Developing Members of Your Remote Team Successfully



In this episode of Bootstrappers, we discuss best practices for onboarding, offboarding and developing remote employees for the most successful outcomes. Don't miss these tips and tricks!

Jeremy and Gwenn talk about the best technology for ensuring that passwords and private information is kept safe. We then dig into the best practices for onboarding new remote employees and how critical a good experience is for the success of a new employee. We also discuss the biggest mistakes managers make with onboarding and offboarding employees, and how to accurately calculate the cost of turn over with remote staff members. Additionally, how to set high expectations from the beginning and what key information should be covered on the first day of a team mate’s initiation to your company. Developing remote employees can sometimes be a challenge. We discuss how best to help remote workers contribute to the vision of the company and how to hold them accountable. It is all on this episode of Bootstrappers!




  • 03:20​ The Importance of Implementing Security Protocol, Practices and Awareness
  • 05:40​ The best way to manage passwords - LastPass
  • 07:00​ We explain why employee onboarding has a long-term impact
  • 13:30​ Software clarity. Make a list!
  • 18:30​ How to hire employees that resonate with your company culture
  • 19:10​ Dressing for success - Why it’s important to get dressed while working from home
  • 20:24​ Tips to prepare for a virtual meeting
  • 21:40​ Is Real-time communication vital to remote working?
  • 24:20​ How to clearly communicate responsibilities and set realistic expectations
  • 26:20​ Remote Professional turnover cost VS domestic employees
  • 30:00​ How to address conflict avoidance in a remote workspace
  • 34:00​ Difference between a Virtual Assistant and a Remote Professional
  • 36:00​ Traction, quarter goals, rocks and how to measure progress and team development
  • 40:00​ Taking the virtual connection to an in-person meeting
  • 43:30​ GIVEAWAY: Trillion-Dollar Coach: The Leadership Playbook of Silicon Valley's Bill Campbell



Gwenn and Jeremy Aspen are co-founders of the property management company Anequim, and previously worked at the Wistar Group. They live in Omaha, Nebraska with their two daughters. Gwenn Aspen is the president of Anequim LLC, which sources virtual assistants from Mexico for the real estate industry, and provides operational support services for property management companies across the US and Canada. Aspen previously was the quality assurance manager at Wistar Group in Omaha, Nebraska which manages > 1,200 doors. She and Jeremy host The Bootstrappers Show which focuses on topics that are important to entrepreneurs in real estate related industries. 

Jeremy Aspen is a principal and founder of the Omaha based property management company Wistar Group, and the back office support company Anequim LLC. His career began in the international supply chain, an industry that required methodical and precise execution of processes in order to deliver automotive, technology, manufacturing and retail throughout the world. The best thing about him is that he's married to Gwenn and that he has the opportunity to raise his two daughters Christine and Amelia.