but much worse.) If I was being smart, I'd have a system which filters those emails, but I don't, and so they are annoying. I don't want to pattern match to that kind that of behavior.
• Sometimes I think I won't pattern match to that kind of spam because I'm different and my message is different, but then the rest of the LW team cautions me that such differences are in my mind but not necessarily the recipient tho whom I'm annoying.
• I suspect as a whole they lean too far in the direction of avoiding being assholes while at the risk of not getting things done while I'm biased in the reverse direction. I suspect this comes from my previous most recent work experience being in the "business world" where ruthless, selfish, asshole norms prevail. It may be I dial it back from that but still end up seeming brazen to people with less immersion in that world; probably, overall, cultural priors and individual differences heavily shape how messaging behavior is interpreted.

So it's hard. I try to judge on a case by case basis, but I'm usually erring in one direction or another with a fear in one direction or the other.

A heuristic I heard in this space is to message repeatedly but with an exponential delay factor each time you don't get a response, e.g. message again after one week, if you don't get a reply, message again after another two weeks, then four weeks, etc. Eventually, you won't be bugging whoever it is.

Related:

• Discussion of whether paying people to be able to send them emails or paying if they reply can solving the various bid-for-attention problems involved with emails.