Taking the Straight Line: Part 1 E-Mail

Technology is an amazing thing, in many ways it has allowed us to become more productive and work from almost anywhere on the planet. It truly is enabling the human race, but as with all things too much of a good thing can be detrimental.

E-mail is one facet of technology that is not used correctly and I dare say abused. Research in the United States has found that an average employee spends around a quarter of their time on e-mail. This is a serious reduction in time efficiency that could otherwise be used to 'get things done'. Indeed, due to the high volumes of e-mails people send it is easy for many to make embarrassing mistakes that could be detrimental to their professional interactions.

The short of the matter is the vast majority of people do not know how to use e-mail correctly in either their business or personal lives. This article provides timeless (and platform agnostic) advice on how to better handle and use e-mail making your life more simple. 'Take the Straight Line' people!

Should I send an E-mail?

The answer to this is more often or not, no. Think of e-mail as the modern form of the written letter, would you send many of those a day? Let's think about this for a second, the only real time you send a written letter is when you want to make something 'official' or to maintain official written record. Everything else you would most likely handle via face to face conversation or the telephone. Now, don't get me wrong, I'm not saying that we cannot be a little more liberal with a new technological advancement. However, that is the problem. We have become so liberal with this technology that people do not even think twice about firing off 20+ e-mails a day to multiple recipients who in turn reply. The first question you must always ask yourself is 'should I send this as an e-mail?'. Here are some instances when you certainly shouldn't send an e-mail:

  1. It is an urgent issue: Do not send an e-mail for something that needs urgent attention, use the telephone or face to face communication.
  2. You are a spammer: Is the information you are sending of real value to all those you are sending it too or are you just trying to make yourself look busy? The fact you are actually sending all these e-mails out means you probably don't know what others find valuable and what they don't. Know one thing though, they won't find you a valuable asset to the workplace/friend circle.
  3. Should be a phone call: Don't have e-mail conversations, pick up the phone instead of having e-mail too and fro.
  4. It is negative: Never send a negative message or reprimand via e-mail, it will almost always be taken the wrong way and blow any situation out of proportion. Which leads to the next point;
  5. E-mail is forever: Only discuss public matters as e-mail is NEVER private. This includes confidential e-mail, personal information, reprimands etc. It can and most likely will come back to bite you and could even have serious legal ramifications. Remember that people often do store e-mail for many years and could use it at anytime against you and companies will also store emails on servers even after you delete it - which can be requested by a court of law.

There are alternatives to e-mail but probably the best two options are face to face conversation and over the phone. These methods need to be used far more often than they are today, indeed there has been a rapid decline in personal productivity in the last decade due to 'e-mail warriors' and the constant need to 'cover your arse' via e-mail. I'm always told that 'human interaction' is critical in business and yet I see true 'human interaction' declining rapidly over time and being replaced by 'e-mail interaction'.

The Correct Way to Send an E-mail

Although a simple technology, e-mail is an art form with decisions ranging from who to send it too, how to title it and what to write in the body. The usual e-mail application layout starts with the 'To' field, however, whom you are sending the note too should be the last item you enter for a couple of reasons that will be addressed below. So lets start on the subject line.

Captivating and Accurate Subjects

The subject line is critical as people use it to decide whether or not they will read the e-mail. In the ideal world everyone would only receive the right e-mails and would have plenty of time to deal with all their mails, unfortunately we don't yet live in that world and until then you need to ensure your subject line is spot on. The subject line needs to address an individuals concern or business issue. It should also aid them in knowing what you want from them i.e. FYI (for your information), NRN (no reply necessary) in this manner you avoid unnecessary responses and the recipient(s) are clear on your expectations.

It is important when forwarding mail to edit the subject line inline with the above. Don't get lazy.

Clear and Concise Message Body

It is important to write clearly and concisely and to try and limit an email to 4 lines or less, anything more is unlikely to be read and you should always proof read your email before sending. Be professional yet concise in your prose and use exclamation marks sparingly, using only one to convey excitement else it is considered emotional or immature.

It is important to realise though if you communicate with people from different cultures that they can speak and write differently. For example a high-context culture such as the Japanese, Arabs or Chinese all want to know you better before doing business with you. As such, their emails will tend to be more personal in their writing style. Those from low-context cultures such as Germany, US and Scandinavia will tend to get to the point very quickly. This leads to a point on humour, don't use it. Humour can easily be lost in translation and it is best to leave this out of e-mails unless you know the recipient(s) very well but take note of the 'E-mail is Forever' point above.

Don't Get Attached

I will be to the point on this subject, I do not believe in e-mail attachments. They take up more bandwidth and storage and a lot of files are still emailed around today for collaboration purposes, and this is certainly not the right way to collaborate. Use other methods for working on files together; SharePoint, Google Docs, Apples iCloud are just some examples. If you simply want to share a file then use a service such as SharePoint, Dropbox or Box to share a link that the recipients can use to open the file.

If for some reason you really must mail a file then limit yourself to only two attachments and ensure you give the attachments pertinent and recognizable names.

Signing Off

How many times have you seen an email signature where someone has their e-mail address in their signature? This doesn't make any sense since they just sent you an e-mail from their email address, so in short don't do it.

Limit a signature to a closing line, your name, job title and a phone number. For those of you that like to show the world your academic credentials, don't. People don't care, I have a Masters and a Ph.D and wouldn't dream of including it in my signature. In case you are still thinking of ignoring that tip, just bare in mind that people will actually laugh and joke about you behind your back, do you still want to proudly announce your Bachelor degree?

It is also important to set your e-mail client to not include your signature after your first reply, if your client doesn't have a setting for this, ensure you delete it. Including your signature every time creates unnecessary noise.

How or Who to Address an E-mail to?

You should always fill these fields in last, if for no other reason to avoid accidentally sending the e-mail until it is completely ready. This is the most critical part of any e-mail. The 'To' field is utilized for who you want the e-mail to be focused on and who you want to take action on the e-mail. The 'cc' field is for anyone else you feel should be 'in the know'. The whole world does not need to be in the know and very often once you conclude an e-mail thread with the key individuals you can forward the final outcome to those that are on a need to know basis as a 'FYI'. This affords them the courtesy of only seeing a single e-mail with final outcome.

How to Process E-mail

We have discussed how when you should and shouldn't write an e-mail. We have outlined out to write a good e-mail. But how do you deal with the barrage of e-mail you receive on a daily basis? This now becomes about 'Taking the Straight Line'.

You don't sit by your mailbox at home do you? So don't live in your e-mail client! If you set this clear boundary then people will learn that if they have something urgent to speak to you about then they need to call you. If you are truly scared that your boss cannot wait a few hours for your response then leverage technology, for example VIP's in iOS. You can set VIP people such as your boss to show up as an alert when they e-mail you but others will not display an alert. Set two times a day to check your e-mail, preferably first thing in the morning and just before leaving for home (other times may work for you) at all other times your e-mail alerts are off or your client is closed.

Once you have crossed this hurdle it is all about the processing. You should aim to empty your inbox at each of these two e-mail 'sittings'. To do this you need to read, process, reply, archive, delete, delegate/task. In short you need to read each mail and make a decision, is it garbage? If so you need to delete it straight away or set an e-mail rule so that you never see e-mail from that sender again. You are best setting 'server side' rules so that the e-mail is processed via these rules before being delivered to your client. Services such as GMail and FastMail allow for this and whilst it may take you a little longer to set a server side rule, it will pay you back in time later.

The next decision is whether to reply/delegate/task it as an example in Outlook you could create a task for yourself or assign to someone else based on an e-mail to take action. Once saved the other party will need to action the item or you will at an appropriate time, the main point is that e-mail is out of your inbox and has changed to an actionable item. This can also be handled via e-mail but it isn't quite as elegant. When it comes to replying, you need to take caution in using 'reply all' unless you really think everyone on the list needs to receive the e-mail.

The only remaining option is to archive an e-mail, and this should be approached with caution. Whilst it is easy to archive every e-mail you ever receive this is probably not the best course of action. Only retain those key e-mails that key decisions or information that need to be retained, if its something that contains useful information you may want for future reference then take notes. The archived e-mail should be stored in a decent storage repository such as SharePoint or as a PDF on your local machine. After the mail is archived correctly the inbox copy should be sent to your 'Archive' folder which is set to delete content older than 30 days. You can use a different timescale but I have found 30 days works well.

So lets summarize; you use only 3 folders starting with the inbox and from there you delete an e-mail into the trash or reply/delegate/task followed by archive into the 'archive' folder which has a 30 day wipe. On its way to the archive folder it goes via a task manager/task e-mail for action or to an official archive system for retention (only if it is critical for future retention).

How to Deal With E-Mail Idiots

There time will no doubt come when you need to deal with an 'E-Mail Idiot', either a spammer or an e-mail warrior. There are things you can do to protect yourself from these idiots.


Mentioned above, server side rules can be very effective at filtering out e-mails you never want to see again. Create yourself a 'blacklist' rule on the server and keep adding e-mail addresses as they come through. As a note for those 'Idiots' you still need to work with, one effective rule I have found is to send e-mails they send you where you are 'cc' straight to trash but to allow ones sent 'To' you to pass through. Don't be scared to miss things, 80% of e-mail really isn't that valuable.


If you use a service like FastMail then you can create multiple e-mail aliases that you can use to sign up online. For example, I have a yearly e-mail address set up that I use if I need to ever give out for marketing reasons. At the end of the year the alias is deleted and that e-mail address is no longer valid. It takes a little effort on your part, but this is a really effective way to curb the e-mail scum from abusing your core address. Google has something similar where you can use a '+' symbol after the first part of your mail address but before the @ symbol to create an alias. However, you cannot delete this alias, but you can work out who has abused your trust. For example david@gmail.com could be david+twitter@gmail.com for your Twitter registration address. If anyone other than Twitter sends you email to that address then you kow either Twitter has sold your information or they have had a security breach.

The key take away from this section is to treat the root cause! Do not use services like SaneBox (although Kudos to them) to treat your e-mail problems. You are only putting lipstick on a pig and locking yourself into monthly or yearly payments to keep the problem at bay. As soon as you stop paying them the 'SaneBlackhole' (a folder that removes all unwanted e-mail from view) will no longer work and you are back to square one!

Changing Mindsets

You now have the information to handle your e-mail correctly, but to make this sustainable you need to pass this knowledge on too others. The more this information proliferates the easier your life will become, but how can you do this?

Away Message

I have started setting an away message at work that has been described as curt or rude, I don't care. This is often the response you get to anything that is even slightly against the grain, humans don't like change but they will get used to it and hopefully even see the benefit. My away message goes something like this:

Thanks for your e-mail. I will be vacation until X date, and won't be checking my e-mail. When I return on X+1 I will delete all e-mail I received while I was gone that is not from my direct line management. Otherwise I, like you, spend a full day frantically reacting to what I meant to leave behind when I went on vacation and spend the last day(s) of my vacation dreading that that day is coming. I'm sure you know the feeling. SO, if you're receiving this message and it's urgent that you hear from me, please resend a new e-mail on X+1 date and I will gladly respond as soon as I can thereafter.

This is not only about dread and work load, the simple fact of the matter is 80% of the e-mail is garbage any way and will most likely be dealt with or not be relevant by your return. See 'Time Your E-Mails' below so you are not the person receiving the above message.


I have already mentioned that Attachments are a no no, you don't do it so don't accept it from anyone else. If someone sends you an e-mail call them up and ask them why. Educate them about why its bad and show them how they can avoid doing it. People are too scared to intervene but are happy to sit moaning about it all day. Man up and intervene, it is the only way things will change. You will most likely be surprised at the positive response that you will receive at your intervention.

Time Your E-Mails

There used to many guides on the internet about what was the optimal time to send an e-mail, now that we have moved into the era of many mobile devices I think it is almost impossible to predict when is the best time to mail someone, unless you know they have a rigid email checking schedule as this article recommends. If they do then send the e-mail as close to that time as possible so that your mail is at the top of the pile.

Another consideration with e-mail timing is whether the main recipient(s) are on vacation. If they are then send them the e-mail on their return. Client's like Outlook have functionality where you can set a send date, use it.


This article touches on the basics of e-mail and associated etiquette, it doesn't serve to give you detailed guidance of how to implement the various strategies in individual applications. Other articles will serve to do so and will be tagged with 'take the straight line'. I hope you found the above article interesting, helpful or thought provoking. The fact you are reading this article means you have a keen interest in getting e-mail right, don't ever give up doing so because no one else around you is. It takes a month to break a habit, the longer you handle your e-mail like a pro, the more people it will rub off on.

Disclaimer: I am a user of FastMail and the link here in is an affiliate link. We have all become too accustomed to 'free e-mail'. You pay for what you get, online services are no different. FastMail is a fantastic service and provides all the necessary tools you will need to make you an e-mail ninja.

Disclaimer 2: I am a paid user of SaneBox and their links are affiliate links. I will not be renewing my service which I had started as a trial experience for these articles. I have no bad words to say for this company and their service, however, I cannot support the use of their service as I feel it masks a problem that should be treated at root cause level. If you are someone that doesn't mind spending a lot of money masking a problem for convenience then go ahead. Just bare in mind that it will cost you between $84 and $432 per year (at current 2015 pricing), so would you rather treat the root cause or put that towards your car or mortgage? As someone that handles 300+ e-mails a day I can tell you hand on heart that you can too without paying for a service.

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