Why Siimon Reynolds, one of the world’s leading high performance coaches for CEOs and entrepreneurs, is using virtual teams for many key functions within his highly successful business
Virtual Success Show
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Episode breakdown
In this episode, Siimon Reynolds, mentor to business owners worldwide, shares his own experiences with using virtual teams and how using virtual staff for many vital functions within his business allows him to keep his business running successfully, as a 24/7 operation. This episode is full of insights from Siimon into how to effectively use virtual teams to create business success.
- Why having a team of virtual ‘specialists’ is so beneficial to your business
- Deciding whether full-time, part-time or project-based staff work best for you
- The advantages of virtual teams versus local teams
- Managing the challenges of working across time zones
- How to get over the ‘hurdle’ or fear of thinking virtual teams won’t work for you
- How important it is to have very clear processes in place for your virtual team
- The importance of regular communication, both verbal and written, with your team
Without systems, processes, and teams, you can’t create the entrepreneurial freedom you’re after or grow an epically large company.
In this episode
00:00 - Introduction
Matt and Barbara welcome Siimon Reynolds to the Virtual Success Show. Matt shares how he first met Siimon in 2008 when Siimon had just moved from Australia to Los Angeles. He highlights Siimon’s success in running his coaching business in the US while managing a virtual team in Australia. The episode focuses on exploring Siimon’s experiences with virtual teams, the roles they play, and how they support his business.
01:46 – Key team players
Siimon shares that he has worked with a support assistant in Australia for many years who manages scheduling, finances, research, travel planning, and both personal and business tasks. He also has a virtual salesperson in California who handles client calls through his coaching business, and a graphic designer in the Philippines who creates slides, logos, and brochures. Additionally, through another business with Matt, he works with multiple support assistants for design and CRM tasks.
04:34 – Part-time vs. Full-time vs. Project-based
Siimon explains that none of his team members are full-time. His assistant works about 4–5 hours daily on weekdays, his designer in the Philippines works anywhere from zero to around 15 hours per week depending on workload, and his salesperson averages about one day per week while also working for other clients.
05:25 – Advantages of virtual teams over local teams
Siimon chooses virtual teams mainly for cost savings, access to high-quality talent, and flexibility. He values being able to delegate tasks across time zones, which allows work to be done overnight and shortens turnaround times. Another advantage is not having to hire full-time staff—he can outsource as needed, making virtual teams both efficient and cost-effective.
07:30 – Challenges of working across time zones
Siimon notes that time zone differences with his assistant in Australia can be challenging, sometimes leaving gaps in availability. He suggests an ideal setup would be having trusted assistants in different countries ready to cover 24/7 needs without full retainers. All his assistants work from home, which he sees as a benefit since many talented people prefer remote work for lifestyle reasons. He cites IBM’s workforce model—about 60% outsourced—as proof of the growing appeal and success of virtual teams.
11:40 – ‘The Hurdle’
Barbara asks Siimon about a common hurdle faced by early-stage entrepreneurs and solopreneurs: the fear that support assistants or virtual teams won’t work for them. She highlights how many end up reverting to doing everything themselves, and seeks his advice on how they can overcome this barrier to grow their businesses.
12:30 – Getting over ‘The Hurdle’
Siimon explains that entrepreneurs can either hire support assistants directly or through agencies that pre-select and manage them. He recommends the agency route for beginners, as it ensures quality, efficiency, and easier onboarding. He also advises studying the support assistant industry—reading blogs, forums, and resources for a few hours—to build confidence and learn how to manage support assistants effectively.
14:43 – So I have a support assistant, now what?
Barbara highlights that once the HR side of hiring a support assistant is solved, success often depends on having clear processes and systems. Siimon agrees, stressing that support assistants aren’t “set and forget” solutions—like in-office staff, they perform best with defined processes, regular check-ins, and accountability systems. He adds that building such structures not only improves support assistant efficiency but also strengthens the overall business.
16:40 – Good relationships
Barbara notes that clients succeed with support assistants when they focus on clear processes, build strong relationships, and connect the support assistant to their business vision. Siimon agrees, emphasizing that support assistants should be treated as valued team members and that effective leadership and engagement are just as important virtually as they are in person.
17:33 – How proactive should my support assistant be?
Barbara raises the issue of clients feeling support assistants aren’t proactive enough and asks where the line is between implementer and strategist. Siimon explains it depends on how they’re hired—ad hoc support assistants need clear direction, while those with set hours can show more initiative. He adds that even if business owners must provide extra leadership and planning, the benefits of support assistants far outweigh that effort.
19:56 – The art of communication
Siimon shares that he meets his support assistant Tanya for lunch whenever he visits Australia, which strengthens their bond though it’s not essential. They email daily and aim for three short phone calls a week to stay connected, since relying only on email can feel isolating. He stresses the importance of scheduling regular calls to maintain smooth communication. Barbara then asks him if it’s possible to grow a company alone.
21:39 – The more you grow, the better people you need
Barbara asks if it’s possible to grow a large company and achieve entrepreneurial freedom without systems, processes, and teams. Siimon replies it’s essentially impossible unless the business is fully automated. He stresses that growth requires people, strong processes, and fair compensation, noting that true success comes when a leader makes themselves redundant by building a self-sustaining organization.
22:52 – Wrapping things up
Barbara and Matt thank Siimon for sharing valuable insights on support teams, noting how beneficial they’ll be for listeners. The episode wraps up with appreciation from all three and an invitation for the audience to keep listening, commenting, and engaging with future Virtual Success Show episodes.
