My guest today is Lily Konings who is a Product Design Manager at Instagram with previous roles at Messenger, AngelList, and IBM Watson. Interview Video: https://youtu.be/6TYK2Qk6sqw In this episode, we discuss the following: - Lily Konings Bio - How does a designer get promoted? - Introvert designer's guide to building personal brand - How to connect with folks outside your team as designer? - How often should you update your design mentor? - Why you should ask for a design promotion? - Why your environment affects your promotion chances? - Biggest misconception designers have about getting promoted - How to figure out the right environment for promotion? - Questions every designer should ask a hiring manager - As a designer should you prioritize product or people during job search? - Creating a 'How to Work With Me' Guide - How to deal with imposter syndrome after getting promoted? - How can a Design Manager encourage direct reports to give candid feedback? - Importance of setting expectations - Does large social media presence help in hiring design talent? - How to get in touch with Lily Konings? For show notes, guest bio, and more, please visit: www.designmba.show
Lily Konings is a Product Design Manager at Instagram with previous roles at Messenger, AngelList, and IBM Watson. She is also an avid startup advisor, helping founders build 0→1 products and scale their design team. Lily is passionate about helping people advance their career, most notably by writing her advice column newsletter called Welcome Designer and founding Lift Her Wealth, a not-for-profit conference teaching financial literacy to more than 4000 women. Currently, Lily lives in Oakland, CA with her partner and some plant babies.
INTERVIEW VIDEO:
https://youtu.be/6TYK2Qk6sqw
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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 Lily Konings. Lily is a product design manager at Instagram with previous roles at Messenger, Angel List, and IBM Watson. She is also an avid startup advisor helping founders build 0-1 products and scale their design team. Lily is passionate about helping people advance their career most notably by writing her advice column newsletter called Welcome Designer and founding Lift Her Wealth, a not-for-profit conference teaching financial literacy to more than 4000 women. Currently, Lily lives in Oakland, California, with her partner and some plant babies.
Lily, welcome to the show. It's an honor.
Lily Konings: Thanks so much for having me. It's an awesome honor to be here.
Jayneil Dalal: So, for all of you watching this episode or listening in, something I want to tell you is all the guests that come on the show, most of them, I have a prep call. So, we actually have a call where I talk to the guest. I talked with Lily and we just kind of talked about what we're going to talk about here. So, the magic that happens now, there's some prep work that's involved. So, Lily, in the prep call that we had, you mentioned riding a motorcycle. So, were you riding it yourself or what was going on?
Lily: No, I was not riding it myself. I think the context for why it was even a conversation between us was because over the long weekend that just passed, my husband and I went on a trip together. He rides the motorcycle, not me. And he
Jayneil: What motorcycle? A Harley?
Lily: it's a Royal Enfield.
Jayneil Dalal: Oh my God! This is very popular one in India, let me tell you that.
Lily: Incredibly popular. I mean, you can do an entire hour-long conversation with him on it alone but he actually has a pretty good presence in India because of the bike he rides.
Jayneil: No way!
Lily: Yeah, yeah, totally. So, the story is I was on the back of the bike for three to four hours straight. And you can't multitask on a bike. So, all you can do is just pop on music or a podcast and I think I binged like five of your episodes in a row.
Jayneil: Oh my God! That just made my day. Just hearing that just completely made my day.
Lily: Yeah.
Jayneil: So, I got a question for you.
Lily: Yeah.
Jayneil: I want to get promoted as a designer. Is it as simple as me storming into your office and saying “Lily, I want to get promoted? How do I get promoted? Today, tomorrow.” How does that work? How does a designer get promoted?
Lily: Well, the short answer, first of all, is definitely storming into an office does not work. That is definitely not the way to go. That's almost a guaranteed no. So, for a little bit of context, I think I can provide clarity or advice into the promotion scheme for three stages of a designer’s career life cycle. I can provide context into the first stage of breaking into design for the first time, second stage of up-leveling as a mid-to-senior IC, and then the final stage of deciding whether to continue down the IC as a senior IC or go down the management path and transition. So, there's those big chunks of your career at each one of those journeys. And, obviously, the promotion at that granularity can differ but what I have found is when you want to get promoted, in general, doesn't matter seeing your seniority, I’ve definitely found a set of themes that are observed from people who generally get those promotions. And so, I would say, the very first thing that maybe not a lot of people recognize or know is that you have to have a pretty strong personal brand or presence of a company that you want to get promoted at. And what I mean by that is when your name comes up, people should know who you are, what you work on and what you're really good at. That last piece is especially important because what you want to do is be someone that people look up to and you want to be pretty obvious about what you're good at so that people know what to come to you for. So, for example, if you're …
Jayneil: I just wanted to really interrupt you because this is so powerful because people, when they think about personal brand, they just think about Twitter following or social media presence but when you talk about internal brand, and you said what you're good at when your name comes up, but a lot of people, they work on projects, they do a good job but they're not necessarily the people that kind of network with everyone in the company. So, what do you mean by … does it mean proactively meeting people in the company or just letting the work speak for itself?
Lily: Yeah, that's a really good question. It's a little bit of both. So, the first part you mentioned about like networking, I think, can be interpreted in the wrong way sometimes because when you say networking … first of all, networking is a really gross word. Nobody likes networking. I hate networking. I would never say that the things I do are networking but it's more about making and building relationships. And I think that can be done whether you're introverted or extroverted. I know there's a lot of debate about whether you can succeed easier as an extrovert. I can talk about that for days because I am an introvert myself. And so, that can be challenging …
Jayneil: No way!
Lily: … in and of itself. Yeah, I’m extraordinarily introverted.
Jayneil: So, I’m kind of curious, what is your take to building connections or meeting people in the company because you said you're introverted … you're not necessarily excited to just attending all happy hours, all events that happen in a company. So, how do you approach that, building your personal brand?
Lily: Yeah, totally. So, if you're introverted like me, I tend to lean more on one-on-ones like building connections through direct conversations that don't involve five other people. I think that's where I get really stressed out. So, I think you can definitely do that, right? You should meet regularly with not only your manager but your peers, your skip, all their leadership in the company, even outside the company or continue to build relationships and even collect points of view that differ from yours to kind of make yourself just a better leader. And I think all of that goes into building your brand. Building your brand doesn't mean you're here to sell a product. It can also mean that you're here to sell yourself and I think that's important whether you're trying to get promoted or trying to write a book. I think all of it is important.
Jayneil: But what would you say like … one of the things I’m thinking about is if I wanted to just connect with someone not on my team, I could be nervous what I’m going to say to them, why would they grab coffee with me or skip or anyone like that doesn't work with me on a day-to-day basis. What would the topic be? How would you approach that? Would you use some kind of messaging like “Hey, I’m just looking to chat with you? Just want to pick your brain or something.” How does that work?
Lily: Yeah. I mean, obviously, you want to be respectful of other people's time. You should not be reaching out doing cold reach-outs with literally nothing that is beneficial for them on the other side. So, certainly, the easiest reach-outs are the ones where you have some sort of warm connection. So, that's either through like a company that you both used to work at, someone that you both know, a school that you both went to. That's definitely the easiest route but beyond that explicit connection piece, if you can figure out something that is valuable to them, it certainly would be helpful but sometimes not everyone asks for something back. And that's just on their own prerogative to be generous. And I’ve actually found that quite a lot of generous people are out there who are willing to get their time. You can just find them and kind of respectfully reach out, just be like “Hey, I have something very specific in mind that I’d advice for.” So, you don't have to beat around the bush too much. And “would you be able to spare 15 minutes of your time to help me through it?” And generally … this is from my own perspective, but as a mentor myself, generally I am very down for stuff like that but I will say I am even lower down if I can actually be like a long-term mentor in your journey and not just use me for like a 15-minute convo and then never I hear back from you. Those tend to feel a little bit too impersonal and I don't to do those as much. So, I like building kind of like longer term mentorship which, if you can find one of those for yourself, is incredibly rewarding.
Jayneil: But how often would you expect updates from a long-term mentorship? Is it every three four months when there's an update or just “Hey, I don't have any update to leave? I just wanted to say hi and this is what's going on.”
Lily: I mean that's certainly down to the mentee. At the end of the day, a mentor-mentee relationship should be driven by the latter. They should be the one setting the cadence and the agenda and stuff like that. The mentor’s side of the responsibility is being available as much as possible and being responsive and giving their time. So, for stuff like “How often should I hit you up? What should we talk about?”, that's 100% on the mentee’s part. If you feel like you have nothing to report on, it does not bother me at all for you to cancel our one-on-one but it's just whether you need it, right? If you're saying you don't need it, then it doesn't take off anything from my side.
Jayneil: I’m still mind blown away with this just opening statement you made like building the personal brand inside the company because the traditional view is like “Hey, I’m good at this tool. I’m good at this thing. I should normally be a candidate.” So, assume that someone who wants to get promoted has done a good job of building their personal brand in the company where their name comes up, it rings a bell who they are, so then my next question is does that mean that the leadership automatically comes to you given that you have a personal brand in the company that “Hey, would you want to be considered a promotion?” or do you have to voice those desires to the people in charge that “Hey, I think at some point I want to go in the next role” or something like that?
Lily: That's a good question. I will say, in a minority of cases, yes, leadership comes up to you and goes like “Hey, we have an opportunity for you. We think you'd be a great fit. I know you didn't ask for it but would you be interested?” I think that does happen. I shouldn't say it never does but I would consider that definitely to be in the minority case. I think far majority case, especially for women, people of color, is that they have to ask for it and be very proactive about it. And I found that you leaving it to chance, leaving it to the leader to recognize your ability and to present you the opportunity is not an impossible scenario but it's also improbable. And so, for anyone regardless who they are, where they are, I always recommend be proactive, build those relationships with leadership, be very proactive and tell them what your goals are. And it's okay actually if you communicate those goals well in advance of you actually earning them. I think that's actually the sequence that we should be doing things. We shouldn't be communicating our goals only when we actually have proven that we can do and accomplish those things. We should be communicating them so far in advance that the conversation that you then have is “What do I need to do to close those gaps to actually achieve it?” You don't want to be … you don't want to have to sprint 10 miles in the wrong direction and realize you have to reorient yourself. You should be saying “Hey, my goal is to be promoted. My goal is to be a manager. What should I do? What are the things that I need to do to achieve that?” And that's when you start making progress.
Jayneil: But then how can it be proactive without not coming across as like, I think, not needy but just … what do you call it? I think I don't know the right word for it but I just don't want to be “Oh, he's always asking me about like what is going to happen” or like … how does someone strike that balance?
Lily: I mean I don't view that as needy. It's definitely your manager's responsibility to be a supporter and a mentor for you in your career. So, at no point do I ever think that that kind of conversation or that type of ask is needy. If anything, I actually think higher of you to want to own your career and to be at the forefront of it. Some of my best … there were reports happen to people like that, constantly following up and be like “How am I doing against this goal that we chatted about last week? Do you have any feedback for me?” That's actually excellent. I actually encourage it.
Jayneil: Wow! this is very shocking because the default thinking would be “Oh, I don't want to ask too many times. I just asked one time and they should remember” but, of course, there's other priorities in the manager’s plate and they may forget.
Lily: Yeah, yeah, of course. I mean, obviously, the way that you word it matters, right? You're not exactly going up to every single one-on-one being like “Hey, am I getting promoted yet?” or like “Hey, when is this going to happen? I thought it was going to happen.” That's not the conversation here but usually what happens is “Hey, we aligned on these goals at the beginning half. How am I doing? What percentage of the way am I there? Are we aligned on the timeline that's realistic for me, etc.?” I mean, that type of conversation I’m willing to have all day every day.
Jayneil: Wow! So, framing it about the goals rather than just like “When is it going to happen?” Something I noticed in my conversation with you which you described to me is that a lot of your career success, if I’m not mistaken, is being finding the right environment to be in. I’m just paraphrasing the words you said to me. So, can you unpack that for me like what does that mean finding the right environment?
Lily: Totally. Okay. So, I can interpret environment in a million different ways. Some people interpret environment to being agency versus in-house, startup versus big-tech, enterprise versus consumer. Those are very valid questions and I can definitely answer those. I actually have had experience in every single one of those. So, I can talk about that but I think if you're talking specifically about getting promoted and what is the best environment for getting promoted, I would say, for me personally, it's always been the type of environment that recognizes my style of leadership. And what I mean by that is it can be really difficult to climb the ladder at any company when you don't have a clear idea of what you bring to the table. And the moment that you are clear to that, for some people, that may not be valued at that company and that sucks. That's a really sucky thing to have to come across to realize that “Hey, I …” Yeah.
Jayneil: I mean, I’m starting to think of an example, like meaning, for example, if someone's an introvert but then the whole company is filled with extroverts, so it means, would be that be a good example of what they're bringing is maybe not exactly in line because everyone's just a little bit different in the company?
Lily: Yeah, totally. I mean, I’ve actually been in that situation. I was actually in a company full of extroverts, especially … I mean, I shouldn't say extroverts but actually the company motto was “We hire founder-minded people.” And so, that usually tends to have a correlation with people who are extroverted because founders tend to be very vocal, very energetic and charismatic. So, I was definitely an odd duck in that kind of environment and it was really difficult to get recognized as a leader that isn't loud, that isn't vocal. And that tends to …
Jayneil: Then what about the work …
Lily: … people from behind.
Jayneil: Like the work would be outstanding. So, wouldn't that speak for itself?
Lily: No, no, always. I mean, I think this is one of the biggest myths about getting promoted. Everyone thinks that if you put your head down and just do the work, you’ll get promoted.
Jayneil: Yeah, just do the work.
Lily: No, absolutely not. I think that's something that I very passionately want to debunk because that's unfortunately not the way it works. I think if we judge everything by just the work itself, I think actually we might see a little bit more of an equitable environment and how people get promoted and how they get mapped up to higher levels but unfortunately, that's not the way it is. Work is work but it is still made up of people and people have biases and people have people that they want to work with over others. And it's also really hard to gauge objectively the work of one person versus another when it's in completely different scope, different areas, different Industries …
Jayneil: Projects, yeah.
Lily: Yeah. And so, you can't realistically all agree on this person's work being better than another person's but what you can do is have a sponsor in the room who say “I personally witness for this person's work. I’ve seen this person collaborate with others. I personally sponsor this person to be put up for promotion.” And so, it's that moment of having someone in the room that is on your side that is ultimately going to be the reason why you get promoted. I’m not saying that you have to have that at every single time you get promoted but it helps dramatically. If you only depend on your worth, you have to basically rely on the chance that someone is your sponsor in a more indirect way because they saw your work and they believe in it but you didn't really explicitly make that connection. And so, that really leaves it up to a lot of other potential failure points.
Jayneil: So, let's say that I know somewhat about my working style, I know how I operate as a designer, I know what my tendencies are, I know how I communicate with stakeholders, I know my leadership style. So, now, from this point on, I am now on this quest like “Let me find the environment that's right, at least suited for my promotion or for me to advance in my career.” How can I even figure that out like whether this new company, this new environment would be suited for me?
Lily: So, a lot of different things, a lot of different factors. Obviously, one thing that stands out the most is just high self-awareness like you have to be very clear to yourself what works and does not work for yourself. I know, for example, that I am not going to go back to a startup full-time for a while because at the moment, what I need the most is kind of a bigger company with a little bit more structure, I want the experience of scaling a team to that amount. And so, I know personally that that's not right for me right now. It's definitely right for someone else. So, I think that level of self-awareness is incredibly important to say “Yes, I know it's opportunities.” And then the other piece is you have to basically be open to the idea that the interview process is for both sides. I think a lot of people go into interviews thinking like “I’m being tested here. I’m the one on the chopping block. I have to basically prove myself” but I think the more senior you get and the more maybe comfortable you get, then the more you see this interview process is absolutely two-sided and maybe you haven't taken advantage of it in the past because I haven't. I’ve treated interview processes exact same way where I just like answered questions and shut up and nothing else but if you lean Into the opportunity to ask questions and to even probe a little bit deeper than what they're giving you, then you'll find pretty often that you'll be able to uncover some truths about the culture and the people and the product and the vision and all of that in a way that maybe answers some of your criteria for whether this is a good place for you.
Jayneil: I have a younger brother. And when he went on the interview process, I kind of told him like “Hey, you know what? This is a two-way street and, you know, you should ask him some questions too.” He was, and I don't blame him, but he was like “No, I cannot ask that” and I’m like “Why?” He's like “No. What if they take back the job offer?” I’m like “What are you talking about?” So, there's all these misconceptions and fear like if I ask a hiring manager a lot of these questions” like you're saying to figure out if it's the right environment, the fear that my brother had and maybe a lot of people have is “Oh, what if they think I’m like not fitting in or asking too many questions or just not going with the flow?”
Lily: I can reframe that for you. I reframed it for myself and it's worked ever since. Let's reframe it this way, right? You're scared about them pulling the job offer. Let's think about whether you actually want to work at a place that does that. Do you actually want to work somewhere that will penalize you for asking questions? Is that a place that you'll thrive at? And for most people, the answer is no.
Jayneil: I agree.
Lily: Yeah.
Jayneil: And now I’m kind of curious. Do you have a set of questions or what things you wish or now that you recommend people ask their future managers “Hey, these are the things that I learned that,” like you said, you didn't ask in your earlier part of the career? So, what are some questions that come to mind for you that you wish that you had asked?
Lily: Yeah. I tweeted about this a while ago.
Jayneil: I know.
Lily: I have like a list of questions that I really thought were valuable to ask. I’m trying my best to recall, right? So, I remember asking things like probing at different levels. Probing at the manager level, right? So, the person who will actually be supporting you as a manager, probe their management style, their track record for promoting people, how they handle feedback, how they deliver feedback and maybe how they also manage underperformers because you never want to be in a situation where the moment that you underperform, they basically start managing well, right? So, you want to make sure that the support system there is solid no matter what. It's almost testing whether …
Jayneil: But aren't they always going to just give good answers? For example, if I ask someone like “How is your management style?”, nobody's going to say “I micromanage” but then, like you said, if sometimes someone's underperforming, if I’m underperforming, even though they said they weren't micromanage, they're still going to do it. So, it's like how do I know that what they're saying and just taking at face value?
Lily: Yeah, totally. I mean, the same for a candidate coming to interview for a company. No candidate's going to say I’m really bad at visual design but you can tell. You can tell based on their anecdotes, their password, their portfolio. There are signals that kind of fill in the gaps. So, yeah, of course, no one's going to admit to enormous character flaws but you can kind of tell the things that they're not talking about or maybe even if you ask something as specific us “Hey, do you have a story about someone on your team that you supported who struggled to meet expectations? What did you do? What were the steps that you took to help them get back on track?” Pretty difficult to get away from that question with anything that is too lofty, too overly positive because I think that's a very tactical and day-to-day based question that will reveal quite a lot.
Jayneil: Wow! And I’m just narrowing the lens in that question I asked which is very broad focused like what questions to ask future managers. There are so many questions but in the lens of the theme that we've been talking about so far about how to get promoted, what are you looking for when you ask that question like “Hey, give me an example of someone who you recently promoted,” what insights are trying to glean from that answer that they give?
Lily: Well, I’m trying to glean, first of all, that they've done it like exactly have done it, right? It’s like if you asked an IC “Have you shipped a product before?”, right? Obviously, every single designer has had experience turning out mocks and working with … hopefully but I think the people who actually have experience shipping and getting out the door saying something else. And so, it's exactly the same thing for a manager. “Do you have actual success of bringing someone across the finish line to achieve that goal, right? It's not just all talk but you actually have something to back it up.” So, I think just the binary flag of having checked that box matters. Outside of that, you also want to try to glean how they did it, right? Is it through micromanagement, like you said, or is it through more hopefully supportive avenues that translate to something that is of an environment that's comfortable for you to grow in, right? Some managers will say “I was very closely monitoring their performance. I gave feedback in a timely manner, addressed gaps in X, Y, and Z ways.” And those are usually the scenarios I try to map up in my head when it comes crunch time to make the call to be like “Is that the person I want supporting me and is that the scenario I want to put myself in?” And so, it does help actually. I would say it's a pretty good question.
Jayneil: Wow! So, it's like sometimes when we go on job hunt or just career searches, and this is including me, a lot of times you're just so hoping to get to the finish line of just landing the job that these kind of questions are like … these we want to ask but we never prioritize that but I your approach where like “Hey, I’m spending significant part of my life doing this. Let me make sure the alignment is there up front.”
Lily: Totally, yeah. I mean it definitely matters. Obviously, not everyone's lucky enough to be in a job they love but as much as we can maximize that chance, the better.
Jayneil: But don't you get disappointed if sometime let's say there's this amazing opportunity and the product is so awesome to work at but then you have all these criteria that you want to make sure that match to make sure that you also advance your career and then let's say that's not there but the product is really insane?
Lily: Yeah. I mean, that's about personal preference at that point. Do you prioritize a product that you love over a good team of people? If so, that is 100% respectable and you can absolutely make that call, right? You might not care about being buddy buddies with your team and that's totally okay but for me, I actually prioritize people over products. At the end of the day what keeps me out of job is knowing that there are good people around me, both next to me, above and under me like that's extraordinarily important more than anything else.
Jayneil: It's kind of hard to kind of figure that out. I mean, does it involve background checks or having just good word on the street? Because I mean, in the interview, I mean, everyone's on their best poker face, just everyone's just nice and they're trying to woo you to join the company and the team.
Lily: Yeah, totally. I mean, I used to work in the recruitment space. So, I’ve literally done an entire project on how to get passive candidates to leave their jobs. So, you're lighting a lot of old memories here but I would say yes. The hardest and best designers unfortunately are not interested in leaving the jobs. And so, if they don't have the push factor which is the reasons why they want to leave their job, then you have to give them a good pull factor which is a good reason to join your specific company. And so, that is really, really difficult to do unfortunately. It's probably one of the hardest parts of hiring is to get a really good passive candidate. So, I think my answer for your question is not a great one. It all just depends on what you're willing to reveal, what type of relationship you have with that candidate. This is also a reason why referrals work so well, especially for senior positions. At the end of the day, if a really good buddy of mine refer me to a company that seems really, really optimal for my career goals from where I want to be and it's someone that I trust who refer them and they have really close and direct experience working with that team, then I trust it more and then I’m able to give them a little bit more of my time and listen to the opportunity before maybe I make my decision.
Jayneil: Love that.
Lily: Yeah.
Jayneil: I am blown away by the fact that after you got promoted, you released publicly just like leadership style guide. I’m just going to call it that. I mean, different people call it working style. I’m just going with leadership style guide which is, to me, a document that describes how Lily works. And in that document, you kind of also talked about some of your weaknesses or shortcomings, if I might use that word. It was not just all rosy pictures. So, I was like how did you get the courage to just openly share that because in many companies I’ve worked at, nobody even … you got to figure it out basically after a conversation, asking around, you kind of figure that out.
Lily: I mean, I feel it's one of two things. Well, first of all, for context, the ‘How To Work With Me’ guide, I was honestly just as surprised as anybody that it took off the way it did. I actually have seen this practice done many times before. So, I did not invent it. There's definitely someone out there who did it first and it's actually a pretty prevalent practice done by folks in leadership positions because at the end of the day, the more vulnerable you are and the more transparent you are as a leader, the better the team thrives. So, I think that's just general philosophy. As for being incredibly critical of myself in the doc itself, I think that it comes down to two things. Number one is what you spoke about earlier which is how do you find the right work environment to thrive in, how do you actually suss out the deep dark secrets in the closet that may hopefully … that may haunt you in the future but hopefully doesn't, right? So, I’m basically kind of trying to address that proactively. I’m trying to anticipate that question that folks who work or you know that will report to me in the future like … I want to answer that question before they jump on board because when they have jumped on board and they learn to find out that this is not suitable for them, it's going to be horrible.
Jayneil: Oh my god!
Lily: Yeah, it's not a great time for anybody like they want to leave, I have to convince them not to or find someone else or … obviously, I don't want to convince them from leaving if they do want to but there's a lot of minimizing damage involves and that's just horrible to do down the line. And so, I’d rather just be vulnerable and transparent up front to kind of mitigate that. The other piece I would say for the reason why I do it is also I’m lucky enough to be in a position where I am now a pretty well sought out candidate for most companies. And so, I don't have to work super, super hard anymore to kind of find new roles if I want to. And so, I’m saying that from the place of the utmost privilege. I did not have this so many times in my career. I definitely had to be the type of person to be like “I’ll take any opportunity I get and I’ll be grateful for it” but I’m lucky enough now that because I have so much option in front of me that I can actually be very selective. And so, as a result, it doesn't hurt me as much by being vulnerable and showing my weaknesses because you'll see it no matter what like once you hire me, you'll be able to see it but might as well say it now and trim down the funnel and the number of companies are interested in me now and just make it easier for everybody.
Jayneil: I’m trying to think about that moment where you're like “Okay, I’ve gotten the promotion,” you got the news, right? You got a champagne, maybe kudos like “Hey, you got promoted” but right there at that moment, everybody has some sort of this minor fear, apprehension and voice in their head like “Oh, I just want to make sure everything goes smoothly.” I’m kind of curious what where some fears if you can talk about that you were kind of wondering with this transition or change.
Lily: Yeah. I mean, everybody gets worried when they take on something new. I am not an exception by any means. I can also maybe put your question in more context because it's really relevant for me right now. I am at Instagram right now but I wasn't until just a month ago. I transitioned from Messenger into Instagram. And so, even though I didn't leave the company, it definitely feels a new company, new people, a new product, new practices, all of that. It actually completely feels a new company. And so, I am actually in that stage right now where I am a little bit anxious about whether I’m a good leader and I am suffering from imposter syndrome which is like the buzzword of the century. And I think it's completely normal to feel that. And I actually don't really like doing that thing where people just tell you “Oh, you'll get all over it.”
Jayneil: You'll figure it out.
Lily: Yeah, “you'll figure it out.” I feel like this is such a hot take but I actually hate saying that to people to just be like “Oh, believe in yourself. At the end of the day, just believe in yourself and everything will be okay.” I actually think that's extraordinarily unhelpful at least just for myself. And so, I try to actually reframe imposter syndrome in two ways. The first way is your personal feelings, right? My personal feelings of anxiety and discomfort, I recognize that as being extraordinarily normal and I also try to kind of recognize that as being prevalent especially at the beginning of every single challenge you take on. The reason why you took on the challenge is to grow and you cannot grow without being in out of your comfort zone. And so, by definition, you're going to be uncomfortable. And so, why would we be upset about that, right? You would never take on a challenge that you feel 100% ready to do and would not learn a thing from. So, it's totally fine. You time box the amount of time that you spend being in discomfort, uncomfortable, and just recognize that for what it is and just kind of move through that kind of phase. Now, the other part beyond those personal feelings of anxiety is also environmental. You and I literally have just talked about this at length but I think at the end of the day there are environmental factors into feelings of imposter syndrome. There is a wonderful HPR article about imposter syndrome and how it especially affects women. It talks about how white men typically get their imposter syndrome eroded away over time because they get validated, they get role models that look them. And so, imposter syndrome for them is actually almost always temporary. They will go through that dip like I mentioned at the beginning but then because of high environmental support, they kind of get over the hump and kind of move on with their lives. For women, it's almost the opposite like they get told that they're not good enough, they need to get better at certain things that their peers don't have to deal with as much. And so, it's a different set of standards. It's literally the definition of a double standard. And I just try to be kind to myself in that aspect when it comes to environmental expectations to not hold myself against the same bar that my white male colleagues might be held up against. And so, if I just kind of strive to seek environments that are openminded or the type of leadership that I bring to the table and also try to make the environment itself more inclusive as well once I get there for people coming in behind me, I think ultimately those fears about being a leader are going to be better for yourself and also better for everybody around you.
Jayneil: Oh my God! I love your answer and I just caught on to that thing that you said which was among so many amazing things you said, which is when someone was transitioning into this new phase as a leader, as a manager, getting promoted, there's that imposter syndrome and they're like “Oh okay, am I doing good enough? Am I a good leader?” And I have been on the receiving end of it where I’ve seen other colleagues and people get promoted and they'll ask questions like “Is everything okay? If you have any feedback for me, let me know” but my hot take is most of the times people don't end up giving them feedback because it's like … see, the thing is, as a manager to give feedback to an IC is well established. You have one-on-ones. You give feedback like “Hey, you should do facilitation more. You should do design work more” but the reverse way, it's kind of a little bit weird because in a way you're cutting my check. You see what I’m saying? So, it's very hard for me to be that up front that just lets you know you're doing this. So, how do you structure your one-on-ones or how do you approach that thing where your direct reports can surface things for you to improve?
Lily: Do you mean how do my direct reports give me feedback to improve as a manager or how do I deliver feedback to them to improve as an IC?
Jayneil: No, how do you set up a structure where they feel more empowered to give you feedback as a manager?
Lily: Well, I mean, there's so many ways that you basically want to aim to offset the power dynamic between the two of you because at the end of the day, from the first one-on-one you have with your direct report, there's just this implicit power dynamic where unfortunately there are things that the manager can do that will not always be optimal for the direct report. And so, you want to be cognizant of any moves that kind of shift that even further to the point where they don't feel comfortable even talking to you and being honest. You want to do everything in your power to reverse that. So, I mean …
Jayneil: Like what? What moves are you talking about? Is it like I’m just thinking right now?
Lily: Yeah, ‘How To Work With Me’ guide is one tiny early step towards it, being very vulnerable about what type of person I am and how to best work with me. The second piece is continuing to just focus on them as a person like the person that you're supporting is a human being with a family probably with their own personal lives and their own personal goals that are outside of their 9-to-5. And so, if you kind of recognize them as a human being, kind of support them from that angle, over time you kind of develop like … I don't know why they're calling it friendship is correct because you're not technically friends here but you are in support of each other, right? And good friends or good manager and direct reports support each other by doing things like being open and being transparent and being very generous with feedback. So, if you can build that foundation of trust, that is great amazing. As for tactical things, you can set up an anonymous feedback form that people can fill out at any time and completely is open at all times. It doesn't have to wait until PSE cycle time. You can also do check-ins with XFN to see what are things that you can do to better you as a person so that you know this feedback that you might get from your direct report isn't the first time you're hearing things. Ideally, you should always be seeking feedback as much as possible so no piece of feedback should ever come as a complete shock to you for the very first time, right? So, anything you can do to kind of minimize the surprise and the negative connotation of feedback and to make it more of a partnership, I think the better.
Jayneil: Also, when you're explaining all these things like being different, right? Whether it's being a minority or whatever that might be or having your own unique leadership style, we all have our own unique views, unique ways of working. For example, I don't drink. I don't drink alcohol, which I know … people are shocked when they hear that. They're like “Oh, you're an extrovert. You don't drink alcohol” but I just … I choose not to but then you see the narrative where all these, let's say, team outings have happy hours, have like brewery visits and stuff. So, if I was in a position of leadership, that would not be something that I would do naturally just because I don't drink. So, it's like that's not going to be my first thing that I do but then there's this pressure to fit into that narrative because you see all these photos on social media of all the leaders putting photos of their teams with beers and stuff. So, my question then comes to you is like how can one stay true to their values and stuff and not get sucked into this peer pressure like “Hey, this is the current trending leadership thing that you got to do. Everyone's doing it. So and so at this company's doing it. You got to do it too” kind of thing?
Lily: Yeah. Have you heard of the 80-20 rule by any chance?
Jayneil: The Pareto Principle?
Lily: Yeah, yeah.
Jayneil: Yes.
Lily: Yeah. So, I would say that … I refer to this rule a lot. Maybe I over apply it to a lot of different scenarios but I do think that it could be relevant in this question because what you ultimately want to do is spot the efforts that you are doing that actually convert into something meaningful and kind of get rid of everything else that don't. And everything else that don't are basically like … it could be happy hours, right? If ultimately what I would get out of a happy hour is closer relationship with my team, if I can get that through a more effective and meaningful avenue then going to happy hour, I won't go to the happy hour.
Jayneil: I see.
Lily: I think just finding ways that achieve the same outcome hopefully even more effectively and focusing on that and not these side quests, the better. So, I’m very unapologetic about not signing up for happy hours sometimes because, like I mentioned, I am introverted and I …
Jayneil: Thank god!
Lily: … a whole day of meeting, the last thing I want to do is making small talk over drinks, unfortunately. I will show up every now and then, of course, but generally I don't feel bad about that.
Jayneil: Wow! Because it's a big dilemma because you're like “Oh, you know, should I go to this happy hour because, you know, everyone's going to be there, I can bond with them, I can get all this feedback?” but then you're kind of exhausted. So, I guess you're like “Let me just find other ways to bond with them that don't require me going to that happy hour.”
Lily: Yeah. I mean, do right by yourself. Do the things that actually work for you like if happy hour is not it, find other avenues that are more sustainable for yourself because at the end of the day, you can force yourself to go to happy hours for maybe like three four years maximum and then by the fifth year, you're exhausted, you never want to see these people again. And then that's when you start suffering and you cause damage throughout the rest of the team because then all of a sudden, they're like “Oh, what happened to Lily? She used to show up every week happy hour and now she's nowhere to be found. And is she representing leadership here? What's going on?” And so, if it's not a sustainable approach, it's going to hurt somebody or actually even everybody down the line. So, it might as well be upfront and just be unapologetic about what works and kind of hone in on that.
Jayneil: I’m having one of those epiphany moments. I’m like … just this being, I don't know, unapologetic, I think that's the word I’m latching on to because then it's congruent behavior. For example, if I told you from the get-go that I don't drink, then whether year one or year five, I don't have to deal with that scenario of peer pressure because I told you from day one that “Hey, I don't drink” versus “Let me just force myself and let me just like, you know, first one or two years” and then suddenly you're like “What I’m doing with this?”
Lily: Yeah, yeah, totally. And actually, they're reminding me of a really wonderful quote. I don't know where it's from. It's probably from someone prolific but it was a wonderful quote that's like “Every disappointment is a result of poorly set expectations.” So, if your colleagues are disappointed by the fact that you're not coming out to drink, that's because you didn't set the expectation from day one that you don't drink but if you set that expectation up front, they would never be disappointed because that was always clear from the get-go. So, I think everything's about setting expectations and honing in on what expectations work for you and how it respects other people as well. You don't want to be a dick at the end of the day but if it doesn't hurt anyone and you can be true to yourself, why wouldn't you do that?
Jayneil: I think … the thing I’m thinking about right now is I have few friends that that are just very, one could say, blunt. When I say blunt, meaning they're very upfront like if they don't want to do something, they just say “No, I’m not going to do that. No, I don't eat this. No, I don't do that.” You're kind of shocked when you hear that because usually most of the times, people just go along with the flow even if they like it or not because we are social creatures, we want to conform to the norm like … Oh damn, I think I’m rapping but … so, I think that's the typical tendency. So, it's very rare that you come across people and I appreciate that in the long term because I’m like “Hey, you know what? Now, I know exactly what triggers you, what doesn't trigger you or what your preferences are” but there's a lot of other people they just kind of keep on going along with the flow. And somewhere down the road, you have to figure out “What just happened? They were kind of cool with it but suddenly they're not cool.”
Lily: Yeah, totally. I mean, this kind of all comes down to whether it's an environmental or personal imposter syndrome, right? At this point, I feel it's more environmental. Whether people expect you to present in an extroverted way, whether people expect you to drink, it can be applicable to both personal and work conversations but either in both those cases, if you set the right expectation from the get-go, then there's really no room for interpretation about how you work and how to best help you thrive. I think that if you find an environment that is open for you to just straight up say “Hey, I don't drink” and for them to be accepting of that, that is an awesome environment for you to maybe continue to see yourself being part of.
Jayneil: Thank you so much. I love that. I love that advice. I think one thing I’m curious about is you've got a pretty large social media following and one of the things that a lot of hiring managers face is hiring awesome talent. And I’m curious if having such a presence helps you in that or maybe it doesn't at all.
Lily: So, yes and no. It helps and it doesn’t help. And I’ll be very specific as to why. So, yes, of course it helps in sourcing essentially, filling the top of funnel of the recruiting pipeline. Enormously helpful in doing that. I’m exposed to way more people. I’m exposed to way more designers in different countries. I’m able to find myself looking at portfolio by some designer in Brazil or Prague or crazy variety that you get to take a look at but the no part of that answer is in terms of converting them to hire, I haven't noticed a tremendous amount of contribution as a result of a large social media following. At the end of the day, like we mentioned earlier, passive candidates are really hard to reach and they're typically some of the best candidates. And so, what you don't really find is that actually a lot of passive candidates aren't even on social media. And so, your presence makes no difference to them. They don't know who you are. They don't … they've never heard of you.
Jayneil: Oh my God!
Lily: And so, you're kind of starting from scratch with them anyways. So, I haven't found enormous amount of success on that end. Maybe for more junior candidates, it's a little bit better but for senior passive candidates, it makes no difference.
Jayneil: Wow! And I’m thinking if someone reads your blog post, you're like “Oh, I liked it” but they're passive. So, you still have to put in the work to meet to see if they're open to converting, give them that pull but worse is if someone applied through the traditional channels, well, at least you know their intent is clear that they do want to join your team or just join the company.
Lily: Yeah, I mean I’m talking about like these passive candidates had never seen my stuff. They don't know who I am. They don't go on Twitter. They don't read blog posts. They have a clear life outside of their 9-to-5 that does not involve being on design Twitter. And so, typically these folks, you have absolutely no leverage with them other than, like I mentioned, like referrals or good word of mouth but you're basically starting from scratch with these folks, social media following or not.
Jayneil: That's fair how can designers listening to this contact you? How can they get in touch with you?
Lily: Well, I just spent 10 minutes talking about Twitter. So, they’ll definitely find me on Twitter. I am on there a lot. What else? I am trying to get back into writing. So, hopefully, trying to revive my old newsletter. So, they can certainly read some of my older stuff on there but hopefully also see some new stuff come out. There’ll probably links in the description of this episode, right.
Jayneil: I want to say yes, absolutely. And I want to say you have to get the Midas touch when it comes to writing anything on Twitter. Every thread, everything you put just goes viral. Maybe with some people on the outside, I’m noticing, but you have an insanely high strike rate. It's just like insane boom, boom, hit, hit.
Lily: You know what's crazy? I have no idea why. I don't write things for the sake of virality. I don't expect things to go to be popular. If anything, I actually almost have the opposite intuition. I’ll be like “Oh, this one's going to be really good. People are going to really this.” And it's very few compared … relative to other tweets I made but then other stuff, I’m like “Oh, everybody knows this. This is super commonsense stuff.” And then thousands of people will like it and I’m like “Okay, I clearly have no idea what I’m doing.”
Jayneil: Lily, thank you so much for taking the time and coming on the show and sharing your wisdom.
Lily: No, thank you for having me. I really appreciate it.
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