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How Women-Led, Values-Based Companies are Transforming Remote Work

Amber Gray

When I started my virtual assistant business in 2015, the remote-work revolution was in its early stages. I was looking for something more and dreaming of a business supporting ambitious people doing big things. Ultimately, I wanted to bring talented individuals together from all over to form a supportive, interconnected remote work community.

Today, more than five years later, the remote work world looks a lot different. More and more businesses are going virtual, and I’ve found that female founders and CEOs are leading the way with values-based best practices that provide the most benefit to workers and clients. The dream of Trusty Oak is very much a reality today, and I’m starting to identify exciting trends in the remote work space, especially for female leaders.

Values-based leadership is an alternative to the hierarchy-based leadership style often associated with the stereotype of the traditional CEO. Where hierarchy-based leaders lean on authority, ambition, and opacity, values-based leaders promote collaboration, empathy, and transparency. Today, a lot of women-led companies embody the values-based approach and are creating remote workplaces that surpass their brick-and-mortar cousins in both their ability to keep employees happy as well as their overall productivity. 

What’s the secret sauce? The short answer is supporting the person. The long answer is that although empathy and collaboration might come more naturally to many women, leading a values-based company still requires a lot of intentionality and effort, no matter your gender identity. 

In this blog post, I want to talk about how our values at Trusty Oak inform our culture and contribute to better experiences for our VAs and clients. I think the innovation natural to the remote work world allows us to break out of traditional molds that aren’t serving us anymore, and I want to tell you about how we’re doing that.

Hiring and Supporting the Best Talent 

Members of values-based teams tend to report lower levels of work stress and higher levels of job satisfaction. At Trusty Oak, our reputation as a great place to work allows us to attract world-class VAs. We consciously seek out freelancers who we know will be a good fit for our culture. They bring to the table not only the skills on their resume but also their integrity, authenticity, and commitment to following through. 

Many people are drawn to remote work in the first place because they value work-life balance. The exciting thing about hiring freelancers to work on a fractional basis is we can look beyond the traditional candidate pool and work with incredible individuals who aren’t looking for a 40+ hour work week. Many of our virtual assistants are students, work-at-home parents, professionals who want to travel and work abroad, or driven individuals with several side hustles going. Little by little, interconnected remote teams like ours are challenging the accepted assumption that climbing a corporate ladder and working a 40 hour week is the only way to be successful. 

Related: The Extinction of the 9-to-5

Motivating with Trust and Empathy

Motivating a team can be challenging. Typically, hierarchy-based leaders resort to negative tactics to increase productivity. Traditional leaders also use motivational tactics that may seem positive, such as rewarding team members for working excessive hours of overtime, but that in reality have a major detrimental effect on quality of life. 

Our philosophy is different. We believe that our shared values at Trusty Oak provide a built-in incentive for our VAs to do their best work. Our guiding principle is that truly positive motivation is based on connecting our freelancers with clients they respect who are running businesses that interest them. Even our process for bringing together multiple VAs to work on a single project includes a consideration of how their personalities and work styles complement each other (and those of their client). I think as a female leader, I’m open to non-traditional approaches that value harmony and mutual trust, not anxiety-causing motivational tactics, as the ideal path to reach the best outcome for our clients.

Related: 3 Lessons for Leaders of Remote Teams: It All Starts with Trust

Keeping the Virtual Office Door Open

The stereotypical CEO is definitely not a “man of the people.” They make decisions, hand them off to their management team to implement, and know little, if anything, about their individual employees. They communicate mostly with shareholders and their big oak door is most definitely closed.

In contrast, values-based leadership depends on transparency. For this reason, it’s important to me that every VA and client knows that my virtual door is always open to them. Our commitment to transparency extends to sharing financial snapshots in our internal email newsletter, archiving emails in our CRM for the wider team to access, and giving our freelancers the opportunity to speak one-on-one with dedicated mentors through our new mentor program. In any company, some amount of conflict is inevitable, but good communication allows Trusty Oak to nip most potential issues in the bud before they can gain traction. 

Growing from Conflict

Responding to conflict is another area where values-based leadership truly sets itself apart. In a hierarchy-based company where morale is often already low, a conflict that involves management, team members, or clients can easily blow up into a crisis situation.

Hierarchy-based leaders often try to do damage control by sweeping the conflict under the rug. The focus is on eliminating the conflict as quickly and surreptitiously as possible – for example by firing or transferring a team member or cutting ties with a client before anyone notices that there was ever a problem. Unfortunately, people usually do notice when something goes wrong and it’s human nature to assume the worst when we only know part of the story.   

I think many female leaders of values-based companies are more likely to approach a conflict with a spirit of empathy and transparency. I believe in taking the time to hear both sides out. Conflict helps us grow when we aren’t afraid to face it, and one of my roles is to hold our VAs accountable and give them the space and support to rise to challenges, repair relationships, and gain new strength and wisdom.

Good leadership means leading by example. I hope that people see I take responsibility for my actions and try my best to embody our values-based culture. Trusty Oak has truly become a way for me to live out my life’s purpose of guiding other people through leading and learning. Along with many others, I am working to make values-based leadership based on authenticity and support for the individual the standard for remote teams everywhere.  

(Photo credit: Felicia Reed Photography)

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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.

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