Joe Dupriest of NextUp Ventures and NextUp Partners: 5 Things You Need To Know To Successfully Manage a Remote Team

A final piece that gets lost in managing remote teams is not having direct oversight into what the employees are doing and how projects are progressing. Even small things, like stopping by someone’s desk to check in gets lost, as a phone call just isn’t the same and can be more of a nuisance. This is particularly challenging when getting a new employee up to speed on projects and helping them balance their workload. There has to be a lot of trust between manager and employee to successfully overcome this hurdle.

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

Joe is a high-energy, decisive senior executive with more than fifteen years of progressive leadership experience, driving market penetration and business growth within sports. With an engineering degree from Georgia Tech coupled with an MBA from Duke University, he served as CMO for Monumental Sports & Entertainment during a period of explosive growth and change. Joe launched Monumental Sports Network, the first OTT platform for regional sports, and has won five NCCB Emmy Awards. Most recently, he co-founded and launched NextUp Ventures and NextUp Partners, a multi-solution consortium designed to empower leading, emerging, and startup sports companies to maximize their businesses amidst today’s dynamic landscape.

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 outside of Atlanta and always having an affinity for math and science, it was a foregone conclusion that I would go to Georgia Tech and spend my life as an engineer. While I was at Tech, I got bitten by the sports bug while working gamedays with the Atlanta Braves and set about finding a way to combine sports and engineering. After graduation, I spent the first few years of my career as an industrial engineer with FedEx Express, which eventually led me to Duke’s Fuqua School of Business. I spent my two years there networking with anyone and everyone willing to give me 15 minutes on the phone to learn about various career paths within sports. I did my summer internship with the Durham Bulls, which is where I met my now-wife. That experience was where I first combined my analytic/engineering background with the evolving needs of sports teams. At the time, not a lot of teams were doing much with analytics and data, so that provided the opportunity to carve out a niche for myself. Following graduation, I landed in Philadelphia working for the Eagles. Relationships are everything within the sports world, and the relationship and trust I built with my boss, Tim McDermott (now president of the Philadelphia Union of MLS), led me to D.C., where I also worked for him at the Washington Capitals. I moved my way through the ranks to CMO of the Caps and eventually CMO of all of Monumental Sports & Entertainment, including the Washington Wizards and Mystics. I then spent two years in the corporate world but always had an interest in returning to sports and entertainment, which is what led me to co-found and launch NextUp Ventures and NextUp Partners this summer. To bring the story full circle, the relationships I built going all the way back to my part-time work with the Braves in the late 90’s are what made my career a reality. We have united an unbelievable team of executives from across sports, all of whom have strong working relationships with someone else on the team. Even working remotely, everyone immediately jelled and we were able to hit the ground running. Because of our diverse team with experience across all facets of sports, we are able to quickly begin work with sports companies at all stages, from early startups to established brands and teams.

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

When you spend so much of your career in sports, there’s definitely no lack of interesting stories. My first lasting memory occurred in 1996, my first year working part-time for the Atlanta Braves and also the final year they played at Atlanta-Fulton County Stadium. This stadium had extra meaning to me — it’s where I grew up going to games and watching Dale Murphy and Bob Horner, way before the team’s run of success in the 1990s. The Braves were in the National League Championship Series and were down three games to one. They came back to tie the series, bringing the decisive seventh game back to Atlanta, where I worked the game. The Braves won that game handily and I somehow ended up on the crew that carried the stage out onto the field for the postgame trophy ceremony. From there, we got to sit in the dugout and watch everything as a young Chipper Jones sprayed all of us with champagne. Unfortunately, the World Series did not end with a similar celebration…

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?

This story isn’t necessarily early in my career but it is early in my time with the Washington Capitals. My director of game entertainment was out for the birth of his first child, so one of our other producers and I stepped in to help run the show (which consists of calling what videos play on the videoboard, what music is played, getting the crowd hyped, etc.). I had zero experience doing this live, but fortunately we had a veteran team that handled most of the work — except for one instance where I approved running the replay of a questionable call by the refs against one of our players who had just made a not-so-smart play. Within five seconds, our phone rang and it was the General Manager calling to not-so-calmly explain why that was a bad idea (to be honest I didn’t even notice there was a phone on the desk until it started ringing). What I didn’t fully grasp prior to that was the dynamic between the business side of hockey and the team side and the importance of building a strong relationship from day one so that expectations and trust are there. Over time, I developed a great relationship with our General Manager and learned a lot from working with him. I wish I had started doing that much earlier!

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

I was reading your interview with Sharon Napier of Partners + Napier and what she said really stuck with me. It’s not about work-life balance, it’s about work-life integration. But it’s not enough to encourage your employees to practice it; for it to really be effective the CEO has to live it as well. Showing your employees that you see the importance of proper integration in your own life and ensuring you don’t lose focus on what your true priorities are is essential to avoiding burnout and thriving consistently. Personal priorities need to remain priorities all the time, not just when work allows it.

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 during the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

Within sports, the idea of remote teams, historically, has been a foreign concept. Until the last few years, I only had experience working with teams face-to-face. However, I spent more than two years working for Shop Your Way as their head of marketing, and much of that was done remotely. I traveled to the corporate office in Chicago a handful of days per month, but otherwise I worked remotely from my home as did a number of the members of the leadership team.

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. One of the toughest challenges is the ability to have productive brainstorming and whiteboard sessions. Many of the best ideas and solutions come from a collaborative group, a marker and a wall-sized whiteboard. Thinking back to my early days with the Capitals, we were closing in on the playoffs and needed a campaign to capitalize on the energy of the fan base, which is when we created Rock the Red. What started as a brainstorming session went on to serve as the team’s rallying cry and tagline for almost a decade. That was developed by getting the key people in the room and listing ideas, crossing ideas out, evolving, combining, and overall brainstorming until we had something great. That same type of session is much more difficult to conduct remotely.
2. A second challenge is being able to “read the room.” Observing feedback through tone, body language, mannerisms, and expressions is challenging when you aren’t in-person, even if meetings are done via video. It is very easy to misread a reaction and have things snowball. A confusing video call with no ability to grab a face-to-face could lead to an email where tone can get completely misconstrued. For example, if you aren’t in-person when presenting new ideas or discussing solutions to present to a client, it is easy to miss unspoken feedback especially if the employee is hesitant to tell their boss that something is a bad idea.
3. Distractions! This is a challenge for everyone, not just the manager. It is easy to get sidetracked, like when the kids pop into the office to ask a question or tell a story. Fortunately, my kids are pretty good with boundaries, but it has happened more than once where my 4-year-old interrupts to get on the video call with me. Separating your home life and demands from work is much harder when they both occur in the same location.
4. What may be the biggest challenge is team building. When I was at the Capitals, we had a team meeting once per week where you can discuss more than work. If it was someone’s birthday, our VP of marketing would make an ice cream cake for the group. This type of stuff is extremely important when building camaraderie amongst the team. Now, in a remote environment, it is much more difficult to develop authentic relationships. Building trust takes longer, as the interactions that do occur now are almost 100% focused on work.
5. A final piece that gets lost in managing remote teams is not having direct oversight into what the employees are doing and how projects are progressing. Even small things, like stopping by someone’s desk to check in gets lost, as a phone call just isn’t the same and can be more of a nuisance. This is particularly challenging when getting a new employee up to speed on projects and helping them balance their workload. There has to be a lot of trust between manager and employee to successfully overcome this hurdle.

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

1. For online brainstorming sessions, I would encourage having those be only on video versus phone and utilize screen sharing whenever possible. That keeps people more engaged and the team can use that screen as a pseudo whiteboard to add notes as the team discusses. I would also limit the length of these, as it can really drag on and people will begin to mentally check out. I think the maximum length should be one hour for any single session.
2. Similar to brainstorming, I think any meeting where back and forth feedback will be given should be done on video as well. From a culture standpoint, it is extremely important to create an environment where feedback is welcomed and everyone will be heard. If the team feels they can be open, then ideas and feedback will be more readily verbalized. However, picking up on nonverbal cues will take time especially when dealing with new employees.
3. I have found that the best way to avoid distractions in my house is to deem my work area off-limits, except in the case of emergencies. It is important for the kids to understand that when I am there working, it is no different than if I were in an office downtown. Once a meeting gets disturbed, it can be hard to get back on track and it is easy to lose engagement with the team if they don’t think I’m 100% focused.
4. I believe team-building can still be done virtually, it just has to be done in a different way. Recognizing birthdays is a prime example: while it would be great for everyone to share a cake, it will still go a long way in recognizing key personal moments. It is also very important to take the time in meetings to call out great work and recognize employees. The banter before and after in-person meetings is often where people get to know each other, so at times I have intentionally started a video call late so the attendees have a few minutes to chat amongst themselves. It is important to keep the human aspects of meetings (and not only focused on work), as relationship-building is key to a successful team.
5. To overcome the lack of day-to-day direct oversight, I recommend setting up multiple one-on-one check-ins throughout the week with each employee or small groups. These shouldn’t be long meetings that people dread, but instead are quick 10-to-15-minute chats that ensure the employee is on track. Remember to also give them an opportunity to ask questions and provide feedback. It is important for the manager to get to know their employees and what works best for them and set up the length and scheduling so that the employee values the time and doesn’t see it as a distraction or obligation. I also believe it is vital that the manager develop a culture that encourages employees to reach out with issues and be responsive at all times. I see a big part of my role as ensuring that I don’t hinder progress for my team and strive to make sure they are never waiting on me to keep things moving.

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?

That’s a great point and ties into my challenge of “reading the room” without being in the room. The first thing that is crucial here is to have as many of these conversations as possible over video, so you at least have the opportunity to read facial expressions. However, it is important that video not be used only for giving critical feedback or the employee will begin to expect uncomfortable conversations for all video invites and go into them apprehensively. Video is not only important for the manager to read the employee but is just as important to enable the employee to read the manager. Without being face-to-face, you must remember that the employee also can’t tell if you are upset or using it as a coaching moment. The manager should ensure that they choose the right facial expressions and tone to deliver the message.

Another key suggestion is to be open and honest with employees across everything and encourage them to be honest with you as well. Point out the good as well as the bad, and give them the opportunity to tell you what you could be doing better. It is critical that the manager listen as well as deliver feedback. A strong relationship with the employee can help overcome the inability to interact face-to-face.

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

One of the most difficult things to do is convey the right tone in an email, and it is very easy for unintended tone to be what the employee takes away from the message. The manager needs to be consistent in the tone that they use over email and in person. That goes for the flow of conversation as well as word choice. If the wording of the email is more direct and focuses on the problem, whereas an in-person conversation would be more conversational with balanced feedback, then the email will come across as much more critical. If you must deliver critical feedback via email, point out both problems as well as solutions. Don’t just tell an employee where they took the least desirable path or made a mistake; instead offer solutions that will help them avoid problems in the future. Whenever possible, point to prior examples of when the employee did a good job as a lesson for how to handle this situation differently next time. In general, however, I would avoid giving constructive feedback in email whenever possible unless you have a strong relationship and work history with the employee so they know how you operate. If it is a new employee and you are delivering this type of feedback for the first time, I would avoid the email until both sides learn to read each other.

Can you share any suggestions for teams that 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?

I would suggest keeping things as consistent as possible, including both the cadence of meetings and flow. Teams that understand expectations and know each other pretty well will make a much easier transition to remote work. In-person, they know which team members don’t mind people stopping by their desk for a few minutes to catch up on a project and which team members prefer more structure. If someone knows a teammate doesn’t like being interrupted at their desk, then they probably also won’t appreciate multiple random phone calls when working remotely. It is also important that the manager stay in constant communication with the team during the transition, to understand what challenges they are facing and any concerns they have. Addressing these problems quickly will reduce tension and ensure that everyone feels productive and efficient.

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?

The manager needs to set clear expectations on hours, availability, response times, and meeting protocol. Even when remote, there must be a structure to follow, and this consistency will be important for the team to operate. Without a clear communications structure, your team will become frustrated with each other and you. Additionally, it is important for the team to meet together without the manager, as often or even more than they would in-person (to make up for lost chance conversations in the hall or break room). A good manager will balance not micromanaging the team, setting clear expectations, and keeping track of workload. This helps employees avoid bad habits while working remotely.

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 don’t think I need to inspire this movement, as it has been an issue for years and a hot topic recently: we need a renewed focus on our education system. Education is the key to unlocking potential in each new generation, but everyone can agree that it has problems. For every year that we don’t fix those problems, that’s another year we miss improving our future, letting millions of kids and families down. I’m not going to get political and propose what I think the solutions are, but it needs to be analyzed top-to-bottom for:

1. Inconsistency in educational opportunities, both across the country and within states;
2. The amount and source of funding for public education;
3. The role that each level of government should play;
4. The overall support given to teachers.

It’s time to find solutions. We can’t just keep kicking the can down the road.

Can you please give us your favorite “life lesson quote?” Can you share how that was relevant to your life?

I feel like I’ve made it through this interview by barely mentioning Duke so far, which my friends and family probably think is quite odd, so I will finish with a quote from Coach K: “Everyone’s ideas should be heard. It doesn’t matter who gets credit, as long as you’re working towards the same mission and shared purpose.”

I think this is critical for any leader, whether it is in business, sports or the community. I have always tried to be the type of leader that listens first. The best ideas rarely come from the person at the top, but the person at the top should be able to listen to everyone, identify the best ideas, refine them, and help the team implement them successfully. I will finish with another non-sports-related quote from George Clooney that I think captures this concept: “You never really learn much from hearing yourself speak.”

Thank you for these great insights!

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Joe Dupriest of NextUp Ventures and NextUp Partners: 5 Things You Need To Know To Successfully… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.