Navigating Design Career Transitions

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: Welcome to the Next Phase. Joining us to talk about what’s next for digital product design is Leslie Witt, chief product and design officer for mental health care platform Headspace. Along the way, she’ll share with us her journey from designer to design leader to P&L business leader, she’ll also talk about building the credibility for a broader mandate for design as well as for yourself as a leader, and what to do when your intellectual tendencies get the better of you.

Peter: Hi, Leslie. Thank you so much for joining us.

Leslie: Thank you so much for inviting me.

Peter: So we always start these conversations in pretty much the same way, which is who are you, what do you do?

Leslie: I mean, that’s like an existential question, yes? Maybe I’ll start with the concrete answer. My name is Leslie Witt. I am the chief product and design officer at Headspace, which is the world’s largest, most accessible, and, I would say, increasingly most comprehensive mental health care platform out there.

And I also am a mom to twin 13-year-olds.

Peter: Excellent. Jesse and I are on a exploration. There’s been a lot of conversation in the community around some of the challenges of design leadership.

We’ve engaged this topic on the podcast a few episodes ago, on this thing we call the phase shift, and what we’re interested in is trying to figure out, or maybe do some sense-making around what’s next, right? Where are things headed?

And so we noticed that your job had changed from a VP of design to a VP of design and product, and we thought, oh, well maybe that’s, at least, a way forward. So, love to hear that story of what that shift has been like, from a design leader to a design and product leader.

“Utopian Pragmatist”

Leslie: Look, titles matter–and they don’t. And so I say that just… I’m going to, I’m going to go a little side path first, and then I promise to get back to your core question.

I started my life with a very clear title and role. I trained as an architect. I got three degrees in it. My entire self identity was as an architect, and I discovered 10 years in that I really disliked being an architect. Oh.

And I decided to take a plunge into the world of what I would say, the unnamed. Now, many would call what I plunged into… I became a designer. I joined the company IDEO and one of the things that I most loved in that and kind of connecting to your, you know, I am now a this, was that we got to pick our own titles.

And, you know, in their ecosystem, I was at the time an environments designer, that was the non-formal way of saying architect. But I didn’t put environments designer on my business card. Instead, I picked a title that I would say through all my career permutations is probably what I most see myself as.

And I picked “utopian pragmsatist.” And I think many designers are utopian pragmatists, which is that we’re in this game because we believe we can change the world for the better, and that the better is possible, and that we’re then ruthlessly pragmatic about navigating the vicissitudes of now, the technical capabilities and possibilities, the compliance constraints, the commercial constraints to actually make something come to life.

And that’s the kind of designer I’ve always been. That kind of designer has woven into many categories and incarnations and titles.

And as I transitioned out of a consulting world that is very flexible about what you call yourself and how you show up and who you are and what you can be and in many ways has a model that benefits from that flexibility, into a corporate world that really likes to see people aligned against a skills matrix, loves to see things kind of crossed off and ticked off and told who, you know, owns decision making criteria, what I found was that my style of design was sometimes in direct conflict with the way in which the organization operated.

And so I spent six, seven years as VP of design at Intuit. Thankfully at a company who saw design as a strategic function on par with product on par with engineering. It wasn’t a subdiscipline. And one where design was chartered with core service innovation, something that many other companies is kind of the provenance of product.

What I came to feel was that I had a designer’s approach to problem solving, but in a world that largely ascribed that level of authority and decision making and kind of rights to drive change to a title called product.

And so, as I shifted over into another discipline, another organization, a different sector and industry I kind of, you know, had a brief, like, mourning and grief moment of kind of stopping my fight against the fact that these were the rites and rituals and promises of the design discipline, but instead to take a designer’s hat and approach and ethics into the world defined as product.

So, well, a little bit of a long narrative, but I would say, like, for me, this was coming to grips with the fact that the way I approach design, is largely mapped to the role of product in many tech organizations.

Peter: Follow on that, when we had our podcast that we called The Phase Shift, we actually talked about ego death. That designers need to be willing to let go of that identity as a designer and possibly embrace, and be willing to embrace new identities where they can still be whoever they are, but they might be known in a different way. And it sounds like that’s what what what has happened for you.

I’m wondering though…

Leslie: Can, can I, can I like slight, slight parsing on language? ‘Cause I actually think, like, the identity of the designer is important. I, I definitely feel like it’s, it’s my, it’s my soul and it’s a huge part of my arsenal and worldview, but the title doesn’t necessarily map.

And I think that there’s a difference between say an ethos and an approach, and a titled role. And that the designerly approach, you know, the power of divergent thinking, the ability to take behavioral insight and transform it into new propositions to actually have an aesthetic value that takes things beyond the utilitarian, like, a lot of these kinds of core ethos are things that don’t always map to the title designer.

You can still hold those to be true as you navigate a range of different disciplines.

Product + Design vs just Design

Peter: Totally. I’m just wondering if, if what you are doing is any different with the title product and design than it was with the title design, or are you kind of showing up the same way and it’s just a different label?

Leslie: I, I would say a bit of both, to be fair. I think that as wearing the design hat and title, you are commissioned to be agent provocateur, right? And I would say, especially for me, like, coming from an innovation background, like you are expected to present with some level of future visioning, novelty, operating outside of constraints.

Yes, understanding commercial value, but not necessarily being foundationally constrained by it. You add a lot of value in that frame by kind of helping the group expand what could be very kind of here-and-now analytical thinking into a divergent possibilities-oriented space.

Now, I have to navigate more schizophrenia that impulse to do so, but with the power to actually be the person making the decisions on what we do or don’t prioritize, and it’s hard to do both well, and to own when you’re kind of stepping in which role, and that’s something that I’ve had to get much better at is when I’m not the person that’s commissioned to act in a particular way.

And so instead say, I’m going to have my head of design actually lead a visioning exercise, and then I’m going to be the person helping to deconstruct that and look at capability buildings, and data that we want to collect in order to prove out path X, Y, or Z. That the power position, you know, if I’m if I’m being honest of the product leader, it wields more authority, but then with that comes a level of constraint that doesn’t naturally sit with the role of design.

Jesse: I think that for a lot of design leaders, it’s just very difficult for them to square the role that they see over on the product side with their identity as designers. Now this seems like it’s been an easier bridge for you to cross in part because of what your design practice has always been. But I find myself wondering what you did have to reconcile yourself to as you were making this transition.

What was maybe hard to accept having to leave behind as you are squaring your identity as a designer with this new role, and what was maybe hard to accept that you had to take on.

Leslie: Yeah, no, that’s a, that’s a great push. A few things, you know, I would say like, I would have been out there in the early 1900s as like a suffragette. Like, I, I am the person that wears the banner that is the champion. And I’ve always been, and I do continue to be, a champion for design. And I mean, design here with like a capital D.

Like the art of, the practice of, the craft, and I would say what I’ve had to reconcile, even in a company that has a high premium on quality, is that there are dimensions and places where it matters a lot less. And so where do I fight that campaign and where do I say, actually, this is a workaday problem. This is something that is motivated by a very different set of need states, both organizationally and even from a member. And it’s not where there’s outsized value from levying design craft towards a challenge.

So I would say like that, that stepping aside and viewing things more clinically has been a change that I’ve had to make versus being the person who’s chartered to act as the champion.

And another that I would say has been a dimension to reconcile, is the level to which I have to lead with analytical thinking. I’ve always been, you know, I was a mathlete. I love numbers. I love data. But I historically was able to use it to reinforce a point, versus to kind of operate within a data landscape, first and foremost. And to use that to construct possibility versus to kind of throw out ideas that are either subjective or qualitative and to use experimentation only as a means to kind of prove or disprove.

And so a very different relationship to data, metrics, and numbers, and then a deeper level of responsibility. I mean, one thing I didn’t mention, I also am the head of our consumer channel. And so that level of responsibility for delivering the business and needing to make those decisions on prioritization with you know, an accountability to deliver a number as top of mind.

Peter: Does that mean you’re a operating as a general manager? Like you have P&L?

Leslie: Essentially. Yeah. I own the P&L for our consumer business.

Jesse: Accountability is an interesting thing when we think about the evolution of design. Because I think that on the one hand, design leaders would love to have more accountability. They just want to have accountability for things that actually matter. And there’s a lot of a sense that the business doesn’t know how to create accountability for design because the business doesn’t know how to evaluate design’s contribution to the business.

And I wonder from your perspective, kind of, both wearing your general manager hat and your designer hat and your product hat. That’s a lot of hats, but like…

Leslie: …it’s a lot of hats.

Jesse: …yeah, what, what can you see from all those different perspectives?

Leslie: Yeah. I mean, I think that when I only wore the designer hat or mainly wore the designer hat, as a designer, largely, the qualities that you are caring most about aren’t necessarily always the ones that you are most accountable to deliver. And they’re not far apart, but would say most designers I know, and I put myself in this category, care first and foremost about member value or customer value.

Is this thing that I have brought to life actually doing something meaningful and important? Did it fulfill its mission? And the range of proxy metrics that we sometimes use for those things, say, like, adoption or engagement, don’t necessarily prove out that you’ve actually added value.

There are also things that most people realize can be gamed to deliver a result that looks good on a dashboard, but isn’t necessarily getting to the core point. So like, I’ll give an example from the world that I live within, which is our core member value is that we help you feel better, that you’re less stressed, that you’re less anxious, that you have lower symptoms of depression, that you sleep better, right?

Those are actually like the values that we deliver. Now, I will always say, like, engagement is like the a priori to be able to deliver value. So I am pro-engagement, but it’s not the goal. And simply by delivering engagement, I don’t prove out that I actually delivered on value. By delivering on value, I don’t necessarily deliver value to the business.

And so what I have focused on, and where I see these worlds coming together and how designers can kind of bridge the synapse is one, to understand how the business makes money, to understand what value an end user derives from a service and to try their damnedest to bridge between those worlds and realities.

And sometimes that means actually getting into business model design. So, in a world where you want heavily for the reward to the organization to be that you built something of value, how do you actually think about the ways in which that either saves money or earns money, or, you know, kind of does, does something that actually sustainably means the organization is incented to actually align to that.

And I think that those dimensions… proving out that you understand the mechanics, that you are focused on durable value and that you can connect the bridge between those things, I think that’s where designers both gain a lot of credibility, and maybe that credibility supplants what often I think accountability translates to, which is I got autonomous decision-making authority.

I think very often that’s what, what folks would like accountability to mean. I think it’s that I am going to be someone who shows up and says, I’m going to move this number. I’m going to do this thing and no matter what, that’s the end outcome. And I’m going to move mountains in order to do so.

Jesse: It’s interesting because it also suggests sort of taking accountability for outcomes more than activities.

Leslie: I believe so. And now I’m talking at different levels of the food chain, right?

Jesse: How’s it different?

Leslie: I think that if you’re someone who’s on a working team that’s assigned a set of tasks, and asks if you’re, you know, a junior I C, independent of function, like, that set of arguments and kind of conceptual resolution has to have happened above your pay grade largely so that you are actually empowered to do that thing.

But that thing, doing that action and doing it well, and understanding how it ties up is something that you can be accountable for no matter what level of hierarchy you are at.

Peter: In conversations that I have with clients and just people out in the industry, and I’m wondering your take on, is as design attempts to identify how it can be held accountable, how it can be seen as valuable, those measures are, at least in anything that is used by people, the same as a product managers’ metrics, right? Design and product end up driving towards the same thing, which maybe speaks to why you’re in the role you’re in, but then, how have you, have you had to, how do you encourage others to navigate this tension where, at least in some organizations, functions need to prove themselves in order to like, you know, get headcount or whatever.

But if design doesn’t have a value distinct from product, how have you navigated that? Or how do you counsel others to navigate that?

Leslie: Yeah look, I think right now it’s shifting. So I could tell you how I navigated it in the past and we still, by and large, have, you know, a triad or a quad model where we’re looking at having, you know, a product leader who is, you know, establishing the product requirements and really kind of prioritizing attributes of the of the process in tandem with an engineering leader, who’s, you know, building out the kind of capabilities and scoping, and a designer who is, you know, anchoring exactly how that comes to life concretely within the user experience. Like we largely fall along a kind of traditional triad model.

But I’d say that, you know, with the rise of AI, right, and the reason I bring that up is that some of the technical dimensions of what have held those two disciplines apart are falling away as barriers. You know, I have a very, like, experimentation and data oriented designer on one of our membership teams who loves to build dashboards and technical experiments. Well, that’s something that used to be the kind of technical skill set of the product manager. I’ve got a pretty young and very ambitious product manager who has learned a lot about how to set things up in Figma, and is able to kind of take modern tools and, increasingly, content generation and like put together some pretty compelling flows and prototypes.

And so the blur that used to kind of exist between craft skill sets and things that I’d say had like a technical barrier to entry–and this is very much true for engineering as well, right? You know, it was like code, code was like the Holy Grail that no one could cross. And, and, you know, like that, that key to the castle that was locked up by computer science capabilities is, is it’s getting unlocked at least partially.

And so, what do you do with folks who, yes, have different potential biases, but come in with a lot of shared skill sets or lower barriers to entry on those skill sets? And I’d say we’re still very much navigating that reality. More apparent in certain sectors than other.

Peter: What do you mean by certain sectors?

Leslie: I mean, like depending on the problem that a team is chasing, there are ways in which the unique skillset of a craft based designer, it’s like we just defined and designed a new AI bot, but we’re joining the crew. The skillsets of conversation design, and even like brand design, we created a character.

It has a complete tonality and a name. Like, that’s a more craft-oriented challenge and one that it’s incredibly important to have someone with expertise nail, then say an adaptation of a set of flows and a simplification of clinical intake. It has a form. It has examples out in the world. I don’t necessarily need someone with deep finesse and deep craft expertise to tackle that. I need someone who knows how to build and test and use tools.

The Distinct Role of Design

Jesse: As I imagine this playing out, into the future, it seems to me that if you’ve got, like, craft level design work that’s now happening in lots of different parts of the organization across a range of roles, some of which are not design roles and not participating in design processes per se, then it seems to me that the role of design leader, someone who’s going to be that champion for design as a practice, design as, as a value driver in the organization, it almost becomes more like governance.

Leslie: Maybe it’s governance and inspiration. I mean, I think like anyone, who’s played in the space of more traditional, like, graphic design. Often this still is the reality of say, like brand creative. That world has existed for a long while in defining guidelines. And then acting as enforcer, you know, brand police, they’re here like, you did it wrong. And, you know, while the team is deputized to do X, Y, and Z, if they have the skills, like the rest of everybody needs to align to a particular zone. And not to say that that doesn’t have some real value.

But I think it’s, I think that’s a depressing role. If what you’re out doing is kind of guard… it’s a retrograde role, right? Like, you’re almost by default, then, protecting the status quo versus pushing and defining the future.

And so I would argue that you might have less dominion, right? Like, there may not be 300 designers on your team who are involved part and parcel in everyone’s work streams or in a subset of work streams, but in some ways you have potentially more influence. And so, how are you out there now that everybody is cracking open ChatGPT to apply their hand at conversational design now that everyone is playing around with a variety of different tools and seeing what they can bring to life.

How are you, one, inspiring them with what quality looks and feels like, and how you think about a design process? How are you out there showcasing what good looks like? And then I’d say where I’m more interested in design-led governance is on questions of ethics, and, what is that insight into human behavior? What is that foresight, into the way that technology can evolve possibility, doing in terms of driving us to a better future? I think design kind of owes itself the responsibility of having an ethical viewpoint on it and helping an organization think in that capacity.

Peter: Why does it feel like design is often the one that raises its hand to care about ethics and the rest of the organization let’s it slide? Like this comes up a lot that that designers feel like they’re the ones who…

Jesse: why do we have to be the ones all the…

Peter: …yeah, who like, how is not everyone concerned with the ethical implications of what we’re doing, but designers, at least in my experience, are the loudest in the room, reminding people… deceptive patterns, right, was, was a concept that emerged from the design community, right?

It didn’t come from somewhere else. So yeah…

Leslie: To be fair, I don’t think designers are the only ones who care, but on the flip side of what we were talking about earlier, which is that designers are often not held accountable to a metric, I think there’s amazing freedom that comes with that too, because it’s freedom to operate outside of behaviors that are dictated by achieving a number.

Like, let’s say I’m a marketer who is going to be gold and bonused on whether or not I was actually able to increase sign up by 5%. I’m going to do my damndest to increase sign up by 5%. I’m going to do my damndest to increase sign up by 5%, right? And out of probably very seldom actually bad intention, I’m going to chase doing that in such a way that might have a lot of unintended consequences.

And designers have the right and the responsibility to point out what are the things that we’re systemically avoiding or how are we taking negative advantage of human behavior and motivation and, in a way, because designers also know those tactics, they are the ones most able to come back and say, hey, we’re actually like weaponizing,right, human psychology, we are doing something that sits opposed to our values basis. Now that’s like one thing to do when what you’re talking about is you know, a tactical marketing campaign.

It’s quite another, and I think it takes a level of intention and it absolutely takes buy in by other disciplines, and it takes both good intentions as well as mechanics to audit what actually happened when you’re talking about applications of LLMs, when you’re talking about what data privacy rights and consent are we putting in place of our members? Are we as explicit about both the intended use and the actual use of this as we need to be?

And, like, kind of holding up that lens of inspection for the organization. I think design often is one of the few disciplines that has both the skill sets to do so, and in many ways operates enough adjacent to the litany of metrics to be able to have the oxygen to do so.

Jesse: It seems to me the gap, then, here is really one of credibility, that the designers have the capability, they have the mindset and the appropriate, you know, resources to take on these challenges but they’re not being asked to, and when they do bring these things up they’re kind of like shunted aside.

Like, don’t bother me, kid, I’ve got a business to run here. And so a lot of these Design leaders feel like, if I talk about anything other than corner radii and button placement people think I’m talking out of turn. And so I wonder about, how to make the case that design has something to contribute here, even in cases where that alignment is possible, you know?

Connecting Design to the work of the Business

Leslie: Yeah, I mean, I’ll be honest. I have not personally had that experience. So well, I respect that many have. I do think there’s a dimension of, what are the values of the place that you work and, that no one’s perfect, right? Like, but are you working in a place that has some level of precondition to care, right?

I mean, because there are places that surely don’t, and then I think you’re trying to run something up the flagpole that never going to stick. But I think most places, like, there’s an intention. There’s a set of positive intentions, at least at a like mission declaration level, but then bridging the gap between the operational metrics of how that business runs, and it’s ambitions, there’s a wide vacuum of definition between what those things are.

And you know, I think it’s incumbent, especially on a design leader to foundationally understand the commercial mechanics of the business that they work within, so that they can bridge that gap.

I mean, the same thing is true here. Why should the business care? To be able to speak in the language, not just of like, Hey, all we should care and we should do the right thing. Why? Like, what happens if we don’t?

Because what is often being seen if we don’t is, I either just cut costs, well, that sounds great, or I just put a little bit more money in the coffer. Well, that sounds great.

So you’re going to tell me a different narrative about why I shouldn’t. I think you need to do two things in tandem, like paint a concrete picture of the risk, okay, of continuing, and then create a concrete pathway of what else, like, if I don’t do this, what should I do? And so I think you can get into a position where you’re the person that’s flagging, why not, but you’re also not painting the path of possibility.

Peter: From what I can tell you have worked in pretty high design maturity environments, right? IDEO, Intuit. Now Headspace. And I think some of the challenges that we’re seeing are with design leaders who are operating in lower design maturity environments, where they have designers, but they, kind of, don’t know why. They just got them because that’s what you were supposed to do.

I’m wondering though, What can help people in these lower maturity environments, get some purchase, get some traction?

Leslie: A lot of the companies who hired IDEO back in the day, and I was there 2005 to almost 2014, were coming because they were not high design maturity environments. They were organizations that lacked these infrastructures and capabilities, and they often did have design organizations within them, but they were extremely tactical design.

You know, it was maybe one step different, one step more technical than a brand creative team. And that’s not to slam any of those things, but like, it was not design as a strategic function. Design didn’t own research. Design was very much, you know, there to execute.

Setting Design up to succeed

Leslie: And what I would say essential to do, is to understand who cares about the idea of design, slash the things that you can do through design, having more power, actually having purchase and finding that champion as high up in the organization as possible is essential. And so, you know, one of the things I learned from that time period in life was we needed two things in order to be successful as consultants within those environments.

We needed like C-suite level championing, and we needed operational level advocacy buy-in and collaboration to what we were doing. Because if we had one without the other, the ideas were dead on arrival, right? Like, great, the CEO loved what we came up with, but this business leader has zero interest in executing on it. It wasn’t their idea. Thanks for the gift, but no, thanks, right.

And then the opposite side, if it was just like a passionate business leader who, you know, had zeal in the organization, it tended to have no staying power. And so there’s still real value because I would say, like, well, you’d get like a demonstrable point on the board. You’d have somebody who is committed to seeing something through from like, Idea to execution, but it was very hard to then kind of harness that as a repeatable event.

But, but if you can get that orchestration of a triangle, and maybe you’re doing it by proxy, you’re showing how this has worked effectively to build a business and other organizations, and as an individual, as a design leader, you’re making those relationships happen. You’re finding a high level advocate. You’re finding someone with whom you’re partnered who might have more decision making authority than you and you’re demonstrating in a tactical, tangible way that working in this capacity, where design has more influence or has more of a strategic charter, actually helped to do something meaningful, then you can start to grow that into a broader way of working.

I will say for the very same reason, as I stepped from consulting into corporations, I knew and I’ve stayed very strong on this. I would never take a head of innovation role or say, like a chief design officer role at a company that did not have any type of organizational maturity around design. And for me, that was because I had seen too often the way in which, like, that was, it was novelty. It was somebody to be brought out to an investor relations group to parrot, like, really cool vision work that really had very little consequence on the way in which the organization operated. And I don’t think a singular hero can affect organizational change.

Peter: A question that I’m often asked is, how do you know that the companies you’re talking to are mature? Like, what are the indicators that they’re the kind of place where design could thrive? I’m wondering, as you shifted from Intuit to Headspace, what were those indicators that you saw at Headspace that allowed you to feel like, okay, this is a place where I can actualize myself in some way.

Leslie: Yeah, I mean, in that case, for pure honesty, I was recruited by someone I had worked with before, who I’d worked with at both IDEO and Intuit, at least adjacently. And so I had a trust in who would be my boss, the CEO, and that was huge because I knew that person had a visceral understanding of both me and the role that I saw design playing in the expanded field.

I would say that the other indicators, you know, I could look at the product and tell that there was a care for craft. There was a demonstrated history. And then probably the kicker for me was that the conversations I had multiple times across, even like the CFO, referenced the research that design had led to understand the core landscape opportunities.

And, that proof point of hearing someone else unbidden reference qualitative design research that was like, okay, this is real. And this is a place where that input is taken seriously as part of driving a business strategy forward.

Jesse: Yeah…

Leslie: And look, I don’t, I don’t pretend that everybody gets to cherry pick. Like, well, no, I’m not going to join that organization. And no organization is perfect. Far from it. For any role. And I would say, like, part of now wearing more and more hats, like the, person in charge of that P&L and the person in charge of our product prioritization, I see that there are frustrations and downsides and maturity issues across the continuum in a way that I probably didn’t respect as a designer who felt like I was lone man on an island and a place where everyone else had well-defined, well defined, well respected roles. this frustration I think is actually something that can be leveraged positively as a universal driver to enlist collaborators in your cause, because you can actually help them buoy their cause.

Relationship with the C-Suite

Peter: If my quick Googling is bearing out, you’ve had two new CEOs since you joined. So you’re on…

Leslie: …that’s correct. I’m on my third.

Peter: So given that you were brought in by one CEO and that relationship was so important, what has changed for you? This is something I noticed myself as a design leader, even if I wasn’t reporting to a CEO, even if the CEO barely knew who I was, who the CEO was had a very direct bearing on my ability to succeed as a design leader. And I’m wondering, kind of, how that has shifted and evolved as you’ve had new leadership come in, and how you’ve had to kind of show up, either the same or differently, given the nature of what was happening in the C-suite.

Leslie: Yeah, it’s a great question. And, you know, I will say that it’s hard to navigate a managerial change. And I think about that all the time you know, I think there’s not a designer out there, there’s not anyone who’s worked in a corporation who hasn’t gone through a reorg. And then, you know, if you’re, newly mapped to a new manager, even if that person existed in the organization before, they’re new to you and establishing that level of trust and belief and knownness and shared philosophy and prioritization is hard, right? Even if at the end of the day, you have mutual respect across the continuum.

And so, yeah, it’s been an interesting journey. You know, I mentioned I was recruited by someone who knew me and actually had known me at least in these kind of like off and on ways for over a decade. And so I was able to hit the ground running and I had really been hired, although my title didn’t say product, I was hired to drive our explorations around stepping into the mental health care space for us, like, running a therapeutic pilot that then led to a set of M and A evaluations and that’s actually something that I discovered when I was into it because I was leading a lot of the innovation product space. I really love actually thinking about not just organic growth, but inorganic growth and helping to drive that evaluative process. It’s itself a very, like, creative act.

And that path led us to acquisition of a company Ginger. Which is how I got my 2nd boss, because as we made that decision to merge, the decision was made that that company’s CEO would become the boss. And deep respect for that individual who was with us for the last 3 years and just recently left the company, which will be the kind of 3rd chapter.

But what was different foundationally was that I would say we went from an organization whose business model meant that design as an act and product as a medium were the primaries to an organization that built an enterprise benefits platform where sales was the primary, and so a very channel centric view of the world versus necessarily service centric world and a really different means by which you make money.

You have to get a singular buyer to see enough value to sign up for a massive, sometimes multimillion dollar contract. And so they’re looking at like, how many boxes do you check? How confident are they that this thing is going to stand the test of time? And it deprioritizes some of the dimensions of what I had most cared about in the advocacy that was very directly mapped to our ecosystem.

And so in that world. You know, as I saw how I could both shape our commercial model as well as shape what I wanted to have happen, that’s how I became the head of our consumer business. Was like looking at where does the influence that I want to have actually sit within this ecosystem and, you know, to be quite honest, I would say with our, third leader who’s come in really to help us take the world that we’ve now fully integrated, and, you know, we kind of like we have gotten through that incredible platform transformation that if any of you have ever gone through, it’s not necessarily a fun one, but it like gets you to a place where it just has different potential energy forward.

Like he’s now here to act as like a maximizer. How do we take that and really take all the latent potential and maximize that energy. And I imagine that we’ll need to permute again, right? Like what are the things that the organization now cares about? How do we meaningfully shape them? And, in a world that now has a whole set of new technologies, in this world, what are the things that will matter most to an organization, both from an innovation and an incrementality standpoint?

Planning for Innovation

Jesse: I’m curious about where things are going, as we’ve seen innovation, as a standalone function, kind of fall by the wayside, innovation consultancies are having a hard time selling those services these days. And yet you did identify it earlier in this conversation as being something that design really has an opportunity to contribute toward, with design’s own toolkit and mindset and skill set. But then I wonder about what you said about having to embrace the spreadsheets and step into the world of the analytical in order to actually take on that role. And I’m wondering, where would you see an ideal place for some more of that old innovation magic in here?

Leslie: Well, believe it or not, I actually think I’ve come to love the world of prioritization, and that where I see it able to really create space for the new, both the minor new and the mega new. You know, there’s a variety of different frameworks you can use, but the one I’ve loved for years is a horizon innovation framework, and it looks at the portfolio of SKUs and channels and kind of activities of an organization and ranks them on their maturity, and then assigns resources really based on that maturity.

And what you want to have is a lot of things that are in the horizon one category, which means they’re fully mature. Like that doesn’t mean they no longer get investment. It actually means they get your most investment because you, you know, far more as you get further down the pike, the value of level of effort equals level of result.

And so they’re highly predictable. You know, it’s where almost all of your go-to-market dollars should be spent, and it’s the cash engine that runs the company so that you can invest in a few things that are in horizon two and maybe one or two things that are in the horizon three hopper.

And, you know, if you go to horizon three, that’s where I’d say, like, that’s where innovation sits. And as a company, you want to be placing as small, but as a complete, of a bet around a set of things that you think could be your future and giving them enough oxygen that they can deliver meaningful results that will actually be indicative so that you can decide whether or not you should fuel them or kill them, right.

You know, it’s more of a. intrapreneurship type of experience and one that I’ve found a lot of pleasure in doing within the idiom of, if successful, it’s transformative, either to the way that we do business or to the way that we drive commercial value and to know that you may not necessarily, even if it’s greenlit, get permission to then build it internally.

That’s a great hopper horizon three, for M&A, right? Like, okay, great. We proved this out. This actually is something that there are more mature businesses out in the ecosystem that we might decide to bring in, or this is actually something that we want to grow and scale internally.

And that’s really what that middle hopper is about. So I would say, like, the space I found for innovation is to develop a kind of discipline and rigor about it that lets you allocate resources, as unsexy as that sounds, but to quarantine those resources so that they’re protected and can actually do their job.

Jesse: Right. So this suggests then that if design really wants to actively participate in these processes, it means sharpening your ability to do some strategic long term forecasting from a design stance, a user value stance.

Leslie: Yeah. I mean, yeah. One of the things I learned at IDEO, I mean, not like in a formal way, but by, like, peering over the shoulder of the few, we called them business designers, but basically the 10 human beings in the organization who had MBAs, was, they would do a lot of discovery driven planning, which is a fancy word for basically saying like, I don’t know what this is going to do, but I can set up a set of variables, like, and some of those are known: H ow big is this addressable market? What might we price this at? What would be a believable, you know, X, Y, and Z in terms of adoption. And I can make this machine that lets me explore possibility and see like, from an incrementality standpoint, does this matter if I get 10x more people to sign up?

That passion for, I can make this so much better, has to be linked to, and if I do, does it matter? And making a model to kind of prove out to myself, okay, yeah, yeah, this is something I should continue to think is a big deal. Or, ooh, okay, even if I 5x this, at the end of the day, we’re talking about a business that’s in the single digit millions. Well, that’s probably not worth the time and effort versus something that has just a much bigger, you know, delta.

Peter: As you were reflecting on some of your experience at IDEO, I found myself thinking or wondering about career development, right? You had an opportunity for career development. You were able to pivot from architect, into environments designer, into some type of general strategic business savvy design lead, who then was able to then kind of take that and go quote, unquote in house and, thrive at places like Intuit and, Headspace. And it’s not a secret that design agencies and consultancies have, whether or not they’re on the wane, the percentage of design practice happening in those environments versus in-house is way skewed.

And I’m curious your thoughts on what we as a community, as an industry, as a practice are missing by not having those types of environments that tended to create a space for a certain kind of practice that you don’t get typically inside of enterprises, inside of corporations. And then, not only what are we missing, what, if anything, have you tried to institute as a design and product leader now with authority, with people listening to you, you have power. What have you tried to do organizationally within the spaces that you oversee to encourage that kind of professional development?

Personal professional development

Leslie: Yeah, I mean, first of all, I just want to acknowledge, I think that, you know, through no dimension of will, but through total serendipity, it was an incredible time to get to have that moment where design was a darling at the ball, where IDEO had that type of like broad stroke permission to come into spaces and to be consulting fortune 100 company CEOs about perspectives on their companies with total hubris.

And like I look back on that as something that gave me probably undo confidence, but a level of confidence that certainly is valuable as we carry forward. So I want to acknowledge that as a starting point. So that’s not necessarily the reality of right now.

I think, like, in exchange there has been, you know, at least up till very recently, and I believe it’s not going to like change and pivot on a dime, many more roles for folks with design backgrounds of a variety of ilks to step into high paying corporate roles. That wasn’t really the world that existed back then.

And I think in exchange, however, it becomes very easy to become, you know, in the kind of ideal parlance of the T-shaped individual, where the long arm of the T is your depth and the horizontal arms, IDEO worked really hard on building those horizontal arms. And that makes it really easy to grab somebody else’s hand and skip on over and, you know, pretend for a while that you have another depth and then actually develop it.

And I would say that those arms have to be very intentionally exercised in a corporate environment. You can get pigeonholed, especially in a large corporate environment, into extremely kind of technical sub-dimensions of a skill. And that might be how you get hired, right? Like, I actually got hired to IDEO because I was a good 3D modeler, and they needed somebody who could 3D model. Now, I did two projects where I 3D modeled, and then I tried my damnedest to never do it again.

But I do think a lot of times why you are hired isn’t necessarily why you stay, and it’s definitely not necessarily why you move up in the world. And so, you are the one who knows both, like, who you are as a myriad individual the best, the organization doesn’t know. It doesn’t fit neatly into a matrix. Grab the thing that you’re both most passionate to learn and that you actually think you have a chance of being successful at, and raise your hand, use it as a ladder to advocate for what you think you can do, what you want. And then try your damnedest to do it well, and that’ll create opportunity.

It’ll also help you understand, like, do I actually enjoy doing this? And so I think that that dimension, and that does assume that probably is some privilege wrapped around that, but like that dimension of intentional self advocacy, and not necessarily foresight on what’s going to be important, but insight to yourself is key. And being okay with the fact that I think like another design nature is like, you get bored. Seize that boredom as like the biggest thing that jets you forward. Don’t just like keep rinse repeating.

Like you’ve mastered that skill, you’ve achieved mastery, move on. Keep it as part of your like, it’s part of your toolkit. What else do you want to know? What else do you want to explore? What else do you want to learn? I would say in our organization, we probably aren’t as institutional about it as we could be and should be. But we have a fair number of forums that are very democratic in the way that they work. And everything from, you know, your kind of traditional hackathon, those can be formed with teams from kind of anyone’s input, anyone can kind of propose sets of ideas forward.

I make myself available weekly with an open office hours, and I would say what I see is across functions and across levels, the folks that most want to come and kind of pitch themselves in an idea, show up, they show up and they, they put themselves out there. And I do think you have to take some of those risks in order to yield the opportunities that you desire.

Peter: I realized I don’t know what all you oversee. I imagine design and designers, maybe researchers, but is there like data or other product functions that are in your world as well?

Leslie: Not necessarily producty functions. I also have our whole content organization. So, you know, Headspace makes, a wide variety of multimedia content. And so that organization lives within my purview in reporting structure, the brand creative team lives within my structure as does our science team.

And so that is group of folks who have mostly clinical backgrounds, as well as actuarial backgrounds, who are responsible for evaluating whether we are efficacious, right? Like, do our services work? They run RCTs, they collect real world evidence, they run longitudinal studies to understand health outcome savings. And we do have a few clinical psychologists who are product managers as well, because we are making, you know, healthcare a consequential product.

Peter: How did you make it clear to the C-suite that you were credible in leading clinical psychologists, right? You don’t have a background in that. You don’t have a degree in that you’re like, or…

Leslie: I don’t,

I don’t have a background in that.

Peter: But I get the sense you must have demonstrated some ability or capability that allowed others to go, Oh, okay. She can stretch beyond the boundaries that, that she’s currently in.

So let’s, give Leslie more responsibility. What do you ascribe that to?

Leslie: I tend to wear a pretty strong veneer of credibility period, like, to own that. Like, I am versant, I am fairly intellectual, I’m pretty rigorous and I used to be an academic, and while I wasn’t an academic in areas like clinical psychology, you know, like with ability to speak post-structuralism and kind of go heady, you can, you know, help yourself like be nimble and appeal to the folks who have PhDs.

And so that’s how I ended up inheriting the science function, was when our head of clinical at the time left the company. That team asked to report to my organization. And I think that’s because they had experienced directly that I cared about what they were doing. I valued it and I could get smart enough quick enough that I knew how to empower them.

And I do think that a large part of that, you know, organizational choices tend to not just be tops down. But they’re bottoms up and which functions decide they can thrive under your leadership is a major factor in terms of where things end up sitting.

Peter: I’m glad you used the word intellectual. Because it’s been evident, frankly, in our conversation that you are well read, extremely articulate, broad vocabulary. And if I am immodest, I like to think similar things about myself and that has gotten me in trouble in a lot of contexts,

Leslie: Me too. Me too.

Peter: I am very comfortable going very abstract, being very heady, being very conceptual, being intellectual. And I think, losing people overcomplicating situations. All of that. And I’m wondering, it sounds like you, you know, you’ve had a little bit of that experience, is this something you’ve had to kind of consciously dial in?

What, what have you done to manage maybe some of these tendencies and inclinations in making sure that you’re coming across as, confident, capable, but not like overwhelming in the way that can sometimes happen to folks who get really spun up about their ideas.

Leslie: Yeah I mean, I think I’m still on that journey. Let’s be completely honest. But I’ve had some great advice along the way. I had my first boss at IDEO was a gentleman named Fred Dust, who also came from an architectural background. And, a delightful human, and he would just call me out and mock me endlessly when I would use way too many multisyllabic terms. And I think one that I remember, I was talking to, like, I think American Eagle Outfitters, it was like a very workaday retailer that we were doing a project for. And I said something about perambulate and he’s like, she means walk. And so he would just, just make fun of me.

And I realized that there had been this normalization, especially in architecture of speaking in a particular way that wasn’t intended to obfuscate, but did. And so I try to like tap that down. I would actually say like in a funny way, the more excited and ad lib I get, the more it comes out because then I’m not like intentionally thinking. And in my natural state, I still retreat there. I do a lot of writing and I tend to write like it’s some long form prose,

Peter: For yourself or for public consumption?

Leslie: Um, for all sorts of reasons. Both, I do both. But I would say, like, first and foremost, I was mentioning it because I tend to write to think. in order to process, like, what really do I think about this and how is that going to manifest in, you know, X, Y, Z sets of decisions, and I need to do the corpus you know, some people are like, I just need the TLDR.

I’m like, well, to get to the TLDR, I have to write the big part first, and then, like, distill and reshape. But yeah, so I’m definitely still on that journey. I can be pithy at times. But, tend to like love a good long form debate.

What’s next

Jesse: Leslie, what are you most curious about as we enter this next phase?

Leslie: I tend to be hopeful. And, I’m going to just kind of focus on, like, what the possibilities of technology bring. I like to imagine a world in which, like, these radically more empathetic means of interacting with technology help us address the loneliness crisis. They help us have people feel more seen and more heard and that doesn’t have them needing to navigate some obscure graphical user interface in order to find what they need, but like, just kind of surfacing the world to them is knowing what they need. And it’s kind of working in this capacity that’s helping fill the blank.

I think that when I think about being an employee, kind of independent of function, that we’re not being made obsolete, but we’re becoming super-powered and that that’s, you know, allowing us to step outside the mundane, do a hell of a lot less of that and reserve time for things that creative human beings can only do, and that we’re going to understand that those dimensions of what I just articulated as kind of best case scenario are highly privileged. I’m less worried about like, do, does so and so’s profession become obsolete, do radiologists get replaced by the machine?

Like, I’m less worried about that because largely all of those people will be fine. I am more worried about you know, an economic reality, a social reality, a political reality that is already harshly schismed and divided. And where both the resilience of folks who are at the bottom of the pyramid, as well as the means to take positive advantage of the evolution of technology is so much lower and how do we, as a society, as, as social engineers, how do we tackle that intentionally, so that we’re not increasing what I would say we are already, already clearly seeing, which is that it foments immense discord, violence in the world.

Jesse: Well, if design leaders and design teams can do something to shift all of that, that’s a vision worth reaching toward.

Peter: Most definitely.

Jesse: Leslie, thank you so much for being with us.

Leslie: Thank you. I really enjoyed the conversation.

Peter: Yes. Thank you.

Jesse: Where can people find you on the internet?

Leslie: Sadly, I would say LinkedIn is the best place to find me

You can find me and connect with me on LinkedIn. I, for whatever reason, just never hopped on the Twitter brigade. And then once it became X, like had no interest. So, you know, hit me up on LinkedIn and look forward to connecting.

Jesse: Thank you again.

Leslie: Thank you.

Jesse: For more Finding Our Way, visit findingourway. design for past episodes and transcripts. You can now follow Finding Our Way on LinkedIn as well. For more about your hosts, visit our websites, petermerholtz. com and jessejamesgarrett. com. Peter recently launched the Merholz Agenda, his semi weekly newsletter.

Find it at buttondown.com slash petermerholz And if you’re curious about working with me as your coach, book your free introductory session at JesseJamesGarrett. com slash free coaching. If you’ve found value in something you’ve heard here today, we hope you’ll pass this episode along to someone Else who can use it. Thanks for everything you do for others, and thanks so much for listening.chrome-extension://knjbgabkeojmfdhindppcmhhfiembkeb/index.html