Dennis Theodorou of Heavy Hitter Holdings: “Be More Human”

Be More Human. Because the pandemic, and its remote working implications, has impacted everyone differently, it is difficult to gauge whether someone is having a good day or a bad day just by using virtual platforms alone. On top of this, a video call may also not be the best way to gauge a staff […]

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Be More Human. Because the pandemic, and its remote working implications, has impacted everyone differently, it is difficult to gauge whether someone is having a good day or a bad day just by using virtual platforms alone. On top of this, a video call may also not be the best way to gauge a staff member’s current situation, too. Therefore, it is important to be more patient, more human, and more understanding in these times.

We are living in a new world in which offices are becoming obsolete. How can teams effectively communicate if they are never together? Zoom and Slack are excellent tools, but they don’t replicate all the advantages of being together. What strategies, tools and techniques work to be a highly effective communicator, even if you are not in the same space?

In this interview series, we are interviewing business leaders who share the strategies, tools and techniques they use to effectively and efficiently communicate with their team who may be spread out across the world. As a part of this series, I had the pleasure of interviewing Dennis Theodorou.

As Managing Director of Heavy Hitter Holdings — a portfolio of more than half a dozen recruiting, executive search, career services, human capital consulting, and outplacement services firms headquartered in Detroit, Michigan. Dennis leads the company’s national team across sales, strategy, service innovation, and client service. He holds a Logistics, Materials, and Supply Chain Management degree from Michigan State University, certifications in Strategic Management and Service Design/Operations from Harvard Extension School and has completed Six Sigma Black Belt Training.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Prior to joining Heavy Hitter Holdings, I was the Director of Operations overseeing a company of 250 employees developing restaurants. We had a lot of success and I learned a lot from that experience. However, when I was proposed the job to grow another group of companies in a completely different field — executive search and career services — I jumped at the opportunity. The human capital space is one that is growing rapidly, and our group of companies are really pushing the envelope for how great recruiting, career, and outplacement services can look like. It’s been a great journey so far, and I’m excited for what’s next.

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

I’m not a huge fan of life lesson quotes. I can usually find motivation and drive within. But if I have to point to one, I’d lean towards something like: ‘You get what you can put in’ or ‘Surround yourself with the right people’. I’m a big believer in hard work, and that hard work can be augmented when you build a great team of people who are all rowing in the same direction.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’m inspired by our firm’s founder, James Philip. Over the years I have been at the company, he has become a close friend, too.His story is inspiring to me and pushes me to strive for more growth and development — both at the company but also outside of work. James started with nothing and built a vibrant, thriving company that employs more than 50 people, all while remaining true to his vision and perspective on life. What a great story!

Ok wonderful. Let’s now shift to the main focus of our interview. The pandemic has changed so many things about the way we behave. One of them of course, is how we work and how we communicate in our work. Many teams have started working remotely. Working remotely can be very different than working with a team that is in front of you. This provides great opportunity but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits of having a team physically together?

Today, no one wants to be micromanaged, but at the same time, people have a hard time being able to manage their workday. Being in the office, people are reminded by their colleagues to continue to work. At home, there’s much more distraction. If you’re not disciplined to focus day in and day out, it is a challenge to get work done efficiently and being in an office helps minimalize distractions.

Having our team in-office allows staff to build camaraderie and find support when needed. Being able to conveniently turn around and quickly ask coworkers for advice builds confidence in tasks and daily responsibilities.

On the flip side, can you articulate for our readers a few of the main challenges that arise when a team is not in the same space?

Keeping the collective morale up is probably the hardest challenge while having the WFH schedule. You cannot gauge whether someone is having a good or bad day when you cannot walk down the hall and see their body language. Transparency is important now, possibly more than ever, and communication across the board will need to be elevated whether through company messaging or video chat applications.

Fantastic. Here is the main question of our interview. Based on your experience, what can one do to address or redress each of those challenges? What are your “5 Things You Need To Know To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space? (Please share a story or example for each.)

  1. Check-In Regularly

It’s so important for managers to check in with their staff members regularly — especially in this work-from-home environment. Managers need to make sure that not only are their staff members staying on top of their responsibilities, but that they feel supported. This may be unprecedented times, but we can all get through it if we work together and keep our motivation to achieve high.

2. Overcommunicate

Because we can’t just pop into each other’s office to provide quick updates, it is crucial for teams to overcommunicate in this virtual environment. No update is too small.

3. Set Expectations

Everyone’s daily schedules have been upended by the pandemic and work-from-home. As a result, management needs to set clear expectations for what work needs to be done, and then give staff members the freedom to execute the tasks in a manner that fits their schedules. The key, however, is that the work needs to be done on-time and at a high quality.

4. Video is Better than Phone

Despite how uncomfortable it may have seemed a year ago to hop onto a video call with your team members, this past year has proved that face-to-face contact is still as important as ever. The key to doing this in a virtual environment is by utilizing video, which we’ve found is a better way to check in with team members as it creates a level of personalization and intimacy a standard phone call doesn’t.

5. Be More Human

Because the pandemic, and its remote working implications, has impacted everyone differently, it is difficult to gauge whether someone is having a good day or a bad day just by using virtual platforms alone. On top of this, a video call may also not be the best way to gauge a staff member’s current situation, too. Therefore, it is important to be more patient, more human, and more understanding in these times.

Has your company experienced communication challenges with your workforce working from home during the pandemic? For example, does your company allow employees to use their own cell phones or do they use the company’s phone lines for work? Can you share any other issues that came up?

At our firm, we do utilize a VOIP service — and all of our employees have access to that through a physical company-provided telephone and their cellphones. Between telephone lines and the various web-based platforms and services we use to communicate, such as Slack, we haven’t really seen very many challenges on the communication front. We try to make sure that we all understand when we need to be available to our team members, and for the most part, everyone is professional and works as a team.

Let’s zoom in a bit. Many tools have been developed to help teams coordinate and communicate with each other. In your personal experiences which tools have been most effective in helping to replicate the benefits of being together in the same space?

Slack has been a useful tool since we started using it a couple years ago, but we have been utilizing video conferencing tools like Microsoft Teams more often to hold our weekly meetings for team members to see each other and continue bonding like they would in the office.

If you could design the perfect communication feature or system to help your business, what would it be?

Really, we have a lot of what we need now to be effective and communicative. Because we utilize so many different systems, software, and platforms, we have access to each other whenever we need.

Is there a part of this future vision that concerns you? Can you explain?

I believe businesses will have to learn how to reinvent themselves. Certain industries will be impacted differently of course, but the consistent theme is innovation and the ability to pivot. What worked for businesses yesterday will have to change for tomorrow. Businesses that are forward thinking and are constantly calculating risk and reward will be better off than those who are determined that their current workflow, product, or service will thrive during and after a prolonged pandemic. If executives haven’t begun to plan already, they had better begin now. Evaluating current head count, new product development and honing on current and new customers will give leaders and organizations an opportunity to survive these unprecedented times.

So far we have discussed communication within a team. How has the pandemic changed the way you interact and engage your customers? How much of your interactions have moved to digital such as chatbots, messaging apps, phone, or video calls?

In our line of work in headhunting and executive search, the majority of our customer communications pre-COVID was similar to what we do today. The biggest difference has been the inability to fly out and visit our customers as need. That said, there has been a marked uptick in our customers wanting to do video chats instead of phone, which is interesting. At the start of the shift to working from home, I remember people still getting used to being on video. People are more comfortable now with being on video, which is nice.

In my experience, one of the trickiest parts of working with 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 team member?

It is important to be proactive with giving sharing feedback with your employees during times of change. Before giving feedback, it is important to understand how your team prefers to be managed. Some staff enjoy direct feedback, whereas others may respond better with positive encouragement. Schedule a time where you and your employee and sit down to have an uninterrupted conversation. Take the time to understand what your employee is struggling with. Before closing out the conversation offer positive reinforcement, a plan to resolve the current issue, and another time to follow up on their progress.

Be mindful of employee’s mental health — it is crucial to give people the leniency to process and adapt during these changes. Having an open-door policy allows your staff to reach out when they are struggling and finding difficulty in their tasks, but managers should also proactively reach out and try to gain insight from them as well –when you make the effort to reach out, they may be more likely to share.

Can you give any specific ideas about how to create a sense of camaraderie and team cohesion when you are not physically together?

We still do our weekly training sessions within each department via video conferencing and have continued our weekly tradition of gathering with staff — even with the transition onto a virtual platform.

How can our readers further follow your work online?

They can follow JMJ Phillip Executive Search at They can also connect with me on LinkedIn at

Thank you so much for the time you spent doing this interview. This was very inspirational, and we wish you continued success.

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