challenging conventions: a deep dive into the complex world of product management
🚀 ready for a paradigm shift? tune in to our podcast for a dynamic discussion with a seasoned product management pro!
are you eager to revolutionize your understanding of product management? join us on our podcast as we bring you an exhilarating conversation with a seasoned product management expert. get ready to challenge the status quo and gain fresh insights that could reshape your entire perspective.
🔍 key takeaways
in this episode, you'll uncover eye-opening revelations that could transform your product management approach:
rethink the conventional focus on profits
demystify the concept of product-market fit
discover the pitfalls of feature factories
navigate the effects of leadership transitions on products
learn to strike a balance between passion and practicality
🌟 power dynamics in product management
listen closely as we dissect the intricate dynamics that define product management triumphs:
explore the impact of strong personalities on product outcomes
understand the pivotal role of data-driven decision-making
empower your team to craft solutions with a lasting impact
build a foundation of trust and accountability for guaranteed success
learn how to effectively gauge customer value to refine your strategy
🔥 lessons from the trenches
gain valuable insights from real-world challenges and experiences:
discover how to maintain integrity in the face of adversity
navigate job exits with grace and professionalism
grasp the evolving nature of product-market fit
understand the significance of delivering customer value
🔑 final thoughts:
as the episode concludes, absorb these essential takeaways:
embrace personal growth through challenges
anchor your success in a value-driven product management approach
🎯 ready to dive into a transformational podcast episode?
don't miss out on this enlightening conversation that has the power to redefine your perception of product management. tune in to gain a wealth of insights and strategies that could reshape the way you approach product creation. listen now for a truly transformative experience.
transcript
josh: 0:07
welcome to the disaster recovery podcast. i'm your host, josh santo, and this is the show where we reveal the untold horror stories and hard-learn lessons of software as a service start-up life as told by the SaaSholes who lived through it. their stories about the managers, departments and companies they worked for will leave you thinking what a disaster. our mission is to help you bring order and sanity to the chaos you will undoubtedly encounter in your own adventures in SaaS. there's stories and conversations with our guests who have been there and done that in all aspects of sass from sales, marketing, product and more you'll get the tools and insights you need to recover from disaster. on this episode, we're examining why building a product just for the sole purpose of making money by any means necessary including things that you probably wouldn't once said out loud versus solving an actual problem and bringing value, how that's a bad thing. we're going to talk about the failings of feature factories and how to know if you're in one. we're also going to dig deep into product market fit, what it feels like when you have it, how fleeting or elusive it can be, and the role of executives or leadership in changing the trajectory of a product or, ultimately, a company, and we'll also dig into why it's important to balance enthusiasm about your company, about your product, with a healthy spoonful of practicality. slash thinking for yourself, slash skepticism. now, i know i certainly learned some tough lessons firsthand when i experienced similar situations, so i can't wait to share the story of our next guest very similar but different experience. speaking of our next guest, he has nearly a decade of product management experience in saas for major, established companies and up and coming startups, and he's held a wide array of positions within software companies, climbing from a starting position as product manager to eventually being in charge of an entire product. we're going to hear about his experience navigating the challenges of maintaining product market fit while the company undergoes changes. and before we do, as always, a quick disclaimer the stories that we share here on the disaster recovery podcast are based on anonymous, individual experiences at real companies. the goal in sharing these stories and perspectives is to help fellow SaaSholes learn from each other, get a much needed sanity check and build empathy along the way. no specific company or person is mentioned, so if a story feels like an attack on you or on your company, we really encourage you to reflect on why you have a guilty conscience. and with that, let's get on to the show. i just want to take a second and thank you sincerely for joining the disaster recovery podcast. i'm really excited to chat with you today. i saw the experience that you had and i thought you were a perfect person to reach out to talk with us about product management. so thanks again for being here today.
guest: 3:19
thank you for the opportunity.
josh: 3:20
well, look, we'll get right into it. i am very curious. i've got my own perspectives on product management and what makes a good product manager, but i've never actually worked in product management. closest i've gotten is product marketing manager. so the first question i want to start out with to you is how do you define product management?
guest: 3:42
that's a great question. product management, in my opinion, is the privileged opportunity to direct the limited resources we have in life in a way that adds value to the world, by building meaningful products, truly meaningful value, and this is true for software and hardware and span's industries.
josh: 4:04
okay, so the way that you look at product management is almost like a life philosophy and not just an important aspect of a saas business.
guest: 4:16
absolutely.
josh: 4:19
where does that perspective come from? where did you learn that?
guest: 4:25
i think it evolved over time, as i was fortunate enough to be part of organizations that took their product portfolio seriously, and i was able to see the time and investment required to deliver something meaningful, something of value, and there's no shortcuts to doing that right.
josh: 4:50
shortcuts are never truly worth it in the long run, and that's one of the things we talked about in a previous episode the sacrificing of the long term in favor of the short term, and how that's a problem, particularly within saas companies. i'm curious did you learn this from a mentor, or were you a part of an organization and a team that you saw just working so well together that it led you to your understanding and perspective that this is really about finding ways of building meaningful products that add value to the world? so this is a very interesting philosophy, one that i haven't encountered with the product managers. i've worked with, or even talking with different product marketing managers and the product managers that they work with this perspective that product management is really about adding value to the world by building meaningful products. was this something you learned from a mentor or an organization or a team that you were a part of?
guest: 5:59
i think it's a mix of great mentors, being fortunate to be on great teams, as well as being able to participate in really great products and product launches, as well as being able to see some products that maybe weren't as successful as hoped, and to be able to take away some of those lessons.
josh: 6:23
so this is something that you really developed drawing on your own observations and even moments of inspiration, and that's what really led you to this understanding that it's not about building a product. it's about building something that adds value to the world through a meaningful product.
guest: 6:40
that's right. a lot of folks will talk about product managers solving problems or solving pain points, when really what i've seen is in order to have an outsized or a disproportionate outcome. it really is about finding a way to add value, and if you find that way to add value, the rest tends to fall in place and folks will find your product.
josh: 7:15
now, in that example that you shared, you know it's more about solving. it's not just solving problems, solving pain points, it's adding value. how are you defining the difference between those? because when i hear that, it sounds to me like if i solve a problem, i am adding value, but it sounds like there's more to it from your perspective.
guest: 7:37
yeah, that's right. solving a problem does not require an elegant solution. solving a problem could require a complex solution, it could require something, or it could be solved with something fraught with friction. that might not be an enjoyable thing to do. i think the department of motor vehicles often gets a bad rap in this way because you're able to complete the tasks that are required, but it isn't known to be a wonderful experience. it isn't the same as going to an apple store and buying a device. there isn't that magic that you feel in some experiences when you're solving problems simply, versus when you are adding value and delivering that wonderful experience in doing so.
josh: 8:26
got it. this reminds me of the time. i'm not very technically oriented or mechanically oriented. i'm a terrible handyman and it's something i aspire to be better at and i work on, but i'm terrible at it. i say that because my wife had a 2003, 2002 nissan xterra and this was like four years ago, so this thing was already up there in age and mileage and we came home from vacation one day and the vehicle would not start. i know enough to check the battery first, and so i did. i took the battery out, i took it to like walmart or something. they tested the battery and it was dead cool. i got a new battery, i put it into the vehicle and all of a sudden, the brake lights came on. now i think i got. my problem is the brake lights are just on. i took some time. i dug into youtube and different google searches and i found that with duct tape and a penny i could fix the problem. and i did, and i think that's a good example of what you're talking about, which is i solved the problem. it wasn't necessarily in a sustainable way. sure, it got done, but there's a lot of risk to the way that i went about it both risk of me not being able to undo some of the things i had to like take apart and put back together and move around. as well as what if there was a bigger issue that i was just treating the symptom on and it actually turned out to be somewhat dangerous? so that's what i think of whenever i hear your perspective on solving a problem is not just checking the box. there's something more to it. there's something that brings maybe a bit of surprise and delight to it.
guest: 10:12
that's right if we have a certain amount of resources to allocate to fixing a problem. in this case, you're fixing your wife's nissan suv with a little bit of training or perhaps a little bit of guidance. the question is, how could you have solved that better? and i think that's where product managers, again, in my opinion, should always be tasked with trying to solve it better. we're already making the effort. let's do it great.
josh: 10:45
i like that. it's about trying to solve it better. i think that's great and i love that we started out on a very specific definition of product management. clearly you've got a lot of experience with that. you've worked with different teams, a lot of different individuals throughout your nearly a decade of product management experience. let's talk about what you see that people get wrong about product management. what comes to mind with that question?
guest: 11:16
often product management is understood. we often get the question what do product managers do? and it's a fair question because it's a title that hasn't been around for a long time. but the skills and the responsibilities have been identifying a market, identifying an opportunity, identifying a way to solve that by adding value. those are things that have always taken place. i think product management has been the synthesis of those sets of responsibilities into one role, so that you have a holistic picture of all those pieces, versus it being distributed amongst different departments. product managers are not wizards. product managers don't write the code. product managers do not often come up with the final design specs for something they can build. product managers are there to provide that direction, to informally lead a group of people to that desired outcome, that desired value. and i think, interestingly, product managers often get hired for their brilliance and understanding the market and the users and the opportunity. and product managers often undergo grueling interviews and i encourage your listeners to just search for what product management interviews are like. and it's funny because even after going through all that, product managers are often usurped by strong personalities in the form of my way, or the highway leaders, or very strongly opinionated leadership teams, often whom fancy themselves as having a very clear and valuable product opinion. i think what often happens is folks get excited. folks want to have an impact in the shape of the product, and sometimes that may not manifest in a way that does add value or that does solve the problem in the best way for the people who are looking for the value.
josh: 13:32
that idea of being usurped by a my way or the highway leader. are we talking like executive team? are we talking like a very vocal sales team? because i've certainly seen that, yep.
guest: 13:51
all of the above. i think it depends on the characters you have, it depends on the departments involved, it depends on the decision being made. so it varies, but it's not uncommon to have folks with very strong opinions. and i think the other thing that's important to highlight is no one is folks are always coming with their best intentions. so a my way or the highway leader or someone who's coming with an opinion and a decision that may be partially informed isn't coming with that opinion because they're trying to do the wrong thing. they may have different motivations or different goals that may not be apparent to everyone else that's involved, sure.
josh: 14:39
yeah, i think that makes sense and i think that that's something you see, not just in product management. i've certainly worked in marketing with strong leaders who had a very specific perspective on the way a certain campaign should go, or positioning, or messaging, or whatever the case may be and there has to be some sort of balance. leadership does need to provide a direction. how do you balance the ideal role of product management with a very structured direction?
guest: 15:16
great question, and i think that goes to another common misconception about product management, and that is we're able to synthesize all of these inputs, because there are differing levels of opinions and folks have different levels of decision-making power. it's one of the most difficult things to do in product management is negotiate that compromise and outline that clear path, given the myriad of opinions that come into what the product should be doing or how it should be heading, or what the strategy should be to outline the next three, five, seven years. so it's definitely part science and something that product managers spend years trying to get good at.
josh: 16:18
you know, you brought up this idea of people having like different opinions, which is anytime you work with any person, you're gonna run into a conflict of opinions in some way, shape or form. i'm curious on the topic of product management what is a strongly held opinion, either in product management or about product management, that you completely disagree with?
guest: 16:44
wow, i think there's a little to unpack there. first, product management does not exist for the purpose of rubber stamping other teams or leaders' opinions. all too often those opinions that i was talking about and the direction of the product don't see eye to eye, and i've seen situations where that results in the product team being changed or pruned and often holding the bag for what's viewed as a lack of innovation or other business shortcomings. and i think that leads to the next level, which is you can't fake product market fit. so if we're in a state where we're rubber stamping requests, customers in the market are smart and they know better it'll start to come across as though the product and the company are simply out to make money, which is not a bad thing. companies exist to make money, but it has to start with adding value and, as a result of adding value, being able to turn a profit as a company. if you add that value, the success of the company will more naturally come. if you are sacrificing product market fit and you are simply searching out profitability, it can have a critical impact on innovation and can turn you into a mediocre at best kind of company. i think it's more important to have a good understanding. it's more important to empower the team through data research, customer interviews, market analysis, competitor analysis and let the product team formulate an independent opinion on what to build for whom and why, as well as articulating why it's worth paying for and how it adds value, and then bring that forward to the leadership team as an independent opinion, versus starting with the other end of it.
josh: 19:01
i think this is interesting. this sounds like an opinion that you wouldn't necessarily hear anyone say out loud. you would never expect to hear a prominent figure at a startup or whomever to say hey, product management team, your responsibility is to rubber stamp these ideas. i'm gonna come up with them and i want you to just say yes, we've quote unquote done the research and the analysis and what you say is accurate. however, it sounds like what this is coming from is the actual application of the opinion, and i think that's an important thing to call out is no one is out there saying product management does this. however, in the actual day to day, there are these experiences in which it is dictated and it's either get on board back to your comments about my way or the highway. it's either get on board or get out of the way, and the perspective that you're bringing up is that it's really more of a question of like the better way to approach. it is a question of how do you empower these individuals that have been hired as product managers. who are the people responsible for understanding what is the problem that needs to be solved? who has that problem? do they even care about solving that problem? would they be willing to pay for it, and so on and so forth. i think that's an interesting point.
guest: 20:31
that's right. often the term disagree and commit is thrown around by leadership who want the team to adopt their opinion. and i was speaking to a product manager yesterday at a large b2b saas company and it's the same thing there. there's a group of approximately eight individuals who make all of the decisions for the product. seven of those individuals aren't on the product team. one of them happens to be the chief product officer but to have that group decide what the roadmap is, where they're going to go, it's a very interesting structure. so i think this is more prevalent than most would like to let on and in their defense, product managers often do their damnedest to ensure the integrity of the product and the enablement of value for customers and users, and i think that's where opinions can continue to diverge, because it may not match the narrative of a leadership team and what they have envisioned for the product, if anything at all.
josh: 21:51
and, to be clear, you're not saying don't bring opinions and perspectives to the product management team. you're welcoming opinions, perspectives, ideas for direction. really, what you're coming down to is trust. trust this group of professionals who oftentimes have gone through some sort of training or education for specific product management philosophies, principles, frameworks, etc. trust these individuals to do the job that you hired them to do.
guest: 22:25
that's correct. i think it does come down to trust and i think it is about that empowerment and the accountability. i think that's the other thing that product managers are open to is having clear goals and definitions of success and defining those at a company level, a product level, a feature in capability level, and having the accountability when things may not go according to plan or is hoped. but you're right, that's exactly what we're saying. product managers want to ingest as many data points as possible, both qualitative and quantitative, before making a decision about the best path forward. and, to use that cliche saying, if you want to go fast, go alone. if you want to go far, go together. that's really what product managers are trying to achieve and, while not everyone is going to agree on all of the decisions, it really is about unifying around that definition of value and being open about what that definition is.
josh: 23:35
that term, accountability, i think, is incredibly important. i think that's part of what makes great companies great and poor companies well, poor is that idea of accountability. are the right people being held accountable? are the right teams being held accountable? and i don't mean that from a big brother perspective, i mean it from a are we accomplishing the goal that we need to accomplish? are the team members, who are focused on different elements of that goal, contributing in the way that we need? how can we measure that and how can we justifiably change the course as needed, whatever that may be? so, when you're thinking about accountability and product management, what are some examples of accountability? is it really just about did this particular feature get released on time? is it customer satisfaction? what are your thoughts about product management and accountability?
guest: 24:32
there are entire books written on metrics, kpis, okrs as it relates to product management, so i'm not going to try and regurgitate some of those points. i think for me, the accountability comes down to ensuring there's clear goals for the things that we invest in and ship and that we're honest when we look at the performance of those things, whether it relates to market impact or customer value or uptime or availability, whatever you choose as your set of markers and your measurement, defining that beforehand, being honest about whether or not you've achieved that and, if not, iterating in a way that allows you to get closer to it, or deciding to take a different path. but i find all too often that it's made up on the fly, especially if we're not adhering to a roadmap.
josh: 25:36
i like that idea of defining beforehand, whether that's in the terms of how you're going to measure a successful feature launch or product launch, or even just in general defining a course for the product management team. this is what we're going to hold ourselves accountable for and we're going to speak to a company all hands, et cetera. just something to make it clear. this is our focus and our priority. now, in other philosophies it's very much like well, make sure you're not working just for the sole benefit of those numbers and accountability metrics. at the end of the day, you have to do what you started out describing, which is bringing value to the world through the form of the product, and is that actually happening? but i think that's a great call out of let's make sure everyone's on the same page beforehand. here's how we're going to grade our performance so that we can understand are we meeting the mark? if we need to improve, how should we improve? based off where are those areas that need to be improved? and you can only do that when you bring some specificity with. this is how we want to be, this is what we want to live up to. so i think that's a great call out. now it's clear from your experience and some of the things that you're sharing that you've been through a lot and that you've seen a lot in product management. i'm wondering if you have a story of disaster that you'd like to share with us.
guest: 27:02
one does come to mind. it was at a place that was going through multiple renaissance, multiple changes, and if we could take a step back and think about that and remove ourselves from that equation. if the company and the team are going through multiple renaissance and changes, imagine how chaotic that is for everyone involved, especially for the customers for whom you're trying to deliver value. one thing i want to underscore there is that kind of change can't be done in a vacuum. those effects ripple out everywhere in visible and invisible ways. additionally, as that team was going through those changes, i noticed that there was a lacking investment in product and quality due to some prior decisions that were made, and there were a handful of us, a handful of individuals, that saw a critical turning point as an entire organization where we decided enough was enough. we decided to refocus and we decided to build impactful and, frankly, overdue features and capabilities and, as a result of that focus, we started to realize momentum and we started to really reengage with customers and to start to add value, and we were on the track to reinvigorating and regaining product market fit that perhaps had eluded us more than we had wanted to admit.
josh: 28:51
i think that's something you called out the constant changing or the chaos, this idea of multiple renaissance. this is a very common experience in saas startups. startups are constantly quote-unquote, pivoting, and sometimes that is due to you've realized something and you have to change direction, and sometimes it's fear-based we're not going to make it to the next round of funding, for example, we're not going to acquire enough customers or users within a certain timeframe and we're going to run out of money and we're not going to be a company anyway. we're not going to be a company anymore. so i think this is a very common scenario. so you started out in that experience. it sounds like a team came together and really found a couple of core things to work on and to make sure to deliver. you talked about this idea of regaining product market fit, which, to me, clues me in that there maybe was some faltering that happened there, some deviation from that initial product fit or that market fit. i'm curious in this chaotic experience, what was your day-to-day like?
guest: 30:04
yeah, in the chaotic experience, the day-to-day was mostly fired, fighting and mostly responding to the next loudest or the next most important request, while also shielding individual contributors in the organization as much as possible and providing consistency and a vision and a direction for those folks. so managing that change through leadership is something that is definitely stressful and i would give it to any of the leaders that i worked with over that period of time doing the best they could to navigate that change and provide that consistency on a daily basis as best they could. but in the end, as i mentioned, change doesn't happen in a vacuum and folks will feel that uncertainty. once we were able to focus if i can shift gears once we were able to focus, we started getting into a regular rhythm and we were able to have the engineering and design and product and marketing teams and other teams working with us and collaborating and we were able to get multiple projects and multiple features and capabilities along the varying stages of the software development lifecycle. we were interviewing customers, we were performing ongoing validation of both the direction and the focus of what we were working on, and that collaboration i think was really key to, as we talked about earlier, ensuring that everyone's opinions were surfaced and heard to continually gut checking if we were on the path, adding value or not, so that when we did ship the work it was meaningful work, there was a spirit of we can make it in the air and there was that spirit of excitement again, that energy. so it was really a wonderful change, i think, to be able to refocus when we did and we were able to see some benefits. that's great.
josh: 32:32
it sounds like. i'm curious about what you're going to say next, because at this point in time it sounds like you had a pretty good thing going. like you said, you started out there was a little bit of chaos and confusion, teamwork together, lots of collaboration, i'm sure, with that, lots of conversations coming together and then really getting on the right track, but that doesn't sound like a disaster at all.
guest: 33:00
well, there's more to the story. while we were energetic and reinvigorated, i think one of the missing pieces was a repeatable go-to-market motion, and for those who have been in b2b saas, many can attest to how difficult it may be to land and expand accounts, and i think the board probably wanted change. they wanted someone to achieve that growth. that alluded the company for the prior years, where they saw competitors and other saas companies grow and they wanted to see them grow at a much faster rate. surely they wanted to hire someone who could establish that repeatable go-to-market motion, who had a history or a track record of growing a company, growing a team and building a wonderful product. i think, unfortunately, the leadership that was hired didn't have the level of familiarity with the market or even the type of product that we had to really be able to come in and hit the ground running. i think, to be fair, there are a lot of those who are part of this journey that may believe that the new leadership team was not as informed when they accepted the job. there was, and may continue to be, a large amount of tech debt and they may not have known that the go-to-market team was not firing as consistently as one might hope so. again, going back to assuming positive intent and assuming that folks were trying to do the right thing. everyone who joined, i think, was trying to come in and do what they knew how to do best. i think, with that lack of familiarity in the market, the customers and the product and competitors in the space, it was just maybe not getting the traction that we had hoped.
josh: 35:16
i think that's a great thing that you called out, which is things can be going right with the product, but on the market side, the go-to-market side, there could still be an issue. ideally, you would think that, well, if we build the right product, the right people are going to find it and use it kind of field of dream style, kevin costner. if you build it, they will come, type thing. and that's not the case. as ideal as that would be, that idea of product, market fit it's product and market fit the products could fit the needs, wants, desires, problems, pain points, et cetera, but the market might not be in a position to buy a product like that. now, people are always going to argue. well, if you demonstrate the value, if you prove the value, yes, you can find compelling ways to talk about the product and show people that it can bring them value. but in you know, you think about current times right now where, like especially, tech startups, saas startups, where layoffs are happening, you know people's positions are being eliminated, there's a focus on reducing headcount. that's all happening in the market and that's separate from the product, right? so i think what i love about what you called out is this idea that you know, it's not just the product. there are elements of the market, some of which are in your team's control, like developing the right go-to-market strategy. some of it is completely outside of the control and i think that comes up a lot this idea of timing and luck being a critical factor to product market fit. regardless, focusing on things that can be controlled, there was a decision made. you know we need to bring in people who are able to build what we're looking to build, and that's where we're at in the story. i think that makes sense and i can certainly appreciate your focus on assuming positive intent. yeah, sounds like from what you said. not all information was shared up front, which ultimately makes it more difficult to be a leader when you're working with limited or misinformation.
guest: 37:29
yeah, i think those are great points and one thing that comes to mind is something i heard in another podcast, which speaks to market and timing and the cost for customers and the importance of how much they may want to do something to actually implement software and whether or not they view your product as medicine, a vitamin or candy. is it essential, is it ideal or is this superfluous? and i didn't come up with that framework. i had heard it in another podcast. but i think, as you mentioned, it can solve the problems, it can add the value and it can be on a path to delivering more value, but if the other pieces, like you said, are not there, it really can be challenging.
josh: 38:26
as a side note, this is why product marketing and product management work so closely together. one focus in specializing on the market and one focus in specializing on the product. the two together quite the powerhouse. in fact, some companies are combining the role. apple, for example. their product marketing managers are product managers who do the product marketing, and from what i understand i think i saw an article about this airbnb is taking a similar approach, where the product marketing managers and the product managers are becoming just one role, because it's expected that if you're going to be truly successful in this position, you have to have these two distinct perspectives and disciplines coming together, working together, and so they're trying to create an all-powerful synthesizer of information.
guest: 39:17
apple is doing something right, so there has to be something said for what they're trying to do.
josh: 39:21
absolutely so there's been a change. what happened next?
guest: 39:25
i think what happened next was interesting and not all too uncommon. i think it's not uncommon to see a leadership team start to turn over when different leaders are brought in, whether that's on their own accord or whether that's for other reasons, but the leadership team as a whole started to turn over and new individuals, both at the leadership and individual level, were brought in that were part of the circle of the individuals that had come before them. interestingly enough, they were the folks who joined later had the privilege and the opportunity to judge those who came before them and to form the opinion that previous teams didn't know what they were doing. but we do and we know best. and i think, as a result of having individuals that formed that opinion, as well as having a new leadership team that doesn't have history with the existing members of who's left, all of a sudden you have an environment where individuals may no longer feel safe talking about anything for fear that it gets reported till leadership, and suddenly you're impacted for not adhering to party policies, and i think what ultimately happened is the culture of the company was obliterated and the company and the team entered a state of cultural flux.
josh: 41:06
this is a tough scenario because this idea of maybe the previous people working there didn't know how to make it work and to some degree that idea is reinforced by the fact that a new team of leaders needed to come in. and so to some degree, i can see where this perspective of out with the old, in with the new, because the old wasn't working, and then the impact it had on the culture. i imagine what you're referring to is the people who were still there that were part of the quote unquote old regime. they would maybe pick up on the fact that they were part of this, and so maybe the attitude is that they don't know what they're doing and, as a result, they're less proactive in bringing up ideas or sharing feedback, maybe a little bit more cautious, because they've essentially been put on notice that look, you didn't know what you were doing, we do, so get in line.
guest: 42:22
that's correct. and going back to something we talked about previously, there's no shortcut to building trust and if you come in with an opinion that individuals who are part of the team don't know what they're doing or didn't know what they were doing, and that the incoming regime knows better, you can't build trust in an environment like that. regardless of how many times there are informal events to try and build trust, you can't say one thing and exhibit another. it's incongruent and i think that's ultimately what contributed to the company culture ending in the state of disarray and flux that it ended in.
josh: 43:13
i can imagine that that makes an impact to culture. what happened as a result of that?
guest: 43:18
with the company culture and the disarray that it was in the product team and the product are not insulated from that we started to feel that same level of uncertainty, and other teams rightfully so started feeling that level of uncertainty. not only was the company culture in flux, but the opinions of leadership on what the product should be or what the product should focus on was also being redefined by this new set of leaders and individuals that joined the company. that manifested in our customer facing teams soliciting lists of enhancement requests upwards of 1500 for just a couple of customers. and customers were told we want you to shape our roadmap, only to have the roadmap dictated and changed weekly by the executive team in a way that would continue to satisfy all of the obligations that we had verbally committed to. it was a red flag for us on the product team when we started having different roadmaps for different customers. that is not a sign of having a unified understanding of the product or having an understanding of the product market fit or an understanding of what adds value in a way that will help the company. as i mentioned, the leadership team, i think, in trying to display value to customers in their own way, began promising those feature, enhancements and other deliverables, and this was, as i mentioned, at the expense of the roadmap and, as a result, the product and the quality once again began to languish, just as it had in the prior changes and renaissance the company had endured, and this is nothing to say of the drastic off-shoring and cost-cutting efforts that impacted our ability to execute on any of the promises. but all of that for those who are familiar with b2b saas companies, all of that happens behind the scenes. that's all dirty laundry, family internal stuff that doesn't get discussed, but often that is what adds an incredible amount of stress to the system. that impacts not just the product but also all of the other teams.
josh: 46:02
that's a tough scenario to start out with, like you talked about, because there was this beginnings of disarray that led to people trying to do the best they could with what they were working with, but that lack of cohesion, that lack of being united, led to maybe some stepping on toes for example, amassing list of customer requests, which it sounded a bit like with the way that you're referring to it, that it became customer demands almost this idea of, in order to acquiesce customers, we're going to go to them and tell them that they're shaping their roadmap, which in principle, sounds like a pretty good idea to say to a customer we want you to help shape our roadmap. but that goes against some of the information you shared earlier, where this needs to be treated as a perspective, as a data point that is then synthesized along with a slew of many other different data points and considerations, and i think that that's an important call out. there's nothing wrong to say we want our customers to shape the roadmap, but there is something wrong with we want our roadmap to be customer defined, and that's what i'm picking up with the scenario that you're in or that you were describing right now.
guest: 47:21
yeah, that's absolutely correct, and because of that direction, suffered vision mission goals. all of that changed daily as various teams, including the leadership team, had to say whatever they thought customers, employees, wanted to hear. because, like, don't forget to include ai, even if we don't do it, things that we wanted to portray and it was almost a fake it till you make it. or, if we hold out long enough, we'll be able to deliver enough of this so that we will not have been making it up. but that's a very difficult place to be in and i think it culminated. all of this culminated in blowing up our product market fit. the product in any market fit was abandoned and the company not just the product team, but the company had ultimately become ticket takers in hope of an outcome, in hope of something in the future worthwhile. because when you say yes to everyone, you really destroy the momentum and the focus and the product integrity and in the end, no one is really getting what they want from a customer perspective, from a value perspective, even from an employee perspective, and i think what really hurt is this had an impact on people doing real work, and i'm not just talking about the generic term customers. when we say customers. there are individuals trying to use the software to complete tasks that they've been assigned. in the end, nearly all the customers could smell the desperation in the air and they leveraged that to request the things we asked them to tell us and request, and they grew increasingly frustrated with our inability to deliver on those promises and in the end, it was hard to face myself as well as others. the journey that i just talked about and the experience that i just outlined really highlighted some irreconcilable differences in values between myself and what the team ultimately became. the culture felt toxic and if you're working in a place where you don't feel safe raising a concern, raising your voice, having a dissenting opinion that's not a place most people want to work. yes, i could have phoned it in, but that's not who i am having, and then seemingly intentionally abandoning product market fit. i realized it was my time to leave. you can't fight city hall and you can't tell the board. they're wrong and in the end, it was the board and the leadership team and others who decided to change. it was necessary, again, for the right reasons. i think how those things transpired may not have been what we had originally intended.
josh: 50:33
so this chaos, this confusion that ultimately grew out of this lack of a united front ultimately impacted the actual product market fit of the company, and i like how you called out this idea of customers and really getting deeper. it's easy to think of the generic idea of a customer, but it's different to think of real people, people like yourself, who are using software because they have a job to do, that they get paid for, that they use to then help feed their family and provide for their loved ones. really, breaking it down to these real people who use our software had tasks that they had to do for their work. they needed to use our software to do that. we wanted to provide a great and valuable experience, but with the uniqueness of how different companies operate and different roles within those companies operate, that leads to a lot of conflicting demands for specific features and capabilities, and trying to take into consideration all of that coming together and then delivering on all of it. there's no way anyone can be successful in that type of conversation. that's just too much. that's too much when you think of the scale that software tends to have, depending on the type of software, of course and for you to come to this realization that it was difficult to essentially live with yourself. you seem like someone who cares a lot about integrity. it sounds like your integrity was raising some red flags to you.
guest: 52:20
that's correct. it felt almost as though i was that proverbial frog in water. that was cool at first, that it's starting to get hot and i came to a point where i realized the water is too hot. but it's amazing how long someone will put up with something in the hopes of things getting better or in the hopes that we're on the right track. but when you think about the first principles that lead you to your career or your company that you work for, or the things you work on and what you try to do to add value in the world, you have to be honest with yourself and understand where you're at and take the appropriate actions. you owe it to yourself.
josh: 53:16
you called out something that another guest called out, that idea of hope. she actually called it hopeium, that addictive holding out hope. i hope it's going to get better. i see the potential. i certainly experienced this myself. i found myself in a situation where i was really happy with a lot of things that i was doing, but there was something not really adding up. but i always had hope. i always hoped this year is the year or this is the change that we're making and this is what's going to do it. i always found a reason to hope, but really what i was doing was rationalizing the situation that i was in because i was scared. i was scared to make a decision. it sounds like you reached that same point too.
guest: 54:00
that's right. it's rationalization. that variable summarized.
josh: 54:06
so you left.
guest: 54:08
is that right? that's correct. i stayed long enough to ensure that there was continuity for the team that remained.
josh: 54:16
integrity.
guest: 54:17
one of the things that was very important to me is ensuring that, just because i may not have been a fit or i may not have believed in what the direction was, it was my responsibility to ensure that the team was set up as best possible to be successful. i think no matter if you're in product or another team marketing, sales, customer success, support whatever it may be you owe it to the team that you work with, as well as the broader company, to try and leave on as best as terms as possible. but i'd say since that day i've really been able to achieve some peace of mind and my personal sense of integrity and honesty has come back. i think taking the step to leave is hard financially, emotionally, the uncertainty not sure when folks will listen to this podcast, but the tech world is undergoing a lot of change right now, with layoffs and redefinition of roles and all sorts of things, so leaving is very difficult. and then i think the other thing that we touched on earlier briefly is related to the fact that there's a continued concern i have for retaliation because, although i know many others experience similar things, frankly it's taboo in tech to talk about this kind of stuff, even talking about this situation out loud makes me think there's an opportunity for getting blacklisted. in tech, and i think many others feel this way, we're not supposed to portray anything other than things are great, because that could be detrimental to the health of the company, the brand, whatever that may be.
josh: 56:22
and it's a shame that that is the feeling, because at the end of the day and you look at one of the go-to books for developing a company is good to great. why? i can't remember the name of the subtitle, but it's why companies succeed whereas other companies don't, and the answer to that is people. it's always people, and so there's power there in putting your people first. at least, that's what i believe. so it's a shame that the professionals in this industry who are responsible for making these products, that are making these companies the money that they need to operate and to continue to grow and to expand, have a concern. have a concern because now their livelihood could be affected if they share what they honestly went through. and it's one of the things that the disaster recovery podcast stands for is accountability, and the only way that we can promote a culture of accountability is by making sure people like yourself, myself, others in similar situations we refer to them as sassholes here on the disaster recovery podcast making sure that they know that they're not alone in these experiences that they've gone through, so that when they see a situation happening and it sounds familiar, they can do something about it. they can take a hard-learn lesson that one of our guests has shared and apply that to their own scenario and maybe affect the outcome. maybe not, but at the end of the day, at least there is peace of mind in knowing that you are not alone in this experience that you went through. i've talked to a lot of people who have expressed similar concerns that you have. i can't share this because i'm afraid of retaliation. you know you go on glassdoor. you see a lot of negative reviews for a company. even then people are hesitant to actually post that on glassdoor because you never know what sort of data is being collected and shared, with whom, at what cost, et cetera. so there's very much a fear of if i say something i will then bear consequences, which is unfortunate because it's not like they're, in this case, spreading libel. they're spreading their experience, which is two totally different things.
guest: 58:42
that's right. this is my opinion and my experience, and i know individuals at companies i've left in the past that are having a different experience, and i'm genuinely loving that they're having a different experience. that's what i would want them to have.
josh: 59:06
so, when you think about that entire experience, what were your top takeaways? what were the top lessons that you learned?
guest: 59:16
there's definitely a handful of them thinking back to that primary message of product market fit. if you're able to find product market fit, you'll know it. hold on to it with both hands and don't let go. defend it as best you can. the rest will fall into place a lot easier. so i think that's the first thing that comes to mind. i think the second thing and this was imparted on me prior mentor and that is to build yourself some freedom, to build yourself a ripcord and to not be afraid to use it. you build it to use it, and what i mean by that is to build yourself the freedom so that you aren't afraid to leave a culture that you don't agree with or people that may be negatively impacting you in certain ways. gaslighting is a real thing. office politics it's a real thing. nepotism it's a real thing. if you don't have the flexibility or that ripcord to pull, you will feel trapped and it can manifest in really unfortunate ways. so i think that's the second thing. i think the third thing that comes to mind is to recognize that if a new leader or leadership team is brought in, the writing is on the wall. they're there to enact change and in those situations be quick to act and decide if you should exit or stay and think through the reasons why. don't fall into the trap that i've fallen into and rationalize. take an honest assessment of your situation, your personal situation, and act. i think the next thing that comes to mind is you need to know when missing business momentum is customer management, support, leadership, sales, marketing, the industry, the product timing or something else. you should do your best to try and interpret the signals that you see, to determine why something may not be working correctly, and you owe it to yourself and to your colleagues to have the courage to call things what they are, not in a gossipy way, in a public way, so that everyone can benefit. the trade-off there is recognizing the culture you're in and doing so if you feel safe because of the potential negative impacts and retaliation. i think the next thing is when you're working with people, beware of people who aim to please at the cost of others. they are even quicker to sacrifice you when things don't go according to plan. i think the next one would be beware of those who have to say they are something, for by saying they are something, they're demonstrating that they are the opposite, and if i have to advertise that i'm a proficient product manager, and if i have to advertise and convince others that i have a set of traits or capabilities, or to trust me, you're often demonstrating the exact opposite. and then i think the last one may seem a little cliche but warrants restating, and that is you really need to trust your gut and listen to yourself. you're not crazy. the things that you experience are real. they may be your own experiences, but that doesn't make them any less valid. having an experience doesn't mean that you can turn into a jerk or that you can sabotage things or gossip or do things that are detrimental to the success of the team. having an experience means that you need to recognize it for what it is, understand what it means to you, and to recognize that having that experience means that you're responsible for taking an action based on that experience. so trust your gut, listen to yourself.
josh: 1:03:57
it sounds like this was quite the learning experience for you. just to recap some of the things you shared, which seem to fall into categories that are applicable both to product managers as well as just general employees at an organization that idea of your company, if your startup has found product market fit, hold on to it. understand why. what really made it resonate with this particular market? who are they? what about the product do they like? why this product over other products? dig into it, understand it and then build a scope around it so that you can stay focused. i love that you called out this idea of having i think you called it a ripcord being able to pull the shoot right, the ripcord for the parachute, be able to get out, set yourself up in such a way and this is not something everyone is able to do, i understand that. but if you can build your network, build your network so that you can find out about opportunities that can come up that you could be a potential fit for, or save some money, if you're able to, so that you have a bit of a cushion, so that the threat of you losing your job is lessened to some degree, so that you have that peace of mind so that you can make that tough decision and get out. otherwise, you risk continually rationalizing why you should stay, and you can rationalize through that hopeium. sometimes you don't even see that the water is actually starting to boil around you. i think that was a very practical call out that you made that when there's new leadership, there's going to be change. now there's no clear way to understand what exact change there's going to be, but you need to know that there's going to be change and that change could impact you and you have to make a decision. do you want to be a part of this change or not? and it's okay if the answer is yes to either one of those questions. that's totally okay. just be an active participant in that conversation. and you know one of the other things that you called out that really kind of stood out to me. it's just that idea of trusting yourself you know when something's not right or not right to you and giving yourself that credit so that you can make the decisions that are going to be best for you. because, rest assured, the company is making the decisions that's best for it. so, at the end of the day, you do have to make sure that you are making the decisions that are best for you as the individual. so i think those were some great lessons. i know i didn't hit all of them, but those are some of the ones that really stood out to me. i appreciate you sharing them.
guest: 1:06:46
yeah, thanks for the opportunity to summarize my lessons and my experience.
josh: 1:06:51
well, look, i really appreciate you joining, sharing your perspective on product management, your philosophy. i really enjoyed the conversation about what people think about product management and how they typically get that wrong within the world of sas. the story certainly resonates with me. this is something with the community of people who are addicted to startups that i've been able to connect with. it is a very common scenario to describe the chaos, the firefighting, the constant pivoting, and so i think it's very interesting to hear a story about what happens when people try to bring order to the chaos and the impact of those decisions. and ultimately, like we highlighted in your story, it's not always sunshine and rainbows. sometimes there's some really tough times and tough experiences. so i really appreciate your vulnerability and your candidness in sharing all of it.
guest: 1:07:49
happy to share it in the hopes that it helps someone else.
josh: 1:07:52
but with that, i appreciate your time. i hope you enjoyed this episode as much as i did, and i had a lot of takeaways from this conversation with our guests. i mean, what a great perspective that he shared on the definition of product management, and i'm quoting him now. i went back and listened to the episode so i could get this just right. product management is about directing the limited resources we have in life in a way that adds value to the world by building meaningful products. talk about a mission, talk about something more important than the individual directing limited resources that's a top topic right now a way that adds value to the world. i think that that's such an important thing to keep in mind with anything that you are doing is the impact it can have, not just within your sphere of influence, but in the greater scheme of things. i'm also really glad we talked about this idea of solving problems and pain points versus bringing true value to customers. this is a perspective i hadn't considered before, and it's kind of like that quote that's attributed to henry ford about how, if he asked what people wanted, it would have been a faster horse, but instead he built the car right. it's that idea of really understanding what needs to be solved not necessarily the way people think it should be solved at that time and then goes back to some of the things that our guest was sharing about trusting specific professionals who have undergone such training and certification programs, who focus on delivering just that understanding what could be the ideal solution to a situation. i also love that we talked about the idea of product market fit being fleeting, because it totally is. it's not static, it's ever changing, and that's one of the things i love about product marketing. i think when product marketing is done well, it's really about shepherding the herd toward product market fit, the herd being the company and, in some cases, the customers and the market as well. now, how many of you could relate to that slow burn story shared by our guest, that idea of sticking around hoping it will get better because you can see the potential but not realizing that you're kind of like the frog in the pot of water that slowly begins to boil and by the time you realize your mistake aka not getting out you get burned. i think the story also crystallized this idea in finding product market fit, that you can't be everything to everyone and without a clear understanding of what value your company brings for whom, how, why, why that matters. without that, you could find yourself deceiving customers and maybe even yourself. and when we're talking about customers, we're not talking about this abstract idea of a customer. we're talking about real people who rely on the software your company sells in order to do their job. that's a big responsibility. you can't ever overlook that, because what if that was you? now, before you go, take a second and subscribe to the show. let us know how much these stories resonate with you, by leaving us a rating and a review in apple podcast or spotify or really any podcast player of your choice. also, be sure to share these lessons with a co-worker or even a boss who is going through it with you. who knows, maybe your story of disaster could be next.
