This week on the Full Stack Leader we’re talking with Henry Vasquez, Head of Product Management At Cornerstone

Henry Vasquez is a Director of Product Management at Cornerstone, a global leader in talent management software. He leads teams responsible for Cornerstone’s Skills and AI products, and he oversaw two of Cornerstone’s M&A deals and integrations.

Henry brings a deep understanding of enterprise talent management, knowledge management, and productivity software. Prior to joining Cornerstone, he worked at SpaceX as the product manager for document and knowledge management. He is also a 3-time entrepreneur, including his most recent startup, Tribe, which was acquired in 2017.

Henry’s Top 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. Be Patient And Direct When You Speak
  2. Don’t Try And Predict Success Too Early
  3. Each New Team Member Is An Opportunity
  4. Build High Standards By Elevating Great Work
  5. Great Employees Crave Constructive Feedback

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 Fullstack Leader Podcast. This week I’m here with Henry Vasquez. He’s the Director of Product Management at Cornerstone here in Los Angeles, California. Welcome, Henry. It’s great to have you here. Hey, 

Henry: Ryan. Morning. 

Ryan: Awesome. Glad we’re getting a chance to talk about some leadership stuff together, and I know the audience is gonna be excited to hear about some of the places that you’ve been.

Maybe give us a little bit of a rundown of your history and how you got to where you’re at. 

Henry: Yeah. So I had kind of a circuitous path into product management. I sometimes joke that I took the Benjamin button route. So I actually started my career as an early-stage employee at a startup, and I joined a startup right out of college and then quickly became an executive and a leader within that organization as it grew, and then subsequently founded two other startups after that.

So the first seven years of my career were in the pressure cooker. And the first business was in kind the media viral content business, something that a 23-year-old would actually understand. Yeah. And then over time, I found that I really enjoyed more B2B style problems. And so the second business we focused on custom solutions for b2b, a lot of really backend-heavy data engineering work.

And the third business I was actually the c e o of, and that was a tribe and that was a kind of collaboration and productivity uh, solution. And so got into the SaaS world and realized I, I loved b2b, even really enterprise or mid-market sales, the kind of high-touch stuff. And did that for, for a while.

Learned a lot, and did a lot of sales as well. But I was really doing the product management function without realizing it. . And then when we decided to sell the third business to, another startup I ended up kind of taking a pause from the crazy startup world and joining SpaceX as a product manager there.

So, got to pivot into a large organization, with 8,000 employees, and, be a specialist and really focus on the technical skills and focus on product skills. And that was a great choice because I realized at that time that I actually enjoyed the product a lot more than I enjoyed doing all of the other founder functions.

All the generalist things you do as an executive as in a startup. And fell in love with the product worked hard there and then moved over to Cornerstone where I’ve been for four and a half years. Currently a director. And yeah, sort of moved up through from the IC route all the way to kind of senior leadership here at Cornerstone.

Ryan: Amazing. You’ve had a very good taste of all kinds of different environments to work within and lead within. 

Henry: Yeah. It’s, it’s a little crazy. I, I tell people sometimes I’ve done the zero to eight-figure revenue climb multiple times or sort of the zero-to-one product journey multiple times.

And then I’ve been in businesses that were at the billion-dollar revenue scale, but I haven’t really done as much of that sort of middle tier on my own, at least. 

Ryan: Well, it’s exciting. I’m excited to hear kind of what some of the differences are and how you’ve been able to use some of those over the course of time.

One of the ones that come up is going from the tribe, which it sounds like you were really fully engaged as the all-encompassing leader, that you were talking about. Mm-hmm. to moving into more corporate environments. And I was interested at a high level, what are some of the takeaways that you had from being a startup founder and, and going through that kind of like intense in-depth experience and, and what were you able to bring into some of the the larger scale environments that 

Henry: you were in?

Yeah, I mean, I think, so some of the things that were difficult and the challenges that I had to adapt to, you know, one, one thing was up to that point. I. Would walk into a room and people would immediately take seriously anything I said because they saw my title or they knew that I was the boss or the owner, that sort of thing.

And so what I learned very quickly was as a low-level IC in a large organization with, you know, very smart and powerful, influential people you have to, you have to learn how to influence without authority. And I, I just hadn’t done that before. That was a skill that I needed to build. And I also realized just how.

corporate America and larger businesses. Stakeholder management is just such a huge piece of the puzzle and is effective in navigating organizations, and getting things done. I’ve never had a deal with any of these things, at any serious level with startups. And the biggest startup I was a part of, I think got to 65 employees at the time.

And so I was kind of known for being a little bit of a cowboy and just kind of slicing through and getting things done. And, you know, the  Kool-Aid man plowing through walls, and obviously, that doesn’t, doesn’t really work in a large corporation. So I had to kind of adapt and figure out, you know, how do I, especially in the product, you don’t have a lot of direct reports usually right away.

So you’re influencing laterally and indirectly and, and with engineers and people that, you know, don’t report to you, but, but they listen. Yeah, 

Ryan: I think these are really excellent points. I love the Kool-Aid man, busting through the wall example as well. , I’ve, I’ve been there and I know it. And I also just, you know, as a side note, went from a startup that was acquired by Apple and I ended up on these really huge stakeholder meetings in Apple.

I had never experienced anything like that. They’d be calls with a hundred people. And I, I know like that shift from kind of the, the cowboy mentality you’re talking about into that is really, really a big shift. How did it change your actual communication? 

Henry: Yeah, I mean, I think I’ve kept a little bit of that.

People still sort of think of me as this crazy startup guy. I didn’t wanna lose that because in some ways that, that sort of style and audacity can also be a brand for you if you do it right. I think what I’ve learned, and honestly through a few very humbling experiences is, When to read the room and when someone who is an expert or is very high status doesn’t want to be challenged at that time.

There’s a, there’s a kind of juujitsu in sort of working around that. And, you know, for, for me as a startup founder, especially dealing with high pressure sales where I’m making the sale or trying to pitch to VCs who all have, you know, bigger egos, that kind of thing. You, you have to be in this very, like alpha mode a lot.

And in a large corporation, you shouldn’t do that. Most of the time like it, you know, you wanna, you want to be a little bit more a little more smooth, a little bit higher EQ and just it’s a different card that you. 

Ryan: it reminds me of what you said a few minutes ago around not learning how to influence without authority.

Which I really, I really like that statement. And there is this part of what you just described in terms of kind of going direct versus going indirect that I know links into the authority piece, but were there other aspects of authority that you were able to use in startups that just don’t make sense in these corporate environments?

Henry: Yeah, I mean, one of the things in startups is that it’s always, you know, to ask for forgiveness and not for permission. There’s just so few cases where I. Your instinct should be let me s you know, let me go see if I’m allowed to do this. It’s almost encouraged that, hey, just be scrappy. Just go get something done.

Just go make it happen. And if there’s a conflict or you’re doing something that you know, doesn’t align with the, the way that someone else wants it to, to do it, they’ll step up and they’ll tell you about it. But you don’t need to go chasing around trying to pre-negotiate against yourself, right? So, that’s something, and that’s, honestly, I like the startup world better.

I think people should operate more in that way. In, in large corporations, people are excessively cautious. They, there’s a lot of learned helplessness. and it paralyzes people. They go, oh, are we allowed to launch a survey to customers? And then someone goes, oh, I don’t know what the official survey tool is.

Well, can you use a free one? Can you use Typeform? Can you use Google or, or Microsoft or something and just get it done. Well, I don’t know. Am I allowed to keep the data here? Did someone have a license? You know, I, there’s a, there’s a little bit of just like, I would never imagine that in a startup, right?

So it would be like, you know, pick up the pen, get it done, rock out and live another day. And there’s just so many cases I see where that instinct is kind of inverted and, and honestly not that healthy in big corporations. . 

Ryan: Yeah, I think that’s a really good note. One of the things related that I’ve always noticed is and I’ve been a part of both startups and, and large corporations that I mentioned too is that startups tend to be in an offense position.

Like, and thinking about the World Cup right now I’m like, they’re, they’re kind of the, the forwards like trying to score and then, and then you tend to find working in corporations that you’re kind of in more of a defensive mode. And this goes both in the way you’re developing product, but also in the way that you’re kind of accepting new ideas and working with things.

Have you, have you found that make sense too? 

Henry: Yeah I mean there’s, if you just news for anyone who hasn’t worked in a large company, like you’re not going to drop into a team and have no existing responsibilities, existing customers support obligations, bugs, tech, debt, whatever, , legacy, all these other things.

So, learning how to work within those constraints to still have some kind of offense and some sort of progress and new things is an art, it’s a challenge. It’s a, it’s a rite of passage and it’s, it’s something that corporations look for too, right? They’re looking for people who can do new things, who can drive action, who can get ’em out of the paralysis or reinvent and, and find the new growth curve.

 I think that, 

Ryan: that makes a lot of sense. How do you think inside of a big corporation, you’re able to actually create opportunities within teams to disrupt? 

Henry: so I do kind of fancy myself as a, call it a zero to one or innovation product manager or product leader. I tend to be hired into businesses where they need, they specifically need someone to create something that doesn’t exist.

And maybe they’ve tried before and it’s been tough. So one of the things that. I always talk to my team about is, you know, you have to create space for invention and create space for creativity by 


Henry: demonstrating that you can dribble without looking at the ball, right? So there’s a certain amount, and this is not intuitive people, I think people think of creative work as just being, I don’t know, very right-brained or something.

But a, a big key to being strategic and creative and creating new things is actually being very disciplined. It’s, it’s understanding how to have a process, how to how to have mental models and think through things in a certain strategic way. And it also means you cannot be drowning in the operational mess of how to just keep things going.

You, you want to be so good at those things, you don’t waste your real energy on those things. And so I actually do help. , my team sort of build that stack is like, how do we get to that point where we’re just humming along, we’re norming we’re performing, we’re wor we’re working together, and these easy things start to fade into the background and we can create space to do bigger things.

Ryan: Are you able to help your teams work together to kind of teach each other that kind of muscle memory or the, the dribbling without the ball piece that you’re 

Henry: talking about? Yeah. I think it is something that is kind of an oral tradition or taught through examples. And the, the message I always have to people is this, look, you’re a smart person.

You’re like, in a lot of cases you’re a college educated person who makes six figures and you know, the company values you and you’re that sort of thing. You could work anywhere. It is not, you know, it is not cool or, or honorable for you to be doing a lot of low level work and being stuck in the mud like we want you to be.

Creative and be successful and all these other things. So let’s try to figure out how to take all of the, quote unquote easy stuff and make it easy and make it mindless and make it automated and kind of second nature because that’s gonna, that’s gonna elevate us, right? So it’s a, it’s a message of empowerment.

And a lot of times, like, engineers really respond to this well, it’s, Hey, I don’t want you to be doing this annoying, repetitive, manual thing that you are doing either. Let’s work together to make that fade into the background so that you can do really cool, innovative things. 

Ryan: I love that. It does bring up one interesting thing.

I know I’ve thought about a lot over my career of when hiring product people and engineers to some degree, but more product people thinking about the amount of domain knowledge they have within a specific area versus mm-hmm. , the amount of skillset they have As a product manager, how do you take and do your hiring?

Do you consider, are you looking for, obviously a combination of those things, if you can find them, but if you can’t find a combination, what do you do? 

Henry: Yeah, that’s a, that’s a super good question. So one thing that we currently do at cornerstone is we really like to bring people who have the domain knowledge.

Over and have the, let’s say the, the disposition or potential to pick up the skills, and then we develop that part of it, right? So we bring, we, we literally bring people in from our support org or from you know, client success or solution consulting or some other part of the business and actually turn them into product managers gradually over time.

and that is a really good formula for talent. But you have to know how to spot the, the beginning of the potential and the sort of attitude and willingness to pick up those skills. The other skills that people tend not to have will be things like the technical knowledge or maybe the presentation skills or Yeah, just the deep, how software is built.

Just the, the sea legs of communicating with engineers and being realistic and understanding how hard things are. And these are all relatively teachable things, but if someone, for example, is afraid to talk to customers or they’re not willing to go into these stressful situations where they have to present a roadmap and have it challenged or something like that then they need to show that they, they want to overcome that limitation or maybe they just don’t have the personality for this kind of job.

So we, we do kind of, we look for that side of things. . Now there is the opposite side, which is someone who’s just a total wiz at the product or maybe not just product, maybe it’s product design and engineering. Like they have a lot of skills, but they come from consumer or they come from another area.

That’s not what we do in, in talent management. And I think that’s fine, as long as they’re willing to learn the differences and they’re not, they’re not too arrogant when they first come in. Right? So it’s sort of, Hey, are you willing to go on a customer listening to, or are you willing to accept that there are things happening in this industry and with our personas that are not you know, a carbon copy of what you did before?

And I think if, if they have that attitude and that willingness, then the domain side of it, honestly, It is not as important. I’ll just say it. The, it’s, it’s easier to learn. It’s easier to get up to speed. And you see this happen with executive ranks all the time. People will drop into director, VP, C P O titles in companies without coming from that space.

But they have enough analogs, enough overall experience that it’s not too much of a risk and then within six months they can become pretty effective. 

Ryan: Yeah. Thanks. That’s a really great overview. Makes sense. I wanted to go back to one point you made though, around getting those people who are moving up through the ranks and they’re using kind of their domain knowledge to move into different positions within the company.

What kind of training do you guys like to do with those types of people who might be starting at the lower ranks of product versus the higher. 

Henry: Yeah, I mean, product is a weird profession in the sense that there’s not really a tip one. They’re, they’re starting to emerge a a bit of a tip one, but like, definitely when, when I got into it, there wasn’t, so it’s a, it’s almost a mystery, like how do you get the first product job if you, if, if all of them ask for these experiences, like how do you get that?

And the career paths into product are weird, right? So you can come from engineering, you can come from design, you can come from sales or solution consulting, or from product marketing or you can be a ba, like a low level business analyst and then kind of help on that side. So there are a lot of different ways to do that.

What we look at is some of the, you know, I guess doing the job as, as a practical concern so that you learn how to be a junior product manager would be something. Doing a gig or project where you are helping out an existing product manager and you’re specking out individual stories or features that are relatively linear.

And so you’re just practicing the art of being concise and precise with acceptance criteria and defining things for engineers, right. That’s a whole skillset unto itself, and that doesn’t necessarily teach you to think strategically like a, like the real sort of art of product, but it does build one piece of the puzzle that you’re gonna have to have, which is just being conversant and confident with engineers.

Ryan: Great. That, that makes a lot of sense. You mentioned. at the very end there about learning kind of that, that core piece of strategy as kind of the heartbeat of product, which I completely agree with. How do you as a leader implement that and rally your teams behind whatever that piece is? What is kind of your rough strategy around getting people aligned with the 

Henry: bigger vision?

Yeah, I mean, I think every product leader at some point has to start coming up with a, a bit of a playbook for themselves. And you could write this down or you could just have it in your head, but it’s, it’s sort of what is your, what’s your Maslow’s hierarchy of kind of product strategy and understanding.

And I’ve been working on my own version of this, but it’s by no means something I invented. It’s just kind of a, collation of things that, that I’ve learned. And . It’s down to, you know, the basics. , who is the customer? How do we understand that as much as we physically can segment them down. Who’s the buyer?

Who’s that persona? All the characteristics and deep problem analysis, that’s a whole piece, right? Then there’s the market side. There’s, there’s understanding the pricing, the competitive pressure market share. You know, the history, getting into the history of that particular space. How did it get to where it is?

What are things that have been tried before and, and failed and, and where’s the frontier? So there’s, there’s all these little subtopics that are about formulating knowledge. And then I think. You know, of course you do have just kind of the, what, what is technology asking for, what’s sort of the state of the art and you should always just be keeping up with kind of what are the best practices and patterns being used within this area.

When you mix all this together, I like to, there’s a few tools I like to use. So one is, I dunno if you’ve heard of wardley mapping. Have you gotten into that?

I don’t use that one specifically, no. So it’s kind of a strategy mapping exercise. It’s a niche community online. I think it’s really great. It sort of contextualizes the the way that you serve a customer against sort of the maturity of technologies and product capabilities over time. So what you do is, is you layer together your.

what you do as a business and how you connect the value chain to the customer. An example would be, in order to create like a great video player on mobile, we need to layer together, you know, a mobile application a certain amount of compute power, A C D N to host videos a way to gather and procure videos like a C m S that can actually manage all of this stuff.

We need a, we need to bring it together and we need to build a player, and then we need to attract customers. And, so what you’re doing is you’re stacking together these interlocking product capabilities or business capabilities to, to get to that thing at the edge, whereas where the customer buys a thing from you, right?

And so that, that is a map that can be used. And what I do always tell my team is when you’re trying to build a vision and a strategy, Once you’ve defined that customer really well and the problem you’re going after, you need to be able to explain, you know, how all of the investments you’re making are getting you closer to that thing, and that they have interlocking compounding benefits to each other.

They’re not, you’re not just coin operated. You’re not just taking orders from customers. You’re, you’re thinking strategically in different moves. You know, we’re gonna take this village and then we’re gonna move to the next frontier, and we’re gonna, you know, we’re gonna move all of our forces forward to the next line, so to speak, and, and kind of advance methodically through it with the capabilities sort of interlocking together.

And that wardley mapping you can look up maybe link in the show notes. It’s a really good thought exercise for kind of product leaders. 

Ryan: Yeah, I was just gonna mention, we’ll grab that and, and put that in the show notes. It sounds great. , I look forward to checking it out myself. I really like the idea though, of kind of using this linking to build compounding values so that you really understand what the the kind of micro investments, how they lead to a more macro perspective.

But when you’re, when you’re actually leading teams around that, how do you choose to split that up? Like, how do you, how do you break apart product teams so that they look at kind of the bigger picture of the organization, especially as at a, as a higher up 

Henry: product? Yeah, this is tricky. There’s, there’s a really good book called Team Topologies, which talks about how to design organizations that are working on software to, to sort of split up a domain and have them work together, right?

Th th this is just one of the nastier difficult problems in, in organization, and it’s, it’s exacerbated by technology or software rather, because software architectures will tend to mirror the structure of an org, right? So if you break one team down and you say you’re the user profile team, and then this other team is the search team what will happen is they will, they will operate in their own little silos, and you’ll see that the product itself tends to reflect that organizational structure, right?

There’s no shortcut there. You can do a lot of things like slice the domains in a different way. So you can say, and I like this a lot, where people will say, We’re gonna have someone whose job it is to look at more of a persona and their needs sliced across a bunch of different features or views within the product, and follow a user journey that’s tied up to a use case.

That’s really cool. It’s, it’s hard to do that as an enduring team to say that’s the purpose of the team forever. But it’s really nice when you have that layer that purposely intersects across groups as opposed to just saying like, this module in our navigation scheme, like, that’s one team, that’s the payments team, that’s the shopping cart team.

That’s the, you know, sometimes we, we sort of phone it in and it takes some extra effort to look at. Well, if we want to make something really cohesive for one persona, like an admin persona. You know, someone who does like reconciliation of, of finance or something like that, we have to really get into their head and we have to make sure that it doesn’t feel like they’re leaving, you know, they’re going from, they’re going from what are the, the things called adventure land to tomorrow land within Disneyland.

Like, we don’t want them to feel like they’re jumping around between these different modules in our product. And those people are not talking to each other. 

Ryan: I 100% agree with you. It’s interesting. I think, the version of it where it’s more module driven tends to be CTO driven product groups.

 And then the other version tends to be more marketing or kind of business oriented product groups., and there is a really great blend when the two come together and because. Bringing those modules together so that they work across the different personas. And in almost all these cases, like SaaS or commerce or any, any of the kind of big things that we’re, that most of us are looking at, there is some level of multiple persona aspect 

Henry: going on.


Ryan: One of the interesting topics you and I had talked about in the past is really how to navigate your career as a product person, as a leader, developing into it. I wanted to get your thoughts on that again and, and maybe start a conversation 

Henry: around that. Yeah. This has been something I’ve been reflecting on lately quite a bit.

This year actually. A lot of changes happened within our organization. A a few years ago, one of my colleagues who was a kind of a close friend of mine, decided to leave the business after a few years. I think he, maybe he had been there like six years and he had a whole team that he managed couple PMs and, and three or four engineering pods.

They were all overseas. And when I saw that he was leaving, okay. The, I didn’t necessarily want to get into that part of the product. It was a little different than what I’d focused on. But I decided it was good for the stability of that team if I jumped in and kind of raised my hand. And I think I also knew that, you know, taking on more responsibility would, would probably get me promoted as well.

So I took, I took this team under my wing. I led them, I actually hired some new people. We, we worked together for a while and then about nine months later the organization said, we’re gonna take this group and we’d like to redirect their focus towards another priority of the business. There was some redundancy going on, and all of a sudden I re realized I was talking to my boss.

I, I was saying, I’m really frustrated with what’s going on. I’ve got this, these two different teams. I have the team I built, and then this team I inherited. And I had a lot of responsibility, but not a lot of focus. And the, there wasn’t a strong connection necessarily between what I was doing on each side.

And so I, I talked with my boss and realized I need to transition this second team over to another leader. There was someone else she’s up and coming leader within the business who’s working on something connected to that area. And I did the most unintuitive thing. I gave up people, I gave up power, I gave up direct reports and said, take ’em, like we’re gonna do this transition and bring those people under your leadership.

And what that meant is I actually, you know, had less authority, less power, less, less people on my team. But it allowed me to focus down on what I’m doing now and. And then shortly after that, I acquired more responsibility that was really cohesive with the things I do with skills and ai, et cetera, at Cornerstone.

And so it’s a little bit like spring cleaning or Marie Condo. Sometimes you have to take a step backwards to go forward or slow down so that you could pivot and, and speed up. It’s really not intuitive. I think it’s in it’s intuitive to just keep moving up to g gathering more bigger teams, more resources, but that doesn’t necessarily accelerate your career goals or your ability to be effective in a particular role.

So that, that was a little bit unintuitive and, and kind of an interesting lesson I wanted to share.

Ryan: I think it brings up a, an excellent topic that I’ve heard kind of echoed here a couple of different times, and maybe we can talk a little more about it, which is power and authority does not always equate to better leadership . Yeah. And, and this concept of leadership and authority are actually different.

so maybe you could talk a little bit about, like, the distinction in your perspective on that. 

Henry: Yeah. I’m, it seems like, a good theme if you’re gonna give the tagline to the, the whole chat today, right? Yeah. Yeah. , going back to my, one of my first comments. Yeah. Ultimately just being responsible on paper with formal authority for more things.

You know, sure. On your resume you can say, I led this a hundred million dollar business line, et cetera, that, that kind of thing. And that, that’s fine. But at the end of the day , what I look for and what I think is a, a better North Star is to really seek impact and, and to, to personally be responsible for that impact, right?

Like, you wanna learn how to, you wanna learn how to make things happen yourself and make things move forward and actually be part of that. You don’t want to just you don’t wanna just be in the room while other things that are already there that other people did are just continuing to do what they did.

 You want to be challenged and develop those skills. So the authority side of it can be a curse. And to be honest, when I was a principal product manager, which is like our senior most ic role within product, I had so much influence over where we spent our resources and what we talked about as a business.

Because I communicated a lot and I spoke with clients and I, you know, I did a lot of large scale communication and I spoke to the right people and I built relationships with others within the business. And really, it wasn’t honestly that much different than my role today, except I couldn’t delegate things to anyone

That was the, that was the biggest piece that authority got me was the ability to. And, and 

Ryan: probably oversee a variety of different people that are doing roughly the same thing, I’m assuming. 

Henry: Yeah, yeah. I mean, honestly, I would’ve, I would’ve kept doing that IC route forever, but that it became obvious to me that the way to maximize the success of my initiative and, and what I was trying to accomplish at the business was to actually build out and train and, and grow a team around me and figure out how to copy that whole thing and make it.

Ryan: yeah, I, I had a, I had a great boss sometime back when working for a division in the New York Times. This guy, Dan Sherlock, I put his name in here cause I really, learned a lot from him. But one of the things he really taught me was how to manage managers versus how to manage just kind of like 

individual contributors. And there is a little bit of a secret sauce to get that to get that piece out that you’re talking about, which is that influence. , do you work with the the team differently than you think you would work with more individual 

Henry: contributors? Yeah, 100%. There’s a few things.

One is with individual contributors. If you delegate something to them, there’s no ch usually no chance for them to re delegate that to someone else. Whereas with mm-hmm. , the people managers that I have, I delegate a lot to them, partly as a way for them to feel a little bit of pressure and to learn and to be challenged, but also so that they learn how to delegate themselves.

So there’s a little bit of that relationship and I don’t have to be quite as directive or specific about what I need usually with those people because they, they anticipate my needs a little bit more and I can be more succinct or blunt and they’ll step up and take it with, with ics I find it really depends on how senior someone is.

If they’re more junior, you’re not gonna be able to just like lob something over to them and you’ll scare them. Right. So you sort of need to , you wanna build up that understanding and the context. Lead with context and and you always wanna do that, but you have to be more careful with it. Cause you don’t know if they have the skillset or they have the confidence or they need to be you know, you need to share more knowledge with them, that kind of thing.

So I just, I find that it’s probably personally, it’s, it’s easier to manage managers maybe because I can, I can be a little bit tougher with them. But yeah, it’s a different kind of skill. Both are rewarding for different reasons. All 

Ryan: right, 

As we’ve been talking, one of the things that’s really coming up for me is how you transition from an individual player. Into more of a dynamic leader that’s going to oversee people and guiding, guiding teams towards that is really important. But just thinking about it from your own perspective especially as a product person, you’ve been a, you’ve been a leader or a manager across a product line, so you’re working, you know, across departments or, or across different areas to bring things together, but you wanna transition into more of an actual organizational leader.

I’d love to hear your thoughts on like, how someone might be able to make that jump. 

Henry: Yeah. This is a tricky one because, you know, before you make this journey, you’re kind of always in ic. And once you’re past this point you’ll probably mostly function as kind of a people manager or executive.

But making that transition within an organization or within your career for the first time is, is challenging. . Ultimately this is kind of my formula or playbook to do this. And I was lucky enough to do this at one of the startups and then I’ve, I’ve had a chance to do it now as a product leader at Cornerstone.

And it’s identifying first who your right hand person is gonna be at training and building and investing in that person until they could do more than half of what you used to do. And so the, it always starts with this kind of beachhead. I would not try to, you know, instantly get five people as direct reports overnight unless you have to.

It’s much better to sort of build from what you know and then sort of transform your own job out of that thing. So my, my experience with this was, you know, back in 2020 we acquired a startup that was gonna help accelerate the initiative that I was leading. And I was responsible for this kind of, Multi-year r and d initiative.

And we gained a product counterpart through, through that process. And so I was thinking, okay, this is gonna be that person that I invest in that’s gonna do some of what I used to do, and then I’ll manage them and build around it and that sort of thing. And unfortunately, like a lot of acquisitions, this person decided to leave the company after about six months.

So I was like, okay, I gotta start over. And there was an, another individual that I had built a relationship with became pretty close with. And so I found, okay, this is the next person. This person is who I’m gonna invest in. I recruited them on my team, started knowledge sharing, working together, delegating all that stuff.

And then that person left a year after that. So I, at this point, I had invested twice in like, this is how I’m gonna bootstrap and kind of get my team going and scale this out. Eventually, two years after that original acquisition, there was another person within the organization, the current person who’s kind of my right hand now, and I recruited this lead product manager to my team and really invested in this person.

And they stuck around and they helped us build out the whole team, and now they manage all of the ics. And that changed everything. I mean, that was, that what, that accelerated my career. It allowed me to think more strategically, to be more of an executive and, and take on different things. And really you’re only as good as your team.

I mean, I, I couldn’t do it without that person. So when I think about the formula, it’s about trying to figure out, you know, how do you make that happen faster? And even if someone’s gonna leave, you still have to invest in them. Like all, all those people before, I never once thought in the back of my mind, well, they might leave, so I’m gonna hold back or hedge my bets.

It was like, no, this is my ticket. This is, I I’m going to pour everything into training and supporting and building this person. Yeah. 

Ryan: Wow. This brings up so much. And I think it’s such a great example of how, how really developing your team can change the trajectory of everything you’re doing. And I, I have reminiscence of a very specific conversation.

I had one time around, a really great VP of engineering gi giving me this piece of feedback, which resonates with what you just said, which is you wanna be trying to work yourself out of a. . And that concept like stuck with me for a long time. It was one of these spots where I was just trying to do my job the best, do it the very best, but by staying there, I’m just staying in the same thing.

But by working yourself out of a job what really happens? And I was wondering , if that resonates with you. 

Henry: Yeah. My, my first like, real boss in a, in a kind of call it white collar office job said, You know, here’s the formula. I want you to do this job and then I want you to figure out how to explain what you do to another person.

Then I want you to go hire that person. Then I want you to train them. Then they do it, then you manage them. Then just recursively, do that up the chain, and just, yeah, figure out what the next thing was. And in a startup it was all over the place. It was like I was the first person to do our product analytics and then the first person to write all of our specs for engineers and the first person to think about our design system.

And, and then there was always an expert or someone who would ultimately end up being better than me at that job that I could kind of build and manage around me. And that was a very good, like, selfish motivation for me. Cuz I, I wanted to move up. I didn’t necessarily wanna do all of those things forever.

Yeah, that makes 

Ryan: sense. 

Well, I really appreciate all of the insights. You’ve really laid out so many different things. Whether we’re looking at moving from a startup into an enterprise organization or whether we’re looking at kind of jetting our career from individual contributor up to an actual leadership position.

 But thank you. And, and what a great. 

Henry: Thanks, Ryan.

Break One

As with many of the leaders that we have spotlighted on the podcast, Henry comes from a pressure cooker environment, moving from a small company to being a product manager at SpaceX in an organization of over 8,000. He talks about the discipline it takes to make the climb from zero to eight figures, a challenge that Henry has navigated many times, and the reality of which shows how effective your process can be.

Something that stands out to me is Henry’s attitude towards. and what you do with it. The perspective of focusing your time on making the majority of your work seamless and reaching a flow state in your product team is hugely beneficial. Also, using all of your collective energy on important work that matters makes the easiest parts of the job, second nature.

Ryan: All right. Welcome back everyone. We’re here again with Henry Vasquez from Cornerstone, and we’re excited to hear his top five leadership tips. So, Henry, maybe you can share your first 

Henry: one with us. Yeah, I had a fun time with this kind of prompt cause I was trying to think, you know, what are things I could say that, that are, you know, pieces of wisdom and, and lessons I’ve picked up, but maybe something that people haven’t heard added that extra challenge in.

Tip One (Be Patient And Direct When You Speak)

Henry: So the first one is, as a leader, be patient when you’re in a group setting and then strike with brevity and precision when you talk. So I kind of think of like the Cobra strike style of, of sort of thinking about group dynamics in meetings. It might seem sort of obvious, but it’s a good heuristic to think about this.

And it’s not the only style that you want to use, but it can be very effective. So what I like to do sometimes, and not every time, is we’re in a group setting. And what I’m doing is I’m, I’m listening and I’m taking notes and I’m sort of sizing up the different players and the perspectives and what they’re doing.

And what I’m trying to get to is how do I find the essence of the topic what’s blocking us, what’s the decision that has to be made? What’s that uncomfortable truth or something that needs to be elevated? And I’m, I’m seeking to sort of figure that out. And then once I figure that out, I’m trying to figure out how to communicate it in a very persuasive and succinct kind of way.

And it’s almost like you, you don’t have to. Say a whole lot. I mean, you can ask questions and sort of un unveil things along the way, but when you finally decide to interject and insert your opinion or something more directive, it’s kind of using that one volley as being more about quality than, than about just saying a lot of things.

 how do I, how do I get to the core of what it is to drive clarity and direction for the group? 

Ryan: Yeah, that makes sense. And working in that level of patience is a developed skill. A lot of time for people. Yeah, absolutely. All right. What do you got for number two? 

Tip Two (Don’t Try And Predict Success Too Early)

Henry: So this one is going back to the beginning of my career and it is trying to predict success beforehand is mostly futile.

You should practice your ability to spot a winner once you see one. So this is kind of a general I would make entrepreneurial or maybe maybe a product lesson. Which is, you know, just some context. I, I’ve started a couple of businesses that have gone from zero to, you know, seven figures of revenue.

A couple of products that have gone from zero to seven or eight figures of revenue within businesses created probably 50 new products, entire new products from scratch. And there are so many things you can do to improve the chances of success and do things the right way and be thoughtful and do, you know, great discovery and really understand the customer problem, all of that.

But there’s so much randomness and there’s so much that is not in your control, and it is not a perfect science. But what I will say is you can get very good at recognizing what the beginning of something that’s gonna work looks like. So in the adoption, in the analytics, in the way that people react, there are some patterns around.

The way that successful things are gonna come together. And I think that skill is something that you will see like angel investors or VCs develop. It’s also really good for you to develop that skill so that you don’t get too enamored with the idea of analyzing something to predict its success beforehand.

And you get more comfortable with the idea of trying a lot of things and then knowing how to double down really hard on things that work. You know, some, sometimes it will blow up right away if you’re really lucky, and that can be very random. But there’s a more kind of consistent pattern, which is something that looks like a snowball.

It starts small, but it has this steady kind of momentum. It has the signs of something healthy that’s gonna grow. And it wasn’t just an accident. It’s not like we did a promotion and then that’s why all the attention is there. It has the mechanics of something that’s gonna do well. I think knowing what that looks like is such a key skill.

Even more important than trying to predict success before. . 

Ryan: Yeah, it’s a tricky one too, because there’s a lot of great salesmanship out there, a lot of great promotion of things that, that may or may not have that. And the kind of slow and boring route is difficult to sit 

Henry: with sometimes. . Yeah. 

Ryan: Yeah.

All right. That’s great. How 

Tip Three (Each New Team Member Is An Opportunity)

Henry: about tip number three? Each new teammate you add to your team is an opportunity to upgrade your team’s culture. This is super important. The example I always give is, you know when, when new people start, you want to make their onboarding amazing. So whatever you use for the na the last person, take that, make it 20% better.

Or like, think about what you did well and try to try to have a great first experience, a great first week, a great first month a great first team meeting, that sort of thing. And when that new person joins, you have the opportunity to start teaching them the standards and show elevating things that are working and.

Kind of celebrating those wins. And you have a chance to sort of lead by example. But actually the most interesting thing is this kind of, I’ll call it the birth order effect for new hires, which is all of the junior people or, or like the newest people, right? The, the babies within your group. They become the older child when a new person joins, right?

And so it changes their mindset. They’re no longer, they’re no longer in this kind of submissive position. They’re actually becoming a teacher. And you can, you can switch that and sort of play to your advantage by putting those people in a context where they get to teach the new person, they get to lead them, they get to kind of seem like they know what’s up and they’re part of the, leadership team or they’re part of the old guard.

And that really changes people’s mindsets. Just, just like a new child will change the behavior of the older child. Yeah. And I 

Ryan: think when you’re in a position of beginning to teach something that you know pretty well, it solidifies your insight and knowledge around that altogether and builds confidence.

So, so it makes total sense. Yeah. Great. All right. How about tip number 

Tip Four (Build High Standards By Elevating Great Work) 

Henry: four? What do you have? The best way to build high standards is to elevate the great work you have within a Museum of Excellence. So it’s related a little bit to point number three. But what I, what I’ve learned through coaching and teaching people is there are many different learning styles.

There are a lot of people who want to go try something. There are some people who really need a theoretical understanding. But a huge percentage of people, one of the most effective things is just learning Monkey c monkey do learning through my mess. Just seeing something that works and then going, trying to copy that thing.

And so one of the ways that you can be effective in building a team culture and, and building high standards is to elevate great examples. You know, take a requirement, stock or p r d and show people this is what it looks like. This is what something really good looks like. Here’s a great memo or a great mock press release.

Here’s a, here’s the best presentation we’ve got. Here’s this really, really great part of our product that we want to elevate. When people are told that this is what good looks. They start to raise their game, they start to figure out how do I copy that? Or how do I, how do I borrow lessons from that?

So using things like shadowing and ride-alongs are great, but also just having assets. I, as I said, the Museum of Excellence, just build up those hits that you wanna show people. 

Ryan: great. The Museum of Excellence. I, I really like that. All right. And your final tip, tip number five?

Tip Five (Great Employees Crave Constructive Feedback)

Henry: Yeah. So this one is, is really near and dear to me because it’s a practice I like to do with my team. So the tip is great employees crave constructive feedback in a psychologically safe context. So part of being a good manager and coach is figuring out how to give feedback and make sure that it’s not always just from you there’s a lot of peer feedback as well.

And so something that, that I love to do and it really, the first time this. Happened to me as, as sort of the subordinate. And where I got to experience this when we were, we were actually watching a tape of ourselves doing a presentation for our product when I was going through the Techstars program in 2015.

And it, it was almost like, you know, being a, being an NFL quarterback, watching the game and going back and analyzing the tape, I’d never done this before. I’d never sat there and dissected everything about how I was presenting my body language. Yeah. Examples, everything. It was, it blew my mind. And I was like, oh, why is it so hard to do this?

People are scared. It’s maybe, it’s, there’s no psychological safety, that kind of thing. And what I realized is, you know, that kind of feedback, you people aren’t gonna do that automatically. You have to kind of. A safe environment to do that. One way to do that can be, you can go do that tape-watching kind of thing.

Literally. I mean, you could record a, a zoom of them talking to a customer or something. You can do that in a one-on-one context and then it’s probably gonna be safe or it’s safer. Right? Because then, their peers aren’t around. But the coolest one we’ve done is actually team sparring. And the way it works is that the person who’s kind of the ace, the person who’s like on call that time, they have a topic, they have a prompt they have to prepare for, and it’s based on something they should know in the business, something about their product, and they’re gonna defend that.

As best they can in say 30 minutes. And everyone knows the prompt beforehand, and all of the rest of the peers on the team are gonna ask questions. Almost like the Prime minister’s questions in the UK is as fast as you can. They’re just gonna have all these bombarded questions and that person is gonna try to answer based on what they’ve researched, what they know or they’ll say, I don’t know.

And they’ll give, like, they’ll couch their answers, that kind of thing. And then what we do is we privately the notes on how they did from each person to that person without telling anyone else, right? So they’ll say, I really loved your answer for X, or You need to work on your answer for y It’s all private, so there’s no public shaming.

 We make it a really fun and kind of celebratory thing and people, every time I’ve done this with people, the person who’s the ace, they always feel amazing by the end because they learn something, they got to practice and it’s fun. And it’s usually not punitive. And we always, you know, we kind of celebrate someone getting all the way through the gauntlet.

I always do this first with people, so I’ll raise my hand and I’ll play that person so everyone can see what it’s like to be that person without having to do it the first time themselves. And then, and then we rotate who gets to do it, and it sharpens your thinking. And then  the feedback is very constructive and it’s private

So that’s something that I love and, I’ll use it with any team. I love that 

Ryan: tip. This is such a cool tool, to put into place. And just to reiterate, the thing that you’re talking about that makes it work is the safety beforehand. So they know when they do this, this is about building them up versus tearing them down.

Yeah. And I love the way you approach that and lay it out. All right. Well, it was amazing to have you with us today, Henry. I really appreciate all of your feedback. Those were excellent top five tips. We look forward to letting our audience hear your insights and we’ll, we’ll be sharing some of the links that you mentioned earlier on the podcast within the show notes.

And it was great to have you here. Thanks for joining us. 

Henry: Thanks Aran.

 As Henry mentions, there isn’t a front door for product and tech. Disrupting the product industry requires a strong team and an effective group dynamic. communication is a recurring topic on our podcast, and Henry brings a unique perspective with his quote-unquote Cobra approach.

Addressing his team directly and effectively seeing each new team member as an opportunity to build on those team dynamics is important to him. And with so many variables in the success of a product being in our control, success requires a well-developed sense of observation. Henry shows us that an effective team with a well-developed process can generate the momentum needed for a successful product.