Jill Cress of H&R Block
WHAT ARE YOU INVESTing IN?
"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT
Episode 280: Jill Cress
Here's a question. What are you investing in?
Hello, I'm Charles Day, and welcome to Fearless Creative Leadership, now in audio and video.
Here we explore how people in all walks of life – from business leaders, to artists, to athletes – unlock creativity and innovation in themselves and in the people around them. And in the process, how they move the world forward.
This episode's guest is Jill Cress. She's the Chief Marketing and Experience Officer for H&R Block.
She also serves on the board of the AdCouncil, and she's been recognized on Forbes’ list of the World's 50 Most Influential CMOs.
Before H&R Block, Jill spent 20 years at MasterCard. Now, a leader who spends most of their professional life working in financial institutions could easily build their success around the study of data, but the foundations of Jill's leadership are based on the most valuable investments of all.
“I also really think that relationships are a thing to invest in, and that you carry those forward. And that is a big part of what has fueled my leadership, is the ability to have an impact on people and to help them realize their ambitions and their personal purpose. And that comes through discovery, through that natural curiosity that I have, and wanting to build relationships and understand what matters to those who are around me.”
Delivering results has always been table stakes when you're stepping into a leadership position, and money will and should sit squarely on that table as one essential definition of success.
But enduring financial success is a consequence of your willingness to take your eyes off the financial prize and fix them squarely on your most valuable assets:
The people that work for you. And what matters to them are two things.
First, that they matter. And second, that what they're doing makes a difference.
During our conversation, I talked to Jill about the creativity diagnostic tool that we've developed. It measures when leaders are creating the conditions that maximize the creativity of their people.
One of the critical insights that shows up time and time again is that the very best leaders are fully invested in creating a culture that ensures that everyone feels seen and heard and respected. Now, this investment carries personal risk, because it can make you as the leader feel vulnerable, and it is time consuming. But the ROI is through the roof.
So what are you investing in?
Here's Jill Cress.
Charles (02:56):
Jill, welcome to Fearless. Thank you so much for coming on the show.
Jill Cress (02:58):
Thank you for having me.
Charles (02:59):
When did creativity first show up in your life? When are you first conscious of creativity as a force in the world?
Jill Cress (03:05):
From very early days. I can remember creating my own versions of cereal box designs, probably when I was two or three. I'm a child of the seventies and spent a lot of time in front of network television in the US, and I was really fascinated by ads and jingles. And my father worked at Quaker Oats, and so we were surrounded by a lot of new products and trials of new products. And that was the era of the mascot, and so many characters involved in packaged goods and cereal was a favorite of mine. So I feel like I was drawing and writing creative jingles from a very early age (laugh), although don't trust me to copyright even a sentence, but I fancied myself an aspiring creative at a very young age.
Charles (04:01):
Looking back, do you remember what kind of the thrust of the cell was of the package designs that you did? What did you find you were focusing on as attributes?
Jill Cress (04:09):
I think I was really drawn to bright colors. I can remember creating my own versions of Fruit Loops, and I loved the bold colors and the contrasts, and I loved the idea of a jingle and a logo even back then, or maybe a catchphrase, let's say.
Charles (04:28):
Yeah, I can imagine. I have such vivid memories of growing up and eating cereal around the breakfast table, and did we have the toy out, or what was the thing on the back, and all of those things. So really special, actually.
Jill Cress (04:41):
Oh my goodness, the fight for the toy, the giveaway. I forgot about that, Charles. My brothers and I would, yeah, really have to have a system for how we could equally distribute the merch and the goodies that were in the boxes back then. It was so exciting.
Charles (04:57):
Yeah. Beyond cereal package design, how did you express yourself growing up? What were your media?
Jill Cress (05:02):
I was a children of the theater. I wanted to be onstage from a very young age, and I think much to the frustration sometimes of my extended family, I was often creating plays that I wanted, you know, full costume and production for. Around Thanksgiving, so I can remember a production of, you know, the, the pilgrims, you know, landing, (laugh) landing in the US and things like that. So I think I was inspired and looking to be a storyteller from a very young age.
So it was a lot of creative writing, a lot of these little short plays that I would write and script out. It was just frustrating because I couldn't get people to play with me (laugh). My brother never really liked the characters I chose for him. I wanted proper costumes and things like that.
And then I went on to participate and do children's theater in Chicago as a kid, and really enjoyed musical theater. And I'm still a big fan of the theatrical productions, and we're fortunate that we live in New York City and are able to experience theater and entertainment of all kinds.
Charles (06:15):
It really is remarkable, isn't it? How rich the environment is in New York. We were at, we saw Sondheim a couple of weeks ago, which is fantastic. I don't know if you've seen that yet, but it's–
Jill Cress (06:23):
Not yet, no.
Charles (06:24):
–worth a trip. And then, we've got strong Scottish connections and we'd never been to Carnegie Hall. And my wife said, we have to go to Carnegie Hall, right? So we looked up what was playing, and it turned out that last Saturday night there was a Scottish Hui, which was a celebration of Scottish music. Alan Cummings was the MC, and they had–
Jill Cress (06:44):
Oh my goodness.
Charles (06:45):
–Seven or eight different acts that were just extraordinary. And the sense of community in that extraordinary auditorium was very remarkable. And the kind of the diversity of the kind of acts that they put on was just remarkable. So, yeah, New York is so rich in that. I think it bring, it makes such a difference.
Jill Cress (07:01):
And as you start to discover places grand like Carnegie Hall or smaller venues, you just start to become amazed and really in awe at the depth and breadth of all the culture that is at our fingertips. It almost can become overwhelming, and you really have to sort for impact.
Charles (07:22):
Yeah, no, I think that's exactly right. When did leadership show up on your horizon? When, how, have you always wanted to lead?
Jill Cress (07:28):
Yes. I started my first business when I was, I think maybe eight or nine years old. And as I look back on it, I started a, I called it Kiddie Camp. It was for kids on summer break. And I'm the oldest, I have two brothers. And I think back now and realize that it was grounded in the insight of my mother always trying to keep us busy. And I was always looking to hustle and make money to fund one of the arts or crafts or projects that I was interested in. And so I started a Kiddie Camp, and I recruited a gal down the street to be my number two on this endeavor. And we recruited 10 kids, and we did an activity with them three times a week over the course of, I think, it was three weeks, one summer.
And I started to learn about what it meant to lead an associate, my first employee at that time, and also how to think about, you know, keeping things organized, having a program and leading the kids who joined my Kiddie Camp (laugh).
And then I started working as soon as I could. I applied for a job at the local grocery store. I grew up in Chicago and I worked at the deli. And I also realize now, I didn't understand it at the time, but I was very fascinated by the four Ps and did a lot of experimentation with the Product, the Placement, the Promotional Pricing, and had, it was a family owned grocery store, so I had the leeway to do that, as long as the sales were coming in.
And so I started when I was 16, as soon as I had, I was legally able to work. And I think by 17 I was the deli manager, and I was working on schedules and negotiating all the trade-off that come with trying to get young people to work on weekends. And so I think I was always interested in leading, and I guess maybe the younger version of myself would probably say that I was interested in being in charge. I think that I've certainly evolved and grown, but I like to direct. And so I think I was always interested in what that meant.
Charles (09:40):
What kind of environment did you grow up in? Because obviously you had, you were really independent, right? From a very early age. I mean, you were clearly filled with self-determination and personal expression. What kind of environment did you grow up in?
Jill Cress (09:50):
Yeah, my parents created a really empowering environment, I think, because I was always full of big ideas, and they probably didn't know what to do with all of them. But I grew up on the south side of Chicago in a really lovely and wonderful community. We lived quite proximate to both of my sets of grandparents, but really close to my dad's grandparents. And they were Polish and Croatian immigrants. My grandfather was a steel worker and my other grandfather was a bus driver for the Chicago Transit Authority. And the big gathering moment for us was Sunday dinner. And I was a very engaged, observant, curious participant of the Sunday dinner, and can remember my grandparents talking about the old country. And I was very intrigued by, like, where is this old country and how does one get there? And, you know, why did people decide to come to this country?
But I think the things that created that sense of empowerment and independence were the stories of people who worked hard, who came to America to achieve something. And lots of conversations about kids who worked hard and then were able to go to college, like my dad did. And my dad was an executive, as I said, he worked at Quaker Oats, and we kind of straddled both worlds of being very much a part of this Croatian and Polish community in Chicago, and everything that came with being a part of that, that culture and the work ethic, and my dad having done, you know, quite well from the place, you know, where he was raised, where it was really important to him that he got an education and could provide the same for his kids. And so with that, I think there was always, you know, an interest in nurturing the things that I was passionate about, and my parents working hard so that I could be in children's theater and explore all of my passions and have the kind of education that I wanted.
I then really insisted on leaving the neighborhood that we grew up in on the south side of Chicago to attend a Jesuit prep school in the city of Chicago, which was quite an ambitious commute, especially for a girl at that time. I had to take a bus from the south side of Chicago an hour into the city of Chicago, and of course this was pre cell phone days, and so if I would get stuck in the city, it was quite a production for me to find my way home. But I really do feel that somehow my parents instilled a sense that I could really do and achieve whatever I wanted to do, which was a fantastic way to grow up.
Charles (12:27):
Amazing way to grow up, actually.
Jill Cress (12:29):
Yeah.
Charles (12:29):
I lived in Chicago for 20 years as well, so the idea of at that point coming from the south side up into the city would, yeah, that would be a thing that would put off most parents and most children, I think.
Jill Cress (12:40):
Yeah, I thought it was really adventurous and I had set my sights on attending this Jesuit prep school, St. Ignatius College Prep in Chicago. It had become a co-ed school maybe four years prior. And I can remember thinking if I didn't get in there, then I just probably wouldn't even go to high school, because everything else felt like it would be, would fail in comparison to the magic in awe and wonder that I thought I would experience, and actually did. Really was an experience that I think set the foundations for how I thought about the world around me through Jesuit education, the incredible people that I met, the diversity of people that I met, getting out of the bubble of the south side of Chicago. And it was really wonderful, and I was determined to do whatever it took for me to do that. And, you know, including having to set my own alarm and make my own lunch and breakfast and get myself to Roosevelt Road (laugh) in the little Italy section of Chicago.
Charles (13:39):
So the environment you were raised in clearly had a profound effect on you. How much of that have you been conscious of and bringing into your own leadership?
Jill Cress (13:47):
I guess that human that I was, is very much still a part of me. And I think one of my superpowers is curiosity, and really understanding context and what motivates people. And I think a lot of that came from the many Sunday dinners, and listening and observing and understanding motivations. And so I think if you were to speak with the people with whom I've worked, they would tell you that I very much invest in getting to know them both, you know, as a human and as an executive, as someone in the workforce.
I'm very focused on those connections and I think relationships are the other superpower. And so I was just chatting on the train into New York City this morning with someone with whom I worked at MasterCard, and then came to work with me at National Geographic, and is now endeavoring into something new.
And so I also really think that relationships are a thing to invest in, and that you carry those forward. And that is a big part of what has fueled my leadership, is the ability to have an impact on people and to help them realize their ambitions and their personal purpose. And that comes through discovery, through that natural curiosity that I have, and wanting to build relationships and understand what matters to those who are around me.
Charles (15:08):
The intimacy of that is really powerful, and the value of that for the people that work for you is self-evident, right?
Jill Cress (15:14):
Yeah.
Charles (15:15):
The challenge I think is, how do you draw the line between that level of intimacy and familiarity, and still, when you need to be, being the boss, for want of a better description at this particular point, right? There are times where you have to make the hard call, you have to make hard choices. How do you navigate those two realities while honoring both of them?
Jill Cress (15:35):
Yeah, it's a really powerful and important question. I think I have been the beneficiary of really warm, intimate relationships as someone who was growing up in corporate America. I spent the good majority of my life and my career at MasterCard, which was a really nurturing, wonderful environment. And I think I learned from example through the leadership that I experienced there, that, you know, we used to talk about when I was at MasterCard, the importance of being open, honest, direct, yet fair and caring. And so I think through that, and structuring conversations, and not being afraid of that open direct communication… Related to that, I just had the opportunity to hear Adam Grant speak and he talked about the importance of feedback, and open honest feedback is one of the greatest signs of loyalty. And so I think being able to be clear, to be direct, but to also be warm and welcome, welcoming, to be fair and caring, was something that I just learned through growing up in a culture that really valued that.
And I think that did allow me to both build those relationships, but understand that there were times and places for hard, difficult coaching conversations, and to your point, sometimes very hard conversations. But I think if you approach those through the lens of humanity, and understanding that at the end of the day we're humans that are engaging with each other, albeit sometimes the circumstances change. But I think with good relationship equity, it can make even those more difficult conversations easier for both parties. But I think that, to me, relationship is an important part of how we navigate the good and the bad times.
Charles (17:30):
Yeah, I find it so interesting that people struggle so much with having difficult conversations, and they feel like they're doing the person a favor, or they don't want to upset them, or there's some normally pretty strong emotional component. I've always felt, and this was true when we were running our film editing company back in the day, but I've always felt that it was the greatest service you could offer somebody is be honest with them about how they're showing up in their career, and give them a chance to do something about it or make a decision that maybe this isn't the right place for them. But I mean, it's their career, and I think as leaders, if we deny them honest feedback, we're doing them a huge disservice.
Jill Cress (18:04):
I absolutely agree, Charles, and I think that it's one of the more challenging skills to develop, but I think so critical for how we lead. And in my current role at H&R Block and almost everywhere else that I've worked, we've had some sort of associate engagement and, you know, getting that feedback as to how are you leading those that are in your charge? Simon Sinek has a great quote that I think of often, which is, being a leader is not about being in charge, it is about taking care of those in your charge. And what a great pivot as we think about what is our role in leading, and then connecting that back to feedback through an associate engagement score, you get that feedback as to, how are your employees and those that are in your charge experiencing you? And I can remember early on in leading a large group of people getting some feedback through the survey that I was not providing feedback.
And I was so surprised by that because I felt like it was something that I was quite comfortable with and I did regularly. And one of the things I learned as a result of that was the importance of being really clear when you are giving feedback. And I can remember meeting with the head of, I guess we called it Human Resources, currently People & Culture at MasterCard at that time. And he asked the question, when you're giving this feedback, do people know it's feedback or because you are so approachable and relationship oriented, are they receiving it as a conversation?
And that was a big unlock for me as a leader, which was again, to have that rapport, to be warm, to be in a relationship with someone, but to be really clear on, this is a conversation where I want to share some feedback on maybe how, you know, how you showed up something that I think, you know, we could have prepared for better how I'm reflecting on my leadership and engagement with you, but to really shape a conversation that is about coaching through that lens.
Charles (20:01):
Yeah, I think the context of leadership is so important, isn't it? And being able to help people understand what they're doing and the impact that that's having, in terms of where the company is trying to get to. And I'm always struck by how often companies talk about some version of vision, but I see gaps frequently between that and their willingness to actually act in ways that demonstrate to people that we are really serious about this. And I know that H&R Block is purpose driven and curious to get your perspective on purpose, which has been around now for, what, 20 years or so, really as a concept.
I mean, Jim Stengel has been on the podcast a couple of times. I always call him the Dean of Purpose because he was the first person I ever heard talk about it and articulate it. I think it's come in for some criticism in more recent years, I think in some cases has become a bit of a, you know, kind of a coverup for a bunch of other stuff. But you clearly have committed and invested in purpose.
Can you just talk a little bit about why purpose is important to you, and what you've learned from a leadership standpoint that makes purpose the right reference point for you?
Jill Cress (21:05):
Yeah, as I reflect on the journey of my career, having spent really the good part of my career at MasterCard, which really cared deeply about its purpose in fostering more financial inclusion, and then making a choice to go to National Geographic, which cared deeply about the protection and conservation of the planet, the role of exploration in that, and then onto PayPal and then H&R Block, both very purpose led companies. At H&R Block, we created this category of tax preparation through the lens of providing help and inspiring confidence around what is one of the most intimidating and yet financially important moments of the year.
I realized that for me to thrive and to feel good about the work that I'm doing, as I look back on all of those experiences and those corporate cultures, purpose was really foundational to, not what they did, but why they did what they intended to do, the work that they did.
And I think that really has resonated with me as a human and allowed me to lead. And so, as I think about the importance of believing in what we do, it just matters to me. And so I think, you know, when you look at the current state of where we are with purpose potentially becoming more scrutinized, you start to see, based on some of the actions that firms are taking, how organic it was to what they believed in.
I said it earlier, there's what we do, but then there's why we do it. And I think for me, that is just something that I find really important and motivating, which is who is the, as a consumer marketer, who is the consumer that we're serving, and it's not about the thing that we do, but the job that it does for them. And doing that in a really intentional way.
Charles (23:07):
And I was going to say, I assume, but I don't want to assume, let me ask you the question. So that context, here's the purpose, here's why we do it, here are the people we're trying to help, essentially. Does that give you the ability to make those business decisions that are not always short-term oriented in their sort of success metric? So many businesses are run based on quarterly earnings numbers, and so their ability to really make long-term, even midterm investments, I think are really limited. Do you find that having that kind of clarity about why you're doing what you're doing and who you're doing it for gives you the ability from a business standpoint to build your leadership perspective from a longer length?
Jill Cress (23:45):
Yeah, it's such an important question. And all of those firms that I've referenced, H&R Block included, are, you know, both very commercially, or both commercially and purpose driven at the same time. And it is not always easy to make the trade-off between something that is short-term and performative, and something that may take time to play out. But I think the experiences that I've had is that when you, such an overused word, but when you show up with authenticity and you are showing up with a sense of purpose for the clients that you serve, it will serve you better in the long run. And so, you know, it often comes down to getting that balance right and proving the role of purpose out.
And I think as a marketer, it is important to bring an appreciation for the commercial orientation of what the firms that we're working for are doing, but to really push for the balance of commercial outcomes with the purpose-led outcomes, and ensuring that we are really thinking about the consumers, the constituents that we serve through the lens of what really matters and why we do it.
You know, working at National Geographic was a great example of that, where we were really in service of the role of exploration to understand geography, and yet we were a media company. And so there was always this really, I think as I look back on it, healthy tension of, how do you think about the importance of advertisers, which fuel our ability to, you know, tell great stories on that platform, with ensuring that they were advertisers that had similar values? And you know, that was the era, I've been gone from National Geographic, I think for almost six years now, but that was the era we actually worked with Jim Stengel at the time on, you know, greenwashing, right? And so just really being clear about the importance of not only having a purpose, but standing by that, and ensuring that you were thinking through, how do you both partner through the lens of a commercial opportunity, but also through the lens of like-minded purpose-driven partnerships that we created.
Charles (26:05):
It's so incredibly important. We've developed a diagnostic tool that allows us to show organizations, what are they doing that unlocks creativity and their people, and what are they doing that's inadvertently getting in the way. And one of the things that has been, become a profound truth, actually – we put together a profile of all the leaders who've taken this and saw where their strengths and areas of focus were and where they were less focused. And the norm is becoming, or sort of the narrative theme is, sort of the narrative thrust, is that the best leaders all have a clear vision of some kind. They understand what it is that they're trying to take, where they're trying to take the company. The thing that often is a shortfall are exactly the two things you've just described that you do. One is, are we clear about who we're trying to impact? And many leaders are not.
And the second is, are we willing to act in ways that demonstrate we are committed to this vision or this purpose? And again, many leaders are not willing to do those things, or don't emphasize those things.
And so what happens within the organization is, people hear the vision, start to buy into that, make the choice to go and work at a company for that, in many cases. And then when they get there, they suddenly discover, oh, A, you're not really sure about who we're trying to talk to and help. So I pull back a little bit emotionally because now I'm not sure. And then when you don't demonstrate through your leadership behavior that you're really committed to doing things, if everything is just about short-term financial gain and benefit, then I'm going to pull back even more, because now I think you're not really serious. So you've sold me this thing over here and now you're really, but it's really just an excuse. And it's proven out over and over again that the best leaders articulate exactly what you just have, which is, these three pieces are really fundamental. Does this resonate for you?
Jill Cress (27:48):
It does. And I love that. I'd love to hear more about the work that you've done at another time, because it's fascinating that you have data around that. And I think data is an interesting connective point between how profit and purpose come together.
We do a lot of work to understand, are we gaining those emotional deposits with customers through the way that we are bringing our solutions to them? And so we do a lot of client engagement to understand when we are working to provide help and inspire confidence around the tax moment, which is, you know, a big part of the business that H&R Block is in, are we meeting the expectations that clients have? And it is such an intimate personal moment. It's almost like a relationship that a human has with their physician. You're really going in and divulging the totality of your financial relationship, and you have to be quite vulnerable at times.
And so we organize how we show up around, we call them the four Es and, are we setting Expectations so they know how much time it's going to take, what it's going to cost them? Are we making it Easy? Are we bringing the Expertise to really inspire that confidence? And are we bringing Empathy? Because as your financial situation plays out through the tax return, moments that require a lot of empathy come into play.
And so as we seek to serve our purpose, getting the data really helps to reinforce that virtuous cycle because, you know, when we have clients who are not satisfied, and they don't come back, and that results in a negative financial impact and outcome for the company, you can see it in the data that says, we're not really living our purpose. We're not really providing the help and confidence that our clients expect to have from us. And so I really love the power of data and linking how important having that clarity of why we do what we do, is to achieving the financial outcomes that are so important to our ability to continue to do the work that inspires us. So yes, it, it really is, it is a very interesting observation that you shared.
Charles (30:02):
I think it so resonates for me that you've managed to codify key aspects of this. And one of the elements I think that has been missing from creative businesses for too long, which is this kind of recognition, understanding that we can, actually, quantify and codify some of the conditions that allow creative thinking to really come to the fore be an enormous business resource.
And I think we've been so, for so long, people have thought, hire smart, creative, innovative thinkers, put them over there somewhere and hope they come up with something magical. But I think, you know, what you are describing, or what I've experienced, as well, is in fact, let's create the conditions that we have, what we've learned, and we can recognize and identify as being those that really foster creative thinking and innovation.
Jill Cress (30:42):
I absolutely agree with that. And I think we are so fortunate to be living in an era where we have access to so much data around sentiment. And I think one of the most important things for us to do is to create that North Star, and to work to have the systems in place so we can codify that and that we are embracing what I think is such an intrinsic part of being a leader, especially in the creative space, which is to bring that curiosity to really understand if the work that you're doing creatively for the customer that you seek to serve is really landing with them and what can you learn.
And I think that has been the impact of that is, I think marketers need to be much more resilient than they were in previous versions of being a marketing leader, because you could rely on things like awareness and reach and impressions and feel like you are doing your job.
But now we get real time feedback from our customers and, to your point, about who, I believe deeply and you know, not just having a demographic target, but understanding what is on their hearts, what is on their minds. And, you know, we get real time signals through work that we do in social. We can put something out today and we'll know this afternoon based on engagement metrics if it is resonating with the audience that is important to us.
And so I think the modern marketer really does have to think about the role of, what is the learning journey, and how do you codify that, and how do you stay resilient when you may come up with something that you think is genius and really well done that isn't landing with that audience?
Charles (32:24):
The kind of leadership you are describing is both human and really strategic. I mean, it's that fabulous combination. You know, I like to talk on this podcast about sitting at the intersection of where strategy meets humanity, which I think fundamentally is where great leadership does sit actually. I'm also conscious that not every company provides that kind of environment, and that kind of leadership is not always welcome.
Are you conscious in your career, as you look back and forward, of the importance of casting for you, like making sure that you are working at the right, in the right kind of environment, at the right kind of, the companies that have the right, a mindset that matches yours? Are you conscious of that? Are you aware of that?
Jill Cress (33:01):
I am quite conscious of that, and I coach and mentor many people that are in my network on the importance of that, and really using a rubric to decide what are the things that are important to you, not only in the outcome levels of a job, but really, how are you going to ensure that you have a rubric for the things that matter to you personally?
As I look back, I was really fortunate to have spent so much time at a firm, MasterCard, which was such a great place for me. And I was cast so well in taking on roles where I could be bold, where I could work on transformation. I was really always on projects that were at the precipice of what was next. When I started there, I was working on debit cards, which was a nascent category. I worked on some of the first co-brand programs that were created in the US, and then worked on a Global Center of Excellence.
And so I was always at that intersection of, you know, strategy and understanding what was top of mind for consumers and how we could create value.
As a result of that, I think my experience in staying at that firm for 20 years was, well, that's just what it means to work in corporate America. You're just cast in an environment and a backdrop that works for you. And I learned that that wasn't the case. And as I started to think about my moves, one of the most important investments that I made in myself was working with an executive coach.
And when I had to make a decision on taking a new role, when I chose to go to PayPal, which was the role I had previous to H&R Block, we had created a rubric of the things that I was sorting for. And it really helped me to move beyond kind of the common things which were title and compensation, to the backdrop of, what was the context, what was the role of strategy, what was going to be my ability to impact and influence change, what were the people like, that I was going to be working with?
And I had, when I actually chose to go to PayPal, I didn't, I went from being a Chief Marketing Officer to running consumer marketing without that title. And what I realized was that the title didn't matter as much as the work and the environment and the complexity and having a seat at the table specific to strategy.
And so through having that rubric and working with the coach and being really intentional about, what did I want in my next role in the way of impact influence, I was really craving leading a large group of people. I was missing leading a global team, which was what I did at MasterCard. And so by understanding that, I realized that it wasn't about the title, it was about the impact that I could have.
I also took a move at MasterCard where I was, it wasn't even a lateral move. I was running B2B global marketing, working for the CMO, and as the company was becoming more consumer-oriented, and I saw that that's where my gap was, I took a decision to not work for the CMO and work for the Head of Consumer Marketing. I most certainly wouldn't be sitting here in this chair having this conversation with you if I didn't do that.
So I've made choices on filling skill gaps that I've had that were important to me and part of that rubric at the time, and also making decisions about the environment and my ability to lead. And so I think understanding that is important.
Charles (36:28):
Oh, critical, I think. Why do you think more people don't bring that kind of intention to their job situation, right? To the, what's my next move going to be? I mean, what you are describing is very much the advice that I give all of my clients who are in some sort of transitional phase, which is, you know, somebody said, somebody I really respect said to me about a year ago, what else do you want to find out about yourself? As a kind of a life reference point. Which I've found really uplifting and kind of motivating, much better than what legacy do you want to leave behind? Who knows what we're going to feel like in 20 or 30 years? But the question of, what else do I want to find out about myself while I still have the ability to have influence over that question, seems to me to be particularly profound and provocative. Why do you think more people don't take more care, I guess, for want of a better word, in terms of the choices they make about where they work?
Jill Cress (37:15):
I suspect it's a combination of things. I think ego is a really big driver of that. And we, you know, I've talked to lots of people about the choices I've made and tried to share some of those experiences, but for a lot of people, title and dollars are the North Star for them.
But I think that the other thing is probably really being clear about that, and understanding what it is that makes you thrive and how important that is to your own satisfaction. And so I think it gets to, I know something you've talked to others about on this podcast, which is, how are you structuring your time? And if you're just always on the chase and you're just, you know, chasing after, you know, an accolade or some sort of achievement or the next big title, and you're not thinking about, what is the setting that I'm in, and am I happy? Am I really getting the return on all of this energy, not only through how I'm recognized or compensated, but through how I feel at the end of every day, how you're able to deliver on the things that matter to you?
To me, it's to make an impact on the people that I have the great pleasure and feel so honored to lead. But if you don't have the time to think about that, I think it's really hard. I mean, one of the greatest is actually having the time, when you are about to take on transition, to be really intentional about setting the stage. And I think it's probably a function of architecting the way that we want to spend our time today. Instead of thinking about just, you know, the impact or the legacy and the accolades, I suspect.
I can remember when I made the hard decision to leave MasterCard, a good friend of mine was a coach, and I said to her, it's really important for me, when I leave, to send the right signals. And she said, we need to brand your resignation. And I thought, oh, this is so interesting. And we talked a lot about that. And before I even started to talk to anyone at MasterCard about that, I thought about the experience that I had there, and I came up with the branding of leaving with gratitude and grace.
It shaped me as a person. I was able to travel the world. My family and I moved to Europe, we lived there for four years. We grew as humans. We had the experience of learning different cultures.
And when you leave, I think – so that was the gratitude, which was I grew as a person, I grew as a mother, as a wife, all of the things that that company gave me. And I thought, gosh, that has to be such, that has to be the headline.
And then I do think oftentimes, because no place is perfect when you leave, there are always going to be skeptics and they will want to get a sense of, you know, what's wrong, and what were you thinking about this particular political situation that was going on within the company at the time.
And I thought, leave with grace and just don't go there. And so anytime I would have a conversation in those weeks that I was preparing to leave a place that I loved so much, I just kept thinking of that headline, leave with gratitude and leave with grace.
And so now I do the same thing when I enter a company, I think about what is that branding, what do I want to bring? And I think about it, even in my personal life. We were sharing offline that we just made a big move geographically. And so, you know, just taking time to think about, how do you want to show up? How are you going to be the best person that you can be, in those environments that we're in?
Charles (40:46):
And when you walk into a new position, do you let people know, this is why I'm here, this is who I am, this is the difference I want to make?
Jill Cress (40:53):
I do, yep. I've created a bit of a one-pager that I use, and I share it with the people that I work with. I share it with the team that I'm working with. And I've really learned to be quite okay with being very vulnerable. And so I talk about my motivations, I talk about what I'm looking for. I've learned, through growing, that the most important thing we can do is talk about the things that we don't know, and what our gaps are. And so, yeah, when I landed at H&R Block, I was very clear about why I made that choice, the impact that I wanted to have, where my strengths were, where I was going to need help from the team. And boy, I will tell you, just as a category, taxes are quite a complex category to navigate.
And so just being vulnerable about understanding the relationship that humans have with money through all of the places that I worked, but the complexity of what that means in such a highly seasonal business, and asking for help so that people could, the people around me, could help me learn more quickly, was a big part of that.
Charles (41:56):
Vulnerability, I think, is one of the most misunderstood and underestimated leadership capabilities.
Are you conscious of more men being able to demonstrate that quality, as well? Or do you think that it's still more prevalent among women leaders?
Jill Cress (42:12):
I think you are, I am observing it more frequently than I did in the past with my male colleagues and other men that I know. Women, I think, are innately more tuned into their vulnerabilities, and willing to share them.
It's interesting as you asked that, I was thinking back to a moment when I was an account lead at MasterCard, and we had a female executive who was leading one of the functions that I was on, and we had a hiccup with a client, and I said, well, why don't we just go in and explain the situation and, you know, share that there was, you know, a challenge on our side. And the reaction from her was, well, we're not going to show our weakness. We can't, you know, we don't want to be that clear and that transparent.
And as you asked that question, I think for women who were becoming executives, you know, 20 years ago, I think they were maybe seeking to be more like the male colleagues around them who weren't vulnerable, and didn't want to be straightforward about errors.
I've always felt like, probably through my upbringing and being an oldest child and taking accountability for my actions, I learned that being honest about mistakes and being really vulnerable actually got you to resolution a lot more quickly. And so I've always embraced that, but I do think it has been not something that I've observed in others with the same level of comfort over the years as I am starting to see now.
Charles (43:48):
I think you're absolutely right, society has never supported that perspective of male leadership and what it's supposed to be. And I think as the evidence mounts that young men in particular are struggling, probably perhaps more than any other individual demographic group at the moment, I guess it depends how you measure it, but certainly they're struggling a lot more than I think we've traditionally expected or seen. Hopefully one good thing that comes out of that is the ability for men, young men and men to become and be allowed themselves to be more vulnerable in terms of how they lead, because they've grown up in a different kind of environment.
Your job is, you don't have to tell, I don't have to tell you, incredibly complex, very, you know, very visible, high-profile. How do you make time for yourself? How do you take care of yourself in the middle of all of that?
Jill Cress (44:32):
Especially in tax season, it is a lot. We have a total addressable market of 150 million Americans who must take an action by April 15th, and we are in it as we're recording in April.
And so I think again, it goes back to that intentionality and really being thoughtful. I try to look, well at the year ahead and map out how I want to spend my time. But certainly in a moment like tax season, to really look at the quarter ahead. It's hard because there are so many demands on my time with my team, with the demands of the business. It's that we run a retail operation of, you know, close to 9,000 locations across the US that are open. We try to get out in the field and inspire the teams and learn and watch real customer interactions with our tax pros and season.
And so as I map out the quarter ahead, particularly in a busy quarter, it's about protecting time. I try to actually maintain some of the things that I learned in COVID, which was, you know, block out time for me to work out. I know I'm much more energized and just more clearheaded when I get a workout in, in the morning. And so I'm pretty regimented about putting that on the calendar and blocking time.
I'm actually just back from a weekend in Amsterdam. I took my 80-year-old mother who wanted to visit my niece, who's studying abroad, and my daughter, to Amsterdam for a girl's weekend. I knew that was going to be a big time commitment, albeit it was just a long weekend, but I blocked that out, planned for it, you know, had the mechanisms in place so that I could take that time and be present.
And so again, I think it's about being intentional, understanding that life is not always balanced, it's not 50-50, but we have to, you know, work really hard at moments, and then when we want to ensure that we can take the time for ourselves, that we're thoughtful and planful and we get ahead of it and don't let us, don't let it sneak up on us.
Charles (46:34):
So good. Obviously as we get older, we hope we get wiser. If you could go back and talk to the version of yourself that was just entering the job market for the first time, based on what you know now, what advice would you give her?
Jill Cress (46:46):
Well, I mentioned my relationship with being in charge versus nurturing those that were in my charge. And I think that is a big lesson learned. And I've got a daughter who's 25, and living and working in New York City, and I try to inspire some of this in her and her friends, which is, it's not only about the wins that you get on the board, but it's about how you get them. And I think that balance of, you know, what you do, but how you do it is really, really important. I still have to remind myself to slow down to speed up. I can see a path to resolution very clearly in most situations. And my younger self was just so focused on driving towards the win, towards the resolution, and I moved so fast to get things done and to get problems solved, that I didn't always appreciate the context of those that were around me that needed to be on that journey as I was rushing towards resolution.
And even now I get really excited by change and transformation, and as we start to do that work, I just want to go, I just want to get it done. And I really have to remind myself of those lessons where I moved too quickly and I didn't bring people on the journey. I don't think I always get it right, but I'm much more aware of that.
And so I think the summary of that is, it's not only about the wins, it's about how you show up, it's about how you build rapport and trust with those who are on the journey with you, and taking the time to reflect. I do, we do a lot of after-action reviews, and I do them for myself as well. You know, how did I intend – I just had a meeting with some members of the senior leadership team that I'm on and I had wished I had shown up differently. And so I did a quick reflection by my own, I mean, on my own after that meeting to kind of say, what was the context of the meeting, what went well, what did I learn? And I think it's really about being intentional, about taking the time to be thoughtful.
Charles (48:53):
I haven't asked this of anybody else, so I'm curious to see how you respond. If I was to ask you, what are the three things that are most critical to unlocking creativity in the people that work for you, what would you say those were?
Jill Cress (49:04):
The first is empowering them. I have had the priv–as I said to you, I thought I would be this incredible creative and saw a life of me working at an advertising agency, and realized that I'm much more of a strategist than a creative human. And so when I find myself in the presence of incredible creative talent, it's really about empowering them and allowing them to challenge my beliefs, going into something.
The second one is something that we've already discussed, which is resilience, and the importance, particularly in the modern marketing era, of balancing incredible creative ambition and instincts with data. I wouldn't say the data always overrides a great creative instinct.
And that gets me to my third piece, which is taking risks, and still even as we balance the art and science of what we're doing to take big swings. And as I do that we've taken some big swings at H&R Block to re-energize this heritage brand. And when we take risks, it's ensuring that my team knows that I have their back and that we're in it together as we take a risk. So empowering teams, encouraging people to be resilient, and yet still pushing to take big, bold swings and take those risks.
Charles (50:26):
I haven't done this for while, so let me see if, let me see how this goes. I used to offer people on the podcast three observations about why I thought they were such successful and effective leaders. So here are the three things that I would offer you.
One, I think you've clearly defined success for yourself, both professionally and personally.
Two, you bring a ton of intention to that, now that you're clear about what it is you're trying to achieve.
And then three, I think your self-awareness, which I think in many cases it's, a lot of it is instinctive, but I think clearly you're also prepared to be open to the input of others, to be self-critical, to be self analytical. Those three things in concert, I think, are really powerful.
And I'm going to offer you a fourth one. And this is a brief coaching moment. There is no chance in my, from my perspective, that you are anything other than extraordinarily creative. And I find it interesting because I had Morgan Flatley on here, the CMO of McDonald's maybe a year ago, and she said the same thing to me – “I'm not creative,” – and I said the same thing to her.
I think you are profoundly creative, perhaps you just express it in ways other than cereal box covers. But I really want to thank you for coming on the show today. It's been an absolute pleasure getting to know you, and I wish you nothing but luck and success going forward, and I am amazed that you were able to find the time in the middle of tax season. So I thank you for that, as well.
Jill Cress (51:45):
Thank you so much, Charles. What a gift to have you wrap up this beautiful conversation with those observations. Thank you for synthesizing those and for sharing those with me.
And I do feel creative and I think my team would tell you that I try to bring that creative energy, so thank you for inspiring me to continue to lean into that. This was a really delightful hour in an otherwise very busy day. Thank you.
Charles (52:10):
You’re very welcome. Thank you.
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If you'd like to know more about our work with the leaders of highly creative and innovative businesses, go to fearlesscreativeleadership.com. There, you'll also find the audio and the transcript of every episode. Or, go to our YouTube channel for the video of our most recent conversations.
Fearless is produced by Podshop. Sarah Pardoe is the show's producer and handles all guest inquiries. You can reach her at sarah@fearlesscreativeleadership.com.
And thanks for listening.
