Project Planning 101: A must listen for Asana, ClickUp, and Monday Users

If your project planning feels like throwing tasks into Asana, ClickUp, or Monday and hoping for the best, we need to talk. That’s not a plan—it’s a recipe for stress, delays, and way too many “Where are we on this?” messages.

In this episode, Alane Boyd and Micah Johnson are keeping it real about why so many teams struggle with project planning, and how to fix it. No fluff, no corporate jargon—just simple, practical steps to help you take control of your workflow and actually get stuff done.

Here’s what you’ll walk away with:

•  💡 Why dumping tasks into a list isn’t the same as real project planning.
•  💡 Easy ways to structure workflows so things don’t fall through the cracks.
•  💡 How to stop bottlenecks before they derail your projects.

If you’re tired of last-minute scrambles and missed deadlines, this episode is for you. Let’s get your projects on track, hit play now!

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Transcript

0:00:00 - (Alane): Welcome to Automate Your Agency. Every week we bring you expert insights, practical tips, and success stories that will help you streamline your business operations and boost your growth. Let's get started on your journey to more efficient and scalable operations.

0:00:18 - (Micah): All right, Alane. So one of the things that we see all the time, and we used to be guilty of it as well, is just dumping a bunch of tasks into a project and then saying, cool, project planning done.

0:00:33 - (Alane): Yeah, I'm actually running into that kind of right now with. Because we're defining some new processes at the company and I'm seeing like it's just a task list for a bunch of different things and there's no order or, you know, some things need to be grouped together. So I'm feeling that pain right now.

0:00:53 - (Micah): Yeah. So let's talk about what is our standard process to overcome this. How do we actually do project planning so we're not just throwing all those tasks into a list, calling it done and then wondering why our projects aren't getting done on time.

0:01:09 - (Alane): Yeah. And project planning feels like a really formal word for it because it could be, it could be something really small. It could be something that Maybe only has 10 steps to it and that is a project within itself. And it doesn't need to be a one time thing. It could be something ongoing that just needs to be used every time you have this thing to.

0:01:30 - (Micah): Yeah, yeah. So even if it's designing like a project template for a 10 step process, like you're saying. All right, so I will say most people have the first step which is throw everything in to a project, all the tasks, just get it out there. Treat. If you're using Asana or ClickUp or Monday, treat it like a whiteboard. I would also say, and I forgot to mention this a second ago, do this with a project team. Do this with the people that are doing the task.

0:02:02 - (Alane): Yeah. Because you might forget things. It doesn't need to all be on you to identify those things. And being messy in the beginning is okay. Like you're saying, get in there and just document everything in, in tasks so that you're not forgetting it and then you can work from that. But if you're trying to do both at the same time, which is get everything down and organize it, you, you almost can't get done with it because your brain is overloaded.

0:02:29 - (Micah): Yeah, 100%. Like I, I, you know, I've seen the mistake happen. I've done it myself. Where you want it to be very linear, if you like. I think about designing a project or a process or the steps. Right. You go, all right, we're going to do this and then this and then this and then this. Then you're focused more on like, well, what are these specific things and how do they all connect and like, what are the dependencies?

0:02:55 - (Micah): And then you get to the end, you're like, oh, crap, I forgot to put in this whole, you know, sub step of what's going on here. And you're going back to the drawing board. So the important thing is just get you and the team, get all the tasks, ideas, all the task ideas out of your head and in a big list. Start there, just don't end there. That's the, that's the big issue. Once you have all the tasks out there, you can.

0:03:29 - (Micah): You'll naturally start seeing groupings of these tasks. So it might be like, I don't know, a phase in a project or like a first category of it, but you're. You're kind of initially looking for like these natural groupings of the tasks that you've thrown out there.

0:03:48 - (Alane): Yeah. And one thing that I'm seeing that I'm doing is kind of merging a couple of different things that we do together in the process. And I'm not saying everybody needs to do this, but it's been helpful for me. So I want to share is I'm very messy in the start of a process. And I've got several new projects that my team and I are leading. So messy is the name of the game right now. But we're starting to define what the steps are that we want to use and the flow of it, because those are two different things, is the steps in the flow. Because some things can happen simultaneously between different team members.

0:04:24 - (Alane): Some things need to depend on the other person. And so we're getting really messy. We're identifying what the process is. We're throwing tasks into the project. And now I'm having one of my team members do a process map of what we're doing so that, okay, we've got everything happening. We know what we want to do, but I need to visualize how this flow is going to happen. And so we're process mapping it so that we can improve the project in the next phase of this.

0:04:58 - (Micah): Yeah, so that is. That is a. You're doing the advanced project planning mode where you actually go out and process map it. But I would say for normal process planning and project planning, you don't necessarily have to go all the way through the process map in the beginning. Right. You know, so you've got your tasks, you're grouping your tasks. Optionally, it does help doing a process map, but that is definitely advanced. Like I think, you know, maybe you're feeling like that's natural because we've done it so many times now. And you see the benefit of like if we look at this in a map, then it's really helping us identify what the flow is and how it works together and how tasks have dependencies and different things like that. Now if you're using a tool like Asana, there's an easy shortcut for this diagram which is once you have your project tasks all outlined and even start grouping into things like sections in Asana, you can actually go to a timeline view and drag and drop your tasks and then start connecting them with the dependency nodes in Asana.

0:06:11 - (Micah): And that essentially gives you like what you're talking about with diagramming, Alane, is really important because that's essentially the next step is you and the project team need to sit down and go, well, like, how do these tasks fit together? What's the duration of these tasks? Like, how long is it going to actually take us to do this? And this is where I see. And I don't know if you're running into the same thing, Alane.

0:06:33 - (Micah): This is where I see so many people get very, very optimistic. I would say where they're all optimistic. Yeah, I'm the same, I'm the same way. Like I'll look at 20 tasks, I'll be like one day.

0:06:47 - (Alane): Right?

0:06:48 - (Micah): That's each task is five minutes. Right. But if you were to sit down and communicate that with your team or ask your team, somebody should stand up and be like, that's not a five minute task, that's a two hour task. And here's why.

0:07:01 - (Alane): Yeah.

0:07:01 - (Micah): And somebody else is going to be like, the second task is just a week long task because of all these reasons. And suddenly when you thought you could get this original project done in one week, you're now looking at a three or four week project and you got to kind of set that optimism aside. Are you running into the same thing?

0:07:23 - (Alane): Well, some, somewhat. And optimism. Some things are realistic, that it is a five minute thing. But what we're not taking into account is the other five minute things that they have in their day. You know, this one project isn't the only project that they have. So, you know, you don't want a bunch of yes men that are telling you like, hey yeah, this can be done in this timeframe. Like you really do want some reality checks when you're doing this and especially if you're not part of the process and you don't know every step.

0:07:55 - (Alane): I don't know, I don't do every step. Even though I see what the steps are, I don't do them all. So by perception might be way off on accurate time management.

0:08:06 - (Micah): Yeah, yeah. So whether you're doing a process map or doing a timeline view on a tool like Asana, the whole goal is to have that realistic expectation be set. So you know, all right, task one, worst case scenario, this is going to take a week. Let's account for a week. So we're not accounting for a day in the project plan and then it takes a week. So be conservative, account for kind of the worst case scenarios on these tasks.

0:08:39 - (Micah): Create dependencies across these tasks and you're, you're all. If you were to just do that consistently across your projects and your project templates, I would guess you'd increase the like timeliness and accuracy of project deadlines by 50%.

0:08:58 - (Alane): Yeah. Because you want the accuracy there whether you think it should be shorter or not. You need that accurate so you can plan capacity, that you can set client expectations. And so Micah, you know, for, for process mapping, this is a huge project. It's a three month long project. So you know it. I think it's valuable from what we do by, by doing that because I've learned so many times by trying to shortcut it and go, no, no, we don't need to do that. And the pain that it takes 10 times longer when you don't do that. But for short stuff, you know, a ten task project, I don't need a process mat for but this is what I see consistently from the transition of I've got the tasks all lined out to what a workflow actually is. There's this gap here and my perspective, and I'd like to hear yours, Micah, is the lack of using statuses.

0:09:53 - (Micah): Yeah, I would say there's a, there's a few things that I see. So statuses are probably the biggest. But then right behind that would be people forget to assign tasks. So you have this project and like you could have statuses but they forget to have that discussion who is doing this? Who's responsible for this? So even on a ten step process. Right. Or a ten step project, if you don't define the assignee of each of those 10 steps then guess what, it's not going to get done. It's just going to sit there and you just spent all the time creating a good timeline for the project.

0:10:37 - (Micah): But everybody is going to look at it and go, well, that's not my, my responsibility.

0:10:43 - (Alane): So I'm just going to ignore that. They're wanting to just take on a bunch of work like, oh, I'll take that one, and I'll take that one. Everybody's going to have the assumption that somebody else has taken care of it and they're going to go about their day.

0:10:54 - (Micah): And, and I would say too that the discussion with the team for assigning tasks and as like responsibilities is just as important as getting real on the duration of tasks and the project in itself. Because a lot of times people go, you know, that optimism creeps in and people go, well, I, yeah, I could do, I can do all of this, but you have to have that real conversation. Somebody's got to stand up and be like, Micah, really, you're, you're going to take on 80% of this project and we're going to do 10 of these projects? Like, no, you're going to get overloaded.

0:11:32 - (Micah): You don't have the capacity. It's not realistic. And at that point then you have to make the decisions on, well, who can do these other pieces? If somebody's just keep volunteering, I'll do it, I'll do it, I'll do it. That's generally a red flag that things aren't going to get done correctly. The capacity limit is going to be hit for a certain person. So those are the things that I would look out for and then secondarily. And this kind of happens depending on what tool you use, but dates on the, on the tasks themselves.

0:12:05 - (Micah): So when you're mapping out a project, right, you have your groups, you have your tasks, you have your dependencies, you have your assignees, you have the dates and you have the status of where things are at.

0:12:17 - (Alane): Yeah. The best way to align some of this, especially with an assignee on a task, is if you, if it's a repeatable project or a repeatable task, creating a template for that and you can have who is responsible for that. So you're not going in every time to a 25 part project and manually hitting each thing on who is assigned. And maybe things change. You can update the template, but you can also update the project or the task whenever you use it. So that can be a huge time saving there by having some starter information into the template so that when you use it, you're not redoing the wheel every time.

0:13:02 - (Micah): Yeah, 100% agree with that. I think the temp templates are huge, well designed Templates using these types of strategies make a huge, huge difference to the success of the projects themselves that you repeat. And that, that way too, like I had a conversation about this earlier today is if you're using a template to execute on specific things within your company, then when you need to make changes, you're changing the template. You're not retraining every, every person on the team to get this done. It's all there.

0:13:37 - (Micah): You know, you train the person how to use the, or the people how to use the template and when the template changes, no problem.

0:13:44 - (Alane): So it's funny that the templates are there and I find very often people will avoid updating the template and just make edits to the lot when they use it instead of just taking the extra few minutes to go update the template so that it is accurate. And then when you go to use it, you're not having to make edits, but people will feel like it's more work to go and update the template. Or maybe there's a knowledge gap on how to update it, but that is something that teams will avoid doing and just keep reusing the old version.

0:14:20 - (Micah): And there might be a responsibilities issue with that too, Alane, because, you know, I see that with teams where some people are scared to make those updates because they're not the decision maker, but then the decision maker hasn't really established the policy or the procedure to update it. So then the decision maker doesn't update, nobody's updating it. They all, yeah, have this out of date template and the team's going, well, what the hell is this for?

0:14:50 - (Micah): I'm not going to use that. It's easier making it from scratch now. So there definitely should be some sort of responsibility and policy on. Is it okay to update it? I would caution against that one because you don't want people having a smaller perspective on what's trying to get accomplished, change the template and break it for somebody else. But there does need to be a policy in place of, you know, when is it okay and who's responsible for making updates. And if you do need changes to a template, how do you request that from the person responsible?

0:15:27 - (Micah): All right, so, I mean, I think we, we covered a lot of various things in this, Alane. What if we try to bring this all together? And so essentially, right, the big goal of this episode was just to start thinking about project planning. And even though that sounds formal, it is so helpful just to get these little, little extra pieces in place so that everybody has that on the team and so really work with your Team. That's the number one thing that I see people make. The mistake is like, Alane sits down and is like, not that you're the one who makes a mistake, but just using your name as, as the example, sits down and creates a project.

0:16:09 - (Micah): Cool. But then the team members come in who are actually doing the work and go, what about this? What about this? What about this? What about that? And the entire project planning stage went, was a waste of time. So work with your team on project planning. Get everybody to dump, brain, dump the tasks. Organize those tasks in a group. Groups create a timeline or a process map of this project and then set realistic dates and timelines for the duration each step or each task will take.

0:16:43 - (Micah): Definitely look at assignees and dates and possibly even dependencies. And there is an art form to all of this, so it does take practice. So thing is, with business, we never run out of projects to work on, so he'll definitely have plenty of projects to practice on. But you know, start, start trying to test some of these things out internally and work with your team and get the feedback and have the discussions, responsibilities, time frames, tasks.

0:17:13 - (Micah): Just see how much it changes and how much it can improve. Just the ability to execute on projects on time or tasks on time.

0:17:23 - (Alane): That's such wise words to leave on Micah, where there's infinite number of projects in the company to work on so you can keep practicing and keep improving.

0:17:33 - (Micah): Yeah, well, we gotta, gotta make it a positive somehow, right?

0:17:36 - (Alane): Thanks for listening to this episode of Automate Your Agency. We hope you're inspired to take your business to the next level. Don't forget to subscribe on your favorite podcast platform and leave us a review. Your feedback helps us improve and reach more listeners. If you're looking for more resources, visit our website at BiggestGold AI for free content and tools for automating your business. Join us next week as we dive into more ways to automate and scale your business.

0:18:02 - (Alane): Bye for now.