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10 Serious Email Tips

This is a transcript of 10 Serious Email Tips
Speaker Key:    PB: Phil Brown, DW: David Whelan

PB:  Hi, it's Phil Brown and I'm here with David Whelan, and today we're going to talk about ten serious email tips.

DW: Serious, not jokey ones. We're not going to get into things like how to be appropriate on email and proper etiquette and things. We are going to talk about some things that you probably should be thinking about. The first one we are going to start off with is to get a professional email address. You do not want to have emails going out from your firm that are from "", "", "bell" or "". You want your email address to reflect your firm, and so it is a bit of branding, but it is also a bit of professionalism. So the basic way to do that is to buy a domain name, or register a domain name, and it would be something like "" and then you would use that with your email system. You may host your own email system, your own email server, or you can use a remote one, and you can use Google.

Google Apps for business will give you Google Mail and the web, but also use your domain name. Zoho ( has a free email server for up to five users, so if you have a smaller solo practice you might be able to apply your domain name to that. That way, you have to run your own email servers, but you will at least look as though you are an actual business.

PB: And I was just going to say, with those domain names, you do not have to have a website behind it.

DW: Right.

PB: So you can have "", but you do not have to have the "" website. You can just use the domain for email.

DW: It gives people a bit of a sense that you are in it for the long haul, that you have made a commitment to your business.

PB: And the other thing I would say about that is, just from the fraud perspective, and this is just a small reminder, if you are getting an email from someone purporting to be retaining you from some large business, but their email domain is "", "" or "", they are not really emailing you from that large business.

DW: That's a good tip.

PB: And it is just something to watch for. Our second tip, consider using email software.

DW: What email software do you use?

PB: I am not going to tell. I use about six different email software. I use Outlook mostly.

DW: And I guess we should probably distinguish for everybody what we mean by email software. Is that the same as logging on to Google Mail or something through your web browser?

PB: No. The web-based stuff is different and you are really, kind of, just borrowing time on a server somewhere else.

DW: Right. The most common software that you will find in law firms is Microsoft's Outlook. It used to be confused with Outlook Express but hopefully, if you have finally gotten off Windows XP, you have also gotten off Outlook Express. Windows 10 does come with a mail application - it is terrible - so you really should look at something like Outlook, which will cost you a bit of money, or you can look at some free email programs like Mozilla's Thunderbird, by the makers of Firefox. There is another good one called Inky, which requires an account with Inky, but it runs multiple email accounts all within one system. These tools come with additional productivity benefits, where you can start to really manage your folders and manage your files in different ways. Export your emails on your computer and also have some sense that if you want to, you can have all of your emails stored on your computer rather than sitting on a server somewhere else.

PB: And speaking of storing those emails, we get to tip number 3, which I suppose you could characterize as using your inbox as a file cabinet.

DW: Absolutely. Keep everything in your inbox. You know, when you hit 20,000 emails in your inbox then you know you have really been practicing for a long time. There are pros and cons and, in fact, there are a lot of cons to using your inbox for all of your emails but, in some cases, it can be done.

PB: And one of the reasons, I suppose, it could be done is because of the search tools that are available now, so that you can nuance them and find just about anything anywhere on your computer.

DW: Right. It really comes down to how you are going to manage it. If you are storing all of your emails in your inbox, and we are not kidding when we say we have heard of lawyers with more than 10,000 emails in an inbox. If you have not done anything to them and they are really just sitting there in the order that they came in, that is not an effective way to manage your information. But if you are in something like Google Mail, Thunderbird or Outlook, and you are applying labels so that you can sort and filter your emails, or do things that are "folder-ish", then that can actually be a pretty effective way to manage all of your emails. Otherwise you would need to be looking at doing searches that are specific, that will do the filtering for you, or use folders, the good old folders. Most email applications still support folders.

PB: And as I would say, from a practice management perspective and the best practices method, it is probably not a great idea to have your inbox filled with every email you have ever received because it is so easy, in that environment, to miss an email. And it might be an email that you should have dealt with, that was time-sensitive, and you skipped over it because you had another 30 emails to deal with, and when you go back it gets lost in the mix.

DW: It could be hard and, I guess, if you have something happen to you, it could be hard for people to come in and look at your inbox and figure out what is going on.

PB: Again, that is the other thing, I suppose, is if you have to go back and build a trail, or if there is some sort of a contingency plan that activates because you have been hit by a car, they may not be able to use that desktop search function that you have relied upon for all that time.

DW: Okay, tip number 4, we all love robots, so how much of my email can I automate?

PB: That is a good question, and it is probably a good idea to have an auto-response that says things like, "Thanks for your email, I have received it, I will respond to your email within 24 hours". It might not be such a good idea to have the auto address function enabled, so that as you start to type in an address to a client it automatically gets filled in.

DW: There are some really good productivity tools, and most email clients (whether you are on the web or you have software like Outlook on your computer), at any time you use automation you should really think about what they are doing. I think the one about notifying the clients makes so much sense it should almost be like a permanent "out of office", but you will not actually be out of the office permanently. Letting people know what the expectations are about communication are great, but so many people have gone awry when they have used other tools like the address functionality or other things that are auto-inserted or auto-addressed. You can even get into problems where emails come in that you auto-filter into a folder, and because they are not in your inbox you forget that they have come in and you do not go and check that folder. You could miss a deadline or something like that.

PB: Yes, the auto-address thing, for me, is something I turn off immediately because it is probably one of the biggest sources of sending emails off to people you never intended them to receive.

DW: This is an extra tip for the Outlook folks. There are two different types of auto-address features in Outlook. One is where it guesses and tries to put in the best one, based on your typing, and then there is another one where it will essentially ask you whether this is the right one. You will want to turn off the first and you can, potentially, keep the second, but you may want to think about not doing your addressing of emails until you have actually finished the email and so you can really concentrate on the name of the person who is going in that email.

PB: And I would say, for tip number 5, you should consider using encryption in your emails.

DW: Yes, that is a tricky one, isn't it, because when you are on the web, typically when you are communicating with the email site, like Google Mail, that traffic is encrypted, but when you send the email it is not encrypted after that, is it?

PB: No and one of the problems, I guess, that could come up quite frequently is that there has to be a key exchange with you and whoever you are sending that email with, so that they are able to decrypt on their end, and you will find some clients just do not want to deal with that. They do not want to take the time to secret squirrel your email when they receive it. But there are clients, on the other hand, who want to make sure everything is encrypted. Documents are encrypted and, of course, clients who will not even consider using email.

DW: Right. Is there a reason that you want to encrypt the everyday emails?

PB: I don't think so, but I think it is getting so much easier now, with emails. You used to have to cut and paste them and generate random numbers and letters, and now there are a number of different encrypted emails available. I just think that if you want to keep an eye on confidentiality, it is not a bad thing to consider. I am not suggesting it is mandatory, by any stretch, or that people should use it with all of their emails but keeping things with another layer of security is not a bad idea.

DW: Google is working on end-to-end encryption for its email and I think when it finalizes that and it comes out we will probably see encryption made available through lots of other clients who are trying to keep up with that.

PB: The use of web form emails as a point of first contact for clients.

DW: Yes, so imagine going to your law firm website and a client wants to reach out and talk to you, do you give them your email address or do you give them a form that they can fill out?

PB: The danger of having your email address on your website, for a first point of contact, is that people can send you all sorts of things and attachments and they can make attempts to create some sort of solicitor-client relationship by sending you confidential information and things like that. I think it is a good idea to have those web forms (e.g. give me your name, give me your address, or where I can contact you), but they cannot send any attachments.

DW: It is a good idea, too, when you think about our tip number 7, which is what happens when you get emails from people who you do not know or are not expecting to get emails from, that have things in them that you, perhaps, should not open or should not click on, and so we are talking about phishing.

PB: And you can receive an email from an address that you know, and it could be something simple like what looks like an email fax from that person, with their address attached, but when you scroll over that email, and I would suggest people scroll over every attachment before they open it, and be very careful and not open an attachment you were not expecting to receive, because it may end up putting something on your computer that later encrypts everything on your drive and, possibly, in the Cloud, and holds you hostage.

DW: Lawyers in particular, I think, need to be exceptionally wary of, pretty much, every email that comes in. Even if it does not look suspicious, even if it looks like it is coming from a person you know and it has a file that you were expecting, I think you should still be very wary. There was a lawyer in Pennsylvania who thought he had been emailed a voice message, by his voice message system, and when he double-clicked on it to listen to it, it did encrypt his entire computer. So when you are getting email attachments, download them and scan them before you open them. When you have links that are in the emails, do not just click on them. If someone is saying to reset a password or go somewhere, then open up your web browser and go there through the web browser, but not by clicking on the link.

PB: And I probably get three or four emails a week from organizations that I am supposedly banking with, that I am not, telling me I have to reset my password and I have to give them some personal information or I will lose my ability to use that account which, of course, I do not have in the first place.

DW: Yes, they are getting smarter and smarter.

PB: And let's talk about disclaimer. Should you be using a disclaimer?

DW: Disclaimers are funny because on the one hand, they make a lot of sense that you would want to have a disclaimer, particularly for issues related to privilege and things like that, and if you are in an area of law where there are regulatory requirements for you to have a disclaimer, obviously, you should have one. But for the most part, because of where they are placed in an email, they are pretty useless. And unless you have a particular need for them, I would not bother to put a disclaimer on your email. Similarly, here at the Law Society, we have disclaimers in both English and French, just because of the amount of text that it involves. If you are only emailing with a person who speaks English, you probably do not need to have your disclaimer in both languages. So it is really about keeping your email nice and clean, keeping out what does not need to be in there and thinking about just having the information that is really useful.

So instead of a disclaimer, think about having a really good signature block, where you have your contact information, including your email address, so that if the email, as it invariably is, is ever printed off, all of the information about how to contact you is included in that. It is not just a name, it is not just part of your contact information, it is all the stuff that someone would need to get in touch with you.

PB: Sure and I don't think you are going to find lawyers or paralegals getting away from those disclaimer block signatures at the bottom of an email. I think they are here to stay. I am not aware of all that much litigation over them, but I would also refer people to the Rules of Professional Conduct , which deal with things like inadvertent disclosure and the email that is mistakenly sent to you which contains, potentially, all sorts of privileged information.

DW: So, really, what we need is a disclaimer that comes at the beginning of the email, and that has a little "okay" button before you can actually read the email.

PB: And that might not be a bad idea in the future either. Return receipts and recalling messages.

DW: Return receipts and recalls are one of my favourite things, mostly because I block them. A return receipt is something that an email server will send. You set it up with your account, mostly with Outlook, but you can do it with others, so that if I send a message to Phil and Phil opens it, I get a message back that says that Phil has received my email. The problem with return receipts is that they can be blocked, and so having it turned on does not necessarily mean that you are going to get any information about the emails that were sent.

PB: And I think, with recalls. If you are not in the same email system that the other person is using, the fact that you are trying to recall it might not actually do any good. It is more important to think, "Do I really want to send that message?" before you send it.

DW: That's right. It is better to think about it in advance before you send that email. Google has a feature on Google Mail that does something like a five minute pause, so that after you hit send, it is still somewhere in the system so that you can get it back. But the reality is, once it is out of the barn door, it is gone. With return receipts too, from your own perspective, you are probably better off blocking them, because you do not want to be sending back information from people who are emailing you that maybe creates a paper trail that you do not want to create, about when emails are being accessed.

PB: And our tenth email tip, and I am going to add an 11, but at 10 I just want to say, once you send that email you have to be aware that you have lost control of that email.

DW: Right, so do not put anything in there that you do not want other people to see. Maybe, in some cases, you do not want to put in anything that could be confidential, because once it has gone to the other person, and hopefully it is to the right person, they can forward it, share it, and do other things with it that you may not want them to do.

PB: It might be published. It might be part of evidence later. It could be passed on to someone that has unintended consequences. Especially be careful if you are sending off an email to a list server or something like that, because you really have to consider that once you push the send button on an email, it might turn up on the front page of the Globe.

DW: Not a good place for your law firm to be.

PB: No.

DW: So what is #11?

PB: When using emails, if you are going to attach something to an email, do not ever attach just regular Word documents or anything like that in the email because not only does it contain a ton of metadata, the other problem is they can now take that document and add or subtract various things in that email and then publish it as if it were their own.

DW: Right. So formats, what are better formats?

PB: PDF being one of the big ones. Locked down and metadata removed so that it is essentially, just an image of something.

DW: Good tip.

PB: That's it for our ten serious email tips. Thanks, David.

DW: Thanks, Phil. 

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