with Amber Gray

Hiring, delegating, and leading team members are frequently discussed in my coaching sessions with business leaders. And last year, I grew my own team by partnering with Amber Gray, founder and CEO of Trusty Oak, an award-winning, Austin-based virtual assistant company. Trusty Oak was named the Freelancer Hiring Platform of the Year, and Amber was recognized as Austin’s Businesswoman of the Year in 2021, which is why I was so excited to talk with her on a recent episode of Elite Achievement. 

I remember being nervous about taking the leap to work with a virtual assistant and wondering, will I even have enough to delegate? If you’re wondering, I have more than enough to delegate. That thought ended up being fear and not a problem at all!

Before I jump into my conversation about best practices, advice for hiring, and more, Amber mentions the topic of delegation. It really is a skill set that isn’t highlighted or talked about enough. Amber agrees, explaining that it is the most important thing we can do in terms of professional development because if we can learn to delegate, we can scale our business. 

I ask Amber to share more about Trusty Oak, specifically who it is and what it does.

Trusty Oak: Connecting Entrepreneurs with Virtual Assistants

“Trusty Oak is a US-based virtual assistant company,” begins Amber. “Our goal is to serve entrepreneurs who need virtual assistants and focus on creating a great experience for our freelancers (our VAs). We’re hoping to facilitate a partnership while elevating that experience for people looking for support that don’t know where to start. That’s really our niche and focus right now is helping people who are first-time users of a VA who may be nervous about delegating. Fear is a big part of what holds us back in many things, but definitely delegation too. Our goal is to walk alongside our clients to help them learn how to use a VA and learn how to delegate. And then, on the other side of that, we have mentors for each of our VAs to help them in their journey as a freelancer. We keep everyone growing and scaling, so it all works really well together.”

I can attest to what Amber is saying because once I finally stopped thinking about hiring a VA and actually hit the send button on the request form, I was blown away by how quickly I could delegate work to my VA. I believe I have the best VA team out there; Sarah and Denise are rockstars. And they have been able to free up so much from me so I can better serve my clients. I can coach and do the work that I love and then still execute on many other ideas I have to market and grow my business. 

“Thank you for saying so,” says Amber. “We have 68 virtual assistants, so there are a lot of Sarah’s and Denise’s out there making the difference for people like you.”

I ask Amber to share more about her journey to becoming a business owner and if she always knew it was her path. She shares how her journey was interesting and began as a pharmacy technician for eleven years. She was doing things like cleaning IVs, none of which had to do with tech or admin. But she had a web designer friend who asked if Amber would help keep her organized. The offer was to project manage on a case-by-case basis for $300 a website. 

“So, I went and bought a couple of books from Half Price Books,” says Amber. “They were on how to project manage, and how to use WordPress. And that’s how it started and when I realized I love technology. I love project management. I like creating processes for things and helping other people who may not have that skill set to get things done more efficiently. In 2010, the startup that my friend was working for grew rapidly, and we were both hired on as employees. I eventually became the web director overseeing a remote team of developers, designers, and content people. After five years, I left as the VP of Operations. But I soaked up and learned a lot from my boss.”

Amber goes on to explain how at the time, she struggled to find a new job that she wanted and began thinking about something bigger. She came across a VA company in Georgia and loved the concept of virtual assistants. She applied directly to the company but was told she was overqualified.

“I just had that lightbulb moment of like, I could start a business that does this,” says Amber. “I could do it, and I could create jobs. And so, from the beginning, I didn’t want to stay a virtual assistant forever, but I was the first VA of Trusty Oak.” 

We talked earlier about how fear was a part of my journey of hiring a VA. Amber mentioned that fear is a part of many of our journeys, so I ask her if fear followed her idea of starting a company. And if so, how she overcame it.

Working through Fear by Asking for Help

“Yes, definitely,” Amber confirms. “As I said, I don’t even know how I ended up in the business world to begin with. And then to think, oh, I’m going to lead other people into this, that sounds scary. And honestly, that did hold me back. The way I overcame that was asking for help.”

Amber explains how she asked her boss from the company she was leaving if he wanted to be a business partner because she felt she couldn’t do it on her own. After about a year, she bought him out. From there, it was difficult. “It was all on my shoulders to make payroll and figure out how I’m going to take care of my own bills,” says Amber. “I was working extra jobs. I was driving for a company like Lyft and doing all the things just to make it all happen. And I wasn’t making what I wanted, even a few years after when I thought I would be. Now I’m taking home a decent salary I can be proud of, but it’s still not where I want to be. I think if I had realized I was more capable than I was in the beginning, I could have done it on my own from the start.”

We all feel fear as we strive to grow our businesses and achieve our goals. And I find that hearing stories like what Amber shared is helpful because it reminds me and others that we’re not alone. We can work through our fears and take action to build businesses and achieve our goals.

“Yes, absolutely,” says Amber. “That’s the whole reason why I share details about the partnership and the darker side of the story because we need to see, it’s not always what you see online. It’s not always the good stuff. We’re working hard behind the scenes. And yeah, I’ve been doing this now, coming up on seven years. And it takes longer than you think it does. I felt like I was struggling, not paying myself what I was worth for much longer than what I expected when I started out. But that’s just how it goes. And it’s okay. You just have to keep pushing forward and ask for help when you need it. That’s the biggest thing for me is finding people that can do things that I can’t do, which ties really well with delegation.”

Before we delegate, we have to hire, so I ask Amber what best practices for hiring she can share.

Hiring Best Practices (and Top Mistakes to Avoid)

“The number one thing is that you need to know what you need first,” Amber begins. “And that means that you are going to need to put in some time. If you’re looking at hiring a virtual assistant, especially for anyone busy or overwhelmed, you’ve got to carve out time to be able to say, okay, this is what I need. Because if you go into it without having that plan, you might not hire the right person. The other thing is that we use different ways to weed out and reduce the amount of time you spend on the screening process by asking people to send a video with their application. So, they submit a resume, cover letter, and fill out our application on the website. But the very first step is, hey, you’re more than just what it says on your resume. We want to hear from you. We want to know why you want to work for Trusty Oak and about your skill sets. We give them a free tool to record that introduction, and if they don’t do that, then we don’t even look at their resume because we get a high number of applications. We needed a way to gauge if they will follow instructions and are excited about Trusty Oak and if they are confident in their abilities because that’s a big part of success for a VA. The other tip is to hire for fit over skills. What I mean by that is you need to know your own values and expectations of the way you communicate your work and then hire somebody that will align with those values. Our interview process also includes questions about values. We have five core values, and we go through each of them and ask what they think it means. We have a very strenuous process. We only hire about 4.4% of applicants because many people want to work in remote, flexible jobs. And we want the best of the best. But aligning for values is the main thing. Skills can be learned, especially if you’re resourceful.”

I heard three clear recommendations – number one, know what you need. Number two, develop a process. And then number three, hire for fit over skills. It’s all very practical advice for any business owner, entrepreneur, or leader. I ask Amber what mistakes she has seen in hiring, and she says rushing the process. The Trusty Oak process and vetting take about three weeks, and it’s intentionally not rushed so that there is time to get to know each candidate. She explains that they talk on the phone, on video, and they have assessments that gauge written communication skills, problem-solving, and more. 

“That’s another tip I would say is whatever you are doing in your vetting process, do things that are going to give you answers to multiple questions,” says Amber. “Like for our assessment, written communication is one part of it, but it’s also how they are answering the questions. What are their problem-solving skills? We’re vetting multiple things in different steps. We want to know if they have a professional background. Or if they are happy. Do they seem like somebody that would be fun to work with? There are different aspects you’re looking for. And having multiple touch points gives you a chance to explore more areas about that person.”

Perhaps I should have asked this question before we even started talking about how to hire, but I’m curious and ask Amber when a business owner knows it’s time to hire.

How to Know When It’s Time to Hire: It’s All in the Numbers

“I’m one of those people that makes decisions from my gut a lot,” Amber responds. “But over time, I realized that knowing my numbers is the key to really understanding when it’s time because it’s not just about when I need help. It’s also when can I afford help? We’ve started tracking a lot of data, the financial data, and how many hours each virtual assistant is working. How many hours does each client need? How many hours can my client success coordinators handle? Or how many clients can they support? There are many different elements to tracking numbers. And as we go, we keep adding more data points that we want to keep track of. Data has been an essential part of our decision-making, especially over the last year, because I got a finance guy on the team that started helping me understand the numbers more. That has been a game changer to start keeping track of the numbers and seeing where we came from. What was it like last January? What is it like today? Being able to have that context is helpful. So, I would say the only way to know is to start tracking the numbers and have data to say, okay, we can tell by these numbers. It’s time to add someone.”

I am a huge fan of tracking because it is a massive part of the goal achievement process. I started tracking towards the end of last year what percentage of my time was spent with clients and what percent was spent on other activities. Knowing that number helped me to say it’s time to add more help onto my own team, so I can spend more time with my clients doing the work that I love. So, if we know our numbers, feel ready to hire, and have the best practices in place, I ask Amber how do we delegate? She replies by saying while it may not be popular, the answer is self-discipline. As she’s observed hundreds of clients, she has noticed that the more self-disciplined they are, the more they get out of working with a VA. Another tip she has is to take the time to plan your week. 

“If I spend 30 minutes to an hour, every week, planning my week, I uncover things that I need to delegate,” says Amber. “If I don’t take that time, things are flying at me during the day. And I think, oh, I need to get some help with this. But last-minute help sometimes doesn’t turn out the way we expect. People aren’t available. And virtual assistants, in particular, are working flexible schedules. They may not be able to drop everything and take care of you. So, you’ve got to plan ahead to get the most out of it. Secondly, start with small, repeatable tasks. If it’s something that happens daily, weekly, monthly, even quarterly, that is likely something that’s going to be great to delegate because even if it only takes minutes, it adds up over time. It might take you longer to teach them than it does to do it. But if it’s repeatable, it’s going to save you a lot of time in the long run. So those are two ways to get started, plan your week and start with small, repeatable tasks.”

I agree with Amber 100%. And I am a work in progress on delegation. But one of the things I do at the end of every week is the Friday ritual, where I write down my wins for the week, lessons learned, and priorities. And I start looking at my calendar for what I have going on and what’s on the to-do list. As I do, I’m thinking that might be something I can ask Sarah to help me with, or that might be something Denise can handle. Going through that process helps me show up to my one on ones with my team members with additional work, and it has helped us accomplish a ton in a short amount of time.

“You just mentioned another tip; have a one-to-one with the person you’re delegating to,” Amber adds. “If you can have a regular meeting with your virtual assistant, you’re going to get more out of working with them because they’re going to have an opportunity to ask you questions that prompt you to delegate other things.”

As Amber and I continue to talk, I ask her what she sees as the difference between leading and managing and if she has a recommendation for individuals as they work with their teams.

Manage Your Processes, Lead Your People

“Yes,” Amber confirms. “I say manage your processes and lead your people. With the people, you want to be able to cast the vision for where you’re going, why you’re doing what you’re doing. If they understand your why and what you know, not just how to do something, they’re able to eventually make decisions on your behalf because they understand the why. So, whenever a curveball comes their way that they don’t have a written process for how to do it, they know how to make that decision. It is important for you to view the relationship with anyone you’re delegating to as a partnership. And if you can approach it with that attitude of collaboration, open communication, that’s important to the long-term success of working with your VA. They need to understand your why and start getting the big picture of things so that they can help you even more.”

I remember when I was early in my career, I had a lot of projects delegated to me. I always felt more inspired if I understood the bigger picture of how this one report would help us achieve this big goal. It made me feel better about the task at hand. I think that it’s really important to explain some of the why behind what we’re asking our team to do. Amber mentioned earlier that she really started developing project management processes. I know process comes up a lot in my initial coaching conversations with potential clients, and I hear all the time that people want to streamline processes or be more efficient. I ask Amber what advice she has for those who want to improve processes.

How to Improve Your Processes and Timelines

“When you start thinking about documenting processes and writing out how to do every little function of your business it sounds daunting,” says Amber. “So I go back to the free tool that I mentioned we share with VAs to record, Loom. If you’re using Loom, you can screen record and narrate. This is an easy way to start developing processes, because you’re already doing the process you need to develop. It just may not be documented or polished. So, record yourself doing the thing and narrate and then send that to the person you’re delegating to. One, you’re going to train them through that process. But also, then they can create a process for you and make something polished or ask questions about it. If you have a problem with someone you’re working with, it’s often because of the process or communication. So, if you have documentation on how to do things, and something didn’t go as expected, you can go back and look at the process. Is the process right and this person didn’t follow the process, or is the process broken, and we need to add a step or take out a step? You can tackle documenting even in a rough format and then get someone else to help you polish it and refine it.”

That is so helpful because sometimes when we think about processes, it feels daunting, like it’s going to be this massive task. And it can be really simple. You start by rough drafting a process. I always recommend to my clients that we pick one process to focus on. We don’t have to do the whole business at one time. But let’s pick one that will help drive your goal and start documenting there.

“Definitely,” Amber agrees. “We just recently focused on our client success process. I mean by client success; we have special team members that check in with our clients to make sure things are going well with the virtual assistant. They’re there to help them if they’re struggling with delegation. It’s the support person to ensure our clients are getting the most out of the experience with their VA. I was doing a lot of that in the beginning, and I started slowly writing out how I was doing it. And then I was able to bring someone else on to do it. We spent a good part of last year refining that client success process. And once we did, we saw better retention with our clients, and better utilization with our client hours. Everything started getting better just by simply focusing on building that process. It took us a good six months to iron it all out. Before that, we went through our whole process with hiring. It can be daunting, so tackle one at a time. I totally agree with that approach.”

I’m curious what motivated Amber to go through the documentation steps with all of her processes, and she shares it was the desire to get the tasks off of her plate. She explains how she knew the only way to start scaling was to delegate, which can start with documentation. As long as she was stuck in the day-to-day operations, she couldn’t do more that was in line with her bigger vision. 

Scaling can be a hot topic for entrepreneurs, so I ask Amber how she defines it.

Scaling Your Business

“In my mind, scaling means growing in an intentional way,” says Amber. “I want to build systems so that I can see how it affects the future. Because just like we were talking about knowing when to hire, that requires knowing the numbers. So, I have to have a process for collecting those numbers and bringing them together in a meaningful way. All of these different pieces contribute to the greater goal. The one big goal is to impact the lives of 500 virtual assistants with sustainable jobs. And then obviously, we have a big goal to support our clients as well. And we want entrepreneurs to flourish and thrive and not experience burnout. So, this is a win-win on all sides. But it requires thinking about the big picture and breaking it down into smaller pieces that we can tackle. Scaling is almost like breaking it down before building it back up because you need those smaller pieces so you can get focused and drive forward on one thing at a time, or multiple things if you’re delegating.”

I ask Amber about something we were talking about unofficially, doubling her revenue. She confirms that they more than doubled the revenue from 2020 to 2021, and in 2020, they experienced 88% growth. 

“It’s been kind of shocking in some ways,” Amber shares. “I mean, I know it’s what I wanted to do, and I’m taking my own medicine and doing all the things to help myself grow, but it’s been a wild ride and very exciting! We doubled our team size too because we had around 30 virtual assistants, and now we have 68 virtual assistants. So, it’s been doubling revenue and doubling the team. But all in all, it’s doubling our capacity is what my coach has been telling me because it’s like, yes, you doubled your revenue because you doubled your capacity and what you’re capable of doing. That’s been really exciting to understand that some of what we’re doing by developing processes and getting focused is giving us the ability to be more efficient and impact more. So, it’s motivating and exciting and a little bit contagious around the treehouse, as we say, which is what we call our virtual office.”

I hope as everyone reads this, they think about the need to slow down and document some processes, add weekly planning time, get clear on the activities that generate revenue, and things that can be delegated. What Amber has shared is inspiring! 

“Thank you,” says Amber. “It’s been inspiring for me to see the team and the contribution that everyone has because once you show them a path for how we get there, they’ll jump in. They’re the ones taking the ball and running it forward because they can see where we’re going. Another thing I’ve spent a lot of time on recently, and what I’ve learned working with my coach, is figuring out my role. I had no idea how powerful it would be just to define where we’re going. So, I drew an org chart that showed where we are right now. But here’s what I’m envisioning for 2024. And when I showed that to the team, it’s almost like it was an epiphany that everyone had like, oh, okay, that’s where we’re going, well, then this is what I need to be doing. And everyone’s sort of locked in their lanes and understood, okay, this is what I need to do. They see the potential for the future. And it had a huge impact, just showing people what the plan is. It has been very powerful. So, you’ve got to free up your time to focus on future planning, strategizing, showing people the vision because it is key to that long-term success.”

It sounds like Amber became extremely clear. And that level of clarity often helps you achieve breakout performances. Amber confirms that clarity was a theme for one of their quarterly planning days. “I hired someone to handhold me through establishing the Rockefeller habits, and that’s where everything changed,” Amber explains. “For me, I was struggling to get clarity. And once I realized, okay, this is how I approach focusing on priorities, this is what I need to be doing, this is what my team needs to be thinking about instead of going all over the place with all the big ideas we still have. We now say okay, this quarter, we’re driving forward on these initiatives. And our next planning day is here, and that’s when we’ll reset, and we’ll plan again. We do this in quarterly sprints, but it’s all about staying focused and only biting off what you can chew.”

As I wrap up my conversation with Amber, I thank her for all of the nuggets and insights she has shared, like overcoming fear, hiring best practices, delegating, and more. I ask her where others can go to learn more about Trusty Oak, and she recommends visiting www.trustyoak.com or connecting with her directly on LinkedIn.

And with that goal achievers, keep celebrating your weekly wins, making note of the lessons you’ve learned, and identifying your priorities for next week.

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