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Daniel Ramsey of MyOutDesk: “Finding the right talent”

Finding the right talent. To build out your ‘Virtual Dream Team’, do not make the mistake in prioritizing a candidate’s skills & experience over their culture fit & talent. There are two things you cannot teach people and that’s culture fit and innate talent. So when recruiting, follow this order for criteria: culture fit, talent, […]

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Finding the right talent. To build out your ‘Virtual Dream Team’, do not make the mistake in prioritizing a candidate’s skills & experience over their culture fit & talent. There are two things you cannot teach people and that’s culture fit and innate talent. So when recruiting, follow this order for criteria: culture fit, talent, skills, and lastly, experience. Now, what is culture fit when you are hiring? It is the type of candidate who would match well with your organization’s culture. They are the person who’ve always wanted because you know they can lead your company to newer opportunities — such as the person who has ever received this sort of response from you: “We’re not ready to hire yet, but as soon as we do, we want you.”


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Daniel Ramsey. Daniel is the founder & CEO of MyOutDesk, the highest-rated Virtual Assistant company in the marketplace with over 500 hundred 5-star reviews, and over 13 years of experience serving more than 6,000 clients.

Daniel founded MyOutDesk during the last global financial crisis of 2008 to help businesses leverage the remote workplace and scale businesses with virtual assistants. In 13 years with MyOutDesk, Daniel has helped over 6,000 clients scale their businesses and grow profitability. He’s had the opportunity to work many of the largest sales organizations, technology startups, insurance, real estate, and healthcare companies, and he’s willing share those lessons with you.


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

I had a natural love for business — I was a child serial entrepreneur selling candy bars around town. My experience learning the principles of business evolved over time into a lawn care business and a paper route. As I got older, I got restless. The harder I tried to find a path to financial freedom, the more dissatisfied I grew with my surroundings.

I launched a real estate company shortly after college. It was my first experience of a multimillion-dollar business, and it led me to innovate the 7-Figure Business Roadmap, which is now MyOutDesk’s unique, step-by-step process to build a 7-figure business. All the financial and global impact I’ve had can be traced to an inner hunger to be more financially successful than my parents, and to make a difference in the world. To simply matter.

After several years working in the real estate industry, I realized that most business leaders & entrepreneurs spend too much time doing tasks that are necessary but highly administrative, routine, and time consuming. Working overtime seemed necessary in order to finish all these tasks and keep in touch with clients and generate new business. While recovering from the global financial crisis, my brother introduced me (virtually) to Lily, who had been doing some work for him from the Philippines

And that’s how I founded MyOutDesk, in 2008, with a vision to provide businesses with indispensable leverage through our virtual assistants to aid professionals in regaining time and freedom, have the ability to grow their business, all while reducing costs.

Can you share the most interesting story that happened to you since you started your career?

It took two years to build my three companies to a point where I felt comfortable leaving them for a time and having them run without me. In 2011, I did just that. My wife and I moved to Peru for 6 months, and while we were there, the business continued to grow and make money for me from a distance. We rented an apartment there, got involved in our community, joined a gym, and learned Spanish for 4 hours a day. Have you ever wanted to immerse yourself in another culture, to live like the locals? We were able to travel to 5 different countries while experiencing everything South America has to offer, from the Inca Trail, to the vineyards of Mendoza in Argentina, to surfing in North Chile, while generating lots of cash.

We lived, earned money, and grew our net worth, all while using the remote work systems. For the first time in my career, I had leapfrogged my peers, who were back home stuck in the daily grind.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Mistakes…I define ‘mistakes’ under the category of experiences that are painful in the heart or in the wallet. So, I’ve made all kinds of funny mistakes! I guess a general pattern is that I’m not the guy that remembers every detail.

Once on my way to the movies with my wife, Whitney, I was on a call with a client, helping them with setting up a ‘blended business model’ (remote + physical teams). I was so focused on my client that, it was 20 minutes into the movie that I realized, “Wait a minute. I’ve already seen this movie.”

I’m so hyper-focused on my clients and on helping businesses to scale that I tend to miss minute details, such as even forgetting to eat lunch. I’ve learned, ultimately, to intentionally be present especially when making decisions.

What advice would you give to other CEOs or founders to help their employees to thrive and avoid burnout?

Every professional can suffer from burnout during their career. Hiring a full-time virtual professional, at up to 70% less than the cost of a traditional employee, to assist in managing elements of your workload (and your team) can help relieve the stress that a hectic work schedule can cause.

To thrive, a considerable part of our businesses can be leveraged and assigned to other talented people. We can prepare ourselves for delegating roles by building systems and processes in place. Look at what you are currently doing, understand most important work that moves the needle, and document everything. This is key because it helps us lay out what we need to do next and what kind of talent to hire to balance needs.

Having someone there to help organize your schedule and deal with tasks frees up your work schedule to focus on more productive aspects of your business and also helps to avoid your work leaking into your personal life. A virtual professional can help you maintain a work-life balance that is crucial to optimizing your productivity and general well-being.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

Back in 2007, I hired my first virtual assistant in the real estate space, and nobody else then even heard of a virtual assistant. My virtual assistant company’s origin story is set during the Global Financial Crisis of 2008. MyOutDesk was founded during this last major recession and has since been successful in helping other businesses scale with virtual assistants. So, it has been over 13 years of experience since I first managed a remote team.

In fact, Tim Ferriss’ bestselling book, “4-Hour Workweek,” wasn’t even out when I first started setting up my business. Ferris’ book explains the core value of leveraging remote teams & virtual assistants in business. When the book finally came out, MyOutDesk exploded because nobody else was providing quality virtual assistant services at a high level like we were.

We are one of the pioneers who built the virtual assistant industry, and it’s been a lot of fun to make mistakes and then fix it, and then repeat that cycle all over again. For us, it’s important to keep shifting and growing in order to provide the best remote work knowledge & value out there.

Our first client in 2008 went from five to seventeen VAs with a completely revamped organizational model in short order, and he told me, “your virtual professionals shaved 250,000 dollars off our monthly overhead.”

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

It’s incredible how today’s digital age allows teams to work together in ways that were once unimaginable. Even with all the great tools & software out there, it takes leadership to foster a thriving remote team. Whether you will directly manage your virtual team or plan to train a team leader, this is what you need to know…

1) Finding the right talent

To build out your ‘Virtual Dream Team’, do not make the mistake in prioritizing a candidate’s skills & experience over their culture fit & talent. There are two things you cannot teach people and that’s culture fit and innate talent. So when recruiting, follow this order for criteria: culture fit, talent, skills, and lastly, experience.

Now, what is culture fit when you are hiring? It is the type of candidate who would match well with your organization’s culture. They are the person who’ve always wanted because you know they can lead your company to newer opportunities — such as the person who has ever received this sort of response from you: “We’re not ready to hire yet, but as soon as we do, we want you.”

2) Communication, communication, communication

I cannot stress this enough: good communication with your team is essential. To conduct and lead virtual meetings, first off, you have the appropriate platform to conduct your meetings. You want something that allows you to have group calls, video capability, chat, and document sharing. Ring Central or Zoom are some examples of enterprise systems that you could use.

Next, always set a daily meeting or a morning huddle. There are only a few times you can interact with your entire team, compared to impromptu interactions in a physical space. Regular huddles are short 10–15 minute calls where your team can give you a quick rundown of what they have going for the day and allow space to ask or answer any questions. You can set longer weekly meetings where you can discuss things in depth. Make sure that you use some of your time during meetings to get to know your team.

Outside from business as usual, find ways to build relationships with your team and let them know that you care about them personally as well as professionally.

3) Developing & enacting action plans

You have goals for your business, right? Well setting them can be easy but what matters most is that you develop action plans to meet them. Develop agendas and action plans for your team members so you all have a clear path towards hitting your marks. Make them specific, yet not too rigid. Striking the perfect balance will set you and your team up for sustainable success without burnout or other repercussions.

4) Setting expectations

Set clear expectations for your team is essential to achieving your goals. I love using quality metrics, such as key performance indicators (KPIs), weekly & monthly team scoreboards, and the SMART goals framework — they’re overall practical and measurable. All goals should be SMART (Specific, Measurable, Attainable, Relevant, Time Bound).

We love to track our productivity using project management systems and MyTimeIn, our all-in-one Remote Team Productivity Tracker. MyTimeIn is our in-house scheduling software that ensures your virtual assistants & remote workers are on-time and productive.

5) Fostering accountability

Leading a virtual team is not too different from leading any other team. It takes a strong leader not just a ‘boss’ — as John C. Maxwell once shared, “A leader is one who knows the way, goes the way, and shows the way.”

Remote work productivity relies on strong individual autonomy to complete one’s work. Make sure that each member knows their respective responsibilities and that you fully understand them as well. Give them ownership of their role and reward them for a job well done. If they hit any roadblocks, give them the time and attention they need to help them surpass the obstacles. It’s a team effort to foster individual and team accountability. The goal is that each of your team members treats your business as their own and that they understand that when they win, you all win.

Based on your experience, what can one do to address or redress each of those challenges?

I highly recommend that businesses craft a ‘virtual playbook’ for all remote teams. It’s a worthwhile time investment to create one of these as it benefits your business. What is a ‘virtual playbook’ exactly? It’s a step-by-step, documentation that outlines each of your processes and what to do when things go awry.

Avoid repetitive mistakes and avoid making unpleasant and counterproductive assumptions, like, “they should have known that” or “I’ve already taught you how to do that” — try the ‘Play, Pause, Do’ method. I’ve integrated this simple method into our remote culture.

‘Play, Pause, Do’ requires that every standard operating procedure in your “playbook” has a video associated with the written documentation for an employee to simply refer back to. The method allows an employee to go back to the documented procedures and be able to complete tasks as expected.

It’s a playful message. I even use ‘Play, Pause, Do’ to identify time to play, to pause for a moment, or to do sprints across various project cycles.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

Visual communication is important in both physical and remote settings, but visual cues are communicated differently between the two settings.

To address any issue constructively, I like to let the team scoreboard do the talking. This is essentially a rubric to score for quality outcomes. The scoreboard is not a serious report card, but rather a discussion point. This gives a quality metric for each individual and the overall team to reflect on results and productivity. We identify any internal and external factors affecting both the good results and the lack of results, and then create a short-term game plan to address & resolve any issues.

This is where I like to ask the employee to refer to the ‘virtual playbook’ to fix any issues. If a new process has yet to be documented, I allow freedom for the team to agree on how to best document the new procedure.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

My first reaction is — do not address constructive feedback entirely over email. Email is tone deaf so even feedback that is well-intentioned will sound bad. The right approach is to meet face-to-face (yes, you can still meet face-to-face virtually).

Your message will create the greatest change and impact by visual communication. The human brain can retain visual communication easier than just text — 95% of messages are retained by using visuals, while only 10% is retained using text.

Email can be done after a face-to-face meeting and positive praise needs to balance out any constructive feedback. As a leader, maintaining team morale is more important than giving constructive criticism.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

Of course. I’d love to share and be of help especially in these times. As a matter of fact, MyOutDesk has a free, 3-step Fast Guide to Working Remotely During a Health Crisis with checklists & additional resources.

Remember that change takes time. Allow an adjustment period for your team and repeat key messages regarding any changes intentionally and consistently. By doing so, you will get everyone on the same page.

Some other practical tips are:

  • Suspend nonessential employee travel.
  • Offer special training on a company remote work culture.
  • Urge employees to stay home when they are sick and maximize flexibility in sick leave benefits.
  • Do not require a doctor’s note for sick employees (healthcare offices may be very busy and unable to provide that documentation right away).

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

When working with a remote team, one of the most important things you can do is set up your company culture to resonate well to a remote setting. Apart from understanding that children & pets are now the new officemates, we have a handy 20-point article that describes how to optimally foster a remote culture.

Also, our Organizational Change Model is a great framework to bring change into effect and to breathe life into any organizational culture change or procedural change, like transitioning to remote work.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Thank you. I’m living that dream right now, and the dream is still growing! As I’m a big believer in the core values of MyOutDesk — “Family Table, Healthy Soil, and Servant Heart.” — I created a charity called the MOD Movement, where employees are empowered to carry our company values beyond the office so that they can make the furthest impact as possible.

Since 2013, MOD Movement is a give-back program where employees (remote or in office) can participate in a cause based on their own interests and preferences. Individuals can get involved by contributing money or their time. In practice, charity work helps boost employee morale and retention. It’s best to encourage employees

to identify a cause of their preference.

It’s been a blessing to see the movement grow. We served an orphanage since 2013, a senior home, a youth program, and now focusing our efforts on families affected by hardships in these times.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite quote is by Zig Ziglar, “You don’t have to be great to start … but you have to start to be great.” If you have an idea, just do it! Everything I have been able to say that I’ve accomplished has come from a mere idea. It’s okay if you can’t take a large step because even a little momentum has the power to breathe your idea into life and to carry it through. Most people never start.

Thank you for these great insights!

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