Five Things You Need To Know To Successfully Manage a Remote Team

Click here To read the original Authority Magazine article.

Time management. Some individuals find managing their time more productive when in the office and others do a great job managing their time while working at home. For junior folks who may be new to working remotely, they may encounter the challenge of how to balance and prioritize time, so need a little more attention and guidance.

Asa part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Michael Dobson.

Michael Dobson is SVP, Digital Media iNvolved Media, an independent strategic digital agency that plans, executes, optimizes, and measures cross-channel media campaigns. Prior, Dobson served as Vice President, Social Media Strategy & Buying with Horizon Media, where he was responsible leading and managing the agency social media practice, focused on strategy and business outcomes. Previous experience includes Head of Marketplace Media, Social, Search, Programmatic Agency Lead with Crossmedia, Director of Social Media/Digital Marketing & Advertising Strategist with Media Assembly — Unique Influence and Marketing Business Development, Ecomm Marketing Manager with Michaels Stores, Inc. Dobson also ran his own consulting firm, planning and executing business marketing and advertising campaigns for his clients.

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”?

Mybackstory is a little backwards compared to most in the industry. I started in the marketing and advertising world on the client side, working at Pier 1 Imports and Michael’s corporate offices in the DFW area. I ended up working in marketing focused on eCommerce business as it was just taking off. To date myself a little, social media was primarily organic and a little boosting to get likes and followers and search was simply branded and non-branded key words. From there we know how things evolved into the advertising space and grew with more digital investment over the years, which my career followed. I crossed over into the media agency world by joining a boutique agency focused on social and search advertising that was acquired by a larger global agency a few years later. When I started we were 5 people and 2 dogs, and when we were acquired we grew to 45 people and 5 dogs. This is what brought me to NYC in the media ad agency side. Most recently, I left Horizon Media where I ran the social practice to join Active International to run the full digital team, including our subsidiary iNvolved Media.

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

Do I have to pick just one?! Whenever I worked on a new business pitch, I was always surprised by where it took us. You learn so much about people in a short period of time and of course, a short amount of sleep during that time. One night we were having a strategy brainstorming session (because it’s always like a second job with new business pitches) in a large conference room, and all of a sudden, this guy I didn’t know well got out of his chair and leaned against the wall to do a headstand. And then, he started talking as if we were just brainstorming. Like it was no big deal. I’ve always told people if they have a chance to be part of new business, it’s one of the best ways to learn well beyond your everyday job.

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?

Let me tell you about the funniest mistake I made before I even started. While interviewing for a position at an agency that used a technology called “Nanigans,” I mistakenly referred to it as “Shenanigans.” The interviewer looked at me for a minute with a tilted head and we both just started laughing. I walked out thoroughly embarrassed, but I wound up getting the job. My lesson learned was to not verbally repeat something that I wasn’t fully clear on how it was pronounced (you may have had to be there to know how funny it really was!).

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

As most of us have seen or experienced firsthand, burnout must be identified and addressed before it hits a tipping point. It’s important to look at whether burnout is temporary due to certain circumstances — perhaps a looming deadline or new business pitch approaching — or a long-term problem that needs to be fixed. Having an open dialogue is key for anyone managing employees — understanding how people are feeling about their work and the balance of their time — both personal and professional — is key. And once you think you’ve fixed the problem, even if it’s just a deadline passing, following up directly to be aligned is important to let your team know you are listening and you care.

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?

For about six years I’ve managed people remotely in one form or another. I’ve had teams of people in other offices which I’ve always considered to be similar to remote working from anywhere. If I’m sitting in New York City and I’m managing 25 people in Los Angeles, I’m working in the same way if they’re in my office or in another space.

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. Connecting personally. It’s hard to connect personally when not in person and in some cases, while we may be in professional positions, human interaction to have a level personalization is part of how we communicate.

2. Time management. Some individuals find managing their time more productive when in the office and others do a great job managing their time while working at home. For junior folks who may be new to working remotely, they may encounter the challenge of how to balance and prioritize time, so need a little more attention and guidance.

3. Collaborating in a brainstorming setting. It’s simply hard to brainstorm over a conference call or video call. Yes, technology has made things easier but it’s just simply not the same as being in the same room together.

4. Training. “Let me show you…” Is a little harder when you’re remote. Technology has allowed us to train remotely and some people have been doing this for some time but in some cases, there’s no comparing hands-on, in-person training experience.

5. Company/Team culture. Showing and driving a company culture is difficult when people are not brought together to connect. Again, technology has helped that but after the last year and a half, I think we can all admit we’ve had enough Zoom happy hours and virtual games to build morale with our teams.

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

One of the most sensitive 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 it’s difficult to convey this when remote.

Separately, in regard to bringing the team back together again — we have planned to reopen the office in a hybrid manor this fall. As part of this, we have taken in consideration the space people return to. I want the team to feel like going to the office is a welcoming place to collaborate and change up the environment from where they’ve been working over the last year and a half. We have given the space what I like to think of as a “facelift” to create a comfortable, open space that fosters collaboration and creativity, and made sure the technology capabilities are seamless for those who have video calls.

Can you give a few suggestions about how to best give constructive criticism to a remote employee?

This is a really great point. If I know I’m going to have a potentially difficult or sensitive conversation, I always encourage to do it with video on. Following up on what I said above, it’s the closest I can come to showing my facial expressions and body language to help set the tone in addition to the words I’m saying. I also try and be respectful and silence my cell phone and minimize my email so I do not appear to be distracted looking at other items on my screen when having this discussion.

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

I try to avoid going too deep via email when it comes to giving critical feedback. I personally find it easier to do it over the phone or via video. But I generally will follow up with an email outlining the conversation and the main points addressed. I also find it helpful to set a time to readdress the concern, usually within a week or two, to make sure the items we discussed are happening, such as reaching goals or milestones.

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?

We’ve all learned that there’s a lot of small talk that goes further than you would think. For instance, passing by someone’s desk to chat about a project is no longer a thing. Most of the conversations we have now require a meeting or a set time to chat through something. I’ve encouraged and trained my team to know to ping me anytime and I’m always willing to jump on a video or screen share when needed. One challenge for anyone making this switch is understanding that a screen share or screen take-over can go a long way. And recording trainings and meetings has been a lifesaver.

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?

Finding different touch points for people to interact together is crucial when you don’t have people physically together. Specifically, conducting virtual events has been successful. Bringing people together is the starting point. Some of the things I’ve done have ranged from learning sessions, external seminars, game nights, happy hours and diversity education events. And we can’t forget about our new hires and the onboarding experience. Making individuals feel welcomed and well-positioned for success is a priority in the first few weeks of them joining a new organization and team and in this new remote world we live in, has been a new challenge I’ve had to face as a supervisor in creating this new experience of adding a member to our work family 100% 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. 

Oh my, no pressure! The past year has opened the world’s eyes to diversity, equity and inclusion, and I’m pleased it’s been brought to light to help encourage change. I have learned a lot in the last year but not enough. I have witnessed and continue to see the gaps in DEI education and acknowledgement across organizations. Change will only happen when we use our voice and demand change to take place. I encourage everyone to be curious, ask questions and drive change and am proud that as a leader in my company, have worked with the management team to institute change in our business units.

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

“No matter who you are or what you look like, how you started off, or how and who you love, America is a place where you can write your own destiny.” President Obama speaking on marriage equality in 2015.

This quote connects and relates to me in many ways and I appreciate the fact that I can “write my own destiny” both personally and professionally.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!