Why some entrepreneurs struggle while others fly high when it comes to productivity success with virtual teams
Virtual Success Show
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Episode breakdown
In this episode, we tackle the big issue of why some entrepreneurs really struggle when it comes to getting productivity success with virtual teams. Having a great virtual team is like the holy grail when it comes to entrepreneurial freedom but sadly many struggle to really make it work. There are a few key things that typically trip most people up and in today’s show we give you someactionable tips to avoid the most common pitfalls.
- Why having the right systems (that actually work) is the key starting point for success.
- How to make sure your team have the right thought process as you when they are implementing your systems and processes.
- Why many entrepreneurs unwittingly set their teams up to fail … then blame them!
- How to foster true win/ win relationships with your virtual team & get explosive success.
Sometimes a mistake is actually a gift because it shows you where there’s a hole in the process.
In this episode
00:00 - Introduction
Matt and Barbara open the episode by greeting each other and sharing brief updates on their week. They set the stage for the discussion, highlighting that the episode will focus on challenges Barbara has observed with virtual teams and how they can help listeners understand and solve these issues.
01:21 – The scenario
Barbara shares a situation where the same support assistant worked part-time for two similar clients but received drastically different feedback: one client praised the support assistant, while the other was frustrated and dissatisfied. Matt and Barbara analyze the scenario, noting that the key difference isn’t the support assistant or tasks but the managers themselves. They emphasize that often, the business owner or manager’s approach and expectations determine the outcome, not the support assistant’s skills.
04:39 – Common pitfalls when onboarding your support assistant
Matt and Barbara discuss a common issue in both virtual and physical teams: business owners repeatedly hire and fire staff when things don’t go as expected, without examining the underlying problem. This cycle of frustration and cost continues because owners fail to reflect on where the breakdown occurs. They plan to provide a practical checklist or methodology to help listeners analyze and solve these recurring team challenges.
06:10 – Check your systems and processes
Matt and Barbara emphasize that when a virtual assistant isn’t delivering consistent results, the first step is to examine the system they’re following. Systems drive business outcomes, and people drive the systems. Often, issues arise from gaps in documentation, training, or process design. The key is to review the system from the support assistant’s perspective to identify where it’s breaking down.
07:42 – Don’t overcomplicate things
Barbara and Matt highlight that mistakes often reveal flaws or gaps in processes. Business owners may think their processes are clear, but in practice, they can be overly complicated with a large margin for error, leading to repeated mistakes. The key is to simplify processes and also teach team members how to anticipate potential issues, not just follow steps blindly.
09:11 – Regularly review your systems
Matt emphasizes that system issues often stem from training gaps rather than complexity. It’s not just about documenting steps, but teaching team members how to think while implementing the system. Regularly reviewing and refining systems prevents mistakes caused by cutting corners. The goal is to simplify processes, break them down, and set people up to succeed. Barbara then asks what to check next if the system itself isn’t the problem.
11:00 – “People run the systems…”
Matt suggests that once the system is confirmed to be sound, the next step is to evaluate the people implementing it. This involves understanding the team member’s perspective: Are they distracted? Properly trained? Communicating effectively? Competent? Aligned with the business? Barbara adds that staff will never care about the business as much as the owner does, so expectations about passion or attachment need to be realistic.
12:45 – Have a strong vision for your business
Matt emphasizes that a strong company vision and clear values help team members buy into the bigger picture. He notes that when a support assistant works well for one client but not another, the issue often stems from misalignment—either in values, company culture, or expectations. Barbara agrees, acknowledging the importance of this alignment.
13:32 – Expectations misalignment
Barbara and Matt highlight that misaligned expectations are a major cause of issues with virtual teams. Matt explains this often happens because core values and expectations are never documented or communicated, leading to assumptions. He gives an example of two business owners sharing a support assistant with very different management styles—one micromanages, the other is deadline-focused—showing how misalignment creates inevitable challenges. The key takeaway: be clear on your expectations and ensure your team understands them, rather than assuming they “just know.”
15:07 – It starts with you, the owner
Matt and Barbara emphasize that many team challenges—virtual or local—originate with the owner or leader. Matt points out that leaders are often overwhelmed with urgent tasks like cash flow, marketing, sales, and delivery, causing them to neglect “important but not urgent” tasks like defining core values and expectations. Barbara adds that the relationship between leader and staff plays a critical role in the outcomes a team achieves.
16:14 – Managing your relationships
Matt emphasizes that relationships are central in managing people. He notes that employer–employee relationships often fail because leaders focus on what they can get from their team instead of fostering a win-win dynamic that benefits both sides and helps achieve shared goals.
16:51 – Viewing your virtual staff as an asset
Barbara and Matt discuss the impact of how business owners perceive and treat their staff—whether virtual or in-office. Barbara notes that businesses thrive when staff are seen as valuable assets to grow, but when cash flow is tight, owners may unconsciously view staff as a cost, which negatively affects communication and relationships. Matt adds that cash flow pressures often make owners project stress onto employees, leaving them confused about expectations. Barbara emphasizes that this can create fear and self-doubt in staff, especially among Filipino support assistants she works with, leading to mistakes escalating as employees worry about their performance and job security.
19:26 – Am I setting my team up to fail?
Matt emphasizes that pressure leads to mistakes and highlights the importance of setting people up to succeed. He focuses on clear communication, especially with virtual team members for whom English may be a second language. A key technique he uses is having team members repeat back tasks—either verbally or in writing—to ensure understanding and correct any miscommunication upfront.
20:22 – Fostering strong communication
Barbara and Matt emphasize the importance of investing in clear communication with virtual team members. Matt shares a strategy he uses during high-pressure periods—prefacing his team about potential short, bullet-point instructions so they understand it’s due to workload, not a reflection on their performance. Barbara notes that short or sharp written messages can be misinterpreted, leading staff to feel inadequate. They conclude that communication issues often cause misunderstandings, and sometimes perceived performance problems are not the fault of the virtual team member.
22:09 – Let’s recap
Barbara and Matt discuss a framework for managing virtual teams that starts with ensuring business systems are solid, since people operate within them. Next, they focus on evaluating the person, looking at how they implement the system and understand training before assuming underperformance. Maintaining a positive, reinforcing relationship and clear communication is crucial to prevent misunderstandings. They also emphasize the importance of aligning values and expectations so both parties understand what success looks like. Matt notes that these principles should guide recruitment and performance reviews, forming the backbone of effective virtual team management, and helping to identify whether issues arise from the person, the system, or other factors.
24:42 – Wrapping things up
Barbara emphasizes that many issues with virtual teams stem from a lack of systems and processes, which are critical for scaling a business. She also highlights the importance of communication and the underlying relationship between business owners and staff, noting that unconscious attitudes—like seeing staff as a cost rather than an asset—can harm the team. Matt agrees and hopes the discussion provides actionable insights. Barbara shares that she found the episode very valuable and expects listeners will gain similar eye-opening realizations.
