Bobby Hershfield of VIA: “Breaking habits”

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 […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

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.

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...


Olumide Gbenro of The Digital Nomad Summit: 5 Things You Need To Know To Successfully Manage a Remote Team

by Fotis Georgiadis

Kathy Delaney of Publicis Health: “Difficulty Reading the Room”

by Fotis Georgiadis

“5 Things You Need To Know To Successfully Manage a Remote Team” With April White

by Fotis Georgiadis

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.


We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.