Kerry Wekelo of Actualize Consulting: Five Things You Need To Know To Successfully Manage a Remote Team

Fotis Georgiadis
Authority Magazine
Published in
9 min readDec 13, 2020


Understanding each person’s communication style: Not everyone likes to communicate the same way. For example, some people like to use instant message for small items and email for bigger tasks. Others prefer to talk through each task. It can depend on the person, but becoming familiar with these styles can make sure everything runs smoothly.

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

KERRY WEKELO, MBA, is the Chief Operating Officer at Actualize Consulting, a financial services firm. Her book and program, Culture Infusion: 9 Principles for Creating and Maintaining a Thriving Organizational Culture and latest book Gratitude Infusion, are the impetus behind Actualize Consulting being named Top Company Culture by Entrepreneur Magazine, a Top Workplace by The Washington Post, and Great Place to Work-Certified. In her leadership, Kerry blends her experiences as a consultant, executive coach, award-winning author, mindfulness expert, and entrepreneur. Kerry has been featured on ABC, NBC, NPR, The New York Times, Thrive Global, SHRM, Inc., and Forbes.

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 grew up in a small town in Virginia and studied marketing and finance at Virginia Tech. When I graduated, I got into consulting because it was a way to use my people skills and knack for problem solving. In 2005, my brother asked if I could help him build out the internal operations of the company he started, Actualize Consulting. Actualize has been remote in some capacity since its inception and gave me a lot of experience leading remote teams. As a firm, we were lucky to feel prepared for the switch to fully remote work in the pandemic. We didn’t face any of the growing pains that typically follow a change of that caliber.

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

It’s funny how things in life come full circle — from starting Actualize as a remote company, to having a physical office, and now becoming entirely remote because of the pandemic. Even though we are spread apart, our team is as close as ever and it’s been rewarding to see how our leadership styles have changed throughout the years… and seeing the improvement in creating a workplace that supports its employees. We have built upon a strong foundation and are now reaping the rewards.

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?

Back when I was working for a government consulting firm, one of our clients was the Army. We were doing vendor demonstrations in a hotel, but there was a sales meeting next door to our meeting room where they were trying to hype up the crowd. The sales meeting was so loud, we couldn’t hear our own demonstrations. One of the higher up officers in the army told me that I needed to get the other room to quiet down. At first, I went to the front desk and asked if they were able to control the crowd next door. I went back to the demonstrations, but the crowd was just as loud as it was before. The next time the officer told me to get them to be quiet, I told the manager about the issue — but it still didn’t get fixed. Next thing I know, the officer gets in my face and yells at me, telling me to get them to calm down — “NOW!” At that point, I walk into the room next door and pretend to be an audience member. I raised my hand as if I had a question, and I, in the midst of this huge crowd, tell them we cannot hear our meeting next door. Everyone in the room laughed at me, but they did quiet down. When I came back to the demonstration room, the officer called me the nickname “Killer” for the rest of the day because of the way I pacified that crowd. I gained his respect — it’s a funny story to think about to this day. I also learned how resilient I am… even though this situation was terrifying for someone starting out their career, I did stand up and do what I was asked.

What advice would you give to other business leaders to help their employees to thrive and avoid burnout?

The most important thing you can do to thrive and avoid burnout is take time for yourself. When we are so focused on others’ needs to the point that we forget our own, we will not be able to show up as our best selves. No matter how busy you are, take even just 5 minutes to do something you enjoy that isn’t tied to any of your responsibilities. Being a workaholic isn’t sustainable for most people; we only have so much energy to give and when that is out of balance, our home life will suffer. The key is maintaining a balance with a focus on personal wellness.

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?

15 years — so lucky to have had all the experience from the start of my employment at Actualize Consulting in 2005.

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?

  1. Understanding each person’s communication style: Not everyone likes to communicate the same way. For example, some people like to use instant message for small items and email for bigger tasks. Others prefer to talk through each task. It can depend on the person, but becoming familiar with these styles can make sure everything runs smoothly.
  2. Keeping the Team Connected: Team connections build naturally in an in-person environment when you are around everyone for the entire 40-hour work week. When we are separated by distance and computer screens, you need to actively put energy towards getting to know everyone and establishing a bond.
  3. Managing Projects: In the office, you can easily collaborate in conference rooms and by making rounds around the building. In a virtual setting, you are only as collaborative as the tools you have will allow.
  4. Maintaining Communication: When you aren’t working face-to-face, body language is missing from your interactions. Not to mention, small talk doesn’t really exist — so a lot of the little verbal updates you would give your team do not happen organically.
  5. Lack of Visibility: You don’t know what your team is doing at all hours of the day. It can be hard to reach them sometimes.

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

  1. Learning each person’s communication style can either be done through trial and error, or, to save time, by simply asking them how they prefer to communicate. For example, I tell my team that I prefer IM for small things and if they need to speak with me, I ask that they message me first to see if I am available before I receive a call.
  2. Keeping the team connected despite geographical differences and a virtual workplace requires some creativity. We regularly have “all hands calls” or firm-wide meetings that allow everyone in the company to hear updates and ask questions, partner check-in calls where small cross-sections of teams are in a video call with the firm’s partners, and we virtual team-building events like Zoom cooking classes and workouts.
  3. Managing projects virtually requires the right tools. For example, having a video call software like Google Meet or GoToMeeting helps with collaboration, ProjectPlace helps define and oversee tasks being completed, and Dropbox enables a way to collaborate on files and store them in a place everyone can access.
  4. To maintain ample communication, it is necessary to over-communicate. Sometimes it may seem over the top, but keeping on the same page is harder without organic conversation that happens naturally in in-person settings.
  5. To combat a lack of visibility, ensure everyone is on the same page about their schedules. I personally don’t mind if a team member needs to step out for an hour during the day, but I do ask that they put a note on their calendar that they can’t be reached at that time. This way, I don’t have to waste time trying to track them down. It goes back to the importance of staying in the loop and making sure everyone is communicating effectively.

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?

First, it is necessary to document any feedback you’d like to give. For example, you can send an email that you’d like to talk about X on your next call or even put it as a note in their performance review. Then, try to give it over the phone or in a video call instead of over email. Be clear, be concise, and keep your emotions out of it. Focus on moving forward in a positive way, and use this challenge to strengthen your relationship with the recipient of the feedback. I always like to say, “my goal is to help you be successful…”, because we are all on the same team and should want the best for each other.

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

Personally, I don’t think constructive feedback should be given over email. The lack of body language and vocal tone can fog the reader’s own interpretation of the message. Try to give any feedback over the phone, and if that is not possible, keep the focus of the email on forward movement. It is likely both parties want to correct the issue and move positively into the future instead of dwelling on the past.

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?

Ensure that everyone is using the same technology and that they come up with a cadence for working together. As I said before, understanding communication styles is important, especially when in-person communication is not possible. We have also been more flexible with our employees’ schedules since we understand they are taking on multiple roles (for example, maybe their kids are no longer in a physical school environment.) Make sure everyone on the immediate team is familiar with any accommodations and know how to reach out if there is something pressing that needs to get taken care of.

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?

There are many ways to make sure your organizational culture is not overlooked in a remote environment. You can schedule “mindful breaks” or video calls with team members based around a non-work-related theme. We try to do this at least once a month and participate in activities like Zoom workout and cooking classes. Get creative with the themes of these calls — we even did a virtual wellness competition where we broke up into teams and earned points by completing health-promoting behaviors like a 30 minute workout or drinking enough water during the day. Lastly, something really easy to do is take time at the beginning of a meeting to ask how people are doing and truly listening to what they have to say!

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. :-)

Empathy — you never know what someone is going through. Everyone is fighting a battle that you don’t know about, so strive to be kind in every interaction. Always check in and be genuine about it — truly listen to their responses and strive for deeper connection.

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

“A problem is a chance to do your best.” — Duke Ellington. No matter how smoothly life is going, challenges are inevitable. When they strike, you have a chance to grow and learn. I use my 3P method (Pause to Pivot to a Positive) to help get me through tough situations. Pausing to allow your feelings, pivoting out of the negative spiral, and shifting to a positive perspective have helped me to move forward with grace no matter the situation at hand.

Thank you for these great insights!



Fotis Georgiadis
Authority Magazine

Passionate about bringing emerging technologies to the market