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138 / The Science Behind Building Better Products, with Holly Hester-Reilly

Hosted by Paul Gebel & Sean Flaherty




Holly Hester-Reilly

Product Science Group

Holly Hester-Reilly is the Founder of Product Science Group, a product management coaching and consulting firm that teaches the principles and practices of high-growth product development, and the host of the Product Science Podcast. Holly is a former Columbia University research scientist and has spent over 15 years leading product initiatives at startups, high-growth companies, and enterprises like FalconX, MediaMath, Shutterstock, GTreasury, The Lean Startup Co, Unilever, Fitch Solutions, Capital One, and Weight Watchers.

Holly also teaches at NYU Stern School of Business as well as public and private workshops and has spoken about building high-growth products for events such as Lean Startup Summit Europe, the Women in Product Annual Conference, ITX Product + Design Conference, Parsons School of Design, and INDUSTRY: The Product Conference.

As Holly Hester-Reilly explains, “Intuition isn’t magic. People who have good product intuition know this, because they’ve worked hard over time through lots of hard practice to build it up – and build better products in the process.” Holly is the founder and CEO of H2R Product Science (and a good friend of Product Momentum). We jumped at the chance to catch up with Holly right after her talk at the New York Product Conference. 

3 Pillars of the Product Science Strategy

The product managers who develop this intuition have learned real, tangible skills, benefitting from an evidence-based scientific approach to get there. In her keynote, Holly touched on the three pillars of her product science strategy: 

  • Evidence-based product strategy. A plan for how you will win in the marketplace. 
  • Continuous Discovery + Delivery. Gathering evidence and new learnings with every build. 
  • Empowered teams. Aligned on outcomes, trained and supported with context and tools. 

Product managers, regardless of experience or seniority, can develop their own product intuition by applying the methods embedded in this strategy to learn more about their customers, their market, and their product. Evidenced-based decisionmaking helps validate our assumptions, test ideas, and measure outcomes. 

Holly’s Key Takeaways

We’ve only summarized them here, so you’ll want to watch or listen to catch every nugget:

  1. Not every outcome is equally important or equally uncertain. You need to prioritize the outcomes that matter most to your customers and your business, and assess their risks.
  2. It is not enough to be right; you also have to be persuasive. Evidence strengthens your hand as you seek buy-in from stakeholders and team members.
  3. Practice the Built-Learned-Planning demo. “Planning” is another way of saying what you ‘intend to learn.’

In 2022, Holly Hester-Reilly delivered a workshop and keynote at ITX’s Product + Design Conference. The 2024 Conference features John Maeda, Denise Tilles, Ryan Rumsey, Cliff Gilley, and more. Reserve your seat now.

Paul Gebel [00:00:19] Hello and welcome to Product Momentum, where we hope to entertain, educate and celebrate the amazing product people who are helping to shape our communities way ahead. My name is Paul Gebel and I’m the Director of Product Innovation at it, along with my co-host Sean Flaherty and our amazing production team and occasional guest host. We record and release a conversation with a product, thought leader, writer, speaker, or maker who has something to share with the community every two weeks.

Sean Flaherty [00:00:43] Paul, what a great episode with Holly. She’s an old-time friend of the Product Momentum podcast.

Paul Gebel [00:00:48] Been on a few times. Been at our conference. It’s always a blast catching up with her. What were some of the things that you took away?

Sean Flaherty [00:00:53] This, you know, relationship between risk and how much evidence we should have when we’re thinking about any major decision in the product?

Paul Gebel [00:00:59] Yeah. One thing that was humbling to hear, but always a good reminder, is that sometimes it’s not always enough to be right. You also have to be persuasive. And it’s a lesson that I’m continuing to learn. And I’ll beat my head against the wall until it gets through one day. Holly is such a great scientific mind in the way that she approaches product is really a unique take. I think her voice is really needed in in a space where there’s so much ambiguity today.

Sean Flaherty [00:01:22] Evidence-based. That’s the key takeaway here.

Paul Gebel [00:01:25] Well, really excited to share this conversation with everybody.

Sean Flaherty [00:01:27] Yeah. Let’s get after it.

Paul Gebel [00:01:28] Let’s get after it.

Paul Gebel [00:01:32] Hey everybody. And welcome again to the New York Product Conference. We’re, delighted to be joined by Holly Hester-Reilly really good friend of ITX…

Sean Flaherty [00:01:39] Has been on the podcast before.

Paul Gebel [00:01:40] Absolutely. So glad to have you back. And you just gave a really phenomenal talk about the science behind high growth products and how we can build better practices, evidence-based strategies into the teams that we’re trying to lead. Before we jump into the conversation, can you share a bit about yourself, your background with the folks who maybe haven’t heard of you before and find your work?

Holly Hester-Reilly [00:02:01] Yeah, absolutely. So, I’ve been working in products and tech for I think, 17 years now, but prior to working in products and tech, I worked in chemical engineering research. So that’s why my angle on product is about science, because I actually did academic research for four years, and I published a paper, and I thought I was going to be a lab scientist. And then and then that didn’t work out. So, I fell in love with tech startups, because the pace of it is great, and the energy that people bring to it is so great. And so that just inspired me. Yeah. And I’ve been at home ever since I made that transition. I’ve spent these 17 years, in early-stage startups, in growth stage startups, and then over the last many years, also working with enterprises.

Sean Flaherty [00:02:43] Yeah.

Paul Gebel [00:02:44] So cool. You know, one of the things that I’m paraphrasing slightly from, a concept that you shared, during your talk, is that essentially intuition isn’t some magical thing that just descends from the heavens and strikes us, you know, from, you know, a bolt from the blue. It’s it might be unscientific in the way that we perceive it, but it really is based on evidence-based behaviors. And you talked a bit about how the three pillars of your strategy and your teams start to unpack this, but that that notion of intuition isn’t magic. And I’m my words, not yours.

Holly Hester-Reilly [00:03:20] I agree.

Paul Gebel [00:03:21] Can you talk a bit about more what you’re sharing in how we can make these more deliberate instead of accidental practices in our, in our teams.

Holly Hester-Reilly [00:03:29] Yeah. So, I think, you know, very much I agree, intuition is not magic. And the people who have good product intuition, they built that up over time through lots of hard practice. They learned real tangible skills with science behind a lot of them. And so, the things that I think about are the science of human behavior. You know, the way that a human interacts with technology, I think about the science of organizations, you know, management of organizations and how organizations work. I also think about complex systems and information flow. So, there’s a lot of different places where this comes out. And I just think that, you know, there’s so much that we can think critically about and write down and teach it.

Paul Gebel [00:04:12] Well, we’ll talk about this more in a little bit. But just to cap this thought off, I think, you know, if we’re learning, if we succeed by accident, we should stop and pause and figure out what is it that we learned.

Sean Flaherty [00:04:22] Yeah, exactly. One of the things I loved about what you said was it’s not enough to be right. You also have to be persuasive. And that’s one of the things evidence does for you, you know. Yes, there’s a huge shift in lots of different industries towards evidence-based everything, right?  And I think building it in from the front, right from the beginning, it’s important. It’s an important and helpful tool because it also makes you more persuasive. So, if you know why you were successful you can explain it with data. Yeah. Everybody wins from that for sure.

Holly Hester-Reilly [00:04:51] Yeah. Yeah. And I mean, to be honest, I honestly think like after I’ve worked with so many startups, I think that all startups’ successes are a mix of skill and luck.

Sean Flaherty [00:05:03] A little bit of being in the right place at the right time.

Holly Hester-Reilly [00:05:04] Little bit of that, you know, and looking back on why the companies that were successful were successful and trying to use that hindsight to develop, you know, foresight for the future is so valuable.

Sean Flaherty [00:05:16] Yeah, yeah. I also love the concept of the making sure with every sprint you’re building that we’re learning.

Paul Gebel [00:05:22] I was just about to go there.

Sean Flaherty [00:05:23] How are we not always doing that? Once you see it, you cannot see it, right?

Paul Gebel [00:05:28] I think I wanted to ask and this is maybe putting you on the spot a little bit. A little bit of a stickler for verb tense. I notice that you specifically phrase it as in every sprint, we should be cataloging what was built. What was learned? Yes. And what are we planning? Yes. And I’m curious if that was deliberate. If those verb tenses have a deeper meaning or am I reading too much into that.

Holly Hester-Reilly [00:05:51] Oh, that’s really fascinating. This might be a case of me having an intuition around it and not having, you know, thought it through time.

Paul Gebel [00:05:58] Real-time discovery. Here we go.

Holly Hester-Reilly [00:05:59] But I think, you know, it is very much like when we sit down to do the Built-Learned-Planning demo. I feel like what we built: happened. What we learned: happened, and what we’re planning is, like, in progress, right? To me, it’s like it’s not done right because it’s ever evolving.  And so, I don’t want to talk about what we planned. I want to talk about what we’re planning.

Paul Gebel [00:06:19] Where my mind went when you shared that was immediately, you know, the process sticklers which we need – this is not a disparaging remark. We need scrum masters. We need project managers. We need those rigorous analysts in the system. But I think when all we’re doing is taking temperature and tracking burn up charts, we end up losing sight of where are we going in the future? It’s all about, you know, kind of the poor implementation of OKRs. It’s all part of this kind of kind of self-defeating cycle with the best intentions, but it becomes a self-defeating cycle.

Sean Flaherty [00:06:50] Well it’s not you’re trying to follow a prescription, but you’re if you follow the prescription, you’re not really going to learn anything.

Paul Gebel [00:06:56] And should give you a path forward.

Sean Flaherty [00:06:58] I also love that you said making sure that you’re learning. It’s like you’re creating a forcing function for it.

Holly Hester-Reilly [00:07:03] Exactly.

Sean Flaherty [00:07:04] Which for me, when I think of the planning piece. So what you built, what you learned, what you’re planning is going to now intuitively include what you intend to learn next. What do you scientifically include?

Holly Hester-Reilly [00:07:18] That’s the word. Yeah, exactly. But that’s exactly. Yeah. You’re going to plan what you want to learn and what you want to build, not just one or the other, you know. And so you should have a learning plan.

Sean Flaherty [00:07:29]  I love that.

Paul Gebel [00:07:31] Yeah. I think where that, where that came the point that you ended up making that I thought was a really great cap on that idea was don’t tell teams what to build, because then you rob them of the chance to explore and discover and create this sort of creative energy that only comes from open-ended questions and sometimes ambiguous challenges that they need to overcome. If every user story has acceptance criteria and test cases and everything written down and fed to the team on a silver platter, they might be operationally efficient, but they’re killing their own creativity.

Holly Hester-Reilly [00:08:04] Exactly. Yeah. And that’s not that fun. It’s not really a fun way to work.

Paul Gebel [00:08:09] You know, the Outcome-based Roadmap is one that I’ve adopted. And, you know, every product needs its own flavor roadmap. I’m also a big fan of the Now-Next-Later and Problem-based Roadmap. So, it’s kind of adapted to the problem at hand. But one of the things that I really liked about the time is that I’ve, I’ve leaned into the Outcome-Based Roadmap is that it enables a lot clearer cause and effect. Which other types of roadmaps tend to be more planning focused. And I think, you know, one of the things that that is really clear in the way that you’ve organized this strategy and approach to product management is not every outcome that that we think we have to address always has to be one that we end up adopting. You kind of tied this into it’s very expensive to learn which assumptions are wrong after delivery. Right. And I think one of the things in an Outcome Based Roadmap can address is getting ahead of those assumptions.

Holly Hester-Reilly [00:09:03] Absolutely. And you don’t always know at the beginning. You know usually you can find some outcome that everyone can agree is important. But you probably have some hypotheses about some outcomes that you’re like, I think this matters to our customers, but I don’t actually know for sure yet.

Sean Flaherty [00:09:17] Until you test it to put it market and test it. Yeah, none of us really know. Yeah, that’s the truth. One last insight I got from your talk was this relationship between how risky is the problem here, how risky is it and how much evidence do we have?  And the concept of one-way doors versus two-way to understand if it’s a one-way door, really. And it’s a risky decision to make, we really better go gather some evidence. And how often do we just take a stab at the dark? And just build something and then see what happens? I just thought that was a useful way to think about what decisions require evidence and which ones, you know, can we maybe just go try.

Holly Hester-Reilly [00:09:52] Yeah. Exactly. And you know, companies tend to fall, I find on one side of the spectrum or another where either they over index on research and they don’t build enough, or they over index on building and they don’t research enough. And I really think it’s a balance depending on the decision.

Sean Flaherty [00:10:06] Yeah, absolutely. Even within a given product team or a given. Yeah. Ecosystem for sure.

Paul Gebel [00:10:12] So we just have a couple of minutes left. I want to I want to ask a practical question about how, you know, there’s, an early career product owner or product manager maybe hasn’t developed that influence or persuasiveness as you spoke about as well in the organization. And they’re trying to make their way and build out some, some rapport, build some team dynamics and trust within the organization. How can somebody early in their career begin to develop these skills? What are what are some ways that, you know, the organization might not be set up for this kind of wholesale re readjustment or reapproach? What are some small ways, practical ways that people can take back to their teams and start to address these problems that you’re talking about?

Holly Hester-Reilly [00:10:52] I mean, I think the first place to start, if you’re on a team that’s not really set up for this, is really to do some kind of small discovery research. And if you cannot get like permission and space for that, then you can even start with like interviewing people, you know, that, you know, who have guerilla marketing. Doing something like that, you know, you can talk to, you could reach out to people on LinkedIn who, you know, maybe you don’t get permission to do it, but you just say, well, I’m going to have a conversation and it’s just a conversation, right? For coffee, you know? And then you bring back those learnings and you sneak them into your sprint demo.

Paul Gebel [00:11:28] Yeah. Love that.

Sean Flaherty [00:11:29] Love it.

Paul Gebel [00:11:30] Well, Holly. It’s been a blast catching up with you it’s fantastic to see you sharing all these ideas and really moving the product community forward. Thanks so much for taking the time. Before we let you go, how can people get in touch with you? Where are some good places to track you down and learn more from you?

Holly Hester-Reilly [00:11:45] Yeah. So the and the Product Science podcast and you can also find us on LinkedIn.

Paul Gebel [00:11:51] Absolutely awesome. Yeah. Thanks for taking the time.

Holly Hester-Reilly [00:11:52] Thank you as well. I’ve had such a pleasure every time I’ve worked with you two. Yeah, it’s been great. Yeah. Thanks so much. Thank you.

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