Mastering Asynchronous Communication in Remote Teams

Adam:
This is Woo Biz Chat. Hi, my name is Adam Weeks, and this is…

Emma:
Hi, I’m Emma.

Adam:
Hey, Emma! Oh my goodness, it’s been a little while. We’re getting to catch up, and have we got a show for you?

Emma:
Oh, do we?

Adam:
Yes, yes, yes! This is Woo Biz Chat. This conversation came about because I was thinking of this topic, and I don’t know that we’ve really talked about it much. However, I have a new contract, and I’ve been working with 10up. 10up is one of the biggest agencies in WordPress, and they’ve grown so much because they do certain things really well. I’ve been so impressed with the team.

One of the things I hear repeatedly is about that “last 10%.” That’s really what gets them over the finish line with some of these big enterprise projects. It’s been a lot of fun getting to know this talented team. One of the people on this team, her name is Haley, and she is hilarious. She’s a project manager and very good at communicating.

In fact, this morning I hopped on Slack, as you do, and she had a very succinct but thorough rundown of an event we needed to be updated on. She did it in a way that was clear, funny, interesting, and timely. So, let’s talk about a few of those things we’re going to discuss in this episode. If you’re curious about asynchronous communication, this might be something unique—not to commerce so much—but in Woo, I imagine we have to work asynchronously. We’re in our Slack, we’re in our email, and we need to have a good foundation and a good way to communicate asynchronously. We’re going to dive into all those topics.

Before we start, is it okay to swear? When can you be funny? When can you not? All these things—so that’s what we’re going to get into. Also, Emma, one of the reasons we picked this topic is that you are very good at it, and I’m going to learn from you today.

Emma:
Except for all of…

Adam:
Let’s start us off. Tell me your general thoughts on asynchronous communication. Do you have a philosophy? What are your thoughts from a high level?

Emma:
That’s such a loaded question! It’s like, how do you pack everything into one nicely typed-out message as a response?

Adam:
It’s hard, right?

Emma:
It really is. Practice doesn’t make perfect, but it gets close. And everybody’s different. One thing we can start off with is that there are so many different audiences, and people know you at different levels, so everyone will interpret communication differently. But just to quickly start off, for people who don’t know—what even is async communication? Basically, it’s communication where the participants don’t need to interact in real-time. It doesn’t have to be face-to-face. It can be messages or information exchanged on Slack, Messenger, Teams, project management tools, emails, etc.

This is different from synchronous communication, which is what we’re doing now—calls, meetings, phone calls, live chat, stuff like that. Asynchronous communication is when a message is sent, and you deal with it when you can. So, what are the best ways to deal with it from there?

Adam:
Alright, asynchronous communication. We use it a lot in this industry because of the nature of the work. Time zones are another reason for async communication. Your day might not overlap with your coworkers or clients completely. It can be helpful to get something moving, and then when you go to sleep, someone else is waking up and takes it from there.

Alright, I’m going to ask you a few different questions. You’re good at this! What is one thing you try to do when using async communication? What’s a guiding principle for you?

Emma:
It’s actually kind of funny because we communicate like this a lot due to our time zones. Yesterday, I sent you a message before bed like, “Here, check out these show notes,” and then I checked it after your full day. But it wasn’t always that easy. Well, with you, yes, but with other people, maybe not as easy.

I stand by this: over-communicating is never a bad thing when it comes to async communication, especially if the person has never met you before. Whether it’s a quick “huddle” on Slack or Zoom, if someone’s never put a tone or voice behind your words, they might interpret it in many different ways. So, clarity and context are essential. Sometimes, I reread a message I sent and think, “I know what that means, but maybe the person reading it doesn’t.” Over-communicating is never really over-communicating.

Adam:
You are never penalized for over-communicating. The person may be annoyed, but that’s okay. They can skim it.

Emma:
Exactly. One person might say, “I already know all this; why did you write so much?” But maybe 99 other people reading it will go, “Oh, it all makes sense now. I don’t have to ask any follow-up questions.” Amazing!

Adam:
It’s like taking notes in a meeting. You think, “Oh, I’ll remember that.” Nope, I won’t remember that.

Emma:
No way.

Adam:
My brain doesn’t work that well.

Emma:
My brain ain’t braining.

Adam:
My brain ain’t braining! And sometimes, you’re taking notes for someone who wasn’t at the meeting. If someone gets hit by a bus—this sounds terrible—and they weren’t there…

Emma:
They’ll have the notes communicated async. Just kidding! Because they’re…dead. No, wait, sorry. Too far.

Adam:
Asynchronous communication. What was I saying?

Emma:
You were talking about taking notes for someone else.

Adam:
Right, your notes need to stand on their own for someone who doesn’t have any context. You won’t be penalized for over-communicating, and the person you’re communicating with might also be forgetful. You won’t be penalized for clarity.

Emma:
A hundred percent. But in addition, I’d recommend—depending on the type of communication—if you can, jump on a short call. Putting a voice behind the words they’ll read on a screen helps, especially if it’s the first time you’re giving feedback. You don’t have to do this every time, but I recently did this at work. I was in a call with some team leads, hosting a meeting. I can’t remember all the details, but at the end, they asked for feedback.

I’d never given this person feedback in written form before, and I made sure there was enough context, examples, and action points in the message. But then I thought, “You could read this the wrong way.” So I said, “Hey, can you hop on a quick call? I’ll send this feedback afterward.” It was just a quick Slack huddle. After that, the next time I sent feedback, it was clear, and I didn’t need to overuse emojis.

Sure! Here’s the continuation of the corrected transcript:

---

Adam:
Wait, wait…

Emma:
You couldn’t see me, but I also did cat claws, like “rawr.”

Adam:
Everyone’s imagining that now.

Emma:
I thought, “She asked for feedback, so let me jump on a quick call to give it to her.” After that, when I sent the written feedback, it was very clear. She could now imagine my personality behind the words, without me having to overuse emojis.

Adam:
Oh, all the emojis.

Emma:
Yeah.

Adam:
So you bring up a good point. We’re talking about asynchronous communication and how to use it, but there’s also the point of when not to use it. I’ve come up with this framework: information is shared quite well asynchronously—whether through emails or Slack—but if you’re trying to connect with someone, solve a problem, or if there’s some emotional element involved, it’s better to hop on a quick Zoom call, or use Slack’s huddle feature. Sometimes something that might take back-and-forth exchanges in Slack—or even be misunderstood—can be solved in two minutes over a call. Don’t try to solve problems over a text message.

Emma:
I agree. If there’s no quick decision being made or communication is being lost due to a lack of context, then move to another method. Whether it’s a call, a huddle, or a voice note—even a quick voice recording can help bridge the gap.

Adam:
Oh yeah, voice notes are great. You can record a quick message. Another thing I don’t use enough is video recording—where you record your screen and say, “Hey, this is what I’m seeing.” They can hear your voice and see exactly what you’re seeing, which can be super helpful. So, there are lots of ways to handle async communication.

Alright, so we briefly talked about emojis—emoticons? I don’t know the difference. How do you use them? When do you find them helpful, or when are they annoying?

Emma:
One of the things I love about working with Hosting or switching to different Slack groups is the custom emojis they have. They’ve got all these little dancing characters. When I move to WordPress Slack, or back to our group, I’m like, “Where’s the dancing cookie?” or “Where’s the cat spinning on a Roomba?”

I also have a “Hall of Fame” of my own custom emojis, like Emma smirking, Emma flabbergasted, Emma disappointed. And I’m sad when I go to Messenger or another platform that doesn’t let me use them. Sometimes, all you need is an emoji to express yourself.

Adam:
Okay, wait—Bob, if you’re listening, we need to get all of Emma’s custom emojis on Slack. I want them all!

Emma:
Yeah, I think I can make them myself. We’ll have to see. But we kind of have this weird thing where the original smiley face—the one with no teeth—has turned into this passive-aggressive emoji for some reason.

Adam:
The thumbs-up emoji—is that okay?

Emma:
Oh yeah, thumbs-up is okay. We kind of use it as the end of a conversation, like, “This is done. No need to continue.” It’s like when you’re dating and don’t know how to hang up the phone—you hang up first, no, you hang up first. Someone sends a thumbs-up, and that’s it. It’s all good.

Adam:
It’s all Gucci! What about the hands-raised emoji? You know, the two hands in the air?

Emma:
Yeah, we use that one a lot, along with the “grinning” emoji, which is like, “Oops, we’ve got to work on that now.” And of course, the sweating smile when something doesn’t go as planned. The shrug emoji is also a big one.

Adam:
I love the shrug emoji.

Emma:
Oh, totally. It adds a little bit of emotion to your communication. Sometimes, just a simple emoji makes the message more relatable—especially if you’re trying to send kudos or hype someone up. But don’t go overboard with emojis either, because then it can distract from the actual message.

Adam:
Too much emotion, not enough content.

Emma:
Exactly. And on that note, there are some emojis that don’t age well or might accidentally offend someone. Sometimes an emoji or symbol might become controversial or inappropriate, and then someone calls you out on it. If it wasn’t malicious, just delete it and learn from it. There are boundaries to emoji usage, but they can be a fun and helpful tool.

Adam:
So, the takeaway here is: use emojis, but don’t overdo it. They’re helpful in adding some humanity to otherwise black-and-white text. You can only use so many exclamation marks. Do you use exclamation marks a lot to add emphasis?

Emma:
I have this weird thing against exclamation marks. Stop shouting at me! Nobody’s that excited. I tend to avoid using too many. However, I’ve caught myself doing it when I’m really excited. Someone once gave me feedback about that—because I tend to end messages with double periods or double stops, like “..” instead of a single period or an ellipsis. They said that it could come across as unhappy or cold if I didn’t add more information or an emoji. So, I switched that up!

Adam:
Communication evolves, right?

Emma:
Yep, if you’re trying to ensure people know you’re happy or positive, throw in a smiley face or something.

Adam:
That’s a great point—feedback can be really helpful for improving how you communicate. So, what we take away from this is: give feedback on how someone’s async communication is going, and assume the best in them, especially when you don’t hear back.

When someone doesn’t respond after you’ve put effort into your message—there are crickets—how do you handle that situation?

Emma:
Yeah, that happens. Especially because my team spans 10 time zones, there’s no way everyone is online at the same time. So, one thing we do is react to messages with an emoji once we’ve read it or acted on it. Sometimes that gets old, but it becomes second nature—react with a fun emoji so that people know you’ve seen the message.

Also, I’m all for tagging people. Not aggressively, but if 24 hours have passed and you know they’ve been online, tag them again. Ping them until they see it! It’s easy to miss a message in Slack or Teams, especially if it pops up briefly and you lose it.

Adam:
Exactly. Sometimes you see a message, but then it disappears, and you can’t find it again.

Emma:
Right, or if you accidentally open it on your phone, you’re kind of out of luck. So don’t feel bad about tagging people—ping them a few times. From my perspective, I’ve never gotten mad at someone for tagging me multiple times. If I missed it, I appreciate the reminder. You could also use a loading emoji, like “I’m working on it, but give me a minute.”

Adam:
So, aggressively tagging—got it. Another thing I’ve found helpful is to avoid asking seven questions in one message. If someone knows the answer to six of them but not the seventh, they might delay responding altogether. Break it down to one or two key questions.

Here’s the continuation of the transcript with corrections:

---

Adam:
So, break it down into one or two key questions, and when you get that response, they can address those first. When you overload someone with too many questions, they’re more likely to ghost you—not because they mean to, but because it feels overwhelming.

Also, when you do get a response, you might see a little checkmark or a “done,” or they might write “received” or “great question, let me follow up.” That’s something I try to do more of—if someone asks me something complex and I don’t have all the answers right away, I at least let them know I’m thinking about it or working on it. It helps keep the conversation moving forward.

Emma:
Yeah, that’s important. And if your company already has established procedures, emojis can be helpful for tracking communication, too. You can use a “loading” emoji, the eyes emoji, or a “working on it” emoji to show progress, and then update it when you’re done.

I also want to touch on the formatting of async communication. If you need to ask more than three questions, it can get confusing. If you have a multi-part conversation, I recommend sending a separate post for each topic so they can each have their own dedicated thread. That way, less information gets lost compared to a giant message where everything is lumped together. Otherwise, you might end up having to schedule a call because there’s too much going on in one message.

Adam:
That’s a great tip. Another thing I picked up from my friend Haley at 10up is the importance of consistency and rhythm in communication. If you’re managing a project and have a weekly meeting or update, try to send your agenda or summary at the same time every week. People appreciate predictability in communication—it helps build trust and reduces surprises.

Another good tip Haley mentioned was drafting your message in Google Docs and getting peer review before you send it out. What’s your take on that?

Emma:
I think it depends on the message, but yeah, I definitely agree with using Google Docs for longer or more formal messages. I’m more comfortable writing in Google Docs because I have Grammarly and other tools to help catch mistakes. Also, if it’s something important or if I need input from others, I’ll ask someone to review it before sending it.

Sometimes, I’ll ask for feedback like, “Does this have enough context? Does this sound like me? Do I sound upset or annoyed?” Having another set of eyes on a message can help make sure it’s clear and professional before you hit send.

Adam:
Yeah, I love Grammarly Pro for the win! It’s not just about catching grammar mistakes—it’s also about ensuring that the message aligns with what you want to convey. Especially with important messages or anything client-facing, it’s good to slow down and have someone else review it. Don’t rush to publish it—take a beat, have someone look it over, and make sure everything’s in order.

And one trick I’ve learned is to set expectations upfront. Instead of saying, “When you have a minute, can you look at this?” say, “I need to send this out by 7 PM; would you mind reviewing it before then?” That way, they know how urgent it is, and if they can’t get to it in time, you’re still able to send it by the deadline.

Emma:
Exactly! And it helps to be clear about expectations, especially in different time zones. Also, if something is optional for some people but mandatory for others, it’s important to tag those people directly so they know they need to review it.

We had an example today on my team where someone sent a message with a summary and action points, and then said, “You have until the end of the day to challenge this, or I’m proceeding.” That’s a great way to set a clear timeline and let people know what the plan is.

Adam:
That’s a great way to handle it—give a clear deadline for feedback and move forward if no one challenges it. There’s a phrase I like: “It’s unkind to be unclear.” Sometimes we try to be too nice, saying, “If you have time,” or “whatever works for you,” but in the end, it just makes things more confusing. Being direct is better.

Emma:
I agree! It’s like when I speak, I tend to say, “Maybe, possibly, kind of…” but in messages, I’m much more direct—“Do this” or “This needs to happen.” It’s about clarity and getting things done.

Adam:
Yeah, it’s unkind to be unclear. You want to be kind and polite, but also clear. It’s a balance—don’t leave people guessing, but also don’t be overly harsh. And if you’re giving people a timeline, tell them when you need something done, and if it’s okay if they don’t respond, let them know that too.

Emma:
Exactly. And when you’re writing these messages, also be aware of the language you use, especially when it comes to different cultures and inclusivity. You don’t want to unintentionally offend someone, so choose your words carefully. And if you do make a mistake, apologize and learn from it.

Adam:
Yes, that’s a great point—be mindful of your audience and the words you choose. And if you mess up, own it and apologize. We’re all learning.

Alright, we’ve covered a lot, but we still have one more sensitive topic to discuss: swearing. Is it okay to swear? When is it okay, and when is it not okay? What’s your take on dropping swear words in async communication?

Emma:
Personally, I have a bit of a potty mouth, so I’m used to swearing in my day-to-day life. But in async communication, it depends on the company culture. At Hostinger, for example, it’s common for people to drop the occasional F-bomb internally, but I wouldn’t swear in a message to someone I just met or on their first day.

I think swearing is something that comes with familiarity—it’s more about knowing your audience. If it’s internal and you have a good relationship with the person, swearing might be fine. But for external clients or more formal situations, it’s definitely a no-go.

Adam:
Yeah, I agree. Don’t be the first to swear. If you’re building a relationship or working with a client, keep it professional. There’s a time and place for it, and you want to be sure it’s appropriate before you start using swear words.

At the same time, you want to be authentic. So if you’re comfortable swearing in certain contexts and it feels natural, it’s okay to do that—but be mindful of the situation.

Emma:
Exactly. Be yourself, but be cautious. And remember, in async communication, everything can be screenshot and shared. So, if you’re swearing in Slack or anywhere else, be aware that it could end up somewhere you didn’t intend.

Adam:
That’s a great point. Always assume your message could be shared, even in private channels or DMs. If you wouldn’t want your message to be forwarded, don’t send it.

Another thing I try to do in async messages is start by being human. It’s easy to get straight to the point in async communication, but it’s nice to start with a “Hey, how are you?” or “Hope your week is going well” before diving into the business stuff.

Emma:
I agree! My greetings change depending on my energy levels. Sometimes it’s “Hey,” sometimes it’s “Hello!” with lots of o’s, or even a dancing cactus emoji. But I always try to start with a personal touch because we’re not just talking to robots.

You should ask how someone’s doing before diving into work, especially if you haven’t spoken to them in a while. Just like in person, you don’t walk up to someone and immediately ask them for a status update. Start with a greeting, then get into the conversation.

Adam:
Exactly. It helps build rapport and makes the conversation feel more human. It also shows that you care about the other person beyond just the task at hand. Any final thoughts as we wrap up?

Emma:
I had one, but it’s gone now. My brain isn’t braining anymore!

Adam:
The best part is you can tell me later—async communication!

Emma:
Yes, exactly! I’ll ping you later. But seriously, if anyone listening has questions or specific scenarios where they want help improving their async communication, feel free to send me a message. I love helping with that kind of stuff!

Adam:
Absolutely! And if you, the listeners, have any tips or strategies you use for async communication that we haven’t covered, please let us know. We’d love to hear from you.

Emma:
Yes, and if you have any other topics you want to discuss with us, we’d be more than happy to have you on the show. We can talk, and, you know, shoot the poo—uh, I mean, shoot the shit.

Adam:
And that is a sign that we’re wrapping up this episode of Woo Biz Chat!

Emma:
This is why Emma doesn’t close the show. Goodbye, and thanks to all our listeners!