Brian Matthews of Appriss Insights: Five Things You Need to Know to Successfully Manage a Remote Team

Maintaining personal connections. Today, this is much easier than it would have been in the past thanks to video capabilities, you can see facial expressions and body language. It’s easy to lose sight of that in a completely remote environment where you’re not walking down the hall, bumping into people.

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

As President of Appriss Insights, Brian Matthews is responsible for the overall strategic direction, and financial performance of this leading data and analytics business focused on saving lives, preventing fraud, and keeping communities and workplaces safe. Since joining Appriss in 2017, Brian has lead Insights’ product strategy, successfully pivoting the business towards new growth opportunities in risk management and fraud prevention, growing revenue by 70% and doubling EBITDA. In October 2019, Brian was promoted to President of Appriss Insights. As President, Brian has continued to drive growth and helped shape the culture of Insights to focus on growth over status quo, action over deliberation, and team over self-interests.

Brian has over 30 years of senior leadership in technology companies with a primary focus on strategy, business development, sales, marketing, and product management. His experience ranges from startups and growth-stage companies to Fortune 50 organizations. Career highlights include almost a decade at JP Morgan Chase, eight years at VeriSign, as they scaled from $100M to $1.5B in revenue, and growth leadership roles at eOriginal, Verint, and Vubiquity. In these roles, Brian focused on defining growth strategies, disrupting markets, launching new products and channel distribution.

Brian holds an MBA in Finance from New York University’s Stern School of Business and a BBA in Accounting and Pre-Law from Ohio University. He lives in the suburbs of Maryland outside of D.C. with his wife and three children.

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 the Midwest and moved to New York City after finishing my undergraduate degree in accounting. I learned early in my career that I didn’t like just sitting and looking at numbers; I like people. I went into banking but pivoted into a sales and marketing role, then used that to pivot again into technology.

This was when the internet was just starting to become a thing, and I was put into a strategy role at the bank to figure out the impact of the internet on both consumer and wholesale banking. I used that to pivot more broadly into technology companies that were more disruptive and moved a little bit more quickly. I’ve spent the last 20 years working for B2B, SaaS-oriented data analytics software companies.

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

The most impactful thing from a career perspective was being at Ground Zero in New York City on 9/11. Aside from just witnessing that, between my wife and I, we lost 20 friends on that day — several neighbors, young mothers and fathers of children who were our children’s playmates. So, while I wouldn’t necessarily call it interesting, it’s certainly the most memorable moment of my career and has had a long-term impact on us as a couple and as a family.

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?

Early in my career, while I was living in Hoboken, New Jersey, I was sent on my first business trip. I was in a junior sales role, and I was supposed to meet a colleague in Chicago to pitch to three clients. And I got up, I was running late, I got to the airport, got on the plane, and got all the way to Chicago. This was before mobile phones, so I had to wait in line at the airport for the phone booth to call in and listen to my messages. It turned out; the trip had been canceled the night before. I got a hold of my college roommate, met him for a nice lunch, and flew home. The lesson learned is always to check your messages first thing in the morning because your day can change very quickly.

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

Broadly speaking, don’t take yourself too seriously. Self-deprecating humor is a positive thing. You have to able to make fun of yourself. Showing your vulnerabilities and that it’s okay to make mistakes is empowering for those people around you.

Also, find time for yourself. Being a leader can be very lonely. It’s important to set aside time for yourself, whether that’s to meditate, take walks, read, or just think. Whatever that is for you, it will benefit your overall mental as well as physical health.

And finally, define who you are, your leadership principles, your expectations. That’s kind of your North Star that you come back to every day. In that spirit, Appriss Insights just rolled out a set of leadership principles that define who we are.

1. Mindset Matters: Growth over status quo

• Growth and teaching mindset: Help our people reach their full potential.
• Remote first: Support the best people wherever they are, with the best tools.
• Put customers (and partners) needs first.

2. Gettin’ It Done: Action over deliberation

• Action-oriented: Don’t be afraid to make decisions while keeping others informed, even when facing uncertainty.
• Seek discomfort: Take a step back from “We’ve always done it this way,” embracing high risk for high reward.
• Enable empowerment through transparency and alignment: Confidence to make decisions comes from alignment with mission.

3. Out of Many, One: Team over self-interests

• Inclusiveness and diversity: Constantly seeking diverse identities and experiences makes us better.
• Teams win: Every day, we win together by collaborating, supporting, and holding each other accountable.
• Equality: We listen with curiosity, speak with candor, and act with integrity and kindness.

Okay, 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 the last 20 years of my career, I’ve worked for companies that are a plane ride away. I’ve been primarily in remote roles myself and managed team members, whether they were based at headquarters or remote, who were somewhere else. Appriss Insights’ 500 employees went fully remote in March. That was a fairly seamless and smooth transition because we were well equipped to support remote employees before the pandemic.

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. Maintaining personal connections. Today, this is much easier than it would have been in the past thanks to video capabilities, you can see facial expressions and body language. It’s easy to lose sight of that in a completely remote environment where you’re not walking down the hall, bumping into people.
2. Ensuring that employees are aligned with the organization’s goals. People need a clear vision of what you’re trying to accomplish and what success looks like. When people are working remotely, they can unintentionally be working at odds with each other. So, continuing to clarify alignment is important.
3. Celebrating successes as well as handling hard conversations. Both of those things are just so much better and more easily accomplished in a face-to-face setting. You have to make sure your employees feel like they are a part of the successes, whether it be new customer wins, new platforms, or new deployments. Hard conversations are much better handled in person, but that’s not possible in most cases. As COVID hit, I would think to myself, “Gee, I really need to sit down with Person A or Person B and provide some constructive feedback.” I delayed that by a few weeks and realized I had no idea when the next in-person time would be. I realized I had to move ahead with those conversations to be transparent and continue to run the business.
4. Maintaining trust. For people who have never managed employees in a remote environment, I’ve seen unfortunate situations where they end up micromanaging their teams. You have to trust that people will get their work done, and that will show through in the results.
5. Separating work from home life. When you’re working from home, it’s very easy just to continue to work. You might decide to check email on a Saturday, and three hours later, you’re still at the computer, just because it’s there. Layered on top of that, you burn out from no social interaction and no support to care for elderly parents or young children. It’s a tough time, and people need to find that separation and take care of themselves.

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

This is always true in a remote environment, but you can’t communicate too often right now. Some people prefer emails, other people like presentations. We’ve learned through direct, unfiltered feedback from our employees that they wanted frequent communication through multiple channels. I’ve become a huge personal fan in this time of COVID of short-form video, because people like that personal connection. It’s gotten very positive feedback. They feel like there’s more of a connection to the leader and the business when they see someone. It’s a great vehicle because you can really call out individuals’ names and acknowledge success in a setting that has broad distribution. And it’s a good way to build engagement because people can add comments.

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?

Again, using video conferencing is important because it provides a personal connection. Whether you’re sharing positive or challenging news, being able to see the person’s reaction is a helpful part of the process.

Feedback is best when it’s fresh. If you end up waiting days, weeks, months, because it’s just not the right time, it’s a disservice to the individual. I’ve found in my career that most people are generally more critical of themselves than anyone else. When you give most people feedback, they discover that it ends up being less harsh than they were expecting.

It’s also important to remember that everyone has their own personal circumstances, especially right now. Some people are taking care of elderly parents or educating their children at home. Recognize that and really focus on the outcomes. Don’t get caught up in whether somebody is at their computer from nine to five. You can hold people accountable to the deliverable but be flexible and trust that they’re going to get the work done.

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

I think there’s a problem with over-relying on email. Email is imperfect, and there’s probably not a week that goes by where I send an email that could be construed in a couple of different ways, and it’s read through the wrong lens. I try not to rely too heavily upon email as a communication tool, both for one-on-one and group communications. Internally at Appriss, Microsoft Teams is the primary vehicle for meetings. I encourage people to turn on their cameras for face-to-face interaction. But I also make probably 20 calls a week to team members to thank them or check-in if I know somebody has a challenging situation.

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?

This goes back to our leadership principles. As a leader, I believe transparency is key. People need to feel like there’s not information being held back. Make sure you’re over-communicating the goals, and what success looks like, and really empowering and trusting people to make decisions. If you can do those things in a physical world, but also especially in a virtual environment, people will do good work. Trust them to get it done, and then make sure that you support them publicly and criticize them privately.

And as I mentioned before, take the time for social interactions in this environment. It was easy when you’d bump into colleagues getting coffee or in the morning and chat about the weekend or kids or sports or something you saw on Netflix. We’re humans, and we crave that kind of interaction. So, whether that’s having virtual happy hours or working lunches, don’t let those personal interactions fall by the wayside.

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?

It’s been really fabulous to see the organization organically have a variety of different approaches. I’ve had virtual happy hours, where some people bring a soda, some people bring a drink, and we chat about life and Netflix and generally not make it about work. I know some of our people are doing Friday lunches, trivia contests, and theme parties where people get dressed up as their favorite superhero. But I also recognize that people have personal lives, and you have to think about what’s appropriate for your culture and the demographics of the team that you’re working with.

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. 🙂

It’s pretty simple: Be kind. Say good morning, say hello, say thank you. Those are just little things that you can do as a leader and as a person in a challenging time to deflate stress and make the world a little better.

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

This came from my father, who passed away a few years ago: “Life is a journey, not a destination.” I was guilty earlier in my career of thinking, “When I get that promotion, when I get that round of funding, when I get that next contract, I’m going to celebrate.” And the reality is, you have to celebrate the moments along the way and appreciate the time you have with your friends and your family. Those moments will soon slip by. Enjoy the journey!

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Brian Matthews of Appriss Insights: Five Things You Need to Know to Successfully Manage a Remote… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.