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Kelly Roach: “Keeping your team connected”

I would love to see more entrepreneurs leveraging their earnings to give back. Last year I moved my coaching company to a 1:1 giving model. For every new client we add to one of our coaching programs, we donate to the foundation I started, that has three core focuses for philanthropy. I believe that if […]

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I would love to see more entrepreneurs leveraging their earnings to give back. Last year I moved my coaching company to a 1:1 giving model. For every new client we add to one of our coaching programs, we donate to the foundation I started, that has three core focuses for philanthropy. I believe that if people are equipped to find financial freedom for themselves, that they can leverage that freedom to make a huge impact on the world. So, as I coach entrepreneurs, my hope is that more of them will adopt this model and leave a legacy that goes far beyond making lots of money.


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Kelly Roach.

Business strategist Kelly Roach transforms overworked entrepreneurs into seven-figure CEOs, by teaching them how to leverage timeless business principles, employed by billion-dollar corporations, with the speed and agility of the most powerful online marketing strategies of today. Prior to starting her own company, Kelly spent years in corporate America, rising through the ranks of a Fortune 500 to become the youngest VP in the company. Kelly is not only a best-selling author but is also an ongoing television business expert.


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”?

Growing up just above the poverty line, in a family of 5, I decided early on that things would be different for me and my children. I worked hard growing up, scrubbing toilets to pay for dance lessons, and working multiple jobs in college. After graduation, I got an entry level job in sales, for a Fortune 500 company. In eight years, I was promoted seven times to become the youngest VP in the company. I led my team through the recession of 08’-10’, without letting a single person go. In fact, we had record breaking sales that year. As I was climbing the corporate ladder, I realized that I was making millions of dollars, working 60+ hours a week, for OTHER people. When I thought about what I wanted in terms of lifestyle, that was not it. So, I started my business on the side, while continuing to work my corporate job, and built that company for two years before quitting. I relied on lots of hard work, my sales skills, and an unstoppable mindset to help me build what is now a multimillion-dollar business coaching company with over 500 clients, across the globe.

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

So, this technically happened just before I started my career, but was a defining moment for me. At the time, I was a Philadelphia Eagles Cheerleader, and the year I joined, instead of doing their traditional swimsuit calendar, they decided to do a lingerie shoot instead. I knew that I wanted to build a career in business and that this shoot could do long-term damage to my career, so opted-out. The consequence? Missing out on an incredible trip to a tropical location, and all kinds of media and opportunities that came from the shoot (for the other girls). While I did not know exactly what my future career would look like, I knew that this was not a smart long-term play for me. That decision shaped how I made decisions for the rest of my career. I was able to handle the consequences and am now so thankful I made that choice, way back when!

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?

I am not sure I would call this funny, but it was a true learning experience, for sure!

When you are just getting started in your business, you have this blind optimism and excitement, and you want things to happen overnight. I was still working full-time as a Fortune 500 executive when I started my business. I put so much work into my first big webinar and was so convinced it would go well that I took the next two business days off of work to do all of the consultations and registrations for everyone that I was sure was going to be registering as a result of my webinar. By that time, I had honed my sales skills and was ready to close some deals after the webinar wrapped.

Unfortunately, I did not have the audience or authority built up to where it needed to be at that point. So webinars probably weren’t the best format for me. I got absolutely zero sales from it, despite my extensive experience and success in sales. Clearly did not need those two days off.

The takeaway for me? You can work extremely hard on something and not see results. I put in hours and hours of practicing and running through the webinar — but my confidence and authority and credibility just were not there yet. Those things take time. You have got to be willing to play the long game and not see results right away.

Building a freedom-based multimillion-dollar company has taken us years. But we did it.

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

Last year I started giving each of my employees a mental health day each month. This is a paid day off that allows them to totally unplug and take some much-needed time off. It’s been huge for my team, as it gives them the space, they need to come back with more energy and focus. If possible, I would consider offering something similar.

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?

Sure, I started my business a little over seven-years ago. We have been remote the entire time. I wanted the freedom to work from home, and wanted my employees to have that same freedom.

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?

The five main challenges would be:

  • Keeping your team productive — when your team is working virtually, you have very few checks and balances to ensure they are using their time wisely. They could be watching tv all day long if you do not have the right systems in place.
  • Keeping your team connected — without co-workers in the office to eat lunch with or have a water-cooler conversation with, your team is likely to feel a bit lonely at times.
  • Holding your team accountable — phone conversations and video conference calls don’t pack the same punch as an in-person conversation when it comes to accountability.
  • Maintaining motivation-when working virtually there is not a lot of external motivation. Your team needs to be incredibly self-motivated.
  • Maintaining boundaries between work and home life -when you work from home the boundaries lines between home and work can get blurred quickly.

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

Have multiple check-ins each day. Each department in my company has a morning meeting and an EOD meeting on a video call. Each team member has a set of metrics that they are accountable for, and metrics are tied to bonuses and commissions, so the team stays motivated. We have blackout hours where the team is focused on their most important activities (no internal meetings allowed) and our mental health days allow for some boundaries between work and home as they are required!

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?

Yes! We do 1:1s on video calls so that we can still see one another. It is not quite the same as being in person, but it’s the next best thing.

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

Unless something is a formal warning, we try to keep feedback to conversations when possible. However, if I do address things in an email, I usually just keep things short and to the point. I let the person know that I am open to conversation, and remove any vague language, then state the expectation clearly. I spend a lot of time building relationships with my direct reports and ask them to do the same, so a piece of constructive criticism usually has context, and feels less harsh.

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?

Just keep the lines of communication open, the standards the same as usual, and the focus on outcomes. Meet regularly, set team goals, celebrate wins, and get comfortable with a group text thread!

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?

We do quarterly team meetings in person (outside of a pandemic) where each team member shares their personal goals and how the job, they are doing at the company can help them accomplish those personal goals. We recast the vision, innovate, and set up what is coming next. These meetings help bond the team together and are incredibly helpful in keeping people motivated and bought in!

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. 🙂

I would love to see more entrepreneurs leveraging their earnings to give back. Last year I moved my coaching company to a 1:1 giving model. For every new client we add to one of our coaching programs, we donate to the foundation I started, that has three core focuses for philanthropy. I believe that if people are equipped to find financial freedom for themselves, that they can leverage that freedom to make a huge impact on the world. So, as I coach entrepreneurs, my hope is that more of them will adopt this model and leave a legacy that goes far beyond making lots of money.

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

“Be the best that you can be in everything that you do.” It is a quote I have lived by my whole life, and it has served me very, very well. It has helped me, and it has allowed me to help many, many other people. It sounds simple, but if you wake up every day and live this quote out, you become unstoppable!

Thank you for these great insights!

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