My guest today is Connie Yang who is the Head of Payments Design at Stripe. In this episode, we discuss the following: - Connie Yang Bio - Compensation for Design manager vs individual contributor designer - How to know if you are ready for design leadership - Improving your design craft before becoming a design manager - Demonstrating leadership before becoming a design manager - Focusing less on design work as a design manager - Why hiring only senior designers is a bad idea - Fear of getting a design hire wrong - Having performance related conversations with direct reports - Adapting your leadership style for different people - Unplugging and taking time off as a design manager - What if you realize design leadership is not for you - Managing your side hustles if you become a design leader - What do design managers get asked in an interview - How to contact Connie Yang For show notes, guest bio, and more, please visit: www.designmba.show
Connie Yang is a design leader with experience in consumer and fintech, and is currently the Head of Payments Design at Stripe. Previously, she led design at Coinbase and created products for platforms and global at Facebook. She enjoys asking questions and finding the bits of magic that surround us in everyday life.
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Namaste and welcome. I am Jayneil Dalal and you are listening to the design MBA which is a real-life MBA program for designers. You will learn how to launch a side hustle and level up your design careers from the interviews rock star designers.
Jayneil Dalal: Today's amazing guest is Connie Yang. Connie Yang is a design leader with experience in consumer and fintech and is currently the Head of Payments Design at Stripe. Previously, she led design at Coinbase and created products for platforms and global at Facebook. She enjoys asking questions and finding the bits of magic that surround us in everyday life.
Connie, welcome to the show.
Connie Yang: Hi. Just so happy to be here.
Jayneil: I got to say I love your sweatshirt.
Connie: Thank you. Thank you. You see this, right?
Jayneil: It’s got … for folks who are listening, it's got this bold thing “Why am I like this?”.
Connie: Yes, a great … a great question, “Why am I like this?” We should all ask ourselves and explore both inside and outside.
Jayneil: I think it's an amazing conversational starter. You just wear that and then people just start a conversation without you having to do anything.
Connie: Yeah. Actually, I like wearing stuff like that or having stuff like that. I like having prompts. I think people probably often want to talk to each other but are more often shy to approach or define something. So, if you're trying to like … if you have something quirky or weird going on, like “Hey,” makes you a little more approachable. It's like a different kind of user experience.
Jayneil: Absolutely. And I like about this quote “why am I like this?”, I think, you clearly pointed out, it's more about knowing why you're like a certain way and instead of fighting it, understanding that. And one of the biggest challenges that I’m personally going through and I know a lot of my designer friends are going through is this whole thing about “Should I be an individual contributor or should I become a design manager?” And it's a tough thing. It's a tough thing to figure out.
Connie: Yeah. A lot of people feel like that's like their main choice, right? In order to continue to progress your career, maybe you have to become a design manager but it's a pretty different job from being like an individual contributor as a designer. So, I get a lot of questions about that like “What is it actually like?” And yeah, it's pretty weird.
Jayneil: And I’m going to ask you a lot of questions that I’m curious about and I’m going to be so candid. And I’m probably sure a lot of people want to ask these questions but it's kind of weird putting this out in public or not have the right way. So, I’m going to ask a lot of dumb questions, by the way. Just a heads-up.
Connie: I love that. Thank you.
Jayneil: So, first question that comes in my mind is like “I’m going to be a contributor, Connie, and I want to become a design manager because I think that there's a lot more money to be made if I become a design manager and maybe a director, maybe go down that route.” There's a lot of money to be made that way.
Connie: Yeah, that's something that I think used to be more true than it is today. I think, now, because tech companies have realized, and I say this because I work in tech, so it's the area that I’m the most familiar with, but tech companies have realized if everybody who's a great designer then becomes a design manager, there's nobody left to actually create the designs, right? So, you don't actually want to encourage it that way.
Jayneil: Who's going to do the work?
Connie: Right. So, the philosophy that many of these companies have developed is whether or not you are … there's levels, that's a pretty common thing, right? You're like … there could be a level one, two, three, four, five. And at some point, your levels continue growing whether you're a manager or an individual contributor. So, they've equalized salary bands and compensation across these things. You could be a super senior designer and be making as much money as like a manager. It's just like the bands are the same. And we try to just keep it to skill and experience, not really about whether you're leading a team or not because these are very different skill sets and very different ways to spend time. So, we recognize that both of these are unique and difficult and try to reward people well no matter which path they want to be. Being a really skilled senior contributor is awesome and super, super needed by so many businesses.
Jayneil: But the only exception to this, and you can correct me if I’m wrong, is if someone is the VP of design, a very senior post, they might be still making a little bit more than someone is a very senior individual contributor.
Connie: Yeah, that's a good … that's a good point. I would say for those types of roles, it's almost akin to like if somebody has an exec role at a company … it's kind of like … who knows, right? It's really based on negotiation but who knows what your equity or outcomes … that's like … a founder might be a design founder but they're definitely compensated differently than somebody who's hired much later, right? That just becomes kind of a different stratosphere of compensation and pay bands but I’d say for the standardized stuff, companies try to keep it really, really equal.
Jayneil: So, you've been an individual contributor in your career, right? And then, now, you are an … you're now a design leader. So, what changed? Previously you were an individual contributor, you were doing certain things, focusing on certain areas. And then now, you're a design leader. So, what was the biggest change or what are some things that changed for you?
Connie: For me, I … I don't know … in my personal career, I don't know that I ever made a decision to become a manager, which might be strange to think about, but I’ve had a lot of different jobs. I’ve been working in tech for nine years but I’ve also worked in gaming, in advertising, and in print design, graphic design. That's how I actually first started out. And I was always either the most senior or maybe the only designer at whatever company I was at. So, sometimes there would just be too much work and then we'd have to hire another person. And if I’m the only designer, they're like “Okay. Well, you have to hire the person and then you have to manage them.” So, I’ve been a manager maybe … I don't know … five or six times in my career. And it's … the first few times kind of happened merely by necessity. So, it's like “Okay. In order to do more work to get more stuff done, we need to hire more people.” And that's how that kind of started. So, it really was like … it felt very natural and necessary in that stage. The one time I made a really conscious decision was actually to not be a manager, I actually, after several jobs of being either the most senior or the only designer at whatever company I was at, I really wanted to build my design skills as an individual contributor and this was … gosh! Like 2012, maybe 2013. I was like “Okay, I want to become a better designer. I want to go to the place that has the greatest density of good designers that I could find at the time.” And for me, at that time, that was Facebook. I thought Facebook design was super cool. This was back when Facebook was like 3000 people, much smaller, a very different company than it is now and the design team was maybe 45 people at the time. And I remember looking at profiles of different designers that worked there and just feeling super impressed like “Oh, these people are like really, really great. That's where I want to learn from.” So, at that point, I consciously decided “I’m going to come here and learn design and learn to be a better designer from other designers.” And so, I spent a number of years there just working on the craft in that way. Then afterwards, I went back to leading teams and managing because I really like working with people, I really like mentoring, coaching, I like building out like a culture and trying to affect change and create bigger products and solve different problems at scale. So, I feel inclined to do that just based on like what I like personally as a person or as an individual design human but …
Jayneil: And you mentioned this amazing thing that it's really rare that when I talk to people like who have opportunities early in their career to become manager but purposefully decide not to pursue them and instead focus on the craft. And you could have gone the other direction too. You could have just decided that early on “I’m not going to focus on the craft. So, I’m going to become a manager very early on and grow in that and create that track.” So, what I want to know is has that choice made any difference for you like the fact that you took some time to focus on your craft, really become good at it, before becoming a design manager. Do you see any benefits of that route?
Connie: Oh absolutely. I mean, I still think like … the advice I tell people who are like new grads or first trying to enter the workforce is to work at one of these big companies with really well-established design teams, design systems, processes in place. You can learn so much, right? And in the time that I was at Facebook just learning from how people … the basic skills, give and receive feedback, think about problems, work with like a cross-functional team really deeply, how do you work with data science, how do you work with research like … There's so many of these basic skills that even if you had experience in them before doing it at a company that is also really, really good at it, helps you so much. I think it's really a good path. Even if eventually you want to work at startups or smaller teams, go and get the big grand experience of companies who've really done this for a long time and then take it and then use those skills at these smaller places who would benefit from your experience because they don't have that built in.
Jayneil: Wow! So, it's kind of like you just let the natural progression dictate when it's the right time to become a manager because … I’ve talked to a lot of folks and I’ve been guilty of that too where it's like you set out with a goal, you're like “Oh, I want to become a design manager,” “I want to become a design leader” and then you just work backwards without really letting it become natural and then everything becomes this thing where how can you get promoted the fastest.
Connie: Yeah. And I think if … you should definitely … If you're on a team and you have a manager, you should talk to your manager about these ambitions and they can help you out with that but it's usually more important to build those skills as a leader. One thing that I learned early on in my career … because I was pretty ambitious. I was like “I do want to do these leadership things.” So, I didn't really … I wanted that promotion. I wanted to feel I was doing well and succeeding but I didn't really know that there's a difference between being a leader first and then incidentally later you could become a manager but you have to build those skills and demonstrate those skills before you can be promoted before people would trust you to have that kind of role. So, things you can practice with like being really responsible with communication, organizations, sending out updates, taking … being the DRI, the responsible individual for certain projects. There's lots of ways to demonstrate leadership without actually being a manager and try it out, see if you it because you're going to have to do all those things and more if you actually want to be a manager. So, there's ways to build up those skills. And I’d say, everyone, even if you don't want to be a manager, you should still build up those skills because it can be useful just in your life even beyond just your design work.
Jayneil: So, now some things I’m just wondering … this is just me thinking as an individual contributor but me trying to put myself in your shoes as a design leader and these are some questions I have. For example, if I’m working on a Figma file and I’m doing some things, I know how much time it takes me. Maybe I’m fast at it, maybe I’m at a certain pace but now as a design leader, when I hand this task off to someone and they're taking twice the time as me, how should I treat that because suddenly it's like I’m an individual contributor turned new design manager and I know this can be done much faster but this person on my team is taking way longer or maybe they're not focusing too much on the visuals like I’m used to. And that's the bar in my head. So, as a design leader, how should I think about these things or the design manager?
Connie: Such a good question. Yeah, that's a feedback I hear a lot from people who have just become managers. A lot of times … not every time but a lot of times, a person who first becomes a manager, maybe a pretty senior designer or somebody who has a lot of experience or is really good at their craft, their job and then you simply shift that and they relinquish their design part, they're not actually doing design work anymore and then they have to rely on possibly more junior designers or people who aren't as experienced, don't have as much context, so it's going to take them more time to learn. And I think an important thing to keep up is yes, maybe you could individually do something faster but that's not your job anymore. Your job … because if you spend all that time doing design work, then you won't have time to actually manage a team and lead the team, right? So, you have to have someone else do it and your job is to help them grow. It is to make a good product and think about that but your job is to think like “Okay, what stage are they at with working on this? What stage are they at with thinking about this type of problem?” and “How do I encourage that growth?” And sometimes, it's okay to not have something be 100% perfect all the time. Some of it is these individual designers learning through their own process, right? You can't control … as a manager, you can't control the outcomes. You can only steer, provide guidance, provide feedback. And if sometimes a project gets to 85% or 90% but then it's done and then you move on to the next thing, that's still better because as a team you're still doing more work. And as you're leading your designers, you all are getting more stuff done and that's important thing. You hire more designers, you grow a team because you want to do more things, right? And that's an important goal to keep in mind. And keep your quality. I’m not saying don't do good work but it just changes, your goals change, your internal barometer of what you need to do and what your team needs to do changes.
Jayneil: So, it seems like as a design manager, my goal is to grow my team, grow the individuals in my team, clear the roadblocks in their way so that they can deliver great design and kind of like it seems like my job is to just make the perfect design operating system where all these designers can come and grow and create the best work. So, in this new paradigm, the new goals that I have as a design manager, what if I get obsessed with getting each design presentation perfect and like telling this junior designer on the team who's just joined like “Oh no, make this change, make this change.” It's kind of hard to let go because previously, I would have done all these changes myself like trying to make that perfect alignment right. I know it doesn't matter. I mean, the goal is just to get this presentation out to the leadership but I can't help it.
Connie: Yeah. I can totally understand feeling that way. I think it's important to figure out what are the key things you'd want to focus on. If you imagine like if you're first learning something and it's something hard and the person you're learning from is telling you to change that, change this, change that like a thousand different things, it's overwhelming and it's a lot and it's not the best environment for the person trying to learn whereas if you're told “Okay, here's a presentation and here's one key thing. Let's improve the overall consistency of the layout” or something, right? If you pick one thing, the most important thing and be choosy about what that is and what makes a difference for this particular project and have people focus on that, you're not going to get everything right but figure out what's important because people can really only grow and sort of adapt to a few things at a time, not everything, right? You can't have an expectation that you're going to go from 0 to 10. If you're starting at 0, and most people actually aren't starting at 0, go from 0 to 1 and then from 1 to maybe 2.5 but you have to go that way. You can't just expect everything. These are possibly new designers, right? They don't have the same experience. You're a very … you're perhaps a very experienced very senior designer. It's different. Remember how you were when you first started, right? You can't get everything right.
Jayneil: But then a counter argument would be why not just hire all senior experienced designers so that I don't have to, as a manager, coach them or something. They know what to do. It's like these are other rock stars. Just hire rock star designers. Then I don't have to manage much. They know what to do and everyone's happy.
Connie: Totally, super tempting. I mean … why not … if you can find all rock star designers, go for it. There aren't that many of them, let’s say. Sometimes they go into … evolve into something else. Sometimes they become managers unless they go and start companies, agencies, who knows, right? There's not that many who still want to do that job. So, you do … you just can't hire only senior designers. If everybody could, I’m sure, maybe they would but I’d say, you do want … you have different stages, different types of problems you want to solve, right? Sometimes you need a really gnarly like six to eight-month strategic problem that you need a senior staff designer on but sometimes you have like “We need to build this app or this process and it's not that like different or we need …” It's more like execution. Well, a senior staff designer isn't going to be super interested in that problem. So, you need people in different levels because you have problems of all different levels. So, that's another thing to consider. And you do want people to grow, right? You want people to grow with you, to grow in your company and to stay because once you build up that context, it's helpful. So, there is a huge benefit to growing more junior designers or mid-level designers because you're still able to teach them, you're still able to learn. If you're also … like someone's at a stage where there's not much for them to learn from you, that's also not very interesting for them. And the last point I’ll say is, and at some point, that's really important to me, if you're at all interested in thinking about diversity and representation in the design world and you want to employ a greater variety of designers, you're going to often find them more at the more junior stage, right? Because the people who've been working in the industry for 10 years or so may look a certain way and it's like the newer people that are starting to learn, that are beginning and don't have the same skill set yet perhaps or they're still getting there, and if you want to make a difference or help people along or change the perception of … the perspectives within your team, you might have to hire more junior people and say like “This is how I’m going to affect that change. This is how I’m going to help others. This is how I think about diversity and why that's important to me.” So, I think there's so many factors as to why it's good to have different levels of designers on your team.
Jayneil: I am literally feeling paralyzed right now thinking about if I had to make my first hire like … I mean you made so many hires. Now, I’m just wondering, as a design manager, you will never know like this person is a perfect hire like things could go wrong, things may not work out. So, doesn't that paralyze you, that fear like “What if I get this hire wrong and all this time wasted? Should I just wait and wait forever to get the perfect tire?” What is your take on that?
Connie: That's a great question, definitely a question faced by a lot of design leaders, especially if a company's growing really fast, what we call hypergrowth in tech. That’s a question I grappled with myself a lot, especially when I was building out the team at Coinbase because we really needed to hire … like the team went from … like my team went from three designers to 22 designers in a year and a half and that's a lot of growth from a really small magnitude. And in the beginning, I had the same questions. I mean, I still always have those questions like “Is this person a good bet? Is this person …” like you never know, right? All you can do is make a judgment based on your interview, based on your assessment. And then at some point, I think, the faster you need to hire or the faster you need to grow your team because the rest of the company is growing or you need to do more work, I think, you just take on more bets. And you can recognize that if it doesn't work out, it's still a conversation, things can shift, things can be … you can still alter the team and you can … or you can hire someone differently. There are things to be done. It's not like hiring someone is going to be like “This is a five-year, 10-year decision,” right? There are ways that we can work through different problems. So, I think you just have to decide “Well, let's … I think this person's mostly right. I’m like 75% sure. Maybe that's great.” And maybe if you're not in as much of an urgent rush, you can say like “I’m going to wait till I find someone that I’m 90% sure about” but at some point, you just change like you're just like “Oh. Well, actually, we do have to go faster. So, let's try. I think this could work out. I think it's a good chance. Let's try it.” And then figure out what happens if it doesn't work out. You just can't expect everything to be perfect.
Jayneil: So, let me ask you this. Have you ever had this scenario where you hired someone and they were not living up to the … no, I wouldn't say potential but their work was not at par what you expect of them? Did you have to ever have a tough conversation like that like “Hey, listen. You're not performing like we expect you to” and it's kind of more of like those the PIP talk like performance improvement plan like have you ever had to have a difficult conversation like that with someone you hired?
Connie: Yeah. I mean, I don't think that's any manager's favorite part of the job but it is something that you should be prepared to do.
Jayneil: I bet it sucks.
Connie: That's like a … yeah, I think, the way to do those is to keep it focused on growth and learning, right? I really believe it's like finding someone to work at the company for you. It's definitely a two a two-way conversation, right? I want to make sure that they're great for us but I also want to make sure that we're what they want and we’re what they're looking for. So, I’m always very upfront about “Here's the good stuff. Here's the challenging stuff.” I try to be real …
Jayneil: Oh, you let them know upfront. Wow!
Connie: Absolutely. I mean, every company has good things and bad things, right? There's no company that is perfect for all of the stuff.
Jayneil: Like what could be an example of a bad thing? For example, if you were hiring someone, what would be the examples of a bad thing? I’m just kind of curious about it.
Connie:Yeah. Maybe I shouldn't say bad but there's different …
Jayneil:Challenging. Challenging is the right word.
Connie:Yeah. I’ll use my current company Stripe as an example. Stripe, for instance, has a really … there's a culture of writing in like documents. There's a lot of like people making comments, a lot of our specs are in written form. It's kind of … some have described it as an academic culture and … I’m not saying this but actually I like that. I like the quirky academia kind of vibe for it but that's not for everybody, right? Some people are like “No, I really, really don't want to do documents” or whatever it is, right? I think it become kind of individual choice there.
Jayneil:I see.
Connie: It could be like a different preference like companies will have different cultures. So, I try to be really upfront about that stuff. So, that's one example, for instance.
Jayneil: So, you do a lot of work upfront to make sure that the candidate fits with the culture, they have an understanding of what to expect. And despite this, if still for whatever reason they're not performing up to mark, then you have the tough conversation with them.
Connie:Absolutely. I’ll just say that I try to frame it as like “Okay. So, this is the type of here are the expectations, here's where you are now and is this what you want?” Some people … I wouldn't say people are bad performers because they're simply unskilled. Sometimes it's not the right fit. Sometimes they're like “Oh, actually, I realize I don't want to work at a small startup. That's not what energizes me.” And I really want to make sure … it's almost kind of like a coach-oriented position. I want to make sure they're in the right place for them. It's like “Is this actually what you want? And if it is, awesome. Here's a plan that will get you there but if it's really not, no hard feelings if it's not.” I just like efficient systems. I want people to be happy at where they are and I want the places to be happy with the people. And that may not match up all the time. And that's okay.
Jayneil:Oh my god!
Connie:I think there's no harm or sadness in that. I think it's always better for people to find what they actually want to do.
Jayneil: So, let's say the hypothetical scenario, I am your direct report … because I’m just curious how does this pan out. I’m just very curious because I’ve never done it. So, if I am your direct report and for some reason, I’m not performing and you've seen this multiple times, maybe you let me know indirectly a couple of times like “Hey, Jayneil, this needs to be this way. This needs to be this way” but still we're having the conversation. So, let's say that today you call me into your office or you're just having a Zoom call to give me the hard news, whatever that might be, how's that conversation going to go according to you? You will just give it to me directly or you'll ask me questions or is it going to be … I mean, I’m not asking for a template but I’m just trying to … or maybe I am, I don't know.
Connie: Okay. it's a funny question, I would say. So, your scenario here is like you've already been told that you need to improve certain things and you haven't done that, right?
Jayneil: Yes.
Connie: That's your scenario.
Jayneil: Yes.
Connie: That is very challenging. So, at most big companies, how PIPs work, which you mentioned, performance improvement plans, is you're given the plan that you need to hit essentially, right? That's what the plan is. And for me, I’m a person who really likes specific structure. So, if I were making this plan, I would say like “Okay, you need to … the things we talked about your visual design is good and that's 4 out of 5. Your prototyping though is it 2 out of 5 and your communication is like a 3 out of 5.” I actually making structured points and I have to … and I will say “Okay but to get to your next stage, your prototyping needs to go up to 3 though” or You're at this …” I really try to break it down into like the specific things you need to improve and then do frequent check-ins. And so, if we're at the check-in where it's like “Actually your prototyping is still at 2 and we talked about these things to improve them. Did you try those?” I’ll make it really explicit like what to do because I really tactical things because sometimes it's hard to think of like “Okay, need to improve prototyping but what do I do to do that?”, right? And so, it's really helps to have specifics. So, I would try to keep the conversation like really focused on “What did you try? What did you not try? What's working? What's not working?” or if somebody just didn't try, I guess, like “Okay. Well, maybe they're not really … they're just … their heart’s not into it. Maybe they actually don't want to do it” and that's okay too but I’ll say like … if what you're asking is just how to structure that difficult conversation, I just want to make it clear. It's like “Okay, we talked about these things. Did you hit them or not? Did you try it or not? Why?” And I try to understand like what they're thinking, what their motivation is and see where that goes. That's actually the conversation is far enough along where it's like a really unfortunate conversation. At most companies, HR is also involved and there’s sort of like an actual template which … that's challenging. That's nobody's favorite. So, that's how I think about these types of improvement plans.
Jayneil: But I got so much insights on the way you're approaching this. It’s like you're breaking this down on a tactical level. It's not just this feedback like “Hey, you know, Jayneil, I think you need to work a little bit more in prototyping skills.” It's not vague like that. You're very specific that “Hey, on a metric of 0 to 5, this is where you're at, this is where you need to go and this is tactical feedback how you can do it better.” And I’m almost wondering now was Connie always like that like very meticulate about task level. Was this something that you picked up along the way along your journey? Because I mean, it's a very helpful skill to become a manager.
Connie: Yeah, this is probably because I used to play a lot of RPGs when I was in high school and in my early 20s. So, I really liked systems and specific things like where are you putting your skill points like where are you, what have you like what have you grown. I make jokes all the time just even in regular life about it. I personally have a really terrible sense of direction and I joke that I just never allocated any skill points and directions. I’m at zero directions. So, for me, these are … I find these to be helpful structures. I find everything to be more helpful if it's broken down. I’ll say I’m an example about levels. Most companies will have a level. And some levels are like if you're in like a mid-level … mid design level say like it's maybe an IC3 or an IC5 at some companies, depending on their system, everyone would be like “Okay, how do I get to the next level?” That can feel like the big question and that can feel like … but most people aren’t going to just get promoted all the time, right? It takes time, it takes work, it takes experience but every time you're like “Okay, if I’m at this level, do I get to the next level, do I get to the next level?” It's maybe your ambition but then you just feel not good because you just haven't gotten there yet whereas I think it's much more helpful if you have say this like IC3 level to break it down like “Where in the IC3 level are you? Are you IC3 early, are you IC3 mid or IC3 late stage?”, right? So, then it's like if you're early, then your goal is totally not to get promoted to the next level. Your goal is to get to mid and what are the things that we can talk about to make you more of a senior or mid-level design for your level. Does that make sense? I think little ways of breaking down, just make it seem better, right? Your goals should not just be always the huge next level but what's the actual incremental step for you. And then if we have ways to measure it, I think it just helps people feel better like “Did I actually accomplish that or did I not? Am I growing or am I not?” I think people want feedback and they want consistency in being able to understand if they're doing the right things, making progress.
Jayneil: I’m going to be super candid with you. I’m the type of person that when it's traveling, packs my bag like an hour before, two hours before the flight. I mean, I’ve improved, I have a checklist of things I made last night like things I need to take but it just pretty free-flowing, maybe it's because I have ADHD, I just kind of like going with the flow. There's not much structure. There is some structure to kind of make sure I don't get in trouble in the airport but then I’m just like winging it, a lot of things. The more that I talk to you, it seems to me that becoming a design manager is a lot about designing practices and processes that help others grow, providing a lot of feedback and … I’m not saying that this thing's turn me off or maybe I shouldn't even say that but it's just like … I’m coming from that freewheeling traveler, just go to like Venice Beach, pack everything, let's go, we'll figure it out. Everything is a wing-it mindset and then here what I’m hearing is more of like … the manager version of it is like “Okay, we're going to book the flights in advance. We're going to have a structured itinerary. We're going to make a list of all the museums we're going to go to” and I’m just kind of wondering is there even any hope for me or someone like me who's used to doing this task in this IC role and not have to do so much feedback and processes and structure and … I don't even know if that's a scale that I can learn or … I have no idea, I want to say that.
Connie: That's so funny. Even the way you're describing like “I’m going to go make a list of museums,” I’m like “That sounds great. I would love to go to all the museums.” That's just how I travel. So, I would say … caveat, the way I’ve been describing everything as like I’m also a very … I do like to plan ahead. I do like to make sure I’m going to all the places I want to go to. So, that's just my personality, right? I’d say the structure of like breaking things down into skill points or whatever like … I don't really hear about other design managers doing that. Maybe there's someone else who's also played RPGs and maybe that's why they're doing that but that's maybe more structure than that I’ve heard from most people. So, there's of course different management styles …
Jayneil: But that's what makes you so good because I work with the manager exactly like you. And the benefit of that kind of style is that I always know what to expect like … I’m just telling you from someone on the receiving side of having worked with someone like that, it's … I exactly know what the feedback is going to be, how they work. It's almost like I have a template on how their mind works. I’m not in the limbo.
Connie: Yeah. And that's great that that works for you but I’ll say not every designer likes that, right? Some designers want more openness or less specificity. Some want to work super autonomously, only check in once in a while or some really do like that system or some just want a manager to talk more about … I don't know. Maybe it's like their feelings that … who knows? It's a variety. Nobody's the same. And so, you also sort of try and like not necessarily adapt your basic style but to really at least be aware of what works for each individual. When I have a new person join my team like one of my direct reports, I do a little questionnaire. I also to ask a lot of questions. So, that's again … this is me. It's my personal style. I’ll ask questions what do they think about it as their career pinnacle like what do they actually want to aim for, how do they think about their goals, what makes them mad, how do they like to receive feedback or receive praise. I just try to get a little intake on their personality to really understand, even questions that sound like they're not really like work related like what do you do to … what's your favorite thing to do to decompress when you're having a stressful time or things are too busy or too much. So, I think it's just helpful to understand what makes each individual tick, right? Some people like to receive feedback only … even if it's positive feedback, they want to receive praise just one-on-one. Some are like “Actually, yeah, it’s kind of nice if I get a shoutout in like a room” and like different people have different preferences.
Jayneil: Oh my god! So, you are also adapting your management style depending on who the direct report is, what are their preferences how they like to receive feedback. Oh my god! It's continuously changing.
Connie: I mean … yeah, it's something just to keep in mind. I wouldn't say it's like I’m changing my personality or whatever every single time I have a different one-on-one with somebody. I’m still me but I try to be aware of what different people respond to and I think that's something that is helpful but I would say it's most … one thing people should remember that managers are also pretty busy. Sometimes we're very scattered and we forget or we don't keep up with it. And I find it super helpful when my reports come to me with specific questions or they're like “Oh, I really want to have feedback on like …” I don't know … like “my presentation style” or something. And then I’m “Okay, cool. That's awesome that you thought of that proactively. Here's my thoughts on that,” right? Because it's best when it's a two-way street. We are trying to be as aware and attentive as possible but there's a lot going on. And, of course, we're very imperfect. So, the more like a report can help in like … sometimes people call this skill like upward management. The more they can like share “Oh, here's the things that we need to know” or surface the problems to us, we want to help. We're here to help. That brings us joy. That's why we're managers but we don't always know what the problems are, what's going on the team. So, the more that your reports can tell you, surface to you what you should know and what's challenging, the more we're like “Great. Cool. Those are the problems. Here's how we tackle them.” That's cool. Then we get happy.
Jayneil: So, let me throw another scenario at you. And you're going to be “Goddamn! This dude! Scenarios upon scenarios” but as an IC, I’m having an off day, maybe an off week is the right word like something happened in my life, I’m just … I’m not feeling it for the entire week. And my designs are not due two weeks from now. So, I guess I can have an off week and make sure I still get the work done but, stepping in your shoes, there's so many people looking for your feedback, approvals, processes, just paperwork. There's a bunch of stuff that has to go through. So, if so many things are dependent on you as a manager, what does an off week look like what do you do then? I mean … it seems to me that I can have it more easily because I just got to make sure my project work is done but then it's not like I’m plugged in so many different directions and calls and meetings after meetings and I got to be active. So, how does someone you deal with like an off week?
Connie: Oh, that's a good question. It's funny. I don't think I’ve been asked that before. Actually, I would say like well, how does someone deal with taking a vacation. Managers take vacations like other people and they're not there sometimes. So, it it's not so different from that, right? Sometimes it's like “Okay, for this week, I’m going to delegate these things to these people” or maybe you have to … if you're gone for a week, you skip some one-on-ones with people and that's okay, that's normal, right? My reports are gone for a week or two. I skip those one-at-ones. That's okay. So, it's really about knowing what goals … what's really important for that week, what still needs to get done and making sure there's either a decision that's made on those or someone to make that decision or someone to talk to, to direct or whatever it is. So, it's really … it becomes like delegation. It always … it's making sure that people always have a path forward if they need you for something. Sometimes people will like … right now a lot of people are on Slack. In your Slack status you can say “I’m out sick for the week” or “I’m on vacation,” whatever it is “But here's a doc that you can reference” and you can write down “Oh, here are the things. Here are the people you should talk to for each one.” And so, it's really … I don't think that it's that different. If you're having a week where you're not able to be there, make sure the stuff can get done and people know who to talk to. You never want to be the reason a project or a decision is being held up or you could decide maybe “This thing actually doesn't need my stamp right over there” or “Maybe you can just talk to this other design team” and that makes sense because we're collaborating. So, it's … there's no set way to do it. Lots of different solutions. Just make sure …
Jayneil: I guess, what I’m trying to get to is if I’m missing the ball on something, if I … let's say my designs were late a little bit. You will just give me feedback on slack “Hey, Jayneil, I heard from the engineering manager that you didn't deliver the designs. Can you please send over the files?” So, it's like you'll give me the feedback right away. So, that's how you're helping me make sure things don't fall through the crack because it's not only my to-do list but then you letting me know if you hear from someone else but since as a manager you are plugged in so many different directions, there must be some fear of making sure things don't fall through the crack. So, I was just trying to figure out like there's that fear of not letting things fall through the crack but then you're like … someone's having an off date, so it's kind of a little bit natural to like … some things just might fall through the cracks. I just kind of wonder if there's some fail-proof way you were applying or just … maybe it's not that crazy if things fall through the crack, I guess, for a design manager.
Connie: No, you don't really want things to fall through the cracks but mistakes happen. We're still human, right?
Jayneil: Exactly, right?
Connie: So, there's nothing … you try to learn from it, right? You try to like see “Oh, this is what happened.” And I also try to remind people of the broader scale of things like let's say like “Oh, shoot! I was supposed to make a decision on this and I totally forgot, it just fell off my radar.” This happens. I’ve definitely done this, right? And then something gets delayed but usually someone will ping you, somebody could be like “Connie, we need a … we got to look at this.” And so, I appreciate that because we have so many Slack messages, so many emails that sometimes we do miss something that is on a certain time. So, I really appreciate communications that are like “Hey, Connie, we need a decision on this by Thursday because we need to get this to whatever vendor” or “the next meet” or whatever “by Friday.” Super clear versus just like “Hey, Connie, can you look at this?” That's confusing to me. I mean, it's not just confusing. It's just more like “Okay, yeah, I’ll look at that but later” but if I know the exact time and reason, then it's so much easier for me to be like “I do have to prioritize this. Okay, I will look at it.” So, I do appreciate that but I’ll say even … let's say in spite of that you miss it anyway and nobody has let you know, depending on what industry you work in … yeah, it's tech, it's building products and these products are important but you're not like a paramedic, you're not like …
Jayneil: Yeah, like a surgeon. Yeah.
Connie: You're not doing those things, right? It's not you didn't do this and now this horrible tragedy has happened to somebody's health. And that's not to say like … we work in payments infrastructure, we want to get … businesses do rely on it. So, it is really important but it's okay if something shifts. Very rarely is it so fundamentally not okay that something catastrophic happens like … it’s good to remind ourselves of where we are in these places like “It's okay. Things will still run. We'll find a way to work around it. We'll find a way to like work to the next one. What did we learn? What are we going to do better or not do next time?” I think that's always important. It's important to find a way forward.
Jayneil: I definitely love that you're saying that it's okay if people make mistakes. Nobody's perfect. Now, what I’m wondering is given the fact that I told you I’m a wing-it traveler packing at the last minute, how would someone like me know that “Hey, I can try to become a manager, maybe try it out” because the thing is you can have all these things in your head like “Maybe I could become a designer manager, maybe I like it, maybe I’m not sure” but then when you really try something you know, “Okay, I tried this and I knew that this wasn't for me” and the embarrassing part about this is that … I feel in my head that's a little bit embarrassing that I say that “Let me try becoming a design manager,” maybe that's an opportunity, I take it and halfway through I realize that “Oh my god! It wasn't for me” and I would have rather wished that I had known this without actually going to that position and figuring it out.
Connie: Yeah. On the same vein of like making mistakes … it's not even a mistake, right? I think it should be natural like … mistakes are okay but also if you try something and then you decide you don't like it, that's okay. Actually, at Stripe we have a lot of design ICs who used to be managers and then they're like “Maybe I want to switch for a while” to just go back to doing like IC work and that's totally fine, right? It's not they made a mistake by doing that. I think it's a natural part of the process to try, to try different things. And also, there are ways to try it out like … if you're really not sure, there's so many ways to simulate some of the skills that you'd have been practicing as a manager, right? A common way to do it at these companies, one is to mentor other people. You can cross mentor other designers on the team and just see like “Oh, if I have a consistent mentor relationship for a couple months, how did I feel? Did I like that?” Another very popular way to do it, at bigger companies … companies are big enough to support design interns is that interns are usually given to more mid or senior ICs to manage for a summer or a season or whatever it is. And that's a very explicit manager like …
Jayneil: Wow!
Connie: … time, right? Because they're reporting to you for that period of time. It's bounded. So, they're … and there's no obligation, you're still an IC. So, there's lots of ways to try it out, more so probably at bigger companies who can support these systems at scale but yeah, there's ways to try it out. And even if you actually try it out like “Hey, there's an opportunity to manage a really small team” and then you later decide you don't like it, that's okay. That's okay too.
Jayneil: I love that. It's almost if I was a direct report and I told you “Hey, I’m not sure about this” and you're almost like “Hey, you know what? Next week I’m doing these things as a manager. Why don't you take care of this one thing and let me know how you feel?”
Connie: Yeah.
Jayneil: And that would give me some kind of feedback that “Hey, Connie. So, I know everyone tells me that I should become a manager but then this task that you gave me for three weeks to kind of do that you do as a manager, I don't think I’m liking it that much.” So, there's that feedback that I’m getting without even stepping into the role.
Connie: And that's a great way to try it. It's also good to like … management is so many different tasks like maybe … it's like maybe I had you lead a stand-up and you're like “I actually don't like leading stand-ups.” I’m like “Okay.” it doesn't mean you don't want to be a manager. There's a lot more to that, right? So, we can always try different things so that there's no like one single …
Jayneil: Oh wow!
Connie: … key to it but it's good to … it is good to try. It is good to try. And as a manager, you probably … you will have to lead some meetings, you will have to do some communications. So, there's some things you have to do. You may not love all aspects of it which I don't think I know anything, I just love all aspects of it, but there's a … so, whether or not you want to do the rest of if it enough or you're still like “Okay, yeah, but I’m cool with doing the other things that I don't like as much.” That's the kind of important stuff to figure out.
Jayneil: So, the biggest thing I’ll say is there's a lot of folks me … oh my god! I’m just figuring out how to phrase this … but I have a lot of side hustles that I do. And one fear that I have is that if I were ever to step in your shoes and I have all these side hustles that I’m passionate and I’m not willing to let go, whether that's exploring the WEB3 in crypto world, whether that's doing the podcast, just whatever the side hustle is, as an individual contributor, just the way it's structured like, right? I don't have to be in meetings all day like you like as many meetings as you, I would say, or always be plugged on like as long as I get my work done on time and it's … the standard requires me to be, I can easily very quickly switch my focus from like work, after work quickly to side hustle, I’m not completely exhausted or drained from all these meetings, talking to people. So, I’m at that point where I feel like … my mind is if I ever want to become a design manager or something, I have to give up all these side hustles and that's like … I don't know … it's scary. So …
Connie: Yeah, I can definitely understand that fear. I really think whether or not you have these side hustles going on, it depends on you as an individual, right? Management is like a job. It's like other jobs. I see it's a job. So, there are time boundaries that … you should do the best you can to like own your own time, right? There's like … we don't just … because you're a manager doesn't mean you have to work an insane number of hours. It may mean you have to work smarter, maybe you have to delegate more or you have to be more efficient about certain things. And that's a great skill to have just to figure out how to learn or how to operate more efficiently. That's great. You can still make time for it. You might … the hustles you want to do may change. You're right, I have a lot of meetings per day. I do a lot of talking or listening. And so, that might mean … well, actually, then my side hustle maybe I don't want to do more talking. So, maybe then hosting a podcast is not the side hustle for me but maybe my side hustle is going to be like knitting or … I don't even know.
Jayneil: Oh wow!
Connie: I don't know why people are would change that. I mean, that's just an example. I don't know how to knit but I think it's totally up to the individual. You can manage your hours. You should know what the expectations of your job are and do them but that can still be done in a finite amount of hours. And then what you do with your extra hours is totally up to you. So, it's really like you craft your own life, your own career however you want.
Jayneil: This is eye opening for me because I’ve seen design managers that I worked with that would sometimes log in on Saturdays to take care of this because during the week, there was so much in meetings and there's all these pending approvals and whatever, some stuff that fell through the crack. I would see emails on Saturday like they took care of it. And they love doing it, don't get me wrong, but now what I’m hearing you say is that it is possible to be a manager … I mean … I’m not saying every manager is this but I’ve seen the fair often many managers sometimes on weekends that will answer something. So, it's … in my head, the mental model is still as a manager you might have to put in some extra hours after work or the weekend just to make sure nothing falls through the crack.
Connie: Oh, that's funny. Well, I’m more of a time flexible person like even though I will like … I might respond to an email on a weekend or an evening or respond to a Slack message or send a Slack message because … I don't know, I’m kind of flexible like I’m using my phone, I happen to see a Slack message and I’m like “Okay, might as well respond.” It's not … I’m not so bounded where I’m like “It's past a certain time. I can't look at this.” I’m not that kind of person. I’m a little just more flexible about that stuff where some people like … maybe they really want to clear the mental space or really have a clear separation between all that whereas I don't have as much of a separation. And this is totally personal choice, right? But you can also like … oh, an example that I remember hearing from my time at Facebook, Sheryl Sandberg … incredible, incredible leader. She would frequently make it a point that when she was like raising her kids early on, she'd left at 5 like she would just keep that boundary very firm so she could still spend the time with her kids that she needed. She still got her job done. She was still great at it and she has a much more challenging job than most people in the world. So, if she's still able to do that, great. And she ran events, she hosted things, she definitely had like side hustles. I don't think she would call them side hustles but she did a lot of stuff that was outside of her main role at Facebook. So, if she can do it, anyone can do it. It's just how you prioritize your life at your time. Did she respond to emails later on the weekends? I actually have no idea. I didn't email her that much but whatever she did worked for her, right? Whereas sometimes, I’ll be … I’ll check Slack before … late in the evening, I’m just like “Yeah, what's going on? What did I miss? Is there time for me to respond?” I’ll do it or sometimes I don't … you don't have to though. No one's saying you have to respond to Slack within a certain … 12 hours after receiving it. That's not there but it's also not difficult for me to look at that stuff at different times.
Jayneil: This is extremely helpful. Let me tell you one last fear that I have is, as a digital contributor, I’m always in the loop with the latest design tools, I’m using it, I’m fairly familiar with it, my portfolio is updated with new projects I’m putting on it.
Connie: Nice.
Jayneil: So, in terms of job stability, I know that I can update my portfolio, put in the new work and get a job but this is what I perceive, and I could be totally wrong, is if I become a design manager, I’m doing a lot more of the people management and I may not be spending that much time in Figma or any of the tools for that matter.
Connie: Oh yeah.
Jayneil: So, suddenly the fear comes in is like if I go into an interview, what will I show because the past two years I was just managing teams and really creating these work structures, not really doing that was designed where I can say that “Oh, this is the design reasoning behind it.” So, is that even a thing or maybe you were asked different things in the interview that maybe an IC is asked, let’s say.
Connie: I mean, managers are definitely asked different questions than ICs are asked. They also ask a lot of the same questions like in our manager interviews, there's things that we expect both managers and design ICs to do some problem-solving thinking through user journeys and flows, being able to critique products, apps. All those we expect everybody to be able to do but the managers will have additional conversations about how they build teams or how they think about like leadership … I mean, that kind of stuff. Managers also still give presentations on work and, of course, we have different expectations on those presentations like we know when we're interviewing a manager that they did not do the design work or most likely did not do the design work themselves, right? We know that because they're like “I led the team that worked on this project and here's what we did. And this is like … and I had two designers and a researcher and we worked on this or we started with this user statement or problem and then we went through this process. And one of the things …” so, they still show work, right? And we're not like “Oh, you didn't design that because we're not looking for the skill of did they design that. We're looking for can they lead a team to design a good product in the end”, right? So, we look for them to describe the story, the process like “We had this challenge because there's a different expectation from the engineering team and this” or “the timeline,” whatever it is. “And I helped it by doing XYZ, bringing …” we hear about the leadership parts like we want to hear about the actual management parts too. So, there's no … if you're looking for another management job after that, we know you didn't do design work, we know you're not designing as your day-to-day job. So, we look for different skills.
Jayneil: Oh my god! This is the best design therapy I’ve had in a while, being able to candidly talk to you and get all this … answering these questions I had in my head.
Connie: I love the way you're describing. You're like “I have another problem, Connie. I have another situation I’m afraid of.” I was like “This is all? Yeah, tell me about it.”
Jayneil: No, it is so awesome because I don't directly report to you, so there's none of this awkwardness. I mean, I can just be super candid with you. I can just say it as I feel it.
Connie: I hope that people should feel that way with their managers, right? I at least hope that you can have that level of candidness because your manager is there to support you. That's their job. And if you're not able to tell them your problems, then they're not able to help you. So, that's the type of relationship that I always aim to be. I always aim to build that foundation of trust so they can tell me even when they're struggling, they can tell me even when they're like “I don't know if this is for me. I don't know if I like this. I don’t I like this. I don’t like that. I don't this like.” All of that is super important.
Jayneil: There's always this thing where the person who cuts the check … well, not cuts the check but … is your manager and there's … I mean, at some level … I mean, I’m pretty candid with most people that I directly report to but yeah, I feel like with you, because you're not emotionally invested in this situation … I don't know … it's something about it like … I found that whenever I’ve gotten feedback from people that don't work in the same company as me, I feel like their feedback is just much more on point and candid because …
Connie: Interesting.
Jayneil: … they can see it in a very different way that the person who's working with me in some capacity cannot because they're kind of also involved in the situation.
Connie: Totally, yeah. That's why people have mentor relationships outside of work, right? Some people have mentors that are just … or maybe even they're in another field, not in your industry. That's helpful too. That's why people have executive coaches so you can have somebody else to talk to who is not involved to be able to talk about that. All that is super valuable. I get it. So, the more perspectives you have, that's great. That's just more options, more ways to think about it, more perspectives, I think all of that is … it's good.
Jayneil: I just put it there because I know my previous and current managers think that “Oh my god! Jayneil did not trust us.” I’m like “No, no, it's not that. I don't want you to think that.”
Connie: That's funny. Sorry. Yeah, I wasn't trying to imply that but just in general, I’m just like the more you can trust your managers, that's important. Even if you … and especially if you need to give feedback to your manager, if you feel your manager is doing something that isn't helpful to you, you just tell them. And I understand that's a hard conversation to have but it is an important one. Otherwise, that's not going to change, right? You're just like … maybe this manager is giving like … I don't know … too much feedback, they're being too hands-on and changing things and that's disruptive to the work” or maybe they're not giving enough feedback and you need more specific feedback on that. And I just encourage people to ask for those things very directly. Don't sit and then feel … then stew on it. That's just going to make you feel resentful. It's going to make you feel unhappy. Just ask your manager “Hey, can I have more feedback on this? It would be helpful because XYZ” or like “Hey, the feedback here has been good but actually I think we really need to just get to a decision to ship this quickly so I can work on XYZ other priority. So, why don't we just do this as is.” And it's fine to have those types of conversations with your manager be able to talk on the same level. And those are good discussions to have because your manager may not know “Oh, actually, this … you're right. This is totally not as important as this other thing. So, it's fine and then let's move on to the next one.” Those are great conversations to have and you should aim to have those with your manager.
Jayneil: 100%. Love it. For designers that listen to this that may be are individual contributors and are in the same predicament whether to move into management or not, how can they find your contact here or shoot you a message?
Connie: Well, I am available on Twitter. I suppose that's my most public way of being contacted. Also, on LinkedIn. Yeah, I’d say those are my professional forms of communication that works for people.
Jayneil: Perfect.
Connie: Do I need to say the handles?
Jayneil: No, no, I’ll put them in show notes but thank you so much for coming on the show. This therapy has been a blast and I loved it.
Connie: This has been awesome. I love sharing these little tidbits. If there's things I can share that help other people, great. That makes me super happy. So, thanks for asking all of these challenging questions for your own situation and thanks for giving us a chance to talk about these subjects that aren't usually highlighted, right? Not everybody talks about what it's actually like to be a manager or like the day to day of what that is, which is again super different from what it is to be just doing design work all day and every day.
Jayneil: Absolutely.
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