Robin Clayton of fifty-five: Five Things You Need to Know to Successfully Manage a Remote Team

Adding up various experiences over the years, I have approximately 4–5 years of experience managing remote teams and overseeing remote delivery. My first time overseeing a remote delivery project was in my mid 20s; my team was a mix of onshore and offshore, and the client had an offshore team as well. I was onsite with clients a few days a week and oversaw ongoing delivery. The timezones and ability to maintain a work life balance while working between EST and IST (India) were very challenging.

As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Robin Clayton Executive Director at fifty-five.

Robin Clayton is a management consultant with 12+ years of experience. Over the span of her career she has handled strategy, business cases and roadmapping, solution focused project delivery as well as product management, while working with leading brands to digitally transform their businesses. The last 12+ years have enabled Robin to develop a unique combination of digital strategy and data-driven delivery experience that enables her to bridge the gap between strategy and practical application, with experience implementing change across global organizations with measurable impacts.

Robin currently leads the US consulting practice and is responsible for leading client delivery and driving growth across accounts, building partnerships with Google and BrandTech companies, leading RFPs, managing the US consulting team, and driving a data-driven delivery agenda.

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’ve always been in client-centric roles from different perspectives of consulting. I started in traditional business consulting and moved into digital, eCommerce and omnichannel, which evolved to business strategy and digital transformation. After leading digital transformation programs, I realized the two categories global organizations tend to break down in their efforts to drive change and realize rapid results are 1) people and processes, and 2) comprehensively connecting, acting on, and measuring data. After realizing that, I decided to slightly pivot and focus on those two particular challenges, which is where I find myself now — leading the consulting team at 55, The Data Company.

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?

I was a management science major, which loosely translates into business focused math. A coworker asked me if I knew anything about derivatives going into a client conversation she had. I proceeded to teach her mathematically how to solve for derivatives, as if it were a math class homework assignment. I was feeling very good about myself for teaching her that in such a short amount of time. When I asked her how the conversation went, she told me that derivatives were in fact a financial asset. Oops.

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

Now is the time to check in and relate to each other on a human level. It’s ok to be less buttoned up and more informal than we are used to while working in traditional corporate America. Whether you’re talking with employees, clients, peers, mentors — we are all human and are all undergoing an unprecedented human experience. It is common ground that we can all relate to, connect on, and empathize with. In a leadership position it is up to you to take ownership and set the tone and example.

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?

Adding up various experiences over the years, I have approximately 4–5 years of experience managing remote teams and overseeing remote delivery. My first time overseeing a remote delivery project was in my mid 20s; my team was a mix of onshore and offshore, and the client had an offshore team as well. I was onsite with clients a few days a week and oversaw ongoing delivery. The timezones and ability to maintain a work life balance while working between EST and IST (India) were very challenging.

The first U.S. based remote team I managed was about 5 years ago. I oversaw a distributed five-person team of business analysts who were deriving business requirements and delivering a website redesign for a large global cruise client. The offshore experience aided in my success while managing the remote team. Since then it’s been a mix of offsite, onsite and offshore delivery.

Currently I remotely manage five reports on my consulting team, as well as two indirect reports.

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. Ensuring everyone is engaged with work and their projects,
  2. Helping reports compartmentalize the ongoing world and social events while remaining focused at work; check in early and often. Instead of a quick coffee or interpersonal conversations that occur more naturally in the workplace, you need to make time and prioritize those conversations remotely.
  3. Having a line of sight into employees’ emotional well being and potential burn out.
  4. Fostering a sense of culture and connectedness even while everyone is dispersed
  5. Ask the team to come up with remote activity ideas they want to try out and have them drive and plan the team activity themselves. Let them own the agenda and encourage them to get creative and try new things. Some will stick, some will not.
  6. Furthermore, we’ve incorporated emotional cultural values into our weekly team meetings, with a vote each month for a new value that our team feels it needs to be successful. We then give kudos and acknowledgement to teammates that have displayed this value over the week, during the team meeting.
  7. Helping less experienced employees (especially more junior, college hires) be productive in a remote environment
  8. In addition to tactics for helping everyone stay engaged, establish a foundational structure for ways of working; ensure channels of communication are defined and open with clear expectations and handoffs. Proactively schedule in time for feedback and reviews to ensure everyone is set up for success. Additionally, identify important conversations or connections that need to be made and ensure a forum is put in place to foster those conversations.
  9. Accommodating time zones and flexibility of schedules
  10. Currently, with team members working in Paris, New York, New Jersey, Connecticut and California, our team members are working across various time zones. We have to balance delivery with where our clients are located, and therefore, we are proactively scheduling time where needed to alleviate burn out. We are also working to ensure coverage for the timezones in which our clients work out of. We have also implemented a loose structure for team meetings and checkpoints, not requiring all team members to attend every meeting.
  11. Onboarding a new employee — This is one of the most challenging aspects of remote work. Managing a remote team when everyone already knows each other and has built a rapport and camaraderie is one thing; onboarding a new employee is another. Helping her get started and hit the ground running has been a challenge. Helping her feel connected with the broader team having never met most of them in person has been even more difficult. She is navigating new ‘eveythings’; new people, new team dynamics, learning how to navigate a new company, and adjusting to new clients and project work; it’s a lot of new variables to juggle all at once.

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

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?

I emphatically agree with you on this point. In life you generally tailor your message to your audience, and the same is true for feedback. There is such a range in how people take feedback. Some people are very good with direct, honest feedback and some find it harsh and may default to becoming somewhat defensive or aggressive in their responses. Being remote adds one more layer. I like to provide near real-time feedback whenever possible, whether positive or critical.

It is important to keep constructive feedback in a 1:1 situation remotely factual and objective. There should be an emphasis on explaining the reasoning behind why the behavior needs to change. Avoiding pronouns can be helpful to make receiving the feedback feel less personal and more like a broader learning experience. When giving constructive feedback, it’s important to lead with setting the expectation as an area of growth or an opportunity to improve, instead of picking apart what someone has done wrong or failed at. It’s also important to be transparent and honest, ensuring that everything is documented and evidence is provided to support your feedback.

In a remote environment, it’s very important to ensure that positive feedback and positive reinforcement are prioritized. This results in employees ability to compartmentalize constructive criticism as one of many data points. We try to infuse this on a few different fronts: as a broader team, within client or project teams, and also at a 1:1 level with individuals.

We spend five minutes each Monday during our weekly team meetings, in which the entire team is present, recognizing accomplishments. We give kudos and feedback based on the theme of the month, which is a cultural value we all vote on, such as ‘unique’, ‘curious’ or even ‘appreciative’ and ‘supported’. Last month was ‘unique’.

Acknowledging and celebrating success together is important. I try to give positive feedback immediately and with visibility to the broader team. We leverage Slack for communication and have separate channels for all clients. For example, when an employee does a great job navigating a challenging conversation on a client call, immediately give positive feedback in the channel. This results in both visibility for the entire team, and allows us to celebrate each other’s wins while also reinforcing the standard. In remote times we are celebrating all wins, even small ones.

On a project by project basis, or after a big meeting or presentation, we try to carve out time to talk about “pluses and deltas” from the meeting. What went really well? What do we want to modify? What in retrospect could we have done differently to adjust something that didn’t go as planned? Making it a collaborative group exercise is super important. We even go as far as doing this with clients, to ensure they feel listened to and that their input is incorporated. For example, we conducted a two day remote training session that is usually a very interactive, hands on workshop. The sessions include live facilitation, exercises, teamwork and breakout sessions. Following the conclusion of day one, we alloted 15 minutes to conduct a “pluses and deltas” session with clients. We were then able to make adjustments and incorporate their feedback for day two.

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 sending significant constructive feedback in an email with nothing else. If I am going to share constructive feedback via email I always try to provide ways of improvement as well. However, the best method for delivering constructive feedback is a two way conversation. Two way conversations are more open, and enable each party to listen to the other’s experience and perspective. It’s amazing how two people can experience the same event in different ways.

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?

It’s a balance. Be careful to avoid overscheduling and accidentally burning each other out — not every previous in-person conversation or meeting needs to be a call.

At the same time, it is important to ensure that teams still feel connected and have face time with each other. Not every call has to be video, but in a remote world, face to face conversation is important. It’s important to prioritize time to check in and connect with each other in an attempt to foster the organic conversation and connection that occurs in person.

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?

  • Create a clear cadence of communication
  • Acknowledge checkpoints and check-ins
  • Evaluate your employees’ comfort levels
  • Foster connections and engagement
  • Celebrate all of the small wins
  • Lead by example — if you’re asking employees to be on Zoom with camera on, turn yours on first!

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.

Appreciation and critical thinking. You might be thinking that this is an unusual response however, appreciation of the moment and not taking anything for granted, combined with critical thinking and a creative approach to solving day to day and world challenges, would yield beautiful results and progress on so many fronts, don’t you think?

Also, including environmental concerns to the foundation of Maslow’s hierarchy of needs. When I think about what people need to survive; food, clothing, shelter, at risk of oversimplifying, if you translate that into a modern day, broader picture, we need economics to acquire the things we need. We also need the environment to sustain and provide us with the raw materials. These to me are the long poles in the tent.

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

At holiday meals, my grandmother always says a prayer and closes with gratitude before we eat, which I find quite relevant when adjusting to the new normal. It’s always something along the lines of, “We appreciate all of the challenges, and the path itself, as we navigate those challenges”. It’s a challenging, interesting time to be alive, yet while challenging, the path forward is new, exciting. Hopefully this experience will lend itself to rewarding personal and professional growth!


Robin Clayton of fifty-five: Five Things You Need to Know to Successfully Manage a Remote Team was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

Bobby Hershfield of VIA: Five Things You Need to Know to Successfully Manage a Remote Team

Humanity. This is the main thing you must work extra hard at with remote teams. We all know email is void of tone. Zoom and conference calls are void of interaction. It’s just a bunch of people taking turns at talking. What’s missing is that intangible quality of understanding. Of reading a room and knowing when to pivot in tone or demeanor or message. It’s also lonely since you don’t have instant feedback necessarily on what you’re saying. So, you must go above and beyond to try and stay real and honest.

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

Bobby Hershfield is currently the Chief Creative Officer of VIA, an independent, award-winning, nationally recognized agency in Portland, Maine.

He arrived from The Community, where he served as VP/Executive Creative Director and was responsible for opening the New York office of the multicultural agency headquartered in Miami, Florida. Prior to his stint at The Community, Bobby was Partner/CCO of SS+K, where he helped transform the agency culture by changing everything from the physical space to the process. As a result, he led the efforts for the high-profile Webby-winning reelection campaign for President Barack Obama and the most-awarded campaign of 2014, including The One Show Best of Show, for HBO GO. Other projects included corporate reputation campaigns for Wells Fargo, Delta Air Lines, Planned Parenthood and the NCAA.

Previously he spent five years at Mother, where he went from Copywriter to Executive Creative Director and worked on the Target Kaleidoscope Fashion Spectacular, named by TED as “one of the 10 ads worth spreading”; Target’s Missoni effort, “Little Marina,” named The One Show Best in Show; a 2008 CNN election ad for President Barack Obama, read live on-air the day of the election; and the relaunch of K-Y, which led to an increase in sales of e.p.t. pregnancy tests.

Bobby started his career as an account person and spent eight years growing through the ranks at DDB Needham Chicago, Chiat/Day NY and eventually Wieden+Kennedy. At Wieden+Kennedy, he spent five years between Portland and running a one-person office in Australia, eventually becoming Management Supervisor/Head of New Business at Wieden+Kennedy New York. And it was in New York that he took an obscene pay cut, put his job on the line, and switched from the client side to Junior Copywriter. In five years as a Copywriter, he developed work for Jordan Brand, ESPN, and the launch of ESPNU and developed the Beta-7 campaign for SEGA, which Ad Age named in the Top 10 Campaigns of the Decade, before moving to Ogilvy to work on a global, ongoing mid-market campaign for IBM and a relaunch of Yahoo.

He has been named one of the Top 50 Creatives by Advertising Age, and his work has been recognized by Cannes, The One Show, the ANDYs, Art Directors Club, Webby, CA and TED. He has been a guest speaker at Cannes; taught classes at Duke, VCU and University of Hartford; and been published in McSweeney’s and Ad Age. A graduate of the University of Michigan, Bobby has written two unpublished novels and moonlighted as a stand-up comic for two years. He’s currently taking banjo lessons.

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 was born in Akron, Ohio and lived there until I was 8. I then moved to Miami Beach, Florida, for the remainder of elementary school. And when I was 12, I moved to West Hartford, Connecticut. I bring this up because they are three very different parts of the country and I moved at very transformative ages where you feel somewhat established but are still figuring out who you are as a person. And at the time it might’ve felt weird and unsettling but now it feels like this is how it was supposed to be. This is who I am and I’m equal parts all those places and experiences.

My mom is a fine artist and writer and my dad is a chemical engineer. They divorced when I was 7 but I always said my family as a divorced family was closer than many families whose parents stayed together. I feel a deep connection with both my parents and Advertising felt like a way to put both of their talents to work. The rationale problem solving with the blank canvas of creativity. I went back to the Midwest for college at The University of Michigan and I got my first full-time job at DDB Needham in Chicago during my senior year. I got laid off exactly one year to the day of my start date. I cried. And then worked in a video store for six months before selling everything and moving to NY. I had one year of Account Management experience and I remember I wrote my introduction and read it on cold calls to different HR people all over the City. I got so fed up with the rejections that when I called Eve Luppert at Chiat/Day I threw away the written and rehearsed introduction and just said, “Do you need an account person or what?” Somehow that worked. I went in for the interview, got the job 48 hours later and treated myself to McDonald’s which I promised to give up until I had a job offer. But my career took off from there. Chiat turned to Wieden + Kennedy for 10 years then Ogilvy then Mother for 5 years, SSK for 5 years, The Community and now I’m CCO at VIA.

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

Easily going from Management Supervisor to Jr. Copywriter. I was just about 9 years into my job as an account person where I just had enough. I had moved up to a position that was further away from the work and I didn’t particularly enjoy it. I remember I applied to the Peace Corps because I knew I was done and was exploring other opportunities. I also started stand-up comedy and performed for a couple of years. But, during the 2000 World Series when the Yankees were playing the Mets I was working at WKNY and I wrote headlines for an existing campaign because we were so short staffed. They got produced and I loved seeing my lines in the paper and on buildings and around the City. I went to Ty Montague and Amy Nicholson and expressed my desire to move into the creative department. Dan Wieden was against it and in some ways I totally understood. The idea that you don’t just “become” creative. You either are or you aren’t. But I knew I was, and I felt like momentum just kept me in the wrong job for so many years. So, I negotiated a deal that I would go to night school to get a book together, work on current clients and take a 60% pay cut. And I accepted that in six months if they didn’t like my work I would be fired. After six months I flew to Portland to present my work to Dan and after looking at it, he opened his arms wide and gave me a big hug. Again, I cried and treated myself to McDonald’s.

But the entire experience was so humbling since I used to lead an account and now, I was starting over and the people I used to manage were managing me. And I was writing radio, internal videos and case studies. And I was broke. I had to change my entire lifestyle to accommodate the significant drop in pay. One of the best moves I ever made but it was certainly hard.

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?

I feel like my career is a list of funny mistakes and anyone who knows me is sure to remind me of them but here are three.

  1. As an intern in the media research department at J. Walter Thompson London, I calculated all the dollars to pounds incorrectly and my entire intern project was wrong.
  2. I was handpicked to go to the Nike Sales Meeting and travel with Jim Ward who was the then account director and I left the work we were presenting on the airplane.
  3. I was so frustrated on a client meeting that I asked if anyone had a match so I could light myself on fire not realizing I wasn’t on mute when I said that.

What advice would you give to other C-Suite executives to help their employees to thrive and avoid burnout?

Never forget what how it felt to be an employee. I was promoted later in life, well into my forties so I was on the employee side of the Agency meeting for a long time. It’s still fresh in my mind and I think that helps me in my role today. It’s understanding. Remember how you felt working so many hours or days in a row. Remember how you felt not hearing some positive reinforcement. Also, remember your worst boss and just do the opposite. Oh, and most importantly, make it about the work and not you. It’s about their success, not yours.

Just do what’s right and put other people first. If someone needs a break, give them a break. It seems so obvious but just ask how someone is doing. Be aware of workloads and manage accordingly. Just act humanly.

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?

I have a few experiences. I was a one-person office in Melbourne Australia handling the 2000 Olympics for Nike. The entire team was in Portland, Oregon, and I had to organize all our efforts from afar against time zones and distance.

I was the writer on an IBM mid-market campaign that went global and I was working out of NY but with teams in Asia and Europe to adapt my campaign in their regions.

And most recently, I helped the community, based in Miami, open their New York office and I was overseeing teams in New York and Miami.

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. Humanity. This is the main thing you must work extra hard at with remote teams. We all know email is void of tone. Zoom and conference calls are void of interaction. It’s just a bunch of people taking turns at talking. What’s missing is that intangible quality of understanding. Of reading a room and knowing when to pivot in tone or demeanor or message. It’s also lonely since you don’t have instant feedback necessarily on what you’re saying. So, you must go above and beyond to try and stay real and honest.
  2. Spontaneity. It’s just gone. The hallway chats. The office or cube pop-ins. Everything is scheduled and organized and that makes it hard to get into a workflow. To see an exchange of ideas and build on what people are doing. Also, just to get temperature checks on how people are feeling. It’s a lot different stopping by a person’s office and saying hello than scheduling a meeting to say hello.
  3. Trust. If you’re a control freak, remote working is tough because it’s simply too hard to gauge what’s happening once you end the call. There’s no single place where you can check-in or gather. So, you just must let go and trust that people are doing what they’re supposed to and have the same interest at heart.
  4. Which brings me to culture. Culture is harder to maintain. When you’re in a culture where the work is the priority it’s easy to prevent other agendas from seeping into that culture. If you’re agenda is different from the groups, you stand out. But when you’re not in that place where the culture is so present then you’re now free to craft your own culture. The single unifying mission is diluted. And people have the space to interpret and rethink and invent their own mythology to things that can easily be explained if you’re all in the same room. So, you must work harder to remove the distractions that can poke at that culture.
  5. Breaking habits. I think in some ways being forced to work remotely has been good in the sense that we were becoming robots. Work, meetings, work, late nights just become the way it was. Everyone striving to find a work/life balance. Even talking about a work/life balance. And now we’re seeing the other side. And yet, I work from home and there could be a day that goes by where I don’t have time to walk to my kitchen and get lunch. That almost becomes more frustrating because I’m at home. I should be able to go to my kitchen and yet I can’t. I think this idea of staying objective and not falling too fast into a routine is a good lesson. Trying to have that work/life balance while still feeling you’re giving everything to your job and your life so that both parts of you can feel fulfilled.

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

Some of it is just acceptance. It’s the way it is and try not to get discouraged or get too hard on yourself. Spontaneously check in with people. Go to a social distance lunch. Trust people. Judge people on their work, not their time. Who cares if someone isn’t doing it the way you would, or would want them to? If the work is good, the work is good. Let process go a bit and let outcome be the thing on which people are judged. And to people that have been doing this awhile appreciate you get to learn something new again. It keeps you young and energized that it’s not so predictable. Not so rote. There are new ways to manage and new ways to lead and that’s exciting. Finally, have a sense of humor about it. One of the rules in standup is that if something happens in the audience, you must acknowledge it in your routine. The audience needs to feel you’re with them, seeing what they’re seeing, hearing what they’re hearing. If a kid bursts into a zoom call, acknowledge it. Make a joke. Have fun. Try not to be so rigid that you can’t allow for interruptions and normal mistakes to creep in.

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

I believe you just do it. But that’s who I am. If I try to couch something in a positive opening, I come across disingenuous and I just can’t do it. When people do that, I always feel they are reciting from a management manual. I remember when I was starting out at Chiat, we weren’t allowed to say “but” when we gave feedback. Creatives hated hearing positives because they knew whatever came after the “but” was the real feedback. I guess that always stood with me. Just say it. But then listen. Allow people to vent, swear, whine, complain whatever they need to do. Help them solve the problem. Your job isn’t done just because you transferred the feedback onto them. Help them digest and come to a solution.

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

It’s funny, I’m used to just starting an email with what I’m going to say. I guess at Mother and Wieden, we just sort of launched into the email. Sometimes even in the subject line. At the community, every email started with a salutation. Saying the person’s name. Saying “hello”. It made me slow down a bit and gather my thoughts and it felt a bit more civilized. I think there’s a greater lesson there. Slow down. Don’t just write the email to get your thoughts forward. Remember the person reading the email. How do they take bad news? How do they take criticism? Sometimes you can’t avoid it. Feedback is feedback. Criticism in criticism. Let it be so. But try to make the reader feel that you know what it’s like to read this type of email. Offer to call them to discuss. At Wieden we said, emails never initiate feedback. They follow up. So maybe start with a call and use email to get it in writing. Doesn’t hurt to call the person after as well just to allow that person to voice their response.

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?

Allow me a bit of a digression. When the TV series, “The Office” came to America I seem to remember a story where after the first season, Ricky Gervais called the creators of the American version and told them to not just copy the British episodes which they did in the beginning. He gave them freedom to use the British series as a framework rather than something to copy..And the show got better with each season. At least I think I remember reading that. But my point is don’t try to recreate the work environment remotely. Have zoom meetings. Have phone calls. Allow people time to work and do whatever. But try not to hold people to when to start the day, when to eat, when to take breaks and when to stop. Make the work the goal not the process. Maybe have company meetings every other week. I’ve admired the way VIA has worked together in this time. We started with Management meetings twice a week on a Monday and Friday. Now they’re once a week. We have department meetings every other week. We used to have happy hours and morning coffee together but now we don’t really do that anymore. We have agency meetings to bring people together but also to disseminate information and keep people informed of our progress as an agency and updates on clients and work. It’s a nice balance of leaving people to work as they work and still allowing them to feel part of a company.

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?

Check ins and keep hammering home what that culture is. Repeat and live by it. Don’t just assume the culture stays with people when they’re not working in the office. And it’s what I said upfront. Empathy and understanding. People who have kids don’t necessarily have it harder than someone who is single. People have their own neurosis and ways of coping and reacting to this situation. Everyone requires a bit of an individual approach to management. It can’t just be a blanket way of running an agency. Everyone is dealing with this differently. So, abandon judgement on everything but the work. Keep it about the work. Remind people of why they work for you. What they signed up for. Make sure your vision for the company is reinforced because it won’t be readily apparent when the news of the day, family and other distractions take over. So just do things to remind people what kind of company you have and what kind of leader you are. Don’t stop just because you’re not together. In fact, you almost must work harder at it.

The other suggestion is perspective. It’s grim out there right now. And it’s easy to fall into a rut or complain. Try, in some way, to feel fortunate. You have a job. You have a schedule. Direction. I think perspective sometimes gets lost in all of this. It doesn’t give people license to take advantage, but it should resonate with people that if you have a job right now, you are one of the lucky ones and it should help people band together and focus on a singular mission.

If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

That’s hard because there are just so many things wrong right now. We need so much help. But I guess I would say I would inspire a movement to get rid of social media. Put it back in the box. I am starting to believe the cons are outweighing the pros. The good is that I am connected to so many people I’ve lost touch with. I can see my friend’s kids grow up and I can experience their happy moments even if I’m not there. And I get a ton of Happy Birthday wishes. But the bad seems so so bad. The siloed groups we’ve now live in. The echo chambers we scream into. The bullying. The FOMO. The judgement. The microscope we all live in. The need to be something or say something you may not want to be or say. It’s dangerous. We were supposed to come together but instead it pulled us apart. And we use it to pounce. We use it to pile on. And clearly it can be manipulated to disseminate false information and even worse infiltrate our private life or affect our way of thinking. So, for me, I’ll go without the birthday messages because I really think the harmful effects are creeping into our daily lives and lying just under the surface of photos and posts and updates. The good can be replicated. I’m sure of that. I just am saddened and disheartened by the bigger negative picture.

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

One of my favorite quotes comes from Robert Browning, “A man’s reach should exceed his grasp, Or what’s a heaven for.” And I know it’s about overachieving and taking on the seemingly impossible, but I also allow it to mean something else. When I was a swimmer in high school I was supposed to swim the breaststroke. But after getting beaten by a teammate during a meet, I was giving a choice between butterfly and backstroke. I went to my friend’s father who was a swim coach for another team and asked which stroke I should choose, and he said, what do you feel the least comfortable doing and I said butterfly. So, he said I should do that. I spent the next four years swimming butterfly. I love that story and always think about it. Because we often shy away from what makes us uncomfortable and the idea of going head on provides the most rewards. And sorry to go back to this, but social media allows us to live comfortably solely in our worlds. And what we need to do is allow ourselves to grow into new situations and scenarios. Kind of like remote working. Grow into that and accept that it’s uncomfortable at first but then figure out how to perform the best we can. So, I’ve always tried to put myself in uncomfortable positions and that way I grow to the situation. Kind of like going on stage for the first time. Or trying to lead a creative pitch remotely. It forces me not to settle and It pushes me forward. And quite often the experience and the results are quite rewarding. And that is a heck of lot better than using McDonald’s as an incentive. That I’m sure of.


Bobby Hershfield of VIA: Five Things You Need to Know to Successfully Manage a Remote Team was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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

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!


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.

Cathryn Lavery of BestSelf Co: Five Things You Need To Know To Successfully Manage a Remote Team

Cathryn Lavery of BestSelf Co: Five Things You Need To Know To Successfully Manage a Remote Team

No water cooler moments — remote workers can’t pop into someone’s cubicle for a quick catch up and as a leader, you can’t keep pace on what’s happening in your company through office eavesdropping. Instead, it would help if you were more intentional with your communication.

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

Cathryn Lavery is an entrepreneur and creator. As co-founder and CEO of BestSelf Co., Cathryn helped take the company from zero to 8-figures in less than two years. BestSelf Co. won Shopify’s Build a Business Competition in 2016 and the Build a BIGGER Business competition in 2017 — making BestSelfCo. the only company to win both awards consecutively.

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 Northern Ireland and went to university in England and Scotland, where I trained to become an architect. After graduating in 2011, I secured my dream job as an architect in New York City. I was super excited to emigrate to the US and start a new life. But things didn’t work out as planned!

I’d already interned for the company I was moving to New York City for. They knew my work and I’d accepted a salary of $40,000. A couple of months before moving over, I got an email to say my pay was being cut by 25% to $30,000 because there wasn’t enough work. It was a blow, but I was reassured by their promise to increase my salary once the workload increased. But that wasn’t the only goal post to move…

I arrived in the US with just a few hundred dollars to my name and two weeks to find my feet before starting my job. But one week in, my new employer rang with the news that they still didn’t have enough work for me. They were pushing my start date back a further six weeks. It was at that point I realized that I couldn’t trust a job to look out for me.

So, to help me get through those first six weeks with no income, I started to hustle and do things on the side. I launched my first Shopify store and continued working on it alongside my architecture job after I started. About two years in, I realized architecture wasn’t for me. Besides, my Shopify store was generating more income than my paid job — and I was only putting a couple of hours into it each week.

At that point, I quit my job to become a full-time entrepreneur and I’ve not looked back.

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

Winning Shopify’s Build a Business competition and then the Build a BIGGER Business competition in two consecutive years — the only company to have done so. It was an incredible experience that opened so many doors and connected me to some incredible people. In fact, the competition was one of the reasons I set up a Shopify store in the first place! I was attracted to the incredible prize, which was something money can’t buy.

I first entered in 2012 and came nowhere near to winning, but that only made me hungrier. I decided to enter again with BestSelf Co. in 2016. I set a goal, figured out what I needed to do, and got my head down. It’s all about persistence.

The win gave me some of the best experiences of my life as well as opening doors that wouldn’t have been possible otherwise. For example, I ended up playing Monopoly with Daymond John for over 6 hours. We played until 2 am while staying at the Great Gatsby mansion. I found out later that Daymond uses Monopoly as a way to test people. It turns out that Monopoly is very revealing. It shows you how people make decisions, strategize, and use money. You can also see how people play and whether they’re willing to cheat! Daymond liked the way I played, and this transformed into a deal where he endorsed the Self Journal and gave it out to everyone in his co-working space.

This story is a reminder that it’s how you cope with rejection that matters.

I didn’t win in 2012, but I didn’t give up either. I’ve learned that sometimes rejection is the best thing that can happen to you because of what it inspires you to do afterwards. I’ve learned to not believe in regrets. Regrets are all about the timeline. In the thick of it, things may feel terrible and upsetting, but as you zoom out, you often see the ‘failure’ ended up serving you in ways you couldn’t have expected.

In other words, focus on the timescale and not the problem to find the silver lining.

Not all gifts come wrapped. Some gifts are tough to swallow at the moment; it’s only later — after time has passed — that we realize how incredible they actually were.

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?

There was a time when I went to the wrong job interview and ended up getting the job!

As part of becoming an architect, I needed to spend a year in an office. To increase my chances, I secured six interviews with different firms on the same day. I had two in a row and the first company kept me longer; joking that they were doing it because they wanted to hire me! It meant I was in a rush to get to the next interview. And that’s when the mistake happened…

There are two firms in Belfast with very similar names. I ended up going to the wrong one.

When I walked into the office and announced that I was here for my interview, they said they had nothing scheduled. They assumed it was their fault so they looked through my portfolio and interviewed me anyway.

30 minutes later they offered me a job.

I didn’t realize my mistake until I got an email from the company I was supposed to interview with. They wanted to know where I was!

This experience taught me that if you’re confident in yourself, you can still win — even if you make a mistake.

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

I was pretty close to burnout at uni.

I worked all the time and barely slept. Back then, long hours felt like a badge of honor. I thought I had to put in the hours to be successful, but it wasn’t healthy.

One of the best ways I’ve found to avoid burnout is to understand when you do your best work. It’s not about the number of hours you work, but how productive you can be in the time that you do. There’s little point sitting at a desk when you feel uninspired and exhausted. Better to take a break and come back when you’re feeling motivated.

And anyway, we vastly underestimate the value of ‘down’ time.

Taking time out gives your brain the space it needs to strategize and think about things at deeper levels. I’ve come up with some of my best product ideas when I’ve not been trying. Without space to think, we default to action, which means we’re focused on doing stuff and checking tasks off. Thinking time creates opportunities to mull over the bigger picture — which often morphs into the birthplace of brilliant ideas.

Other strategies include prioritization — following the 80/20 rule — so you can identify the levers that when pulled make the most significant impact.

Another strategy I swear by is to distil your goals into habits. Figure out what steps you need to take every day to move the needle consistently in the direction you want to go. You’ll be surprised how much you can achieve when you take baby steps consistently.

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?

Five years — BestSelf Co. has always been an online, remote company.

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. No water cooler moments — remote workers can’t pop into someone’s cubicle for a quick catch up and as a leader, you can’t keep pace on what’s happening in your company through office eavesdropping. Instead, it would help if you were more intentional with your communication.
  2. Lost in translation — when you’re not face-to-face or in-person with people, it’s harder to understand the nuance of what you’re saying or your tone. In the past, I’d invite my team to hop on for a one-to-one because I wanted a catch-up, they’d interpret the ‘let’s talk’ as an indication they’d done something wrong!
  3. Not brainstorming in the same room — there’s a certain vibe you get from being in the same space as someone else who’s working on the same thing. It’s not impossible to do this remotely, but it’s harder.
  4. Lack of connection between co-workers who’ve never met. It can be a challenge to create a close team community when team members haven’t met in real life.
  5. Worry that your workers are doing what they should be doing? When the pandemic first hit, we ran an online summit sharing insights about effective remote working. One of the questions that kept popping up was how do you know if your team is working if they’re not in the same space as you? Here’s my answer to this… if you don’t know what your people are doing because they’re not sat in front of you, you’ve got a bigger problem! Physical presence at a desk is not an indication of output. Results are.

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

  1. Introduce intentional communication strategies. For example:
  2. Team chat channel on Slack so there’s space for your team to socialize with each other
  3. Use GIFs — they’re vastly underrated as a way to communicate and connect
  4. Hold in-person retreats — we do these twice a year because they help strengthen team bonds and relationships
  5. You can stop things being lost in translation by getting on a Zoom call [so you can see each other’s facial expressions] or by recording audio notes [so your tone of voice is clear].
  6. We have in-person team retreats twice a year where we factor in time for brainstorming and collaboration. We have regular online working sessions and if the need is sufficient, I’d arrange an in-person working session and fly in the key people involved.
  7. We ensure Slack conversations and team meetings aren’t 100% work-related. Having space to socialize is critical. We do a Secret Santa each year with an online opening of gifts on Zoom. We’ve even played games on a Zoom call! There are plenty of ways to create a strong culture and feeling of connection. You just have to be creative.
  8. I’m interested in the output my team creates — NOT the hours they work. I don’t need to have my team in the same room to know that they’re working, I just have to look at how the needle is moving on the business. Everyone on the team has targets connected to the bigger business goals. This is all the visibility I need to see how effective my team is. Another way to ensure your team delivers is to hire the right people. Remote workers need to be self-motivated and be able to use their initiative. I look for people who don’t need endless handholding.

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?

As a leader, you need to master the art of giving feedback to your remote team. You can let things sit, or they fester. With a remote team, you don’t have the luxury of being able to pop into someone’s cubicle or ask them to come to the office to see you! Instead, you have to rely on the tools available.

Constructive criticism by text, Slack, or an email can come off as too harsh.

I recommend getting on a zoom call and giving feedback that way so the individual can pick up on the nuances and your tone. If it’s not possible to get on a Zoom call, I’d record a Loom video so they can see your facial expressions and hear your tone of voice on their screen.

Another alternative is the ‘record’ app in Slack, which you can use to record your voice while giving feedback.

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

I wouldn’t recommend giving feedback over email because it’s too hard to communicate your intended nuances and tone. Instead, I’d recommend recording a Loom video of your screen as you walk through your feedback. Not only is this option a lot quicker, but it also prevents things being lost in translation.

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?

One of the most important things is to leave time and create space for teams to keep being social with each other. If people are used to an office environment, they may find remote working more isolating. There is no physical water cooler where people can have a conversation and catch up. There are ways to create a similar experience online. For example, you can create a team chat channel on Slack for chit-chat conversations and connection. We also have weekly calls to talk about our weekend plans.

One of the biggest obstacles is adjusting to working from home. You’re going to encounter new distractions — especially if you’re homeschooling children. Expectations need to change with remote working. Your team may not work the same hours as they would in the office, but that can be a good thing. Not everyone is at their peak between 9–5. Remote working can create flexibility for people to discover when they work best.

Remember, you don’t measure productivity by hours active on Slack. You measure it by the results your team achieves and the work they get done.

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?

Everyone on the team must be committed to the mission of the company. We’re all united around a common WHY. Everyone feels called to step up and do what’s right by the business and our customers because of a shared value we call Absolute Ownership.

It’s essential team members feel purposeful in their work too. Everyone’s work is important and necessary. No one should feel like a number because everyone is a vital cog in the BestSelf Co. machine — all pulling together to do show up in the best way we can. This desire to impact is baked into everything we do — from the way we serve our community, to how we create products based on customer needs, to our internal Slack channel where we showcase and celebrate customer success stories.

I’ve said it already, but building a connected culture is also important. BestSelf Co. feels more like a family because everyone cares for and looks out for each other. Everyone is willing to step in to help where needed because we all care about winning.

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 want to inspire people to invest in personal development so they can become their best self — not just for personal gain, but because of the ripple effect it has on everyone around you.

Your best self is personal… it’s whatever it means to you.

But when you improve yourself, other people see it — and that transformation inspires others to seek out the best version of themselves too. You shouldn’t stop learning just because you left school. Learning needs to be a lifelong commitment. Self-education is that tool, which empowers you to keep growing, expand your comfort zone, and raise the standards and aspirations you have for your life.

Best of all, you never know the impact your personal ripples make as you become a better person.

Looking back, if I hadn’t committed to personal development when I did, there would be no BestSelf Co. In turn, we wouldn’t have impacted the people we have — both our customers and the team. My life would be radically different too. For example, I’d probably still be working in a job and industry that wasn’t for me.

Personal development and a desire to be your best self opens a door for a more successful and fulfilling life. It’s why I’m passionate about creating products, tools, and resources that can guide people along that path.

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

“Not getting what you want either means you don’t want it enough, or you have been dealing too long with the price you have to pay.”— Rudyard Kipling

For me, this quote captures the idea that you can get anything you want if you’re willing to commit to it and work for it. This quote reminds me that I have control over my life and my results are down to me.

A lot of the time, people fall short of where they want to go because they stop too soon. They want something big, but don’t take the right daily actions, which means they don’t see sufficient progress so get disillusioned and disinterested.

This quote is a reminder that you have to do the boring stuff too. It’s a reminder to stick to your habits instead of constantly switching up or trying something new. Taking the right actions over a long period of time is what gets results because that’s when the compounding effect kicks in.

Thank you for these great insights!


Cathryn Lavery of BestSelf Co: Five Things You Need To Know To Successfully Manage a Remote Team was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

Kevin Torf of T2 Tech Group: Five Things You Need To Know To Successfully Manage a Remote Team

I have been working for clients all over the world and have needed to perform many of my duties remotely. One of the companies I founded 30 years ago, Torsys, employed people from all over the United Sates and at that time, I learned different ways to communicate with these employees. I have also been very fortunate with T2 Tech Group being able to provide custom technology, support and solutions over the last decade to help our customers build their infrastructure to support remote employees.

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

Kevin Torf, co-founder and managing partner of T2 Tech Group, has been a renowned innovator and thought leader in the technology industry for over 35 years, specializing in large-scale IT strategic planning, project design and implementation. Kevin also brings decades of experience in complex application deployment, IT architecture, electrical engineering and data center construction, infrastructure and consolidation and more, particularly within the healthcare space.

Predominantly self-taught, Kevin is an autodidact who discovered his love for technology at a young age, soaking up information from his father’s knowledge of electronics and programming. After starting his professional career in technology purchasing decisions, he merged his love for tech with his passion for entrepreneurship and founded a series of extremely successful companies — Torsys, a consulting company focused on managing large scale technical projects for companies including Microsoft, AT&T and Starwood ; Tornado Development, which became a multi-national leader in developing the first unified communication platform offered to the largest carriers around the world; Inuntius, where Torf developed one of the world’s first digital phone services over the internet VoIP (Voice over Internet Protocol); and Intelliverse, where he led the optimization of a single technology platform consolidating voice, email and fax, now utilized by millions of companies worldwide.

After founding T2 Tech Group, Kevin conceptualized and designed the company’s unique project management approach never before seen in the tech industry: the hybrid-Agile methodology, blending management techniques used to optimize client planning. Through this approach, T2 Tech’s partners have experienced remarkable results — saving millions of dollars in vendor management, improving application performance by as much as 400 percent and achieving an unequivocal scalable IT environment optimized for success.

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 discovered my love for technology at a young age, soaking up information from my father’s knowledge of electronics and programming. I began my career in technology writing programs for extra pocket money at the age of 14 and eventually merged my love for tech with my passion for entrepreneurship and founded a series of companies. I co-founded T2 Tech Group in 2006 and designed our company’s unique project management approach: the hybrid-Agile methodology, blending management techniques used to optimize client planning. Now, I have over 35 years of experience in the industry, specializing in large-scale IT strategic planning, project design and implementation.

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

I have so many, but my proudest moments have been foreseeing a need that technology can solve. Most of the companies I founded all started with solving a problem I had in my personal or business life. Forty years ago, at the age of 18 I needed a way to remember the videos and movies I rented from a local video store, so I did not get the same video again. I developed a program to keep a record of what I had seen, as well as categorize what I liked, and compared that to what was available in the video store. From that idea I started my first company called Compu Video.

Twenty-five years ago, I was trying to find ways to better communicate with my staff that were all over the country and started developing tools to help facilitate that need. The tools I developed led to the formation of a new company called Tornado Development. Tornado Development was a pioneer in digital communications.

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?

Some of the funniest moments have been intertwined with all of the people I have met over the years and moments that have been captured in an instance of time. The greatest lesson I’ve learned was when I came to the United States and first had M&M’s chocolate candies, which I did not like. I had grown up eating Smarties, which is a similar candy from South Africa. Over the thirty years I have been in the United States, and still today, when family members visit me from South Africa, they bring me a box of Smarties. One afternoon, I was reading a magazine about an American that had migrated to South Africa and their only complaint with the country was that the Smarties were terrible, and he could not wait to have his family send him M&M’s. I learned that day that no country or person is better than the other, but just different based on what we as individuals have grown up to appreciate. I would say it was the greatest lesson I’ve learned and gave me a new perspective.

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

Technology is a grueling industry and requires countless hours to build and support the ever-changing landscape for companies’ use and needs in their day-to-day lives. Organizations cannot afford any disruptions or downtime for its employees due to changes. So, updates and improvements to the numerous types of technology systems are done in the evening and weekends making some of your work hours long and tiresome.

The secret is all about enjoying what you do. This is sometimes less about the person or company you work for — although they can play a major role — but more about yourself. I have always enjoyed being challenged and wanting to learn how technology worked. That passion never made my work feel like a chore. What CEOs and CIOs need to provide is an environment where individuals like myself can engage in these passions and feel like their efforts can make a difference, regardless how small they may be. This may not be the ideal work environment for everybody, but the people it does work for will very seldom get tired.

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?

I have been working for clients all over the world and have needed to perform many of my duties remotely. One of the companies I founded 30 years ago, Torsys, employed people from all over the United Sates and at that time, I learned different ways to communicate with these employees. I have also been very fortunate with T2 Tech Group being able to provide custom technology, support and solutions over the last decade to help our customers build their infrastructure to support remote employees.

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?

‘Out of sight, out of mind,’ the oldest saying in history is very true. As managers, we have been taught that management is about monitoring and policing a person’s behavior and productivity. Although this concept is evolving and organizations have started to manage employees based on outcomes, this has become more important as employees are now working remotely and management, in some cases, has lost visibility of how an employee behaves.

Challenges

How do you know a person is actually working and not watching TV? The question is: do you need to know? If the person is doing their job and their performance levels meets the organizations benchmark, should that not be acceptable? The challenge is most organizations do not know how to measure outcomes or what is acceptable. Use and build tools to help measure and monitor outcomes.

Isolation of employees. Most people like to be around other people and have the ability to socialize. Working remotely will isolate a person and they can feel that they do not have the support of their management or peers, or an outlet to communicate their problems or share their family and personal stories. Organizations need to change the way they encourage employees to reach out to one another to get support and interact with each other creating a greater level of collaboration.

Measuring performance. Measuring a person’s performance can start to feel like “Big Brother” and create a stressed relationship with the employee and management. Instead of measuring an individual, work on measuring a team’s performance where possible. Try creating a competitive environment around team performance. This will have the team work closer together and engage with each other, while creating a self-sufficient model reducing or even eliminating the need for a supervisor or manager.

The wrong Tools and Technology. Having the wrong computer or internet access can impact a person’s ability to be productive or have good quality calls. Establish a standard to perform the job function and provide aid and assistance to your employees that do not have these tools or internet. The cost to purchase a new computer, upgrade the internet or provide a work desk is small considering the savings of not having them come back to the office and reducing the real estate and utilities cost.

Separate work and home life. It’s hard when you have the family all working together in the same room and confined indoors to distinguish the difference between being relaxed at home versus what you were used to at the office. This is also not healthy as work and home become one in the same. I recommend dressing to go to work. The idea of dressing in work attire while at home might seem unnecessary but it creates a subconscious difference and the people around you will treat you a little differently. Then, when you change clothes at the end of the day, you are now at “home”.

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

See response above.

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?

Don’t berate an employee and be selective on the words you use, employees that get offended will behave differently at home than they would in the office. In the office they might be more constrained and eventually their anger will subside. At home, that might not happen therefore escalating the problem more than is wanted or needed. Use video were ever possible so you can interact and see the person, this will have a different impact than just a phone call. Lastly, learn to use different words in how you express yourself.

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

Email can be very dangerous if used incorrectly. People tend to say things they do not realize until after the email is sent. Unless the manager is very skilled at writing, managers should be cautious of sending harsh emails without thinking through the words being used, the implications and what the objective is. I suggest always trying to call a person first and verbally discussing with them the problem and then following up with an email. This will put the email into perspective and will corroborate what you said.

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?

Continue to communicate. When we work together, or are in close proximity to each other, you tend to talk more, joke, make comments and interact sometimes for no reason other than to break up your day. Being remote takes that all away. Learning to use a messaging product and chatting with your team even for non-business reasons can help. There are some private social media portals where the team can share information with each other that is restricted only to the team, not the public. They have the ability to have real-time video that is on all the time running in the background. Although that can be a little distracting, these are creative and different ways to fill a gap that is hard to replace.

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?

Empower the team. Create a working environment where the team has no choice but to reach out to each other in order to get their job done. Not all jobs will provide that capability, but with a little restructuring this can be done more so than initially thought. By having the team work together and make decisions together, it will make them more accountable and that is what empowerment is all about.

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. 🙂

Allow people the opportunity to be heard, lead people and don’t judge, mentor versus tell, and inspire people to think for themselves. I believe every person can grow and learn if given the right opportunity. Micromanaging and dictating what needs to be done might get the job done at that moment, but people do not learn to think for themselves, only follow direction. This method stifles innovation and creativity. I would try and inspire diversity in ideas and thoughts, regardless of education, age or position. Hearing different perspectives and working to bring people together as a team is a great power I strive to obtain. Ask lots of questions and listen!

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

If you’re dropped in the middle of the ocean, what direction would you swim if you are unable to tell where land is?

The answer is not important just as long as you swim. If you don’t swim you will eventually drown. Swimming (doing something) might get you where you need to go, or you might head in the wrong direction. Either way, you’ll never know unless you start swimming. As you’re swimming, try to learn and adjust course as needed, but don’t stop.

Thank you for these great insights!


Kevin Torf of T2 Tech Group: Five Things You Need To Know To Successfully Manage a Remote Team was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.