Want to be a more effective leader? Take our quiz to learn about your delegation style!

Visiting Boise: Leadership Lessons From the Field

Last week, I had the opportunity to visit our five virtual assistants in Boise, Idaho and not only did I come home with a heart so full, I also took back with me some valuable leadership lessons worth sharing.

With a completely remote workforce, keeping a good grasp on the needs, dreams, and realities of our team is a real challenge as a leader. Conversations happen on Slack, meetings take place online with short and specific agendas, and information is shared via email (or Loom videos!) Technology makes all of this possible, and our company relies on the innovation of these online communication tools. We have learned that embracing technology can truly bring us together in what might otherwise feel like a lonely affair.

Even so, there’s still nothing that can replace the meaningful experience that spending time with the people who are making things happen can bring. Here are three lessons I learned while visiting part of our remote team “in real life.”

Lesson #1: Investing in relationships with your team will remind you why you started in the first place

This isn’t something I necessarily struggle to keep in perspective, but no matter who you are, it can be easy to get tunnel vision when driving towards your goals. I went on this trip with the intent to truly get to know my team better. I want to know what is important to them, what motivates them, and how can I support and encourage them further in doing what they love.

I am fortunate that through this process I have uncovered more layers of commonality and commitment within our team. I can also see how many of our values align in areas that are not even related to business. This particular visit also allowed me to meet many of their families. If you really want to know how your team members feel about you and your business, have a conversation with their spouses! I don’t think previously I fully grasped the magnitude of how much Trusty Oak plays a role in their lives. The more I listened, the more I realized both the impact and responsibility I have as a leader. This fuels my passion for continuing to improve and grow Trusty Oak!


Pictured above: Cascade Raft & Kayak Guide, Casey Jones with Amber Gray (CEO), Kevin Chin (Elisabeth’s husband), Elisabeth Chin (VA), and Zeid Al-Ameedi (Kevin’s coworker) on the Payette River

Lesson #2: Creating space for time together with no agenda can be magical

I’ll start by saying that the opportunity I had with visiting the Boise team is probably not typical for most leaders, but even so, if you are able to do it, I recommend finding a way to spend time together with no agenda. Having the chance to see some of the normal daily routines, challenges, and interactions was worth a thousand words, but even more, the conversations we had organically resulted in dozens of new ideas for how to make Trusty Oak better for our clients and our team.


Pictured above, left to right: Emily Fisk, Hannah Lacy, Amber Gray, and Elisabeth Chin

Pictured below, left to right: Mesa Stevens, Amber Gray, and Hannah Lacy



Lesson #3: Sharing your vision is vital to growth

From the very first conception of Trusty Oak, I have had a vision to grow this company into one that provides a more reliable, flexible, and talented workforce for small business owners as well as better options for hundreds of individuals looking for work-from-anywhere employment opportunities. It has always been about the people, and lots of them.

But there are only so many people one person can lead alone. Even a respected leader with decades of experience and hundreds of employees does not do it alone. It’s necessary to cast a vision, empower and train new leaders, and extend trust. This is the basis for Trusty Oak and a key factor in our ability to expand our team. Today, I am leading a team of 23 virtual assistants and we’re interviewing more applicants this week. The numbers will continue to grow, and even now, new leaders are emerging from within our team. We’re still figuring out the structure and specific roles, but our approach is to work on it together.

I feel exceptional gratitude for these incredible people in my life and even further committed to the vision of Trusty Oak. I’m proud of the company we have built together and am full of hope and excitement for our entire team and for our clients. We’re making waves in the virtual assistant industry and bringing modern business solutions to small businesses across the country. We welcome you to join us in this great adventure! 

Learn About Our Services

Amber Gray

Amber Gray is the founder and CEO of Trusty Oak, an Austin-based virtual assistant company providing administrative and marketing support to small business leaders, authors, and creative teams. A people-first approach to hiring, along with a scalable growth model have positioned Trusty Oak as a flexible, dependable, and affordable alternative to hiring administrative and marketing employees. In 2021 and 2022, Trusty Oak was named Freelancer Hiring Platform of the Year, and in 2021 Amber was recognized as Austin Business Woman of the Year.

Before founding Trusty Oak, Amber spent five years at a rapidly growing digital agency based in Austin, TX. Four of those years, she was responsible for hiring and leading both local and virtual teams while working closely with clients ranging from CEOs to bestselling authors to build their brand online. As VP of Operations, Amber helped lead the company’s growth to #15 on Austin Business Journal’s Fast50 List in 2014.

As a female founder and leader of a company that has quickly established a recognizably special culture within a non-traditional workforce, Amber has energized and empowered women from diverse professional and personal backgrounds to go against the grain of historically standard female roles in business, technology, and leadership. Trusty Oak provides an opportunity for experienced admin and marketing professionals to work independently as freelancers, but with a supportive internal network consisting of other ambitious and resourceful remote workers.

Tag Highlights: