This weeks episode we’re talking to Kenny Goldstein. Kenny is a consumer-centric Product Management Leader with over 20 years of experience building products, platforms, and teams within start-ups and high-growth organizations. Most recently, Kenny has focused on Product Management Consulting, using his array of business experience and strategy skills to help companies bring products to market, stand up new teams, and support new strategic investments.

Kenny’s Top 5 Leadership Tips:

Below is a summary of the Top 5 Leadership tips shared during the interview this week. Take a listen to the episode to learn more about the thoughts behind these tips –

  1. Understanding Success
  2. Bringing Teams Together
  3. Expect The Unexpected
  4. Have An Effective Methodology
  5. Proper Execution

We hope you enjoy the episode. You can find even more Full Stack Leader episodes here:


Show Transcript

Ryan: Hello everyone. And welcome to this week’s episode of the full stack leader this week. We’re excited to have Kenny Goldstein with us. He’s the vice president of product management at product first, Kenny, it’s great to have you here. Welcome. 

Kenny: Thanks Ryan. Great to be here. 

Ryan: Awesome. Why don’t you tell our audience a little bit about how you got here?

What were some of the steps in your career that led you to this moment? 

Kenny: Sure you got it. Yeah. So I’ve been working in product development for a little over 20 years. There’s actually two parts of my career. I originally actually began my career in design, working both in house creative and startups doing everything from branding and catalogs and packaging, and then had an opportunity early on to help some companies bring their first websites online and that was a foray into digital marketing where I really haven’t looked back since. And so yeah, this first part of my career was really focused on application development, different types of digital marketing and advertising and working alongside engineering and marketing.

To support new features as well as bringing different products to market. And, in this particular time I just, I always had an affinity for strategy. And so whether that was through creative briefs or just simply asking the question. No, how is this thing that we’re building going to meet needs?

I was always interested in that and then making a measurable impact which led me over time to to start my own design company and then eventually merge with another firm and help lead their interactive services working with companies like BMW and Hilton. Disney and so forth.

But also not only to work on. The execution and the creative aspect of things, but also on business development and even partnering with sales and crafting statements of work and then also, recruiting building teams and building strategic partnerships to help support the things that we’re selling.

And, yeah, it was just, a really, paramount part of. I think over time I kinda realized that, some of the work that I was doing, whether it was as part of a delivery team in a startup or in this agency kind of model some of the, the strategy was already being determined before.

Before I was getting my hands on it and I had this desire to get into the problem and the opportunity earlier on and deeper, and thus found myself looking towards product management as a means to do so. and that. Really to the second part of my career, we’re up spent uh, 15 years now working in this space across a number of different types of companies and sizes of companies and different sectors as well.

And predominantly I’ve spent my time in consumer products, but that’s inclusive of both B to C as well as B2B to C. And yeah, I got my start at a company called shop Zilla who at the time. Was competing with Amazon and Google products. Which weren’t what they are today.

But uh, I joined their consumer product team and had an opportunity to work a lot across a lot of the types of products and yeah, 15 years on like I said, I’ve touched a lot of different sectors and. And I’ve had the opportunity to lead teams and strategies and so forth, across a lot of different types of products.

Ryan: That’s amazing. And I know that coming in at the early stages of the entire IOT game, like you get to see a lot of the evolution throughout the course of time, and it actually really informs where you end up as a leader. And today’s market. I remember the shop seller by the way.

Those are those great applications back in the day. Were there any other kinds of pivotal places that you worked during that period? 

Kenny: Absolutely. There’s been some sort of big learning at each organization along the way. But I think the shop Zillow was pivotal in many different ways, both in terms of the transition to product management, but also in the way in which that organization was run.

It was very progressive doing lots of AB testing, very much an empowered product management organization, having the opportunity to be involved. Early stage and whether or not we should do this thing, what it might look like, how to fund it and so forth. But then also, you know how to build against it.

And that’s something that I’ve taken with me and had an opportunity to do some interesting things where I spent. For five years or so of my career in automotive. Right. And it’s not traditionally considered e-commerce, but there’s a lot of similarities there. And you’re essentially trying to help somebody, make a very complex transaction.

And so a lot of the same types of things come into play, right? Like from. Early stage, user acquisition, how do you help them find what they’re looking for? And then how do you help them and triangulate across the things that matter? And Edmonds had a ton of interesting opportunities there, both in terms of being part of internal accelerators to innovate in a space that really hadn’t had a ton of innovation as well as to help really solve this transaction.

It was one that you might do a lot of research online, but at the end of the day, it’s still taking place, down at a dealership lot. So again, that whole connectivity of looking at the problem and the opportunity to holistically was also really powerful in my career.

So I would have liked that one as well. 

Ryan: Yeah. And I want to say, I want to say as well, Edmonds is one of the really great tech companies out of Southern California over the group of years that Tech’s been a player here. They’ve done some really innovative things and I know the time period you were generally there, you guys were doing some really special stuff, so that’s great.

Kenny: Absolutely. Yeah. And that was a lot of fun as well. So my role at Edmonds, it was a role focused on mobile. And so it was just in that period. Yep. Yep. And it was at a time when, we had this really compelling research that had been done by a third party that car shoppers had likened, buying an automobile to having a tooth pulled.

So it was a really painful experience. And we really dug into what was going on there. A lot of it really had to do with not so much like finding the car or the space that Edmunds was traditionally playing in. Find the car, find the vehicle that has the space or the seating that I’m looking for.

But it was really about the part of taking that information. Then actually making the purchase at the end of the day. If you can’t really. Facilitate that end to end conversion. You’re not really providing the value that the end-user’s looking for. And so the real problem statement was down at the dealership lot when all this information that the consumer had was somewhat lost.

As the dealer who had been through this thousands of times, just knew more about it than the consumer and the dynamics would change. And so having this mobile device in your pocket really provided a really unique opportunity to solve that problem and provide value to the dealerships at the same time.

Ryan: Yeah. It really is such a unique moment in time. Right around that same time period in the early 2000’s where you could walk into a place like that and actually have some of them, some of that power at your fingertips and actually know what you’re looking for. Be able to negotiate a little bit.

Like it’s very, 

Kenny: very powerful. Absolutely. Absolutely. So, yeah, that was a lot of fun. And then, um, I maintained a focus in automotive but broadened my focus in terms of channels. I kind of recognize that as much as mobile was tons of fun it wasn’t this linear experience where a consumer just starts on a device and stays on that device in particular for a more complex transaction, like buying a car.

And so the ability to sort of leverage all channels was important. And so my role at Kelley blue book was about helping again to look across all channels, but also all different vehicle types, right?

And the life cycle of a vehicle from someone who’s looking for a new car to someone who’s looking for a used vehicle to somebody who is at the very initial stages of just trying to understand what sort of equity they have in their current vehicle to make a decision on which direction they should actually go.

And so in that scenario, it was a really interesting experience. At Kelley blue book as well, both in terms of, replatform, helping to transform their product organization to a more empowered team, take some of the learnings from the way in which shop Zillow kind of ran things as well as some training from Marty Cagan silicon valley product group and really helping to stand up this new kind of, durable, empowered teen format, and then to leverage that type of collaboration to, re-imagine what should this car shopping experience actually look like?

Ryan: Yeah, that sounds amazing. And we have to actually be able to find it in the moment, bring it back to where we needed at that time, and then create a bigger picture.

Ultimately, it seems that in order to make that final decision, 

Kenny: Absolutely. And one of the interesting things in automotive is that it may not be overt to the consumer, but, We’re at shop Zilla at the end of the day or even Amazon for that matter. You, your marketplace, you are driven by your ability to how’s, in, in the e-commerce world, it’s millions and millions of skews. And. Auto space, millions of skews. And you’re dealing with advertising as being a primary input to the way the channel, trying to get eyeballs on vehicles and that in some cases can be. Contrary to what you’re actually trying to achieve from solving consumer problems, where you want to get them from, a, to B and probably the quickest way, but at the same time, that may be a bit contrary to some of the success criteria from an advertiser standpoint, right. creating impressions. And so the interesting work there is right. Absolutely advertising is an extremely compelling and valuable part of the auto shopping space. But what are the means to actually bring that into a more native.


Helpful means to solve that consumer problem that we talked about earlier on.

And so when I first transitioned into product management at shop Zilla, I became my role as the special projects guy.

And so they had all these investments or product managers assigned to each particular product feature, but they also resolved all this other. Space of should we, could we be doing X? And so I got the opportunity to be the guy who would look outside the organization of what are some things that are happening in the market, how well suited are we to potentially go after that?

What would that look like? What kind of an investment would that be? What would a model look like? How would we resource that and then building the thing and then coming back and reporting on that, all the way up to executive leadership and that full stack like ownership of looking at market and then building, and then reporting is something that has absolutely had probably the biggest impact on my entire career, because it’s really this Really white space oriented problem solving that I even utilize in terms of what it looks like to build a team or what it looks like to look at a particular investment.

Yeah, you 

Ryan: Can, you can see like the traditional measurements and like a high value purchase like this, or even something with that kind of cost of acquisition as well if it’s pretty big. And so like thinking about it from a native standpoint, I really like that.

And this is kind of what the internet and mobile allowed us to do is to shift our mindset on that and think about, oh, these are actually. Things that we’re going to learn from, and they’re also advertising. 

Kenny: Absolutely. And actually you hit the nail on the head as well. So during this whole time mobile was just taking more and more share.

And of course, with more, share more of mobile, less real estate, you have, it just becomes untenable to really maintain your historic KPIs. And so you really have to rethink. And so, you know, I would say. That type of thing even occurred not in advertising, but in a different way. And in commerce at shop Zilla where there’s been this, you know, in each company I’ve actually been out, there’s been this need to sort of rethink, the current state of things and then assess, how well.

Is that meeting our customer’s needs, our consumer’s needs? And what are the, what is the IP or what are the capabilities that we are really like well-positioned for to execute on? 

Ryan: Yeah. And I think you’re bringing up an interesting point of product leadership.

In today’s world where you really have to think about the purpose of what the application or in the case of a commerce environment with commerce environments trying to do so that you don’t pigeonhole everything into one methodology of conversion or one specific type of addicts, but expectation.

So I think that these On a leadership level of guiding the teams who are helping you build the products and thinking about the engagement that they’re really coming at it from an audience centric point of view. 

Kenny: Yeah, that is a fantastic point. It’s a fantastic point on so many levels, right?

It’s a really, it’s a really good point from the standpoint of metrics, right? There’s the metrics that the organization is using to measure success. There’s the metrics that are a much deeper level that the product manager or management team is using to monitor. The proxies for what might turn out.

And then of course, so are we measuring the right things? And asking those questions. Yeah it’s also about Thinking about the investments, whether they’re front and center now or new ones that might need to become front and center to actually then move those metrics. Yep. 

Ryan: Amazing. So, so, After you kind of got out of the automotive space, did you say you looked like you shifted into something different?

Kenny: I did. So I had a lot of fun. With, creating new experiences and so forth. And I also had a lot of fun. You know, Spending time thinking about how we can make this organization very effective and efficient at building products and bringing them to market and so forth.

And I built some opinions along the way, of course, as well. An accurate background, which is a company that does background screening For companies like Amazon, Starbucks, and Disney , so I got some big customers there and they happened to be at a point in time where they were looking at building a brand new product management team.

And I had an opportunity. It’s a kind of play, a larger leadership role there in terms of helping to stand up a team from scratch or to transform a team that was previously in place. And then also to do a bunch of product transformation. 

Ryan: Those are really big moments too.

There, they can really test you in your career to see, okay. I really think of this all the way through from like those ground up blocks. And instead of just jumping into something that’s already in motion where you’re just making small adjustments. 

Kenny: Absolutely. Absolutely. And I would say the concept.

Yeah. Doing the recruiting aspect of it, and even before you’re doing the recruiting, doing the aspect of what should this team actually look like? What might be the pillars that we need to orient ourselves around? What type of budget do we need to actually support these types of roles and what type of.

The investment would be, think about making from, from these new resources and so forth, and then going out and doing the recruiting and then building the culture and the team. And that was all just like a ton of fun as well as working for customers. Like Amazon, for example, where they’re so progressive and out in front of what other companies are looking for there was alongside this need to really.

Again, think very creatively around what are the types of things that, that we’re doing today, but what are the types of things that we need to be doing tomorrow, 

Ryan: And you have to have some kind of innovative thinkers. 

How did you speak of leadership and speaking of bringing product teams together from the ground up and thinking about that, how did you work with some of the other leaders in the organization and make decisions because product managers are so pivotal in driving the actual kind of heart and soul of an application.

What were some of the ways in which you worked with those? Like the CEOs and the CTOs and people like that. 

Kenny: Absolutely. Yeah. So in this particular role I had a partner who really focused on more of the backend of the platform. And the two of us, partnered, we actually came on around the same time when we partnered in, what should this team look like?

And we. Collaborated deeply across the organization, both sideways with peers and operations and customer support and sales and so forth, as well as, up to the executive leadership team in terms of, building the case for where we are today and where we think we need to go?

And some of that. Opinions that we formed, through, through our own analysis. And some of the most powerful information came directly from partnerships through the account management team, for example, where you’re hearing directly from the account managers and their customers, what are the problems they’re really dealing with and where do they want to go?


Ryan: Yup. And then finding the right people that can round out that experienced team, right? Think about it. 

Kenny: Absolutely. 

Ryan: Amazing. So where from there, and as we can see, you’ve had a very long and varied career, which is amazing. 

Kenny: Yeah. And it’s been interesting. So I was really enjoying the experience from an accurate background.

I did find myself in a place where I was for the first time questioning my own. I’m Interested in the purpose of the product, historically, and I’d always worked on these products that I could use and I can really dog food it. And I could really like it. I found that when I did that, my ability to really thrive and really drive results was even deeper.

And I had an opportunity to come my way to, again, take on a larger role in a space that I actually felt very connected with, which happened to be a mortgage or FinTech at Home Depot, and again to build a team but to work on a scale that I really hadn’t worked on yet. So loan Depot is one of the five largest mortgage companies in the country.

Thousands of loans originated, each month or there they’re now a public company. And yeah, I love the concept of, big believer in, in particular, in financial technology, this idea of leveraging data points that may have not been leveraged before to help make that experience.

As frictionless as possible. Again, you can hear some similarities to what I’m talking about. Although it may not be an overt connection to some of the things I was working on. Even whether it be at shop Zilla or automotive, different sectors, but same or very similar kind of problem statements.

Yeah. Yeah. And it’s 

Ryan: Interesting, you’ve now covered traditional retail shopping or e-commerce shopping shop Cilla automotive experiences and now like mortgages and you can really look at the full landscape here, which is great. And it’s. 

Kenny: I would say there’s like this interesting connectivity behind the scenes as well. So even if you, if you look at a background screening, So to the end user the consumer. That is theirs, basically a long form of acquiring different information from the consumer and the easier that you make that, and the more accurate that you make, the shorter time span that the consumer or the candidate is able to complete their screening.

And thus, the employer has a better chance of actually closing on this candidate that they actually really want to hire. And the, and then of course there’s reduced costs there. If you even look back at Edmonds there’s the advertising model. We talked about Ms. Also, and even Kelly blue book, there’s also this lead model, right?

How do you connect the consumer with a dealership with the car they want to buy? Well, Guess what, there’s a form. How do you get a consumer from the top of the form to the bottom of the form and the most frictionless way. If you look at a mortgage, sorry. Got it. Oh, Annapolis. 

Ryan: Sorry. I’m just going to say it.

The loan application process is also. 

Kenny: That’s exactly. Kind of the point. So there’s yeah there’s that exact same experience. And then of course, how much can we automate this? How much do we already know if we get X information from the consumer and how do we enable it alongside this is where the enterprise software piece comes into play as well.

Where, if you’ve got recruiters at, in the employment screening, how are they facilitating the screening process behind the scenes, whether it’s ordering a new screen or, unblocking impediments along the way, and then in the mortgage space, right? How are the loan officers supporting these potential home buyers along the way as well.

So, There’s. Consumer-facing software, everything from the initial kind of lead acquisition down through the mortgage kind of origination down into the funding where there’s all kinds of different software components there that are both consumer facing as well as enterprise.

Ryan: Yeah, that’s amazing. Only when you’re able to see these different things across a landscape that you’ve been able to, you’ve been able to work in. Not a lot of people get that level of exposure. Can you start to see the commonalities, that kind of dot all of them? And there absolutely are on, and any level of products you’re going to work 

Kenny: on digitally.

Absolutely. And I think what I would say has been what’s been powerful for me. From a leadership standpoint is being able to connect some of those dots that may not be overt. So some of the industries, for example, I don’t know, maybe mortgage isn’t the most innovative sector and thus there may be practices that haven’t really, but that are already in other sectors that haven’t really been adopted yet.

So being able to identify those things and then bring, it’s not like you’re, you’re, it’s innovation, but a different type of innovation and you’re not bringing some brand new thing to market, but they’re safe. That’s in there. That’s what actually can end up really paying dividends and really helping to.

Build a momentum and trust within the product management organization, which by the way, isn’t that we haven’t really talked about. But, you know, it’s an interesting theme that is also alongside each of the roles. In each organization, they’re trying to figure out in many cases, especially when you’re coming into standup, something new, what is this team and how does it fit into our organization and where is the value derived?

And and it’s never, 

Ryan: It’s never the same company to company. Either everyone values product management a little bit differently, and even sees it falling into different categories. Sometimes it’s a tech part of the organization. Sometimes it’s a marketing part, sometimes it’s a stand on its own, probably, which is the most realistic cause it’s retention oriented, but like, the, it really is as you’re standing them up and creating an identity for it, it can slot to a lot of different places.

Kenny: Absolutely. Every company has its own individual DNA and personality, and some of which you’ll be able to transform. And some of it, you’re just fitting within. And yeah, so a lot of really important skills along the way, in terms of, being able to look at the different types of, the different sizes of the businesses, the different resources, the different teams within the organization, and then design, I don’t think believe there’s one.

Sort of, or product management organization, structure either, right? It’s what’s the best fit for this particular organization at this time? 

Ryan: What do you think is a generally good product structure that you’ve seen? I mean, you’ve worked across a variety of different companies, but when you’re thinking about laying down the foundations of a product team structure, what are some ideas?

Kenny: Yeah. I mean, The first thing that comes to mind for me that has, again, I think been consistent throughout is I’m always looking to align product teams towards using. As opposed to, for example, platforms. So I’ve definitely seen this somewhere. This is my career. 

Ryan: Yeah, no, I was going to say, I really relate to this as well.

It’s actually over my career to the same exact methodology and you end up in a lot of conversations with people because you’re right. It is often around platform or device type 

Kenny: And it. does bring up. I’m sure you’ve experienced this as well. It’s not black and white, right? Because depending on the technology that’s in play, you may or may not need individual resources to work against particular platforms. The questions can be asked about, whether or not these are, can be, hospitality be embedded, which would allow us to have holistic thinking or maybe not.

But I think there are interesting questions to dig into there. And I have just found that thematic, right? What I’ve seen as a negative is when you’re platform oriented, to the extent that you have a real map and want to build against various value themes, and you want them to be a consistent experience as users traverse different types of devices and so forth.

There you end up building things multiple times and not finding and of course there’s ways to abstract and componentize and take exact aspects like shopping cards out or checkout out and then build that. But you know, so it is definitely an interesting area, 

Ryan: or do you also end up having.

To align all of the product, people working across platforms with the same exact thought process, often people are skilled in different areas. So you can actually see them and they’re usually audience oriented, so you can see them take a little bit more kind of global ownership within a particular audience or product 

Kenny: type.

Couldn’t agree more. Absolutely. 

Ryan: And so that kind of leads you to where you’re at now, right? What kind are you up to, and it looks like you’re working on some of these themes, integrating them into some consulting and tell us a little bit about that. 

Kenny: Yeah. So, I mean, In between loan Depot and FinTech, I had an opportunity to join a company called Surfline.

I’ve been a lifelong surfer and that idea of dogfooding a product had never really been greater. And it’s so 

Ryan: It’s so pure. Yeah. 

Kenny: Yeah. And just. Very compelling product and engaging user base. And um, unfortunately there was an acquisition, early on and didn’t get a chance to really see that all the way through.

And that led me to really think deeply about, what do I want to be doing and what am I, where do I really thrive? And this opportunity though, it was short at Surfline was really the triangulation of everything that I had working on. Both in terms of building a team transforming the way a team works and is organized as well.

Re-imagining the product alongside and doing so in a, in something that I could really grasp onto it on a deep level. And so as that kind of came to an end I decided to embark on. My own consultancy and work with the types of companies that I find compelling.

And frankly, there’s a lot of different industries that I find compelling. And so it was a little bit difficult for me because this was also right at the time of the pandemic. And everyone was quarantine and we were still figuring that out and it was you know what I’m going to take advantage of this and see how this plays out and see if I can utilize some of the business experience that I’ve acquired along the way to apply that to my career and be choice focused on being intentional on the types of companies that I’m working with.

And so today I’m really focusing on two areas. As I engage with startups and product teams at different types of companies to augment resources and help bring value to market. And this includes strategy and roadmap, R and D down to product design requirements, gathering growth hacking, and product marketing. And this is a ton of fun cause they get to build and there’s a lot of creativity and understanding and solving different types of challenges. 

And then separately working in the private equity space to support different types of investment assessments and so forth, which has also been Uber compelling in a very different way, especially considering that.

One I think there was a private equity acquisition at every single company I’ve been at along the way. And if you don’t know that, I think. One in every 14 employees is now working at a company that’s owned by private equity. So there’s just a lot of that, out there.

And it’s very interesting to peel back the onion and understand a little bit more about it. How the investors are looking at some of these businesses independent from some of the consumer and customer focused I’ve brought out earlier. 

Ryan: Yeah. And how it is a tighter group of investors, like a private equity fund versus a more expansive group in a public company situation.

Those are very different from what they’re looking for as well. 

Kenny: Absolutely. 

Ryan: One of the things I noticed you kept bringing up. And it’s interesting, as you’re starting to work with some of these companies in your current position. Dog food, right?

Yeah. You bring it up. And I know a lot of product managers talk about eating their own dog food and the way that works, but why is a leader? Is it important for people to understand that term and, or like actually use it as they’re developing product or if you’re going to negate it and you’re going to go down the road where you don’t, you can’t, maybe you can’t even eat, you eat your own dog food based on what it is.

How do you work with that? 

Kenny: That’s a great question. Yeah. I feel like at the end of the day I go back to a point about my earlier transition from design into product management. And one of the things that was so telling was, this trend of highly metrics and business decision focused organization, like the ability to get every data point and understand what’s going to drive those things.

Versus for example, even if you look at some of them. And I’ll use apples as an example, right? The light gray, small font text, and the clickability of that versus some other thing, I think aesthetically, you may make some decisions, but then what are those, what are the impacts? Some of those aesthetic decisions are like business oriented KPIs.

And so I think, like I say that because. When without, like on the dogfooding side of things the implications, if you don’t really understand whether it’s you that deeply understand the product or whether it’s your customers understand the product, if you don’t understand it well enough you risk going in a direction that actually doesn’t meet needs.

And so, I think best case you have means to regularly get input from the market to understand how well your product is actually fit for purpose and how well it meets needs. Optimally, alongside that you’re able to also dog through the product, but knowing that. When you have these deep metrics and ability to AB test things, I would say more times, not even if you think you know what people want, when you test it, you’ll find that you really don’t.

And so yeah, the best case scenario is having the two different data points to bounce off each other. 

Ryan: Yeah, and also there’s a lot of, I think a lot of entrepreneurs and business people that start from the world of dogfooding cause they’re creating a tool for their industry or what they’re doing.

And so you can also get too locked into your own experience. If you don’t really hear what your audience 

Kenny: has. Absolutely. And I think another point on top of that would be, the dogfooding, I guess I see it in two, two areas. One is like really spending time using the product so that you can deeply understand where it wins, where it misses, but also.

That you deeply understand the product well enough that you can ask your market the right questions, right? Because you ask a question. I think I know this kind of thing. Apple or iPod question, do you want a thousand songs in your pocket? Like consumers don’t really know how to answer that kind of a question.

So I think the more that you understand your product, the more that you’re able to then understand the right way to ask questions and to find insights that are going to inform what you’re going to do. 


Yeah, that’s great. That’s amazing. Thanks for that rundown. It was really good to hear the variety of different things that you’ve worked on over the course of time, as well as some of the insights that came within those transitions.

I, one of the things I want to mention here too, is that. Body of work that you have, and the breadth of it has really given you a unique kind of high-level perspective on the way that the consistencies of these things run across digital platforms. People who’ve been working in the industry know this, we’ve all.

We all know it comes down to those very basic, you know, zeros and ones and there’s levels to that. So it’s great to hear how you’ve done it across these different things. 

Kenny: Appreciate that. Yeah. It’s been a fun journey. 


Break One 

Ryan: Kenny’s leadership journey started as many others have in the past, by using marketing, he was able to create product feedback loops so that he can provide great market direction and sometimes discover very hard truths.

Well, it can be difficult to take our own medicine. If we want to succeed, we need to be willing to face those truths. Even when it’s painful. Similarly, as Kenny points out, product managers benefit from eating their own dog food that is using the product themselves to understand its strengths and weaknesses.

However, he argues that sometimes it’s simply not possible to do this depending on the nature of the product. And he suggests that One way to do it is to look at the product from a different perspective. Look at it. How can we explore it from the perspectives of marketing or sales or engineering?

This cross-functional view helps take feedback from different teams within and around the organization and then design a great informed solution.

All right, Kenny, we’re now to the part of our show, we’re going to do the top five tips for leaders that you have. So let’s start with your number one. Tip. What do you get? 

Tip One (Understanding Success)

Kenny: Sure. The first one that comes to mind for me is about understanding success. And I point that out in the sense that I believe the best way to in any type of product investment is to understand what matters. And that means it’s not just your view of what matters, but understanding what other people, what matters to others in the organization. Being able to have that success simplified, right? Not just like a huge mess of data points and that this can then be baked into the roadmap and every day, communications and so forth.

Ryan: And the complexity of that is mindblowing, even though it sounds like a very simple idea, just getting all of those ideas down into something that’s actionable is a really difficult process. 

Kenny: Couldn’t agree more. There’s I can’t count how many times there’s just like you go around the table trying to figure out how that varies?

Everybody actually defines growth, for example, it’s a common term. But you may have 10 different definitions of it. So there’s data governance and you have to make sure everyone understands what this thing is and what the calculation is. And then how do we make sure that’s front and center for our regular, business operations?

Ryan: Yep. That’s great. Thank you. All right. How about tip number two? 

Tip Two (Bringing Teams Together)

Kenny: Tip number two is bringing teams together early and regularly. So I think that one’s a little bit more organic in nature, but I have seen that the output is better when. Different functions can come together and leverage their different expertise even to have debates.

I think debates can be very healthy but to do that, early, and then along the way as well, I’ve seen that, that shapes both. The quality of the end product, and the impact, really has a massive impact on the collaboration culture of the organization as well.

Ryan: Yeah, absolutely. And it really allows ideas to flourish as well. Like you don’t get too locked into one person’s point 

Kenny: of view. Agreed. And I think this is another one that’s interesting, especially as you think about, there’s, the concept of agile transformation which really, I think is one aspect, but there’s another aspect of just overall sort of transformation where, you may end up, it’s not unlike uncommon to find.

Silos and organizations and a team of, as an example, architects who are, may not be collaborating with a team of engineers and or product managers and those that want to own certain decisions. And then how do you break apart those silos so that all of those conversations can be had together.

And everyone knows where your end goal is. And everyone knows which questions to ask. And then we can all bring. 

Ryan: We could spend an entire episode on just how to customize and manage your stakeholder conversations depending on what company you’re in. Yeah. It’s wild. All right. How about tip number three?

Tip Three: (Expect The Unexpected)

Kenny: Uh, Tip number three, we touched on earlier, but I would call it expect the unexpected which is, gets them in a bit about the build or the plan versus what ends up happening at the end. I think whether it’s a quick iteration of an AB test or whether you’re, heads down building something for four months or even a year there’s a lot of Learnings that appear along the way.

And so I think with that I’ve just learned that having a plan is important, but making sure that you have optimal touch points to pick your head up from looking down, to check yourself and to adjust your plan along the way are also paramount. 

In one of the organizations that I was in there was a significant turnover in the executive leadership team where every six months there was some new.

And a new manager and of course, different styles and expectations that came along and which not only affected me as a product leader, but also, my team and our ability to create the results that matter. So of course there’s the overt kind of adaptability and so forth but more importantly, there’s this concept of building trust, which I’ve found to be obviously not only important from a managerial standpoint, but also.

As a product manager, much of what you’re doing is not through direct reports , it’s through influence. And so the ability to observe or navigate through choppy waters but then present enable the team to maintain focus is, has also been really important.

So again, I think this gets back touches both on problem solving, but also on building trust, which is probably one of the most important skills. I would say in product management.

Ryan: Yeah, I think it’s a great tip.

And if you consciously go into things, knowing that it’ll never be what you expect, it’s a lot easier to be flexible. All right. And how about tip number four? 

Tip Four (Have An Effective Methodology)

Kenny: Tip number four gets to methodology. For me, as a product management leader I am very much a fan of, especially as you’re looking to.

Evolve or, improve effectiveness and efficiency along the way, a big fan of frameworks and building something that you can then, you know rinse, repeat, doesn’t need to be perfect out of the gates, but, even the methodology can be iterated on, but I do believe that having a methodology and then also maybe more importantly, aligning on what that methodology is is also very important.

Right. And so, uh, meaning like. You can solve a problem any number of ways. And there may be various constraints, including for example, how much time you have or how many resources are available to you from other teams to help support you or whether or not there are, sales or customer sensitive oriented information that may give you a different direction.

I think it’s understanding what those constraints are designing different types of methodologies before you’ve even started down the path of. And then aligning on, okay, here’s what we’re going to do. We’re going to do X leverage, Google sprint, do a human centered design sprint, sprint, whatever it is, but it’s, we’re going to go put our heads down for two weeks or for one week or for one month and we’ll see you.

And do we all agree? This is the right way forward. 

Ryan: Yeah and this is a subtle thing. Being able to get that kind of deep work and focus in those particular moments is really a challenge sometimes for leaders to let people have. All right. And last one tip number five, 

Kenny: tip five is around execution.

Tip 5 (Proper Execution)

Kenny: So I do think this has been an interesting one throughout my career as well, where, as you grow in your career, you may become more and more disconnected from the actual execution. Whether that be like what the actual, epic or the user story says, or even the acceptance criteria or the, the sign-off of that feature.

But over time, I have found that all those things add up to just ongoing technical debt. In many cases that can end up really eroding the value that you’re actually building along the way. And so, uh, while I don’t believe, again, this is not a black and white thing. I think identifying an optimal way to keep your eye on execution while also, the right level of detail has also been then.

Ryan: That’s a great last tip to land on. And you’re right. It’s sometimes hard to stretch your perspective across what you have to create, what you have to manage, what you have to do in terms of personnel. There’s a lot that goes on in being a product leader. 

Kenny: Absolutely. And I would add one point as well to that, which is part of your role on the PR that I believe as a product leader, as well as you need to keep tabs on how your product is evolving and also help the company keep tabs on that.

And so you might be close to a particular initiative, but as things are constantly releasing your, an ability to kind of like stay connected to that, can. Can be a problem. If over time you just will lose connection to what the end product actually does. 

Ryan: Yeah. Even if we’re myopically focused on a feature, the product definitely has a macro to it, and you have to be able to stay tied to that absolute.

All right Kenny, this was amazing. Thank you for this rundown. It’s a real pleasure to hear from someone who has so much experience in so many different areas. I think your product leadership tips are amazing. So it’s great to have you today. 

Kenny: It was a lot of fun chatting through, so I appreciate the opportunity.

Ryan: Kenny’s perspective, provides great insight into understanding success. It’s important to understand what matters to other areas of the company and to bring teams together regularly, to leverage their different expertise. He argues that we benefit from debates and discussions within the teams so we can get to the highest quality decision possible.

It’s also important to keep an open mind and to be willing to change course, if necessary. Constantly being vigilant of your process and identifying an optimal way to keep executing can help you avoid potential problems down the road and build upon the methods you have in place. We also have the flexibility to continually evolve and improve the process.