Story Samurai

Ari Block (00:00)
Jordan, what an absolute pleasure. It's great to talk to you again. I have a small confession. It's always fun for me to talk to product managers since that's my thing. So it's very good to talk to you again. I want to start with an easy pitch, okay? I'll have some hard balls. Those will come at the end. Tell me about your favorite moment in product management.

Jordan (00:26)
I was working at FlyReal and, you know, the other, the other folks in product had left. So I was the only product manager and the team had lost the engineering team and then sort of other teams had lost a lot of.

sort of trust they didn't get a ton of visibility into the product thought process prior to my joining. And that was something that I noted right away and worked to resolve, put in place processes and be very intentional about my communication.

And it took, I mean, I'd say it took like six to eight months of really working and sort of repeating and being very clear. But they got to a point where I felt like I really built that trust with both the stakeholders and the development team. And that was just a really, a very fulfilling moment for me.

Ari Block (01:23)
So this is an incredibly important point for product managers. And I want to break it down. There's the trust of the engineering team. And then there's the trust of the other stakeholders, which I want to delve into each of those and what that relationship looks like. But let's start with the engineering team. So if I understand you had an inbound component, you were working directly with engineering. How do you build trust with an engineering team? How can it go wrong?

And if you will give us some tips about how to make it go great.

Jordan (01:57)
Yeah, yeah, I think that the biggest way for it to go wrong, and this is from personal experience, is by...

if the engineering team feels like you are sort of randomly deciding things, you know, they ask a question or a stakeholder has a request and you're sort of like, yeah, okay, I don't have a reason to say no to this. And, you know, they're sort of getting things, but not really connecting how does this map to our product strategy, our mission, our OKRs. For me, I think that's the fastest way to lose their trust because pretty quickly, they get to a point of like, what are you here for? Like if that's what you're doing, like then, you know,

Anyone can do that. And so I think the biggest piece is really having a strong product strategy that's really well aligned to the company strategy. And then continuously repeating that, both when you're speaking with the team about why we've prioritized and reprioritized things that we are, and in terms of sharing why you've made decisions in a certain way.

I think the other big piece, and this is really, I think, key to collaborating with anyone, but is genuinely taking into account their feedback. So I'm not a past developer, so I don't have that engineering experience. And I think something that can really rub engineers and probably anyone the wrong way is when it feels like I'm not taking into account their expertise. So not only can that destroy trust, it really...

takes away a really valuable input from my own decision -making process. And so I think by sharing the strategy, sort of contextualizing, getting everyone on the same page, and then really soliciting their strong input, and when necessary, changing my mind when something that they say really makes sense.

Ari Block (03:49)
I love that. I've worked with so many engineering teams and engineers are incredibly intelligent, they're incredibly smart. And I found by, you know, pretty subscribing to that transparency that you're talking about, subscribing to seeing them as a stakeholder and not an execution arm, you actually get a lot of value. And I've even found that...

They are more productive when they feel that they are part of the team, they are listened to. So I just love everything you said. I found it to be very true from my own experience. But the engineering team is not our only stakeholder. We've got the C -suite, we've got sales, we've got marketing. Let's dissect this and go one at a time.

Jordan (04:39)
I think for customer success, they can often feel underappreciated and like an underutilized input into product strategy, product decision making. Like you said, they're the ones on the front line. They're targeting customers every day. They have the best feel for the pain points that the customers are feeling with the product, for the desires that customers have for the product. And...

I think they can often feel a little bit ignored, right? They're often bringing bugs or issues that, you know, in product you have to say, this isn't something that we can work on. I think it can often feel like, what is the point of sharing these things with you if you're always like, eh, this isn't a high priority enough to work on? So I think that the key, you know, both proactively and reactively from the start is to help them understand that you appreciate and understand what they're going through, what they're seeing.

and how valuable that can be to the product development process. And once something comes up, you're not always going to be able to work on something. There are going to be times where you have to say, this isn't high priority enough, but...

again, showing that it's important and then you understand why it's important and then working with them, you know, as much as possible, not necessarily compromise, right? You don't want to do something just for the sake of meeting in the middle. But something along the lines of can we revisit this in three months? Can we revisit this if these numbers going up and you see a drastic increase? Is there a workaround? Is there a shorter way that we can look at solving this issue that we're having?

Ari Block (06:11)
It's so important. I mean, I see this go wrong so many times where customer success is input is causing churn because it's not listened to carefully, which is, it just has a huge impact on the bottom line. And, you know, in the worst situations I've seen customer success are being treated as QA because engineering processes are failing and then customer success is, is, is testing basically with the customers themselves. Just imagine that.

and they're being ignored. It's just such a huge missed opportunity and your take on really listening and respecting and really giving customer success a seat at the table is so incredibly important from my experience. I really appreciate that. Let's talk about sales and marketing. When do we engage with sales and marketing?

How do we take their feedback? On the one hand, we don't want them going out and saying all the stuff that we, we have all these new features, but actually we're just talking about future plans that maybe won't come to reality. But on the other hand, they're also working with customers every day, not customers, but prospects. How does the sales and marketing element fit into the product management picture?

Jordan (07:33)
sales and marketing, they tend to get very excited when you talk about potential new features and forget that word at the beginning of things. And so I think there's a couple of keys. One is being very intentional with, you know, what you do share with sales and marketing. And being very...

very clear on this is something that we know is going to come. And being very, I think, generous with your timelines in terms of if it's something that you're predicting happening in a month, depending on how good you've been, the team has been at delivering on timelines. I think making sure that they don't say, well, you said it was coming in a month. Now I'm going to start telling customers. So that constant communication back and forth with sales.

I think that the struggle there is that they're out there talking to customers, sales and marketing, on a day -to -day basis. And so there can be a lot of blip feedback that they're getting, right? They have one customer, two customers that say XYZ thing, and they start questioning the whole direction, or they think that you should go a certain way, a certain decision should be made. And so I think having a lot of discipline on the product side to gather that feedback, because it is incredibly valuable.

but to gather it and then contextualize it. What kind of a customer was this coming from? What is the context? And are we hearing patterns? Is this a pattern that we're hearing? And if you can identify that, but it feels really important, then having a plan to address that, right? Is that something that sales can continue to ask customers, potential customers as they speak with them to start digging in a little bit more.

Ari Block (09:16)
This is such an important point that you're bringing up. And I mean, we call this in the realm of psychology, recency bias, right? The sales team goes out, they hear something from a customer and they're like, this is the most important thing. And not only that, there's a perverse incentive because they're trying to close that deal. So there's recency bias, there's a perverse incentive. I need this to close the deal. So now this is the most important thing in the world. And that most important thing of the world is something else every two weeks, right?

or every month or three months depending on the length of your sales cycle. As product managers, how do we counter all these psychologies that are working against us? And you started to say, right, it's about planning a strategy and capturing. Tell me more about what that looks like almost on a day -to -day and month -to -month and quarter -to -quarter perspective.

Jordan (10:06)
Yeah, yeah. I think that product strategy is an often underappreciated piece of product management. And I think it has to start with a really strong company strategy, mission, vision, and guiding statements. Because products can put together a theoretically brilliant strategy. But if that doesn't map up to the company objectives and the company mission, then it's going to be a miss. It's going to be a fail. And you're going to have a really hard time getting people bought into it.

So I think really starting with understanding that so that you can contextualize where product fits within the greater company strategy. And then I like to do sort of a, I like to sort of start on an annual basis thinking about what are the big company initiatives that we're working on this year? What is our three to five year picture that we're mapping toward and essentially putting together a North Star, right? There's always a hundred really important things that you need to be working on at any point, which.

means that there's no important things if you're working on all 100 of those. And so really being disciplined about these are the two areas that we've chosen to focus on. And here's why. Here's why this opportunity cost that we're paying is going to be worth it. And then from there, everything should really cascade down. So on a quarter to quarter basis, revisiting. But if you are changing your strategy on a quarter to quarter basis, you better have a really good reason.

Ari Block (11:29)
That is so important. I come to companies and I see they don't have OKRs, which really means that either they don't have a strategy or they don't have a measurable strategy or their strategy is just, let's sell more. But that doesn't help us as product people. Let's dive into the strategic aspect of helping the C -suite. So we talked about sales and a little bit of marketing and customer success and engineering.

But product leadership has a very important impact on leadership. If they're not giving us good enough, let's say, target strategies, go to markets, OKRs, there's really nothing we can do with that. So tell us a little bit about that experience and how we can guide leadership to have better synergies with their product strategy as opposed to their company strategy and how those two really fit together.

Jordan (12:22)
Yeah. So I think one really big part of that, I mean, that's a great point. The product strategy is only going to be as good as what is coming down from the top. And I think otherwise what you end up seeing is kind of the random walk, right?

Everyone's working on different things in different directions. If you have OKRs, if you have KPIs, those are not being meaningfully moved even over longer time periods. And they're sort of a question of what is our product, who do we serve, why do we exist? And I think one...

key part to that is if they don't appreciate the importance of the product strategy and connecting that with the company strategy, is just starting to have those conversations and talking about, here's what the consequences are, here's what we're missing without that product strategy. You've seen XYZ over the past three months, and here's where...

Here's where that gap is that's driving these issues that we're seeing. And I think being willing to work with them to get to something that, you know, the different inputs are there and...

the executive team understands and feels bought into so that you're not constantly having to go back and clear every little decision, every little change with the executive team because you know that you are all moving in the same direction and that the product development is moving in a direction to move the needle for the company.

Ari Block (13:58)
I love that. Jordan, first of all, thank you. It's always fun to talk to you. But I mean, this is so important. So I just want to call out to the audience what you're saying. Product strategy does not live separately from the corporate OKRs. In fact, every product strategy, and Jordan said this before, it ties back to the OKRs. How is the product strategy implementing the organization's key objectives? And that's so important. And if the

executive team is not bought into the need for that alignment. And that's a little bit of change management that product leads and helps happen. So it's such an important point. I really appreciate it. I want to pivot a little bit away from, let's say, the core product stuff and talk a little bit about organizational culture. It has a huge impact on engineering, on product, on sales.

Talk to me a little bit about the good, the bad, and the ugly in regards to the stuff that you've seen from the perspective of as a senior product leader and how that positively and negatively impacts the organization. And really what I want to share with the audience is the CEOs and VPs listening to us. What are the cultures that help product and the company be successful from your eyes as a product leader? And what are the ones that just get in the way?

Jordan (15:22)
Yeah. So I think that, you know, I addressed this a little bit at the beginning, but a lack of transparency is a huge one. That's one where it can lead the team to feel like, you know, you're just randomly moving. It can lead stakeholders to feel like, what are you doing as product? Why have we trusted you to decide what to do next with things that impact our teams? Because this isn't, you know, this isn't connected and this isn't helping me.

you lose a lot of trust in all of your stakeholders, including the engineering teams. So lack of transparency is really key. I think another...

something I've seen that is difficult culture -wise, is when product and engineering become a feature factory. I think that's something that you hear a lot about, but whether it's sales, customer success, or even the C -suite sort of passing down, hey, we think XYZ feature would be great, and we would love for you guys to go ahead and implement it. It's just not utilizing the product and engineering functions to their greatest advantage, and I think that you get

really low morale in that case.

Ari Block (16:36)
or my favorite when the CEO comes and shows you a feature the competitor has and we have to do this tomorrow. So have you got have you has that happened to you?

Jordan (16:47)
definitely from other exec functions have seen that. A customer had mentioned that this other competitor has this and we need it to be able to keep up.

Ari Block (16:59)
I, you know, those are hard ones to deal with, but I always find that going back to the strategy and seeing how features fit within the strategy is helpful. and then the other one that I love is, well, you know, is this going to help one customer and then we're a consulting firm basically, or is this basically going to help 80 % of the customers? And then we really are, you know, a product company. That's, that's wonderful. I think transparency is such an important point because.

Jordan (17:21)
We're a big one.

Ari Block (17:26)
It's not only sharing the information and direction, but also how decisions are made. And how decisions are made or how product managers prioritize is such a core, let's say, part of the science and art. Talk to me about roadmaps, backlogs in that process. What does that look like? And again, how can it go wrong and how does it go right?

Jordan (17:47)
Yeah, yeah. So I think that really starting from the roadmap perspective, which should be driven by that mission, vision, and those OKRs, everything that you're doing should really map back to that. So if I have something on the roadmap that doesn't contribute to one of my OKRs, I'm going to ask a hard question of why do I have that on my roadmap? And sometimes there may be a good reason. And as long as I can know that and as I can explain it to all of my stakeholders,

That's fine, but you really want to be careful how much time you're spending on things that aren't going to move the needle and what you've decided are most important for the team to focus on. And so putting together the roadmap, you know, I think being realistic about timing because, you know, engineering work and product projects always take longer than you want them to. And adding in time to iterate because your first version is rarely going to be perfect. And so, you know, there's nothing...

I think there's nothing worse than feeling like you've sort of gotten your minimum product, your minimum version in, but don't have time to do iterations on it and sort of ready to move on to the next thing. It just feels like you've incompletely sort of half done something, right? You've taken time to do it, but you haven't really fully done it. But I think those are really big pieces of the roadmap.

There's a balance between flexibility and sort of letting your long -term commitments guide you. I do think that it can depend on the team a little bit. It can depend on the product and the industry. But having that flexibility, I found, can be pretty important. We tend to roadmap like a year out. But the reality is, especially if you're not in a hardware space, you don't really know what's going to be most important in nine months. You may have a pretty good idea at the high level of what's going to be important.

But as to the projects that are actually going to be most important to contributing to those things, you don't really know.

Ari Block (19:47)
That is so important. And I think there's, have you experienced this gap between the product management leadership and the C -suite where they don't really understand this philosophy of we have a theme, we have features, those are not the same thing. And, you know, we have the strategy. Talk to me through how the difference between, you know, we're not really product managing, you know, one feature at a time.

but we're basically, we have a strategy and then we have themes in that strategy. And we're going in a direction towards, I think you called it a North Star at the beginning. Tell me more about if you've experienced that gap with management and then how you've kind of walked through that and how do you communicate to your environment that, let's say philosophy of product management.

Jordan (20:37)
Absolutely. I think that latching onto specific features is something that's very easy to do. It's very common and it's something that you have to learn pretty early on in product that can be really dangerous, right? Because your goal isn't to build XYZ feature. Your goal is to serve XYZ customer in completing their job and to move XYZ business metric that...

you know, shows that you're moving toward where you want to be going as a company, that North Star that we were talking about. And so when you have that, you know, great strategy, great mission, a great idea of where you're going, and then you have sort of these are the three big areas that we're focusing on in order to achieve that, what that gives you is that flexibility, right? So you have the ability then to say, we thought that this project was going to be the highest priority, we thought it was going to be the highest impact, but we learned these things, which actually mean that this is an opportunity,

it's a better opportunity. And so it means that you're able to be responsive to things that you hear and see in the market, to what you're seeing in the data. And essentially you keep that agility, that nimbleness that, you know, especially for startups and young companies is really what differentiates them from the big behemoths who have to move very slowly.

Ari Block (21:55)
product managers, we don't have a crystal ball. We don't have the word from God. What we do is we build a hypothesis and then we test that hypothesis. Then we collect data and then we change our mind based on the data we've collected. Tell me, let's jump into a specific story that you have and tell me about.

one of these instances where you thought you were going there, but actually the data showed you should go somewhere else.

Jordan (22:24)
question.

came into a startup. And so what that meant was that a lot of what we had been doing up to that point was figuring out exactly what our hypothesis was, what the market was, what the customer need was. And that had been driven by very close collaboration with a few clients who were working with us. And...

the input that the company had gotten from those clients was invaluable. It was the only reason why we were where we were at that point when I joined the company. But I think that when I joined, we were at a bit of a transition point and where we needed to shift from, you know, primarily led by client XYZ wants this feature to led by a strategy, right? A thinking about here's what we can do in this market.

Here's our 80 % customer rule here, the kind of customers that we want to serve and exactly how we want to serve them, and continuing to iterate on small hypotheses rather than moving wherever our customers had whims from a day -to -day basis or a month -to -month basis. And so when I joined, we were really focused on, we had this long list from customer success and from sales of these are the features that our customers want us to build next.

And that was difficult. It was a plan. They had been communicating that with our customers for months and been promising these things. We were already behind on delivering those things. We had had a lot of over promise and under deliver actually on the product and engineering side. And so there was a real lack of trust, I think, between customer success and sales and the product organization.

There was also, I think, a frustration on the product side with, you know, we can't just build these features because customers want them because they want them the most. And we've been promising them for a year that we were going to build them. So, you know, we hit a really low point maybe five or six months in where we were still having trouble delivering on all of those things. You know, we'd started to talk about whether those things made sense. And...

I think a really big question in customer service and sales mind is, are we going to lose these customers? For customer service, are we going to lose these customers that we've been working with for years? For sales, are we going to not close this prospect that we've been working for quite a long time to get to closing? And feeling real frustration and...

we hit a point where we had the hard conversation of are we going to be that, are we going to be that consulting shop that every single customer that we currently have, we have to keep them and so we do whatever they ask us to do, or are we going to have a cohesive approach, that cohesive approach, that North Star that guides the product and are we going to decide what kind of a product that we want to build? Of course, driven by customer feedback, we can't build in a vacuum without any customer input.

But we're kind of at that point, right? We're not babies anymore. We're not doing the random walk that you're doing at the very beginning of a startup where you're just building what people ask you to build.

Ari Block (25:51)
incredibly difficult, right? I mean, first of all, thank you for sharing that story. I think there has never, like every single product manager has gone through that pain of, am I going to make a decision now where we're going to lose a customer? And it's very easy to be the product manager that tries to please everyone. And that's a pitfall, I think, to fall in, which leads you to the random walk into the...

to basically, and you said it perfectly, it turns you into a consulting firm. And then making these hard decisions and bringing engineering, sales, the executive team together, that's a hard thing to do. What are the, let's say, elements? And what did you actually do in that story? How did you bring everyone together around a common goal and say, look, this is gonna be painful, we might lose some customers.

but we're losing the wrong customers and we're focusing on the right customers that will ultimately lead to the business's success. And yes, it's going to suck for a while, but this is the right thing to do.

Jordan (26:57)
Yeah, I think really it was a function of two things. One was time. So from that point of sort of making that suggestion to actually getting a company mission, vision, sort of really getting toward those guiding things, it took about nine months from there. And so it took quite a lot of time just continuing to build relationships and trust with those stakeholders.

And then having lots of one -on -one conversations to really to really share that view and that perspective that that you mentioned Of you know, here's here's why things feel kind of broken right now Here's what we're gonna see right so showing that I'm not predicting that everything is gonna go great this as soon as we do the silver bullet of You know orienting around this this North Star and deciding that we're gonna, you know grow up a little bit

everything's gonna be perfect, customers are gonna be happy. No, I mean showing that you really understand that there are risks here and there are gonna be consequences to your decisions, but connecting to the big picture. This is what we ultimately care about. This is what we care about for the next year, the next five years, our 10 -year vision. Here's what we really care about. This is how that gets us there. And this is why we can't get there today. And I think really helping people connect the dots there is the biggest key, and especially on an executive level because...

you know, having that understanding of everyone has this shared idea of we want to, you know, with a startup, we want to make a lot of money and either go public or sell to someone. And so what's important there, I think that's what is really shared.