The quick and effective way to assess the success or failure of my Support Assistant
Virtual Success Show
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Episode breakdown
In this episode, Matt and Barbara talk about the quickest way to assess your support assistant whether they’re working out for you or not.
- The challenges of assessing an offshore support assistant, identifying the key areas you need to assess! Reviewing your onboarding procedure to make sure you are setting your support assistant up for success in their role. Continually reviewing and refining your processes.
The assessment tool isn’t to point fingers. It’s to be able to work together so that you get the best from this role and this person.
In this episode
00:00 Intro
The Virtual Success Show helps entrepreneurs improve productivity by outsourcing tasks they’re not skilled at, allowing focus on core business goals. Hosts Matt Malouf and Barbara Turley dive into real conversations about outsourcing. In this episode, a spontaneous pre-show discussion sparked the topic, prompting them to start recording mid-conversation to explore a real-world challenge Barbara brought up.
01:18 How do you assess your assistant?
Matt discusses a common question: how to measure an assistant’s success. He emphasizes the importance of simplicity and transparency in assessment. Overcomplicating the process leads to confusion. Clear, easy-to-understand metrics ensure both parties know where they stand. In this episode, Matt and Barbara share insights and open a discussion on effective evaluation methods for assistants.
01:52 Biggest challenges to assessing your assistant
Matt shares his method for evaluating assistants: start by listing their key responsibilities—like managing calendars, emails, or podcast production. Then, have them self-assess each task using a simple scoring system from 1 to 5, with 5 meaningful competence and confidence, and 1 indicating they’re struggling. This approach promotes clarity, self-awareness, and easier performance evaluation.
03:10 Identifying your key areas
Matt explains a two-part evaluation method: both you and your assistant score their performance on key tasks. Comparing these scores reveals perception gaps and sparks productive discussions. For example, if you score them a 3 and they give themselves a 4, you explore the reasons behind the difference and set goals to close the gap and improve performance.
06:55 Delivering feedback in an effective way
Barbara highlights the power of self-assessment discussions in uncovering hidden frustrations and misalignments. A task may seem well done, yet subtle issues—like constant clarification messages—can affect perception. This method fosters mutual understanding, encourages collaborative feedback, and reduces negativity. Matt adds that misaligned expectations often stem from unspoken assumptions, making these conversations key to improving clarity and performance.
Barbara expresses optimism for the outsourcing industry, expecting remote work and AI adoption to continue rising. She sees offshore staffing as a no-brainer, especially as businesses seek cost-saving strategies during economic downturns.
07:42 Identify KPI ‘s
Barbara notes that while using metrics-based KPIs is ideal, relying solely on them can overlook important nuances like individual working styles and communication dynamics. Real insight often comes from working closely together. She emphasizes that maintaining open conversations helps preserve the human element, allowing both sides to understand each other’s perspectives and build a stronger, more effective working relationship.
08:14 Assess your onboarding procedure
Matt emphasizes that performance assessments also reveal gaps in onboarding and training, often caused by rushed or incomplete instruction. It’s not about blame, but collaboration for improvement. Barbara adds that while this may seem tedious to entrepreneurs, it’s a crucial leadership responsibility. Investing in your team—even just one assistant—helps them become the right fit for your business and thrive.
10:17 Feedback
Matt emphasizes the importance of consistent, timely feedback, noting that without it, team members may wrongly assume they’re meeting expectations—or knowingly underperform. By comparing self-assessments with manager evaluations, feedback becomes constructive, not confrontational. Barbara adds that some may exploit a lack of oversight. These conversations boost clarity, accountability, and even confidence, especially when team members realize they’re exceeding expectations.
12:35 The stop doing list
Barbara praises Matt’s self-assessment strategy, featured in his book The Stop Doing List, and shares how her team now includes it in their automated review process. She notes it gives assistants a voice. Both she and Matt recall times when assistants rated themselves higher—and were correct—revealing miscommunication or misaligned role expectations. These conversations clarified responsibilities and improved mutual understanding.
14:46 Role expectations and communication
Barbara reflects on a past experience where unclear role expectations led to confusion, realizing leaders must communicate more effectively. She stresses that self-assessment isn’t about the leader’s rating always being right—it’s a dialogue. Matt agrees, emphasizing the importance of setting clear next steps and review timelines to ensure progress and avoid leaving the process unresolved.
16:04 Monthly assessments
Matt recommends quarterly assessments with monthly check-ins on key issues, scheduling focused training if needed. Barbara stresses that leaders must take responsibility for team development, especially early on, and shares how mentoring assistants is essential for growth. Matt advises keeping evaluations simple for better connections and results. They invite listeners to join their Facebook group, share stories, and subscribe to the show.
