Email tips you don’t want to miss
Byron Patrick, CPA/CITP, CGMA, knows what he is talking about when it comes to technology — he co-authored FM’s popular 2019 article "100 Quick Technology Tips", which included ways to save time when using email. In this podcast episode, he shares more advice on how to use email effectively: what to do, what not to do, and why you should think twice before sending email.
What you’ll learn from this episode:
- How to properly begin an email and how not to.
- When and how to follow up on an email that needs a response.
- The link between this conversation and a 2019 podcast with Patrick that includes a discussion on the value of a well-placed emoji.
- The advantages and disadvantages of scheduling email.
- Why “recall” won’t always work if you want to undo a sent message.
Play the episode below or read the edited transcript:
To comment on this podcast or to suggest an idea for another podcast, contact Neil Amato, an FM magazine senior editor, at Neil.Amato@aicpa-cima.com.
Neil Amato: Joining me on the podcast today is a name that may be familiar — no, really should be familiar — to readers of FM. Our guest is Byron Patrick. Byron is director of presales and solutions at botkeeper in the US. Byron’s written several tech-related articles for FM that have been quite popular in fact. Today we’re talking about email. It’s kind of a sequel to a 2019 conversation we had on our sister channel, the Journal of Accountancy podcast. Byron, welcome back.
Byron Patrick: Ah, thanks so much, Neil.
Amato: So we’re diving in again, as I said, but as it’s the start of this conversation, we’ll kind of start with the start of an email. How do you start an email, or how should you start an email to someone?
Patrick: My personal approach has always been it depends on the audience. If it’s somebody that maybe you’re emailing for the first time or is just an acquaintance, a nice “Hello” is always good to start with. I don’t think anybody’s ever been offended by a “Hello” opening to an email. But, of course, if it’s colleagues or people that you work with on a regular basis, I think sometimes it’s OK just to start in with the message. There are definitely times where the subtleties and the extra “Hi, Neil” isn’t necessary, where you can just say, “Let’s find a time to schedule a meeting”, or something like that. I think it really depends a lot on the audience, but I do say, try to be friendly. Try to make it a warm landing so somebody’s going to be happy to see their name, and it’s not just “Neil, I need to talk to you.”
Amato: Yeah, that’s what I was going to say. So is there any wrong way to do it? So it may be “I need to talk to you now” as the only text in an email is probably not a good idea.
Patrick: I mean, unless your intent is to sound scary and unfriendly, then I would try to avoid that type of opening if you can.
Amato: So after you’ve sent an email, maybe you expected a reply in a certain amount of time. Maybe you specified needing a reply in a certain amount of time. If you don’t hear from someone and you want to follow up with a question asked in that email, what’s a good way to say it? Is it “Did you see my email?” Or do you simply forward what was already sent, or what?
Patrick: That’s another good one, and to back up a few steps even, I would first suggest that if you’re sending an email and it is time-sensitive, make that clear in the opening, even potentially in that first sentence, because that way at least if somebody just sees the preview of the message and they understand that it’s time-sensitive, the likelihood that you’re going to get a response back, even if that response is “Hey, I can’t get to this right now”, at least you have the answer. But let’s say even despite your best efforts to be proactive and include it in the opening or the subject, that the email has gone by a few days, what I tend to do is go back into my sent items, hit a Reply All to it, and just say, “Hey Neil, realised this probably got buried in your email. Just want to move it back to the top of your inbox, and let me know when you have an opportunity to review this or if you have additional questions before you can respond.” Something just friendly. Everybody’s inboxes are busy, and things do tend to get buried depending on people’s travel schedules and meeting schedules. So a nice little friendly “Moving this to the top of the inbox” I think is a nice approach. In a worst-case scenario, if it really is something super time-sensitive, and we’ve talked about this before, but there is this crazy device called a telephone that, you know, pick it up and give somebody a shout. Sometimes that’s all somebody needs. Say, “Hey, you know what, I’ve been meaning to get back to you,” so this is a great opportunity to just talk it through.
Amato: Yeah, that’s a great point, and you did reference that previous conversation. I’ll also make clear to listeners of this one that in the episode page for this discussion, we’ll link to that previous conversation so you can hear Byron’s thoughts on specific subject lines, emojis, and a wide variety of other things that we’re not covering today and have already covered.
Patrick: Nice. Great.
Amato: So where do you stand on the idea of scheduling emails? And what I mean by that is it’s Saturday afternoon, you’re not supposed to be thinking about work, but suddenly it hits you, “Oh my gosh, I was supposed to take care of that last week, and I really need to know first thing Monday morning.” But if you send the email over the weekend, can it get lost, or is it better to do what’s called scheduling an email and maybe send it out first thing Monday?
Patrick: Yeah, that’s a really interesting one, too, and there’s kind of a lot of different perspectives on that, and there’s a few considerations. Some people think about scheduling emails specifically about being considerate of people’s time and potentially not creating an interruption in the middle of the weekend when you should be doing other, personal things. And then there’s other aspects of it, too, what you somewhat alluded to, of maybe ensuring that that email is at the top of their inbox when they do sit down on Monday. All of them are very reasonable considerations when approaching it, and I personally go back and forth. There’s plenty of times when I’ve reserved maybe a day on the weekend to get caught up on emails, and it’s my time to just fire back, and especially if there are things that maybe don’t necessarily need a response, or any specific action, but are more or less just confirmations of things, then I’ll probably just fire them away and just hit send, let them go.
The ones where I want to ensure it hits somebody’s eyes as quickly as possible, that for me personally is where I use the scheduling. Because if I can schedule it to hit their inbox at 7:59am on Monday, I know that as soon as they open their email, that my name, that email message, is going to be at the top of the inbox before the spam that came in over the weekend, before everybody else’s messages. So you can accomplish that really easily. If you’re using Microsoft Outlook, there’s a little button within the options that says, “Delay Send”, and you can put in a specific time of when you want it to send, and it will sit in your outbox until that timeframe. If you use a Gmail platform, there’s also, right on the Send button, a little caret that you can click on where you can choose to schedule it for a later time, and again it will sit in a scheduled folder. So sometimes you want to go back and make an edit or maybe something has addressed the email, that send is no longer relevant, you can go back in and delete it. So there’s a few ways to accomplish it, and definitely some different approaches to it. But I’m a big fan of scheduling just to ensure that I am at the top of the inbox and the priority list.
Amato: Yeah, that’s a good point. I’m so glad you taught me how to schedule an email. I’ll be using that on at least my work email. Maybe even this coming Saturday I’ll forget something conveniently and be able to send an email. So, great. We’ve talked about scheduling, we’ve talked about how to start an email. We’re going to bounce around a little bit, ’cause that’s just how I like our conversations to go. They’re more fun that way when you don’t know what’s coming next.
Amato: How detailed should your email signature be, and can that signature actually help make your electronic communication more efficient?
Patrick: Absolutely. There are definitely opportunities to improve efficiency with respect to communication there. If you are a Microsoft Outlook user, I’m a big fan of creating multiple email signatures, depending on the audience. If I’m sending an email to you, Neil, for example, I know you have all of my contact information. You know how to hunt me down, so I can easily right-click on my formal email signature and boil it down to just “Thanks, Byron.” But in general, you want to make sure that you have at least the minimum methods of communication: phone number, email address, website. It’s amazing to me the number of email signatures that are missing a website. When I receive emails, especially from people that I’m not familiar with, one of the first things I want to do is go to their website, and it’s always frustrating when you have to kind of dig for that domain within their email signature to look it up.
So give me a click, and you may look back — there’s some tools out there, such as Bit.ly and a few others that’ll track click rates, and it’s amazing if you use a link like that in your signature to see how many people actually click that signature line. It’s super valuable to have there. So obviously making it easy for people to get a hold of you in different methods of contact. If you’re using one of those cool apps that allows people to schedule time with you, a link to “Click here to schedule a meeting with me” is always nice. And personally I love adding a little something extra, especially if you’ve had a recent recognition, and you want to share the press release, or you’ve written an article somewhere, or something that’s relevant that you want to put there that you think people should know about. It’s super helpful to throw that stuff in the signature and mix it up a little bit. When people see something different, their eyes get drawn to it. So take that opportunity to be a little bit different.
Amato: Yeah, that’s good. On the calendar link, I’ll never forget the first time I saw that in someone’s email when they said, “Schedule time with me. Click this link.” That was the coolest thing ’cause it eliminates that back and forth of “Oh, when are you available?” “Oh, well Tuesday, but only from 11am to —” you know, it totally cuts out that back and forth, and it’s really helpful. And I’m sure you have no articles whatsoever that you could share on your email signature. Yeah, sure.
Amato: So you’ve sent email to someone and then you’ve realised sending to that person was not your intent. I’ve heard of something called recalling email, but I don’t actually know what that is. Is that possible?
Patrick: It is possible with a whole bunch of asterisks. Again, to back up a little bit, let’s talk a little bit about some of the safeguards to try to prevent that from even happening, and then we can talk about what to do.
Patrick: So depending on your platform, there are tools out there that will actually introduce a delay in the sending of your email. So when you click “Send”, it will actually introduce a five- or ten-minute delay for you to be able to stop that email from going out before it actually sends. The specific utilities that do that, I’m actually drawing a blank on those utilities now, but we can certainly follow up, and you could include them in the notes. [Editor’s note: The feature in Outlook is achieved by creating an email rule delaying the send between one and 120 minutes.] So that’s one opportunity. The second that I do frequently, if it’s an email that there is any reason to think through whether or not hitting that “Send” button is right — the right people are there, the right messaging is there — I have no problem saving that to my drafts and giving myself some time to reflect on it before I hit “Send”. And then finally, if you have hit “Send” and for any variety of reasons decided you regret that “Send” button, within the Microsoft ecosystem, there’s definitely a recall functionality, the ability to recall a message, and it works [in some situations].
Amato: So it’s not a failsafe.
Patrick: It is definitely not a failsafe, and it depends on the receiver’s email system. So if you were to email something to me and request to recall, and it ends up in my Gmail inbox, you’re not going to able to recall that. That mechanism does not exist. However, if you are on a Microsoft Office 365 platform and I’m using Microsoft 365 or Microsoft Exchange, and you recall [the message], there’s a chance that it might get recalled, and the caveat is the fact that I haven’t opened it yet. If I’ve opened it, the recall’s going to fail. If I haven’t seen it, my eyes have not seen it yet, then there’s a good possibility that you will actually be able to capture that and recall that message. In Gmail, there is a functionality called “Unsend” where you can recall messages, but again it’s the same kind of caveat. If you send a message to someone who is an Office 365 user, that “Unsend” functionality isn’t going to mean anything to that system. So a lot of it really depends on the two different systems, if they’re talking to each other, if the messages have been read.
Best bet is to never find yourself in that situation, but if you do, there’s a few ways you can attempt. But they’re going to fall in that like 15% to 20% likelihood that you’ll actually be successful in that manner.
Amato: Right. So it seems the moral of that story is think clearly before you send an email. Reread, maybe even send to your drafts, give yourself a mental cooling-off period before you actually send what you wrote the first time.
Patrick: Yep, absolutely.
Amato: Kind of related, I think I know the answer, but I’m going to ask it anyway. Have you ever intended to forward someone’s comment to someone else and accidentally replied to it? [Laughs] And you’re like, “Wait! Did I actually send that back to them, my snide response?” And I assume there’s no way to recall that because you’ve already said it, but is there any way to safeguard making sure you know you’re forwarding something versus just replying and not knowing?
Patrick: So I will plead the Fifth on having ever done that. But if that’s any indication, yeah, sadly I have become victim of hitting that Reply button instead of the Forward, and it’s kind of the similar thing: Measure twice, cut once, especially in a circumstance where you want to ensure that only specific eyes are seeing that message. I highly encourage you to double, triple, quadruple check if you are hitting Forward or Reply, because like I said, the recall functionality is certainly hit and miss. Not to mention if you’ve done this by accident, you may not even realise until that individual has followed up with you to say, “I don’t think this was intended for me. Let’s talk.” So yeah, be very intentional, very specific, and again sometimes that little manual delay will kind of put you in the right, sound mind before you fire off something that, again, you might regret.
Amato: Very good, very good. What are the ethical considerations around using BCC, or blind carbon copy, on an email? Should you ever use a BCC?
Patrick: It’s kind of interesting to think about it. So here’s one example where frankly the BCC in my opinion is absolutely the ethical situation. So say you are sending an email to a large group of people, and you want to be sure that you are being respectful of everybody, and not sharing their contact information with everybody else on that list. The blind carbon copy is a great way to accomplish this. So you can put all of those email addresses in the blind carbon copy section of the email, send that email, and now the recipients don’t know who else has received this. So you are not sharing somebody else’s contact information with somebody that doesn’t necessarily want to end up on somebody else’s newsletter. So that is one example of the blind carbon copy where I would say using it is absolutely the ethical thing to do.
Now, I think your question is probably more along the lines of when you are including somebody on a message and hiding the fact that you are including those individuals on that message, and I do believe that there’s definitely some ethical considerations to consider there. For one, are you potentially violating any privacy requirements you may have within your business in adding this individual to that message? Two, are you potentially violating any type of internal policies with respect to maybe including a colleague on a message to your boss where this is really something that should not be shared with anybody beyond you and your supervisor or your boss? There are definitely some ethical considerations there.
That being said, I think there are times when you might BCC somebody simply so it’s an FYI in their inbox, and it’s not necessarily violating anything. The recipient of the original email would not have any concerns for that individual to be on it, but you’re simply just throwing them in a blind carbon copy to ensure that they’re in the loop without potentially just adding a lot more activity to an already busy email chain. So there’s a lot to consider there, and I think it’s certainly worth consideration every time you go to use the blind carbon copy functionality if it is ethical in that moment that you’re using it.
Amato: Yeah, there’s obviously a bunch of different scenarios. Sometimes it’s going to work, sometimes it’s probably not a good idea. So good take on that. How do you guard against taking the wrong tone in email?
Patrick: That’s a really interesting question, and we talked about in the last podcast that we recorded about emojis, which I think emojis are a really great way to reinforce intended tone within an email, obviously being considerate of the audience and who you are sending to. That’s number one. Number two, I’m a big fan of Grammarly, which is a third-party tool. It works with Office 365. It also works with Gmail and a number of other applications. It not only will review the things you write for grammar, but there’s a plug-in for your email which will also provide you feedback on your tone. So it’s really cool. Basically in the bottom right-hand corner of the email as you’re typing, a little face will pop up, and it can be everything from formal to fun to neutral to angry, and it will reinforce to you that this is what the tone of the email sounds like. Really super helpful, I think. A lot of people don’t necessarily realise their tone, and especially, as you know, tone is very difficult to translate within written text. This is a really cool use of some artificial intelligence actually to provide some feedback of what that tone is in the message. It’ll hopefully ensure consistency between what you’re trying to achieve and the actual outcome.
Amato: That’s great. I didn’t know that about Grammarly. Obviously, it sounds like a grammar tool, but it’s so much more.
Amato: Great conversation today. We’re going to go into what I call our lightning round. I’m going to have you react to common work phrases that involve email, and I’m hoping to get a short, first-thing-that-pops-into-your-head response on these things.
Patrick: This sounds dangerous.
Amato: So the first is you see the person at the coffeemaker and they say, “I owe you an email.”
Patrick: “Why don’t we talk about it right now?”
Amato: Great point. How about this one: “Did you see my email?”
Patrick: [Laughs] “Have you seen a reply from me?” [Laughter] You know what, though, in all fairness, because of just the busy nature of our lives, sometimes it’s like, “You know what, I did, and I owe you an email. My apologies.”
Amato: There you go. How about: “Oh, I haven’t been on my email yet today.”
Patrick: I mean, it’s plausible, so yeah, I’m not sure how to react. It would probably depend on the circumstance.
Amato: Quick side thought: Do you ever purposely close your email so that you can get stuff done?
Patrick: I rarely actually close it, but there’s definitely times where I put it in the background so that I can focus. The interruptions with an email can certainly derail effectiveness if I need to really buckle down and get something done.
Amato: Byron, thank you so much. This has been fun.
Patrick: Ah, always a pleasure. Always fun, and it always ends way too quickly. So thank you so much for having me.