How to ask for anything on the internet

For the last four years or so, I've worked on teams that were either partly or completely distributed all or some of the time. In that sort of team, you do a lot of asking people for things and being asked for things over the internet: IM, Skype, email, etc.

The internet adds a few obstacles to asking people for things in a constructive manner that you don't necessarily encounter if you're asking for something face-to-face. You lack body language and other non-verbal queues, and it's harder to grasp tone from a written, digital communication. Most people are also more rushed in communciating their ideas in writing than they would be if you were sitting across the table from them.

Asking for things over the internet has some benefits too: you get a written record of what was asked for that you can refer to, there's less risk of mishearing a request, it's much easier to loop someone else into a conversation, etc.

Regardless of the advantages and disadvantages of internet communciation in general, assuming you are asking people for things via the internet, asking the "right" way has at least two clear benefits:

1. The selfish reason: people are more likely to actually do what you ask for if you ask them properly. You can do your job better if you ask for things in a constructive manner.
2. The human reason: asking people for things the "right" way is almost always friendlier and more polite, which is the "human" thing to do. Other people will view you as a better person if you ask for things in a constructive manner.

While each medium (email, IM, etc.) has its own nuance, there are some common things that are always true about asking for something:

• Front load the communication with context, specifics, and the underlying problem you're trying to solve.
• Always provide your desired and required timelines.
• Always thank the recipient.

Pick your poison for more:

• Email
• Instant Message (IM)

Email

Most people get a lot of email. I don't feel like I get an especially large amount of email, but even I've averaged over 50 emails/day for the last eight years, including weekends and holidays and excluding spam/junk mail. If you work on a remote team, email or some email derivative (like a project management tool) is probably the primary way you ask people for things.

Two example emails follow. Which one do you like more?

From: Jack Sparrow Subject: help Hey jane- Can you send some info about widget handling and queue times? Jack

From: Jack Sparrow Subject: Can you help me analyze where bottlenecks in widget production are? Hi Jane- I was hoping you might be able to help me out -- I am trying to understand where bottlenecks currently are in our widget production and develop some ideas to improve those bottlenecks. This is important because our benchmarks suggest we should be able to double or triple our widget production, which would get more inventory available for the sales team since customers have been clammering for these new widgets! Frank thought you could help me because you've looked at this before for another project (he mention Operation Lodestone). Specifically, I was hoping you could help me with: A process chart showing the flow of a widget through the factory. I think I understand it from the notes I took at the last quarterly review, but I'm not positive. I'm attaching my notes in case you have a minute to take a peek and tell me if I'm off base. Handle times at each step of widget production. I don't think our handle times are far from what they should be, but I think it's worth double checking. Queue times and depths at each step of widget production. My guess is that this is where we're going to find problems -- we probably have huge queues at some steps and none at others. Results from our team survey about factory-floor ideas to improve widget production. I know the folks who work on this every day have some great ideas of simple things we can do to improve this. Any ideas you have about how we can better identify and improve widget production. Would love to pick your brain over coffee or lunch if you have time in the next couple of weeks. If possible, it would be great if you had a chance to look at this by next Thursday. That way, I'll have time to get ready for a presentation to the board the following Tuesday. Thanks! Let me know if I can clarify anything about the specific things I'm looking for - happy to respond via email or find some time to talk live at your convenience. Jack

These aren't far exaggerated from emails that I receive on a regular basis. Jane almost certainly prefers the more detailed email, but let's look at what specifically makes it successful:

• Starts with an explanation of the root problem that you are trying to solve, not just the specific datapoints or things you're looking for.
• Explains why solving that root problem is important to the person who is receiving the email.
• Explains why the person receiving the email is relevant and the right person to help with this.
• Asks for specific things, with an explanation of why they're important / what you think they'll show.
• Tests your own understanding against that of the person you're emailing and seeks advice based on the recipient's expertise.
• Lays out a clear timetable and explains why that level of urgency is needed.
• Offers follow up at the recipient's request.
• It says thank you.

IM

There are two groups of people who I find myself IMing with every day. These aren't mutually exclusive groups, but I usually find that someone falls into one group or the other at any given time.

There are some people who I just chat with on and off all day about the weather, movies, cat pictures, etc. Never any time pressures or obligation to respond - we're just shooting the breeze. I have no advice or guidance for how to IM these people; presumably you have some sort of friendly relationship with them, and can communicate with them as friends do.

The other group of people are people I have more "transactional" conversations with - one of us wants something from the other one. Before IMing with one of these people, ask yourself if you really need an answer right this minute, or if it can wait a few hours. If it can wait, send an email.

Again, consider two sample conversations below.

(03:50:00 pm) them: ping (03:55:00 pm) them: ping (04:00:00 pm) them: ping (04:02:30 pm) me: hey, what's up? (04:04:00 pm) them: can i ask you a question? (04:05:10 pm) me: sure, how can i help you? (04:07:00 pm) them: i'm trying to find the sales totals for last quarter. (04:08:10 pm) them: do you have it? (04:08:30 pm) me: i can run the report for you. it'll take a couple of minutes. is this urgent? (04:10:37 pm) them: yes, very. (04:12:00 pm) me: i sent you the pdf by email. elapsed time: 22 minutes

(03:50:00 pm) them: hey, i'm getting ready for tomorrow morning's staff meeting and was trying to find the sales totals for last quarter. thought you might be able to run the report for me or tell me how to. not super critical if you can't get to it, just hoping to be able to bring the latest numbers so sue and john can review them. i sent you an email as well, just wanted to give you a heads up since it's a little short notice. thanks in advance! (03:54:12 pm) me: thanks for the heads up. replied to your email with the pdf. elapsed time: 4 minutes

Obviously the latter message is preferrable, but why?

• It lays out what you need from the very beginning, instead of a bunch of back and forth.
• It provides a timetable for when you need something by.
• It explains why something is needed, and what will happen if it doesn't get done.
• It includes an email follow up in case someone doesn't get the IM.
• It says thank you.

It is worth asking if this needed to be done via IM at all, or whether an email would have sufficed. IM is great if something is truly time sensitive, but a distraction if there's enough time to wait for the next time someone checks their email.

IMing strangers

Pretty simple way to IM someone as your first communciation: don't. If you haven't had email or in-person interaction with someone but somehow find their IM information, don't IM them. If you do, you should absolutely explain who you are and why you are IMing them as your very first message.