The Collaboration Problem Most Remote Teams Ignore

Galen Low: Leading remote and hybrid project teams is not new, but that doesn't mean that it's not complex. And truth be told, many of us have just accepted remote collaboration as an imperfect alternative to in-person work, the awkward and underpowered little sibling of actually being in a room together. But perhaps what we're not asking ourselves enough is, what can we be doing to actually improve the collaboration experience for our remote and hybrid teams? How can we translate some of the best parts of collaborating in person to a remote context? And even if we do, will it make any difference to the results?

To unpack that, I've brought in an international project professional who has been passionately pursuing better experiences for her remote and hybrid teams. Together, we're going to explore what remote collaboration experiences are often missing and where a few minor tweaks to our process could pay off in spades as more impactful project outcomes, stronger team-led innovation, and deeper relationships with peers and stakeholders alike. Hope you enjoy the episode.

Welcome to the Digital Project Manager Podcast—the show that helps delivery leaders work smarter, deliver smoother, and lead their teams with confidence in the age of AI. I'm Galen, and every week we dive into real-world strategies, emerging trends, proven frameworks, and the occasional war story from the project front lines. Whether you're steering massive transformation projects, wrangling AI workflows, or just trying to keep the chaos under control, you're in the right place. Let's get into it.

Okay. Today, we are talking about navigating the new realities of leading projects in a modern work context where teams are distributed, collaboration is often asynchronous, and AI is enabling team members to get more work done in relative isolation. We're gonna be unpacking the skills needed to lead remote teams effectively while still keeping things human. We're gonna be doing an audit of skills that we may be forgetting from fully in-person project leadership and how to achieve similar results in remote and hybrid environments. And we're gonna be sharing our recent experiences working with highly skilled professionals who are using AI, and how we as leaders can keep the work collaborative, high quality, and human led.

With me today is Karen Chong, Fractional Project Management Lead at Abracademy and host of the Mind Blend Podcast. Karen is a project management professional with extensive agency and in-house experience in marketing, advertising, branding, website development, and application development. Her career has spanned across the US, the UK, Hong Kong, and Japan, equipping her with the tools to thrive in varied work environments and cultures.

And she just happens to live at the intersection of remote work and in-person collaboration, with half her career spent working on-site creating digital experiences, and the other half planning in-person events as a fully remote fractional professional.

Karen, thanks so much for hanging out with me today.

Karen Chong: Hi, Galen. Thank you for having me, and thank you for that intro.

Galen Low: I'm really excited about this because, you know, your journey has taken you from stateside to overseas to a number of other countries. You've been in person, you've been remote. I know that you have a sort of deep perspective on human collaboration and what leadership means and how we get work done that, you know, becomes more valuable than the sum of its parts.

And a lot of that is not just a volume, like, of work. It's not just efficiency and productivity. It's not just all the outputs. A lot of it is about team and team culture and relationships, and I'm really excited to dive into just, you know, some of the things that maybe, you know, are working fine in the remote and hybrid work experience, but could be a little bit better if we were to kind of, you know, take that lens and turn it back around to what did we have when everything was in person, and how can we replicate that?

You and I, we can go down some rabbit holes and some interesting tangents, and honestly, I hope that we do. But just in case, here's a roadmap that I've planned out for us today. So to start us off, I just wanted to set the stage by hitting you with, like, a spicy question that my listeners have been asking themselves in the back of their minds, but then I'd like to just unpack that and talk about three things.

Firstly, I wanted to talk about how you create culture with your remote teams and why it's important to you to build bridges between team members and foster learning so that people can get good work done. Then I thought we could just look at some of the things that we've learned as leaders that we may have lost from the in-person experience and how we can infuse the same benefits into remote and hybrid teams.

And then lastly, I'd just like to lift the lid on how AI is changing remote collaboration and what you're doing to adjust your leadership approach accordingly. How does that sound to you?

Karen Chong: Sounds good. And I'm sure we'll go into some rabbit holes in our conversation.

Galen Low: I hope so.

Karen Chong: But we can manage.

Galen Low: Yeah. Don't worry, listeners, we're not gonna just go on tirades. But yes, I think there's lots of dimension to this as well, and we were talking in the green room, like, you know, I don't want this to be like, "Oh, you know, remote work is better," or, "In-person work is better." I just think that there are elements of the human collaboration experience that we haven't really thought too deeply about because we've been forced into these work situations.

You know, I know some professionals have been working remote for decades, but definitely after the pandemic, the COVID-19 pandemic, we were kind of forced into a mindset, you know, collectively, of remote and hybrid work, and now we've got this AI elephant in the room that's pushing us, you know, into productivity, into efficiency, and is that good enough?

That's kind of where I wanna go with it. But before I get ahead of myself, I just wanted to start us off with one big, hairy question. I'll take a running start at it. I've been seeing a lot of teams make the shift towards building, like, a truly remote-first organization. They are hiring top talent from around the world.

They are working asynchronously. They're having transparent conversations over Slack, and they're finding opportunities to bring in AI to fill in gaps as they go and keep themselves moving forward. But my question is this: Has remote work communication tools like Slack and AI actually made project teams worse at collaborating as humans, even if they've made us more efficient?

Karen Chong: So, like a lot of the things that you'll hear me say, it's not so black and white. So if used properly, and I explain what's properly, when used properly, async and all these digital communication channels is perfect for, let's say, you have a client update that's gonna completely change what people are doing at this moment.

A Slack message is good And it's probably easier than going to each person's desk telling them. And also it's good for documentations and things that are a little bit longer, people don't need to react to immediately, things like that. These communications are great, and AI help us. Today I, I went to the office, had a meeting, and I had three sources of meeting notes.

And of course, each one of them have important points and they can all be used as is. But because one is based off of Miro, one is based off of the recording, I do want to take parts of it, and AI helped me synchronize them and synthesize into one actionable note document. So it's great when it's used with the team in mind, with the people in mind, with the user in mind, who's gonna be reading this, what they need to do.

But when it's used as a replacement of decision-making, maybe discussion or bouncing ideas off but asynchronously, then it makes it complicated. It adds work and we may seem more efficient, but we have to go back and redo it or it creates confusion, so you have to go back and... So it's a tech debt in a different format.

Galen Low: I can relate to that idea that you know, you might have different sources of information. You have, you know, your own notes, you have the AI note taker, you know, you have what's captured in Miro. And it's funny 'cause where I work, like, we don't email, we Slack. And then it creates this blur of like, is this a real time channel or is this a channel where I can pick it up in the morning?

And you know, we've sort of organically landed on the idea that it's like, okay, we have these work behaviors that, you know, we've got teams that cross time zones and so immediate isn't always a thing. We can't always necessarily just rely on, okay, it's their working hours, therefore they must be, you know, responsive.

And I personally don't want to be sort of up at 4:00 in the morning to be responsive, you know, to the team in Portugal. So it's interesting this sort of blur on the channel, which is like, okay, well now we've got Slack messages that, you know, it could be one line or it could be, you know, as long as an email.

And then it could be like, "Oh, and here's the notes, you know, from the meeting," and it's got this attachment and suddenly this like bite-sized channel, right, for instant messaging is actually, it doesn't mean that you're gonna get, you know, a short message. It could be, that could be like two hours of work that just arrived in Slack.

I don't know if that's, you know, something that other teams feel or that you feel in your team, but I like that idea that you're saying of like, okay, well there is this sort of combining as well and curating and tailoring so that you can communicate that effectively to a team for its purpose rather than just being like, "Hey, we have all this stuff.

I'll just dump it into Slack. Everyone will have to read it and then we'll have to figure out what to do about it."

Karen Chong: Yeah, 'cause if you think about it, Slack and team messages, it's really just like a messaging platform. I've seen teams use it as a project management platform, and I wouldn't say it worked the smoothest, but if you think about it, it's like having a hallway chat when you're in person, or think about the text messages you use with your friends and family.

Would you take that as Say, if you ask for advice, you... Would you use that as in-person, face-to-face, or even over the phone conversation? Would you just take that and replace it? No, right? So if you have serious discussion or you have long things that people need to read, it doesn't even show the whole thing.

Right. If you're reading on your phone, or even on, on your computer, it collapses it for you. You diminish the value of whatever you put in there. So why not use it for that purpose? Draw attention, reminders, link people to where they can have more information should they choose to.

Galen Low: And so would you say that for you, the Slack and Teams, that is your side of desk conversation, that's what you use it for, and then anything else, you're kind of like linking it away so that it's not like, "Hi, good morning.

Here's 400 pages of documentation for you to read"?

Karen Chong: Yeah, like my... I try to limit my messages to like this. I know on audio we can't show it, but it's about- ... five centimeters long on computer screen. On your screen. Because I know, I know I skim, and I know it... Not everything is gonna get across. So I make an effort to make the important points stand out, and I do not ever write a paragraph in there unless I need something that's paraphrased, here's what the client said as is type thing.

I use it very much like a messaging channel. It's never for documentation. It's never to store files. It's really just to bring it to attention, bring it in front of people, highlight it, bring it back up.

Galen Low: Is that something you cascade to your team as well? And you're like, "Listen, I'm gonna put masking tape on your screen, and that's the, like, maximum length-

of a Slack message, please. Thank you. This is our team culture."

Karen Chong: The team is pretty okay, 'cause the company I work at, Ab academy, we are remote first. So there are a few people in London, but the rest of the team is everywhere, in all continent. So we are pretty good at using Slack as just, like, messaging, bringing people's attention to, "Hey, can you look at this in Miro?"

And just... And because it's not instant anyway, me in Australia, it's never real time. Right. Yes. So it's very much, I share this document with you, blah, blah, blah, blah, blah. Or like, I wanna set up meeting with you at this time. Can you make it? Like, this type of quick one-off.

Galen Low: I love that idea that, like, even in person, that would never be like that I'm gonna come over to your desk and talk at you conversation.

You would never overlap.

Karen Chong: But yeah, you wouldn't go there, expect to get an hour of this person's time just showing up at the desk. So it applies to messengers too, like, can't expect them to read two pages.

Galen Low: We had so many decades of refining in-person work experience, right? And like, what is appropriate, and what's the etiquette, and, like, how long is too long to linger in front of someone's desk when they're clearly, you know, trying to put their headphones back in and continue to work.

And like, you know, there's all these things, and I like that, you know, you are establishing this with your team. Like, here are the, like, digital asynchronous norms. You know, don't expect it to be like, "Hey, good morning. How are you doing?" And then get an instant response from Australia when it's, like, 2:00 in the morning for them.

But also your, your communications are gonna be different, but can still be brief, because I think that is a temptation. I wanted to go back to something that you said. You said, you know, you have these different AI tools capturing and gathering for you, but you are taking the time to merge and sort of distill them.

And, you know, I, I know I'd asked you the question, I was like, you know, are we being so efficient that we're actually getting bad at collaboration? And some people might hear that and say, "Well, was it efficient what Karen just did?" Taking, you know, these outputs and then, you know, like crafting them into a thing.

Like, what is the value there that you get from that extra step of not just dumping documentation and sending that short message on Slack to be like, "Here's those 14 documents from that meeting," and then have the link. Like, what is the value of you sort of combining them?

Karen Chong: So what the recording captured is only what people verbally said.

What Miro captured was the sticky notes that they put on the Miro board when we were doing the exercise. So not everything was said. Not every sticky was verbally explained. So Miro has Miro side of understanding, and the transcript has the transcript side of understanding. The summary from the transcript summarized what people verbally said.

So because you have all this information and because us, the human, were in the room, so the humans were the only one who h-heard both, who saw both. So if I'm documenting that, I should try to give the documentation as much of the understanding as possible and help people make sense of it when someone picks it up.

And let's say we are doing the next workshop with this client. We said these didn't work too well. Some of it was just that. Some of this was in the sticky. With this combined and with AI, it's a lot easier to know for the third workshop that we're designing, we probably shouldn't repeat the things that they said, "Oh, I wish this could have been better."

So by doing that, because I was in the room, I know both of these are important, and if I have two separate documents, that's not useful either. No one's gonna take the time to read If half of them

Galen Low: Oh, I like that. They'll need to stitch it together anyways.

And it's something we take for granted because in person it's one experience, but so when you're going to do it virtually or in a hybrid situation, like, there's layers of the experience.

In my head I'm like, oh my gosh, what we need next is, like, a sort of facial expression capture. Then you can merge that all in. You can be like, "Someone wrote this sticky note, they put it on the board, we talked about it for a bit, and then Jerry made this face."

Karen Chong: Like insert sentiment. I'm not surprised that's coming.

I was thinking about where we are a year ago and today. I remember a year ago there was a workshop, there were physical Post-It notes, and the facilitator was trying to figure out what's the easiest way to transfer those digitally. That technology was not readily available. He could do it by plugging in a few things, but now we can do it in one place.

Galen Low: Yes. It almost doesn't make sense to use actual sticky notes anymore because of that.

Karen Chong: I have a point about that, but I'm sure we'll cover that.

Galen Low: Okay.

Karen Chong: Yeah.

Galen Low: Mental note, return to sticky note things. But you're right, yeah, like how many times have our listeners rolled up the butcher paper full of sticky notes hoping that they're all gonna stay together, you know, get back to the office, unroll it, take a picture of them, painstakingly transcribe it.

Like, it's like, you know, that was happening anyways, and I think what you're saying is really interesting, just like, okay, well now we don't have to do that, but also they are different layers of information that we need to merge so that we have an accurate document of what happened. And that thing you said, no one's gonna do that themselves and go like, "Well, I guess I'll look at the Miro output and then the transcript and then read through those, you know, w- like with one on either side of my screen and you know, try and figure out what happened."

Part of the value is synthesizing it for the team so they can keep being productive, but also so that there's like a, a record of alignment, not just what was on the board, not just what was said, but, you know, both combined so that that becomes a source of truth. That makes a lot of sense to me.

Karen Chong: Yeah. And the important thing is think about what I and the other team members will want to use this document for.

Because let's say it's summarized beautifully. It's a chapter in a book. But what does it mean for the next one? What was good? What was bad? What the client wish would happen? Like, so I asked it to break it down into, like, keep this format. There are other tools that help me do that. I didn't have to go through it and tell it, but the important thing is make it easy for people to read and get the information that will be useful for their work.

Galen Low: I actually really like the idea, even though this isn't exclusive to remote or hybrid or in person, but I love that idea of not just capture, but, like, the insight of, like, here's what we can do better next time. Instead of putting that at the beginning of the next time you're planning it, it's the feedback.

It's the end of that process so that you have it there on record and people can be thinking about it already. And what I like about it in the context of this conversation is that it drives and continues to elevate the way we work remotely or in a hybrid context. You know, everything from, yeah, next time we gotta, you know, get a better microphone that isn't so directional, or next time, you know, we should have people's cameras on or what have you.

And I know it's not necessarily the feedback you're talking about, but I find that we're so satisfied. We're like, it's almost like an accepted this is the standard of remote work. We're always gonna spend two minutes trying to fix the camera. We're always gonna have somebody who's hard to hear. We're always gonna, you know, and it's just this compromise, and that's fine. It's always gonna be that way.

But I think you're right. I think this is, like, something that's evolving really fast, and we don't need to just, like, accept that this is the way it is, that it's imperfect, and like, gosh, I wish we could all just be in person again. Those days are done, right? Like, businesses have moved on, transformation has happened, you know, and I think it can be better.

And I think that's what I love hearing from you as you're talking is that, like, this deliberate, intentional way of making the collaboration experience better, whether it's in person or hybrid or remote, and always be fixated on that. Because ultimately, it shouldn't be this compromise or this sacrifice to be like, "Yeah, work is pain."

It should be something that can improve.

Karen Chong: And being intentional is valuable in an in-person, hybrid, or remote environment anyway. But because we're increasingly getting remote, increasingly hybrid, being intentional has become a lot more important. And in the in-person world, you have the accidental organic moments that you can share information, update each other, you know, chit-chat, or you were going somewhere, but someone tell you, "Oh, I forgot to tell you this at the meeting."

Those types of things, they don't happen anymore in a remote or hybrid. So you have to intentionally build in moments so that you can gather feedback.

Galen Low: I like that. I actually wonder if we can go there because, you know, some of the things that I've been thinking about, that we've been talking about are just like, you know, there are some things that do only happen in person.

And so maybe I'd ask you, like, what do you think remote-first project professionals are kind of missing today that previous generations absorbed and benefited from almost by accident when teams were, like, all co-located?

Karen Chong: So the first thing that came to mind is the organic opportunity to build rapport and relationships.

Galen Low: Ah.

Karen Chong: Because it doesn't happen unless you set up something, unless you send someone a message. That doesn't happen. So the people who have been remote, they have been optimizing for their independence, so they develop a skill to be self-sufficient and to keep up with the team, to not need a whole lot of guidance or, like, develop a habit to clarify everything they need to know, so their output aligns with what the project needs.

But as more of us are remote and there's more hybrid team situations, we need to optimize for collaboration. So just because you are self-sufficient- Doesn't mean everyone is marching towards the right thing and designing for the right problems. The biggest part there is the opportunity that they're missing.

They're missing out on that, and also the... Let's say, if you're in an office together, you may be walking to the same train station after work, you may happen to go to lunch together, and you don't get the casual moments, and you miss out on the opportunity, the organic accident opportunity to build trust, because trust in relationship is built upon shared experience to me.

So if you have, you know, sit through a client meeting together, or if you've been to an offsite together, or you got stuck in a traffic- Mm ... together on this bus- ... or the bus broke down- Right ... or anything like that, it doesn't happen organically when you're not together.

Galen Low: I like that. I, You know, my friend Kendall he had this notion of, like, serendipity as one of the things that, you know, we miss, and I think this is kind of what we're talking about.

You know, can we unpack that a little bit? Because rapport is such an interesting thing. I hear what you say about, like, the, you know, there are remote professionals, and it's valued to be heads down and independent and very productive and just, you know, get what I need and do the thing. How do we introduce, you know, this rapport-building opportunities or the serendipity into the remote experience without, you know, scheduling a Zoom call to be like, "Can we pretend we're stuck in traffic together?"

Karen Chong: Well, that'd be a fun game to play for my next one.

Galen Low: Yeah, actually, maybe we should do that.

Karen Chong: Because I mentioned building these opportunities, these intentional moments to create rapport or just to tap in on the things that you don't always read from the Slack message. So something that my company does in the beginning of meetings, whether it's with client or internal, we do intentionally check in, and the check-in is not just for the formality.

We are really interested in how the person's trip was, how was yesterday's workshop, how the weather is affecting them. So building intentional moments. And so- sometimes it's a game. Like, oh, what's the most important life-changing object right in front of you type thing. So it may not seem relevant to the project, but you get to know the person a little bit more.

And if you know the person a little bit more, let's say, from these conversations, I got to know that my client has a pet and loves... She's a foodie, so that helps me use other side conversations with her to Just be more a person to her, so I'm not just the project leader to her.

Galen Low: I like that. I like that it's, like, creating a shared experience within the context of, like, a scheduled meeting.

I'm a huge fan of that, by the way. Like, I think small talk is real talk. I do think it sort of builds that rapport and relationship. And let me, I was gonna go there, but let me ask you this, actually. So, like, what does that rapport translate into once you establish it? Like, why is it worth building it, and then maybe especially in a remote or hybrid sort of context?

Karen Chong: So if you think about it, would you be comfortable telling people, "I had a fight with my family," in a chat that has 10 people that you don't know very well- Right ... or two people that you know very, very well?

Galen Low: Hmm.

Karen Chong: So if you build rapport, you build trust. Even if the person is not completely comfortable with something, it could be, "I don't really fully agree with this requirement that the client gave us.

Can we talk about it?" They may not be comfortable to tell you if they don't really trust you or if they don't know you. Because if they don't trust you, they may think, "Oh, this person may think less of me," or, "Oh, I may come across as not knowledgeable in something that I'm very good at." You break down the barriers between you and the team, and it can also helps you understand their personality a little bit.

So something that's very important, especially in remote and hybrid world, is to read between the lines. Literally. Yes. Read between the... Literally read between the lines, and read the room. Because disengagement is, becomes more silent in a remote world. Burnout happen more quickly, and you just don't know how many things are going on.

'Cause if you think about, if you see someone with, like, a stack of paper back in the olden days, you know ... they may be pretty busy. They need to go through all that. But you don't really see people's workload, and people don't see your workload either.

Galen Low: Yeah, that's fair.

Karen Chong: So if you break down that barrier, 'cause communication is already complicated in a remote world, if you can minimize as many things that may come in your way in understanding what's happening and helping each other understand what's happening, that's golden.

Galen Low: I think it's a really good point. I mean, I've pictured in my head this sort of caricature of, you know, the, like, inbox outbox on your desk, and your inbox has, like, this stack of paper this high. But you're right, like, even, you know, I'm thinking back to, gosh, like, last time I was working in an office full time was probably 2018, 2019-ish, and, you know, someone actually had come to me and they said, like, "You've got busy energy."

Like, I'd stand at my desk all the time. I'm, like, working on decks and blah, blah, blah, you know? And it... What occurs to me is, like, that is a sort of in-person observation of my busyness, or at least my energy, that they wouldn't have gotten from, you know, a remote experience. And I know we've got resourcing tools and all that, but I, you know, as you were saying that, I was like, yeah, I'm not always clear.

My second question to almost everyone I deal with on my team is, "Do you have bandwidth for this?" And I'm trying to give them an opportunity to be like, "Well, yes, sort of." And I know it's a loaded question, you know, especially when there's hierarchy. They're gonna say yes, yes, yes or they're gonna do it at this time, or what, blah, blah, blah.

But, you know, I ask because I can't see their energy. I can't see how, you know, them running from meeting room to meeting room back to back, you know, skipping lunch. You know, I don't see that. I have to ask. But I think you're right that the information is not useless information, that I can use that in the way I lead, in the way I manage, in the way I plan capacity.

You know, if someone's, like, weeping at their desk, I'm not gonna keep grilling them for that deliverable. Like, I will find another way.

Karen Chong: Yeah.

Galen Low: You know? And that's going to make the team performance way better than, you know, forcing someone to weep quietly at their desk and deliver this thing, and I would have no idea.

And, you know, that to me would be, like, a broken team, where, to your point, they didn't feel comfortable saying it to me. I had been ignorant to it, and we just carried on because we're ultra productive, ultra efficient, high performing remote teams, right? Like, there's that pressure, too. You can see it sort of translate in terms of, like, the remote experience, and there are things that we can do, like, you know, to ask, to kind of be aware, and to, like, read between literally the lines of, okay, is this person's behavior, you know, a little bit different than normal, and what can I do to, like, explore that, and how is that going to, you know, help me lead this team better as a result?

Not just that individual and be there for them, but also, how can I reconfigure my approach to the team and the work we're doing to accommodate for that rather than just pretend it's not there?

Karen Chong: Yeah. And since you brought up weeping at their desk, I also want to bring up how remote makes reading the room a little harder.

It's really hard to look at nine squares at the same time. So when project leaders want to, you know, get a better temperature of their team or stakeholders, when you have a moment in a meeting, scan around the room because you can see. If someone has been crying, you can tell. So pay attention to people's behavior on screen.

Kinda like be a little more attuned to subtle signals 'cause disengagement, yes, it's harder to detect, but you can somewhat still sense it, and you can try to see how their response is to you over the course of time. And if someone, yeah, like you said, behave differently and if they stop turning on their camera, that's another sign of there may be something that I would like to dig into deeper. And just be better at observing energy and managing energy because if we're all remote, you know, you are in front of a screen More hours than you used to, it gets tiring.

And managing team energy is becoming even more important because just because we're at home doesn't mean the work hours...

You don't get 48 hours a day. So it's easy to forget that. Like, eight hours productive time, it wasn't impossible in person. It may still not be possible in a remote hybrid environment.

Galen Low: That's fair. And actually, you know, we do that, and some of the things that you and I have been talking about, you know, as we've been prepping for this, is sort of that idealized view of remote work, where it's like, okay, well, now we don't, like, need gaps between meetings.

We can be working back. You don't have to go from meeting room to meeting room, you know? You don't... Like, you can just be at your desk all day, you know, for more time, and we can be super productive, and there's no distractions, and you know, like, and, and, and. But, but I think there are a lot of people who are, you know, maybe not weeping at their desk on the regular, but, like, feeling under pressure and, you know, feeling like they are expected to ignore their bodies and just, you know, go from meeting to meeting.

You know, hang up a Zoom call, join another one. Maybe be on two Zoom calls at once because, you know, you could. You know, there's, like, a lot of this pressure to be like, "Okay, well, now I'm kind of this... I'm remote, and therefore, now I'm a machine," right? Give me instructions, and I will produce the outputs, and I will not take breaks and, and what have you.

I mean, don't get me wrong. I think that's still true in the in-person experience to somewhat, like, to a somewhat extent, but, like, there are these sort of forced gaps between things. How are you working with your teams to kind of, like, account for that? Like, if you're reading the room, and you're like, "Okay, everyone kind of feels like looking at people's calendars.

We're all, like, stacked back to back. Like, is this working? Do we need to make a change?" What is your sort of approach there?

Karen Chong: So I intentionally create moments that I know the team will need to, say, the pre-meeting and the post-meeting chatter that used to happen in person, I try to factor those in when I'm scheduling time with them.

So we always meet, say, 30 minutes before a client meeting and allow maybe 30 minutes to kind of debrief on it. So Now that is factored into their calendar. And of course, if I see that it's not possible, maybe that post-meeting 30 minutes become, like, later in the day. But intentionally creating those moments is important because you know it's needed.

Like, that 30 minute may be more worthwhile than, say, 40 Slack messages. And also, definitely try to not squeeze something in. You see a block, you squeeze it in, it's an hour block or 30-minute block in between two meetings. That's never good.

Galen Low: Right.

Karen Chong: 'Cause they are just coming out of something. They will take time to get into your topic, and then their mind is already going somewhere else for the next thing.

So it doesn't help anyone. But if it's impossible to find time with someone because you see that their calendar is blocked solid, maybe ask them. Like, "This will be important, but I see that you're solid blocked. How else, if not a meeting, how else can we look at this together?" Or, 'cause maybe some of the meetings they don't have to go to, and then they, they can choose a priority themselves.

Galen Low: I like that. And I think, yeah, the crucial bit there is asking. The extremes are, "I'm just gonna book it anyways even though this person's blocked their calendar," which, in my experience, never goes well.

Karen Chong: I have seen that.

Galen Low: And the other one is, "Oh, the calendar's blocked. I guess I won't ask." And it could've been a situation where they're just kind of protecting their time, maybe for a conversation like that.

Karen Chong: Yeah, and the, "I'll book it anyway" never works. And I have been on projects where I see that people are booked on five meetings, and they are expected to go to all five.

Galen Low: Right. Yes.

Karen Chong: So that is the extreme, and it was anything but useful.

Galen Low: It's funny because that's the other, we were talking about earlier, right?

Like, the stack of paper on someone's desk equals they're busy. But I think actually when you have open calendars, that's, like, the other... You know, it's not, like, a sort of organic visual thing. You walk by their desk, you're like, "Wow, that, that person's busy." But if you're working with someone and you're looking at their, at their calendar, like, and you're like, "Wow, you're booked solid," like, that is actually a good indicator for the remote world of, like, capacity.

It's like, "Are you stretched? I noticed you're booked for five meetings," right? Like, at 4:00, which is, you know, 2:00 AM your time. "Is that okay? Is everything okay? What can I do, you know, to make sure that, you know, the work environment is still healthy?" And not just for the kumbaya stuff, but because that's gonna generate better work, right?

The quality of the work will be better if we're not just, like, you know, stretching our capacity beyond 100% and hoping for the best.

Karen Chong: And this is one of the extra steps that project leaders need to do in a world like ours today. Before it could just be booking a meeting, like, but now we do have to look at their whole calendar to try to gather more information about their workload and- Yes, it is extra work, but it is also the reality.

If you pay no attention whatsoever to other people's workload and schedule, it doesn't really get you very far anyway.

Galen Low: I like that. I love the theme of intentionality. You know, I see why it's the sort of backbone of your approach, because we do need to create these things and, you know, to your point, like that meeting after a meeting, yeah, it would sometimes happen serendipitously or organically in person, but usually it would be like with like one or two people, and then the other

You'd have to fill in the other people, like, you know, along the way. But it is something that we know is useful, and therefore let's like be intentional about the time we schedule for it.

Karen Chong: Yeah. If that happens every time, you see that, why not just book it in? But you don't have to use a whole 30 minute.

Galen Low: Doesn't have to be an accident. When you say it out loud, you're like, "Oh, wow, that is kind of silly." There's one thing that also, that I wanted to come back to. We had talked about it a little bit, and I touched on it at the beginning here, but, you know, in terms of, like, some of the in-person experience, one of the things that I valued the most about my time, you know, working in person with teams, and even to this day when I'm s- you know, going to the office, going to HQ, some of it's, like, this, like, organic mentoring, right?

This sort of, like, observable learning experience, not because you book time with that person and, you know, you're like, "Please download your brain into my brain. I wanna learn from you," but because you're just watching people do their thing. Have you found a way to be intentional about this, like, sort of, sort of organic mentoring in a remote and hybrid experience?

Karen Chong: I do think so, 'cause right now it's sort of in my nature anyway. If I see that someone is doing something and I'm sensing that they may be not going about it the most efficient way, I may sh- like, for example, I may share, "Oh, I was using this for X, and I know that you're working on X as well. If it's useful, you can try this thing that I use," and stuff like that.

So because I'm not sitting right next to them, so I don't know exactly what they're doing, but from, say, regular check-ins, I will get a flavor of what people are working on. And if it's not relevant, then they'll say, "Oh, I don't need it." That's fine. But you create moments you converse as well. So it shows that you share knowledge.

It shows that you have knowledge to share, and you want to help, and that also, if they are indeed using something else that takes them twice the time, but your suggestion help them save time, you mentor them, and they trust you a little bit more.

Galen Low: And what I like about that is that it relies on this awareness of what other people are working on, which is fundamentally what it has been.

Like, I was thinking, like, the example I have in my head is that you know, when I was working for one of the big consultancies, like, I sat in a pod with a bunch of, like, senior managing director level folks, and there would be that sort of walk-by conversation. People would walk by their desk, they'd chat about that thing, and I'm like, "Okay, I'm gonna, like, pay attention because, A, I'm gonna be able to sort of learn how managing directors here talk to one another.

B, I'm gonna learn what kind of other projects people are working on, and I wanna see how they sort of interact and solve problems together." And my instinct was to be like, "Okay, well, that can't happen anymore," 'cause, you know, I don't- overhear anything while I'm, quote-unquote, "at my desk." But I think it comes back to that thing you said at the beginning when we were talking about rapport.

You know, there are still opportunities to build rapport. We just have to be a bit more intentional about them. And I like what you just said about, like, you know, in a way, you can be a good coach or mentor by being aware of what other people are working on. It doesn't necessarily mean overhearing it. It might just be paying attention.

You h- you have the information available to you, and you know the people who are sort of close to you or the people that you, like, view as role models that you can pay attention to. I think it comes back to that other thing. Sorry, I've been like... I've been thinking about what you had said earlier, and I'm like, yeah, even the, like, reading between the lines or reading faces and things like that, like, every opportunity, every time you're sort of, quote-unquote, "in the room," even if it's a virtual room, with people that you wanna learn from or people that you respect or people who are your role models, that's a time to really pay attention, not, like, multitask while that person's talking, but actually look at the room, look at the people's reactions, and learn from that sort of example.

It's still there. And the overall just you know, being intentional, scheduling, like, the time in. It might not be as easy to be like, "Hey," like, "after the meeting, can you, you know, share with me your approach and how you planned for that?" Like, that might be too rigid and, like, sort of, I don't know, forced.

But I think it is about paying attention and getting exposure to the things that people that you wanna learn from are doing. And that might be in your direct path, or it might not be, but there's definitely ways to create those opportunities and then, like, take full advantage of them, like, pay attention.

I still think it's one of the best ways to learn. Not everyone's a great teacher, even if they're good at their craft, so if you can, like, observe them doing their craft, that might be a much richer learning experience than, you know, reaching out and being like, "Can you teach me to, you know, tell good stories?"

They'll be like, "Well, I don't know. Just kinda follow your heart." You know? It's just like, okay, that didn't really work.

Karen Chong: Yeah. And, like, even in today's world, I don't think it hurts to even schedule something that may seem a little bit forceful, because we know that we are trying to Get clarity. We are trying to minimize information misalignment, and I think people are a little bit more open to that.

And one group that we haven't specifically talked about is stakeholders, leadership.

Galen Low: Ah, yes.

Karen Chong: Because in, in person, they may actually just happen to be running into you and ask you, "Oh, how is that project going?"

Galen Low: Right, yes.

Karen Chong: And that's natural. It's not because they know it's not going well. But in a remote hybrid world, if they ask you that, they are thinking about something is going well.

Yes. So that makes communication planning and stakeholder mapping even more important in hybrid remote world, because you would have to be intentional to be in front of them, 'cause out of sight, out of mind. If they don't see anything from you, they forget about you. And if you build a reputation of just sending, like, updates or scheduling meetings that don't need to be meetings, they remember that.

They don't remember how the project is going. So stakeholder management, stakeholder mapping, and communication becomes even more key in the remote hybrid world.

Galen Low: What is the r- remote equivalent of running into a stakeholder in the elevator?

Karen Chong: A lot of companies may have random, like, water cooler channels.

Galen Low: Yeah, okay. Be at the extracurricular stuff, yeah?

Karen Chong: Or I actually think that being remote hybrid, it may open up a channel for you to talk directly to the project sponsor... Well, you should have a direct line to the project sponsor, but say the C-suite, for example. It's not out of place nowadays for you to send them a direct message.

"Can I have one-on-ones with you periodically or whatnot? I send regular updates anyway, but I would like to allow an opportunity for you to go deeper or answer any questions that you don't think are answered from my updates." So being intentional to be in front of them, keeping them informed, and tailoring your communication considering that person's habit or their influence on the project or level of where they are in their company.

That is even more important nowadays.

Galen Low: I like the tapestry you're weaving because I'm, you know, thinking about you were saying about rapport and the importance of it and just building trust, and I know we didn't talk about stakeholders at that point, but, you know, y- y- building trust with your stakeholders, using those opportunities to build rapport unlocks the ability to have not the formal communication where I'm like, "Here's the status update attached.

Please review action items." Not that one, and not the necessarily, "Hey, can I, you know, spend a day with you and learn from you?" But even that in-between of, like, having built enough rapport, if it's appropriate, if the etiquette is, you know, permits it where you work, to be like, instead of sending the formal update, might just be the, "Hey, how was that barbecue?

By the way, I just wanna let you know that this blah, blah, blah, blah, blah." The end, right? Like, it... And I think you're right that in some work cultures, maybe not every work culture, but in, in some organizations, that is becoming a bit normal and acceptable. Even if you are pinging somebody who is in, you know, the C-suite or, or that senior director who you know is busy, it's still a mechanism to establish and reinforce and, and maintain this sort of more personal relationship that almost, I, I would say almost replicates that exposure to them in person.

I think it still, you know, creates learning experiences for you, gives you visibility, and that rapport and trust is something, yeah. I wanna say it's like playing the game, but it's not really. It's like rehumanizing a sort of interpretation of remote and hybrid work culture that is a bit robotic. You know what I mean?

It's like, let's rehumanize that. I won't get stuck in the elevator with you, but, like, what is the-

Karen Chong: How do I create that moment?

Galen Low: Yeah.

Karen Chong: To be stuck in an elevator with you?

Galen Low: Yeah. Yeah, exactly. Elevator chat.

Karen Chong: Yeah, and if you're not comfortable because the leadership is, like, three skip levels, maybe you could leverage, like, the layers in between and use them as feelers.

Like, our leadership aware of something, or would it benefit if I provide this information for them to use for whatever? I don't know, just be curious. Ask questions. Yes. 'Cause it's e- even harder now because we already know that, like, it's impossible to overhear, very hard to overhear. You just have to ask the questions 'cause that helps you uncovers things that you may not know.

It may help you correct miscommunication, misinformation, or whatnot. So being curious and asking better questions now is a skill that has been valued for decades already, but now it's even more important for project leaders to be good at that.

Galen Low: I love that. I actually think it's, like, one of the less obvious ones because it's easy to be asking about, you know, questions about the thing that's right in front of us that, you know, that was in the agenda for the meeting.

But not e- it doesn't occur to everyone to ask about other things that are happening, you know, the broader context, the bigger picture, as part of that conversation to, yeah, get that context and information that might be three or four levels above you, that you might not have direct knowledge of, but could definitely, you know, ask the questions.

And that's gonna improve the work you're doing, you know, boots on the ground, but also, I think it plugs you into opportunities to connect the dots and maybe opportunities for yourself.

Karen Chong: Yeah.

Galen Low: I wanted to ask you, because I know you work with a lot of remote teams, and some of them probably haven't ever met in person, but if a team that's always remote does have a chance to get together in person, what would you recommend that they do to sort of help make their collaborations even stronger?

Karen Chong: I would say do something that you cannot do remotely. So If you picture someone was visiting from a different office, say your Vancouver office has someone in the Toronto office, you wouldn't let that person just sit in a room by himself or herself, right? You would engage. So take the opportunity to do things you cannot do remotely.

So for example, if you have brainstorming sessions, maybe use actual stickies.

Galen Low: There you go.

Karen Chong: Maybe use actual whiteboard. That's a point I wanted to make- ... about stickies, because you are using a different part of your brains, and it's the physical action of putting something down and writing. It does utilize different parts of your brain, and you form neural pathways differently.

And with technology, we don't have to worry about rolling it up and having the stickies fall out of place anymore.

Galen Low: Right. Right.

Karen Chong: So do things like that. Use the opportunity to have the conversations. It could be the difficult conversations, it could be the less obviously work-related conversations, or, like, decision-making conversations.

And use this chance to... If you have to do creative, collaborative work, perfect. Use this chance to do that. If it's a planning, like quarterly planning or whatnot, being in person is so much more efficient. And yes, we do have tools, and yes, we are getting a lot better with using sticky whiteboard virtually, 'cause you can read people at the same time.

You don't have to exercise the ability to read nine squares at the same time. You, like, you're there.

Galen Low: Right.

Karen Chong: And, you know, maybe go to lunch together Hang out, after work drinks or whatnot. Just do something that you can't do, and bring meaning to bouncing ideas off.

Galen Low: Yeah. I really like your note about the Post-it Notes, 'cause even as I'm thinking about it, I'm like, even, like, rolling up Post-it Notes and butcher paper, and the awkwardness of that and how difficult it actually is, that's a shared experience, right?

You can laugh about it later. You can be like, "Remember that time?" Yeah, well, you know. Yes to the writing thing. I, I agree with you. Yes to the sort of physical, tactile things. It is a different thing. It's a, it's a different experience than a digital one. But even, like, those awkward moments or those, like, things you can laugh about later, like, I agree with you.

They sort of reinforce... They build that rapport, they reinforce these relationships that are deeper than work. And yeah, you're learning about people, you know, I wanna say firsthand, right? Like, our senses have evolved to sort of read these social situations in person, and that's part of what makes it richer.

Not to say that's the only way to do it, but I like that idea, that it sort of, you know, you're building these shared experiences. Build those shared experiences that, you know, leverage the tactile bits, the senses that you don't normally get to use together, and then bring that back with you. When you're back remote again, you have this sort of platform to stand on, where you could be like, "Oh yeah, I remember that time, you know, we tried to roll up the butcher paper and all the sticky notes went everywhere.

That was hilarious." And we know something about one another because of that, and we can use that to do better work together.

Karen Chong: Yeah. And because our academy is largely remote, we did get the chance to get together, and we did do planning reflection in, like, actual long paper, and we did exercises that reminds us of the shared experience.

We wrote, we wrote each other postcards from that destination.

Galen Low: Okay, I like that.

Karen Chong: Yeah. So it captures our emotions at the moment, and it helps us look back at it a few months, depending on when the postcard deliver. So it's intentionally creating moments that you share experience and remind you, you know, the time that we had together or the goals that we set a few months ago.

And I know, like, yes, we have these OKR documents, but I think humans are... We just glance over these things now because we've just seen so many of them.

Galen Low: Or, you know, I'm not sure if this format's gonna be supported in this thing. I need to r- reach out to engineering. But now you could just use AI and sort of ask and, you know, get the answer and keep going.

My question is, do you think that AI is making some of this remote work more lonely and isolated? And what are maybe some impacts that you've been thinking about that we might not even be seeing the evidence of right now? It might be years later that we actually understand the impact. Is there anything that is top of mind for you, like, in that area around sort of isolation and mental health?

Karen Chong: So if AI is used individually While it may improve our individual output, it sort of delays the collaborative thinking. So in your example, the dimension of this, or is it gonna be compatible with that? Unless you can somehow give AI all the information, all the context, what it gives you may be correct.

It may not meet what you're trying to do. So if it's in silo, yes, we all can get our own answers immediately, way faster than waiting for that person. It may not be what you need. So in that regards, yes, it may be more isolated. It may create more problem down the road. And also, let's say if you're gonna collaborate and everyone has their polished answers generated from AI, and then they came together.

It may be polished, but again, it may not work together. So delaying that initial brainstorm, like just throw random ideas out. We're losing that. And also, like we still solve problems collectively. It's very rare for one person to be able to solve this problem single-handedly without talking to anyone, or just curating from documents that this person could find.

It rarely is the answer. So it's, in that regards, you're delaying the collaborative thinking, and may create more problems.

Galen Low: I love that bit about problem-solving as humans, and that in isolation on your own you might not solve it the same way. And I, I think the other thing you, you said there that I think is really important, and it comes back to that rapport, right?

Is like, if we don't leave anything to collaborate on, then we won't be collaborating at all. If everyone comes with their 100% done, 100% complete thing where they've gone, you know, Claude or Chat has helped them generate some ideas. They did the brainstorming and blah, blah, blah, and then went through that whole process, and now it's like 100% complete and ready to merge with the rest, and then it's just like this stream of like deliverables that come together, and there's nothing to collaborate on.

And I like that idea of, yes, we also need to be intentional about creating opportunities to collaborate because just doing our own thing and then like assembling them at a certain point isn't really collaboration and won't result in the same kind of ideas and innovation. You know, not just that team spirit, but also, you know, different ways to solve the same problems instead of just, you know, doing it in isolation, like using that creative energy to maybe arrive at something even better.

And I think that is what is important about the collaboration bit.

Karen Chong: Yeah. And don't forget, AI is good at generating what's the most likely to be right answer.

Galen Low: Yes.

Karen Chong: So it's not great at coming up with brand-new ideas. So depending on what the nature is, what you're trying to solve, sometimes the most safe answer may be what you need.

But if you really... If you need something creative or something that's out of the box or no one's ever done that before, AI is not the place for you to get a final product. It can help you spark ideas, so... And that happens with collaboration.

Galen Low: Love that. Karen, thanks so much for this. Just for fun, I wanted to ask you, what is one part of the remote experience that you wish you could solve but you haven't solved yet?

Karen Chong: There are things that I find difficult. Like, this is this is a funny comment, not the real answer. Yeah. Like, I don't know I can find the energy to wake up two hours earlier just to get to the office. Yeah, so that's just a funny comment. But things that I want to solve but haven't solved is how can we enhance thinking and working creatively?

Like, creative work, I haven't solved how we can replicate the working on creative projects together. Yes, we have brainstorming. We do asynchronous and synchronous, like, sticky exercises. It's still just someone synthesizing it. But in, in person, the group may be doing it together. I know we can just try it t- to have the group doing it together, but I think two people trying to grab the same sticky at the same time digitally- is different. I don't think that's possible, first of all. But it's that. Like, the fact that these two people grabbed the sticky at the same time but want to move them differently, that surfaced something. That surfaced, oh, does this really belong in this phase or this phase or this category or what problem it is?

So working on collaborative creative thinking is something that I haven't solved.

Galen Low: I like that, and I agree with you. I think the sort of, the creative process, any creative process, and don't get me wrong, not just, you know, I'm not just talking design here. You know, creative problem-solving when it comes to code or testing or, you know, research.

I do think it's like, it's difficult to put in a 30-minute sort of calendar invite, and it's not always linear, and it's not always everybody. You know? Sometimes it's just like, "Hey, I wanted to ask you, like, does this belong here?" I'll walk by something and be like, "Oh, that's interesting. This has to do with that."

And they'll be like, "Oh, I didn't even... I hadn't even drawn that connection." Yeah, I think that's a really, really good answer. Better than my answer. My answer would've been time zones.

Karen Chong: Well, you have that problem too in real life. Like in, in person.

Galen Low: So universal time zone, artificial sun, right? It's 9:00 AM for everyone around the world somehow.

Karen Chong: Yeah. Yeah, time zone, it's something that it's not- Strictly and something that we have to factor into in remote versus hybrid, we just have the ability to collaborate with more people that we're not in close proximity to. I see that as a benefit. It introduce a lot more complexity as well, 'cause if you have different time zones, that mean you have different culture.

People interpret information differently in different parts of the world, so it's, you... As a project leader, another area that we need to spend more energy on is ensuring understanding, 'cause, yes, y- it could be s- different time zones of the same country, so the nuances is, the differences is less, but if you have Singapore, Israel, North America, those are three very different cultures that express and interpret information very differently.

So it's important to be mindful of that. Factor that into your communication. Factor that into your meeting facilitation. And it's another skill that is important, but even more important nowadays.

Galen Low: I love that so much, that idea of worthwhile complexity. Yes, it's a pain in the butt to get everyone, you know, scheduled for a meeting, but gosh, how wonderful is that?

The opportunity to work with bright people, you know, in every corner of the earth. I think that's the benefit.

Karen Chong: And pick synchronous and asynchronous wisely and strategically. See what really needs a conversation, and if it's a conversation across time zones, maybe you don't need five people in it.

Someone can bite the bullet one time. That's right, yeah. And then we can take turns. We can take turns- ... to have late or super meeting for this time zone today, but next month we can switch.

Galen Low: We're sending you as a representative to the 5:00 AM meeting. You're welcome. It's a worthwhile complexity.

Karen Chong: Yeah, and it's just important to think of your counterpart as humans, too. Whatever you experience, they experience as well. If you don't like 5:00 AM meetings- You think ... neither do they.

Galen Low: Love it, love it, love it. Karen, thank you so much for this. Thanks for spending the time with me today. Where can people learn more about you? Where can they learn more about your podcast?

Karen Chong: So it would be the easiest to find me on LinkedIn, Karen Chong.

If you see multiple, search Karen K. Chong. Or if you search Karen Chong Abracademy, then you will find me. And my podcast is called Mind Blend. It's a podcast to help people live more intentionally. So it... Being intentional is a big thing that I advocate, and if you search Mind Blend Podcast, you will find it.

I am the only one, so no mistake there. And it's not only about career, but it's about different aspects of life. But a lot of those equip you with life skills that help anyone who's a project leader become intentional, effective project leader as well.

Galen Low: I love it, and I love the name, too, Mind Blend, right?

Just sort of like meeting of minds, different POVs. I can tell you're all about it. I love the podcast. I'll add the links to your LinkedIn and also to the podcast in the show notes. And Karen, thanks again. This was a lot of fun.

Karen Chong: Yeah. Same here. Thank you for having me.

Galen Low: All right, folks. That's it for today's episode of the Digital Project Manager Podcast.

If you enjoyed this conversation, make sure to subscribe wherever you're listening. And if you want even more tactical insights, case studies, and playbooks, create a free account with us at thedigitalprojectmanager.com. Until next time, thanks for listening.