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Demetrius Cassidy of In The Cloud Technologies: “Schedule a company outing”

Schedule a company outing: Bring the whole Team together once or twice a year for an outing! One of the biggest morale boosters I have ever seen is to be able to budget for a Team outing and the results that come from this. Now, this may not be applicable to extremely large groups, but […]

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Schedule a company outing: Bring the whole Team together once or twice a year for an outing! One of the biggest morale boosters I have ever seen is to be able to budget for a Team outing and the results that come from this. Now, this may not be applicable to extremely large groups, but if you have smaller teams, simply picking a place to go is a great morale booster. For example, letting your employees + families travel together to a vacation destination, (Disney World is at the top of my list) is one of the best things I have seen employers offer. We pay for employee travel, employee meals and the hotel room. This allows employees to bring their families along without breaking the bank.


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 Demetrius Cassidy.

For the last 4 years, Demetrius has been the Founder and President of In The Cloud Technologies, a leading New Hampshire based Telecommunications company. Prior to running his consulting business, Demetrius was leading a team of highly skilled engineers in the Unified Communications industry. He has been working with voice and video conferencing technologies for the past 15 years and has seen the rise in popularity firsthand of a remote workforce. Based on this, he has made it his mission is to enable other companies to adopt a remote-first workforce style.


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?

For as long as I can remember I have been fascinated by technology… by how things work and by how they’re put together. I am a tinkerer by heart, so before I started my career, I studied programming in college thinking that was going to be my path — however I quickly figured out that outside of a hobby, it was not my passion. I changed tracks to networking and soon landed a job at a network operations center that handled Voice over IP calling internationally. By nature, VoIP, and Unified Communications are inextricably linked — these technologies were always meant to be used together and this is what has held my interest throughout my career. I have seen these technologies evolve together into today’s collaboration tools. It’s these tools that enable remote productivity no matter where your team is located, that I’m excited to see future developments centered around.

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

Back in my earlier days when I was still working over at Polycom, our Director escalated an issue to my immediate attention late in the evening — the issue itself was not particularly interesting. Shortly after joining the call, one of the sales engineers decided he wanted to take over the troubleshooting with an already very anxious customer. Now keep in mind their phone systems were completely down. This quickly led us to request that his manager force him off the call so I could continue doing my job…After a few uneventful minutes, I figured out the root cause, got the customer working again and then hung up (it was after 5pm and I was ready to go home).

Several uneventful weeks passed until one day, during our morning meeting, the Director personally messaged me asking me if I was going to join the morning standup call. I was a bit baffled but did not think much of it at the time. That was when I found out that I made the customer cry! They let a few moments pass before they explained it was because she had such a stressful day, it was because she was so relieved, we fixed her issue and that her business could continue. I ended up getting an award from the company and can now proudly say this is my best achievement. Making one of our customers cry.

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

You can’t control what other people think about you.”

It is very hard to take feedback from others when you are constantly worried about how your peers or network contacts think about you. In business, I cannot even count how many times people have said “no” to me during a pitch in a meeting. But that really does not matter. What matters is how you handle it, by not taking these things personally, moving on and finding the one that will say “yes!” It is about what you can control. You cannot change how others perceive you. All you can do is to keep presenting yourself in a positive way and move on.

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 honestly do not have any single person I can point to and say, “this person is the one who helped me succeed in life”. The truth is, there have been many people across different points in my career that have impacted very meaningful feedback that changed how I interact with others or how I approach a problem. There have been many leaders I have worked under, and to this day still look up to. Managers, Directors, peers… everyone imparts a bit of knowledge and wisdom. The key is to take that bit of wisdom and use it to shape your behavior in a way to help you navigate this complex life.

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?

The biggest impact is when you’re sharing a physical space is that it is easy to communicate, shadow and gain knowledge with our peers. When you have a team in the same location, you tend to get better socialization, better interaction, and sometimes better productivity than when you mix and match remote employees with a local team.

Socialization is honestly the greatest strength compared to what’s initially thought to be missing with remote teams. In the past you could argue that being on-premises would grant you better security and is what we expect, but this is no longer true. With so many cloud based tools, the rapid evolution of technology and corporate inability to keep pace, I now consider a physical office about as secure as that public cloud. Even with your database, social security numbers and all that private information in it. (https://www.cnn.com/2019/06/05/perspectives/labcorp-quest-diagnostics-data-breach-social-security-numbers).

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?

Collaboration with your Teams is a big one, because without the right tools and policies in place, there’s sure to be some issues. One thing we see happening is people end up in an endless video conferencing scenario, especially from large corporations. Sometimes we see a Team that is unable to effectively work together because there’s been a communications break-down. We find this usually comes from leadership that has not kept up with the frantic pace of technology and is struggling to adapt and guide their organization.

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. Use the right tools: Collaboration Tools such as Microsoft Teams are vital to a properly functioning remote team. Period. I think the best example I can give you is for HR — one of our client projects was for HR teams that deal with talent acquisition, who needed a way to collaborate with their peers. They previously used simple shared mailboxes and calendars but found it difficult to setup for non-technical people and that it was prone to other team members’ lack of information. They were unaware of what calls were scheduled, with who and what the results were.

With Teams, we created a group HR channel, added a built-in calendar that gets automatically shared with the whole Team, and then saved resumes and notes about reaching candidates. This allowed HR to now collaborate in real-time, without having to be physically present in the office.

2. Schedule daily standup calls: These are informal calls with the whole team to discuss daily tasks, challenges and to request feedback/assistance from peers. While I prefer daily calls, we can reduce them to a few times per week if appropriate.

3. Schedule weekly individual calls with your Team members: Design these to share constructive feedback and to understand what challenges are faced and discover how you can help.

4. Schedule a company outing: Bring the whole Team together once or twice a year for an outing! One of the biggest morale boosters I have ever seen is to be able to budget for a Team outing and the results that come from this. Now, this may not be applicable to extremely large groups, but if you have smaller teams, simply picking a place to go is a great morale booster. For example, letting your employees + families travel together to a vacation destination, (Disney World is at the top of my list) is one of the best things I have seen employers offer. We pay for employee travel, employee meals and the hotel room. This allows employees to bring their families along without breaking the bank.

5. COMMUNICATION — I cannot stress this enough, if you do not have transparent feedback mechanisms and communication systems in place, none of the other building blocks will fall in place. Having meetings for the sake of having meetings is not helpful. What is truly helpful is being able to properly collaborate with your team, as your success hinges on this.

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?

We have taken a remote-first approach, so this is not something my company has really experienced. For our clients, we provide all the tools that employees need to be productive, no matter where they’re located. We also expense employee cell phone costs, but at the same time we do not expect (or want) employees to share their personal cell numbers with customers. On top of this, not having to deal with physical offices and limiting hiring to a particular city, town or region has allowed us to acquire great talent we would not have been able to find otherwise.

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?

While I might be slightly biased and prefer Microsoft Teams, I will give Zoom proper credit here. Many groups quickly needed a virtual meeting platform (schools being a great example) and Zoom was there to fit that need. But knowing them both among others, Microsoft Teams has rich integrations with word, excel, outlook plus the countless plugins that extend the ability of this platform. Being able to have a shared calendar, or a group task list for an existing project or being able to quickly call all the team members (say during an outage) with one click are just some of the advantages of having a proper collaboration platform in place.

We need quick and efficient means of communications, pandemic or not — and Microsoft Teams is absolutely my choice for a collaboration platform.

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

Honestly, I would love to have some sort of Augmented VR communications system. Body language is just such a huge part of human communication that sometimes it feels like video conferencing is not enough. VR would take us one step closer to mimicking the benefits of having a physical presence. This will be very possible by the time Augmented VR becomes the norm for collaboration, we will also be able to replicate physical touch. I would love to be able to shake the hand of my customers, without having to hop on a plane first.

The technology is rapidly evolving and new tools like VR, AR, and Mixed Reality are being developed to help bring remote teams together in a shared virtual space. Is there any technology coming down the pipeline that excites you?

I am really excited for the potential of augmented reality technology that’s currently in development by multiple market leaders. This has the potential to revolutionize how we interact not only with our coworkers, but also how we can virtually interact with designs and systems that can be thousands of miles away from our current location.

The potential impact for this technology is huge and I cannot wait to try it.

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

As much as I am excited for Augmented reality in the business space, I am quite the opposite in thinking about the consumer space. This double-edged sword has many negative implications for personal privacy. What is stopping advertising companies from using this technology to track your every move? We will need to develop some new privacy regulations when this technology is becoming commonplace. These are concerns I have about the future.

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?

Before the pandemic started, most of our interactions with customers and peers happened mostly over voice. Audio conferencing has been the staple of communications for decades, going back to the 90s. While video conferencing technologies have been around for many years as well, they were never mainstream. Until now.

If the pandemic has shown us anything, is that we need the face-to-face interaction we used to get prior to the lockdowns. This has reinforced the idea of video conferencing when interacting with your peers and customers and how important body language is. Prior to the pandemic, most of our interactions with customers were phone-based, even if we used a UC platform, our calls were audio-only. Now, when dealing with new customers we tend to turn on our cameras. Out of respect.

When we interact with our peers, it is no longer sufficient to rely just on audio and email. Now we have rich interactions with collaboration tools. Now, the whole team can stay in-sync and work in real-time, even though we’re at times, very far apart. I truly believe video conferencing is the future and is what we can expect going forward, even after the pandemic ends.

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?

This is a bit tricky. Honestly it really depends on the relationship with your remote team member. I have adopted a guide where I do weekly one-on-one calls with my team members and for these calls we require they enable video. The idea is if you are having a conversation and offering feedback, we need to see the other person’s face to get the correct idea and context behind their feedback. Body language is huge and should not be underestimated.

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

The best tip I have is to stay in constant communication. To have either daily or bi-weekly stand-up calls with the entire team. The idea is to focus on the topic of each call together and can share what everyone is working on. To offer feedback and advice in an open and constructive forum. This is different from say… a project management call because it’s internal and we are simply sharing and gathering feedback. Ideally, we will have video enabled for these calls, but it is not mandatory.

Ok wonderful. We are nearly done. Here is our last “meaty” question. 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. 🙂

Did I mention how I believe the 9–5 workforce is dead? With so many technologies being “cloud” based, just enabling your employees to choose which days or times they are in the office is a real game-changer in this industry. Just think, the difference between working from home 2 or 3 days a week can save a couple with young children thousandsof dollarsin childcare costs a year. The implications and benefits are huge and are not necessarily just oriented monetarily.

If I had to say one thing, employers, please enable your employers to work remotely with flexible hours. When this pandemic is over, if you do not enable a flexible workforce, your competitors will. You will lose your best talent.

How can our readers further follow your work online?

Please follow us on Linkedin: https://www.linkedin.com/company/inthecloudtech

You can also checkout our tech blog on our website: https://www.inthecloudtech.net/category/blog/

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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