Video Rewind: Cassie McDaniel: How Medium eliminated its PM function and started moving faster

0:00Aarron:Hi folks, we're taking a holiday break, so we're rewinding to one of our favorite episodes this year with Cassie McDaniel, Medium's Head of Design. We're also including video from the episode, which you can watch on our sub stack or at our YouTube channel over at dbtr.co slash YouTube. Erin and I hope you have a lovely holiday with your family, friends, and loved ones.

0:23Eli:I think it can be frustrating for a team that wants to move fast if the designer is, oh, poor me, I can't believe you said this about my work. My work is perfect. We are iterating so fast that you really kind of have to just take it and run with it and try to remove yourself from this process so that you can focus on making the work better. It is about the work. It really isn't about you.

1:12Aarron:Thank you. moving faster than ever. We chat with Cassie about what led to this decision and why it might not work for all teams, how she thinks about balancing Medium's legacy of thoughtful design while moving the product forward, and how writing can help you advance your design career. This is Design Better, where we explore creativity at the intersection of design and technology. I'm Eli Woolery. And I'm Aaron Walter. If you're hearing this, you're not currently on our premium subscriber feed? Design Better Premium subscribers enjoy weekly episodes. You get four episodes per month rather than just two.

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2:38Aarron:We'll return to the conversation after this quick break.

3:05Cassie McDaniel:Done hoping it looks anything like the picture when you tear open that envelope? It's time for a little in-person spring treat. It's time for a trip to Ross. Work your magic.

3:19And now, back to the show.

3:26Aarron:Cassie McDaniel, it's such a pleasure to have you on Design Better.

3:29Eli:Thanks for having me. I'm really happy to see you again.

3:32Aarron:We were just talking before we hit record that we've crossed paths a lot on the web. I don't remember exactly when we first met, but we met in person in New York at a smashing conference and you had a brand new baby that you brought on stage, which was pretty impressive that you had a brand new baby and you were traveling and kind of diving back into everything.

3:53Eli:You know, there was no other choice at the time. She was a real finicky baby and she would only nurse. So she would not take a bottle. So anywhere I went, she had to come with me. So if I wanted to keep doing stuff like that, here she came. But I do remember bringing her on stage to that conference. I don't know. I don't think I would do that again. But I also feel like I had no other choice. Yeah.

4:14Aarron:So these days you're leading design at Medium where you've got a great team of folks and you've been building that team over there. We want to dive into that. But I think one thing that's really interesting to me is just how diverse your background is in design. You've worked at agencies, you've run your own agency, you freelanced, you worked at Mozilla and various other places. Could you give us a quick tour of your background and maybe tell us a little bit about what those experiences bring to you as a design leader today?

4:48Eli:A tour is the right word because I feel like I have had a lot of different stops. The thing that was always driving that was where is the place that I feel like I most belong and can be the most helpful? always kind of looking for this perfect match between my skills and where I wanted to go and how I wanted to apply them in the world. So it was always about how can I make meaning with my design skills. So I studied graphic design at the University of Florida. I grew up in Florida. I'm back in Florida, but only after living abroad for a decade and a bit, I went to school. I did an exchange program at the University of Leeds right out of college.

5:33Eli:And that's what kind of got me to leave Florida. I lived in England for two and a half years after that. And I was actually trying to find a job under the table. I did not have a work permit. Wouldn't recommend doing that today. But at the time, I was just looking around for a really good internship. And this one place offered me a position that would pay me under the table. So I ended up at this small digital agency in England, which happened to be where I met my husband. And we stayed there for two and a half years and then moved to Canada. And again, I think because we were immigrants, we were just looking for a soft place to land.

6:12Eli:And I ended up in ad agencies again in Toronto, Canada. And I worked at a larger ad agency and I really didn't like that. It was just very cutthroat and not at all the kind of community or family feel that I was used to for my first job. And it's like, I don't want to keep doing what I was doing at the first place, but I want to grow. I want to keep pushing. And so after another small move to a digital agency there, I started freelancing and I was like, I'm just going to illustrate this children's book that my dad wrote. I'm going to finish that project and I'm going to start writing. So I I started writing design articles and publishing those.

6:50Eli:And I actually went to a conference on a press pass. And that's where I saw this panel with a bunch of doctors talking about design and healthcare. And I ended up reaching out to one of them for a quote, and he ended up offering me a job. So I got back into full-time employment through that and worked at this little innovation lab inside a hospital and learned a lot about human factors, testing. That was kind of the advent of the mobile phone. And we were doing a lot of like chronic self-care apps, mobile apps for diabetes and asthma. And I really loved that, but there wasn't a lot of growth opportunity.

7:30Eli:And I was sort of feeling the pull toward leadership and toward management. And that's when I took a risk again and moved over to a different industry. And I found the job at Mozilla. So I was the first UX UI designer at the Mozilla Foundation. and worked with that team there. That's where I became a manager first. Then I became the design director for that team.

7:54Aarron:You said, I felt the pull to leadership and management. What does that mean? And what was that like? What is it you wanted for yourself?

8:03Eli:Design for me, I really appreciate the craft of it. When I was in college, I didn't even know what design was. I had no idea. It was my sister-in-law studied graphic design and said, maybe you should look at that program. And then I knew that that program at UF was one of the more competitive ones to get into. So I was like, I'll do that. Okay. And I got in and I wanted to be a painter though. I wanted to be a painter or a writer. And there was something about the flow state that I really enjoyed. But once I discovered design, I was like, I don't know, this is way better because I can apply this sort of logical, pragmatic part of my brain with the artistic, creative part and make things that really matter for people, that can really be useful.

8:50Eli:I wanted to be useful. I wanted to be helpful in the world. And so design was kind of craft-based, but for me, a lot of it was about making things happen. And the more I worked in teams, the more I could kind of see this big disconnect between people, whether it was designers and developers or between management and executors. And I wanted to help bridge that gap. I wanted to use the way that I thought and the way I could communicate how I thought to help make things happen, however best that was. And I felt like there was always this gap between the creative teams, between actually delivering excellent work.

9:33Eli:And I thought I could fill that gap. I thought I could help. I think that's what it was about for me was positioning myself, not because I wanted more control or because I thought somebody else was doing a bad job. It just felt like a gap that I could help fill. And I think that's still how I think about it today.

9:51Aarron:Yeah. My observation, kind of limited interactions with you, is that you have a perspective. You have a point of view. And you think critically instead of just sort of like taking the problem or the thing that's in front of you. you've got an idea about the right way to approach this. Does that sound right? That resonates.

10:10Eli:Yeah, it's funny that you use the word critical because I think that's actually one that I wrestle with because I think I'm naturally more of an optimistic person, but I do critique over and over and over again. I mean, a lot of us in the creative field do that, right? We can't really be better at what we do if we're not critiquing what we're doing. And we can't help others be better if we're not also critiquing what they're doing. So there is an element of how do you position a critique so that it can be received helpfully? The thinking part of design has always been really appealing to me. Maybe it's more possible today to not think and be a great designer just because the tools are so robust now.

10:51Eli:But when I started, it was all about the thought, you know, and my program at school was way more concept-based. It was not about the tools at all. I think we had a couple of weeks in Flash. We never talked about Illustrator or Photoshop. We never really talked about the tools. That was just something you had to go and play with to learn. The part that was hard was developing the mode of thinking. How does this fit in the world? What are you trying to do here? What are you trying to get people to do? I always believed that design could be really powerful. It was such a powerful mode of operating and thinking in the world.

11:30And with that power, to me, there was always a huge sense of responsibility.

11:35Eli:What are you really going to do with this? And I've always been, at least in my head, critical of people who design without thinking about the impact of their work. I say that with a little bit of humility, though, because I do think that there's a lot that just unfolds over time. We didn't know, for example, that social media was going to do this to our society. We didn't know the outcome of that. We were looking at the positives of it. But now we know. So what are we going to do with that knowledge?

12:05Aarron:I want to rewind for a second to the critique part of our conversation because I think that's really interesting. And I'm kind of curious how you approach it with the younger generation of designers. So for some context, on my side, the place where we get to do critique is with students. And I have noticed over the years that it's become in some ways more challenging and rewinding in my own career to my college years in the 90s. I had many professors, one in particular, who were very good at giving critique, but also very sharp about it. And they weren't demeaning or cruel, although maybe it felt that way sometimes.

12:39Aarron:But they knew when you were bullshitting something and they would fully call you out on it. I think to some degree we've lost that skill. And then on the flip side, I think students are just so sensitive to anything that's perceived as a negative comment about their work. They kind of like internalize their work to a degree, even if you explicitly try to frame it that it's not about you. This is about the work that you've done. So I know older generations are always like, back in my day, blah, blah, blah. But how do you face that with your own younger designers?

13:09Eli:I don't interact too much with students these days. I do a portfolio review once a year at UCF, University of Central Florida. So that's probably my dose of super young designers. Our team actually skews mature like a lot of design orgs these days. So we're all senior product designers and principal and staff. So I think there's a seasonedness to our team that people are pretty accepting.

13:38Aarron:You think that's common? I see a lot of young designers in teams.

13:43Eli:Well, maybe I should get out more. I think in my previous, yeah, probably over the past five or six years, I think it's been probably harder. I would be curious if this resonates with you guys, but I would think it would be harder to get into the industry because the economy and roles have kind of compressed. People want to get more out of their roles. People aren't really hiring and wanting to train. it's really time consuming if somebody takes a design personally. You know, if they take it personally, you're set back probably like three or four days just on this one minor piece of feedback. I think it can be frustrating for a team that wants to move fast if the designer is, oh, poor me, I can't believe you said this about my work.

14:25Eli:My work is perfect. Like we are iterating so fast that you really kind of have to just take it and run with it and try to remove yourself from this process so that you can focus on making the work better. It is about the work. It really isn't about you. I think there's got to be a bit of humility there. It's hard to develop, but I do think the more senior you get, the more you kill your darlings and let go of those things that you find very precious. It's such a valuable skill, not just in design, but in life, right? Like your emotions, somebody's reaction to you, something you said. It's just a very valuable skill no matter what you do, but especially in the creative field.

15:07Aarron:So Cassie, your team at Medium did something interesting recently, which is to eliminate the PM role product manager. I have heard some other design leaders say something similar, But it strikes me as the thing that is not uttered out loud. I remember not too long ago where there just was not a PM role. But as our products and teams expanded, we had more complexity and we needed this middleman, middle person to kind of help orchestrate some of the things here. which creates a power dynamic. And I've literally seen this be a really negative power dynamic where there's kind of a person in the middle between engineering and design trying to claim space, claim respect when they're sort of like not making the thing, they're just orchestrating the thing.

16:04Aarron:I want to know why you chose to eliminate that. How do you bring that up in a meeting? How do you say we want to eliminate these jobs or this aspect of our workflow, how is that received and how do you work differently? I'll start just by saying that I don't think all PM, designer, engineer relationships are

16:25Eli:fraught or bad. You know, a lot of times that's a really generative relationship. Time and time again, when I interview designers, they're like, my PM is my closest bud. They're the person I bounce ideas off of. They're the person that makes my ideas stronger. They help me connect my ideas to the business. So it's not like it's a useless role or anything. I don't think the PM job is dead. As we were evaluating it for Medium, we were in this state where we needed to move faster. We wanted to make more product updates. And the state of our team was such that every single idea in the company was kind of being filtered through these three people and then being disseminated to a larger 30, 40 person design and engineering team.

17:08Eli:So that felt inefficient. I think we also had a lot of faith and a lot of signal that our designers and engineers could do some of that PM work, could look at our product holistically, could look at the results of our experiments, could look at our metrics and identify opportunities and also tie what the business needed to the work they were executing on and make it happen very quickly without drama. It's never an easy change to make, I think, when you're trying to do something that goes against the grain in the industry a little bit. But, you know, I think it was a matter of, are we doing this because this is just the way teams work?

17:50Eli:Or are we operating this way because it makes sense for us? And we sort of decided that it was worth trying. Maybe it doesn't make sense for us. Maybe a PM is more effective in a multi-vertical business. Maybe it's more effective in a business that has a lot of complexity to it. I think at Lattice, where I was at before Medium, we definitely needed PMs. And I worked with some amazing, really exceptionally talented, smart PMs. And same at Medium. They're really exceptionally talented and smart people, but there was a lot of complexity that I don't think we needed in a simple subscription-based business.

18:29Eli:So it's always hard to make a change like that. I think I had mentioned before, there's a human cost to it. Change is hard. There's this kind of feeling of the only constant in a startup is change, get used to it, you know, but you don't get used to it. It's not in your human nature. You want to have a tribe. You want to settle in with people that you work with. And it's really a constant thing that we're fighting. Let's be nimble. Let's try and adapt. Let's experiment. Let's try new ways of working. And if it doesn't work, we'll shed it. If it does work, we'll keep it and we'll keep getting stronger.

19:04Eli:So it's been a really interesting experiment and I'm really enjoying it personally because I get to see our designers and engineers taking on more than they were taking before. They take on more responsibility. They have more wind behind their wings. They feel like they're more empowered to suggest ideas. When I first joined, actually, we would bring up problems in the app and on the site and we'd be like, oh, well, how could we fix that? and a designer would bring up an old design that they already had that was all completely fleshed out and never realized in the product. I was like, that's a problem.

19:43Eli:If we have these design solutions and nothing is actually getting built, why? Why is that? And it wasn't the PM's fault. It was just this disconnect between what we were shipping and what our team felt was their responsibility. It's like, well, I designed it, so it's done. Or I did my job, it's designed. But it's this disconnect between our job is to understand the whole picture and to ship this. You know, if we're not generating value for the business, then why are we doing it? You know, we might do things for explorations or to try and understand something better. And maybe it gets us closer to something else that we shipped.