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Have you considered making the question the first line?

I think I understand your reasoning. If you lead with the question, then write a bunch of stuff. When they finish reading and get to the end, they may have forgotten the initial question. I guess I have found in my professional experience that leading the with question is often more effective when talking to management. They're often quite busy and may skim the email to judge the importance.

I find that when they skim they are very likely to miss the question and I usually have to bug them a couple times. If I lead with the question and make it concise and direct, it is often answered very quickly. ;) Yes, this is filler text to share my opinion.

Yes, and perhaps I did this more when I was working in a big corporation (law/tech). But now that I'm running a startup, most of the time I'm chasing people down it's for business development.

In that context, the recipient doesn't have any need to email me back, and I'm trying to make sure they do. For internal emails, there's already pressure for the recipient to email back sometime-or-other, so it's a different challenge.

> * If there's a question for the person to answer, make sure it is the very last sentence in the email.

Oddly enough I do the exact opposite: Within reason, I try to make the question I want answered the very first sentence.

I hate expository emails. Just tell me what you’re looking for. If I need more detail I would hope the follow on text would provide it.

I use a framework I learned while taking a course on legal argumentation back in college. Turns out it works fairly well in longer emails (whenever a paragraph is needed). Write your question/conclusion at the beginning and end. Stick context, evidence, and analysis in the middle in that order.

You could literally use the same sentence first and last if you just really need to get the point across and don't have time to get creative.

Mind sharing the framework?

I believe they just did.

I often do both. Very rarely do people read carefully in a business context these days. I design my work emails to be easily skimmed and I often repeat myself in different ways. You can't assume people will understand you, you must seek to be understood. Even after all of that, people will fail to respond to important emails because everyone is just so Fin burnt out these days!

There's also a factor in how modern email clients display messages. Gmail, Apple mail, etc show the first few words of the text alongside/under the subject.

Am I more likely to open an email that says "[subject] Have you heard about how cloud services can reduce..." -or- "[subject] Does that time work for you?"

(Disclaimer: neither, please stop emailing me about your amazing cloud services and how it will save me money.)

Just to clarify, this article was not about sales emails, and the tips I offered above were likewise not about reaching out to people I'd never talked to before. They were about following up with people with whom I'd already had substantive conversations that indicated mutual interest.

I think the strategies — and etiquette — for cold outreach emails are totally different.

Sounds sensible. That way, I can read the rest of your email through the lens of what's being asked of me. It won't seem like a pile of facts being thrown at me, as you've already established why I should care. Academic papers do something similar.

Taken further, we could put the question in the subject line. The email body can then provide detail and finally re-state the question.

Subject: Ok to manually norble remaining flurbs?

Body: As you know, our flurb-norblement service is out of action until Friday next week, and our un-norbled flurbs are costing us double. Should I go ahead and manually norble our remaining un-norbled flurbs, or just wait until the service comes back on?

(I've omitted the informal 'Hi Alice' prefix, and formal 'Best regards, Bob' suffix, that seem to have become standard intra-office netiquette.)

I googled this approach, but it seems that most articles about writing emails, are just lazy clickbait 'list articles'.

On your last point, you might be interested in reading Never Split the Difference: Negotiating As If Your Life Depended On It.

The author would advise you to ask a negative question in your email such as "have you given up on this project?" People don't like to say no and it often motivates a reply.

https://blog.blackswanltd.com/the-edge/3-ways-to-make-no-wor...

Depends on the person. We're not all sheep, and I'd see through that and think "Fuck You". I might right click the email and select "create filter out of this..."

The problem with any systematic of getting someone's attention is that is is impersonal by nature (not tailored to the person).

As audiences get more sophisticated and used to technology, the sender needs to get more sophisticated.

In the early days of internet marketing there was this figure called "The Rich Jerk" who would sell a lot of stuff by insulting his prospects. "I'm smart and your dumb" "I is winner, you is loser" type of thing.

I doubt that would work so well nowadays, infact the same guy made a comeback with a more "I'll help you step by step" attitude. "I'm a changed man" ha ha!. Good marketing indeed.

But if he stuck to the Jerk approach when the world had got more sophisticated and spam-intolerant no one would probably be interested in that.

Indeed. The author of that advice has this in his bio:

> "CEO of ... a firm that solves business negotiation problems with hostage negotiation strategies".

The advice makes sense in many scenarios, just not marketing.

Shaming people into not being a lazy shit at work or some other negotiation scenario is a legit and effective strategy.

But with a cold/cool sales contact, it is not genuine. What idiot salesman would start a relationship in a way that casts the customer negatively?

I’ve been in positions where I have influenced spending in a vertical where it’s sometimes winner take all. CRM generated pitch emails come in all of the time designed to look like normal emails and use these approaches, angling to get a meeting. It’s obnoxious. Tell me what problem you’re going to solve and how you solve it. 80% of the time I don’t care, 20% I might take some action if it sounds compelling.

I can think of one person who rode the Rich Jerk shtick all the way to the highest office in the US. There is a large population of less than sophisticated individuals, even today.

> have you given up on this project?

This comes across as presumptive passive aggressive nagging.

It implies that you already know the answer, and are just poking for a response.

Personally, I’d try and avoid working with someone who used that tone.

In rare situations forcing the answer, even forcing a no, can be helpful.

* If it's a cold call, start by introducing yourself:

"Hi, my name is so-and-so. I am a [brief description of you, e.g. "student at X university", "resident of...", "software engineer working at..."]. I found you via ... I read your paper on ... and I had a question:

or something like that.

Never say, "I wonder if you could spare some time to answer a question?" Just ask it. If they can spare the time they'll answer, and if they can't, asking if they can won't change that.

On that topic people who go onto support channels on IRC and then ask if it’s ok to ask a question drive me crazy.

It’s a support channel, just ask.

They may have had bad experiences with asking questions before, it's not that unnormal for certain communities to have a culture around shaming newbies for asking questions. They feel like they have to ask to test the waters before jumping into it. I don't blame them.

I'm hesitant to agree with you because it happens so frequently. I'll admit that I've had my share of receiving newbie bashing.

More often than not, I feel like talking with those folks and explaining to them that they should just ask and not ask if they can ask it seems like they just don't recognize what they're doing. Thus, it's usually good to tell them they don't need to ask and to just ask now and in the future.

You enter a room.

To the left is a door that leads to Comcast Support.

To the right is a door to a freenode channel guarded by a man yelling, "DON'T ASK TO ASK! JUST ASK!!!"

Which direction, gentle newbie?

Edit: intensification

> * If you've been following up with someone for a while, start off an email with "I wanted to follow up with you on this one last time". This reminds the person that you've emailed several times before (and perhaps makes them feel guilty for not replying sooner) and lets them know the ball is completely in their court. I have found this to be very useful in kick-starting leads that went stale.

It depends on in how good faith your respondent is acting. If there is no social or other pressure, "one last time" can indicate to its recipient "you just have to ignore this, and the issue will go away."

I've found this to be more effective:

"I sent you this three days ago but haven't received a reply. Did you get it?"

It's very rare not to get a response to that. On those rare occasions I wait a week and then just say,

"Hello?"

(on top of a copy of all the previous correspondence of course).

I can't remember the last time that has failed to elicit some kind of response. Most of the time it's "Sorry for the long delay, I was out of town..."

That seems overly aggressive to me. Unless I absolutely had to, I would not respond to either of those follow ups.

Are these internal or external emails? I could see how it might be more appropriate with internal recipients.

For internal, as long as the sender was in the right, I'd be suitably ashamed. I try to keep inbox zero (after dozens of filters), so it means I've really messed up to get those mails (or had bad filters).

But yeah - if they're being out of line to begin with (and are ignoring my previous mails implying they should use appropriate channels) or external folks that are asking for special dispensations, yeah, that will get you less helpful responses, not more.

Unless I've very strong incentives to answer, I usually put people who dare sending me an email with only “Hello?” or “ping” in it in my “least urgency queue”, if not directly in my spam folder.

If you had good reasons to ignore their previous emails you should let them know.

The sender has forced themselves into my life, and I'm expected to spend my time to tell them that they're unwelcome?

If you work with the sender or if they are your friend, or otherwise are known to you - then yes. I'm obviously obviously not talking about replying to spammers here.

If you have good reasons to ignore them they probably already know them.

Depends, but I wouldn't want to work with someone who ignores my emails.

In my book, “Hello?” deserves no answer and I'm very fine with whoever sends that not willing to send me more emails.

The previous emails might deserve an answer I just haven't had the time to send yet, but for otherwise equally important emails, the one from the most annoying / disrespectful sender will be handled last, if ever.

That usually means the other guy is using the relationship management software that mass mails and waits for leads.

> I wanted to follow up with you on this one last time

This sounds rude to me, IMO. It's like a thinly veiled ultimatum–I find it interesting that you've gotten success from this, since it feels antagonistic to me.

It clearly declares the author’s intent to give up asking in the face of being ignored, without any specific insult or derogatory behavior. Either not replying is fine with the recipient or it isn’t. If it’s rude to say “I won’t bother you again if you don’t reply”, what behavior would you replace that with that clearly indicates the outcome of choosing not to reply?

I encounter this frequently at work, where people either care deeply that they be heard, or do not — but regardless are unreliable at replying when asked to be heard the first time. Including “here’s my next course of action if non-reply” permits them to remain silently without being rude if they wish to.

> If it’s rude to say “I won’t bother you again if you don’t reply”, what behavior would you replace that with that clearly indicates the outcome of choosing not to reply?

Not bothering me in the first place, or maybe taking a hint.

If I didn’t reply to your first or second emails, assume I don’t want to. A motivating example: the only people who have ever emailed me repeatedly and used language like, “one last time” are cold calling salespeople and recruiters. I do nothing when they initially reach out, but when they start using tactics like this I send them directly to spam. I get that they have to sing for their supper, but I won’t respond to synthetic overtures of familiarity or urgency.

I do not endorse the use of this method, or any other, in a sales scenario.

I never want a sender with whom I have a bona fide relationship (business or personal) to feel ignored. If they were expecting a response and didn't get one, maybe I failed to perceive that expectation. Or maybe a technical issue caused the request or my response to get lost. Or most likely, I meant to respond and forgot.

And with that in mind, I absolutely want people to follow up if they're getting radio silence from me - and I don't feel put off if the follow up is only "ping" or "poke" or "have you had a chance to think about this" or "I need to know by X because Y". Its not like its that hard to reply things like "thanks for info" or "sorry I can't make it" or "that's really in Elizabeth's bailiwick" or "I need to do some research and I'm planning to get back to you next week".

I have definitely sent reminder emails to people and have received a positive reply (eg, ah sorry your first message must have got directed to my spam, or thanks for reminding me)

People can be forgetful. Reminders don’t hurt