Setting up a project – part one: How to set your Support Assistant up for success when executing a day-to-day or small scale project

Virtual Success Show

how to set up a project

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Episode breakdown

In part one of our two-part special, we explore the world of project management and take a closer look at how to set up a project and what it really takes, from both you and your support assistant, to make those day-to-day and small scale projects really successful. During this episode, Matt and Barbara step you through the methodologies that they themselves follow, and encourage and teach to others, when setting their support assistants up with new, day-to-day or small scale projects.

Milestones give you the feeling that everything is in flow.

In this episode

Matt and Barbara open the episode with a light chat before introducing the topic. Barbara shares she’s been busy mentoring staff and transitioning key people into leadership roles. Matt then introduces the focus of the show: part one of a two-part series on setting up projects, starting with the framework and methodology for handling day-to-day tasks or smaller projects.

Matt and Barbara note that many clients struggle with support assistants because they fail to clearly define success upfront. They stress the importance of getting the simple foundations right from the beginning, as this can make or break the support assistant experience. Using the “sharpening the axe” analogy, they introduce a set of practical steps—along with a real-life example—to guide listeners in setting up projects effectively.

Matt and Barbara emphasize that the first step in setting up a task or project is getting clear in your own head what success looks like before involving the support assistant. Matt suggests mapping it out on a whiteboard, recording audio or video explanations, and sharing these with the support assistant. Barbara highlights that many skip this step and jump straight into calls, which leads to confusion since the client often isn’t fully clear themselves. Using visuals, audio, or screen recordings helps the support assistant understand the client’s thought process, setting them up for faster and more successful execution.

Matt and Barbara explain that after clarifying the project, the next step is to send it to the support assistant with a deadline for setting it up in the project management tool (e.g., Asana). The support assistant organizes the steps, then notifies the client for review. The client should then check if the setup is accurate, logical, and complete. If adjustments are needed, a quick call is often faster than redoing videos or audios. Once everything looks good, the client signs off, sets a clear project deadline, and establishes milestone check-ins to track progress—especially for short projects that may require same-day updates.

Matt shares an example of delegating a branded notebooks project to his support assistant. He gave a clear brief with budget, design specs, logos, colors, timelines, and delivery details, then had the support assistant set it up in Asana. He reviewed the setup, confirmed nothing was missing, and required updates every two days to avoid delays. The project finished successfully, though the budget had to be raised, and they secured a preferred supplier for future use. Barbara highlights the importance of milestone check-ins—without them, a support assistant might delay tasks until the last minute, risking missed deadlines or budget issues. She stresses that while delegation is key, the business owner’s role is to provide oversight (5–10%) to ensure projects stay on track.

Matt and Barbara agree that milestone check-ins help entrepreneurs let go while still feeling in control. Matt says they provide oversight without doing the actual work. Barbara admits she’s a control freak but explains she can delegate effectively because she’s built structured processes with her team. This structure empowers her people to succeed while giving her confidence and peace of mind in letting go.

Matt highlights that “you can only expect what you inspect.” Milestones provide a simple way to inspect progress without micromanaging. He explains that quick check-ins, often just a few minutes via tools like Asana, keep projects moving smoothly and ensure accountability.

Matt explains that milestone check-ins vary by project but are especially vital for first-time tasks without existing systems or suppliers. Frequent updates allowed quick problem-solving, such as realizing early that the budget was unrealistic and adjusting it before delays occurred. He emphasizes involving the support assistant in thinking through solutions, not just following instructions. Barbara adds that milestone updates aren’t unique to support assistants—corporate leaders also report regularly to CEOs, showing this practice is universal for effective project management.

Barbara emphasizes that check-ins aren’t micromanagement—they’re standard practice even at the highest corporate levels. Regular updates prevent surprises that could damage trust, like a CEO saying, “Why wasn’t I told about this?” She stresses that milestone check-ins are about teamwork and leadership, whether in a large organization or a small business with just one support assistant. Matt agrees.

Matt recaps the framework for running successful projects with support assistants: start with clear instructions (via video, audio, or notes) and deadlines, review their setup in the project management system, refine if needed with a quick call, establish milestone check-ins, and hold people accountable. Barbara adds that this structure makes accountability conversations easy—there’s no room for excuses. They both stress that while many fail without a system, applying this framework leads to strong, scalable success with virtual teams.


Podcast Transcript:
Setting up a project – part one: How to set your Support Assistant up for success when executing a day-to-day or small scale project

Intro: Do you find yourself running out of time to accomplish your work? Are you spending time doing things that you’re not that good at? There are effective ways to outsource this task so you can focus on your business.

This is the Virtual Success Show. We bring the inside scoop on outsourcing success for entrepreneurs, by entrepreneurs, and now here are your hosts, Matt Malouf and Barbara Turley.

Matt: Hi, everyone. Welcome to another show of the Virtual Success Show. I’m joined with my wonderful co-host, Barbara Turley. Good morning, Barbara.

Barbara: Hey, Matt. How are you?

Matt: I’m well, and yourself?

Barbara: I’m really well. Thank you, thoroughly enjoying these shows that we’re doing.

Matt: They’re lots of fun, aren’t they?

Barbara: Yeah, they are, lots of insights.

Matt: Had a good week?

Barbara: Yes, a bit of a crazy week for me. I’m mentoring new staff members. I’m actually putting some of our key people into more leadership positions at the moment, so there’s obviously that transition from me directing them to them directing me, which is very interesting to do, actually. I’ve been enjoying it, but it takes time.

Matt: Excellent. I’m really excited about today’s show. Today is going to be part one of a two-part series that Barbara and I were talking about in how to set up a project. As we were discussing just before the recording, we were saying that there’s probably two distinct learnings here. One is around setting up a day-to-day task or a smaller task or project, and then there’s the methodology behind setting up a larger project.

What we want to do today in part one of this is just go through a framework and methodology on how to set up one of those day-to-day or smaller tasks or projects.

Where this came from, just over the last few weeks, I’ve just noticed a lot of our clients that are working with VAs are having some challenges in like, “Well, I’m not sure if this VA thing is working for me.” A lot of it is that they’re not communicating effectively enough upfront on what success looks like and how the VA needs to, effectively, tick the boxes in order to get the projects done. We thought it would be extremely valuable today to actually step you through the methodologies that Barbara and I use and that we encourage and teach as part of today’s show.

Barbara: Yeah, I think, Matt, I see that a lot with our clients, too. It’s sometimes to get the simple things right. With hiring VAs, we often talk about the more complex things of how to get success with teams and various things, but the actual getting the simple bits right in the beginning, like what we’re going to talk about today, can actually make or break your experience with a VA. All the other stuff then can augment that experience later, but if you get this stuff right in the beginning, it just makes all the difference.

Matt: It does. I think it was a Winston Churchill quote: “If I had eight hours to cut down a tree, I’d spend seven hours sharpening my axe.” I really just want everyone to understand, it’s the sharpening of the axe piece that’s critical for today.

Barbara: Yes.

Matt: What Barbara and I did in preparing for today’s show is we came up with some steps, and we’re going to take you through these steps. Also, I’m going to take you through a real-life example in how it works, and the steps for success in setting up a project.

The first step that we both agreed was vitally important is you have to get clear in your head what the task or project is and what success looks like. One of the ways I do this is, I’m very kinaesthetic. I’m always writing or drawing or mind mapping. What I’ll do is I’ll often get up onto the whiteboard, and I’ll get out of my head onto the whiteboard what I actually need the VA to do.

Then I’ll actually just create a little audio recording using voice recorder or DropVox. Then I’ll actually take a photo of the whiteboard with the audio, and I’ll send it through to the VA. That will often be how I communicate the initial parts of the project to them.

Barbara: I love that idea. You know what I find interesting about that step actually, Matt, as well, and I’ve done this, as well, is that often I find what people do is they don’t do this as the first step. The first step they do is they get on a call with their VA and say, “Hey, this is what I want to do.” Rather than first doing what you suggested there, make sure that you’re clear in your own head first of all what you’re trying to achieve and the steps that need to be involved to get there, because often when I do that, I find I’m actually not clear myself. I thought I was in my head, but when I try to map it out, I think, “Oh, I didn’t think of that bit.” There’s all these little pieces of the puzzle that you haven’t thought about, and that causes terrible problems later when you just throw the task at a VA and expect them to figure that out.

Matt: Absolutely. Listeners, I want you to keep in mind, it’s not about spoon-feeding your people. What you need to do is set them up for success, so if they can understand how you’re thinking and what you’re looking for in this project, you’re going to set them up for greater success. It will help with speed of execution, as well.

Barbara: Absolutely. Now Matt, with the audio, I think there, if people are comfortable doing video … I know I’m comfortable with video, so for me I was thinking a whiteboard and quick, whip my iPhone out and do a quick video. I’m actually pointing at the steps, and it’s connecting the thing together. If anyone’s keen to do video instead, I think that would work very well as well for a VA to visually see how you’re going through the steps and your body language and all that sort of thing along the way.

Matt: Absolutely, and another tool that I’ve used as well is where I might use Jing or Camtasia to do a quick little screen video as well, so that could work as well.

Barbara: Great.

Matt: The next step, obviously, is to send this to the VA, and you need to send it to them with a deadline for them to set the task up in Asana or whatever project management tool you’re using. What you want them to then do is take that audio, that video, and set up the project in Asana. Obviously, you’ve gone through it step-by-step. What you want them to do is, when they’ve completed that part, to notify you that the project has been set up in Asana, and it’s ready for you to review. Now, I think this is vitally important.

Then step number four in this is for you to then review the project in Asana. Look at the steps that your VA has included, and ask yourself, “Is that how I set this project up? Is there anything missing? Does this make logical sense? Is this going to get them to the outcome that we desire?”

Barbara: Yeah, I agree. I think, as well, one thing that you said there that I’d like to highlight. You said, send this to your VA, and then set a deadline for when it needs to be set up in the project management system, so we’re not even talking deadline yet on when the project is to be complete. We’re talking about the VA needs to organize this project in our project management system and get all this information in there so that I can have a quick review, just an oversight thing. Again, we’re not saying that you need to go in and micromanage everything your VA is doing, but you do have to have a level of oversight so that you feel comfortable. I just jump in and have a quick look and go, “Yeah, great. Let’s go. We’re ready to go.”

Matt: I think there’s two parts to that, too. If you jump in and you look, and the recipe for success is there for them to achieve this project, then you sign off. “Good to go. Let’s go.” If it’s not, if something’s missing, my thought at this point is jumping on a quick call with your VA can really speed things along. I’ve tried in the past doing additional audios and videos and the like, but often it can be a three to five-minute conversation that will just fill the gaps in.

Barbara: Yeah, a video at this point is too time-consuming, I think. It’s just, get on the call. Of course, there is the question of if there’s just steps that were very obvious missed, that’s a whole different issue and conversation for another show, with your VA. There may just have been some confusions or something in what you said or whatever, and you can sort that out very quickly on a call.

Matt: Yeah, or you forgot a step, a step that you do unconsciously without even thinking. That’s what you’ve got to remember. There’s a lot of these steps that are just habit for you that aren’t habit for your VA yet, so you’ve really got to step through. It’s getting into the step-by-step of this.

Once sign-off has occurred, then there needs to be a clear deadline for the project, together with then milestone dates for check-in. Keeping in mind for this example today, we’re talking about a shorter project, and so it could be something that you’re setting up that needs to be done by tomorrow, in which case there might be an end-of-the-day check-in just to let you know where things are at and that they’re on track. It could be certain parts of the project that you just need to sign off on in order to keep things moving forward for it.

I thought what I’ll quickly do here is just let me give a real-life example of something that’s going on for us at the moment, just to bring it to this point.

Then I’ll talk about the milestone check-ins.

We’re doing an event in a few weeks, and I want some A4 spiral notebooks that are branded for our event. It’s a relatively simple project, but again the VA hasn’t done this before, so what did I do? I got up on the whiteboard, and I’m like, “Okay, what we need to do is, here’s the budget that I want to spend. My budget is $500. This is what we’re looking for, A4 spiral notebooks with our branding on the front. You need to use these logos. I’m looking for this color on this one. There’s two different types,” so I’m giving them almost a design brief. I specify that we’ve not done this before, so I recommend getting three quotes. Don’t put a quote in front of me that is over the budget. If you don’t get any quotes that come within the budget, let me know. I was very clear that say if you got three quotes initially that were over budget, give me a call, and we’ll discuss. We may need to up the budget. I was very clear on the timelines for this. I was very clear on where they needed to be delivered to, and that then all got sent off.

That got put into Asana. I then, once I got that, reviewed it. There was nothing missing, and there was nothing I could think of at that point of time that needed to be added to the project. What we then quickly said is, “Okay, I need this done in the next two weeks. Please give me an update every second day, so I know that it’s getting done.” I know that with a project like this, that if we don’t hit the deadline, we won’t get it delivered in time, so it’s critical that I’m kept aware every second day, just with a quick update. We actually do it in Asana, so that message is coming through.

That project has now been completed. We had to increase the budget because, on what we wanted, we couldn’t find a supplier that could get it to us in the timeframe. We’ve actually got a supplier that’s going to do it for us moving forward with a longer lead time. And so what’s great is we’ve now got a systemized process for this moving forward, and we’ve got a preferred supplier that we’re going to use.

Barbara: You know, Matt, there’s a couple of things I want to point out there, just in listening to you talk through this. I cannot stress enough, and I know you’ll agree with me, the importance of the milestone check-in points along the way because what could happen with a project like this is VA looks at the deadline and goes, “Okay, deadline in two weeks’ time. Cool. I’ve got two weeks to do that. Let’s go over here and do something else.”

They’re prioritizing something else that they’ve got on their list or whatever and not realizing that we might not find somebody who comes in under the budget. Oh, no. What are we going to do then? We’ve got to have a discussion, increase the budget.

If they were to just leave that and try and think they could do it all in the last week, you may end up in a situation where you’ve got no suppliers. We haven’t moved forward on anything. So the check-in points are really important so that you can keep a project. Your job as business owner or the visionary or whatever is to keep a project. It’s just like the oversight part of the project. No matter how much we delegate, I always feel like saying to clients, “You can delegate so much stuff, but your job at the end of the day is the oversight piece, which should only be about 10% of the job, 5% maybe, but the oversight is the bit that gives you the feeling that everything is in flow, and milestones do that.”

Matt: And it gives you a sense of control. If you’re anything like me, you know I like to control everything. Letting go is one of the biggest challenges that I think, as entrepreneurs, I see a lot of us having, so the milestone check-ins give you that feeling of control in knowing what’s going on, without having to do the doing.

Barbara: I agree completely, Matt, because I will openly admit that I am the classic control freak when it comes to my business. Some people don’t understand. I’ve come to a point now where I’m doing very little of the doing every day at VirtualAngel Hub. People say to me, “How do you let go? You’re so good at letting go.” I go, “Well, I don’t really.” I let go within a structure so that my people have all their processes, and we have worked together on refining them, refining them, refining them to the point where they feel empowered to get success with it, and I feel at ease in letting it go to them because I know I’m controlling the process. That’s key… and milestones.

Matt: It just brings me to another point. One of my very early business mentors said to me, “Matt, you can only expect what you inspect, when it comes to business,” so the milestones are your opportunity to inspect. I get often some resistance. “Oh, that’s micromanaging.” You know what? It’s not. A milestone check-in doesn’t need to take you more than three minutes. I get a notification in Asana telling me that there’s a message for me, and it just keeps things moving forward.

What it enables you to do, too, and the example I gave, not all of the projects that we do have an every second-day milestone check-in. It depends on what it is, and I want to make that point clear, but what it enables you to do is anticipate where things could go. This was a first-time project. We’d never done this before. We didn’t have any preferred suppliers, any of that, so by having shorter check-in points, we can actually make decisions quickly together.

I say together because I didn’t just want it me tell the VA what to do. I want them to think. We bring our people on to think, not so that we have to do all the thinking. What was great was you can move with speed. We didn’t get caught up. We weren’t caught out with, “Oh, my God. We can’t find anyone within budget,” because otherwise, they could have just kept looking and looking and looking for two weeks and say to me, “No one’s come within budget.”

Whereas, I think it was four days, we identified that we weren’t going to come in within budget. I can’t remember the exact number. I think it was five or six quotes, something like that. We just needed to tweak the budget in order to get the project done.

Barbara: You spotted a fairly major issue early on.

Matt: Correct.

Barbara: Which could have derailed the entire project. You know, Matt, I think it’s good to point out here, yes, we’re talking about working with VAs and virtual teams here, but I have held very high positions in big corporate institutions, banks and things like that before, and we still had check-in points. Like, we would have to update the CEO on milestones of projects, where we’re at with stuff. Not every day, but at a minimum weekly, and as your position grows and you go up to Director and that sort of thing, you’re updating the CEO every couple of days, sometimes every day.

Matt: Absolutely.

Barbara: I want people to realize that this check-in stuff is not about micromanaging a VA that’s just an assistant-type person. This happens at the highest levels in every corporate institution, where big teams are relying on each other to get projects moving. The last thing you want to hear from a CEO is, “Why was I not made aware of this?” That’s like the death knell for somebody at that role. Something goes wrong, the CEO is like, “Excuse me. Why was I not aware of this?”

Matt: You don’t want to know what the next conversation is.

Barbara: You don’t want to be in that situation.

Matt: That’s right.

Barbara: Yeah, I just wanted to make that point here, because some people do feel like, “Oh, I just don’t have time for all this micromanaging.” This is not micromanaging. This is about working as team structures together and leading your business, even if it’s just you and one VA.

Matt: Correct.

Barbara: That’s my little two cents on that one.

Matt: So if I was just to recap on all of this, let’s just quickly run through the steps. Number one, you need to get clarity in your head and communicate that effectively through to your VA, whether it’s through a photo of a whiteboard, a video, an audio, something that gives clear instruction and really shows that you’ve thought about how this needs to play out and what could potentially go wrong. You then need to send that to them with a clear deadline on when they need to get that into your project management system.

Once that comes back, then you need to review how they’ve set the project up in the project management system. If it’s been set up the way you believe is going to be successful, sign off on that, and allow them to move forward. If it hasn’t, if there’s some steps missing, or they’ve misinterpreted some things, or you’ve thought of other things, jump on a quick call with them, and go through those last few things to get it set up.

Then make sure then you have milestone check-in points. They will vary from project to project, but make sure that they’re very clear and you’ve given some thought that how often do I need to be communicated with on this project to enable it to move with speed and to be successful. Then, the last point there is holding your people accountable to those deadlines and those dates.

Barbara: Yeah, but you know what, Matt? If you set a project up this way, that’s such an easy conversation.

Matt: It really is.

Barbara: “Why was I not made aware of this,” as we discussed, conversation, and there’s no excuse. You can’t hide anywhere in that then. There’s no, “I forgot or I got delayed,” or anything like that because you’ve already set this thing up the way it should be done.

Matt: Exactly. I hope that’s helpful for everybody. One last thing is just to take some time and think about the framework that we’ve created here for you today. Work out what’s the framework for you. Is it the identical one that we’ve proposed, or are you doing something slightly different? If you’re doing something that works that’s slightly different, I’d love for you to be able to share that below or in our Virtual Success Show Facebook Group. That would be fantastic. As always, we ask if this is helpful, please share this with those in your community because we’re really dedicated to helping entrepreneurs all around the world succeed with their virtual teams.

Barbara: It is a tricky thing. As you and I both know, Matt, we have seen a lot of people fail with it, so it’s not as easy as people think when you don’t know how. When you do know how, and you apply these things, it is so useful, and it can be explosively successful for your business. We’re imparting this every couple of weeks on the podcast. We’ll put the steps in the show notes as well. Just the step-by-step framework, you’ll see that below the show, so you can just take that if it works for you. Yeah, I’d love to hear from you if you’ve got some other suggestions about what you’re doing that’s getting success.

Matt: Until next time, Barbara, have a wonderful week.

Barbara: You, too, Matt.

Matt: We’ll join you all shortly on Virtual Success.

Barbara: Thanks, bye.

Matt: Bye.

Outro: Thank you for listening to the virtual success show. If you found this show helpful, take a moment to share it with a friend so that we all grow together. Find out more with the insides scoop in outsourcing success by going to our website, virtualsuccesshow.com.

Until next time! Thanks for listening.

 

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