Product Management Executives share their keys to success in the Tech Industry | The Skip Podcast

foreign [Music] welcome to the skip podcast the podcast dedicated to helping you get ahead in your Tech Career I'm your host nickel Singh Hall and today's episode I have invited a good friend of mine named shreyas Doshi many of you may have heard of Shreya shreyas is kind of a guru in the product management Community you can see his writing on Twitter he and I met many years ago as we were both kind of navigating career together and recently he's focusing on giving back to the product management community and building coursework and really trying to scale up what it means to to be a successful product manager and a successful product management executive a few months ago Australia's tweeted out a node on how success in academics doesn't actually lead to always success in professional life I invited treas to talk through career plateaus what causes professionals to get stuck what causes them to have success at one phase of career and then get stalled in another I think that his expertise and his diversity of working in lots of different environments have led to some real insight here and I think it's very appropriate for a lot of folks that are listening that that are worried about being stuck or maybe that are feeling a little stuck and not progressing like they used to so uh welcome shreyas thanks for having me nikhil so I maybe we'll just get right into it I think that one of the things that I was struck by when I was speaking with you is just the density and richness of your like I always say that careers are made by not one Playbook but having many playbooks so that you can take up every new challenge is not a page out of a previous Playbook but it's a blend of all these different lessons that one's learned and you've been a Yahoo and Google Twitter and stripe for probably some of the best known and most impactful companies of Our Generation and you've been in product management in most of these organizations and you know I just have to sort of say that oftentimes we say product management works like X but I think in your experience I suspect that you'll find them that flavored quite differently any any broad guidelines around how these companies might Define product management differently yeah perhaps they can start with a stripe where I joined very early in the product management functions kind of Life at stripe that was actually one of the things that really excited me about the roll at stripe which is hey here you have an already fairly successful company so I was talking to them late 2015. and so they already had a you know few hundred employees at that time and they did not famously have product managers uh you know since the early days and um they were just starting the product management function there were a couple of product managers that they had hired and then they were talking to me and uh I was really excited about this observation of like here's an already fairly successful company uh and uh now they are gonna experimenting with product management that's the best way I could put it and they were pretty upfront about it that this was an experiment and I thought what a wonderful opportunity uh to really see if I really believe in product management I'd been doing product management for 10 plus years already by that time it's very if I really believe in the value of product management it's such a great opportunity to kind of figure out if product management can add kind of singular value at a company that has already been fairly successful so that was why I ended up you know one of the reasons why I ended up taking the role at stripe even though it was unconventional in many different ways like I went from being a you know a PM leader to going back to IC when I took this trip role so there were lots of kind of strange things that some of my peers you know rightly said hey are you sure you want to do this and I was like no I want to do this and then what happened was you know over the next year or two you know we were defining uh you know the product managers there and the engineering managers we were we were trying to figure out what is the role of product management uh at stripe uh and there were actually a few attempts that were made to kind of like write documents of like this is what product managers do etc etc uh and uh unfortunately none of that kind of really stuck because even you know one and a half two years in people were fairly confused but wait what what is it that product management does here uh because it's a very product focused company already everybody cares about the product Etc uh and so at some point I said you know what like let me take a stab at writing something about what the role of product management is at stripe now that I've been here a couple of years I kind of have sufficient context um and I ended up writing uh if I remember correctly I ended up writing just three sentences and uh it turned out that that resonated strongly uh with everybody and so for a while that was the kind of you know official kind of role description of product management at stripe uh and the if I can share like the first sentence that I shared and this goes back to my kind of strong conviction of what product management truly is uh what I said uh I'm paraphrasing is the role of a product manager um is to Define what product to build and to orchestrate actions across the organization to make it successful okay so that was the first sentence and then since this was largely going to be read by like analytical product managers engineering managers Etc their very next question is going to be well how do you define success so of course I responded to that in the next sentence so the second sentence was uh success is defined by user adoption and business value right and since then I've extended the definition to customer satisfaction user adoption and business value right uh and so you need to have some of those if not all of those to say okay you know this is successful uh and uh that was pretty much it right like and uh then I had an FAQ section of uh you know you know what is the role of an engineering manager in such a product focused company and whatnot um and uh there was this very important recognition that I wanted to share and this kind of like you know actually goes back to my experiences at these other companies as well such as Twitter Google and Yahoo where a lot of the confusion and even the friction around the role of product management uh comes in when uh people are expecting completely mutually exclusive work which is like well that work that's product manager's job and that type of work is not the product manager's job and what I have observed you know over the years uh you know in terms of sort of how to make product management and the role work is that it needs to be the most adaptive role within a team right for instance uh and this is something I kind of wrote in the FAQs in that PM role description at stripe is there could be situations where you have a product manager and an engineering manager working together or a tech lead working together on some product uh and there could be situations where the engineering manager is uniquely skilled on some user insight um maybe because they have experience as a Founder in that space or whatever it is right so in that case it is fine for the engineering manager to take on some of the uh you know user conversations or to take on some of the go to market conversations right and similarly there might be cases where a product manager is kind of uniquely technical in a certain area and maybe in this situation the there is no engineering manager or there's a new engineering manager it might very well be that the product manager has to adapt again and go a little deeper into the technical weeds and Technical execution than they ordinarily would do right so so this I this point I think I only realized this after like 10 plus years of kind of observing product management in many places but this point is I think not clear uh to many people and so people expect like no no this is the boundaries within which I will work and don't you do anything in here and you know what I'm not gonna touch these other things because that's your job and that sort of approach and that trying to put product management as a role in you know in a spreadsheet with cells in specific rules doesn't quite work in my opinion um so so that's my overall kind of perspective on from what I've seen it with these various companies and what I've seen works with you know good product management yeah maybe another framing that I use is gaps in glue I think that oftentimes where the glue function you know everyone has the boxes in their org chart and the lines in between the boxes often come into product management and I think your Insight is that sometimes people own some of those lines they have leadership around collaboration or they own customer relationships or they may have expertise and the Art of product management is to sort of adapt and and and pull back when needed and lean in when when needed as well and it sounds like what you're telling me is the the way you're defining product management sort of Applied across these different companies that was sort of a consistent theme that you saw in the function curious around are there areas that these companies did Define product management very different certainly maybe because of the industry or the culture or perhaps the scale of the product I think the big differences I noticed were Inseparable from the culture of those companies and there were many big differences in the manner in which product management worked and product managers operated and so some interesting factors were saved you know when I joined Google this was I think 2008 product management had been around at Google for a while by then but there was still this view that hey we are in much more engineering we are an engineering company and your role as a product manager is to support engineering in fact back then you know depending on which part of the Google org you were in it was often said that like everybody is just here to support engineering and that's your role um and uh you know that meant a very different way of approaching you know the product manager's work uh versus say Twitter which was uh a lot uh you know a lot more PM driven right it was uh it was you know it was expected that PMS for whatever reason the culture was such that like PMS are going to drive everything uh and sometimes it almost felt like some of the other functions there was lots of friction sometimes between pm and other functions because it was expected that like PM is the driver and everybody else is kind of the supporting function um and that caused its own set of problems because you know that's kind of like in my opinion that's not how you go about Building Product I saw you know something similar at Yahoo as well uh now I joined Yahoo you know during its better days but still like you know it was like around 2006 or so so again product management had been around for a while and there I saw it was even very Stark where you know that part I said where product manager's job is to define the product to be built uh well at Yahoo there were cases where uh you know some engineering teams would not build what it would seems like an obvious kind of you know feature teacher or error message or something because it wasn't in the spec and so you would have these conversations with folks of like yeah it wasn't in the prde but it's obvious that when the user Encounters this error we need an error message and the response used to be well but the product manager should have defined it right and so there wasn't that kind of agency and that you know user-centric view that many other functions had and stripe I think was the most interesting because um you know at stripe what ended up happening is that being customer Centric was just a core value that was applied across all functions um and being user-centric and even being product Centric was applied across all functions uh and so over there I found that my job as a product manager was uh the easiest in a way because I did not have to like convince people um that oh you know the product is not good enough we need to make it better in fact I would hear that from Engineers they would say you know what no no I need like two more days because I feel like this interaction is not you know well thought out or these this documentation is not great and we need to make it great and so uh so that was really fun for me as somebody who wants to build really excellent products that the entire fabric of the organization and because of the culture and it started with the founders the entire fabric of the organization was kind of you know pushing and like moving you towards building uh you know the best possible product that you can for your customers and and so I think a lot of these differences in the manner in which product management works uh are very deeply rooted in the culture itself of the company because again product management is such a you know broad function that works with so many other functions that um you know both the features and the bugs that come up are often just features and bugs of the culture itself I love that that's such a great statement and I think that with your depth of experience and diversity of experience in this important function product management you know I think you have so much to offer others one of the conversations we've been having over the last half dozen years is how do you scale yourself and your knowledge you know how do you give back um and and there's only so many roles that you can have full time and I think that you know looking even at your LinkedIn there's probably now I don't know maybe a half dozen to a dozen formal advisory rules that you've taken on and and I think that a lot of our listeners that are in this sort of act two of career where they're leaders they've had a lot of success they you know want to do more than maybe their day job they're asking this question around you know I I probably have knowledge that others would use I'd love to be an advisor but how does one go about doing that how do what kind of what kind of talent are they looking for companies why would they need me how do I plug in you know these questions and I'm sure you face those questions half dozen years ago you know how did you plug in to becoming an advisor and what's that relationship like and why has that been an investment for you yeah it's been such a such a fun Journey for me in this kind of uh this chapter of my career where I have at this point uh you know advised meaningfully advised more than a hundred companies a lot of most of the advising work I do is uh informal advising um and and then there are some kind of formal advising Arrangements that I also have where I work with Founders on a longer term basis whether it's six months 12 months or even longer sometimes and a couple of observations from my own Journey um you know I started uh getting this I did not plan for this necessarily but I started getting into this because uh you know while I was at stripe there were companies reaching out to me for you know leadership opportunities as they do I'm sure to uh you know many of your listeners as well and you know for whatever reason if the timing wasn't right um uh you know my the previous mode I took earlier in my career was just to say well the timing isn't right so you know let's talk again later uh but by this time I felt like I had both enough context and interest uh to still engage in a conversation with the founder not so much about not in the interview kind of setting but more in the setting of like uh uh okay so you know you presumably reached out to me because you heard good things from somebody else uh I am not looking for an operating role right now but um if you want to chat I'm happy to chat and I'm happy to you know provide my perspective on whatever it is that you're trying to do so that's really how it started and I had I don't know dozens of such conversations uh over my last you know two or three years at stripe uh and and frankly these things don't even take that much time because like on average it's just like one conversation a month or something like that so like anybody can manage that and the interesting that interesting thing that happened nikhil is um I'll share like what happened at my end and then at the Founder's end so at my end like again I had not planned any of this so I didn't know what to expect but I found myself extremely invigorated at the end of those conversations and by the way these were like intense conversations because like you know there's a very important problem or problems that the founder is kind of sharing with me uh and uh you know usually even if he had one hour we'd go one and a half hours sometimes two hours um and even at the end of it I felt like like a lot of energy so notice that and said okay that's interesting then on the other side sometimes I would ask the founders so like was this useful we just went through often it was the topic used to be like well I'm looking my VCS are telling me that I need a head of product a CPO VP product whatever uh what should I do and that's that's why they reached out to me to kind of like try to hire me um and so I say like I kind of like hear them out hear out what they're trying to do the strategy the challenges Etc their own kind of skills uh and uh their own kind of superpowers and then I would share my perspective um on things um and so after that I would ask them like so was this useful and often times I heard some version of the following I heard something like well you know you were one of the four or five people uh that uh you know I reached out to uh to kind of or talk to to understand this issue um and uh you know uh four of them said the same thing right uh and what you said you were the fifth one and you what you said was something entirely different um and your perspective resonated so I'm gonna try it out because sometimes say if it's the problem of it was not always the case but say it's the problem of okay I want to hire a head of product right uh the first question they ask is like what should I look for and who do you know right and so I would often tell them like that's the wrong place to start right it's like what are you really trying to do Etc like you know you go through that kind of like you know intense inquiry of like what are we trying to really do here uh so as so that we can set this person up for success and sometimes the conclusion that the founder would reach is actually I should not be hiring a CPO right now you know I should go hire a kind of like um you know um a mid-level experience PM uh and I should continue to do a lot of the product work and I should delegate certain aspects so that kind of this is a very important decision right like and so like helping Founders through this decision uh which like again like my job is not to tell them what to do my job is to help them figure out what the right thing is to do for them uh I heard often enough that like oh you know your perspective was different and it resonated and so that's when I started thinking well if I am deriving so much energy from this and if my perspective is uniquely useful then maybe there's something here right so that's that was kind of like the Genesis of this uh and then over time I just you know I was just like I kept and when I after I left Skype I kept myself open to yes if you know I'm happy to talk to energetic smart talented Founders uh with no kind of expectation of any kind of formal advisory relationship um and sometimes I would get on one or two calls sometimes three calls with them and in some of those cases they would say you know what I want to continue this I want to continue this and that's how you know some of my formal advisory work started was merely as a result of Founders wanting to continue that and my desire to want to continue working with the founder because I thought they were great yeah so hopeful there's so many nuggets in there I mean what I'm hearing is there is always opportunities because you're always getting unsolicited inbound and so you started paying attention to that and when you have those early conversations You observe two things one was how what was your energy levels after the conversation concluded and you notice that this was something that excited you which then meant you were naturally gravitated to prioritize and invest more and then the second is you got good feedback that you were saying something that you were clearly authentic and passionate about and you had Insight that others had had really valued and the combination was enough to lean in but you didn't start with i this 2023 I want five advisory roles and I'm going to run a process to find those you simply said can I help companies and enjoy it along the way and if one thing led to another and the company started to attach there was naturally some organic relationship that would follow because you wouldn't want it to stop on either side but if it turned out that after a couple of conversations it was enough that you either didn't have enough follow through or you had solve the Tactical problem well then it wouldn't make sense to be an advisor anyway and you part as friends and perhaps that leads to another future advisory role and so that looseness approach but opening yourself up to opportunity is what I'm hearing and I think it's great advice for folks that do find themselves this year maybe being a bit more constrained in their day job maybe because the role of shrunk or the company is not growing as much but there's so much activity in the industry and there's so much inbound take advantage of that to see if you can spark some desire and find some unique insights so I I really love that point I also noticed that I just got better as I had these conversations right like you know the first 10 advisory conversations I had uh you know I wasn't as effective and as useful as the last 10 I've had and that this kind of seems obvious of you know because you if you do something long enough you'd improve but my point is that perhaps you know early on I wasn't quite yet even ready to kind of like start an advising business right like I just noticed the quality of questions I ask now is so much better than the quality of questions I used to ask uh you know the first 10 or 20 or 50 times I did it and ultimately you know as an advisor uh there is Insight obviously and I share insight but the greatest value I can add is through the questions I ask you and I will now often ask you just like three to four questions and in many cases it like just the questions and the prompts and the follow-up questions and the discussion you as a Founder will end up within like and I've heard this often um you know that like oh I've been working on this for three or four years I spent an hour with you and I ended up with a completely different perspective on this thing I've been working on the last three four years and I look back and say like hey what did I do like I actually didn't do much other than just ask you the right three four five six questions uh and prompted you and nudged you and then you reached the the whatever conclusion that you were looking for on your own right like I did like I don't know about 50 different domains that I can give you a domain specific expertise uh it's for you to figure that out but it's the quality of the questions and so I do think it's important to understand that if we start approaching something from like I want to you know start a business or I want to start a practice here um we might actually lose out on that kind of like necessary uh you know early stage uh experience that we need such that we can actually build a very sustainable and a differentiated practice in these areas and I think there's questions are one of your many superpowers and I think I would say concise wisdom is maybe another way and you truly have embodied uh art when I look at your Twitter uh content because I've always struggled with communicating the concepts and the Frameworks that I've been building around leadership or career product management into short form content and you've managed to do it in that 140 characters I think that for those of you that are listening that aren't following stress on his Twitter feed you're really missing out because you get these questions you get these insights you get these clear where he's different from the the tribe that those those insights have been incredibly helpful to me to just sometimes just have vocabulary to frame something that's sort of ruminating but to have the words and to name it is so powerful and the combination of that and your small group super follower Community I think has been really insightful but I think you're on to something new lately is what I understand you're you're I think maybe you're you're a teacher by trade but you've been scaling up not only your content but you're you're teaching and I I don't know much about it but I read these highest Roi that I've ever spent on a weekend accelerated my product management career so tell me a little bit more about what you've been up to and and are are you effectively now teaching a course or how does that work yeah that's been um a really fun experience and I just started doing this about four or four or five months ago um and the way it started uh is uh as I was kind of you know after I let's left stripe this was in May 2021 um uh I decided for the first time in my career to take some time to figure out what's next I talked to a lot of uh people uh I think guys you and I spoke as well about sort of like what's next and how to think about all of that uh and I had just kept an open mind that like oh you know I'm gonna start writing a little more because now I have more time and I have now a followership on Twitter and Linkedin uh and then I was I'm gonna continue doing more of my advising work uh you know which kind of again started while I was still at stripe uh so I'm gonna start uh you know doing more of those things and as those started working very well and gave me tremendous satisfaction one of the one of the things I noticed is there was something missing so like my advising work was covering for the one-on-one deep uh impact uh really well right like whether it's like with one founder or a couple of Founders or with Executives at the company uh that was just deeply satisfying it was like going deep and having context uh over a long period of time and um uh a high degree of impact to one company uh whichever one I'm advising right now okay so that was taken care of the one-on-one then I had the writing which by that time was now reaching hundreds of thousands of people um so so I had the one to hundreds of thousands also covered now over there obviously um you know the impact is not going to be as deep with all the hundred thousand plus uh people uh but it's going to be very Broad uh and I started sensing that there was something missing which was um you know what about the one is 200 and one is to 1000 impact and the way it kind of manifested was I was getting a lot of requests for coaching yeah and I did not want to kind of start a conventional coaching practice uh because I was already already doing the Deep advising work and I felt like you know if I also start doing coaching then you know I'm just not going to be as effective with the Deep kind of strategy go to market culture advising that I do with startups so uh so that's when the idea of courses came about which is what if I can do coaching uh but through courses right and and so the manner in which now I've structured I have one course out right now which is about managing your product career uh where I'm sharing sort of you know 20 plus years of my own learning but also learnings from people I know um and uh also I interview uh you know product leaders and uh you know executive recruiters you and I had a conversation about that as well for my course um and I kind of like pack all of those insights into a weekend that is focused uh on sort of the end-to-end view of your career right from you know what sort of path do you want to create uh how do you build competence uh to how do you find the right companies because it's so important like a lot of our career is like really dependent on you know identifying the right company how to get hired uh how to negotiate a comp and like how to evaluate offers that's another area where I've seen people make so many mistakes where you did everything right up to this point but now you know you had three offers and you ended up picking the wrong one right like in hindsight the wrong one so is there a way to figure out like which is the right offer for you in a way that you minimize mistakes uh to sort of like how do you then get recognition within your company how do you grow within your company how do you get promoted how do you sort of you know plan for the right kind of ratings for your work that sort of stuff uh and then most recently I also added a section around how to deal with the tech jobs downturn that we are kind of starting to see here um so anyway so uh you know I've crafted that uh 800 people uh have already kind of gone through this and uh what I realized is my hypothesis was that uh if I structure this in a unique way and if I treat this course like I would treat a product and kind of basically just like product manage it uh such that I can have the right kind of effect on my users in this case my students um then that would be a you know wonderful kind of experience and hopefully useful for students and that hypothesis I would say has been proven at this point because um you know a lot of people have told me that like it just substantially changed the way they have they were thinking about their career you know they were just thinking kind of one track now they understand that for them there are actually various different tracks possible we go through a lot of exercises along the way as well uh for people to figure some of that out and then there's a community and various other resources available um so uh yeah all in all I'm super excited because now I'm able to fill this kind of 1 to 100 and one to one thousand Gap and kind of effectively what I'm trying to do nikhil is not not necessarily teach a course but coach a course right like it should feel like you are actually getting coaching from me because I just cannot scale to one-on-one coaching or even one two three coaching anymore uh and so as part of that I have these extensive AMA sessions where I'll kind of answer your questions and so on uh and then lastly people who take my course I want them to continue learning after they're done with the course as well I don't just want it to be like oh that was a fun weekend I learned a lot of new things new Frameworks met a bunch of people now I'm just gonna go back to doing what I was doing to solve that problem I've just recently last week launched something called Product club and so people who take my course are eligible to join product Club where they have an ongoing Channel with me there's a dedicated slack of everybody who took my course so now it's already 400 plus people who have joined product club and are on this slack and over there uh I will be doing monthly events with them where again it's kind of this AMA style I'll share what's top of mind and kind of again like in the spirit of coaching and group coaching kind of create a channel where I can reach you and I can address you know the questions and the challenges you're facing right now not just you know a month ago when you took my course so I'm super excited about that and now spending you know a pretty large amount of my time just focused on this well it's so appropriate for the listeners because many many of these listeners are thinking through their Tech careers and a lot of the questions you asked around decisions compensation thinking long term understanding how to navigate internal and external climates and downturns are all kind of dead on and so for those of you that that are thinking through you know those those questions you know burning a weekend to listen and learn from not only trust but from others that are going through the same problem I think is is a tremendous value add and what's also exciting to me stress is to hear that that's one that's only one class that you have in mind that there's others potentially coming and that there may be more more ways to sort of scale and product manage your wisdom which which I think is a great great way to frame it you know along those lines and along this sort of maybe pivoting a little bit to a tweet that caught my eye in July that had you know a lot of the characteristics of this ability to very concisely put language around something that I had been observing for decades you know and for decades you know looking at people that have had tremendous success and strength in academics you know you and I both are surrounded with folks in our industry who you know were at the top of their class from his prestigious University or Seto universities and had all the makings of just you know success in every way shape or form and what you find is they don't necessarily struggle on a consistent basis but they're just inconsistent there's almost no connection with their success 15 years later and their academic success some did incredibly well some never found their footing and some were in between and similarly if you look at some of the most successful entrepreneurs Executives and leaders and those that have Elite careers many of them didn't have tremendous academic backgrounds and so I've always kind of ruminated on this especially as you talk to parents who have kids that are so dedicated to trying to get their son or their daughter you know the best education the best school and that whole kind of rigmarole and you start thinking through well is this really that connected and I think you wrote this this really powerful the statement which is what we learn in school must be unlearned in business and in life and I just I thought that was so powerful and I I'd love to just to get your perspective maybe what what possessed you to to write this note and maybe we can go through some of the areas uh you know in this discussion but where did this come from yeah quite similar to you nickel I had been working with uh you know highly accomplished brilliant brilliant people um with wonderful wonderful resumes in some cases uh you know as peers in other cases is you know managers and in other cases as uh you know people who were on my team um and I started noticing and kind of asked myself the question of like well here you have somebody who just clearly has all the talent uh that you need to be highly successful in whatever it is that they're doing and yet the impact isn't there and not only that and this was especially true in cases where I was coaching mentoring or managing somebody because we would have you know deep conversations about this stuff um and yet you know both the impact isn't sort of in proportion to the talent and the potential but also they were just deeply frustrated with how things were going and uh and they couldn't quite figure out why things were not going the way they wanted them to go so that was that I I saw that often enough across companies and across teams and whatnot and I started thinking about why this might be occurring so consistently um and that's when I realized that a lot of now not entirely but a lot of um why that is happening is because the the things that you learn you know in your formative years um they work really well for you in those years in the academic context and then you know as many of us do we then tell ourselves a story that like if I do X I get y right and then we bring that story Into the workplace and actually early on perhaps at Junior levels it does work right at entry level uh it does work right because you have a boss and they will tell you like you need to do this and you go do that and uh and it's very structured and and you're given all the right resources uh there is no ambiguity uh and it works and so you say wow okay this works so let me do more of it right and then the organization recognizes you and now you are at the next level or the level after that and then all of a sudden it stops working and that's what causes that frustration which is like by this time now I've had you know whatever if 15 years 18 years of a certain approach that has worked wonderfully fully well for me look at my resume and now it's not working right and oftentimes what would happen nikhil is uh the first blame would go to the environment which is like oh this organization or this company you know it's screwed up in all sorts of different ways and if only we could align and create the right kind of optimal environment uh then you will see how much impact I can have right and so so you know and I've done so many deep kind of coaching conversations with folks on my team and others on this topic and that's what kind of led me to uh you know write this piece about the things we learned early on that work for us that then sometimes we have to unlearn later on this sort of career plateauing or frustration coming up in mid-career I think is what really connected me to the to the material I think concretely you mentioned that you know when you're in school you need to be good at following rules and following structures and yet in business breaking rules leads to outsized returns and you're often expected to create your own structure and we've talked about on this uh podcast how oftentimes managers are actually quite weak at creating the structure and letting you color within the lines particularly as you become a leader and feedback is extremely clear in school you get tests and grades and the goals are very obvious you get graduation and you get to the next level but in business feedback is actually quite rare and good feedback in particular and that there's such small differences between winning and losing it's not so concrete of a versus B versus C and timelines are often very short they're measured in a quarter or a semester or a year and then there's a clear ending you know I'm going to graduate at the end of this year go to school college but careers are you know 20 jobs 15 jobs 12 jobs for many people and the best rewards often take many many years where you see all these examples of we worked for six seven years before we found you know confidence or skill or or product Market fit so things are relatively short-lived so these are the things when it you know comes to these structural rules would would you say that now when you apply it to managers that might be in this mode where they're feeling stuck are they struggling with this and maybe a a better way to ask the question is what is your coaching advice for folks that are in this sort of rural feedback timeline it wasn't in the PRD so I'm not going to do it so they're very much sticking to the lines but we both know that leadership is often breaking lines creating your own how do you cook someone to see that and change that behavior the general theme I see often is this idea of you know well I need uh so this is like a you know a leader um whether it's a you know first level manager or perhaps even uh you know director VP level person um who says well I can I'm responsible for this goal or I'm responsible for this metric or whatever uh and the challenge is that uh you know the rest of the organization there isn't Clarity isn't there isn't Clarity on how this fits in and there isn't Clarity uh on you know just how much of a priority this is ETC um and and that often is a team that uh you know I have um dealt with as a manager or in some cases as I was coaching folks um and my Approach is to help them realize through a series of questions that effectively this is why you have this role right is like you know your number one job is to create Clarity in an environment that is extremely noisy is extremely complex and is by definition ambiguous right so so your job shifts from you know just kind of through sheer will and sheer discipline just getting things done because that's what you gets you promoted early on that's what gets you good grades right like there's a rubric uh you know the the teacher or the professor publishes the rubric and then you follow the rubric and voila you know you get the a grade um and that transition that uh you know the folks who are kind of sometimes feeling stuck uh that they need to go through is that oh now it is my job to create that clarity right like and there is never going to be an environment uh you know from this point forward uh if I'm gonna be operating at these levels where the clarity is ready made right uh and so so then once they realize it and look I cannot tell you that directly because if I tell you that it's not going to work you have to realize it yourself and that requires you know a series of questions uh introspection and all of that but once you reach that point now we are having a very different conversation right we are having the conversation of okay so so now how much uh you know how much responsibility are you going to take to tell uh the CEO that this is what needs to happen right how much responsibility are you going to take to tell your cross-functional peers uh that here's where we are headed uh and and then then we can start talking about okay now how do you communicate it what are the tactics and the techniques and the process that you use to communicate all of this uh across your organization in a way that the efforts are cohesive and and people are motivated and all of that right uh and so oftentimes you know people kind of jump directly to this which is like oftentimes you know a lot of times what happens is people people encounter a problem and they jump directly to how do I do this right um whereas like sometimes I have to help them understand like first let's understand what is your role and what it is that even needs to be done and when we can figure that out and it's the correct thing the how actually writes itself and I can help you with that but you know we can get to the how but we first need to understand what your role is in all of this and folks who cannot make this transition uh they kind of feel stuck in their careers and oftentimes they're uh you know the executive team uh the CEO is also frustrated that here you have somebody with great potential uh but they are not quite you know creating the clarity I need uh they're not quite creating the clarity for their area uh that will move things forward uh and uh you know I also see this tendency nickel sometimes in folks who kind of spent a lot of time in um you know very large companies because in very large companies even if you are at kind of senior director level and what not sometimes uh you are handed uh sort of like you know a recipe a roadmap in a specific set of things to do if you've been doing that for many many years and now you're going to a startup uh you're now all of a sudden going to be confused because there isn't that you know clear chatter that you've been given and I saw this quite a bit you know at stripe and also in places you know where I've kind of advised Executives have gone to startups from large company environments where they often felt like well but we don't know like you know hey it's so screwed up like the we don't have a clear strategy or we don't have uh you know there's all this kind of open questions that are not answered and then I have to help them understand yeah it's your job to create that Clarity to help answer those questions such that you can have that cohesive execution the things that come to mind when I hear you describe this is mindset and courage and what I mean by that is those that succeed in coming to the conclusion that you pose through questions that hey what got me here isn't necessarily what gets me there I need to unlearn maybe the things that I would even suggest are my superpowers or my professional identity here and maybe in the case of school my academic identity and I needed to come in with The Beginner's mindset that there must be maybe a different way of solving the problem that I'm not a victim to the ambiguity but that I own the ambiguity it becomes my problem not the environment or the company or the CEO or the management team's problem I am part of it but I think that even having said that that's a lot of energy that is not an easy task there's a reason why people don't take on more responsibility or go from these late stage to early stage environment because it does take courage you know it takes this interest in starting again and going through the process of relearning and maybe even unlearning and I'm curious as to how you think about this mindset and shift and this energy and courage required would you agree that that's important and perhaps how do you ensure that people have it when they're faced with this challenge I like the characterization of a lot of these attributes in terms of uh this term I encountered I think Eric Weinstein uh coined it called high agency and it is essentially the idea that like some people are just kind of high agency people and they just take on problems they with full ownership and they furthermore apply a high degree of creativity to solving the those problems and along the way they show a high degree of resilience and confidence um as they encounter challenges which are inevitable in complex you know high-stakes environments uh and so that combination of uh you know resilience and confidence and ownership mindset and uh the creativity and then lastly influential communication so those five things when we put together you get this you know idea of high agency um and I think that is again one of the key things I've noticed that um you know once you go from you know doing a job really well to needing to lead a job that needs to be done well to needing to lead uh many many jobs that need to be done really well that a high agency is the big differentiator between sort of like you know good and ordinary and good careers and really great careers and great impact um and I do believe that this is something that uh can be cultivated um you know now any kind of world-class levels of any of these things a lot of it is kind of you know inborn like sort of traits Etc but just because you know uh certain things like some people are just naturally great communicators right like they did not have to do much it seems effortless right but just because somebody is a 10 out of 10 Communicator just because they have some natural gifts uh that doesn't mean if I am a six that I shouldn't strive to be a seven eight or a ninth right uh and and so so I do think that kind of uh that that's where some of that mindset comes in as well which is like uh look oftentimes um you know I I share some of this in my course as well uh that you know one of my observations is that oftentimes especially as kind of you know leaders most of our problems are actually in many ways messaging problems right uh and because we need to be able to we know what the right thing is uh and however we got to that conclusion we know what the right thing is but there are so many challenges along the way to kind of message it in a way that resonates with everybody that aligns everybody that excites everybody right so it's a messaging problem so so so how do you deal with it right like if you're just focused on the content if you told yourself the story of like no no just the content everybody should figure this out on their own like why like why can't they figure this out like are they idiots right like I see a lot of that kind of you know approach and you know thought processes uh and and what you have to unlearn here is um now look like this is where you need to exercise the skill of influential communication which again one of the attributes of high agency and you know if a message doesn't resonate one way you gotta try it another way and in fact you know at higher levels your job is to just be a repeater right like you're just repeating the same thing over and over again in different ways such that it will resonate with people um and and you know like for instance one like very tactical example I'll use is some leaders will say you know oh I like sending written updates right so I will send emails and I expect the team to kind of you know I'll put my thoughts in I'll put a lot of care into it and and I expect the team to read it and kind of understand I have a large org so I expect them to understand what needs to happen and then it should happen right well it turns out if you cannot just think a little critically about this say you have an organization of uh 1000 people 500 people even 100 people or even 30 people it turns out that some people naturally resonate with the written word format right they love they devour your emails or your Google Docs or whatever uh and uh and it works for them and they get the message at the same time there are some other people for whom this kind of verbal communication is the thing that's going to resonate right so you'll have to go up there and this is something I had to learn as a leader as well you have to go up there and at all hands or team meetings or whatever you need to make appearance in every single team meeting within your org and talk about this because that's what they are going to really resonate with while the email people are like well this meeting could have been an email right and and then in some cases some people are highly Visual and so if there is a vision you want to convey you might even have to create some you know inspiring prototypes and inspiring mock-ups you know and and even though it's very early stage you might even have to do that because the words you know for some people just reading the words is not enough right like they need to see how it's going to manifest and the the moment they see that manifestation they are like aha now I get it right I did not get the email I did not get the Google Doc I did not even get the All Hands where we talked about this but I got the marks right or I got the customer story right so so this is an example of something where I find that like people need to kind of you know change the mindset of like now it's no longer about you know what medium you prefer what is your superpower it's about figuring out what works for your organization and then influentially communicating uh in variety of different ways so this is just one example but this is the kind of thing um that takes some leaders a really long time to sort of like you know come to terms with that's that last thing that I think is probably the other piece that I'd want us to emphasize for those listeners that are feeling like they're plateauing they're hearing shreyas talk about you need to take a bit of a step backward assess the needs of the organization take some agency take some ownership and then re re rethink your style rethink your approach the fact is that these things take time they are not going to happen overnight and why that's an important statement is in the past you might have been promoted every year you might have been a straight A student you might have found things come easy because the way that you think is the same way that others expect but now your organization's larger the tools need to be more diverse you have to own the ambiguity as opposed to be shielded from it and so it's not unusual for uh for me to see people who have had very fast starts to careers quote unquote hit a bit of a wall when they get to management when they get to even executive and that hit the wall might be them just working through the pain of relearning themselves relearning their technique and then they unstick and then they start moving quickly forward and so you have to have that courage that patience and that optimism that you maybe are a six today but when you're an eight things will unlock but I think if your mindset is this I must be doing something wrong because I or the environment must be wrong because I was moving so quick in the past perhaps it's exactly the opposite as we conclude I'd love to just maybe get a last few words from you on any additional advice you have for those that are listening that really feel like they're stuck a bit and that they're hearing your words they're understanding they need to go through this but any Beyond maybe taking your class any other ideas that might help them as they approach this sort of unsticking themselves from this sort of spot they're in the main thing I I would suggest that folks consider is that there are many more options available to you than meets the eye because I think we we do have I see especially in highly High Talent fast-paced organizations which naturally then like sort of you know there are many ambitious people in these companies um and a lot of times nikhil I see um people are just focused on the conventional path which is like okay I'm at L 8 the next is L9 and uh the one after that uh is going to take me two more years or three more years and that is a viable path for sure but uh it is not for everybody and I think people there is this kind of some almost stigma around [Music] you know oh if you are ambitious but if you are not VP by this time that means you know something's wrong with you or you failed or whatever um and it turns out that like that's why there are many people who reach the VP stage or the CPO stage and they kind of hate it because that was not the authentic path for them right or maybe they should have explored a few other things before uh you know they they tried to go for the CPO role or whatever that is and so I think a lot of people just kind of miss that and it's almost it's sometimes I feel like it's it's like uh you know a video game which is like okay the point of a video game is to get to the next level and if I do these things I get to the next level but it's kind of like you need to understand what awaits you at that next level uh you need to understand if um you know you have the right skill set uh you know just because you know just because the next level exists uh doesn't mean that that has to be your only goal even if say you have the right skill set uh maybe it's not the right time in your life right uh and uh maybe it's uh you know maybe maybe you would find more fulfillment uh in just staying at the level you are for the next three four years but trying different things right developing different skills um so so that's just like one aspect of the general point that uh I like uh folks to really think hard about is like just you know be rigorous about your career decisions and as product people uh you know many of us pride ourselves on uh you know making really great uh product decisions whether that's via marrying data with anecdotes Etc but we pride ourselves in making really great product decisions well like you we should be applying uh that same degree of rigor that same degree of thoughtfulness to the most to what I would argue is the most important product which is ourselves right uh and and you know I'll share a concrete example sometimes for instance here's how this manifest where you know folks feel like they have the right idea but they don't and then they make inauthentic choices so oftentimes I'll talk to somebody who's super ambitious say they are a big tech company like Google or something else and you know they'll they they want to figure out what net what's next for your career uh naturally the topic uh sometimes the topic that they bring up is like well actually you know three years from now four years from now or a couple of years from now I expect to that I I should be founding a company uh I want to do a venture back startup that's something I've always dreamed of and I I think I'm Gonna Be Ready life-wise Etc to do that couple of years from now okay great uh so then we start talking about okay what's next and so then they'd say okay in order to do that the next thing I need to do is I need to uh you know become VP okay and so I asked them like okay help me understand you know what your rationale is and it often boils down to like two things uh one of two things uh one is oh is that way I'll manage larger scope I'll know how to manage uh I'll I'll maybe own p l I'll know how to manage the company manage people manage organizations and that's a useful skill obviously as a Founder uh so that's one version I hear and the other version I hear is oh it might give me more credibility with VCS and whatever else that's roughly the two reasons I hear and then like I have to point out that like you know your number one job as a founder of an early stage venture-backed startup is not to manage an org right it's to build a product that resonates highly such that you reach this kind of product Market fit right because without that your old building skills or your old management skills are kind of useless right and let's face the reality that most startups never make it to that point right so just logically if we were to really deeply logically think about this in like rationally do it without putting emotion into it and without having kind of LinkedIn and we uh like just if we look at it rationally it makes more sense for you for over the next two years to figure out what skills you need to develop what product skills you need to develop right uh what design skills you need to develop or what domain skills you need to develop such that you maximize the odds that your startup hits product Market fit right nothing else matters until then and if there are gaps there let's go fill that Gap right and that might actually mean not going for that VP promotion because as a VP you're not going to get to exercise a lot of these skills that we are talking about because there are other people in your team that are going to be doing that right it might even make sense depending on your situation that you go back to an IC role right for an early stage kind of initiative that you take forward uh or it might even mean something else where you take a role which is not all that time consuming so that you can kind of incubate your new Venture um you know on weekends or in uh in evenings uh as you kind of embark on this right so again there is no one right answer for everybody but this is an example where I think most people assume that like oh this thing is the right answer for me but uh you know we've just got to think critically about it and we've got a like my I would encourage you to kind of a lot of these things happen because the ego comes into play right like we want that VP title and then we rationalize that desire with through some logical explanation and so we we really have to kind of like you know look at that a little more closely and objectively and you know the ego is there but like try to at least you know see that the ego is playing a role here have the courage to find your own path recognize that the path that a company's laid out isn't necessarily the career path for you and and I think embrace the opposite of conventional wisdom whether it's strength and academics don't lead to professional success or getting that VP maybe the exact opposite thing to become a great founder or perhaps even to drive fulfillment and career maximization and I think that a lot of the courage is to find your own path to reinvent oneself to take that step backwards and and have that beginner mindset for your own career which is you know ultimately the most important product so trans thank you for joining me today uh for those people that are listening that want to get in touch with you what's the best way to do that well obviously put it in our show notes a few critical links but how do you want people to find you so I'm on Twitter and on LinkedIn so feel free to follow me on either of those platforms feel free to you know message me my DMs are open I cannot answer every single DM but I try so I would love to continue this dialogue well thank you for joining and uh and and we are more than excited to have you back for a future episode thanks for having me nikhil this is a blast [Music]

Channel: The Skip

Views: 9,556

Keywords: nihkyl singhal, shreyas doshi, the skip podcast, career frameworks, tech career podcast, cpo, facebook, twitter, linkedin

Id: y_TnXtnY3QM

Length: 71min 6sec (4266 seconds)

Published: Mon Feb 27 2023