Crafting a compelling career story

Nikhyl: Hi, everyone, welcome to The Skip. My name is Nikhyl Singhal. I’m your host and I'm delighted to be back after almost a 3 month hiatus. The big news is in April I made a decision to leave Meta. Many of you know that I am a product management leader within Facebook but over the last 6 months, I've realized that there's a choice that I have to make between where I want to go long term and how I want to help Meta kind of grow as an organization And, you know, it was a tough decision to transition out of a great operating role. I think that the company is a terrific company. It's continuing to surge. But my heart has increasingly been around helping people with their careers through the community, through the content, through some of the one-on-one coaching I do.

And I could tell that even within meta, that's the area that I had the most passion, the most opinion on.And so it became a very clear decision that the time is now to focus on where my heart goes and to really help as many of you in your career as possible. You might be wondering, well, what changes can we expect on Skip now that you're focusing on it full time? Well, I'll probably say two things. One is that I think I've been working for almost 28 years in different operating roles. And what I want to do is get a little distance from that before I go and create my next. I think that distance will give me a perspective will give me the opportunity to reinvent how I want to invest my own time between friends and family and health as well as my professional pursuits.

And I'm also very long term oriented. I'd like to continue to work on something for 20, 30 years from now. And so my goal is to build something in service of people's career, not just content and coaching and community. But really, a set of product and services that transform the offerings in that space.

I'm a little premature to signal exactly what I have in mind. Frankly, it's not even clear in my head and so you'll hear from me more and more on the subject. But for the short term my hope is to commit to the community, the product management individuals that I help coach, frequent content, and then also hear more and respond more to you. I've asked a number of you to kind of reach out to me, ask for help, ask for guidance, give me questions that I can use in future.

We've had some real luck with getting some folks on the show to take calls with me through coaching and then record them and share them out. But I haven't had a chance to really build, you know, enough consistency on that. And so my hope is to invest there in the short term and then ultimately, we'll work together on figuring out how does this turn into something that I think could really transform our industry when it comes folks tech careers.

Now, in terms of the specific content on the podcast, and you can expect kind of three different things. I think one is I would like to continue our coaching calls and anonymize them and share them out. I think they're the best example of real life situations meeting the frameworks that I've been speaking to.I think the second is that I want to go back in time and look at some of the content that I've shared over the last decade and really update that perhaps make it more concise, but also recognize that the world's changed quite a bit, both in terms of technology and product management, but also just the tech sector in terms of growth and opportunity.

And I want to make sure that those continue to exist. So, if you're just tuning in for the first time, or you've been a recent viewer/caller, then I'm hoping that you can kind of catch up with some of this content and this extra time will give me a chance to modernize those sort of greatest hits. And the third is over the last 2 years, I’ve been building a number of new frameworks on how we should think about very specific areas that can help your career. And today's episode is one of those examples where I really want to get into the importance of telling your career story.

So if you've been following along, you hear me use this word story quite a bit. And yeah, product managers tend to talk about the importance of storytelling. This specific topic is more around telling your own story, your career story. For example, I'll say, you should leave your current company. If you feel your story is rather shallow, not particularly compelling and if you're trying to decide between two jobs, before you look at compensation and manager, and perhaps how the company will grow, think a little bit about the story that you will tell after you transition out of the role that you're considering.

And if you compare those two side by side, the one with has the more compelling story is going to be the more effective chapter in your book of career part of that is the contents of the story. But part of it is the quality of your ability to communicate the story.

And what I find is oftentimes people that struggle with communicating their story are conflated with people who have a weak story to begin with. So the art of storytelling, your own career story is just as important as having a compelling story to begin with. By the way, this comes up in lots of places. It comes up when you're writing your 6 month review on yourself. It comes up when you're in an interview, it comes up on LinkedIn when you summarize. And a lot of people have anxiety, I would say the majority of people have anxiety, or almost sheer terror in putting pen to paper, because if you're a high quality person, often, you don't like talking about yourself. You like talking about the team. You don't like talking about your accomplishments. And frankly, it's sometimes hard to get that visibility into your own work and that distance. But unfortunately you can't really ask your manager how to tell your own story easily because often they're the customer in the performance case, or if you're leaving the company, obviously kind of awkward. And one of the things that I want to get better at is for those that work with Skip, they are able to tell their story more effectively.

And I think stories matter more of late than ever before. In the past, growth hid a lot of problems. You know, the company was growing, the industry was growing. So you were rising. The tide was raising all boats. Now, people are worried that maybe a person that was successful was just watching the movie.They weren't participating in it. And as a result, there's a lot more scrutiny on what did you do? And what did you learn? And what opinion did you have? And it's less about what level did you acquire? How many people were in your team? What was the success of the product? I see this all the time. Oh, you know, I was on a $100 million product and when I left, it was a $500 million product.We're supposed to ascribe value to that. Wow. Five times. That's a lot. If the person had done six times, I'd be more if they'd done three times, I'd be less, but in reality, they may have had nothing to do with that growth. In fact, no, probably single individual had anything to do with the growth. The story is about what was your role in that growth, if at all.

And increasingly there's a lot of skepticism for companies that are successful, that maybe the individual that they're speaking to wasn't really that involved. And I think the flip also applies. Companies have struggled with growth, doesn’t mean that the people that work there were problematic or weak in skill.

And so if your story is strong, but the company didn't work out, that might be more compelling than someone who happened to be enjoying a ride, the music stopped. And they don't really have the skills to be able to get the next job. So this is the reason why storytelling, especially of late, is critical. But lastly, if you're not convinced by the importance of stories and telling that story effectively, recognize that as a product manager, if you're listening, and you can't explain what you did concisely, how are you going to be able to explain a product or how are you going to be able to be effective at your job? How is anyone going to advocate for you in a promotion process or in an interview process? If they don't quite follow the work you've done?

So the art of storytelling your career is one of the key things that I want to ensure that everyone leaves this episode with. And so let's get started. I think the best way to illustrate this is through a case study. in a perfect world, I would have actually had a live call where someone walked me through their story. I would have hit pause and I would have said, listen, I don't find this story to be articulated well, but I think there's some substance here.Let's go back to the caller. Let's get engaged with that caller and figure out how to find those diamonds in the rough. Unfortunately, I didn't have one of those callers. But I will suggest that if any of you want to go through this case study approach in a live setting, I'm going to do one or two just because I think illustrating this is so important for career development. But today I'm still going to use a case study, I’m just fabricating it.

I'm going to use an example from someone who worked on Gmail during the growth phase and I'm going to read you a story, and then we're going to dissect it. And we're going to come back with something a lot more compelling. Now, if you're in the car or walking around or exercising, you're listening to me right now, you don't have a piece of paper or whatever, that's fine, because if it's a good story, you'll remember it after this episode.

My suspicion is you won't remember the original version and we'll be able to kind of workshop this in narrative, but the first one is fabricated. It's not terrible. I will just start by saying that. It's not a horrible story. I didn't come up with some facetious example of someone who went into sort of microscopic detail and got distracted. I think most of you that are listening are actually reasonably good at telling this story.They just struggle with making it compelling. It's very product-y not very market-y And this is a marketing effort. And this particular story is also fairly concise, which is rare.

Most of the time, my biggest pet peeve on listening to people's story is it takes 8 minutes. They go through this entire set of information.They're almost like running out the clock in an interview setting. And then you're sort of sitting there like, okay, where do I start? How do I engage? And the person didn't really leave me much. This is a more concise version, but it doesn't have the content that I would have expected.

Okay, here's an example of a story. in response to the question of: “Hey, tell me about your role at Gmail, and what did you do?”

AI: As a product manager for Gmail at Google, I was responsible for managing the full product lifecycle for several major feature areas. I owned strategy and execution on improving the inbox on mobile and worked extensively with engineering and design. During my time, Gmail was mostly on the web with a pretty basic look and functionality.

One of the first major updates was the introduction of threaded conversation views, which drastically improved how users could read through chains of back and forth emails. We also rolled out robust search capabilities that made it much easier to find emails based on sender, subject, dates, and more. As mobile adoption skyrocketed, we had to overhaul Gmail to create optimized mobile web and native app experiences across Android and iOS.

Features like push notifications became critical. The trend towards inbox overload led us to develop new organizational tools like tabs to automatically categorize emails as primary, social, or promotions based on content. We used machine learning for smarter bundling and surfacing of important messages.

Gmail became much more than just email, integrating Google Calendar, Tasks, Keep Notes, and even chat or messaging over time. We enabled third party add ons to enhance productivity with services like DocuSign, Trello, and more. Security and privacy were also major focus areas with increased safeguards around phishing, malware, and authentication.

We added granular permissions for users to control what data could be accessed by external apps and services. We had over 100 million installs on Android alone. iOS adoption ramped up quickly as well.

Nikhyl: That to me is a pretty typical story. Maybe a little bit more written and mechanical than what you'd normally hear, but you can tell it was sort of a little kitchen sink. It was a bit of: this is kind of what was happening on Gmail, and it's designed for you to be impressed. It's designed to say, wow, there's a lot of stuff that took place, but I'm a little bit challenged to figure out what specifically did this individual do. And so that's where the nature of my questions would then come.

Frankly, to be honest, I'm not sure I'd gain much. I don't know if you've gained much from this. You just heard what Gmail went through, and that's pretty typical. Either I'll hear a story that's like, here's all the stuff that was happening on the product, and then a little bit on what the person might have been involved in, or reverse, here's the stuff that I was involved in. I don't have the overall.

The key thing that I want in any story is I want it to be concise and at the right level. I want to be in a conversation with the person, so I don't want to overload the information such that the person doesn't have the ability to engage. I want to set seeds and almost tease things that I know the person will ask me about because that creates a dialogue as opposed to a monologue. That's what a great story does. I want it to be clear around the impact and the data around the person's role, and I absolutely want it to feel dynamic and interesting.

But I think that most people's stories, just to be honest with you, aren't that memorable. And so what I'm going to construct is a way to quickly hit on six areas that I think create the sort of template or the framework to be able to quickly walk through your career story and, you know, in a perfect world, you'd have, a 30 second version, the 2 minute version, and perhaps a follow on, which has answers to questions that will lead to about a 4 or 5 minute version.

So the six topics that I like to hit on, and they don't have to be in this sequence, but it helps is number one: I want the context of the project. Number two: I want a context of your role. Then I want to hear what the challenge was. Step four: what did you build and why? Snd then step five and six is what worked, what you learned, and then ultimately the conclusion. So you can get from this heavy amount of context, clarity around role, a clear understanding of what the opinion, what was built and what the learning was, and ultimately a wrap up.

Now, can we do this in two minutes? Let's try. Let's try to do this and see if it comes across more compelling.So, I want, in the first step here, to explain the context of the project. I want this person to understand exactly what is the product that I was working on so that they can quickly know what the weather's like, what the environment is like, and obviously, in the Gmail case, I pick because everyone on the call knows what Gmail is. But for many of you, you work at companies that are very important, but perhaps the individual on the other side of the table, or the reader on LinkedIn has no idea what the company does and certainly doesn't know your project. And so this sort of first 15 second teaser is important.

So, in this example, I would say: “sure I'm happy to talk through my role on Gmail. I wanted to work on consumer apps and move there for my PM role in ads.I was there for 2 and a half years at the time. Gmail was the established leader in email, but we were a web player. Mobile was increasingly where email mattered and we were worried disruption would come from a mobile first email company”.

Okay. I just made that up. I don't know if that actually happened.But the point is look how quickly I've connected the story around my career where I was in terms of prior chapters. Why I came to this role and then ultimately what the environment was like. We did that in like 20 seconds, happy to talk through my role in Gmail, wanting to work on consumer move from PM and ads was there for two and a half years.Gmail was the established leader, but was worried about mobile disruption.

That was information that maybe you could guess but it's pretty valuable. Because the point that I'm trying to suggest is who the hell cares what Gmail did while you were there? They want to hear your story.So that's the reason why we're leaning forward on this. and perhaps that you can tell by the way I told it, it's a bit more conversational, it allows the reader, or the listener to be a little bit more relaxed. When you explain it like you're having a conversation, people feel like they have an opportunity to converse. If you're explaining it as though it's a Wikipedia page, it's going to be filled with information, but it also sends this subtle hint that maybe you're worried about them poking holes or asking questions.

So, again, even though this is Gmail, we're having to place Gmail in an era, there's a lot of things that happen in Gmail over what it probably is 20 years of existence. Placing, it allows us to then say, oh, yeah, I remember that period of time.

Okay, let's keep going. so number 2 is we want to set up the role up until now, we sort of connected them to a bit of where I was in my career and a bit of what, in this case, Gmail or the product was going through. I didn't have to explain the product in great detail because I assumed it was Gmail, but I did explain a little bit of the market challenge.Perhaps that needs to be tweaked a bit, depending on your specific scenario.

Now we say: “you know, I was hired into the team responsible for the iOS app for Gmail. It had only existed for a year and most of our focus at the time was on Android. So I was the only PM for 18 months until we hired a second PM”.

Okay, this one's important. This is the most common mistake I see, which is people will say either what they did or what was happening in the product, but they don't explain it in context to the rest of the team. For example, if I read your accomplishment, and I see that the product has done fabulously.And you are one of 1100 product people on this project, I will feel differently than if you're one of three, or if you were the first product manager on the project, or perhaps you had never done product management, and you had seen something for the first time and showed a lot of success.

What does the environment look like from just the people side? Help frame all of the accomplishments and challenges going forward. So you can say, look, I came into this project and I did two or three projects across this product line. Project one, project two and project three all had this sort of commonality. That is very compelling. Then the next point is, Hey, this product existed, For only a year this in case the iOS app, and most of our focus was on Android. So you can tell that maybe this was not where leadership attention was when I'm setting up the story of well, eventually that changes.and then I know I was the only product manager for 18 months. Well, that's pretty big deal that you're making a note that, Hey, leadership was focused elsewhere. I was the only product management and then eventually the team grew.

So these are all important seeds that the person now has opportunity to ask about. They can say, Oh, well, you know, interesting. You were the only product manager. So what were the kind of responsibilities in that era? And then how did it shift as the team grew? Or you can make a note that, Hey, you know, it sounds like there's a lot of leadership attention to Android, where did creativity come from for the iOS app? It shows more weight, but it also openly acknowledges there was less innovation work and a lot more fast follow work. All of these points have been signaled without saying it, but what you've done is you set up a really compelling story.

Now, keep in mind, we’re about 30, maybe 40 seconds into our story and we have already seeded without even getting into detail as to what the person built. We've seeded where this fits in career. What were the overall environmental challenges? We've signaled what the team was like, and we've given people a flavor of what kind of product development was being asked during this period of tenure that the person's had all with very, very rapid information and being very light, being very understood, being very conversational. That's the type of story I'm looking for.

Okay. So now we're on step three and before I spend time talking about what I specifically built and why I want to frame the challenge often, I find that people will go from here's what the company and product did to here's what I built and naturally as you're going through it, you're asking yourself why. You know, I kind of get a sense of what the weather's like, I kind of get the sense of what your role and why you took it, but I'm not terribly clear on what was hard, you know, why did you end up choosing X versus Y? Why did the company choose that? Et cetera.

So the challenge is where I go next. So, in this example, we say: “at first Android, mostly copied features from the web, and we copied features into iOS then we realized that mobile patterns are just different than websites. People couldn't read or type long emails as easily, but they opened their email 10 times more than the web, just in shorter sessions. So we had to redefine everything on the app, from inbox to composition to how we organize the content. And as the only PM, I had to adapt this to iOS patterns and to prioritize what was essential since our engine team was about 20% of Android”.

Okay. Now, people are really getting clearer on what was hard, what the weather was like, what the challenge was, and then where the person fit in. This is really compelling now because people are starting to feel what the product was going through and then put your story in context. In this example, there's not only a clear understanding of the challenge, but it became clear what the team was asked to accomplish and then how quickly the person was able to grab on to the challenge.

But also I'm careful not to take too much credit. What I've been clear on is what I did and what I didn't do. Again, another big gotcha, Because a lot of times people will say, Oh, here's what I did. And it sounds almost incredulous that one person could do so much. Oh, you know, we launched this product and we had a billion users and it really foundationally changed the industry. And yeah, I was in my second year and I was the only person on the team and half the time, you know, we didn't even have the engineers, but yep, that was me, and they don't say that last part, but then you're looking at that like, well, there's no chance this person's story is real.

And now the credibility of your entire story is shot. Instead, in this example, I was pretty clear. Look a lot of the interesting work was happening on Android. The hard part wasn't me coming up with my own feature set. It was me really understanding that that team was much larger and I had to be a lot more efficient and judicious. So we couldn't do everything. So this became the product challenge. We also recognize that what worked in one setting wasn't going to work in the other. So, clearly, the person had to work with his counterparts or her counterparts in order to make this fly.

So, we're about a minute in, and we've effectively laid out the project. Now we're in a position to pivot and to get into much more real detail about me. I haven't used I that much so far, but I've laid out breadcrumbs. Breadcrumbs for future questions.You know, I've essentially made a point that organizational challenges were everywhere. We had a web team. We had an Android team. We had a bunch of teams focusing that one direction. I had to figure out a way to focus in another direction. So that must have been complicated working with different PMs, different organizations, et cetera.

Then you've got this innovation at scale, which I haven't demonstrated. I have not set up, being creative, which is a natural question for someone to ask. Well, it sounds like you were doing mostly copying. Where did you create? So, in my 2nd minute, I'm definitely going to get there. But because I know I'm going to get there, I make it clear.I haven't gotten there so far by creating that moment. Maybe they interrupt at this point. Maybe they say, well, it sounds like. You've mostly been copying. Can you give me an example where you're innovating? You're like, well, I'm glad you asked. I'm going to get there next. You can see that because I've sort of laid things out for things coming, that I've achieved, you've effectively given a lot of footholds for the person reading, person listening, person interviewing to engage.

Okay, naturally now in minute two, we need to get quickly into what I build and why: “I'd break down our strategy into three phases and phase one. We're focusing on the basics we had to ensure people could see all the emails and compose new messages in this new medium. Honestly, it wasn't too different than just opening the website on the phone, making that work natively. It was new for the team and we didn't have that many iOS engineers, but in phase 2, we moved into growth. Things were stable, we found that most people on iOS weren't using our native apps. They were just using Apple’s. So we did an extensive research study, both qual and quant, and we found four key areas of investment.My role was to prioritize these features with our leadership team. And I'm happy to walk through the specifics if that's helpful. And then ultimately our growth stabilized and we entered phase three. We started to worry the chat was growing exponentially where emails were going linearly. So we needed to innovate.So I suggested three features which simplify emails, all three of which remain today”.

Okay. This is a pretty compelling PM to be honest. You know, I'm excited about this story because I see a richness in lots of capabilities that I look for in product managers. I see being able to fast follow, managing organizations, the creativity on talking to users and looking at qualitative understanding of products, innovation, looking at data. Also recognizing there are a lot of opinions coming. There is prioritization. There is clearly an opportunity to work with leadership. I love the fact that this was structured in three phases because what it allowed me to do is not get so focused on some feature.

Now, in this example, I mentioned 4 features that we had to prioritize, 3 features. Another thing, naturally, what most storytellers do is they just start pounding through those stories: “Hey, let me tell you about this thing that we built and it got into the smart folder.” You know, the person's like you look you're not building freaking solid folders for my company, why the hell do I need to learn all about it? What I want to know is how do these seven things get prioritized and what was your process that you went through it. And maybe there was is it seven or is it seven hundred and or is it six? Or is it two or did you even not come up with any or did someone else come up with them? You know, there's a million questions that people are going to want to know, a recruiter is going to want to learn about in order to figure out if you're the person they want to place or even reach out to.

So the reason why I did it this way is I created a bit of a framework for the work I did over this 2 year period. And so I essentially said, okay, if this is me I want to have these three phases, the basic, the growth and the innovation. But then I created this sort of next layer of the onion.I'm like, okay, within that one was a fast follow. One was an innovation project. One was an area that require prioritization. Okay. Got it.

And what I didn't do is I didn't cover it. I bread crumbed it. So I'm giving you now the opportunity as the listener, the reader to come back and say, you know, there's a thing you mentioned about prioritizing.I really want to go into depth there. Because in their mind, they're like, that's the challenge I face here. That's what I want to understand. But it could be that you're talking to a company that's very early in product market fit.And so prioritizing may not be as important because they don't have customer feedback. They may want to know about, well, how did you start from the scratch? And maybe that's the area that you covered in phase three.

So what I'm trying to do is again, get me down to greater detail, by sharing my product structure, by sharing the challenges, by noting that I've been on this project for this amount of time, seen different movies. But by the way, there's some durability to the work I did. I didn't sit down and say, Gmail grew from this to this because of this feature, because that's silly. But I did make it pretty clear that there were seven things, some of which still remain in the product. And there were challenges along the way. So that as I set up the depth of what I'm doing, I've effectively grounded people in why this stuff actually mattered and why it was good. And keep in mind that one element in this story was that challenge was around us. And things weren't always working again. That creates a lot of empathy. Nobody has a product where everything's working, and if they do, they probably don't care about hiring you, or they don't care about entertaining you.

Ultimately, what I'm looking for from a career story is a little bit of authenticity around, yeah, this stuff is really hard. This thing didn't work out the way we wanted. The market shifted on us there's a competitor that came along. Those are the things that are existing in the person's mind that are reading your story and that need you for the next. So you want to, again, create those footholds for that individual.

Okay, so we're 2 minutes in roughly, maybe a minute 45. I think most people get about that much time if it's compelling and if you're moving and we've moved quite a bit from why we chose the job to what was happening in Gmail to the challenges that, you know, the, industry was facing to the role to the phases of investment to the type of things that I have now available to you to ask about when it comes to features, we moved 1 minute, 45 seconds in.

So we're set to now hit a pause and to say: “Hey, is this the level of depth you're looking for?” What I'm doing next is I'd want to walk you through a little bit of, how things worked, what didn't work and what I've learned. But I also want to go where you need me to go now. If this is a dialogue and obviously you can't do this on a written format like LinkedIn, but you can definitely do that if you're in a conversation with someone and you can even do it if you're at a cocktail party and you're just talking to someone about what you worked on.I mean, you wouldn't answer it in the same way. That would be kind of awkward, but you could say things like, hey, you know, that's kind of what I did. I'm happy to keep going, but, curious around, again, you can reciprocate, tell me your story, or you can say, curious if there's any of these areas that you know, interesting for you. I'm happy to go into more depth because what you don't want to do is go so far without checking in with the user. It's kind of obvious conversation dynamics.

But you also want to give someone the opportunity to say the magic words, which is just keep going. Because at this rate, I'm going to get all my questions that can answer my 1st round. Now, I'm going to go my 2nd round and that's good because it implies that I'm going to be able to repeat back to the next person what your story was. And that's our goal. It's does our story travel. Our goal is to make sure that the conversation we're having sticks enough that the person afterwards and say, hey, you know, I talked to Jane, Jane’s story is really compelling. I looked at all the things that she did, these types of challenges are like, much greater than the ones that we have. Love to involve Jane in our project.

That's the kind of conversation that's the goal of what we're trying to achieve. And that's in many ways, what we've achieved so far with a minute 45. In fact, you could probably repeat exactly what I just said, but you have no chance of repeating when I started the podcast with in terms of that original story, because it's generic and now we have point of view.

So now, just as I alluded to, I like making sure that the person has a clear sense of what I learned and what opinion we had, and maybe where things didn't work out, you get 10 times the number of points for opinions and learning than you do on facts on the ground.And again, if we look at our original story, it's very light on opinion, very light on clarity of role, very heavy on information density that you could probably guess by looking at. Oh, the person's been on Gmail for 2.5 years during this period, kind of guess what's going to be the challenge and what they were working on.

That's the distinction between the generic story and the personalized story. So, in this case, whether you get it in a Q&A, whether you present it more proactively, I want to make sure I'm leaving this person with this information because it's so valuable to hear. And this is the part that requires a bit of practice.

So you can come back and say: “okay. well, now I think back, I think we did a lot of things, right? It was smart to stabilize the app before we experimented with new features. But I think in retrospect, we shouldn't have copied the web. Instead, we should have just focused on fewer features really well integrated in the iOS. It wasn't about growing our install base. It was about convincing people to use the native app. Instead of the messages app built into the platform, and that required a few key features that people couldn't live without that just wasn't available anywhere else. What we eventually realized was that was smart folders, along with tight integration with other Google products like chat and Meet are things that are just hard to find elsewhere. And so that's why we invested in those products. Moreover, I'm really glad we spent less time trying to reinvent messaging. You know, email had really become a commodity and had effectively solved the user problem. So instead of trying to reinvent email, we started to integrate our product into other apps on their phone and recognize things like security and.phishing had become way more important than spam and organizing information”.

This may not be the perfect opinion because now, you know, again, I'm totally made up the product manager. I have literally no idea if this person really exists, but I've laid out opinions. This style gives people a sense of it was smart to do this. It was not smart to do that. We decided to go here for very thoughtful reason. It turns out it was a non obvious decision. Those are the types of moments where you're hearing judgment from the person. And that judgment, by the way, could have been done by leadership, and the person just by retelling it, but explaining it clearly, gives gravitas.

Let me point this out one more time because this is important. Many of you are saying, look, I am not the one in charge, making the decision to build feature A versus feature B. So, how am I going to drive opinion? Well, do you understand that opinion is actually happening? In the product that you are building, if you don't think there's an opinion anywhere in the ecosystem, you should probably leave because your story is quite uncompelling.

But if opinion exists seek to understand why. Not because some high paid individual is actually out there telling you what to do, but there must be some rationale. Hey, they're weighing A versus B. This becomes the more important thing. Now that I understand where they're heading, I can explain this was the rationale, whether it worked out or wasn't.When you explain it the way I just did, people are like, wow, this person understands the opinion and perhaps would have made the same decision or perhaps wouldn't have made the same decision.

But that's very valuable because you need an opinion to be an effective leader, product manager, however you want to call it. So I'm seeding lots of opinions that were in the ether suggesting I agreed with some of this. I didn't agree with some of this. Some of this was maybe what conventional wisdom suggests, but we went the other way. Those are always the best. Because if you said, look, we went and talked to a bunch of customers and they said that they would pay us $10 million if we went left and $5 million if we went right. So after a long debate, we decided $10 million is bigger than $5 million. I mean, what is that? That's not judgment. That's just basically looking at a number.

What you really want to know is, look, we looked at A, and we realized that there was many core customers that would actually service that. And we looked at door B, and there were far fewer. But by the way, the technology underneath us would have had to change radically. And we had an 11 person platform team. And those people all hated us. They had pictures of us in their cubicle and they used to put darts in us because we would come to them and we asked them to deliver more and more and they just didn't like us. And so frankly, my opinion was though there was more money and more customers left, we went right because I didn't want to get shot. And the reason why I didn't want to get shot is because our platform is rickety.

Now that sounds like an opinion. That sounds like a real challenge. And you might be sitting there like, Oh my God, I can't explain that, we look weak. I'm like, you don't look weak, you look real. And that's the point I'm trying to make is stories are compelling because they're real, they're authentic. They're clear. They're concise. They're not generic and abstract and highfalutin and they sound enormous because those don't exist. No one person can do big things in that way, but you can make opinions. You can understand what direction and you can articulate it effectively.

Lastly, we're just going to conclude: “Increasingly, I realized that I had seen what it takes to scale a mature product after a couple of years, there were options to grow a team, but I felt there were less opportunities to build new things in the project. Just given how constrained the work and the product was, I wanted to be a PM at a different phase of company. So I ended up running a search and getting pulled into my current employer Notion, which is far less established”.

Okay, I'm returning to your career is a set of chapters. Each chapter motivates the next. If you're talking about Gmail, you talked about what you did before, and you concluded where you're heading after. And again, by bookending it a little bit, puts things in context. It allows you to quickly move to next. If that's important to the individual, it allows you to suggest what motivated you. And in this case, it's very clear that the person was seeking something, signaling like, hey, it's a constrained org the product was constrained, maybe not the best time for you to be there. You don't have to say that. Oh, you know, my boss changed hands and I ended up getting reorg 17 times. And that was just the total cluster.

You don't have to explain it that way, but, you know, I signaled that that's the answer. So if they said, well, do you know, did you have an opportunity to stay there? And it's like, not really, we ended up reorg and ourselves out, as I mentioned. And as a result, it just made sense that that was the right time. You can signal enough But don't feel defensive, but be honest that, you know, not everything's rosy in this example in terms of org and product.

So that's the conclusion I'm reaching, not repeating back what I said, but setting us up in context to what might be next. Okay, so, in our conclusion of this episode, Things that I want you to remember. Six steps. We're going to start with project context, then we're going to go into role context, then we're going to talk about challenge and then what you built, and then we're going to talk about what worked and what didn't and ultimately drive some conclusion. Right?

So this is a structure less important to get it in this order. Very important to make sure that within a couple of minutes, you have these pieces, we’re going to see breadcrumbs, so you're not trying to jam as much as you can in 2 minutes. I'm not trying to get you to go on 3x speed and just speak faster to get it all in 2 minutes. I'm trying to figure out, what is the smallest amount of information that allows a conversation to take place, but does give people grounding of you did, what the challenge was.I'm also very careful not to over or under sell. Again, avoid trying to take credit for all of the things happening at the company industry project.

Be a little bit humble and be clear on what didn't work. What did work? What did you learn? You put all those things together. You have a very tight, authentic story that leads to a compelling conversation Now, for those of you that are like, look, I think if I worked at Gmail during this period of time on a product, that was super clear to everyone, I could tell the story really easily, just like Nikhyl did.

I have a very challenging esoteric example. I think the story is compelling, but I'm really struggling with the words. I'm kind of interested. I think that maybe 1 or 2 of these examples using real live ammunition would be great. If you are interested in participating in an anonymous podcast episode, where we case study this, I think this is so important telling your story effectively that I bet you will boost the industry as a whole. If everyone told their story as compelling as the work that they're actually doing. So, I would love to be able to audition a few of you and then maybe take a couple all the way through, share it as a future podcast episode.

In the meantime, I look forward to hearing from all of you on things that you want me to cover excited to be focusing more on skip. And it was a pleasure to be back in the saddle.

Thanks for listening to The Skip. If today's episode resonated with you, please consider leaving a review or sharing it with the people, you know, who want more out of their career. You can also subscribe to this podcast on Apple, Spotify, YouTube, or wherever you currently listen. You can also follow my newsletter on Substack and if you have questions or feedback, leave a comment or send a note on LinkedIn, Threads or Twitter. I try to answer each one directly. As always, I'm Nikhyl and this has been The Skip.