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In Episode 9 of Discussing Stupid, host Virgil Carroll is joined by co-host Cole from High Monkey to break down a frustrating reality of modern work: the overwhelming number of collaboration tools that don’t actually improve teamwork. With so many platforms—Slack, Teams, ClickUp, Figma, email, and more—why does collaboration feel more chaotic than ever?
Virgil and Cole explore how the abundance of tools often leads to scattered conversations, lost information, and inefficiency, rather than better collaboration. They discuss real-world examples of how context gets lost in endless message threads, how teams juggle disconnected platforms, and why no single tool seems to solve the problem.
As the conversation unfolds, they dig into why the issue isn’t just the tools, but also the processes behind them. They explore what effective workplace collaboration really looks like, sharing insights on how teams can reduce tool overload, set clear communication guidelines, and establish a single source of truth to prevent chaos.
To close, they offer practical takeaways on improving collaboration—whether through better workflows, tool integration, or just picking a platform and sticking to it. Listeners will walk away with a clearer understanding of why collaboration is broken and what steps can actually make it better.
Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com
(0:00) - Intro
(1:24) - Modern collaboration: Many tools, little clarity
(4:00) - Why the "perfect collaboration tool" is a false promise
(7:30) - The path to streamlining collaboration
(12:00) - It's about strategy, not just software
(15:00) - Outro
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>> Virgil: Hi, everyone, and welcome back to the podcast. As always, I am your host, Virgil Carroll, and with me today is...
>> Cole: Cole. The one and only Cole from High Monkey.
>> Virgil: So, yep. Hey, it's just you and I today, so, getting, ah, a little bit further where maybe, maybe we'll be done with winter here pretty soon. I'm hoping.
>> Cole: I have no idea at this point. It might be - in Minnesota - it might be 55 degrees one day and below zero the next, so.
>> Virgil: Yeah, well, at least we don't have the cold that we did in January in that, so. But spring is almost sprunging. So with that, we have another, topic here. And Cole, what are we going to talk about today?
>> Cole: Well, we may should have done this one for Halloween because it's a pretty spooky one. Modern workplace collaboration. Right. We're talking about the state of that. you know, I understand that keeping, like, a project organized, it's pretty complex to do. You have, like, documentation, you have communication platforms to keep track of, tools. All this stuff is like Living in different areas and different platforms. But, you know, amidst all this complexity of managing a project, right, you want to make sure the collaboration is streamlined, but with all these tools that are out there, right, you have all these things living in different tools. How can people do that? You know, how can you keep workplace collaboration streamlined with all the tools that are out there these days? So that's kind of the, thing I wanted to bring up to you today...
>> Virgil: That's a good topic.
>> Cole: And see if that induces any rants off the top of your head.
>> Virgil: Yeah, no, that's an interesting question. I guess first probably should start by, you know, for all the people that listen to this about the web. You didn't mention the web, so they might be all like, oh my gosh, what are we doing? Well, a good reminder is High Monkey also works in the collaborative space, as well. But even more so, modern workplace collaboration isn't just about, you know, kind of internal things. It's the way not only that you communicate internally, but also with your customers. And I know when we talked about this subject, we kind of talked about how, you know, the, the thing of like, you know, participating in a thread, in a discussion, and how when you're participating with that thread, you answer something and then you walk away and you do something and then you come back and you see that the somebody responded like 10 posts ago. And you try to answer that and then, you know, everybody else in the post feed takes, it out of context. Where that happens a lot in, in the workplace it even happens more on like social media posts and that where people are trying to have conversations and maybe even argue and fight, of course that never happens on social media posts - nobody argues and fights - but, you know, if they did, they, they might completely lose the context and one person is answering another and they're lost. And just how confusing it is, not only from just the way you do something in one system, but also just the sheer number of tools that you need that you can tend to have these conversations across.
>> Cole: Yeah. So do you think, this issue is more on the tools themselves? Like, have we not found the perfect tool yet? Or is it more on people's internal processes around managing complex, collaboration endeavors?
>> Virgil: I mean, that's easy. It's both. And I mean, you kind of can look at it, you know, both ways, but you, you know, looking at the tools, I mean, you know, even just, you know, earlier this week I was talking about how, you know, as we go through the process of rebuilding our own website, I was kind of looking at new tools because our website isn't that complex, I wanted something a little bit simpler than the normal CMS. And you know, I may mention to you that, you know, this one tool over here does this really well and this other does this really well and this does it there then I hate this about this and I hate this about this and I hate that. And it's like, why can't they just all get together and say here's all the things I like in this tool and make it! Well, it's the same with collaborative technologies. I mean everything does something very well, but there are no technologies out there that do everything well. And you know, part of the problem is both that they all kind of have their differentiator or something that they're trying to do to be, you know, different than the other guy. Which isn't necessarily helpful to end users, it's more about it. But the other thing is, you know, especially when you start talking about us purchasing this stuff and us investing in this, we tend to get really caught up in the bells and whistles that we never use. And so, you know, you tend to be very much motivated by feature driven type activities. So all the cool things this thing can do and it's like, oh man, we'll do that way down the road. And then you never do it. And that's part of the problem. So there are no good tools. On the other side when you talk about people, it's just about processing. I mean everybody's tried a million different ways. I mean if you just look at like a standard chat or something like that, you know, you kind of have inline where everything just kind of follows one after, the other and a lot of times conversations get lost, knowledge gets lost. There's all the different problems there. And then you have, you know, the others that do threaded, you know, where, where you know you're going down a thread, and again that's really great but sometimes the context is lost inside that thread because those threads get really long. There's been a lot of different ways they've tried to do it. The reality is there is no silver bullet. There is no app that you can get out there that's going to be like, that's going to meet all our needs. what it probably comes more to is, is the way people do things and, and the way they communicate and, and you know, kind of having some standardization around that.
>> Cole: So unfortunately, what I'm gathering is, there's no perfect tool out there that's going to fix all of my problems when it comes to how I internally collaborate.
>> Virgil: Well, if there is, you need to let me know what tool that is because I've looked at thousands of them and I have yet to find one. And, and this is getting to be such a big problem for organizations, not only internally, but the way they communicate with their customers and prospects and everything externally. Communication is so haphazard and so everywhere now, there's just not a lot of ways to be able to consolidate that down into something that you can get true meaning out of.
>> Cole: Right. Which is, you know, kind of unfortunate. But how can people begin to like, fix this mess? Because there's, you know, there's obviously organizations out there that do collaborate, pretty efficiently. And how are, how do you think they're managing their collaboration? Are, how are they unifying and centralizing all this information? You know, is it about creating like a one source of truth? Is it about like what, what do you think about, fixing this mess?
>> Virgil: Well, again, I think, I think from the standpoint of internal communications, you're really looking at pick a tool and stick with it. And, and that's kind of part of the problem is that a lot of times what happens internally is, is organizations pick, a tool. You know, when you talk about communication, you have the Slacks, you have, you know, Teams and you have all those kind of chat apps, that kind of go there. And a lot of times organizations don't really pick a tool, they let people use a lot of different tools, and so you don't really have a consistent platform that you're going through. The other thing is, and something we seem to be very afraid of is educating our people and actually helping them understand how to communicate better. I think sometimes it's because there's this general impression that if we try to educate them, we're trying to treat them like kids and that they don't understand it and that there's going to be some kind of cultural thing around that, when in reality it's just kind of, doing it. And it's why, you know, kind of when I do education things with customers and that I don't focus on the what to do, but why you should do that, which I think is really important from that is understanding why you should do communication in a certain way or why you should use the tool and how that's going to benefit not only you, but also the people you're communicating with in the organization you're in. External, it's actually kind of the opposite. The reality is, you know, as an organization, if you're communicating with your customers on social media, you can be on TikTok, you could be on Facebook, you could be on you know, X and, and Instagram and now BlueSky and you know, YouTube and all these things. You can't really pick an app and be like, okay, we're just going to be professionals at communicating with people from Instagram. Definitely from a marketing team, they may be more focused, on a particular medium. You know, I see a lot of them that you know, are more fixed focused on. like TikTok and Instagram, kind of more visual medium versus you know, X and you know, LinkedIn or something like that, which is more of a, you know, less visual medium and that. But from there there's actually the opposite side and we even use one ourselves where you have these consolidation tools where you bring all your inboxes into one tool and you kind of manage it so that you're kind of managing it in a central location. It's not the ultimate answer. The biggest thing is there is what organizations really need to look at is when they're having long threaded conversations and communicating back and forth is really top of that in doing it. I mean we've all seen instances throughout, especially the last several years, with all the things that go across social media about how fast organizations can completely lose control of their message and the conversation they're trying to have with their customers, and the people in general and they really have to have a plan around that to kind of encompass that and pay attention to it. So the days of us just being able to put out a post, you know, on any social media and then like come back to it a couple days later and see what happened is really going away. It's, it's a constant interaction, a constant management of that and being able to head off some of the bad and enhance some of the good that goes along with that. But from there you really need tools that are going to help you kind of bring that all together and not overwhelm yourself.
>> Cole: Yeah, I mean there's just too much information out there and too many things to keep track of to have all these different tools, not working together and not you just gotta manage those well. And it seems like a trend here in what you're saying is it's important to, it just seems like it's important to keep the tools to a minimum. Assign, you know, a role for each tool and, and stick to it. Really just stick to it and not keep adding the tool mess. Adding to the tool mess.
>> Virgil: Yeah. I mean, you know, and honestly, it's very much easier said than done. I mean, that's kind of the reality of it. I mean, I remember many years ago, working with a very large global customer and, they were migrating, their desktops from Windows me. So that tells you how long ago this was. Like in the mid 2000s, mid to late 2000s, to Windows XP. And part of that process is they had to look at the over 100,000 apps that ran across the organization. 100,000. And to make sure that they were compatible once it moved from me to Windows XP, that it would be compatible with that. Back in the day, that was a much bigger problem than it is today about backwards compatibility. And so we work with them on a project basically to help them evaluate the 25,000 most used, and again, look at this, the 25,000 most used apps. And it was amazing how many of these apps were, had basically the same function. Just this group over here in Europe, use this in this group over here in the US use that one and this one. In Asia, use that one and this one. And you know, the Pacific Rim, use this one. I mean, it was always this kind of thing that happens. So that's why I say it's kind of easier said than done. But overall, you know, it's patterns and practices that you're really looking at, which is you're trying to set up for how you're managing things, why that's going to help you, and then kind of figuring out the what you're going to do after that. And, and that's kind of where organizations need to kind of, take a step back. Or if you're just inside a team and you're just trying to do in that, you need to kind of figure out why you're going to do that. Whether it's external communication or internal communication, you're really trying to figure out, you know, what are you trying to accomplish with this and how you're going to accomplish that and really putting in that place before you start just jumping into new tools, from that side. But the reality is, from a conversational stream standpoint, I'm not sure there is a good solution, except you have to pay a lot of attention, because there's just no tool out there that can really help you do that. I mean, it is one of the areas that they start talking about AI being able to help is be able to, like, do summaries of conversations, that kind of stuff. So there's some value there because where, you know, I tend to knock AI for a lot of different things. That's actually one thing that I've seen that AI does very well is like, you know, when you use it to like, summarize a long document or summarize a long conversation or something. So you could definitely use it for that.
>> Cole: Yep, seems like there's some good applications for AI in those ways. But, you know, just make sure that your, your content is good before you really dive into AI or else, you know, who knows what they could come up with.
>> Virgil: Right. Yeah, I mean, it's a big topic, not very easy to talk about in a very short podcast.
>> Cole: Right.
>> Virgil: But I mean, hopefully people kind of understand that, you know, this is something you need to take a hold of and you need to realize is a genuine issue inside most organizations and, and the way we, communicate internally and externally. So, with that, thanks for joining me again, Cole. these are always great.
>> Cole: Yeah, thanks, Virgil.
>> Virgil: From that and, looking forward, because actually I think our next episode will be episode 10. So we've actually hit, gonna finally hit that magic 10 number
>> Cole: It's a milestone!
>> Virgil: Season 2. I always laugh we say season one and season two, that were only five years apart, but, you know
>> Cole: Hey, only five years.
>> Virgil: All right, thank you everybody. Appreciate you joining us.
>> Cole: Yep, see you next time!