The Secret to Being “Likable” at Work | Principal PM @ Microsoft, Ellie Rui
1h 10m 39s
Ellie Ray, a former principal product manager at Microsoft, shares her rare journey of being promoted every year of her career, attributing it to a transformative manager who acted as a "player-coach," providing timely, candid, and actionable feedback. This consistent support helped her develop core PM strengths like strategic framing, customer empathy, and cross-functional collaboration. She transitioned from hardware supply chain to a user-facing product role, where she pioneered early AI features and worked on a customer data platform. Despite her success, she recognized the risks of being typecast in enterprise PM work and actively pursued diverse customer portfolios to grow as a product leader. She observes that AI is rapidly changing product workflows—accelerating tasks like prototyping, research, and writing—but cannot replicate the human elements of relationship-building, context, and emotional intelligence. Ellie stresses that PMs with weak problem framing skills will be left behind, as AI can deliver faster, clearer solutions. Ultimately, her career underscores the importance of adaptability, a growth mindset, and the ability to embrace feedback as a tool for improvement. She believes the future of product management lies in balancing AI-powered efficiency with authentic human connection, customer insight, and leadership presence.
that you got promoted every single year of your career. How the heck did that happen? And how does it feel to be blessed? - Not only do you have to be incredibly hardworking, you also need to be recognized for your hard work. Not every team, unfortunately, does that. - If you had it bet your bonus on it, what PMs do you think are gonna get chopped? - Oh my gosh. - PM with weak top and framing skills are gonna get left behind. - You should recommend starters versus big corporate. - For new grads, yes. - Ooh. - The tech right now is very challenging. People are constantly getting laid off, companies are constantly trying to bring them at the way we do things. - I once got feedback on a Friday at 7 PM and I cried big text on them, like, sir, please get out. Like, why do you do this to me and ruin my life? (upbeat music) - Office drama. - Welcome to Office drama, where we talk with people obsessed with their work, learn about their biggest breakthroughs and reveal the drama within. Today in the office, we have someone who was promoted every single year of her career. Crazy. She's a proud UBC alum studying computer science and business. She's a previous principal PM at Microsoft and she has perhaps one of the strongest pulses in the senior IC world of product and I'm so excited to get caught up because I kind of out of the market for a couple of years. So welcome, Ellie Ray. Ellie Ray, I really want to get to know you more, but we have to talk about like, how are we connected? How do we meet? - Maybe here today. - Definitely, I believe your husband was roommates with my manager? - Yes, that is the connection. She used to work at TikTok with me and maybe you know what? I think he was Kevin's friend first. Yeah, Kevin's friend first, they became roommates and then I became honorary roommate, of course, and then we were able to take a talk together. So there are a couple of times that I put Victor's apartment in my vlog 'cause I've ever seen his apartment spend beautiful. - I have not, you know. - It's beautiful in San Francisco. - Oh my gosh, you love his place. And then I was like, Victor, would you ever be on my podcast office drama? And he was like, "Uh, uh, uh, uh." (laughing) I'm so boring, but you know what? I have a really great rapport. Her name is Ellie, you would love her. She's so, she's just doing the team. She's like a rock star. She's done so many things. Like she's shipping so many big things. I think she'd be great for your podcast. And I was like, "Yeah, sure, connect me." And that's how we got connected. - Well, I'm really flattered. Thank you, Victor. - Thank you, Victor. - Thank you, Victor. Well, I remember the day he told me he suddenly became the coolest manager in the world. - Really? - Yes. 'Cause he was like, "Well, I have a friend." - I have a friend. - Who does that? - She's like a PMing influencer. I was like, "Is it Chloe? She." He was like, "Yes." (laughing) I was like, "I'm being a fan. You are settling the coolest person in the world." - Oh, that's amazing. - I'm so glad to hear that. I'm glad we got connected. And, but where are you based right now? - I am based in Seattle. - Okay. So, why? (laughing) Was that Microsoft? - Yes. - It was Microsoft. A lot of people ask me that question, to be honest. Seattle's cool. I like the hikes. I think the summer months are very deceiving 'cause it's absolutely beautiful. - Yeah. - And then you forget the rest of the year for the eight months. They're raining every single day. - Yeah, yeah. - But I love Seattle. No taxes. That's great. - So you love Seattle with a straight face, say to the camera. - I love Seattle. (laughing) - I do not understand it quite yet, but I love the no taxes thing. I mean, this week in LA has been absolutely beautiful. - Yeah, what do you think? What do you think? - I love the LA. - LA. - In Seattle, all your career. - Yes. - And then before that was Canada. - Yeah, it was Canada. - And then before that was. - China. - My God. - What part of China? - I was born raised in Nanjing, which is a city next to Shanghai. I was told now it takes one hour to get from Shanghai to Nanjing, but when I was going up, it's four hours train. - That's forever. - Yes. - You have a lot of Canadian influence in you, but you've been in the States for so long as well. So do you feel more, do you identify more with being Chinese, being Canadian, being American? Like, are you Chinese, Canadian or Chinese? American, like, what are you? (laughing) - I don't feel particularly connected to one, because I feel like they're all different chapters of my life, if you will, 'cause I think at the roots, I'm Chinese. - Yeah. - I think born raised there, like a lot of my values were shaped by Chinese influence, like, the way I see family, humility, discipline, education, I think those are all things my Chinese roots have brought me, but then Canada was more, like, coming of age chapter for me, 'cause I think UBC, especially, it's such a diverse university. We actually had, I believe, 50% of the student body being international students, and it's not just culturally, also socioeconomically. So I feel like I was able to form friendships with people from different walks of life. Like, they have a different definition of success, different family upbringing, financial realities. I was able to connect with a lot of people, and I wasn't just constrained to forming relationships in a single social circle, where people who always think the same way. So I feel like that also made me a lot more observant and empathetic as a product manager. I feel like that translates to everything. - Empathy, the core scale of a product manager. - Customer empathy, yes. - Because I think it's essentially about translating all of these different people's motivations and desires into the products we built. - Yeah. - College. Did you have any internships? - I did. - What did you do? - I worked for, I think a AI startup in my life. - Already? - It was back in a day. Like, we were still writing like Python scripts. It was very different than what AI is today. - And so you're a senior, and then you apply to work at Microsoft. Like, how did that happen? What did your first Microsoft job happen? One does not simply get a job from Microsoft at a college. - I'm sorry to disappoint, but it's the most boring story ever. I applied. There was a campus recruiter that reached out to me, and then she called me. She's like, "Hey, would you like to schedule an interview?" - For the. - For the PM role. It's just a new grad product manager. - Okay. - Because I think when you grad, they had either product managers or software engineers, and you can choose either path. And for me, I always knew I wanted to be a PM, because I always knew I did not know what a PM was then. - Correct. - So how did you know? - Well, I think during my internships, I only did software engineering internships, and I was extremely challenging. I am not a good programmer. Like, I think sitting there just looking at the code all day, trying to figure it out, really stressed me out. But I was asking more questions around, why are we even doing this in the first place? Why are we even solving this problem? Who are we building this for? And then I think my dev manager at the time, he was like, "You should probably explore product management." And here I am. I think I just enjoy the problem solving aspect a lot more. But I think even in college, it's when product management started taking off and becoming a trendy job, if you will. So I knew like the nature of the job was to work with, you know, cross-functional people, and that's something I thought I would be interesting, even though I was an introvert, I am still am, but I think the job forced me to be very-- - What's your MBTI? - I am a Pisces, and I am INFJ. - Okay, you may proceed. - I think just the social aspect of the job is really appealing to me, and I remember when companies were doing campus recruiting, they would send like product managers or like engineering managers to do talks on campus, and I always have found the PMs to be so charismatic, and I wanted to be them one day. - Dang, you be seeing a good college. - Were your parents in Canada or-- - Yeah. - Okay. - And then do they tell you what they wanted you to do or they were like, "Go follow your dreams, Ellie." - Great question. My parents are the not stereotypical Chinese parents. They never really prescribed like what kind of career path I would choose what kind of school I would go to, or even like most Chinese parents would be like, "Oh, you need to get an A in school." They never cared. They only had two girls for me, which is be happy and be a good person. - Wait, what do they do? - They both had their own businesses. - Yeah, business owners. Yeah, I think in a way I was super lucky, but I will say, even though they had no rules for me, I still did all of those Olympic math tutoring, piano, ballet lessons. - Yeah, you play all that pressure on yourself? - Yes, yes. Because I think I'm very intrinsically competitive. - Are you only child? - I am the only child. Yes. - Oh, I see, I see. - When I was in second or third grade, all of my friends were going to those classes, so I went home and asked my parents, "Hey, why am I not in those classes? Do you not care?" - Do you not care about me? You're only child? - Yeah, and my mom was like, "Yeah, you can sign up for it, we'll pay for it, but you need to call and sign yourself up." So I remember calling the tutoring center when I was, I don't know, like eight or nine. - Whoa. - And I was like, "Hey, can I get a tutor for my math classes?" And the lady was like, "Can I talk to your mom? How old are you?" (laughing) - I'm 18. - So you were born with initiative? - I guess so. I think my mom also told me this, most recent time when she visited Seattle last month, but I have always been very opinionated. So she just kind of let me make my own decisions. - Yeah. - And I think later than when my family moved to Canada officially when I was in grade seven, we toured a bunch of schools. And then I told my mom, I would like to finish my education in China 'cause I don't feel like I'm ready, actually let me. - Oh, that's great. And then so when you told your parents, you're gonna become a product manager, what did they say? - It's funny, because no one in my family,
family is good at math. Noah in my family is in STEM. So when I told my mom that I was interviewing for Microsoft, she was like, "Oh my gosh, good luck. That sounds really, really challenging." But you'll do great. And now when I got the offer, I called her. She was like, "Oh my gosh, I didn't think you were going to get it. I was so stressed." Yeah, I don't think my parents had any expectations for me, which in certain ways I really appreciated. But yeah, it's a surprise for everyone. Okay. Amazing. And so then you joined Microsoft. Wait, no, you moved Seattle. I moved to Seattle. So your big first, big girl alone, being alone in Seattle. How was that? What was your first team? And then you spent the next six years there at Microsoft. No, actually, switch teams. Because when you, as a new grad getting to Microsoft, you don't get to choose what team you're on. I think they just kind of placed you based on your start date. And the first team, I learned a lot. It was hardware supply chain engineering. But then I remember seeing the email of my first manager sending it to me. And she was saying, "Oh, we're part of the hardware surface Xbox supply chain." Oh, and I was like, "Oh my gosh, that sounds really challenging." And I have no supply chain knowledge. Who does outside of college? Who does? Exactly. Exactly. So I spent a year on that team. I learned a ton of things. But I always knew I wanted to do something that's user-facing. I have a special eye for design. I would like to believe. So even when I was on that team, every single feature I was working on, I tried to do my own Figma prototype. Because we had no access to a product design resource. It was mostly internal facing. So you paid for your own Figma plan? Yes. I feel like you could have asked your manager to expense it. I feel like that could have happened. Really? Yeah. You can get special expenses for software. I'm not sure. I will ask. Next time. All right. So you paid out of pocket. I paid out of pocket. And I was doing these like very wacky mocks because I have no design experience. But I would still like to show people this is the vision. This is what I want to. Yeah. This is what I wanted to look like. So very early on, I knew I wanted to switch teams. But literally a few months after I started my job, COVID hit. So hiring free's across the entire company. All the roles were paused. It was a very difficult time to switch teams. But I'm shameless. I just look up people on teams that I think, you know, there were always interesting. I just messaged them. And I got a couple coffee chats. And I think finally a year later, I was able to switch teams to what I went into a team underneath the business application work. It's called dynamics for marketing. So at the time, the product was actually in private preview. And I was able to, you know, go in there as a junior product manager, and I stayed there for five years. You know, a couple of reworks. I got to work on a CDP, which stands for a customer data platform. And then I also experimented with a lot of AI features very early on. That's so early. Yes. Like probably I want to say late 2021, 2022. So I shipped a couple AI features. And then we started doing co-pilot experiences. I'm co-pilot for business, right? Yeah. For business. For 365 or? It was dynamics 365. What's the difference? So I think the 365 most people know are they're part of the office organization. Right. And then there's business applications. So think about Salesforce for Microsoft. Yeah. Yeah. Okay. Yeah. Yeah. Yeah. Got it. And then five years on that team, same manager or same manager. Yes. Cool. The craziest thing about your story is that you got promoted every single year of your career. Yeah. I think the keyword is blessed. I was thinking about this a lot because I think a great manager really makes a huge difference in your career. Okay. And I will say I got really, really lucky because not only do you have to be incredibly hardworking, which I think most people are. You also need to be recognized for your hard work. And not every team, unfortunately, does that. But I had that privilege. I had a manager who was a great player coach. He has incredible high standard. So certain times it felt really spicy to get that feedback, but he's extremely candid. I learned everything that I know on how to be a PM from that team. So I'm very grateful for all the expenses I've had. Did you know that he was a good manager right off the bat? I think through my interview process, I could tell he was extremely sharp. That's from his answers like from how he answered questions about the team and the vision and whatnot. Exactly. Yeah. How did you know that he would have your back? That's a great question. Because he could be smart and sharp, but you don't know if that person has your back. Yeah. I think while at least in the years that I reported to him, he was always proactively watching out for me and pushing me into the next level. I remember when I first joined his team, I was a PM one and he gave me, because when you're a junior PM, you'll give them very scoped problem to work through and execute. And I don't remember exactly what he gave me, but I remember having a one-on-one two-three months later. And he was like, "Hey, Ellie, I think you should be a senior." And let's work on that together. So he's very methodical about what are the skills I need to learn and grow and where does he see me in terms of career ladder, if you will. But he didn't care about years of experience. He recognized my talent and he invested in me. And I think even after that, he was always proactively pushing for me to get promoted and telling me these are the things I need to work on, these are the things I need to learn. So I'm really grateful for that. What would he say your talent was? I think strategic framing and also includes with authority, which I think it's very important for PMs and I think all in all storytelling. How do all of those manifest in like your day-to-day? Where does that show up? As a product manager, your day-to-day look very, very different, right? Oh, and also I think bias for action is extremely important. Yeah. I love to bring people together whenever I do problem discovery. I will set up a call with the customer, but I will bring my product designer, my engineer, my data scientist, all in those discovery sessions. Because I think I really care about hearing different perspectives based on the role and the displaying that you're in, you might hear something from the customer that I might miss. So I love doing discovery together. And after that, I would synthesize the customer notes and provide some sort of framing on these are the problems we need to solve. Do you agree or disagree? Because I think that's also part of being a lazy PM. When you bring people together, I don't have to play telephone anymore and tell you that, okay, this is the task and just go execute. Because nobody liked to be told what to do. Yeah. I think giving the team that context is very important. I also learned a ton of things from my previous team in terms of having an eye for user experience and have a good eye for design. So I would visualize those solutions together with my product designer. This is back in the day before AI. And then we would go back and do this iterative process. But essentially, this is the process of building the trust with the team that this is something we need to ship and do together. What do you think the biggest key difference? The growth area or impact area was for you to get from PM to senior and from senior to principal. As a product manager grows, the complexity of the problem you solve also grows and the ambiguity increases. So I think with the junior PM, you're usually given a very scoped problem and then you can execute really well and to end the product life cycle. But as a senior, you need to be completely independent. So sometimes identify new problems and problems that people didn't think of. And then you need to spot that, solve that, bring the team together. Yeah, like a manager is like, this is your domain. Correct. What's the problem? Yeah, you figured out what's the vision. What's the problem? Where are we going? Correct. Got it. Yeah. So it only took you one year to show that senior and principal. I think it's two and a half years, but averaging I was getting promoted every year. Yeah. Was there any point in time on this team? You were like, it's time for me to leave the team, leave the bird's nest. Or you're like, no, I'm here forever. I'm here for life. I'm definitely not a lifer. And to be honest, staying on Microsoft for six years was already longer than what I expected. There were times that I thought about leaving, but I felt like at the time every single conversation I had with my manager or from people in the organization, I was still learning. So I think that's the reason why I stayed. But then I also had the fear that I would start to get tight casted into a certain PM domain, if you will. And that turned out to be true. Like I think when I was interviewing for different roles, they were like, Oh, your experience is so enterprise. You're so beautiful. You've never done anything to see. Because my goal for myself is really, I'm a product leader. I want to have multiple set of portfolios. I want to have served multiple customer personas. And I think having that title was actually very difficult for me to do donning switch. Well, it's crazy. It's crazy how like your success boxed you in. Yeah. Absolutely. And then you're like, no, no, no, no, I can do more than that. Yeah. Like I can be adaptable. I can learn. I can do consumer. Exactly. Exactly. Q3 is here. And I feel like it is perhaps the busiest time of work for me because everyone is just trying to launch products right before the holidays. So I am in back-to-back meetings. And with my pregnancy brain and the summer heat, I sincerely cannot remember what people are saying. But I do use granola. The AI powered no-pad built for the way real people actually meet. And if you're not using it, I feel like you're not being efficient. And I don't know if that's a personal attack. I'm so. But I'm serious, granola securely transcribes your meetings, you can take your own notes if you want. But the beauty is you just focus on being present, asking important questions, and then after the meeting, granola spits out a clean, structured set of notes with takeaways and to-do's. And then I just copy/paste that into a follow-up email and bam! Something that used to take me 20 minutes now takes 10 seconds. And we don't always get those 20 minutes in the same day. So using tools like granola really changed my follow-up and follow-through game and people think I'm super organized because of it. If meetings are eating up your day, granola is a no-brainer. You can try it totally for free. Just head to granola.ai/office drama, that's granola.ai/office drama to get your time back. Try it for free at granola.ai/office drama. I'm actually horrible at small talk, Ellie, and I really want to learn more about your lore. So in personal shields, we go over your values, your top role models, your skills, your turning points, and where you see yourselves in five years. But the assignment is you actually have to draw it yourself. No words, no numbers. And this is Ellie's personal shield. So this is exactly why I did not become a product designer because I am terrible at drawing, even though I love art, but we will go over them. So the first one is values. I drew a little person with the flower on the head. Is it gross? It's gross mindset. I said, it's gross mindset, yes. It is my favorite value from Microsoft. I think it's just something that's instilling me so much. You remember me? Someone with out-of-growth mindset, and you're like, give me the ick. I'm so sorry. Yeah. Whenever, yeah. Whatever. Anyways. I love gross mindset. I think the other two would be botanous and empathy because I don't ever want to make a fear-driven decision. And I think my career reflects that. Your career reflects a fear-driven or anti-fear, okay? Anti-fear-driven decisions. Got it. In terms of role models, I have a TV character. I show that I really enjoy from Skando, so Olivia Pope from Skando. Just the archetype she represents, which is very fierce, calm under pressure. And she always brings creativity into her problem-solving, which I think is really, really cool. And then she's able to walk into a messy and high-stake situation and bring clarity to the room. And I think that's exactly what a product manager does. Bring clarity. Bring clarity to the problem. In terms of, I would say, a real-life role model. I want to give a shout out to one of my previous managers at Microsoft, Jim Nakishima, Hyjim. I learned all of my product management craft from you. Just overall, he also just modeled the kind of leader that I want to be one day. Not only was he a player coach at his core, he invested a lot of time into the team, really growing the people, honing the PM craft. He's also just a very well-rounded individual. I know he skis like 55 days a year, and it's too many days, and 50 to 100 miles of bike riding on the weekends, but still show up to work every single day with such energy and thoughtfulness into how he operates. So that's a real-life role model for me. So skills, I drew a little bit of a single person dancing. So I'm not sure if you have seen the YouTube video. Did you dance before? No, not that one. I don't know how to dance, but the skill I want to highlight here is influencing with authority. Have you seen how to rally a crowd? It's like this person who is in a park, and he starts dancing alone, and then the second person follows him. I see. Soon after a whole crowd starts dancing with him, there's a very interesting leadership lesson there. It's the second person that follows, actually rallies the crowd, because it takes a lot of gut and a lot of boatness to be the first person to start dancing. But then if you're just dancing alone, it looks weird. But if the second person starts following, and then people start looking over, so I think it's kind of like the influence that I have in the team as well. There were definitely periods of time where the vibes were down, we go through ups and downs, I think in any person's draw, but I think being the first person or the second person that helps lift your team up is extremely important. And I think that's one thing I bring to the table. Are you the first dancer or the second dancer? I think in terms of the role I have in the organization, I've always been the second, but I would like to be the first one day. One day. Silver one day. Yes. Turning points. I drew a little computer sign, because actually the fact that I ended up in this discipline is completely random. I was not a computer science major when I first started college. I was just in Bachelor of Commerce. I remember one day I was studying in the library and then some folks were talking about, "Oh my gosh, this class is so hard," and I asked them what major they were because they were in the same, you know, building as me. But turns out there was this major called Bucks, which stands for Business Combined Computer Science. And then they were talking about how challenging it was. So I decided I wanted to try myself. So I walked into the admin office on the first floor, and said, "Can I enroll in that program?" And here we are today. Wow. That's. So spontaneous. It was spontaneous. Permanent decision. Yes. But I really enjoyed it. I think it was very challenging because I was never really a STEM person before college, but I think it brought me to where I am today, which I'm very grateful for. Five years from now, I drew a little split screen because if I'm being completely transparent, I don't really know with all of the changes in the industry with AI, where exactly we're heading. But I do know what I love, which is building great products with great people. And I think all of the fundamental skills I've learned as a product manager, which is have the customer empathy, tell the story, execute with a great team. Those things are not going to go away. So ideally, I would love to keep doing what I'm doing. But if things go south, I would love to open a Korean med spa. Are you Korean? You're not? I'm not. We always, like, that's not where I thought this was going to go, but the med spa, you love the med spa. I love the med spa, yes. I want to talk a little more about Microsoft because I think you stayed because you kept learning, and that's probably because of your manager, right? Yes. And so, like, I wanted to hear more about what made your manager such a great manager to you. Why did you stay? How did you grow so fast, like that kind of manager match is so, so rare. I've had 11 or 12 managers in my career, and most of them sucked. Oh, my God. Yeah, they were like, I had pretty bad managers and I had lukewarm managers. And then I finally had great managers. And so I saw kind of the whole, the, the gamut, the gamut. And I was like, oh, I, I realize the majority case scenario is a bad manager. Actually, I'm curious to ask you because I think it's a very subjective topic. A great manager to one can be a horrible manager to another, or there are cases that this person is the horrible manager to everyone, right? Yeah. No, I got the horrible ones. Yeah. So what's your take on a great manager, actually? I think the first time I had a really good manager was actually just a nontoxic manager. And I was like, oh, I didn't know. They could be nice. Because I had pretty toxic managers, like, you know, they yell at you. They berate you. They bring you. They attack your character. You're like in stupid. Oh my gosh. Yeah. And I think it's, it was just part of it. Or I think my first managers and corporate were very, you have to wait your turn, everyone's smart here. Yeah. When you work at a big company like Google, every new grad just seems stuck up to you. If you're in the managerial level, like you're in your 30s or whatever, and then you see a 22 year old being like, I want to get promoted after like nine months, like, no, you're not. And then I think that the bad managers don't know how to build a plan and like set expectations. Right. And so when I had the first, yeah, you're not going to get promoted. I didn't want that conversation. I was like, if I go into asking for a promo and they say this, I'm quitting because there's never a chance to grow faster. It's always a waiting game. And I'm not going to play a waiting game. Yeah. Yeah. I'm not going to work hard for a waiting game. That's not what I'm here to do. Yeah. Yeah. So I think there's that. I also didn't learn from a lot of managers. And then I got toxic ones. So that was like cool. Then I got really incompetent ones who like didn't know how to like use an air table or something. And then they would tell us to onboard into a new tool and they wouldn't know how to use it. And then they'd be like, okay, now I transfer it to a Google spreadsheet and I'm like, why it's the same thing. I think they just have really dumb requests. It feels like managing that. My first good manager was at Meta and they're very people management oriented at the time. I don't know about now. I think they're probably more like execution based now. Yeah. They were really good. They had my back and they always wanted my growth. And they want to staff me onto projects that I really think they would match with my strengths. And then they would be super on top of meeting me. Oh, right. Another sign of a bad manager is they're always 17 minutes late to your 30 minute one on one. And I'm just like, um, okay. So definitely don't respect your time. I'm so sorry. Yeah. I've definitely gotten the like lots of calls and where are you at? How come you're not your seat? Oh my god. I was like, I'm on a one-on-one. I'm doing a coffee chat right now. Yeah. I think there's that too. I don't know. I feel I'm like going back into the past as well as so long ago and it's pre-covid, pre-covid years. It's also crazy that you had 11, 12 managers. Yeah. 12, yeah. It's crazy. Reworks. You know how they are. Yeah. But you see the different, you know, end up the spectrums. Um, yeah. I think that I did see a lot, which is why I think I got disillusioned over time. Like, I would not want to be a manager.
I was like before I really wanted to do it and then I'm like, "nah, this is not fun. What you're doing is not fun." That's totally fair. I was thinking about this the other day. If the first three managers of my career all sucked, I don't think I would be where I am today. It impacts you for the rest of your life. You really think about it. I'm like, "I don't want to be like you, Bolden like this." But what? I think I'm always so surprised when I meet people with freight managers, because these people are just so happy. I'm like, "I didn't know you'd be happy." That's crazy. That's so unfortunate. I'm so sorry. I will also say, I think everyone needs a different type of manager throughout the different stages of their career. I think a great manager to me, first of all, is going to provide a really great strategic framing on guidance to everything that we're doing, because I would like to understand the context and why. I don't want to be told just to execute on certain things. I think we also touched on that earlier as well. When they can't write a strategy doc and you read it, you're like, "This is so weak." Exactly. What do you mean by this? Exactly. This is so unattainable and weak. That's when I'm like, "Okay. You're just not. You just don't know what you're doing." Exactly. I think the second thing, which is really important, especially I think in big tech company is to provide air cover for your team. Basically, your manager unblock you. He help you align with other teams so that you are set up for success. I think that's extremely important. I think the third thing for me, which is really underrated, is I think a great manager actually manages up better than managing down, because if you think about it, it's easy to tell someone what to do, but if a manager can sunshine his team to the broader organization, this is the things that we are working on. This is the visibility and the impact that the team is driving. Really set you up in a great position. I think, lastly, the biggest point for me personally is that I really appreciate a coach. I really need someone who is really good in their PM craft, and that's investing my growth that can help me and teach me how to be a better PM. Those are different from a manager and a coach. Absolutely. How would you differentiate? I think when we think about a manager, it's just like, hey, these are the priorities of the week. What's the status update? Exactly. It's more execution driven. It's more execution driven, if you will. This person is just making sure that things are going through the motions. I think a coach is someone who is invested in your growth and make you better at your craft. I was lucky enough that both my manager and my skip manager at Microsoft, they were player coach at heart. I think I was able to hone a lot of my skills, storytelling, execution, framing the problem, coming up with a strategy, really well, all from that team. What did player coaching look like? What did your previous manager do? Great question. I would receive very timely, actionable and candid feedback. I remember there were times that I would run a meeting for cross-functional teams and I would show some slides. I would go through my spiel and then after the meeting, he would be like, "Hey, Ellie, that was good." But. Hey, Ellie, can we talk? Yeah, can we talk? Can we talk? Here's some feedback. Exactly. Exactly. Exactly. It's very useful. He's like, "Well, you need to drive the meeting. I hear some steps that you can consider, how to drive the meeting better, to show up that you are in control of the room, instead of letting the meeting drive you. He will give me very timely feedback, all the meetings I drive, all the emails I write, all the presentation that I make to senior leadership. All of his feedback are very actionable because I feel like he understood where we stand really well at how to position ourselves. I learned a lot of managing up storytelling and also corporate tactics from him and just from being on that team, so I think timely feedback, they're very important. You're definitely the type who seems to love your sponge. You would take that. I think other people would crumble under that kind of constant. Yeah. Hey. That was awesome. Do you want to talk about it? Do you want to talk about your presentation? Do you want to talk about your meeting? What kinds of people don't take that well and how come you were able to take that well? I think that's what differentiates from a fast growth versus someone who's not growing as fast, which is the ability to taking the feedback and address the feedback. I think it all comes down to your attitude towards feedback because to me, this is a little random, but this is a quote from Michelle Obama's book. Becoming? I think it's from becoming. I think one day, either Sasha or Maria were coming from school and they were talking about they don't like their math teacher. And then she was like, you don't need to like them. She got a math in her head and you need that. That's true. So, to me, I was there to learn. Yeah. I didn't know how to be a PM. Nobody went to school to learn how to be a PM. So, to me, I understand everything that my manager was teaching me and telling me was from a good intent because he wanted to see my girl. But you didn't take it personally. Exactly. Because to me, that's like him genuinely trying to help me with his feedback and help me grow into a better PM. So, I feel like when you see feedback as advice and suggestions and, you know, action items to help you grow, you wouldn't take defense to that if you take feedback as defense. Because also, think about it from their perspective. It's hard to give feedback. It's not a good thing to tell someone that, hey, I think you should do this better. Right. Like, just be better. Yeah. It's not an easy conversation to have. So, it also takes a lot of their effort to deliver feedback. Yeah. So, when someone give me feedback, we have the same on the team. Feedback is a blessing, always. And I always felt like I was learning whether, you know, sometimes you take it with a grain of salt. Sometimes I'm like, it's Friday night at 7 p.m. I don't have the appetite for this. I will check this. I want to stop feedback Friday at 7 p.m. and I cried. And I was like, I got a big text on, and I'm like, sir, please get out like, why do you do this to me and ruin my life? Yeah. Exactly. I mean, I definitely go through days where I'm like, okay, this is a little too much. I need a break. You're a lot right now. I'm giving feedback on your feedback, but you should time it better. Yeah. Exactly. But I think I always, you know, took it with, he's trying to help me, what he was, he's looking at us for me. He should help me. I'm your translator. Yeah. And I think because I was also the more junior person on the team, I didn't come from the perspective on this is how you're supposed to do things and I know how to do things. So I think to me, it's always like, wow, this is a new perspective. So I want to learn, I want to be better. So if you feel defensive about feedback, maybe check yourself. So then when you got more senior to principle slash upper senior and you got feedback from other people, like, did you ever have the, do you know who I am? I know who you're talking to. How many years have you been here? I don't think so because I mean, there are definitely time staff, you know, feedback can be hard to taking because you, people have bad days and I have bad days that work sometimes too. But I think if I just take a moment or if I take the weekend to think about it the next day, like, I would, you know, go to the person with grace, but like, thank you so much. I appreciate that conversation because I know it's hard on their end. You're too good. I mean, I think it can be challenging sometimes, but if you just take it with a grain of salt, people are trying to help you, I think in general. And your manager gives you feedback in that style, then how do you get feedback to other people? It's also very direct because I think being likable as a PM, like, you can't just all be agreeable. I think as a PM, you have to be very opinionated, but I think I've, I've seen how feedback can be given in a way that's positive, warm, but also very direct. So I think that's something I've learned in my career. There's some like tactics. I feel like people generally use this like you can acknowledge, you know, the work that they did show appreciation, but then at the same time, you can be like, Hey, here's something you can do better that we can help drive the outcome better together. So you'll frame it as I think there's a way for this to be more effectively done. Yeah. Correct. I think I think you have an opportunity to do something better and bigger, more efficiently, whatever that may be. Yeah. Yeah. Yeah. You do have to frame it like that. Yeah, you got to make it like really positive, like, wow, like I see, we can go far with this together. Exactly. Oh, it's just so against my nature. I'm just like, I'm with you, but at the core, this is a relationship based draw. I know. Yeah. Ellie, you're saying close. Shut up. You got to do it. You signed up for this job. Didn't you? And I'm like, yeah, you're right. You're right. You're right. My bad. So after six glorious years at Microsoft, what prompted the change? So there were really only two companies that I was really interested in. I want to stick. Everyone loved Figma then. I know. Yeah. It's like now's anthropic, but yeah, Figma had a moment. Yeah. I love Figma. I still do. I still love Figma. I do love Figma. I'm so interested to hear more about your perspective on product management, because, well, first of all, I've been out of the game for like two plus years, and so I'm just like everything you'll hear say from me and my friends. Right. I catch up with my PM friends and I get to share all the juices.
you sit in the gossip and I'm like, ooh, tell me where are the working, like, who ate you? Okay. But I know that PMs are in a very tough place, like PMs are really busy, layouts are happening, so PMs are overworked like crazy. At the same time, everyone knows that they have to learn new AI skills, but not every company is properly trained or set up for that, so it always feels like an extra side project you have to do on the weekends to catch up and catching up is like a full time job. And as always, this fear of, is AI going to replace me? Is my job replaceable? Am I going to get laid off? What skills do I need to learn to be more AI proof? Is this accurate and what have been the anxiety conversations you've been having with your PM friends? What is your take? Great question. While I think there are generally two camps, I mean, there's one camp that, yes, PMs are absolutely going to get replaced because I have friends who have now been asked to ship codes as a PM at a big tech company. They are now being asked to do more, even take on like design roles and then engineering design roles are merging as well. So that's one camp. There's the other camp of the conversation, which is we don't think the PM will ever get replaced because fundamentally the PM job is still very critical to all functions. You are essentially owning the problem of what we're solving. You understand the customer context. You are helping the team deliver and execute, but how we do that have really changed. So I think I am more in the second camp. I would like to think that it is still very difficult to find what is the right problem to solve. But I always have thought of product management from a servant mindset, if you will, because essentially I am serving my customer personas to help them solve the problem. And I'm also helping, I'm serving my team because I'm serving my designer and my engineering partners to understand the problem better so that they can come up with better solutions. I never think that PM is the smartest person in the room, but you are there to make the room smarter. And today I think we have all of these exciting tools and technologies to make people go faster. So if that means when design resources is really expensive, I have to do a fake my prototype, I will do it. Now it's just making things a lot easier, because I think even in my current role, and by the time I was leaving Microsoft, how we work have already really changed a lot. Well, I also agree, PMs will not, strictly because it's a people type role, versus like a visionary role. So that's one thing that's really hard for AI. The second is it's a relationship role, which obviously you can't really replace that. That's very difficult. That's why entertainment agents exist, so managers exist, and yeah, I don't, I just, that's like the human part. That's like the one thing, right? The one thing. Right. And so I also agree, but I do think that PMs without AI skills versus PMs with AI skills, like with AI skills, it's definitely going to get hired over the ones without. So you specialize in AI work, you've shipped many AI features across your time as a product manager. What is the surface there is a work that PM should build AI workflows for? What is actually happening today, where it is actually most helpful to make sure you like focused your AI knowledge on these workflows as a PM before I answered the actual, you know, tactical things, I think one should do. Let's start from the mindset, because I think that like mental model and not framing is really important, which is, as the PM, you should do whatever it takes to help your team go faster and the ones that will be successful, and this is regardless of being in an era of AI or not, is the ones that are willing to experiment and are willing to learn as state coachable and be curious. Actually, funny story, I was talking to one of my previous managers who now is working at a different company. They have leaderboards of tokens, and because he's a manager, he has access to see who uses the most amount of tokens, and to him, it's very obvious the relationship between how good he thinks this person is versus how many tokens this person has used. I don't like that. I know. I get it, but I have conflicting feelings. I'm with you with all of the, you know, news. Okay, okay, all right, so there's that, there's that direction. Yeah. I think it also goes back to the ego thing we were talking about. I think the ones that will be successful are the ones that are willing to say that, hey, here is a new way of doing things, and I'm willing to let go of, you know, kind of the skills of being honing for years, I'm willing to learn the new way of doing things. I think those are the people that are going to be successful. Hey, did you read the Elena Verna article yet? No, not yet. Those are some stack page. Oh, part of it is millennials have been honing these skills for so long that seems might be replaceable, and it's like the fear of the loss of what you crafted in all those, like the over decade, 15 years that you worked on, do you let go of that and just take on the new age? Yes. Because that's the sunkoss fallacy, right? No, but it hurts. 15, 10, 15 years, and you're just like, really, all that down the drain. But then you get to learn something new, how exciting. I think when you get to your mid 30s, you're like, I don't want to, like, I'm done. And like, if we just do the same thing, I've done it. I've put in my hours. People are tired. Are your friends not tired? Are you not tired? How are you not tired? I feel like I haven't hit that point in my career yet. Okay. I'll talk to you in two years. Okay. Sounds good. Yeah. Deal. Deal. Yeah. You got a lot of just energy in you. Yeah. I think the people really motivates me. Yeah. That's when you know you're in a good place. Yeah. I definitely have days where I'm like, oh, I don't want to wake up. I don't want to go to work. Yeah. But then I think about, I don't want to disappoint these people that are counting on me or it's dependent on me to be successful. So I have to do it. So the mindset for AI is just willing to let go and learn. Yeah. Go let go of the ego part. If you are so senior and you fell, I think that's why I feel there's like this chorus around how Gen Z is actually way more well positioned than millennials because millennials have all that history and that baggage of, I want to hold on to this thing that I've already built and honed, whereas Gen Z are so lucky to begin with AI and don't even have that some cost fallacy. There is no, there's no cost. There's just a new start. But you own your own destiny, right? I think you are well not always because I think there are a lot of things that's happening in the macro environment, but I think you are in the driver's seat of your career. One can be given the same job title, but what you make of it is really your choice for the ones that are still lucky to have hold a job today, maximize your time there. I feel like in terms of the skills, like we said, right, the fundamentals of the job doesn't change, but AI can help you go faster. So one of the biggest pain points I have as a product manager, and this is actually something I was spending the most time on, was transcribing customer meetings. Then you have to write the synthesis on my OIT Microsoft, I would like to send out customer meeting notes to everyone as well, just so that they understand, okay, from this customer, this is what we learned. But with AI, you can go so much faster. I actually just built an AI agent using cloud at my own work that takes all of the meeting notes, all of the emails, all of the Slack messages, and translates into a synthesis that has sent it to me, and I can proofread it, and I can decide whether I want to put it into my PRD or not. So I feel like that just create that collective knowledge for the team is very, very, it's just more efficient. It's very useful. I hate information synthesis, I hate transcribing, I hate suburbs, I feel like, what are they saying? Oh, right, that's right, that's right. I think the most painful part was actually listening to your own voice. I see, I can, yeah, I can imagine you at your own laptop being like, oh, why did I say like that? Why didn't I ask that question this way? Exactly, so I think that part is super helpful, synthesize. And I think the second one is doing customer and competitive research, like using cloud just so much faster, especially if you are working with some niche companies, I think having that analysis really fast is really helpful. And the third thing is something I'm personally very excited about is just prototyping, you know, with all of the stigma make, all of the visuals that you can make. Like we always know that design resources are so expensive. You don't always get a designer for every single one of your features. So I actually was showing one of my customers something, you know, like they give me some feedback on one of the features that I was working on. And then I was able to show them live that, hey, this is what the experience will look like. So I had some feedback and I was like, hey, why don't we just address it right now? So I was able to do a live live coding session with them. And then they can see that thick mob prototype changing real time. They're like, oh my gosh, this is so cool. I didn't know how easy it was because I think most people have this fear of, I have to use the cloud code from terminal and I have to type in like command line, it's so scary. It's actually really easy. I think the setup was actually the hardest part. But once you get through that, the setup on thick mob make, no, in cloud code. Um, I think number four is any kind of dog writing to give you feedback. Like if you need to write your PRD, if you need to write your scorecard, your telemetry, I think AI can do that sometimes better in my opinion. Your telemetry like your, um,
metrics for success and how would you ask it? Yeah great question. I feel like it's very scenario specific. Usually I think with AI what I see successful is you have to give it good examples. So I will feed the AI good examples of priorities with good telemetry and like I guess maybe I'm biased is the ones I've already written or sometimes I would look at other people's you know PRD I don't think so. I feel like I know the ones that I got good feedback on I would just you know feed it to my AI agent as examples and ask it to follow the same framework or I will ask the AI to do research on hey what about like what are some telemetries that you will use for this type of problem in the industry? Usually it gives me a pretty good response so I think any type of writing it can help accelerate a lot and I feel like with writing sometimes it's really hard to get started yeah like I think treating it as a brainstorming partner is also very helpful and then I think lastly just any sort of feedback because I will stress test any type of my writings be like hey if I'm presenting to a senior VP how would you up level this framing how would you change the conversation or sometimes I would have a really an author that I really respect for example Karen Ho who wrote the book Empire of AI I would be like hey how would you write it as Karen Ho because I felt like her writing is very succinct and clear so I want to apply to my world as well very nice if you had a bet your bonus on it what PMs do you think are going to get chopped? Spicy question I think because AI is really accelerating the way we work so much now it's very clear on the bifurcation now who's really good and who's starting to get left behind I think pre-AI would take me maybe a full week to write a PRD but then now with all my little agents with my customer synthesis notes it takes me a day maybe two days to polish it and present it to someone and it still takes you two weeks and you haven't even you know open it's too slow exactly it's just getting really obvious I'll just be like what what would we hire you for exactly two weeks that's crazy yeah and I think that goes back to the mindset on experimentation right if you're not willing to experiment with AI in different areas of the role that we just talked about including prototyping including you know writing e-vails fall of your features just like knowing generally knowing what's going on in the industry I think if you're not AI driven that just a very obvious signal to you know your peers or your leadership that you are getting left behind is it common these types I don't know if it's common because I think in my experience most people are trying yeah most people are trying yeah if anything most people are trying really hard yeah so I'm in the environment that's just very competitive so everyone's trying the second night I think going back to the fundamental of the PM role like when the code becomes so cheap you need to identify what is the right problem to solve so I think hot take PM with weak problem framing skills are going to get left behind yeah because they're just so clear that if you're going in circles with your problem framing you cannot bring the team clarity AI can clearly do it better and if that's the case that's very unfortunate yeah dude a PM with bad problem framing skills is like what are we doing here guys they could be you know screwed pre AI era too right but I think I think now they survived yes but I think now just getting more and more obvious like why do we new product managers for and I think those are the five things we talked about yeah I think as long as you're very strong on your fundamentals you should be good that's true any others also relationship building skills because you know AI can do everything really fast in an accelerated way you know it can seem to says no right PRDs but it doesn't have the ambition or the context or the relationship it builds with customers and cross-functional stakeholders so I think if you're able to build great relationships at work people love working with you you should be in a really great spot Ellie what is the secret to being a likable PM as a PM I'm a sucker for good framework so I'm going to try to give this a framework yo I love frameworks yeah yeah we are suckers for frameworks yeah we are confirmed yeah so I'm going to call the four C's context calibration candor and care yeah that sounds good it's like the five C's we know the four C like the engagement ring yeah oh the four C's of the five C's the carrot cut clarity you should know the best color one day one day yes no this is the four C's for being like was a PM yes hit it Ellie so I think the first thing is just about context like nobody like being taught what to do so a good PM always skip the team the why the why now and bringing this thing together to solve a problem whether it be you know custom scenario business goals the why that's the first C so the second thing is calibration which is really about tailoring your style to different people because I think different person have different needs they do so I think as PM's a really great PM would have the server mindset I would like to call it because you're essentially serving your customers by solving their problems and you're serving your team to go faster because the best PM's is usually not the smartest person in the room like I generally believe that my team my team is a lot smarter than me so I'm going to make them smarter by giving them the contacts and give them what they need I actually have a Google drive of all of the 101's I've had in diligent in my entire career and I would document I will actually so every single one on one every single time I start working with a cross-functional partner I will have an expectation setting me to went on do you write down all their children's names I do actually I do I am that person I would ask every single person I will about to start a project with who was the best PM you've ever worked with in your entire career it doesn't have to be a single person it can be multiple people with different traits but describe that person to me and let me be that person for you they're basically handing you the answer of what they like exactly exactly and I think that's the cheat sheet like in my career I've gotten a lot of feedback obviously and many times the feedback is conflicting because people are different I've had engineers that just really want something prescriptive in my priority basically spelling out this is the button this is how it's supposed to be but then I've also had engineers that just want to answer the problem and do their own explorations so I think depends on the individual that you're working with you kind of have to tailor your style which is why I think it makes PM a really difficult job because you're constantly switching because switching like crazy yeah contact switching and also switching kind of like who you are to them that yeah it's a true chameleon at work yeah yeah well yeah so exhausting but I think if you care about your team which is the third C it doesn't have to be so bad because I genuinely don't want to disappoint people that I work with I think with any job people want to you know show up at work every day and do a great job so I always think about how can I empower someone today to help them do better to help me do better so I think when you have that genuine care for people it's actually not that bad and lastly we've talked about this with feedback which is just candor I think a good PM is usually very warm very open but at the same time very blunt and very direct I've had to pull people aside and be like hey I need you to put a little bit more effort into this help me help you and you just sometimes need to have those very difficult conversations you can't just be nice exactly yeah because if you are just nice and agreeable you won't get anything done yeah exactly yeah that's fair I like it of course these yes for seats I know you said a lot of people from UBC asking for advice is PM still the hot job these days that they want I think so okay I think it's a very unique job yeah nobody went to school for it it's a job that attracts certain type of people I get this question a lot but a lot of new grads want to break into product or I guess non-technical people want to break into product as well so what advice do you give to the new grads who want to become PMs in this market it's a really challenging time a few things the first piece of advice I would have is to actually optimize for learning velocity but not for brand and title it's actually a very exciting time to be in AI startups right now because there are so many new ways of doing things that we talked about Gen Z are better positioned to learn these skills and basically not adopt all ways of doing things so you should recommend start as versus big corporate I think for new grads yes whoo I also think in big tech right now is very challenging because people are constantly getting laid off companies are constantly trying to bring them in the way of how we do things so I actually advise new grads to look for startups and optimize their learnings on the job yeah have a great manager like we talked about have a player coach manager I don't think startups have player coach managers I don't think so no because they don't have time you don't want to start it because you want to build you joined a big company because you want to teach that's fair yeah I still think there is a lot of merit to joining startups to learn because you're kind of just done into the deep end correct but I would say that the likelihood of you getting a good manager is really low it's a lot lower than big corporate yeah so it's like trade offs can you can you live and survive without guidance you can like watch them in the room you know but I don't think they will actively be there the way that your Microsoft Manager would.
they would never go to bad. They would not even remember to put you on the promo table. They don't even know that promo cycle's happening. 'Cause they're so busy with the next thing that they had to build. - That's true. - Yeah. - So I think it is high growth still. - Yeah, it is. - Yeah. - Maybe it's more high growth for the domain area versus how to be a proper PM. And you learn PM craft, you learn how to navigate corporate, how this gonna look to higher ups and to other cross functional stakeholders. But I think instead of that's less important and more about building. - That's true. - Yeah. - There's different learning. - That's true. - Yeah. - What are the youths asking you these days? What are they struggling with? - Like if I'm being honest, most people are just struggling finding a job. - Okay, yeah, that's rough. - Yeah, that's fair, it's fair. - So a lot of people are just asking about my career experience, but also know that it's not very replicable in my opinion. Like it's different times. - Different times. - Yeah, like you can be hardworking and never encounter the opportunities for it. I think it's very unfortunate. - Okay. - Let's say that we are new grads in 2026. - 2026. - What should we do? LEM's scared. (laughing) - And you wanna break into product management? - Yeah. - What do we do? Should we just, should we just like grill product problems? - I think that's one aspect of it because I think that comes up in interviews. You'll be well positioned to do that. But I think do an actual personal site project like get your hands dirty with the AI tools and maybe buy code enough. - Yeah. - And then defining this is the problem I'm trying to solve and this is how I solved it because I think the conversation very much transitioned from, this is how we can talk about it to, this is how we can show you how I've done it. - Yeah. - I remember there were some new grads reaching out to me, literally show me a whole deck and a mobile like vibe code app that he solved. - And I was very impressed. - That's awesome. That's when you know this person is gonna make it. - Exactly. Like I think that bias for action never goes away. You can kind of spot that trade in people who you just know that are going to be successful. - Yeah, I think I agree. I think if I had to start over and try to break into the industry, I would target the companies and build a companion app for those companies and be like, this is how if I were to do community and then try my best to fudge some, I grow some amount of users, even if it's in the hundreds. - Exactly. - That's like totally fine and use UGC and content. - Yeah. - It stays and like post some LinkedIn to get like beta testers. I think going through that process yourself is probably needed to even be considered for a PM role. - And you can learn so much from it. - Yeah. If you are in a lucky position to even get a job interview, if you can show your learnings and this is how you did. And this is show them how you would operate as a PM. And I'd be like, that's very attractive. - I know that you are passionate about being a manager, which we need people like Ellie. We need great managers. We have a drought of great managers or potential manager to these. What kind of managers do you want to be? - I think I have been lucky to have had great managers in my career. So part of me really wants to give back that coaching culture. So if I were a manager, I would really help my directs hone their craft of how to be a PM. I would be a coach. And I think Microsoft had this really great model for managers is called the model coach care. So essentially you have to model the culture of the company wherever you are. And you need to coach hone the craft of your team. And then you need to really care and invest in your team's growth. So I think hopefully that's the kind of manager I will be. - You're in a very interesting place in your career where you've gone to this high super icy role. And then you're building and working. And then you have these hopes and dreams to become a manager. Is this what the direction you want to take your career? Like how fast do you want that to happen? How do you want to make that happen? Or do you want to keep building for now and then become a manager later on? - That's a very interesting question in this peculiar time. - A peculiar. - Yeah, tell more. - The trends that you're seeing is a lot of the managers are getting laid off. - Oh, why? - Because people are trying to cut head counts and then they're trying to reduce corporate layers. And for the managers are just managers who are not coaches and growing their team. It makes sense to not have that actually later. Because people generally want more builders, people who can actually do the work. I think right now I'm just trying to learn as much as possible, whichever role and opportunity I have. And I think hopefully the opportunity comes up naturally. The flurry wrap for better for worse. Any coworker here that comes through our doors must conduct a performance review. - Michael. - I know. - Legally, this does not affect your compensation, your title or your follower account, but it might impact your aura. - Okay. - Yeah, but you must be honest. And then I'll give you your rating at the end based on your performance of the entire day. Are you ready? - Yes. - Ellie, would you rather be right or be promoted? - Promoted. - Would you be down to make a million dollars when you'd have to be a course person at the Celacore Summit and Product Management? - Oh my goodness. - I'll do it. - She would do it. - Yeah. - Would you ever write a post starting with leaving my 500K tech job to start a dot, dot, dot. - Absolutely not. - That is awful. Putting your TC out there is just this tasteful. - Should filming a day in your life working in tech be banned or permitted in the office? - Band. - Are you living with main character energy or are you in your NPC era? - Main character always. - Meetings before nine a.m. - Human rights violation or a personal problem. - Personal problem because I do that. - I have seven a.m.s. - Well, you have global teams. That's just how it is. - I need to take a moment. - I need some space right now. - Actually, Chloe, let me ask you. Meetings before nine a.m. or meetings after nine p.m. - After nine p.m. - I worked for China. - Oh, that's fair. - So I worked until midnight. - I've done both. - That sucks. - At the same test. - Both is the worst. - Out of 100% for a promotion, what percentage is skill and what percentage is visibility? - Oh my gosh, that's so spicy. - Give me a number. - 40% skill, 60% visibility. - Makes sense, reasonable. - Is Genzi cooked or trainable in the workplace? - Trainable, 'cause who doesn't love optimism? - She's gonna be a great manager. Would you rather be a manager or a super icy? - Ooh, super icy. - If AI completely took your job, would you rather be a plumber, electrician, or a firefighter? - Can it be none of the above? - What else could you be? - Can I buy a martial art form in Japan? - I guess you can, yeah. - You found out that your underperforming work enemy that you hate is moonlighting two full-time tech jobs. Do you narc? - I'm not a snitch. I will not. (laughs) - Would you do anything? - Probably just gossip to my boyfriend about it. - That's it? - Yeah, that's it. - Is any PR no matter how bad it is, good PR? - No, I don't think so. - What have you been humbled by recently? - My job. It's a new domain, it's really challenging. - Xima, Xima's coming. - Oh yeah, absolutely, yeah. - Would you want to be light or be seen as really smart? - I wanna be light more. (gasps) - That wraps our performance review and you have received an exceed expectations. Congratulations. Thank you so much for being on Office Drama Ellie. I just have a few questions for you before we wrap. Where can people find you on the internet? - LinkedIn. - LinkedIn? - Yeah. - You actually respond? - Yeah, I actually respond. - Okay, so you're open to people called messaging you. - Yeah, absolutely. I don't always respond just because of how busy I am, but I try. - What would it take for someone to increase their chances for you to respond back to them? - I think just be yourself and tell me how I can help you 'cause I really like helping people, yeah. - Thank you so much, Ellie, for being here. I hope you enjoyed your time on Office Drama. Would you ever wanna come back? - Yes. - When? - Check with me in a year. - All right, I'll put on a calendar. - Okay, let's do it. - Yay! - Thank you so much. - Thank you. - What's up, everybody? It's your girl, Chloe, she back again, giving another shout out to Andromalamus on the Patreon. Hope you've enjoyed the BTS content and unscripted, unfiltered, chaotic thoughts on what's happening. Let's talk about today's episode, shall we? Let me start with. Ellie is not someone who's ever really online. In fact, I don't even know if she has an Instagram. There are so many people who are out there doing incredible work, who are great leaders, who are just amazing people to work with, but they are just not online. And I love giving a spotlight on these types of people because there are some people out there who do not deserve microphones. Too many people who don't actually do real work, talk about their quote-unquote success and their gurus and their courier coaches and their giving tips and advice. And then you find out through the great vines that they're just horrible, horrible people. They're just grifting. They're just like playing the game and for whatever reason, they're horrible people. And let me tell you this. So I love highlighting people like Ellie. She's such a good person. She's extraordinarily talented. She's a reliable product leader and all of her references absolutely love her. But I will tell you, between you and me, these types of people are always very nervous. Yes. Like, Ellie prepared like crazy. She was so nervous that her ex almost started flaring up. Like, these people are sweatin' their jittery. They're terrified. They need to drink more water. Their lips are getting dried. And I do my utmost best to create a safe environment for them to thrive. I personally think she did a phenomenal job for her first ever interview on the internet. And it is a privilege for me to create the safe space for them to share their journeys, learnings, and vulnerable moments. To make sure to be kind and supportive, I know you already do a good job already. I'm so damn proud of this drama llama community. Like, every time I see the comments, I'm like, damn. This girl is so talented.
Cooper people, y'all smart. Y'all are introspective. Y'all are super cool. Like if I ever meet you in the wild, just know, I am wildly interested in who you are, what you like and what you're all about. Because I think the listeners here are so ambitious and just like extraordinarily good people who do cool things, who aren't grifters, you know what I mean? Like, we are not the tech bro crowd. We are not like the hustle bro crypto, like it's a rug pull. Yes, we're not the rug pull crowd. I'm not a fan. So thank you for being awesome. Hope we keep creating this nice cozy corner of the internet. Hope our community grows. And as always, I will see you next time. Bye.
Podcast Summary
Key Points:
Ellie Ray was promoted every year of her career due to strong leadership support and a manager who provided timely, candid, and constructive feedback.
Her growth was driven by strategic framing, customer empathy, and the ability to build cross-functional team alignment through inclusive discovery sessions.
She transitioned from hardware supply chain engineering to a user-facing product role at Microsoft, where she shipped early AI features and worked on a customer data platform.
A key factor in her success was having a "player-coach" manager who invested in her development, set high standards, and consistently pushed her to grow beyond her comfort zone.
She emphasizes that PMs with weak problem framing skills are at risk of being left behind in the AI era, as AI can deliver faster, clearer solutions to complex problems.
Despite her success, she felt confined by her enterprise PM experience and actively sought roles in diverse customer domains to avoid becoming "typecast."
She believes AI will accelerate workflows in research, prototyping, and writing, but will not replace the human elements of relationship-building and customer empathy.
Her journey highlights the importance of adaptability, feedback absorption, and a growth mindset—especially in navigating career transitions and industry shifts.
Summary:
Ellie Ray, a former principal product manager at Microsoft, shares her rare journey of being promoted every year of her career, attributing it to a transformative manager who acted as a "player-coach," providing timely, candid, and actionable feedback. This consistent support helped her develop core PM strengths like strategic framing, customer empathy, and cross-functional collaboration. She transitioned from hardware supply chain to a user-facing product role, where she pioneered early AI features and worked on a customer data platform.
Despite her success, she recognized the risks of being typecast in enterprise PM work and actively pursued diverse customer portfolios to grow as a product leader. She observes that AI is rapidly changing product workflows—accelerating tasks like prototyping, research, and writing—but cannot replicate the human elements of relationship-building, context, and emotional intelligence. Ellie stresses that PMs with weak problem framing skills will be left behind, as AI can deliver faster, clearer solutions.
Ultimately, her career underscores the importance of adaptability, a growth mindset, and the ability to embrace feedback as a tool for improvement. She believes the future of product management lies in balancing AI-powered efficiency with authentic human connection, customer insight, and leadership presence.
FAQs
I was promoted annually due to having a great manager who provided consistent, timely, and candid feedback. He recognized my talent, set clear growth expectations, and actively pushed me to develop my skills, which helped me grow rapidly and consistently.
A great manager provides strategic framing, offers actionable feedback, unblocks the team, manages up effectively to show impact, and acts as a coach to help you grow. They invest in your development and create a safe space for learning and growth.
PMs with weak problem-framing skills struggle to clearly define the customer need or the right problem to solve. With AI accelerating product development, these gaps become more obvious, as AI can generate clearer, more effective framing faster than a human without strong foundational skills.
I started with software engineering internships but found I enjoyed asking 'why' questions about product goals and user needs. My dev manager encouraged me to explore product management, and I began building prototypes in Figma despite no design experience, which helped me develop a user-centered mindset.
Feedback is essential—especially from great managers—and I’ve learned to view it as constructive advice, not criticism. I take it with gratitude, reflect on it, and use it to grow, which has been critical to my progression from junior to principal PM.
AI has accelerated tasks like transcribing meetings, writing PRDs, conducting research, and prototyping. It enables faster iteration and helps PMs focus on higher-level strategy, customer empathy, and relationship-building instead of repetitive, time-consuming work.
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