Transforming Legacy Systems in Insurance Industry

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: Navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership,

Jesse: On today’s show, in a conversation recorded in November 2023, Christina Goldschmidt reflects on her first 60 days on the job as the newly appointed VP of product design for the music industry giant Warner Music Group. She offers thoughts on getting up to speed and finding early success as an incoming leader, profiling your stakeholders as if they were users, the leadership power of personal vulnerability.

Peter: Christina. Thank you so much for joining us.

Christina: Thanks so much for having me. I’m so happy to be here.

Peter: As, usual for us want to start out just by getting a better sense of who you are and what you’re up to. I know you’re in a new role, so if you could just share kind of your professional affiliation and, what are you doing now?

Christina: Yeah. Yeah. Thanks. So I have been in the field of digital design for over 25 years and that’s been many twists and turns. And I just started a new role as the VP of Product Design at Warner Music Group. And I’m just a few days shy of hitting my 60 day mark And so it’s a very, very interesting time to have a chat about that.

And my role there is that I lead product design, which is both user experience design and visual design, but also working to build out our user research practice. Also, our brand new content design team, design operations, and making sure that we are just a fully functioning working product design team.

Also adding things like design systems, things like that.

Starting a new role

Peter: It sounds like you’re introducing a lot of. new elements into the organization. Was that something that they knew they needed and were looking for the leader to bring it? Or was that part of a conversation you were having with them as they were talking to you? Like, oh, this is, this is what I would want to do if you were to bring me in.

How did that conversation go?

Christina: Yeah. So one of the things that’s really interesting is that my entire hiring cycle was three weeks and I’ve never actually had a job, I think that was that quick, except for maybe 25 years ago. And so that was a real testament to them knowing a lot of what they wanted in a leader, but also trusting in me to be able to come in and diagnose everything that needed to happen.

And so we would have conversations along the way of maybe we need this, maybe we need that. So, halfway through the conversation saying, Oh, you know, we don’t have content here, so think about that. You know, that would be the kind of aspect of the conversation, but larger things like design systems the larger structure of how to build out research, adding design operations, those are things that they’re trusting me to really bring, diagnose and decide how to structure.

Peter: What group are you in? Are you reporting up to a product leader or are you in a different kind of organization?

Christina: Yeah. So, because Warner Music Group is a music company, I report to the president of technology. And so it’s very different than, say, my last job at Etsy, where we were a technology company and I used to report to the chief product officer. I’m still one away from the CEO, but I am in this interesting new space where our entire organization is the technology organization.

So now my immediate peers are engineering, product management, and something called product solutions, which is really our liaisons with the various labels and business, business partners.

Jesse: So you described this three-week sprint of a hiring cycle and, that just feels like this whirlwind where you have absolutely no time to prepare, no time to even really get your head around how you want to show up, who you want to be, who you need to engage with, how you want to engage.

It feels like you had to hit the ground running and make it up as you went along. How did you start figuring out how to engage this brand new organization? A very different kind of a problem, different kind of context than you were used to.

Christina: Well, I think that hiring process was sort of a, in a sense, a preview of what the job might be in the first year.

Jesse: In a good way, I hope.

Christina: In all honesty, right? Like, it’s a two-way street every single time you’re in a hiring process. And the concept is, is that it’s a startup within an enterprise company. And so being able to actually intelligently show up in a super fast hiring process, diagnose what they need so that I can show myself in my best light to them, shows that I can have basically a bunch of things thrown at me every single day and be able to diagnose that and move it forward.

It’s not for everyone, we’ll just say that, right? This was not a role that was for everyone. Yeah.

Peter: You know, one thing I’ve noticed, just following you on LinkedIn, is, and you mentioned it earlier, expanding the organization. Something else I also know about you is that you went and got an MBA at one point, so you know how to do math in spreadsheet form.

Christina: Yes, Yes, I do.

Peter: I’m sure your PowerPoint game is on point. But I’m wondering, what, if any, business case did you have to make around expanding your team? Was that something they had done the work to realize there’s some broader expansion and, we’ve already assumed it, or were you needing to argue for, may not be the right language, but help them understand the potential and opportunity and, thus do business casing. Like, how did you free up the resources for headcount?

Christina: When you’re undertaking something like this, that’s the first thing you ask. Especially in such a short cycle you want to understand how open they are to design, how much they value it, what they think the role of design will be and therefore my role. I was actually very happy and pleased to hear right out of the bat that they were already planning and had already started to put budgets in, that were very appropriate for things that I would want to need. And so I did not have to actually make the business case. When I got in the door, there was definitely finagling, horse trading, and things like that. I will say that immediately from day one, I had to prove value, and have to make sure that I’m not going to lose those heads, right?

But at least they understood and they value design and they see how important it is to build a really great product arm and that they had actually already allocated significant amount of head count to design. And that they left it up to me as to how to carve out that headcount.

Jesse: I think one of the biggest challenges for leaders who are new to an organization, trying to figure out how to deliver some kind of short term value, is the fact that they just don’t know anything yet. They don’t know anything about the context. They don’t know anything about what people really care about. They don’t know what their priorities ought to be, really, in terms of value delivery. And so I wonder, how did you go about learning the landscape in order to figure out where you could start delivering value right away?

Christina: Hmm. Yeah, so let’s be clear I don’t know anything. But I know just enough to be a little bit dangerous, right? One of the things that’s interesting about Warner is that their fiscal year starts in October. Planning was basically close to being done when I was walking in the door. And so, that was a really important time for me to understand where things were really important.

By knowing what their major focus areas were, and getting involved to help them make a better PowerPoint, to present that to the executive leadership team to the CEO so that we could convey that story, I was able to then say, Okay, I now understand this because I’ve helped to better visualize it and help us tell that story better

Jesse: Hmm.

Christina: And then understanding what that is, talking more deeply of… what does this mean, and having basically weekly prioritization conversations every week to say, I could choose to do 1000 things this week. Which do we think are the top three, five that matter this week?

And that kind of triage is really important.

Jesse: Who are you having those conversations with. Whose opinions really matter here?

Christina: Yeah, so it happens with my boss, the president of technology, and you know, I’m four in a box, right, with my other three peers. And it, oddly, is not happening all together. I’m having them as sort of more one-off conversations than triangulating it myself.

But it actually is pretty consistent. They’re just nuances that come with it when you have it as individual conversations. And I actually think in our environment, it’s working very well because it allows me to be that filter as opposed to us trying to work very hard to get in a consensus mode, which, If I was trying to facilitate that, it would take us much longer than if I’m taking in quick information and then choosing it for myself.

Jesse: Hmm.

Peter: The speed with which they moved suggested they had a, and I think you said this, like a pretty decent idea of what it was they wanted. And I’m wondering, what was it about you that landed? What were those qualities or characteristics, and then perhaps related, how clear was your mandate upon arrival? Or is that something you’re having to tell them? Sometimes we hear from leaders who, their first three months is to figure out what their mandate should be. And other times, when they come in, there’s a pretty clear idea of what’s expected of them.

Christina: Yeah. I can only report what they’ve parroted back to me, right? So there could be other things that I don’t know about why and how they chose me. But the question that they asked me for my case study was to present to the most complex project I’ve ever worked on. And they also were like, and it doesn’t matter if it’s like song and dance beautiful, just show up with some work.

That was their instructions. That’s a very different sort of prep sheet than other jobs that I’ve seen and things like that. And I think that that really shows to me sort of how they think and what they value.

Telling a transformation story

Christina: And what I gathered was a massive transformation story that I had done previously in the insurance space, where I had taken extremely legacy systems, you know, things that are on green screens, things that look like they’re Windows 98, variety of legacy old systems where there are three different systems, systems that had stories about people needing over a year to get trained on how to use them, systems like that, and showing them how relatively quickly was able to diagnose, was able to prove that the system that my team was working on was actually going to be better without having A/B testing or statistical results. That I could actually leverage both quant and qual in a much smaller in-house pool as opposed to, what I might do at Etsy, which is A/B test very quickly at scale and be able to prove that with metrics and be able to make something that is simple, usable, beautiful out of something that was previously none of those things, you know, cause I think I have that idea that because we all have really stunning cell phones in our pockets now, right?

These mobile devices, that no matter how deep into enterprise software or workhorse software that you’re in, everyone has a mental model of really beautiful, simple, elegant interface design now. And so there’s no reason for any tool to not take the, like, deep, really thoughtful customer experience into mind there. I think that philosophy also really was exciting for them, too, that I also had had experience bringing that kind of consumer facing interface design and simplified user experience to actually enterprise-based software and it was for, actually, business improvement, right? Things like reducing training, improving time on task, that is also always about making the experience better, making tangible metrics better, being able to prove that value.

I think that that was a big part of that story for me. And that I was able to show them that case study that they were like, Oh, this is exactly our problem here. You get it and you’ve done it. After, you know, one 30-minute conversation with the hiring leader and one, 30-minute conversation with the in-house recruiter. So being able to pull that out, I think made it look like a good fit.

And then the other thing that I think was helpful was that they were signaling that this is a hands-on role and you know, my last job was very much at scale. Very much where I was primarily doing operations and improving the way my team worked. Yes, I would have regular weekly reviews. Yes, I would think about the holistic customer experience, but my job was not day to day in our products and making them better and leading designers day to day.

I had an entire, you know, hierarchy of managers and directors underneath me who I deeply trusted in order to do that on a day to day basis. Here we’re a much smaller organization, where my ability to still give day to day design decisions is actually important. My ability to still be able to do that and to show that I could still do that, learn and talk about the work and not be just at a pure operations level, I think was also helpful.

And, to understand, I think, part of the larger value proposition to go to your second question They didn’t fully articulate this to me, but I could see it immediately when I walked in the door, is that you know, there are three major, like, music companies out there, right?

And we’re one of those, and it’s a great time in the music industry where there’s all this growth and really learning how to leverage streaming to make the business better. It’s a time for great innovation. But not all of the experiences are really, truly human centric and don’t actually meet the mental models of the users or the customers that use them.

And so to be able to actually bring innovation, to bring the tools of the trade of helping the team use more modern design techniques, really upping their game, so that we can look at design as a center of innovation, so that we are more competitive, that we can produce software that will gain us more business, that kind of aspect is definitely an aspect of my job. That it will be a competitive differentiator that the experiences that we make and the software that we ship will actually help us improve our business.

What does it mean to be ‘hands-on’?

Jesse: So you raised the question in here of how close you actually get to the work as part of your role. And for a lot of the people that I talk to, stepping from a highly leveraged operational oversight kind of a role into a role where you are closer to the design work, you’re kind of sleeves rolled up in it, for a lot of people that raises this fear that they’re not actually progressing as leaders, that this represents some sort of backsliding toward craft and away from leverage. And so I wonder what it was like for you to step back into craft and how that has affected how you see yourself as a leader.

Christina: I think one of the things that design leaders have is craft and that it’s our, not to reuse this term again, but it is our competitive differentiation as a field.

Jesse: Mm.

Christina: That there’s lots of overlap with the people that we work with every day, right? There’s this Venn diagram of, oh, we can set strategy together. Oh, we can determine technical feasibility together. But the craft is the thing that we do and that we own. And so as a leader, when I had an organization at scale, I never actually hired managers who did not come from craft. You know, there is a school of design leaders who are wonderful and design managers who are wonderful and are great managers.

But there can be a lack of credibility with them if they actually have never done the work themselves. And so that was my philosophy why that was so important. The reality is, is that it’s like our center and our core of understanding the work and how the work gets done and making sure that our teams are always able to do that work.

So I will say I do not make comps in Figma myself. I am in Figma looking at Figma, you know, whiteboarding with the team, putting notes in Figma. I’m not pushing the pixels, but it is still the craft of what is the best way to craft this experience? How do we understand the user? Things like that.

So just to let people know where my edges are. And then to get back to your question, I actually missed it.

Jesse: Mm hmm.

Christina: You know, and sometimes this is a blessing and a curse for some people, right? That, you know, the thing that you’re good at and then you miss it. And then it’s very comfortable to be able to go back to it.

And it’s about achieving the right amount of balance. I am definitely doing a massive operational overhaul here. I get to do that here, right. I get to think about how I’m making an organization at scale, building all of those things in and what’s going to be the right thing for us, for the long haul and to set the team up for true success, make a great culture, etc, etc.

But having a good balance with the craft is really important. And being able to say, I can walk into the CEO’s office and really defend that what we’re doing is right, and be able to talk about it probably within my first 30 days of, I know that we are going to be able to make a competitively different solution for this because I’ve already been in the sessions where we have come up with it, makes you feel really good that you’re not in those first 30 days being like, what am I going to do? What kind of value am I going to add?

It gives you fuel to then keep going, to keep growing, to keep being able to do more. So that’s how I kind of look at it. It’s almost like it’s low hanging fruit in a way. Don’t get me wrong. It’s hard. So it’s not that kind of low hanging fruit, but it’s like relying on something that you know.

Peter: You’re a relatively new leader, things moved quickly. I’m curious about the team you’ve inherited. That could put the team that you’ve inherited feeling anxious, uncertain, hopeful, all kinds of things.

Christina: Yes, I’m sure they felt all of those things. Yeah.

Enabling psychological safety

Peter: Well, and, based on our conversations and things that you’ve presented in the past, I get the sense that you’re attuned to the state of your team. And I’m wondering, as part of this first 90 days, how you’ve engaged them, what you’ve heard from them, and what are you doing to bring them along into this period of rapid change that you’re leading?

Christina: Yeah. So one of the things that’s interesting about the team is that they’ve already been undergoing this change for over six months now without me. And this is something that’s actually happened to me quite a bit, is that I come into roles where the position has been open longer. For some odd reason, the design team seems to have a lack of leadership.

And then the team is extra anxious because all of this change is happening around them. And they’re the one team without a leader. I don’t know if I’m attracted to those kinds of situations or what the correlation is with that, but that happens to me. So yeah, so a lot of this change has been happening prior to me joining.

So for about six or seven months, they’ve already been in it. What they’ve told me is actually having a leader has been helpful. And then one of the first things that I did was try to figure out how to actually bring them all together. ‘Cause some of them, though they’ve been there for multiple years, have never met each other in person.

You know, if you joined within the past three or four years, you’ve been working with people for a very long time. But because of the pandemic and then additional change, you’ve never met someone in person. For me, it’s like, I want to meet everyone. I want them to meet each other. I want to make sure that we’re starting to really build a culture of working together and having a culture of open critique so that we can move fast and really try and make great work together.

I brought the whole team together to New York and we did a design sprint for a week, and it was definitely a new way of working for a majority of them. But it was also fun, right, and that they could see we could do something quickly, if we did it together. Making sure that we had happy hour the very first night that everyone was together was really important. Most people are like, oh, I don’t want to have happy hour on a Monday, you know, I just got here. But, it’s important to make sure that people let off steam, have a good time, actually get to know each other, so that the hard parts of the rest of the week are less hard.

Peter: Of the things I think a lot about, and I’m wondering if it’s possible to accelerate, is your team’s sense of psychological safety, right? We know how important that is, particularly for designing UXers, in order to do their best work. And in moments of uncertainty and moments of change in certain corporate cultures it can be hard to feel that. And I’m wondering how specifically attentive you’ve been to that, and if you’ve got tools or, practices or behaviors or something you’re doing to try to bolster that?

Christina: Absolutely. I’m very attuned to it and actually have a couple of small techniques that I think anyone could follow or could try that I’ve been doing. So one is having a regular time for critique. That is not me-centered, but the team-centered. One, I bring work to that so that we can talk about the things that I’m involved in that they may not be involved in, so that they can actually know that I’m open to hearing things from them and getting input from them.

So that it’s okay, we’re just working together. That I think was really important. Things that I would share might not, again, be a beautiful comp, but it might be a strategy on something or it might be a flow on something or something like that. Or it might be an approach to something, but so that they can actually give me input.

And then allowing it to be a conversation where I ask other people’s opinions, where it’s not just my opinion. So though it’s a meeting that I set and that it’s a time where everyone makes sure that they have access to me, right now it’s three days a week. So every other day. So that there’s always reserved time on my calendar for them. They know they can always get me at that time.

I don’t know that it will stay at that, but right now that’s where we are. Other things are how I show up, in conversations and even in Slack, where I, make sure I’m deputizing people to have ownership over things.

Actually, the other day someone commented on it of, Oh, you replied to something and said, this person is the owner of this topic, which we know you were working on with them, but you gave it to them to own. And therefore you weren’t going to be a bottleneck, but it also showed a deep trust and it allowed everyone to know that I indeed trusted this person, trusted their ideas and just so happened that she was more on the junior side on the team.

So it also showed that it doesn’t matter what level you are, that if you’re showing up, doing great work, that that’s what matters here. So you can be your best selves no matter what.

Destigmatizing mental health

Christina: And then I would say another thing that I do is I try to create a safer environment for our entire organization. I’ve done it twice now, but we have town halls every two weeks across the entire technology organization. And I try destigmatizing mental health in those meetings, and so I will actively, vulnerably talk about my own mental health, and use situations where I have the floor, to what, I think, sometimes… they won’t be surprised about it anymore, but the first time I did it, very much surprised people.

Peter: Did they know? Cause you’ve been public about this. Was this part of the hiring process? Like, did some people know that this is something that you advocate for? Was that a side benefit of you being in this organization?

Christina: I think for them it’s a side benefit and it’s also like you do you sort of type thing, you know, like no one told me like, Oh, we want you to do that here, right? Where sometimes when I talk to people they’re like we really need that, you know, That wasn’t one of the main reasons, right?

But, we were having a conversation around trying to help people So, we’re moving very quickly. There’s so many things going on. And we’re also global. So we’re in multiple time zones. People were giving feedback that it feels very hard to have work-life balance because we work with people in London, we work with people in Los Angeles, and some people work with people even more further abroad than those locations, and so that leads to a mentality of being always on.

And so we were giving tips as senior leaders, setting out principles for how we don’t want that for everyone, and how we think about that, and things like that. And so the tip that I got to talk about was time shifting. And it just so happens that our office is near my old office from maybe ten-ish years ago.

And so my therapist that I have seen for a decade, her in-person office is now six blocks from my office now, and so what I was telling everyone is that, hey, on Tuesdays, you’re gonna see that I walk out the door right at five o’clock, and that I might come on later to check Slacks and whatnot, but don’t worry, I will be scheduling Slacks and I’ll be scheduling emails so that I’m not going to bother you, but the reason why I’m doing this is because now I can go to my therapist, my shrink, in person, and I, think there were probably gasps because I said, I go to my therapist.

So, you know, moments like that, where I just sort of tell people that this is a thing and that it’s okay and that it’s normal and it normalized that for the entire organization really helps to drive psychological safety for my team as well.

Jesse: I’d love to hear some more about the value you see in putting yourself out there in that way as a leader. And you know, for design leaders who might not yet get why that’s important or why that might be valuable. What is it for you?

Christina: Thank you for asking me that question. So I’ve actually done a lot of research in the healing space and I’m sure if people have seen any of my other talks, they’ll know that I talk pretty openly about my own healing journey from complex post traumatic stress disorder. And one of the things that I’ve learned in my research for that, and on my healing journey, is that if senior leaders are vulnerable, it makes it safer for anyone else to actually understand and have the tone set for them to know what’s acceptable and possible in their work environment.

That, for me, hit home so hard that, if I can share, maybe somebody else can feel just slightly more that who they are is acceptable, that they can take care of themselves and ask for help or seek the things that they need, that they don’t have to fear any issues or any retaliation around those topics because I’m out there talking about them and normalizing them, very often.

And also, I have found that when I make myself vulnerable, it makes me more relatable. I’m sure you’ve heard from other design leaders that it’s a very lonely job.

Jesse: Yeah.

Christina: And, one of the reasons why I think is because you lose some of the camaraderie that happens with other designers when you ascend to you know, the highest levels.

And so your entire career, you’ve been with other designers who are in the same boat as you, who understand you to a certain extent. And then when you graduate to be a design leader, design executive, now your peers are all cross functional. And your team treats you differently because you’re their leader, even if you yourself don’t feel differently.

And so when you share, it makes you more likely to have a personal relationship with those on your team because now they see you as a real human as opposed to just a leader. And so I actually find that it gives me something back, too, like it allows me to have more with the team.

Peter: And when you say with the team, I’m assuming you mean the team that you lead, your design and user experience team, because I’m wondering, somewhere, here it is, you know, I have my Patrick Lencioni, right? Five Dysfunctions of a Team. He talks about one’s first team, which is, that cross functional team.

And I’m wondering how your approach has lowered barriers, that might not be the right word, but has made you more accessible and made your cross functional peers more comfortable relating to you, in a way that allows you to feel less lonely, even if they’re not fellow designers, you’re all part of a team trying to move things forward for the business, and what impact has it had for you in those cross functional relationships?

Christina: It’s also extremely beneficial. I feel so connected and supported and helped by my cross functional peers. And I also think it’s because I’m willing to show up and say, Hey, this is who I am. I’m advocating for all of us, but also I need help. I’m willing to say those words. And, that exchange makes it so that we can be really real with each other, and then you can go so much deeper with someone and understand what they’re actually trying to achieve and get to a very win-win situation, because you now know that you’re working towards the same thing. You can connect on that deeper level. And so I think it’s been extremely beneficial for me to also do that.

Because I say things that they might need to hear. Or that they’re so happy I said because they were thinking them, but didn’t have the words to say them themselves. Things like that. And so it also makes it easier for them in a sense.

Peter: We’re approaching this as an unalloyed good, and I’m wondering though, if you’ve ever overshared, if you’ve been in contexts where it didn’t work, where it actually got a little blowback, either someone else wasn’t ready to be as open or as vulnerable, or in a certain corporate culture, it was just like that doesn’t work here or anything like that, or if it has always worked for you.

Christina: No, it hasn’t. I’ve really only been in this mode of sharing since 2020 and pandemic times, when it’s really been, you know, sort of dire for us as a society. And I have, in difficult environments, like I started to share more at Accenture. And that was actually a really interesting experiment for me, where I actually, was treated very well and very respectfully when I did share.

But previously at another job, multiple jobs ago, when I was very close with someone, that was, let’s say, someone higher in the food chain than myself, and had shared, I definitely felt that there was retaliation against me for sharing. And I definitely don’t think that I overshared, but it felt like just sharing and them knowing that about me put me in an extremely vulnerable position.

Ever since then, I’ve been extremely cautious and then also have tried to figure out how can I make this better for others. I’m also dyslexic, and so there’s a lot of conversation in neurodiversity circles about do you disclose, do you not disclose, and that’s actually a pretty also interesting one for a lot of people to talk about, too, where I’ve definitely met people who are in environments where they will not disclose because they know those environments will basically start to try and exit them out of their organizations.

Whereas for me and design, accessibility is half of our job sometimes. And so having the ability to talk about processing differently and how it helps me with my job actually is a benefit to me. So I also feel very privileged in that now I’m at a leadership level and have less fears about disclosure. That also I’m in a field where certain aspects of the things I disclose are actually pretty much always beneficial.

But it’s definitely, you know, I’m not going to tell everyone to just run out there and tell everybody everything, because I, I’ve seen it go poorly for me and for others, you know?

Jesse: It’s such an interesting cultural challenge, because as much safety as you might be able to create when people are interacting with you personally, that second order, that second degree of safety beyond you out into the larger organization, I think becomes the real challenge of actually encouraging other people to show up in similar ways.

So it’s not just about how people behave when you’re in the room. What do you do to encourage, not just vulnerability and psychological safety, but, leadership traits and leadership values in the leaders that you bring up within your organizations?

Stakeholder management

Christina: The best thing that I can do is help people become really good at stakeholder management because we can be the best leaders that we can possibly be, but if we can’t manage other relationships, whatever you’re doing internal to your team, can all, you know, can all go to hell, right? I didn’t actually plan to be in design when I was a child. I wanted to be an anthropologist.

Peter: Couldn’t hack it though, could ya? I have an anthropology degree.

Christina: Oh, amazing. So no, I wanted to use the Internet, you know, data viz on maps to do some more predictive modeling in the field. And in the mid 90s, it was like a no-go.

Peter: Now that’s how they find lost cities in the Amazon, but not then.

Christina: No! Yeah, definitely. It’s a whole new day. But really teaching people a design based framework for stakeholder management so that they can do it, and become studies of their partners, and other techniques in order to shore themselves up and understand the world and have decision making.

That, I think, is how you can help design leaders be prepared for the future and to be able to lead and set the right tone because they can, in a sense, defend themselves, and that they can move ahead and advance the right agendas. And I do have some elaborate frameworks for that. I don’t know if you want me to go into it.

Peter: Maybe, well I don’t know about elaborate, but, you know something that I end up talking a fair bit about is the need for designers to change their own mindset. Designers do more to constrain themselves than anyone else.

And part of it is thinking that the work stands on its own without any communication. And part of it is politics. Like you don’t advance any agenda without playing politics, and, you called it stakeholder management, I call it playing politics. They’re kind of the same thing. I mean, there’s different shades to it, right?

And so maybe this question then: How have you helped, because I’m sure you’ve had folks who have been resistant to that, right? What have you found helps others see the opportunity and the value of these more political approaches?

Jesse: How do you help designers get over themselves?

Peter: Sure.

Christina: Okay. I can actually answer it from that lens, Jesse. So, I’ll quickly talk about one of my frameworks and that is a proto-persona-based approach to stakeholder management. It is explaining to your team or the person, first thing is to manage towards outcomes. When someone comes to you and constantly says, I can’t get my ideas heard, I can’t do X, Y, and Z, I’m not being effective, nobody listens to me, blah, blah, blah, blah, blah, that’s the best right time to help someone have a design-based methodology to overcome that.

Other people will, you know, give people, conversations around executive presence, et cetera, et cetera. But I’m like, no, let me give you something a little bit more tactical to do, and I’m going to be a, little bit silly about it, but I basically talked to this designer, let’s say, and it’s best if it’s done at least in a group of three people, to figure out who their target is that they are trying to make change with or convince of something, and that they basically need to study them.

Sometimes I use the word stalk, but really it’s, try to get into their mindset and follow things like, what kind of questions do they repeatedly ask? What kind of data sources do they trust more than others? How do they make decisions on a regular basis? And actually catalog these things and make a little proto-persona about that person. And then to go into a role-playing exercise where there are at least three people doing three roles, and you have to do all three roles, where one person plays the target, one person plays the presenter, one person is a note taker, and you go through a scenario, and everyone is in a different format, right.

The note taker is actually really important because they can see the whole scene, and give more holistic feedback, but when you’re embodying the person and when you’re actually trying to talk about the thing to the person and doing that three times gives you enough practice, right, that you can actually start to think more like that person, have more empathy for that person and get muscle memory about how that person might react and therefore how you can help that person see your point of view. And it I think relates well to designers because it’s using things that they already use in just a way that actually serves them in a different way.

Peter: As you were talking, I found myself Googling “empathy map,” right? Like, many of us use empathy maps in our work. What would it be like to do that for our stakeholders? Not just for our users or customers.

Jesse: Yeah. Well, I regularly recommend to my clients that as they’re heading into big stakeholder meetings to write a user research protocol, exactly like you would for…

Christina: yes.

Jesse: … user analysis. You know, it’s the same thing.

Christina: That’s so great, Jesse. wonderful. I love that. Yeah. Yeah, and then of course I have more esoteric opportunities that not everyone’s open to, but, I definitely have another line of opportunity where you might look at the world through the lens of tarot cards, or try to access your subconscious through shaman—

Peter: I thought you were going to start talking ayahuasca…

Jesse: Different podcast, Peter.

Peter: ..it is called Finding Our Way, you know, going on that journey.

Shamanism as leadership practice

Christina: Yeah, shamanic journeying and breathwork though, breathwork is a completely natural version of psychedelic journeying. So…

Peter: is that something you do with stakeholders? Do you breath work with stakeholders or is that something that you teach people to do with themselves and it allows them to show up better, or is, is there a group aspect to it?

Christina: I teach people to do it with themselves or in a small group, not with stakeholders, so that they can actually get to know themselves and tap into their subconscious to understand a situation better and to learn how to move forward. It can be pretty helpful. It’s very similar to, I think, the psychology of traditional design thinking techniques, things like liminal spaces or things like systematic brainstorming techniques when you’re pushing two ideas together to get to a new idea. Having regular access to your subconscious, we normally use it for brainstorming, for innovation, but it can be really, really helpful if you have that window into there, if you’re actually trying to use it to solve problems dealing with people, dealing with business challenges. It can be really powerful if people know that they have access to that too.

Jesse: There are always interesting sort of cultural headwinds that we face when introducing techniques that maybe haven’t been covered yet in the Harvard Business Review.

Christina: Right, right.

Jesse: And I wonder about what it takes to lessen the fear of the unknown here for people, and help people embrace new frameworks, new ways of thinking about, and doing the job that they think they already understand how to do.

Christina: Yeah. So one, it definitely helps when I lead with like, oh, I’m,y You know, the design leader that has an MBA, and I like to back stuff up with data and things like that, that gives me a little bit more credibility.

Jesse: Mm hmm. Sure.

Christina: It’s a little helpful in that sense. But in a sense there are gateway drugs. Um,

Jesse: Uh huh.

Christina: Metaphorically, right? So you can have people think about things like relaxation techniques, with basic breath practices, or talk about meditation a lot, and not call it that we’re going to do breath work. You know, like you can sort of help people get into something.

But also what I like to do is, if I’m really trying to convince someone to try one of these techniques, is walk them through the larger landscape, show them how it fits into a larger design practice, how it is very similar to other techniques that they use, talk about the neuroscience and the psychology behind it, and try to say this is a technique you can use regardless of its origins and that If you want to give it a try, you can.

But the reality is that so many people are mystical-curious right now that it’s actually not that hard. So, when I was at Etsy and we saw all that sales data, all, like, huge trends were in New Age rituals and in, like, sometimes during the holidays, psychic readings and drawings would pop as, like, number one, number five product across the board.

Like, the number one selling product would be one of those items.

Jesse: Wow. So maybe there’s more cultural permission out there than leaders might think.

Christina: Exactly. Exactly.

Peter: We talked a little bit about playbooks and frameworks, but as you’re looking forward, and as you’re looking at now, it sounds like growing your organization and you’ve been inside scaling organizations, I’m assuming, you just came from a scaled organization and you’ve had a chance to like, I don’t know if step back is quite right, but you know, you’re operating currently with a smaller team, though you’re going to be growing it to some greater size.

And I’m wondering, what you’ve learned in your past that is maybe changing how you’re thinking about scale and growth this time around, how are you approaching this opportunity differently than you might have four or five years ago?

Christina: Oh, absolutely. Well, I’m like, I have a framework for everything.

Peter: Hey, Frameworks are my love language.

Christina: Yeah. So I, think what’s been great about being in scaled organizations and in scaling organizations is it has allowed me to try and make some sense of that. And so I do have a nine part framework of everywhere that I want to look and investigate, so that something, like, I know I can come into a very fast moving situation where I have to go quickly and start to make my playbook so that I know how to tackle things and move forward.

Peter: And not just simply be reactive, but that you have an agenda that you’re bringing to bear, even without all the information.

Christina: Absolutely, absolutely. it’s gonna have me do things like, make sure I am from day one ground in the business goals. And if I can’t figure that out, then I can’t set the tone for the rest of the aspects of the framework. And hopefully I am figuring out those business goals even in the hiring process so that I know what I’m getting myself into oftentimes.

And then trying to assess, basically, where I think the design org is and, I’m sure you guys talk about this as design maturity and things like that, but, what’s the overall approach of the design team that’s there, and how the larger company or organization as a whole reacts to it and values it and interacts with it.

And what might be needed in order to make a shift there to an ideal state or better or more ideal state? And then some of it is just the mechanics of given that sort of landscape, what’s the best kind of organizational model? Should we go after what’s the right kind of ratios regarding cross functional teams that is going to make us successful right now, making sure that those mechanics are in place very early.

So that if I haven’t gotten the head count, I know how to go get that head count or to fight for that head count. And then starting to think about the team itself, you know, looking at their career paths, career ladders, thinking about longevity, thinking about the transparency there that becomes really important because if your team doesn’t actually know where they are and where they can go, it also makes it harder to help move and shift them into different ways of working or into growth patterns.

I feel like, even though it’s been a hard year or so, I’m clearly stepping into an organization and hiring and growing. I think that most design leaders still tend to do this. So, then it’s getting those kinds of systems down. How are we going to go about recruiting? How are we going to go about onboarding? How are we going to make that work really efficiently so that we get other people in that help fuel us, in that they’re able to hit the ground running too, you know.

And then more things around development, leadership, and coaching styles of the team looking around those areas Trying to make sure that everyone sort of has that right culture fit and is doing the right thing to keep fostering all that stuff that you’ve put in place. And then probably things like communications comes into play a lot, I would say, yeah, like making sure that I’m having the right amount of communications and transparency, setting context, helping the team really understand what’s going on, how to do their work, how to put it in context, how to keep moving forward and understanding the larger business context.

Yeah. And then, you know, whatever we can do to continue to develop that culture of rituals and, make sure it’s happy and thriving.

Jesse: I love it. What an optimistic vision.

Christina, thank you so much for being with us. This has been great. If people want to find you on the internet, where can they do that?

Christina: Yes. So I am definitely on LinkedIn, though right now my inbox is a little full since I put out that I was hiring.

Jesse: That’ll happen.

Christina: So that might not be the most effective means of finding me. So, but yeah, under Christina Goldschmidt, you can try. I’ll try to get back to you. But also I’m on Instagram christinaonUX. Is a fun way to see all the other crafting things that I’m up to outside of the office. That’s always fun.

Peter: Thank you so much for joining us.

Christina: Yes, thanks for having me!

Jesse: For more Finding Our Way visit FindingOurWay.design for past episodes and transcripts. For more about your hosts, visit our websites, PeterMerholz.com and JesseJamesGarrett.com If you like what we do here, give us a shout out on social media, like and subscribe on your favorite podcast services, or drop us a comment at FindingOurWay.design Thanks for everything you do for others. And thanks so much for listening.