350: Tiffany Rolfe - "The Mom"

Tiffany Rolfe of R/GA

Where does work end and life begin?

"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT

Episode 350: Tiffany Rolfe

Here’s a question. Where does work end and life begin?

I’m Charles Day. I work with creative and innovative companies. I coach their leaders to help them succeed where leadership has its greatest impact. The intersection of strategy and humanity.

This week’s guest is Tiffany Rolfe. She’s the Global Chief Creative Officer at R/GA, a job she took on in the early stages of the pandemic as part of a new leadership team.

Two years ago, the Ad Age A List recognized R/GA as the Comeback Agency of the Year. This year, they are now ranked second among all agencies.

Tiffany’s email signature reads, Mom and Global Chief Creative Officer.

I speak for myself when I say that before we all withdrew into our homes in early 2020, I was aware only conceptually of how women who are parents juggle that with their careers.

But two years of working via Zoom has given many of us insights into people’s lives that were previously unimaginable for their candor and vulnerability.

“I can handle a lot and, I give it to work, I give it to my family, I give it to all those things but, you know, figuring out what that means as an individual. And I think, if anything, it just, you know… you're alone a lot in a room, I've worked from my closet, and I'm staring at myself on Zoom screens all day and if anything just that like, ‘Oh wow, me as a person, how do I make sure I'm taking care of myself in all this too?’”

This conversation is a living example of the challenges and gifts that have emerged from the last two years.

The line between work and home has been blurred beyond any reasonable hope of recognition. No matter how powerful a microscope you apply, it is almost impossible to see the separation any more between leader and human being.

The destruction of this separation can be liberating if you’re willing to create your own definition of the work-life balance.

If you’re not, it will be very hard as you try in vain to keep up with a dangerously out of date view of where work ends and life begins.

The day is not only for work. The day is for living.

What that means is entirely for you to decide.

Here’s Tiffany Rolfe.

Charles: (02:34)

Tiffany, welcome to Fearless. Thank you so much for coming on the show.

Tiffany Rolfe: (02:37)

Thanks for inviting me, Charles.

Charles: (02:40)

When did creativity first show up in your life? When were you first conscious of creativity playing a role in your life?

Tiffany Rolfe: (02:47)

I have some good stories probably from being a kid. I was a very entrepreneurial kid. My dad was kind of a start up guy and I— hold on. Hammie, I got to record, Bud.

Hammie: (03:01)

Right now?

Tiffany Rolfe: (03:02)

Yes, I'm recording right now.

Hammie: (03:03)

[inaudible].

Tiffany Rolfe: (03:04)

Okay?

Hammie: (03:05)

[inaudible] coming back?

Tiffany Rolfe: (03:06)

Yes, they're recording this now. All of this.

Okay, bye. Close the door please.

I know, one time we did a recording together, but we're not doing this one this time. Okay? But maybe at the very end.

Hammie: (03:18)

It would be kind of like the copy.

Tiffany Rolfe: (03:20)

Yeah, it would be the copy of what we already did. You're right. Okay, see you, Bud.

Charles: (03:24)

(laughs)

Tiffany Rolfe: (03:25)

We did. We planned one together where I had him kind of slide in, I was recreating that CNN moment. So yeah. My dad was a, what I called, a deal guy, growing up. And so I had a little bit of the entrepreneurial bug from him. And also, didn't have a lot of means growing up, so I was always kind of looking for ways to make some of my own allowance, I guess. And I had a pretty extensive, productive lemonade stand as a kid, which I created a lot of signs for. It wasn't just a one-off lemonade stand, it was like a lemonade industry in my garage. But I also realized that— I would sell candy as well, because a lot of the kids in the neighborhood weren't allowed to have a lot of candy, and my parents let me have candy. So I was sort of the candy hookup and I would, you know, for every lemonade that someone bought, I would let them get an auction ticket for a large chocolate bar.

And so I, at one point, had some kids in the neighborhood that I paid with candy to drive a wagon around the neighborhood with my lemonade stand signs. So that one was one of my businesses. So it was always this mixture of, I think, creativity and business, from a pretty young age. I also… my grandmother was an artist. She, you know, was a painter and encouraged my talents in that way. And I, one time, entered a painting contest, and won the top prize for one of my paintings. And so then I also sort of understood, the value of creativity in that way, you know? And wow, there are you can really get recognized through your art, And it can be something that gains you entry. and so I kind of I think merged a lot of that together throughout my childhood.

And, you know, in high school I was the one that always did the signs for the football games, you know, the big banners that cheerleaders and football players would run through as they came onto the field. So found it weaving into a lot of things as I grew up.

Charles: (05:43)

Your parents were really young when they had you, right? Do you think that had an impact on how you showed up in the world?

Tiffany Rolfe: (05:49)

Well, (laughs) yeah, they were young. They were 16 and 19 when they had me. Which I think was a lesson in just, how do you be kind of a pretty independent kid? Which first started, I think, as feeling a little bit like an only child because my brother… you know, because they were so young, my brother was born six years later. So there was, I think, a big period of time where I was like an only child. You know, my parents were still pretty young themselves, figuring out their lives, so there was a lot of me entertaining myself, I would say, and figuring out how to keep myself busy. The latchkey kid that came home from school by myself and just, am like, "Okay, now what do I do?" and so I think being bored is one way to create, to spark creativity. Not having a sibling, you figure out how to make yourself laugh. And then also, I think them being younger, there was a lot of responsibility and, you know, a little bit more growing up that I think you tend to do, as well.

So I definitely became kind of a pretty responsible kid from a young age, and rebelled against them being kind of young and having fun. I looked at my parents who were a little bit what I thought was too crazy and not- not parent enough. And that made me be very… you know, I studied a lot on my own, I was always making sure I had straight As. So my form of rebellion was doing really well in school .

Charles: (07:25)

So you were grading the parents in fact?

Tiffany Rolfe: (07:27)

Yeah, a little bit. I was, you know, judging their homework a bit more. I think at one point, yeah, my mom was kind of starting college while I was starting grade school, so we were students together.

Charles: (07:41)

And that independent streak showed up really early, didn't it? Because you moved away from home when you were pretty young. You moved to California pretty early on?

Tiffany Rolfe: (07:48)

Yeah. Part of it was maybe independence and part of it was escape from being in the middle of the country. I grew up in Oklahoma, some smaller towns in Oklahoma like Muskogee, born in Vinita, the place where there's the state mental institution and it was the home of the world's largest McDonald's, which I always said was kind of that perfect intersection for advertising, you know, the insanity and commercialism at once. And then, you know, grew up but mostly in Tulsa. We moved a little bit. I got a taste of going to other places and living elsewhere and meeting new people. So we would move away for six months and live in Portland and then we would always end up back in Oklahoma. We went to Joplin, Missouri for a couple months and we ended up back in Oklahoma. And so we were rooted there. But I knew pretty early on that I was going to leave the moment I could. I was like, "This place, I don't think, is where I'm supposed to be.” Always felt a little bit out of place growing up there.

And so pretty much the day I graduated high school, I loaded up my car and moved to Beverly, the hillbillies. Packed it up and went to California with, I think, hopes and dreams of making it big, you know, being a famous movie star or something like that. Which I pursued for maybe a few months and then realized how awful the industry was and then quickly pivoted.

Charles: (09:18)

And what got you into advertising?

Tiffany Rolfe: (09:21)

I didn't first get into advertising but I got into the web boom, dot com, you know, mid '90s. My neighbor at the time was a graduate of MIT, starting a web company. So I ended up getting kind of a part time job working for him, doing kind of office oriented stuff, buying equipment. I learned a little bit more then about having a high speed internet connection at the time when everyone was on dial ups, it was a T1 line and they were doing web design for the movie industry. And I had that hope to connect into the movie industry in some way. But this was a different way in and started to teach myself and learn about design through websites, which was very, very early on, when not many people even knew what that was. And going in and marketing through that lens is what introduced me to advertising.

And the reason I ended up going back into school for advertising was merely because they didn't have any web design, you know, interactive type design programs at the time. And when I went and looked at a lot of the different opportunities and classes, advertising was interesting to me, in that you could combine creative thinking, entrepreneurial thinking, cutting back to my, you know, lemonade stand days. A little bit of everything, rather than just going deep into one skillset. It really takes a lot of different types of thinking, creative and strategic thinking and business thinking, and I thought there was something really interesting just about what I like doing and understanding that the advertising space…. And it had never really been anything I knew about, I didn't even really know there were careers in advertising growing up in Oklahoma. It wasn't like I grew up in New York near Madison Avenue or anything. And so I went into an advertising program just because there wasn't one that I felt fit me better than advertising.

And took an advertising at night class at first, and built a portfolio in that class session, and really took to it. I really understood it and got it and understood what it meant to find ideas for brands, and just found that maybe this was my calling. And then from there, after that night class, decided to enroll in the advertising program at Arts Center in Pasadena.

Charles: (11:57)

And that took you to where? What was your first job in the industry?

Tiffany Rolfe: (12:01)

Well, I had been doing startups and web design kind of simultaneously, so my first job wasn't really in advertising. It was, you know, doing marketing through these web companies, even doing marketing for big entertainment companies like Disney and Pixar. And I built a website for Bug's Life, presented it to Steve Jobs when I was only 19 years old which is a pretty humbling experience when you're that age. And then took that type of thinking, plus my advertising portfolio that I had gotten, and ended up discovering Crispin Porter Bogusky out of Miami. And it was maybe about 80 people, maybe 100 people when I was school. It was starting to show up in awards, annuals and things like that.

And, also I knew some of the other big ones, you know, like Wieden. But there was something interesting about what Crispin was doing that felt a little bit fresh. There was… guerilla advertising was a thing at the time. No one talks about guerrilla but really it was more viral, you know, activations and stunts and things like that. And they were doing some really just interesting work and starting to get some new clients, at the time. And I ended up getting a connection into interviewing out there. I also, being from Oklahoma, I just knew I only wanted to be on a coast for at least the foreseeable future, so Miami was one of the other coasts that I wanted to hit. And Miami in your 20s? I don't know that I could ever have moved to Miami at my age now, but in my 20s that seemed like a pretty awesome thing and an adventure to go out to Miami and go to this new sort of rising shop.

I also had an interview set up at Wieden after I had had an interview set up at Crispin through some hard earned contacts and, you know, behind the scenes figuring out who I knew where and when. But instead I went to the Crispin interview first, and I interviewed for two days for about, you know, nine hours a day, across the whole agency and then never went back. It was a one-way ticket after all.

Charles: (14:21)

Just taking you back to your meeting with Steve Jobs. You're 19 years old, you're in an industry that you barely knew existed at that point, you only just discovered. How did you meet that moment? How were you able to stand in that moment and have that conversation, present that work to him? What do you remember about how you showed up in that moment?

Tiffany Rolfe: (14:41)

Well, there is something good about being really naïve and young, in that you don't know what you don't know. And I didn't really know what Steve Jobs was or is. And by the way, he wasn't quite even the Steve Jobs that he became because he had been, I think, kicked out of Apple at the time. So there was a little bit like, "Who's this guy? He just got fired,” you know? So there was a little bit of not really recognizing what kind of room I was in, even though I was like, “A lot of people seem to be caring a lot about what this person thinks.” And so, I still remember presenting him, some different website concepts for Bug's Life and I thought they were pretty good, and he didn't think they were very good. I think it was the first time I'd ever had someone tell me an idea is cheesy. And I was like, "Oh god,” you know? "That's terrible."

And the idea was actually, when I think about it, I still remember it and I probably share this story. But it was for Bug's Life and with the idea we had was to basically get people to think that your computer was taken over by bugs, you know, a virus. And it would screen grab your computer and your desktop folders but then have the little characters would pop up and they would animate and you would think that somehow they'd taken over your computer. Which is actually, when I even think about it now, I'm like, "That was pretty good.”

Charles: (16:00)

(laughs)

Tiffany Rolfe: (16:01)

But when I think about what he represented and the kind of marketer he became and known to be, is he really understood products, you know, he cared about the products, he wanted— the product was kind of the marketing. And then when you think about the simplicity of how we even see Apple ads today and the beauty of them and design at the core and how do you make sure— just show my product, show me what this does for people, I have a good idea, I don't need your good ideas, you know? He basically was saying "Show me my product. Show me the characters. I want the movie poster.” And also, he'd just gotten into the movie business, so he was probably like, "Hey, I'm in the movie business now, let’s show me a movie poster. I didn't get into this business to not do movies."

And so, there was, I think, just a learning about that, and our job I think as marketers is to not just come up with good, crazy ideas but to really understand the product, to care about it. What is it doing for people? How is it an extension of that out versus us layering on a new concept that doesn't actually connect you back at the core what those products are for people. And so I think that was a lesson. Also just presenting and knowing that you have to take a lot of feedback, as a creative person in this business. You get beaten down every day. Every day something of yours, your little baby, something you thought was brilliant gets destroyed, gets killed. And I remember Alex used to, I swear, if I was really excited about an idea he would kill it just to toughen me up and to prove to me that I could come up with another idea. My job wasn't to sell that idea, my job was to come up with more ideas. And so not being precious about ideas.

That's not to say I shouldn't be passionate about ideas and commit to making them as smart as possible. And sometimes there's those ideas where you're like, "This is so good, I have to keep bringing this back.” But that I shouldn't be so personally connected to my ideas that I don't think I can come up with new ones. And that, actually, my job is to keep solving and if the brief changes, then that's my job, is to come up with another one that's going to solve it even more. So that I think is important. Also, you know, listening to other people, understanding that other perspectives are as important to getting to great ideas as your own. I don't know if I knew all of those things (laughs) at that time. I definitely wasn't realizing I was having any life lessons. I just thought he was kind of a dickhead. But I think I gave out his email to a bunch of people because I was just annoyed and immature at the time. But I definitely, looking back, realized that that was a special moment and probably a learning moment and something that was a great thing for me to experience at such a young age.

Charles: (18:52)

One of the attributes that you bring to the table that I've always been conscious of and admired is your willingness and ability to show up. You just are willing to put yourself out there and be out front. Is that fair reflection? Does that resonate with you?

Tiffany Rolfe: (19:05)

Yeah, maybe it's because of how I got into the business, pretty young. I've never had really any formal coaching early on, you know? I didn't learn the proper way to do things, maybe. And some of it might have just been lack of experience, where I just did things. I didn't know what the right way to do things were, but I just knew I could do things the way I did them. And so I guess my approach to how I do work and connect with clients is just being very real, you know? To the point where I don't know that I'm the most polished presenter. I don't stand in front of a mirror and have everything perfectly polished and present in that way. I never learned the Bill Clinton, you know, thumb, fist, when you hold your hand, the expressions that you're supposed to use when you're compelling a group of people. But I think people hopefully sense that I'm being honest with them. You know, I'm trying to get and understand where their real challenges are and I'm always going to say what I think.

And so that has helped maybe build trust with clients to do bigger and crazier ideas. Trust with my teams, that I'm going to also put myself out there so it's not all on them. So I'll take risks together. So that's definitely, you know, been a way that I've navigated my career.

Charles: (20:29)

What have the last two years been like for you? How have you changed over the last two years?

Tiffany Rolfe: (20:34)

Yeah, everyone right? Everyone's changed. it's funny, I joke with Sean that we got the pandemic version of R/GA. We started at R/GA both around the same time, took these leadership roles, and had to really navigate a new role, a big role, for me personally in my career, taking on, in the middle of the pandemic, a global role. And at a time where there were no rules to be written, I couldn't look and say, "Hey, how has this other person done a global role in the middle of the pandemic? And been a mom, and been all these things.” And so I think it's been a lot of personal growth. But I think there's been a lot of positive. And I hate saying that, because there's been so many awful things. People have died, you know, it's been crazy. We've all had to be away from our family, our loved ones for that period of time.

But when you have such a big, significant change, it forces not just iterative ideas and iterative movement. You actually, really have to evolve in a big way. You can't have just little thinking. You have to go, "How do we fundamentally do things totally different? How do we work differently? How do we build teams differently? How do I parent differently?" And so the last two years really are about disruption of myself, of how I work, what I think about my life in many ways. And for that, I think it's been a good thing for me, as a leader. I've had to really think about things totally differently. There was no road map. And so I think a lot more interesting ideas and bigger changes, good changes, happened because of it.

And I always say, unfortunately it took a pandemic for us to disrupt how we work. But we've been working the same way, since the early days of industry and factories. And why are we still working nine to five? Why do we still expect people, talent to live in the most expensive city in the world if they want to work in one of our offices, for instance? Why can't we have more flexibility for people in terms of how they need to live in their own lives? And so there's a lot I think when you think about the last couple of years that let us reassess and go, "Let's change some things.” And so that has been I think really awesome and exciting about it. I think it's made me a better leader.

I don't know if I would be as good of a position in terms of where we are doing with the company and the kinds of things we've innovated on, without going through something like this. And I've balanced more of how I think about my personal life. You know, been able to integrate my children into my world more easily. I was honestly a little bit afraid of taking on a global role before I took this global role on, because I thought I knew what it meant. I thought it meant traveling around the world all the time, being on planes, being away from my family, you know, not really being anywhere. Feeling uprooted always. And that's the only way it would be successful. And then cut to, I have been doing a global role for the last couple years from my guest room in Shelter Island.

And so that opened up a lot for me to be like, "Wow, I see what this has done for myself, imagine if we rethink this way, what we can do for others.” And so even though I do think there's a lot that wasn't working about that, you know, we're now into— Mila, I'm on a— honey, I'm on a recording. What? It's not, here you go (laughs).

Mila: (24:20)

I need help.

Tiffany Rolfe: (24:21)

No you have to—

Mila: (24:22)

How do you spell Covid?

Tiffany Rolfe: (24:23)

Covid? You spell Covid C- you know how to spell Covid.

C-O-V-I-D.

You can edit, right? You can edit?

Charles: (24:32)

Yeah. For sure.

So notwithstanding, real life stepping into the middle of that… given the fact that you had no reference point about how to do the job, what were the leadership beliefs that you've held on to? What were the leadership beliefs that you used as a reference point for yourself, given the fact you could blow everything up and had to blow everything up?

Tiffany Rolfe: (24:52)

Yeah. Well, I've always been a leader or creative person… I've always been into what's new. What is the new thing and how can I do something different? I'm not really interested in just doing the same things over and over again. I think most creatives, I think to get better at one thing and keep going, and then it gets comfortable and more easy over time and then you can sit back a little bit. I've sort of intentionally gone towards things that I don't know and I'm scared of, but that's how I learn, right? I want to kind of embrace new technologies, new types of companies. You know, I went from Crispin which was the height… potentially, that was the height of my kind of junior career, moving on, and I could've gone to a big agency and run a huge team and I went to a small startup that was doing consulting and creative, which everyone thought was the craziest thing. Like, "Why didn't you cash out?", or "Why didn't you take on this other thing?"

But I think it was an opportunity for me to change and learn. And so I've always believed that, you know, you lean into change. How do you rethink and reinvent? And so, for this moment, for me in particular, it gave me even more of a palate for change, you know, to say, "Okay, we can just do things differently. We don't actually have to do them the same way as before.” So that I think, the embracing of change and being kind of uncomfortable, or being comfortable with being uncomfortable is something that I've always embraced and believed in. And that, I think, was part of this.

Charles: (26:28)

I hear more and more people, leaders especially, talking about the need to create emotional safety or psychological safety for the people around them. You were just talking about the fact that you head for things that scare you because it excites you and interests you. Do you see the need for psychological safety or emotional safety in the environment that you're leading? Or do you think that that's overrated?

Tiffany Rolfe: (26:51)

I think that is the perfect backdrop to that idea of change and discomfort, right? Where, I think to be able to have new, crazy ideas that we haven't done before, you have to feel like you have trust and security with the team, that there's a safe place for you to have those ideas. That you can express those ideas without being denied or being shamed. So I think those are counter-balances to each other. And so, while I like to pursue the unknown, I like to have a team around me that I know believes in me and we can venture into these unknowns together. And there's trust there and that my crazy ideas can be met with excitement. And as we explore, new terrains that we… I have people alongside and we can do it together. So I think you need that balance of having a safe space and feeling like you can take those risks and try things that you've never tried before, but you definitely still need to have the environment of people around you that help you create that safety net.

So I don't think those are at odds with each other, I guess.

Charles: (28:07)

You've been able to dramatically move R/GA forward. You were just named number two, I think, on the Ad Age A-List, which is a dramatic, improvement in the agency’s standing over the last two years. How have you been able - obviously you're part of a team that's done that - but how have you collectively, from a leadership standpoint, been able to do that?

Tiffany Rolfe: (28:25)

Well, we have a great team. We defined a purpose, which is designing businesses and brands for a more human future. And we made that purpose also our offering to our clients, so it's both our value proposition and our purpose. And part of that purpose is just to organize around an idea and go, "Hey, this is what we're all in here for. We're working towards the same goal.” Because it's hard to accomplish goals, right? It's hard to accomplish change. And if every single person in the team is working in a different path and a different direction and has a different goal, it doesn't add up to anything. And so I think that was a big part of how we were able to create some change.

I also think, like I mentioned, this last couple of years were disruptive for all of us. R/GA, for me, when I thought about going to R/GA, I actually saw it as a place that was about change and constant change and disruption of itself. It had proven that it could be different things over time. You know, R/GA has been many different companies. And they actually have an intent to change what they are and what they're about every nine years. I always say it's more like every nine months these days. So I knew going in if anyone can handle just where things are headed into the future, there's a culture of that that has legacy at R/GA. And so if I'm going to come into a place and try to move things forward, which is always hard to enter into the shoes of famous leaders that have done amazing things, it's rare to be able to take that and actually take it to the next step.

But R/GA was a culture that already had that at its core, and that's something that aligned with my values, as well. And so, part of it is just the DNA of R/GA, I think, that we were able to go, "You know what? This is us changing and doing new things here, this can be adopted by this culture.” Doesn't mean it's easy. We always say, "R/GA is not an easy place to work.” But, you know, it's a place to work if you want to learn and grow and do new things. And so that was I think a big part of it. I think the last couple of years, because it really was about this change also towards more of the vision that I think had been set out for R/GA, as well, in terms of technology and adoption of technology and where things can go, we found ourselves in a time where, you know, a lot of what we had all been discussing for years and probably Bob even had been discussing for years where, "Wow, we're in a moment in time where this is all happening right now. And we have an opportunity to be a leader with everything.” When clients and people go, "Oh my gosh, how am I going to embrace this new world where I'm on Zoom all the time and my mom is gaming with my six year old?" And, we have to figure out a new way of living and working. We thrive in this. This is what we've been waiting for. Let's not, you know, let this opportunity to lead and build this future go to waste.

I also think we really leaned into the culture of the people more than maybe ever. And to the point of having a purpose that's the same internally as externally. The idea of designing businesses and brands for a more human future, which is the purpose, was also about not what we're doing just for our clients, but what we're doing for our people. So the idea of, what does a more human future mean for our employees? You know, we knew we needed to create a culture where people, not just great design and great clients and ideas can thrive, but the people can thrive that need to make those. And so I think also by shifting more focus on to our culture and to our people, gave another dimension to what R/GA could be, too.

When I interviewed at R/GA with someone, they asked me if I was going to, you know, bring some plants in and change the dog policy to let some dogs in the building. And so, you know, there was a perception of beautiful, clean design, technology— that technology part of it, the future part of it, maybe over weighted the human part of that. And so, I think us as a leadership team wanted to find the right balance with everything also. There was backlash to technology happening, and still is. And I'm a tech optimist but I also am not naïve about what technology can mean. And so part of our whole strategy was, we need to really look at technology through a human lens, both for what we're building and what that means for our people. And I think that shift is helping us enable the vision that was set out, maybe many years ago, but really activate that in a more meaningful way that the people need today.

Charles: (33:15)

You're such a positive person, you're an optimist, you face the future, you like change. What have been the toughest things for you personally over the last couple of years? What's been really difficult for you?

Tiffany Rolfe: (33:27)

I still struggle with how will I balance things for myself. You know? I can handle a lot and, I give it to work, I give it to my family, I give it to all those things but, figuring out what that means as an individual. You're alone a lot in a room, I've worked from my closet, and I'm staring at myself on Zoom screens all day and if anything just that like, "Oh, wow, me as a person, how do I make sure I'm taking care of myself in all this too?" That's always something I've put last on the list, and that's something that I, you know… it can be hard during this to make sure you give yourself some time, right? To meet with some friends, to try to work out. If I struggled with anything it was just figuring out my own needs and how to deal with those during the madness of everything that was this last couple of years and everything that we were trying to solve.

So maybe that. But I think in some ways, some of that started to get solved, and I recognize that being at home, making time, integrating and merging life and work a little bit more can help with those things. And so some of the last couple of years helped me realize some of those things as well. Just when you start to see your world's collapsing where you're a mom in one place and you're a leader of a big team at another place, why do those things have to be so different? And so I think just a lot of personal growth and reflection were interesting during these last couple years as well.

Charles: (35:14)

And what do you think the future looks like from a leadership standpoint? What do you think leaders are going to have to bring to the table going forward?

Tiffany Rolfe: (35:22)

Well, couple of things, I think. We're all needing to be much more empathetic about how we lead teams and the work we do. You know, this industry, which I still believe is a big thing, you know, it's the work, it's the work, it's the work. But you're hearing more, you know, it's the people, it's the people, it's the people. So leaders that really care for and know how to build teams that feel valued, that feel like they're contributing in meaningful ways. That I think is a big one. Also I think so much of our job has been in - and this is related - in what we make. But I think the big challenge that we're all facing right now is how we make. So how are we working? How are we building teams across this more hybrid way of working? How are we building culture in new ways? How are we making sure many different kinds of voices are at the table and people feel heard? So I think we're having to just look at our jobs, not as, you need to be this epic idea machine, but you really need to be a leader of people and create those environments that help get to those great ideas.

Charles: (36:34)

And what do you think being empathetic means practically? I mean you hear the term. And in fact, somebody did a Google search on it for me a couple of weeks ago and saw the spike in empathetic leadership is going vertical at the moment. What does it mean to you, practically? How do you show up with more empathy?

Tiffany Rolfe: (36:52)

I try to always, first off, think about the best possible version of any scenario, and maybe that's that optimistic view, right? We're all coming to the table with our own lives, stuff going on in our own worlds, and I think we just are seeing it more than we ever have. So in some ways it's maybe more easy to see it because you're seeing my kids crashing in on my podcast. And when you just get a little bit of a more glimpse into who people actually are and the things that they're actually going through, the day-to-day struggles and when you're coming up, trying to figure out a client brief and a deadline, how you interact, I think it changes those little daily interactions. Where how I'm saying it, how we're showing up, how present you are, what expectations you have of people in that moment, little bit of padding and forgiveness.

I think it's all those little things that are really where it shows up, rather than just big expressions of grand statements of empathy. It's just in every of the little moments and everyday moments where, "I got you on this," or, "Don't worry about it," or, "Oh, I just went through something, I'm sorry I freaked out just now.” You just are more real. I think showing more vulnerability too, so that they have the opportunity to be vulnerable as well. Because I think we as leaders, I used to be that way, I think more so where I was— I didn't want to show all of my weaknesses, especially being a young female leader, I just wanted to be the strongest one in the room. And so, allowing for stuff to go wrong, allowing for mistakes. I tell people more about my nervousness and fears that I have, even public speaking, that never go away, you know. Just sharing more of our own vulnerabilities I think allows people to be vulnerable.

And then when those vulnerabilities are there, there's just more trust, then people are willing to share ideas even if they think they're stupid, they're willing to, you know, tell you feedback on ideas I might have and be truthful about the direction I'm giving them versus taking it blindly. So I think it just creates that environment you talked about where, what are those… what's that safe place? What are the conditions where people feel like they can express themselves? It happens in all the little- little daily actions.

Charles: (39:23)

Yeah, I'm really curious to see what happens when people start spending more time back in the office, whether we lose that forgiveness and understanding because we're not seeing people through this lens and also because, there is, in some strange way, almost a safety being seen through a screen that we can shut off, we can decide how we actually want to show up. Whereas we're standing in front of somebody, I think there's- it- it's almost more vulnerable in some respect. So I think it'll be interesting to see how people show up. Last couple of questions for you. How do you lead?

Tiffany Rolfe: (39:57)

I think I lead… I definitely lead by example. You know, I'm trying, I think I've gotten better to… I think early on maybe that meant too much taking things on myself, And I think I've learned how to lead by example but not just lead the whole project. And what I think I mean by that is, you know, I want people to see that I'm passionate about things, that I listen to clients even if some of the feedback, I maybe don't agree with, but how do I talk them through it, I demonstrate when I'm willing to stand up for something. And so I also like to do things in front of people. I think there's some leaders that kind of do it behind closed doors or they go away and they come back with the big "Aha".

You know, maybe that was the Mad Men days where it's just you wow clients, you know, you show up with this epic presentation and it feels like magic. And I guess I've just never been a, "I'm going to go away and it's going to be like magic.” I kind of bring people into the kitchen. And I do that, I think, with clients and I like to do that with teams. I like to be on the spot and give clear feedback when everyone's watching, I like to give feedback to clients, not go away and think about it and come back. I want them to see the wheels turning and, you know, how to do things when we just show it all and reveal it all so they can actually see how we're thinking. I think it's harder… young people, when I started out, you know, we had walls where paper was on the walls and people walked around, they talked about things, and you know, got into a room. And now things happen in Google Docs and they happen behind in our own little worlds. And it's harder for teams to learn. How are you doing what you do? How— what is this— where did this idea come from? How do you give feedback? How do you talk to clients?

And I think leaders need to keep teaching and helping young talent understand what it is they do. It's not magic. It's not just because I'm, you know, Tiffany Rolfe and I've been doing it for years. But there are questions we ask of the work, let's break that down for them and at least show them how we do it. So for me, I'm a very maybe exposed leader, a very open sourced leader. I like to just put it all out there and I think that hopefully then people see that and learn from it.

Charles: (42:40)

And last question, what are you afraid of?

Tiffany Rolfe: (42:44)

I guess I'm… if anything, I'm… it's weird, people always say I'm fearless. I never like that because then I'm like, you know, "Then people will actually see me afraid and it'll be worrisome.” But I guess I'm afraid, if there's anything, it's just afraid of being stagnant, of not moving forward. I never want to feel like I'm not learning, I'm not growing. And then, you know, I'm always afraid, I think, of… when you become a mom— when I became a mom, I think you have a whole new set of fears. And if there's anything I'm afraid of, it's just for them. It's for what their future's going to be like. Who would've ever thought that we would be living for two years, wearing masks, not being with each other, being socially distanced. Not even leaving your home basically for years. If you would've told me that at the beginning of this, we would've been all really afraid. I think if anything it's just what is, you know, I'm afraid of— without what I think I have a role to play, what is this going to be? What's this world going to be?

And so for me, it's how am I building? I'm afraid to not keep moving, to not keep pushing things forward, to not make change. I feel like I have the opportunity to build things, build things with technology, to build the world that we want to live in and not just let things happen. Not just let things get built for us. And that's, I think, why I've always sought out new things and how to leverage those new things. And I think that's our responsibility as agencies, as clients. There's the little of I'm afraid to, "Let's wait and see what happens," and the only way for me to not be afraid is to be able to change things and do something about it.

Charles: (44:39)

Can't say it better than that. I've always been struck by any number of things about you, but there are three things that really stand out, particularly about today's conversation. I think you have this remarkable capability of building community, both within the groups that you work with but also, I think, more broadly. I think your work is littered with examples of creating community. I think the fact that you're willing to meet the future on its territory gives you a big advantage over a lot of leaders who I think are waiting and reacting to stuff and trying to get back to some version of the past. And I think how much you care is just obvious. Every time I talk to you I'm struck by how much you care. And I think those three attributes really do stand you in great stead from a leadership standpoint. I want to thank you so much for coming on today. I know how busy you are. And I just so appreciate the time, the insight and your willingness to share so openly.

Tiffany Rolfe: (45:30)

Thanks Charles. Thanks for inviting me on. You're always unlocking things and ideas in me that I'm sure, you know, I've taken with me over these years. So I really appreciate everything that you've done as well.

Charles: (45:43)

It's been absolutely my pleasure.

—————

Let us know if there are other guests you’d like to hear from, and areas you’d like to know more about or questions you have.

And don’t forget to share Fearless with your friends and colleagues. 

If you’d like more, go to fearlesscreativeleadership.com where you’ll find the audio and the transcripts of every episode.

If you’d like to know more about our leadership practice, go to thelookinglass.com.

Fearless is produced by Podfly. Frances Harlow is the show’s Executive Producer. Josh Suhy is our Producer and editor. Sarah Pardoe is the Media Director for Fearless.

Thanks for listening.