How to Have a Hard Conversation, Respectful Hard Conversations

Transcript

Peter: I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

And we’re finding our way

Peter: navigating the opportunities and challenges of design and design leadership.

Jesse: On today’s show Kaaren Hanson, chief design officer for Chase offers her perspective on what she had to learn and unlearn on the way to the C-suite, how the leadership challenge changes as you move up, and creating design teams that leave a lasting impact on their organizations.

Peter: Hi, Kaaren, thanks for joining us. I’ve been working with you now for couple of years, almost a few years in a couple of different contexts, and I’ve seen how you are leading these sizable teams, particularly inside a couple of banks, and Jesse and I are pursuing a thread right now, which is What does it mean to be a true design executive?

There’s a lot of people with design leadership roles and titles, but there’s not a lot of people who are operating at an altitude that I would consider errr… Being a real executive. And, and you’re definitely one, given the size and scope and scale of, of the operations that you’re responsible for. You’re currently the chief design officer at Chase.

Is that right? Am I getting that right?

Kaaren: Yep.

Defining the role of Chief Design Officer

Peter: Okay. So what, what is that role? What does it even mean to be a chief design officer at Chase? What do you, what, what are the responsibilities? What do you do? How are you held accountable?

Kaaren: Yeah, those are good questions. So, you know, it’s interesting ’cause I think about this as the role evolves over time. So right now, what I’ve really been focused on is: first, how do we create a truly strong and robust design team? One that has strong leadership, one that has strong craft. One that is appropriately resourced. And one that is integrated into the business yet is also able to go up an altitude, so they– we can look at the end-to-end experience.

So that’s been a big push of mine for probably the last year and a quarter or so. And I’ve been there for about a year and a quarter. And just in that time, for example, we’ve grown from about 300 people on our team to about 800 today will be about 850 by the end of the year.

And by the end of the next year, we’re gonna be about a thousand. Which is a lot of growth. Um, so you can imagine I was spending a ton of my time hiring, but also a ton of my time working with leaders across the business, including, like, the CEO of consumer bank or the CEO of connected commerce or the CEO of wealth management, to ensure that design is sitting at their table, and that the operating mechanisms are supportive of us being customer- focused, customer- first and really starting to hold a bar.

The other area that I’ve been focused on is metrics. So any executive knows like metrics fricking matter, right? You manage what you can measure and we can measure customer experience. We’ve all been doing this for years. Sometimes just more systematically than others. So one of the first things that I did when I joined was to connect with our data science team and to really work with them, they are very excited about customer experience metrics, and they were thrilled that someone else was excited about them and championing them.

And so as you just need two different voices in the org to really make something happen more quickly. And so we aligned on three key metrics that we’re using for our customer experience. And then it was all about how do we make sure every single team has customer experience metrics that ladder to the bigger OKRs of the company.

So for example, one of the OKRs that we have is Net Promoter Score of at least 70, right, which is a, a reasonably high bar. And then we can look at well, what impacts that net promoter score and some very basic areas. Customer success rates, right? If you’re not successful, you’re unlikely to be very happy, right? It seems super obvious. We can easily empower teams to go after that success rate.

We’re using something called a customer experience gap. This is something the research team started before I joined. And essentially what it does is the lead researcher, lead designer, lead product manager, do a heuristic evaluation of the five most common tasks. And they note all of the gaps that are present. And then we figure out, What severity are they, one to five. Five actually prevents you from accomplishing your task in some cases. And one is more like, you know, padding this size, that size. And so once we’ve got those in board, then it’s about how do we start to change the way that the company views our products?

So now I’ve been working with the people who operate the bank to make sure these customer experience metrics are part of the business reviews. They’re part of the quarterly business reviews. The CEO is asking about them. They’re part of monthly updates. And this helps the teams to focus on them.

While at the same time, we’re really building this muscle of strong design-research-content, et cetera, that is able to help the teams on the ground become much more customer focused and rigorous in that way. And then at the same time, what I’ve started to do in the last three to six months is focus on how our design, product, engineering, and data working together.

And toward that end, we’ve been bringing in Silicon Valley Product Group. They do a really good job really helping teams to understand that together, they are collectively there to understand the customer problem, to solve, to figure out how the heck they’re gonna measure if they made any difference, and to just go fast.

So I’m looking at it as you know, there’s this system that’s in place at Chase. And my job is to figure out how to use whatever judo moves I can to make it a system, you know, that supports the customer and creates conditions in which our teams can do the best work of their lives. And when I think about our teams, our teams are not our design team. Our teams are our product managers, engineers, data, and design.

Peter: So you’re, you’ve clearly thought about this, ’cause ’cause you had these four bullet points ready to go: team building relationships, metrics, product management. You’ve been a reflective leader. I’m wondering when you stepped into the role, did you know that’s what the job was? Is there a, are you working from a playbook or had you so, so, so you, so you’re, you’re shaking your head uh, which the, audience wouldn’t be able to see.

So how did you, what, what– did you have a playbook coming in? What did that look like? And then how did you unpack that these were the four kind of initiatives to engage in? And it sounds like in roughly this order, like how did that come about?

Kaaren: I mean, well, like, you know, anytime you start a new job, your first thing to do is to just listen and learn, right? And to figure out what’s going really well. What are the points that you can really shine and amplify, right? Like those CX gaps, huge point of light, all you have to do is help amplify it, right?

And then also what’s not working as well. And what doesn’t make sense. And then, you know, I took a lot of notes and I thought about, wait, what’s going on? Where’s this? And I thought, okay, which of these could I make progress on quickly versus more slowly?

I have tried a lot of different things, some of which were taken up like this, and some of which were not. So those customer experience metrics, that was a huge surprise to me how quickly it happened. I thought it would take two to three years. So I got started and I was like, all right, we’re gonna go, we’re gonna try this. And literally, yeah, within six months it was present in 70% of the dashboards that teams were working towards, like blew my mind.

I couldn’t believe how quickly this company moved. If I had my plan, I would’ve said I was gonna do that for the next three years. So that was a nice surprise. There’s some other things though, that we’re still working on, like the ratios, the ratios of designers to product managers, to engineers. They’re not where we should be.

And I’m trying to hire as fast I can, right. While still holding a high bar for talent. And I am not making enough of a dent on these ratios. Right. And so that is something maybe I thought would happen more quickly and it’s happening more slowly because we continue to hire all over the place.

And so, you know, so I, I think a part of it is also just seeing, well, where is the organization? What is going to get traction, right? There are probably 10 levers to pull that will make a difference. Let’s try one. If the org is ready to go with it, awesome. If they’re not ready yet, that’s okay. We got nine others. And so I’m very, yeah, I don’t necessarily have a playbook, but I do feel very strongly, the first job as a design leader coming in is to create a strong, robust team. Because if your team isn’t robust, there’s no way you can push for change.

Jesse: Mm-hmm , I’m curious about where they were when you started, what was their approach or attitude toward design when you came to be the face of design to the leadership there?

Kaaren: Yeah, I think it’s hard when you have organizations of this size, because it’s so, it’s so variable depending upon where you are, and depending upon the people. I will say what really impresses me at this company is the people are incredibly smart, but they’re also so darn open. And in fact, when I first joined, I was like, really? Are people really this nice? Like, hmm, is this just an act? You know, like when am I gonna learn that it’s not true. And I still haven’t learned that it’s not true, right? Which is astonishing.

So really smart people open to trying new things. Maybe they just under didn’t understand the rationale for why this mattered. So a lot of what I’m trying to do is articulate the rationale for why I’m doing something and why the team is doing something.

And one of the trainings we’ve brought in, we’ve brought in two really important trainings for the design team, meaning design, research, content strategy, et cetera. But one of them is Articulating Design Rationale with Tom Greever, right? And what that’s all about is, how do we help our team to better articulate why they’re doing something and why they think it’s important? Because usually if people have the same information, they come to the same conclusion, right? It just helps the overall broader team operate more seamlessly.

And the second one is Facilitative Leadership. A woman named Wendy Castleman has been helping us with that. And it’s really about how do we help everybody on the team drive alignment if there isn’t alignment and particularly that alignment on the customer, right? And again, like we’re getting better in pockets, you know, it’s faster in pockets, but overall it’s just a foundational skills we expect everybody to have. And sometimes I’ll talk to people and they’ll say, wait, I thought that was product management’s job. And I’m like, yeah, it is. And if the team you’re on, isn’t aligned, well, you go fix it, right? And it is so important. That’s why everybody needs to do it.

The need for prioritization

Peter: You mentioned going your team growing from 300 to 800. Was that real– was that a realization that had occurred before you joined and, and they wanted to bring you in as part of this expansion, or was that part of your listening tour? Where, in looking around and reflecting, you’re like, wait a moment, I see one of– a way forward is we need to grow the team in order to address the challenges that I’m hearing about.

Kaaren: I would say it’s yes, and. So I think when I joined my charge was to grow us from like 300 to 500. Right. Which was sizeable. And then it became clear that, you know, that wasn’t nearly enough. And now, by the way, I’m the one that’s saying we’re not growing to more… by more than a thousand. Like we’re not, and I’m getting all of this pressure, yeah, but we want 60 more people and I’m like, get in line. Because everybody wants 60 more people and, and no! Right?

So, but then that forces the question of, well, then what’s the prioritization? And I will say I have, I’ve had two amazing bosses since I’ve been there. One hired me and she’s such a high flyer that after five months she became the CEO of Card and also the CEO of Connected Commerce. So, the biggest business and the most strategic business, which just gives you a sense for how freaking smart she is. So she’s lovely. And then my second boss used to be the chief technology officer, and now he’s in charge of product, design, data, et cetera.

And and he has been fabulous because I said to him, look, one of the issues we’re running into is what is the prioritization? What is the prioritization across these lines of business? Because everybody thinks their stuff is most important. So he has been driving some really tough conversations about what actually is most important. Because we don’t have unlimited resources. Even if we have money, it doesn’t mean we have unlimited resources. And so again, like he’s been hugely helpful. And the amount– the amount of impact that had on me and the team was tremendous.

And we also, you know, he’s also been incredibly helpful just to make sure that we are having every design leader that sits within a line of business sits at that CEO table, right? One design leader per, which is critical.

And, though, I’ll tell you this, just ’cause you get a design leader up there, then they have to figure out how to act when they’re there. So there is someone I was hiring and you know, we were doing some feedback. I give everybody feedback after 90 days or. And some of the feedback was, Hey, you need to step up more and have a louder voice. And this person said, “Okay. Yeah. I mean, like I’ve always been fighting. We need to get at the table, but I’ve never actually been at the table. So like, so, so now that I’m there, I kinda don’t know what I’m doing.” And I’m like, that’s okay, well, figure it out together.

Stop fighting, start partnering

Peter: So many design leaders, and you’ve probably had this experience as well, you know, your posture is one of fighting, it’s fighting for your team. It’s fighting to be understood. It’s fighting for resources. It’s, there’s, there’s a kind of struggle that happens.

And, but, when you get to be at this, what I think of as true executive level, if you come across as a fighter, you’re… That, that becomes a problem. Yeah.

Kaaren: You are junior. If you come across as a fighter, if you’re not looking at the bigger team, if you’re not looking at the bigger business and if you’re not respecting, like, you know what? You are the best player in that role. So, you know, just let me know what you come to. I’m gonna run with it. I trust you.

Peter: So, how do you, what is that coaching that you’re providing to help people kind of flip from that fighter mindset into… So I have the Patrick Lencioni book behind me and he talks about “the first team,” right? And, and to reflect like, as a design executive, your first team, isn’t your design org, it’s these other executives that you’re now partnered with. What have you done to help people kind of shift that thinking?

Kaaren: Well, you know, it’s funny ’cause one of the things that I do deliberately is I’ll ask people, you know, who is it that you’re …whatever, whatever tool you use, right? So in our case we use Symphony, but great. Who are you Symphony-ing with the most, right? And if it’s not your product, eng, and data partner, then what are you doing? Right? Then you’re spending the wrong amount of time with them.

And so I think that there are some little ways that you can reflect on how are you spending your time. I think the other bit is to figure out… what I realized is I often ask the exact same types of questions in every room that I’m in, and I’m asking those questions because usually other people are not, and they’re very important, right, to me. And I believe they’re important to the success of us as a bigger company.

And so what I’ll often do is I’ll coach the people that report to me, I’ll be like, okay, so let’s go through this business. Let’s talk about this business. What comes to mind? What questions do you have? What do you think might be important? What might not be being talked about? Let’s get your point of view on that. Let me help you to strengthen your point of view on that. You can bounce it off of me and then you’re ready to go, right? So it’s almost like you do the practice before you get in the room, because sometimes people feel like they’re a little bit caught flatfooted as like, well, Is this really important? Should I really say this? Is it really my place to say this? You know, what is my role? And the other thing I would say also that I got, which was great coaching from an executive coach many, many years ago, is that you don’t know where the edges are until you run into ’em.

Jesse: Mm.

Kaaren: Right? So have a point of view on things that maybe you are like, well, that’s not really about design stuff, yeah. But you better have a point of view and someone will give you feedback if they’re like, can you stop talking about security? ‘Cause you know nothing about security. Like, okay, fair.

Jesse: Mm-hmm.

Kaaren: But I think a lot of it is just, is just prepping and then being kind to yourself and realizing that, you know, it’s an experiment.

How to successfully make change

Jesse: I think a lot of leaders get caught up in that fighting mindset in part because they see it as necessary to what they see as their role in the organization, which is as change maker, driving the organization toward some different kind of culture and more innovative culture, more human-centered culture, more design-led culture.

What do you see as, as the role of design in making organizational change, and how do you navigate that… between making change in gentle ways that can be more successful versus digging in and fighting?

Kaaren: Yeah. So I think about it as, you know, I’m also, when I join a company, I look for points of light, right. Or goodness to highlight. And so you know, I’m always looking for a, wait, so who are the product managers that are really killing it? You know, that you guys are working with? Who are the engineers that are really killing it, which data people are really involved in the customer problem?

And then I make sure to highlight them and to bring them into, you know, broader presentations to the org or to leadership. So we’re really highlighting those points of light because a) it reinforces what they’re doing as well, and then b) it’s a model for other people.

And that way you’re not always telling people don’t do this, right? ‘Cause if you just say to somebody don’t do this, they don’t know what to do. That’s not helpful. It’s more helpful if you help me figure out what to do.

And then the other thing that I’m working on is, how do we pair people? So you’ve got a product manager with a designer that they’re working together so closely with that they really start to trust each other, right? And then it’s easier to move people along.

Now, the downside to this is it’s not a fast change, right. It takes time. On the other hand, it’s more likely to last, right? And I think if anybody tells you they’re gonna change in org like a year, they’re just absolute liars. Unless the org is like three people, you know, it’s just not gonna happen, right? ‘Cause we have such habits, and organizations have habits and then they all reinforce each other. And those operating mechanisms usually reinforce the old habits. And especially if you’re at a successful company, and Chase has been unbelievably successful for like over a hundred years, right?

And so yeah, we can get better, but we’re gonna do it by, by having people see that it’s more fun and more impactful as opposed to feeling like what they’re doing now doesn’t work.

The other thing is, I am not a fan of perfection. Like I don’t seek perfection. I know things aren’t gonna work. I know teams aren’t gonna move as fast as we’d like, you know, and that’s okay.

But what I don’t have a lot of patience for is you know, when people are rude about it or disrespectful. So there have been instances when I have heard about someone being disrespectful, and we’ve gone after that right away, ’cause it’s not okay. And part of it is going after and making sure that person gets clear feedback and that person’s not rewarded for it. But part of it is also helping our team to say, okay, I’m gonna have this hard conversation. It’s not okay for you to treat me like that, which can also be really scary for designers to do.

Jesse: Mm.

Kaaren: We actually just piloted a class on that Peter yesterday in Ohio.

Peter: A class on…

Kaaren: On hard

Peter: …respectful hard conversations.

Kaaren: Yeah. How to have a hard, how to say it to somebody, you know what, when you did this, it’s demotivating and it feels bad…

Jesse: mm-hmm

Kaaren: and I I’m sure your goal is not to have me be demotivated and feel bad. Yeah. So let’s talk about what’s going on.

Peter: Chase, you know, in some ways is a Wall Street banking firm. Not known for being a touchy-feely enterprise though, as you said, you’ve experienced a lot of niceness and…

Kaaren: Oh. So much kind people.

Peter: And kindness. And I do wonder how this language of, de-motivation, you know, like you could, you could imagine maybe in another company with a more, “suck it up, buttercup” mindset. Like, this is work, we’re all here to, to succeed and you know, I don’t have time to coddle you and your concerns. ‘Cause this is a, a newer way of approaching these types of interpersonal dynamics within a business to, to be a little vulnerable, to, to, to acknowledge feelings. I mean, business is a place where we’re often taught, historically, legacy, not to acknowledge emotions and feelings to focus on “it’s just business,” to focus on the problem at hand. And so maybe, maybe that I, this is a long way into the question, but maybe the question is around, how do we acknowledge and accept these are humans with feelings and emotions and motivations in this context in a way that doesn’t turn into one giant like therapy session, right? You also don’t want it to just kind of bog everything down.

Kaaren: Mm-hmm

Peter: But you don’t wanna ignore it. How, how have you managed that?

Kaaren: Well, and what I would say is, again, like it has to do with what is the culture that you’re joining and Chase has that good culture where people are valued, right? And so by and large, this is very much a part of how people operate. And what I’ve found is I dug into some of these issues sometimes it’s that the designer maybe approached it more as a fight, right? And then there was a fight back, that everybody felt bad and it was all a mess.

And so again, it’s part of how do we both change how we’re operating, right? And how do we have these conversations, but also recognize how might we approach it differently. But one of the things I find really helpful is there’s a woman named, uh, Teresa Amabile. She wrote a book about like I think it’s called the power of purpose and this was probably back about 10 years ago or so, but she was at Harvard and she did a whole bunch of research on organizations and people and what makes them effective. And essentially there are three things that matter.

It matters, do you have people that you feel good around that you trust. Right. Do you have a clear purpose that you care about? And then do you have evidence you’re making progress? And if you have those three things and you have to have all three of them, you’re gonna be pretty darn happy and pretty darn productive at work.

And so, you know, I think that people part is a big part of it. Are you being treated respectfully and whatnot, and then the purpose, it goes back to what is your company’s purpose and how are you living it? And so I work really hard to tie everything we do to our purpose, which is help people make the most of their money so they can make the most of their lives, right? Like I am happy to get up every day and go after that.

And then the progress again goes back to those CX metrics. So I also think a lot of framing about this is why we’re doing what we’re doing, but I will say that at Chase, you know, it is very much expected. There’s a high bar for people interacting with others. Well, and really operating in accordance to the values of the company as they get more senior. And in fact, they won’t get more senior if they’re not operating according to those values.

Now of course, anytime, a very big company or there’s some people that sneak through, of course, but not, not very often in my experience, in fact, almost never.

Jesse: I’m curious about some of your previous roles in design leadership before taking on this challenge at Chase and how they prepared you for this and maybe how they didn’t.

Kaaren: Hm. Good question. So what I would say is, you know, when I was at Intuit for the longest, I was there for almost 12 years and I worked very closely with Scott Cook, who was one of the founders. And I also worked with Brad Smith, who at the time was the CEO and, and a bunch of other people, and yeah, we went after design for delight and we went after upping the craft and we went after upping design leadership, right. And changing the ladder, so they went all the way to VP and I spent a lot of time on compensation and all that good stuff.

And you know, there were, there were cadre of us who got the crap beat out of us again and again and again and again, well, we tried things that failed and tried other things that failed and tried other things that failed, but eventually it succeeded.

And I feel like what I learned there was a lot about how do you stop talking and get people to do, right. So how do you make it easy for them to take action? And so that’s been a big part of how I look at the world.

Then I went to a startup and that was just a ton of fun. And there were like four designers and me and I got to do hands-on design, which I hadn’t done long time and it was exhilarating. It was great. And it was also chaotic ’cause startups are. And then, so I think from there, I just, I laughed the most I’ve ever laughed in my entire life. Like literally every day would just be busting out laughing. It was amazing.

And then I went to Facebook and what I learned at Facebook was really this relentless focus on a metric. And how, if you get teams that are super driven, focus on a metric, they will run fast. Now obviously there are downsides if all you’re doing is running fast towards a metric. And we can see those downsides all over the place. Right. But it really did teach me the power of metric. And I was astonished by how much time was spent, figuring out really what is the right metric that we’re going after.

So that was really interesting. And then when I went to Wells Fargo, you know, they’re under consent order and they were super candid with me that they were under a consent order when I went, I didn’t actually know what that meant. You know, it just like, you know, I, who knows? What it actually means is that there’s a whole bunch of scrutiny from regulatory perspective, which means that the amount of fun, impact you can have is very little, because almost all your resources are going to, you know, help with regulatory issues that need to be solved. Right. But I would say that at Wells Fargo, I learned more about the banking business. Right. And so I learned more what the lingo was and how that worked, which I think made it easier for me to go to Chase and step in quickly because I already understood the words people used.

And then it was more about what are the patterns that I’m seeing.

Jesse: Mm-hmm hm mm.

Kaaren: But I mean, honestly, like, I feel like throughout my career, I’ve been so lucky because I’ve worked with so many smart people that have taught me so much. And that really is, I think how you learn the most is just on the job.

Jesse: Yeah.

The leadership skills needed to develop

Peter: Reflecting on that and what you’ve learned and you, you just shared some, kind of bullet points or not bullet points, but, but experiences you’ve had that have kind of stepped you up, but I’m wondering, you know, what are things that you, in order to become an effective leader, what are the things you needed to work on?

What are the things that, that, that, that folks pointed out to you as like, Hey, this isn’t going so well, you might need to try a little bit less of this, a little bit more of that, whatever that was. And so, yeah. What are the things you needed to work on? And then what were those skills that you had to, to develop, to become an effective leader?

Kaaren: So, so I remember three things pretty clearly. So one is being transparent, right? So if you’re not transparent about what you’re doing and why you’re doing it, it’s easy for people to read all kinds of other things into what you’re doing. And they may assume you have nefarious intent. And so like having to be super transparent about what I’m doing and why it didn’t come naturally to me, because it’s so obvious to me what I’m doing and why, right? And, or maybe I’ll have said it once. And I just think, of course, everybody remembers, right? And they don’t. And so now I’ll often use words, I’ll be like, okay, right, “just to be transparent about what I’m doing,” right. I literally say that. And then I’ll unpack why I’m doing what I’m doing. And that has been incredibly helpful.

I think another item that I had to work on was judgment. So judgment is toxic. Like being judgmental is toxic. On the other hand, as someone who’s been in this field, we are incredibly critical of things. We are like, nobody is more critical. That’s our job is to be critical, right?

Jesse: Right.

Kaaren: But that’s not helpful when you’re working with other people, and you’re trying to drive change in an organization, because if you’re judgemental, it’s almost like you’re adding toxicity to relationship. So I’ve had to rein that way back. And I, I worked on that, I think for like five years before I felt like I had actually made enough difference, but now I’m, I feel like I’m pretty good at that. But it was a lot of hard work.

And then the third one was, you know, I still remember the first time I went into the CEO staff meeting and this was at Intuit. And this is way back when, when we, you know, Intuit was seen as really intuitive and such a good experience. And it turns out we weren’t and we had done some benchmarking.

And if you looked at the success rates of people using TurboTax versus using our competitors, or, you know, QuickBooks versus our competitors, or Quicken, whatever, we were basically maybe a little bit better, maybe a little bit worse, or maybe the same. And so I got to bring this data to the CEO staff meeting and, you know, my boss was there with me and he was like, okay, you know, here’s how it’s kind of gonna go. And I was like, okay, okay. Okay.

I was so focused on sharing the information that I wasn’t reading the signals around the room, because I think my brain was so overwhelmed that I couldn’t do both. And so it was interesting that when we then walked away, he was like, okay, well, the feedback for you is you talked a little bit too much. You didn’t listen quite enough to this person or this person. ‘Cause I thought my job was to share the information and yes, my job was to share the information, but I would’ve been even more effective if I had been listening in and navigating to where the conversation wanted to go.

And that’s not to say I did it terribly, like it was totally fine, but that’s where I could have been better. And so there’s always like what’s actually happening in the room versus what are you sharing, right? There’s just those different altitudes to be aware of in the context. And so that’s also something that I’ve, I’ve gotten much better at, and now it’s natural for me, but the first few times you’re in that situation, it’s not, ’cause you’re like, oh my God, what’s going on, I’m so nervous, you know?

And, and then I also remember just to make it better. So when I shared the data, they were like, that’s not right. We’re Intuit. And I was like, no, the data’s right.

Peter: The data’s the data. Yeah.

Kaaren: Right. Like, this is, this is real. Like, we’re not. So that was also this like awkward conversation. But it did prompt us to start to look at things more deeply, right. Which was great. And the other learning there is, you know, eventually when our CEO put together a tiger team for what’s beyond ease, right, I was a part of that tiger team, as were a couple of other people in the, in a couple general managers, the chief strategy officer. He did that in part, because he knew it had to come from everybody involved, which again goes back to, if you want everybody to solve the problem together, they’d all better understand the customer and the problem together all the way through solutions, right? So again, like, you know, he was teaching me so darned much, he wasn’t necessarily being explicit that he was teaching me, but I just learned a ton.

Coaching your leaders

Jesse: Yeah. Speaking of teaching, I wonder what role that plays in your sense of your relationship to the leaders underneath you in the organization, as well as, you know, the whole downstream design organization.

Kaaren: So one of the things I do spend time focusing on is I will help our designers think about how they’re gonna share their information. Right. And so I will spend time saying, okay, you’re gonna share this. And I think this is gonna be a story that we’re gonna wanna share. It has to be really good. So I’ll be like, great, why don’t you share it with me? Okay. Here’s some feedback. This seems most important. This, you know, this is one of your most salient points. How do you make it more clear? And we’ll kind of go through stuff, do it again, come back tomorrow. Right. And so I’m very positive, but I want them to walk through it because once they learn how to do this, well, they’ll do it well again and again, or at least better again and again. And they’ll have those short stories and snippets that they can share with their executives in the elevator.

Jesse: Mm-hmm

Kaaren: Right. And so I feel like that’s something really important and useful.

And then I make sure the organization is sharing across the board. So we’ve been doing some teardowns, you know, of various experiences. And we’ve been sharing those with the broader team, not the 800-person team, but like the, you know, 80-person leaders, so that everybody starts to have the same expectations for what they’re going to teach with their teams. Right.

And then the work that Peter’s been helping us with on career pathways has been incredibly important because this, again, helps you to understand here’s what I need to go from here to here, right. But it really is all about how are we all upleveling our game together and doing it in a way that’s transparent enough that the rest of the org will, you know, kind of pull us in as opposed to trying to push us away, okay.

Jesse: One of the things that I hear about from people who are in executive leadership roles is that there’s a qualitative difference in the job when the people that you are managing are also themselves managers, when you have people who have pretty large chunks of their own responsibility and their own needs for autonomy associated with that. And you know, the potential for competition and you know, friction across the various teams. And I’m curious about what you see as the as the difference between managing leaders versus managing individual contributors or design talent.

Kaaren: Yeah. It’s interesting. So, I mean, I guess I think about it in some ways it’s sort of the same. It’s just that they’re gonna play different roles. I’ve hired, like, a number of very, very, very senior people who have run large orgs already themselves. And that’s great because I can plug ’em in with a CEO and they’re gonna figure out what the hell is going on.

And they’re gonna say, here’s what we need and we’re just gonna make it happen. Right. And so they have enough space that they can do that, but they’re also aligned to the broader goals of the organization. So we can do it across, right, more synchronously, which is going to be more helpful for the overall org.

Jesse: How do you drive that alignment?

Kaaren: How do I drive that alignment? Well, it’s, we bring it back to, we’re creating one experience,

Jesse: Mmm…

Kaaren: Like there’s, whatever, 800 people, it’s one freaking experience. And so we start to look at, you know, what are, what is the experience as you go across these 25 products in one journey.

Jesse: Mm-hmm

Kaaren: And yes, it might touch Michelle’s team and it might touch Ryan’s team and it might touch Will’s team. So let’s look at it all together. And the good news is I’ve hired people that are senior enough that they they don’t have a big ego in that. Right. They’re like, great, let’s figure out how to make this happen.

And there’s enough work to do that. You know, you can take that on. Oh, thank God, because I’ve got these 20 fires over here.

Jesse: Mm-hmm

Kaaren: And I do think that’s a difference is that when there’s a lot of meaty work, people get less territorial. It’s when there’s only one bit of interesting work or like a handful of interesting work that everybody’s trying to get into the interesting work.

Jesse: Mmmm.

Kaaren: Right. And that’s when you have usually not good behaviors. And to be honest, I also hire for people that are focused on the bigger team.

Jesse: Mm-hmm

Kaaren: Yeah. But with individual contributors, I think it’s the same. You have to give them a meaty role that they’re likely to be successful at. You have to coach them to make sure that they are successful.

You have to make sure they’ve got the connection to the other people that they’re, you know, dependent upon. Right. Or they’re going to benefit from. And you also have to assume that these are smart people and they’re gonna figure out how to work together well, and if they’re not, well, then you deal with it. Right. And like, that’s cool.

The “Vision” Thing

Peter: You, you mentioned one experience, and it made me wonder, when it comes to design leadership, the word vision is a common word in that context and… but vision means different things at different altitudes of, of an organization. And so what does it mean for you? To have, to hold, to communicate a vision. What’s your responsibility around that idea of a vision? I’ll leave it at that.

Kaaren: Yeah. So I would say that it is my responsibility to drive a shared vision around the experiences that we want our customers to have. That doesn’t mean it’s like a picture of a thing that we’re gonna build, ’cause that thing may shift over time, but it’s much more around, you know, it should be concrete, it should be measurable. It should be aspirational. Right.

And so what is that vision? That vision is that our customers are, you know, I mean, I just adopt and go, “making the most of their money so they can make the most of their lives.” Okay. What does that mean? What does that look like? So that means like we have a Net Promoter Score of 70 plus, that means that we have measurable benefits that we know customers are getting more benefit from us than they are from others. So how are we gonna make that true? Right.

And then what does it mean when we’re starting to operate more by journeys as opposed to by products? Right. So if you look at a customer journey, you often would cross many quote unquote products, which sometimes are maybe features. And so that is what we need to start to look at. I feel like a lot of the work though has been done and sometimes I think leaders make mistakes by thinking I have to make this all my own. I have to do it all my own. And it’s like, no, no, no. What’s good you can just run with, and go do that.

Jesse: Mm-hmm.

Peter: It sounds like you entered into an environment that was a little more mature. I think a lot of design leaders find themselves in a less mature environment where they’re– what’s expected of them is to be a visionary…

Kaaren: mm-hmm

Peter: which the people around them don’t even know exactly what they mean by that, but they, they have some vision of Jony Ive and, and brilliance.

Kaaren: Yes, but they would kick Jony Ive out, if you were in that, in the organization they’re in, right?

Peter: Right. But they don’t know that. Right. And so kind of navigating that, but, but to the, kind of, to this vision point, you mentioned the NPS of 70, you mentioned earlier that change doesn’t happen in a year, right. That, that you recognize that there’s, there’s a longevity to this.

Managing and Leading when Things Keep Changing

Peter: How does that square? So one of the things I’ve been poking at, I actually wrote a blog post about recently, what I called the management carousel. Right. Because people come in and out of organizations every two or three years, it’s pretty typical. I did a poll of designers and found out on average designers have a manager for about a year.

Some, they might have two or three managers in a year, some maybe longer, you know, when you were at Intuit, you mentioned 12 years. And you mentioned that like, there was a relentlessness you needed to bring in order to see some of these ideas through. And because you were there so long, you could kind of do that.

What does it mean to make change in a context, in a reality where things are shifting so much?

Kaaren: Well, and that’s where those operating mechanisms count so damn much. Right. ‘Cause it doesn’t matter, who’s in position. If you’re having to report out on your CX metrics and the CEO is gonna read it, even if the CEO changes that helps to hold it all together. Right. So I feel like that’s

Peter: Incept these…

variables, these…

Kaaren: Yes!

That is like, that is like this secret judo move, right? You can build the best damn design team in the world. If you’re not changing the operating mechanisms, it doesn’t matter. And it’s not gonna last long. And the worst thing that happens if you’re a design leader is you do something, you walk away, in six months, it’s gone.

Jesse: Right.

Kaaren: Because that meant you didn’t build it for durability, but to build it for durability, you have to get into the operations of the company and companies have like a, heartbeat…

Jesse: Right.

Kaaren: … which goes back to, what are the expectations for designers? What are the expectations for product managers? How are we bonusing people on this stuff? Like, those are all the operating mechanisms you have to, you have to infiltrate.

And at, Intuit, we, we did it. I didn’t have the idea to do it, but fortunately someone was like, oh, you need to bring this into blah, blah, blah, and so we did, you know, but it was like our fast path program, our rising star program. Right. All of a sudden we indoctrinated them with design thinking and that became, here’s how successful people operate here, which again, helped, you know, change the culture and make it last.

And I actually saw Scott Cook at someone’s retirement party, not that long ago. And he was, I’ve been out of Intuit since ah, seven years or so. And he was like, we’re still doing design for delight. We’re still training every new hire on it. Do you wanna come? And you know, it was really sweet and thoughtful. Right. And I was like, oh, maybe but you know, it was great ’cause it had lasted that long because it was, it was in the DNA of the company.

Jesse: Mm-hmm.

Kaaren: And that’s what takes a while. And that’s where you’re persistent. And you say, well, can it work in here? Can I get in here? Can I get in here? Okay. These doors all shut, but this one’s open. I’m going in here. And then another couple, you know, months, I’m gonna go back to these three, ’cause by the way, the characters might have changed in there. Or I might have new information that might make me more, you know, compelling.

Your job is to make your partners successful

Jesse: So you’re describing this kind of constant cycle of relationship building and almost like relationship renewal as you’re re-engaging with people with a new perspective, as the context has shifted around around you. What advice would you have for people who are getting into that partnership-building routine for the first time?

Kaaren: I think part of it is also that…. I mean, you guys know this too, ’cause once you’ve been around long enough, when, early on you think, oh, that person just doesn’t like me or oh, that person just doesn’t get it, and later on, you know, you’re like, you know what, maybe their kid is in the hospital. Maybe their dog vomited on their shoe this morning. Maybe they’re late to a flight. But maybe this just isn’t the right time. And that’s cool. Right.

And so it doesn’t matter if I go back in three months, not at all. Right. And how can I help them in the meantime? And again, you take the assumption that you assume positive intent is so important. They’re trying to do the best they can. Right. They’re working with what they got. If you’re asking them to take a risk and operate in a new way, but they’re under the same damn deadline, it’s not a good time for them.

Jesse: Mm mm-hmm.

Kaaren: If it is, you’re there to make them so darn successful. And that’s something, actually, Joe O’Sullivan was really good at when we were at Intuit.

He and I have worked together a few places now. And you know, When we started the innovation catalyst, the role of the innovation catalyst was to make whatever team they joined incredibly successful. It was not about let’s get them to do X practice or Y practice, but it was like, we are gonna make them more successful than they ever would’ve been without us.

And as part of that, we’re gonna use some different tools because it’s gonna make them more successful. Right. But it was all about making them successful. And so if we go into it from that mentality, my job is to make you more successful. And I may not even say that explicitly, but that is absolutely how I operate.

So you say, oh, thank God. Kaaren came by. That’s the win. Right. And then if I start to ask you like, oh, Hey, what would you think about tracking these metrics? You’ll probably be like, yeah, okay, fine. Yeah. I’ll give it a try for her, ’cause she helped me do this thing really quick and fast.

How to hit the ground running

Kaaren: The other thing that I’ll say that was interesting for me, that I suspect people may run into when they join a new company is…. This happened when I was, when I joined Chase, is we were launching something, something was coming out and it wasn’t good. And I had been there like six weeks and my boss said to me, what do you think of this? And I was like, eh, yeah. It’s, it’s not very good. Right. Something hard to say that when you’ve been there six weeks, but I was like, yeah, you know, it could be better.

And she’s like, yeah. So fix it. And I was like, oh fuck. And so, sorry, language.

Peter: It’s all good.

Kaaren: And so, and so I was like, okay, what am I gonna do? And I thought I’m gonna do my best facilitative leadership. And so I found all the characters that were involved. Right. And I made sure that we all were saying the same stuff. Right.

And like, well, what’s the value and how are proud of this? Are we? And what about this? And you know, then I pushed on some of the assumptions, one of the assumptions is that it had to go out in June because, you know, name drop person wanted it. And then we came up, people got comfortable with the idea of, well, no, we’ll do it in August because it’s better ship something good in August instead to ship something not so great in June.

And the conversation was had with that senior leader and the senior leader said, great. So there had been all of this concern that this particular woman wanted something by a certain date. She didn’t care. And if you ask an executive, would you rather ship something kind of not, not that good or two months later, would you rather ship something pretty damn good. It, 90% of the time, they’re gonna say pretty damn good.

Jesse: Yeah.

Kaaren: Right. You just have to figure out how to share that in a way that people understand, but there’s a lot of that type of navigation, right? Of how do you align people? How do you help them see what you are seeing? Sometimes they have information that you don’t know,

Jesse: Mm.

Kaaren: and which case do you, you change your mind, too? It’s really fun though. It’s so fun.

Peter: You mentioned facilitative leadership as, as kind of the, the means by which you helped realize this change. And led me to wonder, is facilitative leadership kind of distinct to design, because of the posture that design has in organizations. Often a synthetic function bringing kind of all kinds of different things together and trying to make sense of it. Like, I’m looking to unpack this idea of design and facilitation, ’cause you see it over and over again, not just facilitative leadership, you mentioned design thinking and I’m assuming kind of back at Intuit, the D the design for delight program, there was a lot of facilitation going on. Is that something specific to design? Should other functions be also facilitating or is it not authentic to their postures? And it is authentic to ours. I’m I’m curious if you’ve, your, just your thoughts on, on facilitation as a thing designers do, but not others.

Kaaren: I mean, I think there are certain practices, like being transparent, focus on outcomes, facilitation. Those are just good practices as a person. Right. And I think about this, like I use those on my kids all the time. Right? So like one of my, one of my sons, he was you know, he was not spending much time doing his homework, just put it that way.

And I was like, you know, that’s it, I’m like, you don’t get more A’s than B’s, you’re not mountain biking. And he was like, what? He’s like, you’re terrible. You’re one of those moms that only cares about achievement and, you know, blah, blah, blah, blah, blah, blah, blah. And I was like, well, you know, if you were working three hours a day, and you were not doing well fine, but you’re not at that point. So we’ll talk about it later.

But it was just really interesting that I, you know, he had this conversation, I was like, I’m managing you to outcomes, not activities. Right. And he was like, oh my God. Right. And then, you know, at other times I have been like, okay, so what do you think is the right path? Here’s what I see, what do you see? Right. And so then we’ll kind of come together. And I find it incredibly helpful. So when I think about us teaching these skills to people, it shouldn’t just be design, but we’re not teaching them for people to be successful at work only. Right. It’s just to be successful in life. And I just, it made me super happy later on like two years later, my son was like, I was so mad at you, but you know, he’s like, that was actually probably the right call. I was like, wow. I’m like writing that on a piece of paper. You are signing it. It’s like. Okay. It’s going in a vault.

Peter: Yeah.

Kaaren: The one time.

Jesse: Entered into the record.

Kaaren: But I, but I do think design has a special ability to do that because we are customer-focused, because we are human-focused and a lot of that facilitation is being attuned to your partners and really figuring out, well, wait, what do you know? What do you think? What if we did this? How might we align? And that becomes almost like a, it was like a game to play, right? Like, oh, did that work? Oh, that didn’t work. Okay. Let’s try this play.

Jesse: Yeah, well that gets me wondering, what are the design skills that you feel you are still using in your role these days?

Kaaren: Wow. Gosh. It’s hard to know. What’s a design skill and what’s not a design skill, right?

Jesse: Yeah, your call.

Kaaren: Mean, holy cow Peter, I’m looking at you with our career pathways. What’s a design skill versus not? I mean, I think about it more as I’m trying to design the organization, I’m trying to design the system. Right?

So trying to design the design organization for sure. Trying to design the broader organization and how we interact, and then trying to design the system and the mechanisms that they support doing great customer centered work. So I feel like that’s what I’m designing now.

Jesse: Hmm.

Kaaren: And then I am a, I’m a social psychologist by training.

And so there are also some, you know, I was telling Peter this, there are some, you know, techniques in social psychology, you learn. So for example, basics, and I tell these to people all the time. If you send an email to 40 people, you’re gonna get very little response. If you send 40 individual emails to people with their name on it, you are gonna get a much higher response. And so when I need feedback on someone for midyear reviews, I write individual emails to everybody. Right. Because I know I’m gonna get greater response. So, you know, am, am I using that training? Yeah, I am.

Jesse: Mm-hmm.

Peter: So one of the things I’ve learned when it comes to organization design, at least the way I approach it, is that I tap into my background as an information architect to think about the design of these systems and structures. And I’m wondering if, like, just curious kind of whether it’s the social psychology or, as you started in user experience, what are those design habits or patterns that you practiced many years ago, I won’t say how many, um, that, that you are now, that you are now reapplying, as you’re thinking about organizations, right? Because it’s different to draw a set of wire, you know, draw, draw a flow diagram and a set of wire frames for a software interaction than it is to be thinking about org charts and business models and connecting people to strategy or whatever.

Kaaren: Yeah.

Bringing your design practice to your leadership practice

Peter: But there might be some, some things that you’re bringing forward, just in terms of your practice, if you even think of it as a practice,

Kaaren: it’s interesting, I think a lot about what is most prominent, what is most important, what is second most important and how are we making what’s most important, most prominent and how are we getting rid of the noise? Right. That would just be distracting. So I do think a lot…

Peter: almost like a visual hierarchy or something..

Kaaren: It’s a visual hierarchy. It’s kind of in my head, but yeah. It’s like, okay, wait, what really matters here? What doesn’t —get fricking rid of it. Right. And then I also think about, okay, well, if we’re gonna do, you know over time, we’re going to unveil more, right? What is most important to unveil now? then do progressive disclosure, right. And at what point do we do progressively disclose versus not? Right.

So I do think a lot about that. But I also think it’s interesting ’cause you guys know this. I mean, when you’ve been in the design world for 20 some years, it’s just how you see the world, too. Right. So I, I don’t know how I would operate if I didn’t see the world this way.

Peter: In terms of how you see the world, I wonder… you’re working now with peers who probably see the world differently…

Kaaren: Oh yeah.

Peter: And how cognizant are you of your different way of seeing the world from them? How cognizant do you find them to be? How reflective of their own like, like when you get, you know, this is kind of, I, and I’m, I’m thinking about this, especially as you are in the position you’re in, right?

You’re the lead designer, the people around you are not designers. How are you, how are you understanding them and their perspectives? How are they understanding you and your perspective and how are you making sure that you’re working well together instead of talking past each other or somehow at odds.

Kaaren: Well, you know, one of the things I, I think about when I’m meeting people and I’m working with them, I’m like, wait, what’s most important to them, right? Like I’m literally noting that and I’ll be like, oh, this language has come up twice. Now this is clearly an important construct through which they’re viewing the world. Right.

And so I’ll note that, so that I understand where they’re coming from. And then it also helps me better understand where I’m coming from, which again goes back to, I ask a lot of the same fricking questions, right? Like, oh, what’s the impact to the customer? How are we gonna know what the impact of the customer is. Right. You know, what is success gonna look like?

You know, like, so it’s basic questions that we ask again and again and again, and when I ask those questions, it also gives clues to everybody as to where I’m coming from. And then they start to expect me to ask it, right. Or if someone else asks it, I let ’em, I’ll be like, I love that you ask that about the customer. Right. And I’m always, not always, I try to, to give praise to things that I see that I really like again, ’cause then people tend to do them more.

Jesse: So you are part of a r ising wave of design leaders who have been elevated to this executive level to engage, in these conversations, bringing that design lens or mindset…

Kaaren: Yeah.

Jesse: …that you’ve developed over the course of your career to these conversations. And there are other people just like you…

Kaaren: Mm-hmm…

Jesse: …who have similarly been elevated all over the world.

Now, what do you think that represents in terms of the opportunity for design as a whole? Now that we have design leaders engaging at this strategic level.

Kaaren: I mean, I think it’s never been a better time to be in this field. Like I can’t, I mean, I cannot believe how lucky we are to be in here. I have no qualms at all, when I talk to people about being, oh, you should totally go into this field, blah, blah, blah, blah, blah, blah, blah. It’s fun. You know, it’s impactful, you have great purpose. And the growth is tremendous, right? And so lucky for us.

But I also feel like now we have a real responsibility to actually make these experiences much better and much better for all people. Right. And so, you know, I, I feel like we’re very lucky, but frankly, there’s also a tremendous responsibility for those of us who are in these positions, because if we don’t do a good job, that can harm people that come behind us for years.

Jesse: Hmm.

Kaaren: Right. And you’ve seen that, you’ve seen companies where someone’s come in and they’ve burned out and they’ve, you know, burned some bridges and all of a sudden design is nothing.

Jesse: Yeah. Well, I am seeing a lot of leaders these days who are the ones who came in after all of that went down and they are having to repair those relationships and rebuild the credibility of design inside these organizations in some cases.

Kaaren: Yeah. Yeah. Which is why, I think, a lot of our job because we’re not as understood as engineering is, is about helping to teach people and understand what we do and what we’re about. And frankly, that we’re on the same team, right. Because I think sometimes when people don’t succeed it’s because it is more of an us-them mentality. Right. Where it’s like, no, no, it’s just us.

Jesse: Hmm.

Making a space for design in a business+tech context

Peter: So for design, design, as a practice, right, is, is different than engineering and different than businessing, right? Design is generative and creative and can be even playful. Whereas, you know, stereotypically at least, you know, a bank is going to be risk-averse and quantitative and metrics-driven and analytical, and those can be seen to be at odds.

And I’m wondering what you’ve done inside organizations to allow that space for that generativity and the uncertainty that you need for design to actually have its full impact, but that kind of runs contrary to maybe the existing business culture of certainty and, and kind of analytical rigor or whatever. That, like, how do, how do we hold these two things in one space and allow both to thrive?

Kaaren: Well, and I think that’s a really good question. And so I have, I have two parts to that.

One is that I think of it as a portfolio approach. So if you come in and you say, we’re just gonna do everything big, wide open space, and we’re gonna slow everything down, you are gonna fail. Right. But you can look at your portfolio and be like, okay, when we look at this portfolio of initiatives, these we’re just gonna put points on the board, move ’em out.

These two seem ripe for really having a bigger impact by being much more focused on discovery and definition and whatnot. And so we’re gonna put our points here. Hope like hell at least one of them works, right. And if it doesn’t whatever, but like at least one of the two, and then that’s a story we can share.

So I think about it as a portfolio approach across the board and that way you’re hedging your bets.

The other thing that I found really helpful, and even in terms of with our data partners, is talking a lot about how there’s inspiration and there’s rigor, and inspiration can come from anywhere, right? It can come from your own experience. It can come from, you know, looking out at the universe. It can come from big data sets, right? Big data sets can give you ideas for inspiration. It literally comes from anywhere.

And so part of this is, as we’re doing these broader explorations, we’re looking for inspiration and then you go into the phase where, okay, now let’s be a rigorous. Now let’s test the hell out of it. This is a hypothesis. Is it true? I don’t know. Let’s find out. Right. And so that also, I think gives people comfort because I think when there is discomfort, it’s like, oh my God, these designers, they just want nine months, they’re gonna go do this stuff, they’re gonna make a bunch of slides, it’s not gonna ever work. And then we’re gonna waste some more time. You know, we did that five years ago. Right?

So you run into those stories. And this way it’s much more balanced and the notion of like, yeah, and then we’re gonna test the hell out of those ideas and see which ones have legs just gives people comfort.

And again, you’re doing it on a few as opposed to on everything. And then over time you start to do it more, which goes back again to this is a long-term play building. An effective design org is not gonna happen in a year, but every year we’re gonna get more and more and more and more effective. And the way I measure my success is do I have a happy and engaged team, are Net Promoter Scores getting up to the seventies, you know, are the leaders being credible and are they respected? Right.

And then are the processes changing in a way that they will durably reinforce these conditions that are needed to create great experiences.

And like, those are the only four types of metrics that matter. And every day that’s what I’m thinking about. And that’s what I hold my leaders accountable. I’m like here, what, how are you doing on people? How are you doing on partners? How are you doing a process? And how are you doing on products and experiences? It makes it simple. And then it’s just hard to actually do it.

Peter: Easy to say.

Kaaren: Yeah, but it also makes it easy to be transparent. Right. So when I hire in a new leader to sit at CEO table, have a conversation with CEO and I’ll be like, great. Let’s talk about your expectations for this person coming in.

Here are my expectations. This is generally what I would expect of them in the first 60 days. Here’s what I’d expect them to be within six months. What do you think? And they’ll be like, oh, okay. And they’ll read through. And they’ll be like, yeah, that makes sense. I’ll be like, okay, so here’s how we’re gonna measure their success. And that way we’re aligned from the beginning. Right.

Because the worst thing I could do to this person that I hire is to stick ’em on a CEO table, have the CEO think they’re gonna do something other than what they’re actually gonna do. Right. ‘Cause that’s just gonna create awkward conversations and unhappiness. Yeah. So a lot of it is just thinking about how do we set up the leaders’ experiences so that they’re set up for success. And that’s my job. My job is to set up people on my team for success.

Navigating idealism and pragmatism

Peter: A theme that I think might be emerging for me in design leadership. Jesse and I, we have themes that emerge from conversations that we have. And one that’s emerging for me in the last few months is, the balance of, or navigating, idealism and pragmatism. I think a lot of designers get into this work because there’s an idealistic sense of making the world a better place through understanding our users and delivering them amazing experiences.

And then as they become leaders, inevitably they get, they hit some walls and then they have to figure out a pragmatic… how to be a pragmatist towards that goal. And some fail somehow, or that might be strong, but have real struggles figuring out how to be both at the same time. Yeah. I’m wondering what has your experience been trying to navigate idealism and pragmatism?

Kaaren: Again, I think it depends upon the context in which you’re in. Like there was a leader, Ginny Lee, who’s lovely. She was at Intuit, and then she went to the Khan Academy and now she’s retired. But she was all on board with saying, look, if it doesn’t make people proud, we’re not shipping it. Right. And so she would ask the team, are you proud of what we would release to customers?

And if people on the team were like, well, no, just wait until you’re proud. So there are gonna be some leaders that are more willing to try that out. And then our job is to make d arn sure that those teams are incredibly successful. Right. So I feel like I’m always looking for opportunities and then you go, and again, we’re working with a lot of different people in a lot of different areas.

So if we’re idealistic on everything, we’re gonna get nowhere. But if we find a few choice areas, yeah. Then we can do it. And if we find out our results are not very good as a result of being idealistic, well, we better be ready to say, yeah, and that didn’t work.

Jesse: Mm-hmm.

Kaaren: That’s cool. You know, not everything works, but you have to be confident enough to say that. Right. And sometimes I think that designers get stuck in feeling like they have to say it’s working, even if it’s not, because so much effort was put towards it, or they start to blame, oh, well, this would’ve been great, except the engineering team, blah, blah, blah, blah, blah. And it’s like, you’re all one team. Didn’t work. Move on.

If you’re going into design leadership, like, you know, your, your ass is gonna get kicked periodically, you’re just gonna dust yourself off. You’re just gonna keep going. Right. I mean, like that is reality. So if you feel like you’re alone, if you feel like you screwed up yeah. You probably did. Yeah. You probably are. You know, like, and, and that’s okay. Right. You just, you just get up and you just dust yourself off and you just keep trying and you try something else ’cause whatever you did, didn’t work. Right. And that’s okay.

Managing the loneliness of leadership

Kaaren: I had a, a CEO one point and he was great. And he talked about how, you know, it was kind of lonesome to be him, right. Because he’s a CEO and who the heck does he talk to? And if you’re the design leader, well, it’s kind of lonesome for you too, because who do you talk to? I, I don’t know. I talked to my cats sometimes. Right. I don’t know. Um, And uh, I shouldn’t say that.

I mean, I actually talked to a bunch of people that are lovely. People like Daniela Jorge. I’m not sure if you’ve spoken with her, but I stay touch with Daniela and Sara Khoury, and a whole bunch of others.

But it is interesting that, you know, he would say that he’d get the crap beat out of him by the board. And then, you know, his staff would be angry with him and that managers would be yet mad at him for whatever reason. And he had all these problems and legal’d be on him. And, you know, he’d wake up in the morning and he’d, he’d look in the mirror and he’d comb his hair and he’d say, hello, handsome. And then he’d go to work. ‘Cause someone had to give him positive feedback and so.

Peter: We all need the attaboy.

Kaaren: We do. And so, you know, there are gonna be times that it’s like the best job in the world and there are gonna be times that it’s so damn hard. And then I just remember that story and I’m like, yeah, guess what? It’s part of the job. And it’s also part of how we get smarter and better and, and frankly have more empathy.

Peter: You referred to a network of people outside of the organization that you’re connected with. And I’m wondering how, how you think about how as that leader, where you are lonely, yes, you need to kind of psych yourself up or, or, or get yourself into a good spot, but almost practically, what are the means by which, what, what, what have you put around yourself to kind of help you maintain your positivity, maintain your energy, maintain that, that engagement and passion that can very easily be leeched away if you’re feeling stuck and alone on an island where nobody understands you.

Kaaren: Okay. I’d say first. So like just myself, I’m relentlessly optimistic, right? Like probably like more optimistic than I should be. So that’s like not a…

Peter: Just like a personality trait?

Kaaren: Exactly. Just a personality trait, like whatever. But I think also, you know, I mean, I do reach out, you know, I was just, I literally was just saying Daniela, ’cause I text with her, you know, a couple times a month you know, just about, oh, do you have five minutes?

Yeah, I’ve got five minutes. What about this? Right. And I’ve got a, you know, a small group of other, probably four other people that I do that with as well. And it’s just helpful to have somebody else who is in the exact same damn position, you know, is either dealing with it today or dealt with it three months ago or is gonna deal with it three months from now.

And it’s so darn useful. Right. And again, that makes you feel like, well, actually you’re not alone. We’re all just doing the same thing, in different companies, but we’re really doing by and large the same thing. We’re just doing it with different players in different contexts and we have different leverage to pull.

Jesse: Kaaren. Thank you so much. This has been great.

Kaaren: Oh, it was so much fun. Thank you for having me. And Peter, I finally got to meet Jesse and hang out with him almost as much as I hung out with you, today.

Peter: How public are you on the internets and interwebs? How can people follow you, engage with you? Are you, do you, are you writing or like what’s how, how would you like people to…

Kaaren: oh, that’s good

Peter: think about connecting with you in a professional fashion?

Kaaren: Well, they should connect with me on LinkedIn, and they should just ping me questions anytime they have them. And I love that, you know, I think that I’ve just been trying to get my head around, what is this organization? Right. And I’ve been trying to ground myself and I’ve been feeling like yeah, I purposely stopped speaking because I just had to get my act together.

And now that I feel like we’re getting stronger and more robust and I’m gonna be able to have more time to spend writing and being out there which I’m really looking forward to.

Peter: Excellent.

Kaaren: Yeah. But ping me on LinkedIn. That’s probably the easiest. Yes. I might get back to you quickly. It might be a little while.

Peter: Well, thank you so much for, for sharing your, your experiences with us.

Kaaren: A pleasure. All right. Take care. Bye bye.

Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s @peterme and I’m @JJG. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too.

As always, thanks for everything you do for all of us. And thanks so much for listening.