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
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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.
- The importance of being clear in your own head around what the task or project is and what success looks like
- Tips on how to communicate your project goals clearly to your support assistant
- Why it is crucial to have milestone check-in points throughout the project, not just a finish deadline
- How you can work with your support assistant to hold them accountable to check-in milestones and deadlines
Milestones give you the feeling that everything is in flow.
In this episode
00:00 - Introduction
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.
01:58 - Steps for success in setting up a small project
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.
03:47 – Be clear on what you want
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.
06:27 – Clear communication is key
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.
10:18 – Case Study – sourcing notebooks for an event
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.
14:03 – A sense of control
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.
15:06 – “You can only expect what you inspect”
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.
15:40 – Overcoming project roadblocks
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.
17:35 – Having check-ins is not ‘micromanaging’
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.
18:28 – Wrapping things up
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.
