From text messages to emails, there’s no denying that digital correspondence plays a pivotal role in keeping up with all your employees and clients. However, as convenient as these newer, more tech-savvy forms of communication might be, small business owners also need to realize that there is still a place in the modern business world for traditional printed letters and handwritten notes. So, how do you take advantage of all these different types of writing? In episode #133, Gene Marks and Elizabeth Larkin along with special guest, Hannah Stacy, advise small business owners on how to effectively utilize each of the various writing formats so that they can make the most impact.

Executive Summary

2:13—Today’s Topic: When is It Appropriate to Send Your Client a Business Letter?

2:40—While the idea of writing a physical letter might seem antiquated, clients who are typically inundated with emails might take an written letter more seriously.

3:13—If you do choose to write a business letter, make sure you use a more formal tone. You should also have it reviewed for grammatical and spelling errors to make it as polished as possible. A printed letter is also a good alternative if your previous attempts to contact someone via email have failed.

4:40—Business owners should try to keep their messages short, direct and professional. Another additional benefit of sending a written letter is that it can serve as record of your communication further down the line.

5:29—To avoid sending any emails prematurely, take your time and think very carefully before you reply, particularly if your reply requires a very detailed answer.

5:46—When you receive an upsetting email, you may want to write a “hot letter” first. A hot letter allows you to channel all your emotions out into a message that never gets sent. After you’ve written one, then you can prepare your actual in a more composed state.

11:52—Once you’ve decided to send a letter to your clients, there are two strategies you can use to elicit a response: begin the letter with a “you” or “your” and close it with a call to action. These approaches establish a sense of directness and urgency.

12:33—LinkedIn messages are another more direct way to reach your clients as well.

13:24—For a more personal touch, try sending a handwritten note or postcard. Business owners can compose these by using services such as Thankbot. Thank you notes in particular can be very helpful in establishing a deeper connection with your clients.

Submit Your Question



Elizabeth: Welcome back to the Small Biz Ahead Podcast. This is Elizabeth Larkin from The Hartford, and I’m here with Gene Marks.

Gene: Hello, Elizabeth.

Elizabeth: Hello, Gene. Gene is from the Marks Group, which is a small business, and he’s our small business expert here at The Hartford. So after we hear from our sponsor, we’re gonna come back and talk about sending actual letters to people as a small business owner. Should you send a printed letter? Can you send it in an email? What’s the format you should use? Should you send angry letters to people, and so on and so on. So we’ll be right back with that topic after we hear from our sponsor.

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Question: When is It Appropriate to Send Your Client a Business Letter?

Elizabeth: So we’re joined today by Hannah Stacy, who is the editor of Small Biz Ahead. Welcome, Hannah.

Hannah: Thank you. I’m excited to be here.

Elizabeth: So Gene, I know you’re gonna have a lot of questions, because I’m sure you’ve written a lot of letters in your day. And we’ve just done a whole series on Small Biz Ahead about how to do proper communications as your small business owner. So take it away.

Gene: I will, and I do have a lot of questions for Hannah. Tell me, Hannah, what do you do as part of your job?

Hannah: So I work with Elizabeth, and I’m the managing editor of Small Biz Ahead, which is our blog. And basically I work with writers and I edit pieces, and I put up great content on our blogs.

Gene: Very cool. So are you like an English person by background, or business?

Hannah: Actually business marketing.

Gene: That’s great, okay. So you grew up writing now, so you know one or two things there is about writing. So, that’s great. I’m glad that you’re here because we have a lot to talk about when it comes to business communication. So, this guy writes in a question saying like, you know, apparently he was having an issue getting ahold of, it sounds like a customer or prospect and-

Elizabeth: So today’s question is from an anonymous small business owner, a financial advisor, and he or she writes, “I run a small financial advising business. If I’m having trouble getting in touch with a client, should I send them a business letter?”

Gene: So yeah, so I get a kick, first of all I get a kick when you people use the word letter, you know what I mean? Like, it’s 2018. But it’s a really good question. First of all, are letters relevant in 2018? Would you send, Hannah, a letter to a client or a prospect if you have a difficult time getting ahold of them?

Hannah: So I think it can sound really outdated and antiquated to be sending an actual letter in the mail.

Gene: Right.

Hannah: But a lot of small business owners and people in general, they have so many emails in their inbox every single day, and you can kinda get lost in them. So if you actually take the time, write it out, send it in the mail and get it to their actual mailbox, they might take it more seriously, they might read it all the way through.

Gene: Right.

Hannah: It just really depends. So I think that it’s really important to actually know how to write a business letter just in general. And you can also write it in an email.

Gene: Is there any differences between writing a letter and an email? Are there any different approaches that you would take?

Hannah: So I think the approach with writing a letter out, you would typically have someone review it. You could check for spelling errors, grammatical errors. A lot of the times when you’re writing an email and you’re just sending it out, you don’t have someone else looking at it. You’re writing it from your phone, typically.

Gene: Sure.

Hannah: It’s a little more formal when you’re doing a written business letter, rather than an email, it’s just more informal.

Gene: Yeah, I kinda feel like if you’re writing a letter, you can take the time to make it even a little bit longer. I don’t know, maybe it’s, ’cause you get a letter it’s like you think of it-

Elizabeth: You’ll read the whole thing.

Gene: Yeah, you kinda feel like, you’re gonna read the whole thing. With an email, I’ve always felt, and I could be wrong here so I’m interested in your thoughts on this, but I prefer emails short and sweet. I mean, if I get an email from anybody and there’s more than a paragraph in it, I start hazing over. And I think, yeah I think younger workers, and I think people today, I mean listen, our attention span is like 10 seconds long, so it’s hard to concentrate. Do you think emails should be shorter than letters? What are your thoughts on that?

Hannah: I think, well in the interest of the question, I think because he’s having trouble getting in touch with the person. If you’re sending multiple emails and you’re not getting a response, then sending a letter I think would be the next option and the best option, to actually have someone have something in writing and then feel like they need to respond.

Gene: Got it. All right, that’s fine. So do you have any thoughts on just communication in general, business communication, like some best practices or mistakes you think you should avoid?

Hannah: I think the best thing to do is to obviously keep it pretty short and sweet and direct. Keep it professional. You don’t want to be sending something sloppy. And also I think with having a written business letter and typing it out, it can really serve as a record, and I think that’s important as well in communication, between small business owners or between clients. Mistakes definitely would be sending an email too soon, like quickly replying and not really thinking things out.

Gene: Yeah. Have you ever done that?

Hannah: Yes.

Gene: And when you do that it’s like you just, you’re like, the minute you get this email that [inaudible] I’ll send out an email. Two seconds later I’m like, I shouldn’t have sent that. And then you’re dreading the reply.

Hannah: Yes.

Elizabeth: Oh god.

Gene: Yeah, right? You don’t even wanna see the reply to that email. So what have you learned from that? Do you just save as drafts, or do you-

Hannah: I think it depends on the type of email, too. So if I’m getting an email from someone who’s upset with me, I’ll want to take my time to respond to it. Or if I’m getting an email where I really need to think it through and have everything laid out, I’ll take my time. And I think that this kind of brings up another topic of angry responses and angry letters.

Gene: Yep.

Hannah: And I think this is definitely something that business owners need to know about, is if someone’s writing a letter to you and they’re angry, or if you’re receiving something from somebody and you’re angry about it, how do you respond?

Gene: Right.

Hannah: One of our writers wrote a number of articles for us on business letters, and she found this article about the unsent angry letter. It’s called a hot letter. So basically-

Elizabeth: It even has a name!

Hannah: Yes.

Gene: I like it, I like it.

Elizabeth: This is what all of Gene’s emails-

Gene: Yeah, yeah. [crosstalk] A lot of hot emails. So what was the conclusion from that?

Hannah: So the conclusion from that is that you should take the time to write out a letter, like actually pen to paper, write something out if you’re angry. Get all of that out, and then you can write an actual letter to this person, or an email to this person, having released all of that anger and really getting clear on what you wanna talk about and what you wanna say.

Gene: Yeah, I couldn’t agree with that more. I’ve had experience of writing … I would write an angry email and it never ends good.

Elizabeth: And you send it?

Gene: Yeah, and I’ll send it, and it’s never ended good. There’ve been times I’ve sent an email and other people are copied from my company, and then somebody will email me and say, “Oh geez, Gene, I can’t wait to see what that …” It just never seems to end well. And the sort of advice of like you get more with sugar, what is it? With honey than with …

Hannah: With salt or something?

Elizabeth: You attract more bees [crosstalk]

Gene: Then salt or something.

Hannah: Vinegar.

Gene: Yeah. It really does sort of, it kinda leads you to agree that that’s the best way to go.

Elizabeth: So would you ever consider, maybe, when you’re angry about something, instead of tapping it out immediately, an email, would you consider actually writing it out, taking the two fields, deleting the person in the two fields, saving it as a draft for yourself.

Gene: Yeah, I think it is, I’ve done that, and I’ve learned to do that. And I gotta tell ya, and Hannah, I don’t know if you see the same thing. If you write out that angry email and save it as a draft, and then you look at it a couple of hours later. ‘Cause by the way, everyone doesn’t have to be responded to immediately. You can take a deep breath. I gotta say 98% of the time you’re probably not gonna send that email when you look at it again, do you agree?

Hannah: Yes, I agree. And I think even in life too, it’s such a great way to have conversations with people and learn how to clearly communicate things.

Gene: Right. Yeah I agree with that. So I have a few other things I’ve learned when it comes to sending letters. Just this past week I had this incident with, it was American Airlines. So I’m a very frequent traveler with American Airlines. I’m a big fan of American Airlines, and I think they’re great, their flight crew is great. We have this problem whenever we come to Philadelphia, which is my home airport, we always seem to be waiting way too long at the gate. I mean this has happened dozens of times, and it drives me nuts.

Elizabeth: Why is that?

Gene: If I knew I would be able to do-

Elizabeth: Well it’s ’cause they don’t have staff there?

Gene: I don’t know. It’s just like a management issue and it just seems to only happen at Philly, at least the most frequently. And it was just this past Friday night and we were waiting at the gate, it was more than 30 minutes, and it was 11:30 at night on a Friday. You can imagine. People wanna make connections, it just wasn’t great. And the pilot was apologizing, it wasn’t his fault, he was trying to get ahold of operations and they couldn’t find anybody to operate the jetway. And people were pretty irate, so irate that when we got off the plane, there were two American Airlines sort of official people there, like in suits. They seemed like management level. I had to wait in line to complain to them. There were people there that were yelling at these people, and then I wanted to also say my piece as well. I had to wait an extra few minutes until they … Can you imagine that job?

But anyway, so we’re talking about letter writing or email writing. So I rarely write letters, but emails I do, right? And here’s what I learned. If you’re a small business owner and you’re just not getting the attention from a large company, you go right to the top. I mean, I go right on LinkedIn and I got the CEO of American Airlines, and then I went to their website and got their whole management team. I figured out what their email addresses is, you can do that by Googling around a lot. And I sent an email to the CEO and the four executive vice presidents or whatever. But to your point, Hannah, it was a professional email.

Elizabeth: You didn’t send it at like, de-boarding the plane, you waited?

Gene: No, the next morning. I took the next, right? So [inaudible] was that you wait before you send those communications, right?

Hannah: Yeah. Cool off a little bit.

Gene: Yeah, you cool off. And I took a deep breath and I sent it the next morning. And it was like, listen, I’m a big fan, a frequent flyer, all that kind of stuff. But this is brutal, and can you please bring it to the attention of local management guys. This just has to be addressed, or something like that. An hour later I got a call from the VP of operations at the Philadelphia airport, it was pretty amazing. And then we wound up texting each other. He made the mistake of calling me from his cell phone, so now I have that cell phone number.

Hannah: And you’ll text him later.

Gene: I feel sorry for this guy now. But anyway, so we’re texting back. I had no desire to talk with him, I just wanted to bring it to his attention. But it’s just, it was a short and sweet email, so you don’t have it too long, you go right to the top and you keep it professional and nice. And you know what the other thing I always thought of, and I know I’m talking too much, Hannah, and I’m sorry. But if somebody sends you an email, it’s to make you aware of an issue, and you might not be aware of it. So I put myself in their shoes, like these people are just doing their jobs, they wanna, they don’t like this stuff happening. So how can I just make them aware? As long as I know that they’re aware and they’re working on it, that’s all I needed to know. I mean, I trust that they’ll figure it out, do you know what I mean?

Hannah: Right.

Gene: So, I don’t know. Getting back to writing letters versus emails, it’s just important. Now, I wanna get back to this guy’s original question, because he does say, “I’m having trouble getting in touch with a client. Should I send them a business letter?” Is there, Hannah, in your opinion, a better form of communication? Is there a preferred form of communication to you? A letter, an email, a text message? What is your thoughts?

Hannah: I think it depends on the relationship as well, but I feel like if you’re emailing them and you’re not getting a response, sending a letter would be a great way to get a response. And then including in that letter, in the very beginning, like a ‘you’ and ‘your’, so they’re like okay this is about me and I need to do something about it.

Gene: Good.

Hannah: And then just keeping it short and sweet. And really just maybe having a call to action at the bottom, call me at this number, email me at this number to get in touch with me or followup, and just really get their attention that way.

Gene: That’s great.

Elizabeth: But if you wanna get in touch with Hannah, a text message is probably best.

Hannah: Yes.

Elizabeth: Hannah’s young, so.

Gene: Text messaging is another option. I’ll tell ya another thing when you talk about getting in touch with their customers, I’ve found LinkedIn to be a really good way. For some reason LinkedIn emails don’t get popped into spam folders or people use a different email address there. So sometimes even if I’m not connected to somebody on LinkedIn, like say this person isn’t connected to his or her customer, if you go on LinkedIn and just ask for a connection, but then they give you the ability to write a note when you request the connection. So there you, hey I’ve been trying to get ahold of you, that kind of thing. That’s worked.

Hannah: And that’s, so when you send an email too, it’s like all the emails in the inbox you kind of go down. But in LinkedIn, if you login, I’m sure there’s gonna be less messages-

Gene: That’s right.

Hannah: So you might be able to get their attention.

Gene: And you can get their email from it as well, like when you’re set up. So, and for some reason they seem to get through the spam filters. So there’s a lot of different ways, I think, to do that. Now I have actually made a note, because we use this, I have this bookmarked. There’s a site called It’s, I guess we’ll put that in the show notes. And we’ve used that in the past to send, it’s a handwritten, it’s not my handwriting, it’s some computer’s handwriting, but you can send a handwritten note to somebody. And it’s just a touch, you know what I mean?

Hannah: That’s cool.

Elizabeth: When do you use that?

Gene: Great question. We usually use it if, in this situation that this person’s having. Like if I’m trying to get ahold of a prospect, it drives me nuts. I’m trying to sell them a system and we spent all this time, we’ve whatever, and then they go dark, they’re not even responding to my emails. I’m like, what’s going on? So as part of the, okay they’re not responding to my emails. I don’t think I’d sit down and write a letter, but I would, I send something on Thankbot, and it’s just a short little note-

Elizabeth: Wait, explain to us what Thankbot does.

Gene: Sure. So what Thankbot is is you go to the site, I forget how much it costs, like $2 or $5 each time, so there’s a cost to it. But then you type out your letter, you know. Sometimes the same email that I’m sending, but I just put … And what it does is it puts a little postcard together, in a handwritten postcard, like a computer-generated handwriting.

Elizabeth: Oh that’s cool.

Gene: And then it puts it in an envelope with a stamp, and puts it in the mail.

Hannah: That’s really cool.

Gene: So, you know what I mean? So it’s kinda midway between a personal handwritten note and an email, if you know what I’m saying. But they do physically get it in the mail. And it’s just a touch, you know, and maybe that’s the thing that gets their attention. For all you know your email’s getting caught in a spam filter or something like that, you just don’t know.

Elizabeth: I think a lot of times in business when a client doesn’t respond to you, they honestly just, they don’t know what they wanna do next so they just don’t wanna respond.

Gene: Which annoys me to no end, ’cause it’s like fine, then just tell me. If you’re on hold, just quick, “Hey, Gene, we’re on hold, can you check back in a couple months,” is all I wanna know, rather than not getting any response at all. Now the other thing I can also say is, what are your opinions, we’re talking about writing and business correspondence, Hannah, what are your thoughts on thank you notes to customers?

Hannah: I think those are really important, and I think it can really strengthen your relationship too, that you actually take the time to write something thoughtful out and send it to them, rather than maybe a quick text or an email. And they get it in the mail and they can keep it, and they can refer to it.

Gene: I agree. Yeah, I agree. Isn’t that funny? It always strikes me, I’ve gotten a couple thank you notes for I don’t know, whatever, something that we’ve done or whatever, and sometimes we get it from people you wouldn’t expect to get it from, like somebody from a PR firm. But it was a younger person who you’d be like, I’m surprised this person even knows how to write, you know what I mean? And then writing a nice handwritten note. And I’m not doing that, and that’s why I thought wow, that was a real nice thing to do.

Elizabeth: Yeah, but you’re Thankbotting, so.

Gene: Yeah, I’m Thankbotting, but this was like actually, this person actually took a card and hand wrote out a note and put it in the envelope and put my name on it and I get that. And I think that’s a nice, that’s kind of a cool thing to do.

Hannah: A nice touch.

Gene: So, Hannah, as you wrap things up, what final thoughts or recommendations do you have for a small business owner sending business correspondence?

Hannah: So I’d recommend that business owners just take the high road, they remain positive. They keep their communications short and sweet, to the point, and if you’re not getting a response through email, you can always send a business letter in the actual mail.

Gene: Yeah, that’s great. Yeah there’s no one silver bullet for communications as long as you do it professionally. Well, that’s great. Elizabeth, any final words?

Elizabeth: I was thinking, while Hannah was talking, that if I were ignoring someone’s emails and then I got an actual letter from them, and it was very professional and well written and everything, I would feel so bad, and I would immediately start responding to their emails, ’cause I’d be thinking, God I don’t wanna print a letter out back to them.

Gene: That’s you, and you actually have a soul.

Elizabeth: I also think that sometimes a letter is just gonna get you more, because having a physical piece of paper in front of you, that just means so much more than someone clogging up your inbox. If you’re afraid to write a letter, if you’re thinking god, I don’t wanna write a letter, we have a whole guide on Small Biz Ahead that we published earlier in the year that really takes you through the entire process. It even gives you a format. I think we have examples of what you can say.

Hannah: We do.

Elizabeth: So we’ve really got you covered. So we will link to all of those in show notes. So if you have a difficult client or a new client and you wanna make a good impression on, or you wanna send out a mass communication to all your customers, come to one of these links and we have you covered for everything that you would wanna send, a hard copy letter.

Gene: Cool.

Elizabeth: All right, and we’ll be back with our next episode in a couple days. Thanks for listening.

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