A small podcast to help you become a better business owner

Season 2, Episode 1

Communicating with Your Clients


We’re chatting all forms of client communication / account management this week, how to get better at it and make it less awkward — even enjoyable — for everyone involved.


We’re chatting all forms of client communication / account management this week, how to get better at it and make it less awkward — even enjoyable — for everyone involved.

Links Mentioned


  • Margaret Reffell
  • Kai Davis
  • Reuven Lerner


Each episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they’re enjoying and recommend you check out:

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If you’re a freelancer, then you’re not just an expert in your field. You’re also a business owner, responsible for everything from bookkeeping to marketing to customer satisfaction to business development.

On the Business of Freelancing, our panel of experienced freelancers discuss the issues that they have encountered while building up their business — and give you practical, actionable advice to take your career to the next level. We also invite expert guests to provide their opinions and perspectives on how you can better succeed in your freelance career.

Episode Transcript

Kai: Hello, and welcome to the Business of Freelancing podcast. Thanks for joining us today. On today’s episode, we’re going to be talking about client communication over text, video, or email, what you should know, and how to have a good time communicating with your clients.

On today’s episode of the Business of Freelancing, we have Marg.

Marg: Hi.

Kai: We have Reuven.

Reuven: Hi there.

Kai: And I’m Kai. So let’s talk a little bit about client communication. To kick off this conversation, I’m curious, how has your communication with clients evolved or changed over time? Reuven, do you want to start us off?

Reuven: So sure. So I’ve been doing this for a long time. So we began with clay tablets. Okay. Maybe not that long.


Reuven: Email has always been a pretty steady part of the communication, but, it’s always been mixed in with phone calls. So in the beginning back when I started, it would be mostly phone calls and then we’d maybe confirm things via email.

Now it’s pretty common for me to get email out of the blue from someone and believe and exchange some email back and forth what do I do? How do I do it? Then we’ll arrange to have a phone call after they’ve done. I guess they’ve done the sort of vetting of me and I’ve done the vetting of them. Then, okay, it’s worth setting up a call.

In Israel, everyone uses WhatsApp. That’s like very, very standard, and so it’s not uncommon. Just last week, I got a WhatsApp message from someone saying, “Hey, I heard your name. Can we set something up?” That’s not going to be a big company. That’s going to be like very small startups sort of thing, but still promising and useful.

What does not happen, and this has nothing to do with coronavirus and everything is in-person meetings to set things up. Very, very, very rarely will I have a company say, well before you come to do training, come, let’s meet for two hours to talk about it. I used to have people do that, either before doing training or we would do a consulting gig. That is just unheard of nowadays, thankfully.

Marg: I think mine followed a similar path in that it’s definitely 90-95% weighed in the email category. Then over time, I’ve almost seen these like microevolution, especially with COVID and everything as well. So, for example, a lot of the work, the introduction, the communication will be done via email in the beginning, and then client calls.

Phone calls have evolved into Zoom calls and then the evolution within Zoom calls themselves has been now I always ask the person, are we doing with, or without video? Because I need to know what I need to prepare in the background, what I need to prepare visually.

So it’s interesting because at the very… I feel like a micro-evolution at the very beginning when video calls started, it was always like, Oh, do I turn my camera on? I don’t know. There was almost this like awkwardness of you didn’t know if the other person would have that on. Now, I feel like it’s the norm, just straight up ask, are we doing a video call or is it audio-only? So I think that’s again, like a micro-evolution of something that’s become so mainstream. I’m also curious…

Reuven: I need to adopt that. I need to start asking people, are we doing video or not in advance?

Literally, like three hours ago, we had set to do a Skype conversation and I of course go with my video on and he has his video off and I was like, okay, well, what do I do now? Now in the end I had a screen sharing. So I guess I need to have my video on, but what do you know, just ask.

Marg: Yeah, who knows. I feel like if I leave it up to the client, they’re usually open enough to say like, “Oh no, I haven’t had my morning coffee yet.” Or whatever the case may be to have it or not. Yeah, I’ve definitely found that just asking has saved a lot of like little awkwardness at the beginning for sure.

Reuven: Yeah.

Marg: Yeah.

Kai: It’s similar for me, a complete agreement on the micro-evolution in video calls to it being, I don’t know, like consent-based is the phrase that keeps coming to mind, like, okay, what are the parameters for this call? Oh, it’s 30 minutes. It’s just audio. Great. Who’s preparing the agenda. It makes it easier to step into it rather than, Oh two people have their video on, I haven’t done my hair, but what are we talking about today? Let’s just refer it an hour and a half.

It’s important to ask the questions and just figure out what the scope of the meeting is, what preparation is needed.

Marg: Like you said, brevity is definitely become super valuable, especially when it’s almost socially acceptable to be like, look, I don’t want to take up too much of your time, and then just diving right in as opposed to a lot of small talks. That’s almost evolved to be like a considerate and not only socially acceptable but a considerate thing to do also at the beginning of the call.

Kai: Yeah. Completely agreed. For me, at least the increase in video calls folks have been doing over the past three, six, twelve months has helped people see like, Oh, there’s a bit of an additional cognitive load here. My body is like, Oh, I see a human, but it’s not the same thing as being in a room or talking on the phone, it stokes the brain fires in a different way.

You have three or four calls in a day, over a couple of days in a week suddenly it’s like, why am I so drained? Well, because you’re doing this thing, your body’s and quite used to it. It’s hitting from different angles, and suddenly it’s like, why am I burned out? Oh, it’s because I had nine video calls this week. Let’s figure out how to make it less taxing. For me, that often is let’s turn off the video. Let’s have a shorter call. Let’s have an agenda, just so it’s easy to jump in.

Reuven: I hadn’t really thought of that as cognitive load, but you’re probably right. I experienced this a ton because I’ve done it for years, but especially now I’m doing all my training online with either WebEx or Zoom. I have this, most of my students and most of the companies actually turn their video off and I beg them to keep it on because for my sake, then I can see everyone. I feel like I’m actually teaching in group as opposed to just talking to my screen, but I can understand that for them, this is new, this is difficult, this is annoying.

So they just all turn their cameras off and they can, I don’t know if they’re tuning in or not tuning in, some of the time, most of the time they are. But I hadn’t thought of that as being more relaxing for them that turning the camera on then is taxing, and, they want to reduce that load.

Kai: I don’t know about you guys, but whenever I turn my video off in a meeting my body, I never think I’m tense, but I suddenly just relax a little bit more. There’s something that’s just Oh, I’m on camera, I better be on camera. Then turning it off, it’s Oh, this is just a voice conversation or just a conversation now.

Marg: Yeah. I’m also really curious too. If there was any extrovert listeners if they could weigh in. But I also wonder too, if it is almost like an energetic drain because of being an introvert, potentially. I always wonder if, and I don’t know if Reuven, if you identify as more of an extrovert, I sense that Kai you’re probably like myself a bit more introverted, but if you identify as an extrovert, maybe that actually does give you energy to seeing people’s faces and being able to interact.

So that’s something that I’m actually really curious about. If it is the same sort of mental load on everyone, or if that’s maybe a differentiating factor too.

Reuven: Look, I’ve often made the analogy between doing training and being a standup comedian, or performing on stage that it’s this dance between you and the audience. So in Israel, people are very engaged, very interactive. Like they’ll tell you’re stupid. You’re wrong. They’re not stupid, but you’re telling me you’re wrong, and what are you talking to you about? That’s nonsense, and you’re over the US people are a little more reserved and in China, nothing like absolutely nothing.

So that has ironically prepared me in many ways to teach online where I have to, what I call, fill the room. I have to provide my own interactions. But it’s way easier, more fun, more interesting, and better for everyone, not just myself, selfishly, but for the participants, if they participate.

But they’re not there, they’re doing this once in a while, but some companies seem to do more online. I have done it for years, and those companies definitely have a corporate culture where it tends to be more successful in my experience. But yeah, if I tell a joke and either people laugh when I see it or falls flat and I see it either way the scene definitely contributes.

Kai: Yeah, you’re right, it gives you an audience. Otherwise, it’s at a meeting or training, whatever. It’s hard, just not seeing some face or not seeing some response. Suddenly it’s just going out into the void, at least in my experience where if you have images of just one or two people out of a dozen or two dozen or a hundred, you know who to focus on, you have a couple of faces to look at, to say Oh, is this point hitting where it should be? Or is it just falling?

Reuven: But again, by my time, it’s a cultural thing. It’s like not, they are bad, but like my time in China with their sort of culture of how things work in a classroom, has been excellent for me getting ready for this online training and truth be told for doing YouTube videos where there I have to worry, like preparing my online courses where I should pretend I’m talking to someone who’s energetic and there’s an audience there, even though there is definitely no audience there.

Marg: There is definite on the flip side of it, I would say there is an advantage to having when you’re doing client calls, especially one-on-one having them being able to see you and having you be able to see them. Because there’s so much, that’s unspoken in body language. Also if there’s something that you can see that maybe you’re explaining to them, that’s too technical. You can see the eyes glaze over when you start to lose them, which can be really good feedback for you to know and be able to redirect or pull yourself back in.

So I do feel like everything in life, it’s a balancing act of like how much you can take on without burning out. Because, like you were saying, Kai, definitely having three or four calls back to back by the end, you’re ultimately not doing the client any favors too, because if by the end of the fourth call, it’s like, you can’t really concentrate properly. I know that’s what I’m like, then it’s hard to really hone in on how you can best serve them for sure.

Kai: Maybe let’s talk about a different context for a couple of minutes. So we’ve talked about video so far. How do you guys approach client communication or communications with leads, prospects, whatever, when it comes to email instead of video and voice? Is it something you intentionally think about to the point of Oh, I want you to create templates for these scenarios or this is my follow-up strategy, or is it a bit more organic? Let’s respond in the way it’s needed at the time it’s needed.

Marg: For the most part, for me, it depends on the scenario. There’s definitely projects that are like big feature. They have lots of components going on to their business and it needs to be like a high touch situation. Then you can… There’s almost the ability to, you need to be able to suss out how involved in not only creating the project you are but in the project management too.

So there’s a ton that gets done over email, but I would also say that there’s this tipping point of when is email too much because maybe there’s too many people involved. Then at what point do you bring it over into a more of a project management software? That’s something that I often struggle with because my clients, a lot of the times are so used to email and they would prefer just to shoot emails back and forth, which is great, but it’s like to have everything organized, you have it at a glance.

I definitely do that on my end whether it’s in Google docs or a spreadsheet or Notion or something I got to. But, I always wonder, like at what point do you guys, keep going with email with clients versus when does it get too big also to bring over into a project management platform.

Kai: I’m slightly allergic to project management platforms. At least the multiplayer approach. I’m a Notion all the time. It’s so fun for me, but when it’s okay, let’s get the client to have the client’s team members in there suddenly it’s a bit too much overhead for me. So I’ll typically approach it as email primarily and first off.

So if there are a number of things to talk through, I might send over a short email and say, “Hey, here are three questions. I need your input on details included below.” But when those emails start to get too long, “Hey, there are seven things I need your input on, and three of them are huge decisions.” Then I’ll usually escalate or elevate it to a phone call or a video call.

“Hey, here’s an agenda. These are the things to talk through. Here’s some of the context with these conversations, and these are the decisions we need to reach, or at least start moving towards inhabit as, a group or one-on-one phone or video conversation just to talk through the bigger things.” That’s how I straddle it, email on one side calls on the other, no project management software, really in the middle. How about you Reuven?

Reuven: [laughs] So Kai, you earlier used the word strategy in conjunction with email. I would be hard-pressed to you think of any strategy that I employed? It’s basically, they email me, I emailed them. It’s basically a written version of a phone call or just me speaking. That is in many ways possible simply because I have one, maybe two points of contact at any given company, and we already have an established relationship typically, or if we don’t, then we get that up and running, and then it’s just emailing back and forth like what would the dates be for the training?

There’s no project the management software involved because there’s no project. We basically agree on what the scope of the training will be. Very typically they’ll call me up, we’ll have a phone meeting for an hour. As some companies, let’s talk about that we have very special needs and I listened to them for 5-15 minutes and say, aha, aha.

Then I say, you know I think this course would be perfect for you. They say, “Yes, how did you know?” So they’re very special needs served by my off the sale product. If you’re any of my clients listening to this, that is of course not true for you.


Reuven: In terms of email strategy, it’s just keep it going and try to schedule things. Because the sooner I can put something on my calendar and on their calendar, it’s not a done deal until they sign PO, and so forth, but it’s 95% there, basically once that’s done.

I will also add that it continues to astonish me that these major, Fortune 100 companies have one person, two people in charge of training. You email with them and you set updates and maybe there’s like some fancy software behind the scenes, and some of them are starting to do some invoicing stuff and purchase order stuff. But at the end of the day, it’s just good, solid communication with the people from those companies.

So, I tend to be very bad about responding to people on time, because I’m so overwhelmed with email and I’m trying to get better at it because someone actually called me out on it recently. I have a big client and she said, “I love working with you everything is great. But sometimes it takes you two to three weeks to get back to me, and I really need you to respond soon to this.” I realized, Ooh, she’s noticed that’s bad.

So, it’s nice to be informal and chat with people and so forth. But it still needs to happen and happen in a timely way so they won’t write you off.

Marg: Yeah, a hundred percent. I’m also curious what you guys, sort of boundaries are with, clients who want to text you. Because I know I’ve made mine pretty clear, we have a period of time during launch, when I am available to them during text also during reasonable hours. I had someone text me, at 12:30, after midnight, once. I was like, no, this isn’t going to fly.

So during, launch week, it’s okay. But I am pretty clear afterwards, that we don’t text. It’s my only sacred space that I have for my friends, and I need to keep it that way. I know I was talking to my friend, who’s a real estate agent and for her it’s complete opposite and has now informs me that I could never be a real estate agent.


Reuven: I can’t imagine telling people don’t. Again, typically like you can’t text you, that’s nothing in Israel, but it’s way, way more common. The assumptions everyone’s WhatsApp. To say to someone, I don’t want to get the messages from you. I think it would be taken very poorly. Sometimes people will say, I’m sorry to be disturbing you in this hour.

Just earlier today I sent a WhatsApp message to our electrician and plumber, confirming that he gotten my dang transfer and he was fine with that. I also got a message from one of my clients confirming that we’re on for next week with me. It’s super, super usual normal to do that.

I will add though that again because I’m doing training in certain hours of the day. I remember very well doing launches of products, of projects, of websites, and it’s crazy during that time. I did have clients who would then abuse the assumption of constant communication.

It was usually email, but sometimes they’d call me at all sorts of crazy hours. Like, “Hey, there’s a bug fix it.” So, putting limits there or putting limits on, maybe they can try to call you, but you’re going to will be off or you want to answer them, but they should understand, it’s not launch week, then I’ll get back to you tomorrow and they’ll just have to live with that. Easier said than done though I know.

Marg: Right. Interesting. I guess the flip side of that, and I’m curious what your policy is, Kai, I guess the flip side of that is I don’t allow anyone in my text messages, but I always have it inbox zero. So yeah, all the emails…

Reuven: I’m so impressed.


Reuven: I have several zeros in mine.

Marg: What I’m saying is there’s no reason for anyone to text me, because if they send an email that says urgent in the title, it’s most likely I’ll get back to them within an hour or two. So it’s unlikely that they would ever need to text me. So, Kai, I’m curious what your…

Kai: I’m right in the middle, honestly, between the two of you. Personally, I do not text with clients. My phone number is my phone number, nobody, you could have it’s a it’s private for me just because it’s more personal communications. The device I have closest to me most of the time. But that said there is this growing category of email or growing category of messages that should be text-based, and they’re kind of too short and too small for an email.

You don’t need four emails for me saying Oh, here’s a minor update on this thing or FYI logo needs to be tweaked. So it makes sense in this non-mail text-based ground. So I gravitated towards Slack, both as a personal and a colleague and a private communication channel. Since it’s on all the devices, it’s similar to WhatsApp in the sense of, Oh, we could do text conversations here, and at least with the projects and clients I work with, it’s a good middle ground.

So I don’t think it’s the perfect solution. I think I’ll probably gravitate towards something else that gives me, a secondary number or this is the app where the client communication happens. It just sits over there. Everything else is my space, but it’s an interesting one. We’re definitely switching towards more frequent, shorter text communication, being a norm, but the tool we’ve used for the last couple of decades, email. It’s more in that middle ground of Oh, this is a project update, this is larger, this is, five hundred to a thousand words. Nobody wants a thousand-word text message.

So I see it shifting more and more, but, now it’s very much a firm boundary for me. Once or twice I’ve had a client requested, Oh, this is a super convenient way for me to communicate, and I just say, it’s not for me. These are the ways I can communicate. Let’s not do something where I’m going to be flubbing around trying to figure it out. So let’s focus on email and an occasional voice call and Slack messages and negotiate into something that works for both parties. But it’s very much a firm boundary for me.

Reuven: I’m curious, Kai, does that mean that you set up a Slack channel for your clients? Like, how are they on Slack with you? Oh, really?

Kai: Yeah, most of the time. I only work with a small number of clients. It’s more larger ongoing projects. So with those, I’ll either have them invite me into their existing Slack organization if they have one or just spin up a channel in my business, Slack and, invite them as a guest to that one channel for the three-month project duration. “Here’s where we could talk.” But with some clients it’s honestly them saying, Oh, I don’t really grok Slack. It’s not my thing.

So of those, we just focus on email and the occasional voice or video calls. So switches back and forth, depending on where the client is more of a digital native, or digitally fluent. I had a coaching client recently, wonderful experience, but they just were not fluent or really in with Slack. They’re in a different sort of part of the world. So with that, we just switched to email and it worked really, really well, slight change to how we’re communicating and how frequently we’re emailing, but it worked fine. So it depends on the context, depends on the situation, and depends on the project.

Marg: My question for you guys is I try to do this as often as I remember, but when you guys have voice or video calls, do you send… This is a two-part question. Do you send an agenda before and or do you send a summary afterwards?

Kai: I always try to send an agenda before. I’m a big believer in the power of an agenda. An early business mentor said to me, and it made a huge impression. If you have an hour-long meeting, spend an hour working on the agenda, spend at least as much time as you’re going to spend in the meeting, crafting the agenda or crafting the points you’re going to talk through.

That served me really, really well. Just make sure if it’s an hour and a half meeting, Oh, we better make sure we have stuff to talk through. Let me think through. These different points and the decisions we want to reach or make, or just talk through. So it’s led to better meetings. I lean towards the value in setting a summary, but honestly most of the time I’m zonked after the meeting. I need to take 30 minutes or an hour just to sit and meditate and have a drink of water, or do something else, and by that time, sending that summary has skipped my mind.

But at the end of the meeting, I try to set aside 10 minutes and say, okay, before we wrap, let’s talk through the next actions we each have coming out of this. That works as a great parking lot since the client will say, Oh, I’m going to tackle these three things, you’re going to tackle this. I will say, Oh yeah, and I’m also tackling these two things. That just makes it easy for me to share the agenda afterwards, and that sort of access that summary. This is what we talked through. These were the decisions. This is who owns the next actions, and then we can move forward and start taking care of the work.

Marg: Yeah, a hundred percent on the next steps, because I feel like a lot of times calls you’re throwing so much information at clients or they’re making a lot of decisions inside the call that they get pretty exhausted afterwards, too. Especially if it’s something that they’re not an expert in like we’re talking to them in something that we’re an expert in. So it comes a little bit easier to us, it’s not as emotionally taxing, but for them having to pay attention and really wrap their head around what you’re talking about. Clients, I would say 80 to 90% of the time do not know the next steps, even though we’ve talked to them on the call.

So a hundred percent, I would suggest to listeners, if nothing else, definitely I’m onboard with next steps, the things that you’ve even just like here’s what’s next for me. Here’s what’s next for you. When we’re done this let’s circle back and see what the next steps are after that.

Reuven: Hearing the two of you, it makes me wonder how I’ve been in business and survived for so many years being so incredibly unorganized. Agendas, summaries, holy cow [laughs]. I do that for full means, but again, I think just it’s been the last number of years virtually all my meetings have been pre-obviously set agendas. Like, okay, we’re interested in talking about training for this group.

There’s not much to say other than just get into the meeting and maybe hear a little bit about it. Sometimes there’ll be some next steps, as an exercise for us to do, typically there’ll be, I’ll get back to them and say, which topics do we, or don’t we want to talk about, but it’s really pretty, pretty simple stuff.

However, you did remind me that I have this thing, which is completely and utterly unused on my website, that if people want to book an appointment with me on Calendly, they can do that. On that, it leads them through a bunch of questions, that are effectively an agenda. Quite frankly, the only people who have used this so far are people who click on it and try to set a meeting with me to learn about individual training.

So, I have ratcheted up the warnings on the Calendly for making clear this is not for individuals such that nowadays basically it’s useless to raise the question where I have it. But that at least is like theoretically an agenda of, okay, I need to know who you are, what you’re interested in, and why you’re interested in it.

But, yeah, it’s not nearly as complicated as a regular, like web project marketing project, anything like that.

Kai: I love that as a nice bit of optimization though, like anybody could take and apply for a Calendly meeting, just, setting that confirmation email they could send and saying, “Hey, thanks so much for booking this meeting. This is an initial call. We’re going to talk through these three questions and figure out if we could work together.” It’s very much a set at once and then forget about it.

People are going to receive this. You could follow up, the questions they’re exposed to prior to the meeting. It’s a nice bit of optimization just for better initial calls or better meetings overall.

Marg: I would also say what you mentioned Reuven, it brings up a really good point in that when you have, what you have is, which is ultimately like a productized service, you may not necessarily have to though. You said you don’t have the agenda before and summaries afterwards, but if you have a productized service that you’re ultimately selling to as a one to many, I don’t think that’s necessary, so that’s almost one of the bonuses, the plus side of productized services.

Whereas if you’re doing something that’s very customized to a person’s situation, you have to guide them through that process. But if you’ve got a package ready to go, then that’s a really good place to be and where you don’t have to do, like extensive summaries and that kind of stuff. If you have something that is set to go in a box, it is what it is. Then I feel like that’s a really great place to be.

Reuven: Yeah. I was just talking to my elder daughter about this. She’s in Miami now, she’s got lots of meetings and is complaining about them. I was like, “I don’t remember the last time I had a meeting.” I don’t know how I’ve gotten away with this, except if it’s a client saying, listen, we did talk because things are very good or things are very bad. But that’s not like an action item thing that we need to rethink our relationship.

The good news is that typically because we’ve had flowing communication open a lot of trust built between both sides, that whether it’s good or bad, I’ll come away from the bad stuff feeling awful, but at least like we don’t need to dance around it. We can have this meeting, we can talk about it and try to move forward.

Kai: I’m still stuck on you having a thousands of emails in your inbox.

Reuven: Okay. It’s not really thousands. I’m very proud of the fact that I’m now down to only 50 or 60.

Kai: Hell, yeah.

Marg: That seems doable.


Kai: A friend once complained about their inbox to me. I took a look and they no joke had 16,000 unread just in their inbox. And I’m like how?

Marg: At that point just delete them all and start over again.


Kai: Yeah, burn it with fire.

Marg: Email Debt Forgiveness. When is Email Debt Forgiveness Day? It’s in April. Isn’t it?

Kai: It’s every day.

Marg: It’s every day. Yeah.

Reuven: I’ve heard of email bankruptcy. I’d never heard of debt forgiveness. That’s fantastic.

Marg: Yeah, it was on an episode of Reply All, where they introduced Email Debt Forgiveness Day. It was like someday in April, where it was basically erase your entire inbox and you don’t have to apologize for it, and everyone just forgives each other and starts over.

Reuven: Whoa.

Marg: In theory, it seems like a beautiful thing.


Marg: I’m not sure exactly what the episode is, but we can probably link it if I can find it.

Kai: This zigs in the other direction towards sending more email, but I’ve continually been impressed at how impactful, just sending follow up emails is. If you shoot an email to somebody it’s Oh, they haven’t responded in a week or two weeks later, just sending a short follow-up, email checking in on this, or, “Hey, you want it to, get this to the top of your inbox.”

It almost always generates a reply for me, or at least moves the conversation towards “Oh, no, sorry. This is not what we’re looking for. No need to follow up again.” Or, “Hey, thanks so much. The building was literally on fire the past week. I appreciate you following up and let’s have that conversation.” But so often just saying “Oh, my standard operating procedure will be a week after I send an important email.”

If I haven’t gotten a reply yet, I’m going to send off a follow-up email from template or a custom written, whatever it might be, just nudge them forward, demonstrate you’re paying attention to the conversation.

Marg: Yeah, a hundred percent. It’s so funny. I actually have one client now who solely relies on my follow-up emails to get stuff done to a point where now it’s become a thing where… It’s funny because I know you were talking a little bit before about how sending one word or one line email just doesn’t seem to fit the medium, but now I’m so used to it. Because with this one client, it’s got to a point where the email gets lost. I know it’s lost for her if it’s been a few days.

So I literally just put the word bumping in the title and resend it back to her and she knows exactly what it is. It’s a pretty low effort method for me. Now, I don’t know if I’ve trained her for the positive or negative to become reliant on my follow-up emails, but yeah, a hundred percent, I would say that most of the time the client is not trying to ignore you. They’ve literally just lost your email, forgotten about it, or don’t have the capacity or bandwidth to go looking for it.

Kai: Yeah. Complete agreement for me, it’s really a kindness. It feels Oh God, I’m intruding. I’m being pushy, but it’s a kindness to send that short response, bump their thread. It’s Oh, I forgot about this. Thank you. You found my keys. You found this email for me.

Marg: Yeah, I have had… People have been…

Reuven: When I get those, I get really annoyed.

Marg: Really.

Reuven: Yeah, absolutely. It’s like I know about your email. I haven’t forgotten that now I have two to respond to, thanks a bunch you jerk, love you too.

Marg: Really?

Reuven: Yeah.

Marg: I’m learning so much about the individual dynamics and you literally have no idea anytime and it, how anything’s going to get received.

Reuven: I really hate it when people do that, it’s I don’t lose email. I’ve been using it for 40 years now. Come on, well, that killed the conversation, didn’t it?


Marg: No, it’s really good to know. If nothing else it’s just work from your best intentions to try to move the project forward and you have no control over whether it’s going to work or not [laughs].

Kai: I will walk back by follow-up a tiny bit by saying, by modifying it to say it’s not something to use with every single email. It’s something where it’s like, Oh, this is a deadline. Either they need to accept a thing or this proposal expires in three days. Do you want to work together?

Follow-ups, I think are 100% appropriate there and sort of dropped down depending on the lack of importance or time sensitivity. Hey, I emailed you for a recommendation for a taco place following up on this, please see previous email. It’s like yeah, but this follow-up was not necessarily there. So it definitely isn’t a one size fit all strategy, but it is a good one for getting replies to those important emails.

Reuven: Yeah. I’m just looking now in my inbox. We’re recording this on August 11th, so it seems, I’m sure it was just there two ago, but it seems that on July 29th, that’s two weeks ago, this big company client of mine asked me to send in a whole bunch of proposals for courses. So literally like an hour or two ago, their finance person emailed me and said, “Hey, could you send this quote in ASAP, thanks?”

So I’m like, Oh, they probably have a deadline and yeah, that’s happening in another month or two. So fine, I’ll get to it now. Of course, this is training me terribly, right? Like now I know, Oh, I can just wait until he sends that please send it. He’s probably rolling his eyes saying, Oh my God, that isn’t Reuven again.

But, but now I’ll actually do it and see the fact that would you mind doing this? Just saying the bump thing really drives me bananas. Maybe you didn’t see this, or I really need it soon or things are being held up that actually, I think he’s okay.

Marg: Yeah. I would also preface do not just email a client to follow up out of nowhere with the word bump only. Only do it if you’ve… I will preface it by saying, and maybe I didn’t drive home that point is we have a very established seven-year relationship, that’s our level of communication. So yes, as a PSA, thank you for the reminder. Don’t ever send someone a reminder that just says bump. That would be very uncouth.

Reuven: So that’s what I was talking about. I’ve definitely gotten that.

Marg: Okay.

Reuven: There you go, I will stop.

Marg: For sure.

Reuven: Okay, dear listener, we agree on everything now. All is good.

Marg: Yeah. But I am really curious because it seems very polarizing, which I’m actually really interested in the fact that it can be that polarizing. I’m wondering whatever medium you’re listening on, whether it’s embedded on the blog posts or, it’s an iTunes wherever you can comment or hit us up on Twitter to let us know what side of things you’re on. Maybe actually like when this airs, we can put a little poll on Twitter and see where people are at because I’m really curious how polarizing this is. Follow up emails, who know?

Kai: We have only got a couple of minutes left, so I’m curious, what would your sort of one email tip or one client communication tip be for a listener out there? Maybe they’re just getting started. Maybe they are established. Maybe they have an agency, but what sort of the one, piece of wisdom you’d want to share with folks when it comes to having better client communication? I could kick it off if we want.

Reuven: Go for it.

Kai: Templates. Do future you a favor, save that email, save that communication bit, whatever it is, save it as an email templates. So next time you need to send the proposal or follow up or say, “Oh dear client, it’s been great working with you, but I need to fire you because of reasons.” You don’t have to expend so much energy, creating that email again, full clock, so to speak. Instead, you could have a previous, you’ve just stashed away.

Maybe a Notion, maybe a text file, or maybe something like a text expander or Alfred, just to have it at your fingertips. Then you could start writing there. So I’m a big believer in the power of email templates. I use them continually and I strongly recommend to listeners, start using email templates, save that email, save it as a swipe, and then use it as a jumping-off point, next time you need to send an email like that.

Marg: Email templates. That’s a good one. I’m going to make my tip, not about email, if that’s okay. About Zoom, my tip would be ask them if they want to do video or not. It’s a simple question. That actually gives them a little bit of relief that it’s their call and you’re fine with both.

So my tip would be for client communication over Zoom. Just a quick note. We do in video or not, either way is good with me. It’s totally up to you.

Reuven: I would say, you want to be clear. So many people, especially when they begin their own business, start their own business. They’re convinced, Oh, I have to sound very businesslike.

I have to use all sorts of fancy language and have long things. Be yourself. Be clear. You were trying to build trust and you’re trying to get things done. So if things only take two sentences, write two sentences. It’s also okay to have your own personality in your writing, in email, and communication. Let your big clients be the faceless corporations with no sense of humor.

Kai: I like it. So for a picks this week, I’m curious what tools or resource or websites or books, whatever it might be that, we’ve picked and that we’d recommend to listeners?

Reuven: I got two picks. Number one is, I love, love Michael Lewis’s writing, and he over the last two years has done this podcast called Against the Rules. Where season one was all about who are the judges, who are the referees in the world? In many ways in American life and the second season, as good as the first season one, the second season was better. It was about coaching.

For anyone who is a consultant or freelancer hearing about different kinds of coaches and what they do and what they don’t do and how their good and their bad it was marvelous. It was entertaining. He’s fascinating. Tons, and tons, and tons of fun.

The other pick that I have is a book, called The Hardest Job in the World: The American Presidency. I would argue this is three books in one. Number one is it’s a book about the past and present and future of the American presidency, what it was designed to do. So if you’re into politics, government, political science, history, fascinating stuff.

Part two of the book is teaching you what good management is and learning from both successes and failures of these various presidents. What they did and how they did it and how they prioritize given an infinite stream of urgent and important things to do.

I would argue that the third, yet subtle part of the book. Is as he goes through the entire history of the presidency and what’s expected subtle and not so subtle digs at Trump, and how he is not fulfilling the 200, some ideas of history there. But even if you like him, I think the book is beautifully, beautifully written. I just love John Dickerson’s writing. So I have strong fixed out.

Marg: Nice. I have a book today as well. So the book has to do a little bit with our conversations called Radical Candor by Kim Scott. The tagline of the book is say what you mean and mean what you say. It’s a really good book talking about, especially with not only client, but team communication, brevity, getting your point across, and also not overly padding or sugarcoating things, but still, remaining strong in your word. Yeah. Radical Candor, Kim Scott, Awesome.

Kai: I’ve got a couple of links you could find in the show notes, dear listener on how to send and reply to email and email writing tips. These are a couple of articles from the Wayback Machine or that I’ve just encountered online in my safaring and just seeing what links have behind them.

These are great. They’re full of actionable tips from folks who respond to a lot of emails about how to write better emails, respond to emails in a better way.

If you stare at your inbox and you’re like, yo, this is an infuriating experience. I keep sending emails and then people keep writing back. How dare they? These articles will make it a much more positive experience or at least open your eyes to some of the tools or resources out there to have a better time dealing with email.

That brings us to the end of this episode. Thanks for joining us today. Be sure to take the time and, subscribe to the Business of Freelancing in your podcast app of choice.

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