Episode 007: Project Management Tools Won’t Save Your Team

Why do so many projects go off the rails, even when the team has the right tools?

In this episode, the team breaks down the real reasons projects become frustrating, delayed, and messy. They talk about authority, trust, delegation, communication breakdowns, notification fatigue, and why project management software often becomes a substitute for the hard conversations teams actually need to have.

They also share strong opinions on tools like Basecamp, ClickUp, Trello, Linear, Monday, Asana, Slack, and even Google Calendar, along with practical advice on how to lead projects more clearly and keep teams aligned.

If you lead people, manage clients, or feel like your projects are constantly getting stuck, this episode is packed with honest insight and useful takeaways.

Timestamps

00:08 Why projects turn into dumpster fires

00:29 Authority, trust, and setting people up to succeed

03:25 Unmet expectations are what break projects

05:24 Do great project managers delegate or just get it done?

09:00 How to decide what should be delegated

12:43 Are all project management tools trash pandas?

21:26 Do teams buy software to avoid hard conversations?

24:22 Notification fatigue and why people stop engaging

32:41 Best practices that actually make projects run better

34:45 Why AI-generated project briefs create problems

Transcript

SPEAKER_01 0:08

Okay, so Trevin, let's just start with the conversation. We're just gonna pick up. Um what's typically when you've been working on chair stuff, other companies, what's what's one of the biggest factors for why projects just become complete dumpster fires where everyone hates each other?

SPEAKER_03 0:29

I I feel like a lot of this comes down to authority and trust. So how example I give you a project and I say, go figure it out. Is that me giving you authority and autonomy? Or is that me just like completely abdicating my responsibility as someone who's supposed to be setting up that project for you? I would argue it's the latter because or sorry, it's the abdication. Yeah. Because you're not You're passing the buck. You're not actually trying to help them achieve anything. It's better if you're like, okay. David, you are in charge of posting the podcast by Friday. And you can have XYZ amount of resources to do that, but get it done.

SPEAKER_00 1:28

And here are the credentials to do it. That's my favorite.

SPEAKER_03 1:33

But it's like, you know, I I think about this myself a lot as a leader. It's like where am I under communicating the things that people need in order to achieve what I'm looking for. And also where where am I not creating the guardrails well enough for them to be successful within like a specific scope?

SPEAKER_00 1:59

Yeah, and I jump in uh a little bit here is I I think what I try to do, and I'm not a project manager, I've had to be one at times, like you know, like you said, but like it's if I give you enough instruction or detail around it, you should be able to hopefully hit the mark, or at worst, 85-90% of what I was looking for, um and then be able to know where to ask the questions. Okay, I have all this, I think I did it right, let me just double check because this this made me question something, whether it was design or functionality or or whatever you know is being asked of you, and not being afraid to ask that question for help. So it's it's even things just like, here's what I have, this is everything you should need, ask me if you don't know. And then you know, let the person or people fly. But a lot of times it's like, here's a dock, do the thing. Which part of the thing? The whole dock? Am I supposed to do that whole thing? Do I have a, like you said, authority to do that? Should I just build this page, this page and this form? What do you what are you expecting from me so that I don't overstep and do ten hours of work when you only budgeted for four because you thought I was only going to build a web page? Or I do underwork. I think you only want the web page when really you want the whole thing. You know, that kind of thing. And so I think it all comes down to clarity and communication from the AI agent. No.

SPEAKER_01 3:27

It's just it's just like any relationship, and specifically I'll have to speak of marriage. Unmet expectations. Unmet expectations are the single driver of most fights that occur in a relationship. And they're the single biggest driver of frustration with a project. It's I thought in my head that it was gonna be this, this is what it actually was, and that is where the mismatch comes, and that's where frustration happens. Where, you know, if you would have just told a client, hey, it's gonna be this date because of what you did, it they would have been fine with it. They could have, you could have managed expectations in advance. Instead, someone didn't communicate that to them. They did not communicate those expectations well. And so the client still thinks we're gonna have it by the original date, even though I got you that thing three weeks late. And now all of a sudden, when it's three weeks late, I actually launch. Now the client is furious because unmet expectations. And so I I think that's that's typically that's unmet expectations or mismanaged expectations start at the start. They it's part of the kickoff if it's not scoped well. It's one of the reasons why I have made pains in the past year with us, with clients, to be brutally honest at the start about what is and is not possible and what expectations should be for projections, for results, for timelines, to put a million caveats on if you don't deliver by this date, we can't do our job, right? And just to really set clear expectations that can feel a little bit labor-intensive at the start, but frankly, really help those projects go a lot better and keep everyone happier.

SPEAKER_02 5:08

Yep. So I have a I have a colleague who has a great quote that I'll put a bow on that. The the difference between expectation and reality is disappointment.

SPEAKER_01 5:18

That's it. That's great. I love that. I love that.

SPEAKER_00 5:24

Well, I have a question on here, too, because real quick on this. There are project managers and there are project managers. And what I mean by that is a true project manager will take information, make it all pretty in whatever software you've got, and then hand it to somebody else. Even if doing so would take longer than clicking the checkbox in the thing. Then there are project managers who sometimes do the thing and don't pass the information on because uh I can just do it myself. Which do you think is better?

SPEAKER_01 6:00

So essentially someone who just takes care of stuff or someone who just like like delegates to the nth degree. Is that kind of what we're asking here? Yep.

SPEAKER_00 6:09

What would you prefer?

SPEAKER_02 6:11

Which person is thinking proactively versus being told what to think. That's what I prefer.

SPEAKER_01 6:18

I prefer the person who does the thing and then tells everyone they did the thing. Can they add the caveat of like if it takes them a few seconds to do it? Yes, just do the thing, but please then tell everyone you did the thing so that we're it's like that. That's my ideal scenario is like, yes, if something takes you 10 minutes to do, but you're gonna have to write a 10-minute email to a team member and then follow, just get the thing done. Like, just yeah, just get it done. That's my preference.

SPEAKER_00 6:45

I agree. Get it done, then tell me you did it. Uh that I was gonna say that's that's the disparity is I got it done.

SPEAKER_03 6:51

Oh yeah, I forgot to tell you guys I did that, and now you've wasted four X time on I I guess the caveat is do you trust that person's discernment to decide whether or not that is something that they should be doing or not? Because I've definitely experienced that in the past where it's like, hey, you're a senior designer and you should be delegating that to a junior designer. Because I need your thoughts on concepting this new project versus designing an ad for this other project. Right.

SPEAKER_01 7:24

But if it takes you more time to delegate to the junior designer, is that actually a net savings of any time at all?

SPEAKER_03 7:31

Well, we can debate it.

SPEAKER_04 7:32

I mean I let's yeah, let's set some parameters here.

SPEAKER_02 7:37

Yeah. What is what is an appropriate situation for delegation? I know this is a project management, but I think it's a good topic.

SPEAKER_03 7:44

What is project management?

SPEAKER_02 7:46

What is what is an appropriate filter for delegation versus just do it? In your opinions.

SPEAKER_00 7:53

Yeah, I would say it doesn't waste other time. So like I get what you're saying, Trevin, there, like, oh, if I'm gonna do this 10-minute thing, but it's taking me away from 10 minutes of something else, well then I'm net losing potentially. Um I'm thinking about success rate when I say this. Like if I spend 20 minutes writing, hey, can you go fix the checkbox over here or whatever, and that person doesn't deliver or might ask questions while I then go back to the things that I'm supposed to be doing or delegating or doing high-level stuff, uh then the back and forth to me is a waste of time versus like, hey, fix the checks box, you don't have to do this, but in the future, this is how you do it. And I think it's the education practice for me that if if you do it, you have to show them how you did it so that you don't ever have to do it again. But I think I'm more talking so similar around that because yeah, there's some things like I could design that logo because I don't think they're gonna do a good job doing that, rather than giving them the opportunity to learn and be successful. I'm not I'm not as much in that camp.

SPEAKER_03 9:00

I feel that it matters that you define what success looks like on a thing, and so you all know the stakes, and that's super important in deciding whether or not you should delegate something. Um if the stakes are low, I would actually be more inclined to delegate that than less. If it's higher, maybe you shouldn't delegate it.

SPEAKER_01 9:25

Um I know that's not a perfect guardrail for how you decide to delegate, but I think it's a factor. I think it depends on the person that you're delegating to of like what are you like what's your I'm just taking it from a leadership angle. What's your goal for that person? If it's someone that you're trying to develop within the organization, then I think you need to give them as much as you can to develop them and give them shots to take things off your plate. If it's someone that you're working with that, frankly, is a contractor, that I like I'm not trying to develop this person, I just need to get it done for the sake of like speed. Okay, like just do it yourself. I I think a lot of it has to come down to yeah, what are you like, what's your goal for that person you're delegating it to, just thinking holistically about them outside of just the task at hand. But okay, yes, it takes me just as much time to tell them how to do it, and they may only do it 80% as well as me. But if they get to learn something new and I'm trying to develop them within our organization to have hundreds of skills like that that they've learned that now they're can replace me, then it's well worth the time. But it's a question of what's their role within the organization. Are they someone you're trying to build up, or are they someone who frankly is uh part of your cogs, right? That you're just like, hey, we just it's part of doing the business and we got to get done. And I don't really like love you, but it's transactional, right? Sort of a thing. Just get the thing done. Uh that that's kind of how I like to think about it a little bit more.

SPEAKER_03 10:53

How do you decide who to invest in on which things?

SPEAKER_01 11:00

Um that's a great question.

SPEAKER_02 11:02

Um how long you want to work with them and how often something's gonna happen.

SPEAKER_01 11:08

Yeah. That's a really good that's it, right? Yeah. Do you think this is someone that's gonna grow with your team for the next decade? And do you like, yeah, then absolutely. If you don't, and you're like, yeah, this person's here for you know, short amount of time, like yeah, they're they're a stop gap, then maybe not. That's I think I think it's more of uh an understanding of like where are they in the long-term like health of your organization.

SPEAKER_02 11:36

So I think it's also when it comes to to projects or tasks, how often that's gonna happen. Yeah, it's it, yeah. If it's gonna take me 15 minutes to do something one time, that's probably not gonna happen for another year. Just do it. Just do it, right. It takes you it takes you half an hour to teach someone or 15 minutes to do it, and it's not gonna recur. That's kind of my filter too, is yeah, it's not even capability or developing someone, but if it just takes me 15 minutes or it takes me half an hour to teach you how to do it, so in a year you can spend half an hour to do it and save me 15 minutes in a year from now. Yeah. Like it's just it's it's functionally better, even if it's net the same. It takes me 15 minutes to show you how to do it or 15 minutes to do it. Like, that's I should do it. But if it's gonna be something that I gotta do this every single month, I'll take 30 minutes to train you now, because then you can take it off my plate, you have more ownership, you have more responsibility, and I have one last thing to do.

unknown 12:25

Yeah.

SPEAKER_02 12:25

So I can focus on 15 minutes of doing something more meaningful for my business, right? Yeah, yeah.

SPEAKER_01 12:31

Let's let's shift a little bit. I want to talk about project management tools and the role that those actually have within an organization. Let's let's start off though by by talking about what some of the ones are and give me your hot takes on on how you feel about these as tools. So I'm gonna list some hot take before we go in.

SPEAKER_02 12:46

Okay. All project manager platforms are trash bandas.

SPEAKER_01 12:52

They're all awful.

SPEAKER_02 12:54

Everyone with the asterisk.

SPEAKER_01 12:58

Some are more trash.

SPEAKER_02 12:59

Project management platforms are only as good as the project manager managing the platform. So that's the cave. Like that's I think that's what I want to I want to make sure we all hear is there's no project management technology, no matter how good or well built it is, that's going to solve your project management problem.

SPEAKER_01 13:17

That is good. All right, so we're gonna go through the list. Uh first one up, personal favorite of mine, Basecamp. I'm gonna say it's solid and give it a thumbs up, even though David Schwab says that they all suck. Sucks. Okay. Why? Why don't you like Basecamp?

SPEAKER_02 13:36

Granted, I haven't used it in in a long time. It's just too elementary. For nine out of ten use cases, I've been I've been put in to use it for. I can't say I can't even necessarily say I've used it for what it's designed for. But when I use it, it's not capable of doing what I need. Alright, fair enough.

SPEAKER_01 13:54

Trevin, what say you about Basecamp?

SPEAKER_03 13:57

I think it's really good for like a dashboard level of whatever how a project is going. Um I think I tend to agree with David, though, on the whole, where all project all project management software is just terrible. It goes back to what we're talking about with delegation. It takes forever to set up a project in every single thing. It it's as much time as doing it. So this is like Basecamp aside, I feel that way about everything. So unless you have a project manager or someone, or at least let's just say that you have someone owning the project management. It doesn't have to be a project manager, technically speaking. You don't have to have that role on your team.

SPEAKER_01 14:47

You're doomed to fail. It doesn't even matter what the tool is. Here is here's my ideal project management software. Are you guys ready for it? Like this is this is my genius invention. Everyone works in the office together, and there's a massive whiteboard with one to-do list, and everyone uses Google Drive for file sharing. That's my ideal project management software. Right. It's just like everyone can see it. It's all up in one place, central in the office. You check things off as they go. Everyone knows what their tasks are, who's assigned, you just write it out, and then everyone's like, oh yeah, we're all the files. They're all in that one Google Drive file. Go.

SPEAKER_03 15:21

Okay, well, you can't you can you cannot achieve that unless you have high trust in the people that you work with and also high accountability around every task. Like everyone has to be every task has to be assigned to a single person who will be accountable for that thing. That's true.

SPEAKER_00 15:38

Yeah, yeah. Well, and I I think to your point, you uh the digital world allows you to turn off those notifications. So I've used Basecamp, I've gone back and forth to it twice. I think it's very simple, and I think it's good for very small teams and very little projects where you're doing most of the work. The moment that you have to invite two or three people in and you don't you haven't already standardized a process, it's not great. Okay. It's it's great for Basecamp level stuff where you're doing the same four things over and over again and you're assigning the same four to ten people over and over again. But beyond that, thumbs down.

SPEAKER_01 16:12

All right.

SPEAKER_00 16:13

Uh next up, we're gonna talk click up. Decent. I use it, so it's it's just also probably overkill unless your team's doing a lot of different things or large enough to handle it, or you do have somebody who's project manager mindset who can control all of you. And because you have to configure it too. So if if you don't have somebody who took ownership of the platform, uh it's it gets unwieldy, it gets unwieldy. But but I'd say it's pretty good.

SPEAKER_01 16:47

I just hate from a UI standpoint. Like, I'll give it a solid. We use it internally at share. Like, so like we pay the money. Uh I will say I I hate their user interface that I have seven menu bars to scroll through to figure out to find what I need. Like, can we please just like condense some of those menus into one or some drop down? Like, it's just it's a lot. Uh visually, every time I see it, it gives me anxiety.

SPEAKER_03 17:12

Yep.

SPEAKER_00 17:13

I'd agree.

SPEAKER_03 17:14

Amen. 100%. I kind of hate clickup, to be honest. It's just overwhelming. And uh I think it's as good as your processes. So if you have it all templated out and your process is there, it's great. I think it also comes down to whether or not you're gonna focus all of your communication around every deliverable in the platform of clickup because that's what it's good at. But if you like the minute that someone goes and has a side conversation in Slack, then like you're done.

SPEAKER_01 17:52

It's all yeah, you're you're done. You're done. It's it it is you need like militaristic adherence to click up for it to be great. Uh okay. Uh Trello.

SPEAKER_02 18:02

Uh are people still using that?

SPEAKER_01 18:04

I don't know. Alf teasing or whatever it is. I don't know. Next. Next. Okay, it's not a no. We're all no on Trello.

SPEAKER_00 18:14

Uh too easy.

SPEAKER_01 18:16

All right. So for this is mostly a more of a product tool, but I don't know, maybe people are using project management. Linear. Trevin, I know you love linear. Love linear for the use case of product.

SPEAKER_03 18:27

It's very good for that. Good for road mapping, good for you know, tracking tickets. But I mean, again, I'll just go back to the same thing that I said for clickup. Like you do need to keep all of your columns about each uh each issue inside the platform. Yeah. I don't know if I would use it for anything else. Yeah, that's fair.

SPEAKER_00 18:50

Yeah. No, I think it's clean and niche, and that's that's what's appealing to it, but it doesn't do everything else. I wouldn't call it a a full project management suite. I'd call it a specific dev project management tool. Yeah, project management.

SPEAKER_03 19:01

But I I feel like that's the shortcoming of most project management software. It's that everyone is trying to build a suite versus solution for a specific use case.

SPEAKER_01 19:12

Yeah, maybe that's like what actually we want is like project management for a like frankly, if someone was like, we're a project management tool specifically for marketing agencies, that would probably be more applicable for us than like just a generic clickup that's for everyone doing right. So so maybe that's just a a product that needs to be wildly verticalized to actually be an effective tool. Uh okay. How do we feel about Monday? Never used it. Maybe the biggest marketing budget in all of project management. Good lord, they're everywhere.

SPEAKER_02 19:44

I I would call it I would call it good software. Okay. But it's a Cadillac, right? Yeah. I don't think it's right for everyone. I do know a few ministries who are using it that use it to its full potential and it's really like it's really strong.

SPEAKER_01 20:01

Do they use it as a CRM as well?

SPEAKER_02 20:03

Because so not as a CRM, but as a data, like as a um, what's the term term I'm looking for? As a um a dam, digital asset management.

SPEAKER_01 20:12

Gotcha. Okay, cool. Because one of their big pushes is like, we're your CRM. And I'm like, wait, what? I don't want my project management tool to be my CRM too. Like that's weird. No, that's a that's a weird thing to try to do. Okay. So Monday.com. Yeah.

SPEAKER_00 20:24

Yeah. They're okay. And and also I think it also comes down to, yeah, exactly who's using it, because if you're not able to pay for the tiers or the types of users or guest users or things like that, that's where this gets expensive. Real expensive, real fast.

SPEAKER_01 20:38

All right. I have been in Monday before. I I thought it was pretty slick. Honestly, I liked it pretty well. I didn't spend a lot of time at issues with one client. I thought it was really solid. Uh let's go to the probably the most popular one I would say for most of the people listening, I would think, would be Asana.

SPEAKER_03 20:53

Is it as good as it used to be? I mean, I used Ayazy years ago before they sold it to Salesforce. Uh and it was good then. Yeah.

SPEAKER_02 21:03

It's it's good. We use it. It's yeah, it's good, but again, it's good if you set it up to be good. I think that's the asterisk we're putting on all of these, though, is like all of these. It's only as the software's only as good as the person pulling the the levers.

SPEAKER_03 21:19

Okay, so can't ask a tangent conversation. Yeah. Break it off. Do you think we buy software to avoid having hard conversations around projects? Yes.

SPEAKER_02 21:35

That's why 90% of software is bought to avoid having hard conversations about people or system failure. Yep. Absolutely.

SPEAKER_00 21:43

Yeah, it's because I can be like, look, the clock says this, I told you it was that, you didn't do this. AI bot now can tell you you're late.

SPEAKER_01 21:52

Right, right. Yeah, because it's like you you buy and you think, okay, if I just put the tasks in the project management tool and it sends auto. Automatic reminders of this person, surely then they'll actually do the thing they've been asked to do a million times that we'd said to everyone in the meeting, this is the due date, and then they'll do it. And yet they still don't do it. Right? Like it we you what we're trying to build is automated annoyance for our team.

SPEAKER_02 22:13

Here's a good question. Why? Why don't people do it if all the things are there?

SPEAKER_01 22:19

Because they're lazy, David.

SPEAKER_00 22:21

I I don't because they they wouldn't have done it before. I I would say that the reason we have a project management tool is is twofold. We're in the software world, so you've got the people that don't enjoy talking person to person, or like probably us, we've got fully remote teams. You can't talk person to person all the time and can't reasonably call people every five minutes and be like, dude, where's my money at? But um anyway. But so that that bridges that gap. But the other piece you know to it is okay, that task is up there. I'm not being watched actively. I'm not being micromanaged by a person like I would be potentially sitting in an office. I I have had somebody literally dictate an email that I should write for them. So it's wild. Yeah, that annoys the junk out of me. So I'm like, bring on the project management tool, just you know, give me a list of stuff I need to do and go away. But if I'm the person who's gonna get that stuff done, I'll get it done and I'll get it done ahead of time. But most people are still back in the high school, like, oh crap, it's due tomorrow, forgot to do my homework, and they cram, and you get media either mediocre work, lucky work sometimes, or none at all. And so I think it still comes down to the people using the platform. It's it's how they would have done work if left alone to their own devices. In an office. In an office. Trevor Burrus, what do you think? Why don't people use it?

SPEAKER_01 23:47

Or like why why don't they do this stuff even though they have all the tools in place to to like stay up on the project well? And we're not saying everyone, because like honestly, like I can say for our team, like frankly, I think our team at Share internally does a really good job of consistently like just doing the things that they're supposed to do that they, oh, this is a sign to me. Cool, I'm gonna get it done. Not perfect, like absolutely a team members who don't, but I think generally, like, like so this isn't everyone, but there are people. We all know the people within the organization that can get all the text reminders, can get all the slack messages, and still it's like, dude, we told you every way we know how to do to get done, and it's not getting done.

SPEAKER_02 24:22

I'm a project manager's least favorite person to work with. I so I the reason I asked that is I would say I think a big reason why it doesn't work is because we've gotten to a point where we have notification notification fatigue. If I get five text messages, two Slack messages, three Teams messages, two emails, and an Asana task notification for every single thing that happens, it's just impossible to keep up. And I think I think that's a fundamental world. Maybe not everyone is living in, but the particularly the more projects you're part of and the more things that you have to be managing or aware of, you get to the point where you just have notification fatigue and you you can't keep up with it, so you don't even try. Yeah. And maybe I'm just projecting my radical inequities on everyone else's side.

SPEAKER_03 25:15

I would agree because I think that it comes down to being overwhelmed. Like Matt, you mentioned that with ClickUp. You go into it and you're immediately overwhelmed just because of the layout of the tool.

SPEAKER_01 25:25

Yeah.

SPEAKER_03 25:26

So and then and then at that point, you're like, well, it's gonna take me 30 minutes to figure out what I need to go in here and what I need to do. And in that time, I could have done the thing that I know I need to do. So I'm just not gonna engage. Right.

SPEAKER_01 25:40

This is why my my ideal system is literally a whiteboard.

SPEAKER_02 25:48

I have one right here that has an entire quarter worth of projects.

SPEAKER_04 25:52

Yep.

SPEAKER_02 25:53

And I just took I took everything out of our project management, and once a week I meet with my team and I say, tell me where it's at, tell me what I need to do, and tell me what I need to do. I put it on my whiteboard, and then it gets done. Whiteboard, dude. Right? I literally I went out and bought a whiteboard and I run a digital agency.

SPEAKER_03 26:11

Just because I couldn't keep up with it. My favorite project management software is Google Calendar. I love it. Well, you can have a task, which is to the did I do it or not? You can have a block of time if it is something that someone needs to be invited to, where it's like, hey, this needs to happen at this time. Yeah. And then there's accountability around it. It's simple. Everyone gets one email. And at the end, everyone, especially if you share your calendar with everyone on your team, you can manage projects that way. I don't think that's necessarily best practice, but it's less overwhelming.

SPEAKER_01 26:54

I I will say, in terms of like helping team members who struggle with getting things done, I love the calendar idea to give them dedicated time to work on something and to encourage co-working with digital teams. Uh, we've talked about doing this internally, Trevin, where like, hey, let's let's put an hour, let's put two hours on the calendar together. And at the start of the meeting, everyone's gonna say what they're working on and what their tasks are to accomplish in the next hour. And we're just gonna shut off our mics and we're all just gonna work. And at the end, we're gonna update how do you do on getting that thing done. This is if you ever, if you never, you know, if you're a solo person working alone and you have a team who can do this, there's a tool called Focus Mate that is phenomenal for this. It literally pairs you with a random stranger at any time of your day. And all you do is go work together and you both say, here's what I'm working on, here's what I need to get done in the next 45 minutes. And then it you shut it off and then you report back at the end of it, here's what I got done. That's the only thing the tool exists for. But I think that's a great, like that is if you're looking at tactile ways to move projects forward, those sort of like interpersonal human hacks are some of the things that actually make the difference.

SPEAKER_00 28:01

Yeah. I was gonna say, I think some of this comes down to as well, like what we were talking about in some some other portions of this is um process, you know, other podcasts we've talked about process. So if your process is we have Slack, we have Slack and we have ClickUp. Okay, if it's just free for all, then yes, whatever you're more comfortable with is gonna happen. And a lot of times it's like, well, somebody's gonna say something in Slack, somebody's gonna do it in clickup, somebody in Slack is gonna go tell you to put it in clickup, and then you're gonna get a text message from somebody else who doesn't want to talk to the people in either. And if there is no clickup is for this, Slack is for this, nothing goes in between, or we've finally integrated both, so just get out of the other one, or what you know, whatever it is. If there's no process, it's only a matter of time. I mean, and could even be days, it could be just hours before somebody's made their own Excel sheet, somebody has a notes thing up. Like I got and I'll I'll just put myself on the chopping block. I take notes on calls. Why? We have AI note takers. Second, they're better than my notes. Third, we have clickup. Why didn't I take the notes in ClickUp? I took it on my notepad first, and then I stuck it in ClickUp and literally had my team go, why don't you put that in ClickUp first? Like, you know, that's true, we are paying for that. And so I think again, if process is loose around it, where it's just and especially if your departments or teams can find their own solutions and aren't on lockdown, like, wait, oh, you're using Monday.com? Who said you could do that? Delete, you know, like then for sure, no project management software is going to save you. None.

SPEAKER_03 29:38

Yeah, I think there's other things you can do from a process standpoint where it's like we meet at the beginning of the week if we're a fully remote team. We talk about everything that we need to get done during the week, and then we have a stand-up on Friday and we talk about where things are at. Yep. Because I think part of the pro problem with project management and the way that projects go off the rails is people don't feel like they can say that something is going badly and they don't feel supported when it does. So if you can if you can crack the code where you reduce the time between I got stuck and I told someone that I'm stuck, yeah, then I mean there's a huge percentage of your project lag that you can just eliminate because someone feels comfortable enough to fail.

SPEAKER_00 30:30

Should we create a project management tool called Are You Stuck that has a built-in? Is that what you're saying?

SPEAKER_03 30:36

Yeah. Well, I think uh I think Basecamp does this from a dashboard standpoint. It's like red, yellow, green, and it's like, oh, this is not trash, this is yeah.

SPEAKER_01 30:49

You know cool. Um we were going through just the list of tools and saying, are they good or trash panda? I I I just have a few more that I want to ask you guys about. Uh how do you feel about people running project management in Slack?

SPEAKER_00 31:07

I say it's possible, but why?

SPEAKER_03 31:11

I I love it personally. Uh because especially if you can I mean you're already communicating there. And it probably comes back to my thing that like my ideal project management tool is just a chat thread where I say, here's the task, and I can check it off. It's not dissimilar to the whiteboard, it just is digital. Yeah, yeah, just digital. It's a digital version of the whiteboard.

SPEAKER_01 31:36

Yeah. I get that things can get lost, but yeah. Yeah. So search history is for, right?

SPEAKER_02 31:44

Yeah. I think I think the the piece that I like about project management software the most that you would lose doing something like that is the the ability to go back and say why did something happen, right? To go back and be able to be like, why am I why am I three weeks, three weeks late on this deliverable and just finding out about it now? And then you go back and realize, well, it's been sitting on my desk to review for the last two weeks and I just failed to look at all the notifications I got.

unknown 32:09

Yeah.

SPEAKER_02 32:09

Or oh, it got stuck in design and we were stuck on this one thing and couldn't get past it. And oh, here's an idea. If we ever get into this process again, we have an alert if this happens multiple times, upgrade it or take it to the like whatever, right? So I think that's the piece that is most valuable that you lose not doing it in a platform built to manage projects. Yeah.

SPEAKER_01 32:31

Yeah. Um all right. So if you had to, this is just kind of a wrap-up question for us. If you had to simplify project management down to a few best practices and best principles, what would they be?

SPEAKER_03 32:44

Uh end every meeting with a who is doing what by when.

SPEAKER_01 32:50

That's a I mean that's that alone can save everything. Yep.

SPEAKER_00 32:55

And every post mortem on every every project, even if it's a quick one.

SPEAKER_02 33:01

Every task needs an owner, every project needs a champion, everything needs a due date. Yep.

SPEAKER_01 33:08

Those are three solid ones.

SPEAKER_00 33:10

Yeah. And post-mortem is the whole circling it back around because you can have a bad process, bad project, and if you don't take the time to say why, which is, you know, it's another set of tasks. It's another project management thing, saying, okay, now we have a due date to say what went bad, what went good, and why. Now let's refine so it doesn't the bad doesn't happen again. Um if we don't do that, then you're just gonna keep repeating the same mistakes.

SPEAKER_01 33:35

Yeah. I would I would say another like best practice principle that I would leave folks with is I think every project needs a clear internal team kickoff call just to work through all of the all of the back and forth logistics of how how we're gonna run this project before it actually gets into getting there. Like your first call can't be, all right, so we're we have this do this week, and here we go, let's end we're off. Like you need an internal team call to consolidate around it, give everyone context on the project, on why we're doing it, alignment around, hey, here's here's the the what success looks like out of this. I think a a kickoff call that actually aligns the team around the why, around the vision for the project, around what the real core outcomes are, why the timeline is what it is, like what happens if we don't hit that timeline? Um, I think that's as critical as actually running the project because it makes everyone understand, okay, here's why we're working on this. So that would be my big best practice is have an internal team kickoff call that actually sells a vision for why this project is important.

SPEAKER_03 34:45

Where I was gonna ask you guys is are you as concerned about the contextual anxiety as I am with people generating project briefs with AI?

unknown 34:58

Yes.

SPEAKER_03 34:59

Because they're just farming it out and not actually aware of any of the things that you said.

SPEAKER_01 35:05

Yes, a thousand percent. Because we have gotten those from clients, and it is so clear that they generate with AI because when you ask them pointed questions about what they asked for, they have no idea what you're talking about. Yeah.

SPEAKER_02 35:17

So are you ready to let a genius four-year-old write all over the walls of your projects? Right. Because that's effectively what letting AI do its job is.

SPEAKER_04 35:26

Yeah, yeah.

SPEAKER_02 35:27

I've I've spent the better part of six months trying to train AI to figure out how to write a simple project brief. And it's I I still can't get it to the point where I would call it the quality of a of a really green coordinator writing a brief. Yeah. It's really, really, really good at processing a ton of information and giving me insights to write the brief. Like I would I would let it write a creative brief if there's a resource and it's like, this is what you need to produce, this is what I need you to focus on, this is what I need you to pull out. I've done that where it's like I have a hundred-page impact report and I need to distill that into two emails. Find the best stories, find the most impactful stats, great. But if you said I need to write an impact report, oh my gosh, I spend more time fixing the brief that an AI agent would write than I do writing the brief myself, right? Um, so moral of the story, don't let AI write your briefs. Yeah. Or you're gonna get a lot of stuff you didn't bargain for. Yeah. I'd say go back to what was it, episode two, we talked about AI?

SPEAKER_00 36:30

Yeah, yeah. Well, that, and to your point, like even your on the client side, your RFPs, if you're if you're getting a proposal out there and you feed AI what we're looking for, there are times where it will add what it thinks you should have asked. And so it'll put that in there. If you don't read it, then you're getting a proposal from people going, oh yeah, we could totally do that for 80k. And you're like, that sounds, I guess, reasonable-ish. And then that's what we're going off of, because we're the ones on the receiving end. And then when we start asking for things that you're like, we don't even have that, or we don't want you to do that, it's like, well, that's not what we're doing.

SPEAKER_01 37:04

Well, that's in your proposal, right? Right, right. So always proof. Well, or Trevin who asked that, whoever asked that. Yes, about AI project management or AI uh scoping on projects.

SPEAKER_03 37:17

So yeah, I mean, I think Yeah. The concern is kind of more along the process side where we have been. And it's like, okay, we we don't really know what the process is anymore because we farmed it out so much that I don't even know how a project runs.

SPEAKER_01 37:39

Right. Because we let them do the whole thing. Yeah, that's good. That's good. That's a good word. Cool. Any other last thoughts on project management before we wrap for today?

SPEAKER_03 37:49

Uh I do have one more question. You can cut it out if you want. No, but what do you guys think of the concept of a pre-mordo? Where you basically take a project before it it picks off and you talk about it with the team and say, what are all the ways that this is gonna go wrong?

SPEAKER_01 38:07

I like it. My my gut is that like I can, if I let my head go there, I could spend three hours saying everything that I think could go wrong. I I I guess I would say I like the idea with guardrails. Like, what are what are the guardrails before we start really just going down like okay, well, what if the client decides that they're, you know, they want to scrap the project halfway through? It's like, okay, well, yeah, that could happen with anything, right? But um, no, I like the idea that like it it's that what do they call it in the military? Um red red teaming it, right? Is that what they call it? Where you essentially like figure out like, yeah, I think it's called red teaming. Uh if you're a military out there, don't murder me because I called it one. So either red team or blue team, something like that.

SPEAKER_02 38:48

Essentially the idea of like Are you thinking of red blue pill, blue flu? Did you just watch The Matrix? Is that what happened?

SPEAKER_01 38:54

No, no. Yeah. Uh it's essentially this idea where they do attack simulations where it's like, if the enemy hit our system, how would they hit it? Right.

SPEAKER_04 39:05

Yeah.

SPEAKER_01 39:05

And so I think I think that sort of thing is really helpful, which is like, if it goes bad for us, how's it gonna go bad? I I I love that actually. If you have time for it in bandwidth, like, you know, within reason, yeah, I love it.

SPEAKER_00 39:16

And maybe you simplify it to give me three ways, you know, everybody gets three three ways that it's going to fail in your area or something like that. Which I'll I bet half of them will write communication, so we'll get that out of the way. Yeah. But like if besides poor communication and poor you know, strategy as far as due dates go, what three things would kill or delay the project in your area? And it's good, because I think it'll highlight even in a post-mortem, like, did did any of those things happen? No, something new happened. All right, then let's address that. Um, but if one of those things did happen, that's even bigger accountability on my part. It's like, well, you knew it would, and we talked about it even before starting the project. So why?

SPEAKER_02 40:01

I yeah, I like the idea. I think it's only appropriate for one-off projects. Yeah, that's true. I don't think you should need to have a pre-mortem for like if you have a retainer client and you're doing the same thing every single month, month in and out, and you have to meet every single month to ask what's going on, you have a bigger problem than a pre-mortem. But if you're doing something you've never done as an agency, that that makes sense. But I would also say um it is it is the responsibility of the strategist or the leader on the business, the project, or the account to do most of that thinking for the team, right? Again, not if it's something you've never done before, but if it's a standard project with a few degrees of variance, the person who's running the project should be responsible and capable of predicting what are those barriers and how do we pre-navigate them without having to take the time of the whole team to do that.

SPEAKER_01 40:56

Yeah, that's good. That's good. I think in the right context, right? It can be really, really helpful. Love it. Good stuff. All right. This has been project management probably more than anyone ever wanted to hear on it, but that's okay. It I think it was helpful for everyone. It's uh got a log and thoughts on it. And uh yeah, thanks guys for for joining. We will be back again next week with another episode. So we'll see you guys then.