How to Accelerate Strategic Impact at Scale

Beyond product excellence and engineering efficiency, one critical yet often overlooked driver of strategic impact is Strategic Portfolio Management (SPM).

In this interactive Ask Me Anything (AMA) session, Aaron Hall—CARFAX’s VP of Portfolio Management and MBA Adjunct Professor at Virginia Tech—shares insights from his extensive experience leading enterprise portfolios, covering:

🔹 The role of Strategic Portfolio Management (SPM) alongside Product & Project Management

Each one brings unique strengths to the table. SPM looks at whether strategic goals are met—thinking about priorities, investments, and the big picture—while Product Management zeroes in on offerings that solve customer needs and remain competitive. Together, they ensure teams deliver the right solutions at the right time.

💬 “I look at [portfolio, product, and project management] as distinct, but quite complementary. If an organization is phenomenal at one, without the other two, it’s going to be sub-optimized. You’ve got to have a strength in each.”

🔹 Best practices for implementing SPM effectively

Start with clear communication and a simple process. This ensures everyone understands each change, reduces confusion, and builds momentum.

💬 “We started manually…define a process, get it going, get some feedback…before looking at a tool.”

Pick a best-of-breed solution like Dragonboat, that supports and enables your ongoing transformation journey.

💬 “We tested a lot of heavier tools, but needed something that wouldn’t force us into one way of working…Dragonboat gave us just enough structure to unite product, project, engineering, and design—without burying us under features we didn’t need.”

🔹 Tips and real-world examples on defining, delivering, and adapting strategic plans amid change to drive business transformation

Change never stops. Regularly check that each project still aligns with current goals. If not, pivot or stop so you can focus on what matters—even if it’s a tough call.

💬 “We have a living, breathing organization…we have projects in flight. We’re flying one plane while building another.”

Hosted by Dragonboat’s founder & CEO, Becky Flint, this is your chance to gain expert insights from two Product Portfolio Management Leaders. 📺 Watch the recording and access the full transcript.

Key Takeaways

1. Strategic Portfolio Management is ongoing and flexible: Aaron shared that it’s essential to keep adjusting initiatives based on market changes, resources, and business goals. It’s not about reaching a final milestone; it’s about continuously adapting to stay aligned.
2. Integrated operating models drive success: CARFAX uses a structured approach—the “Jeopardy Board”—to align executives and cross-functional teams, letting them add or pause initiatives based on strategic priorities.
3. Agile delivery and strategic planning complement each other: Both rely on clear communication, feedback loops, and visibility across teams.
4. Choosing the right tool for your process is key: Aaron explained why CARFAX chose a best-of-breed solution like Dragonboat after first defining its goals and processes. Instead of forcing a single tool to handle everything, they picked a platform that supports and enables their ongoing transformation journey!

Transcript

The following transcript has been altered for readability.

Welcome and Session Overview

Becky Flint: Welcome everyone to the Product Operating Excellence Mini-Series, hosted by Product Ops HQ and sponsored by Dragonboat. In today’s session, we will cover How to Accelerate Strategic Impact at Scale in an “Ask Me Anything” session with Aaron Hall. 

My name is Becky Flint, and I’m your host today. I’m the founder and CEO of Dragonboat. For some of you who are not familiar with the Dragonboat, it is an AI-powered platform for product leaders to accelerate strategic impact across your product operating models. It is adopted by many leading companies, including Aaron’s current company, and we are excited to not only provide software but also to be your partner and offer a community where we can all learn, improve, and get better at driving and accelerating strategic impact.

Introducing Aaron Hall, VP of Portfolio & Project Management and Chief of Staff at Carfax

Becky Flint: With that, I want to properly introduce Aaron Hall. Aaron is the VP of Portfolio & Project Management and Chief of Staff at Carfax, and he also teaches in an MBA program as an adjunct professor at Virginia Tech. Carfax is part of S&P Global, a company listed on the New York Stock Exchange. We will hear more from Aaron about that in a couple of minutes.

Aaron has a diverse career in leading large organizations. He is currently running the entire portfolio delivery and best practices at Carfax, and he has also previously led large organizations and programs at Stride/K12, AOL, and NeuStar. Aaron is a retired US Army officer who served for over 20 years in aviation and engineering, bringing a rich background to driving business impact.

And last, but not least, Aaron is a certified Project Management Professional (PMP) through the Project Management Institute (PMI), and his team was nominated as one of the best in program management. Sorry if I got that wrong, Aaron; maybe you can clarify a little more, but I definitely saw somewhere that your team was recognized by the PMI organization. Without further ado, please welcome Aaron Hall as we begin our conversation on how to accelerate strategic impact through portfolio management and other great insights.

Carfax’s Story

Aaron Hall: Good morning, Becky, and hello to everyone watching. It’s great to be here with you all. I assume it’s morning for most, and I’m happy to share a bit about our story. 

I thought I’d start with some context because we have been on a journey towards effective strategic portfolio management. Honestly, I think all of us are on a journey towards that—I’m not sure you ever get there. Don’t get me wrong, and maybe the marketers at Dragonboat would say, “Hey, Dragonboat can get you there,” and I think it can. I just think, in general, conceptually, practically, culturally, doing strategic portfolio management really is a journey, and we’ve been on an interesting one. 

I’m hopeful that most of you are familiar with Carfax—perhaps you’ve seen the fox on TV. But I wanted to start with our mission real quick, because this is what drives us. We are all about helping millions and millions of people literally every day shop for, buy, service, and sell cars.—that’s a pretty stressful endeavor. We have labored for the past 40 years to establish ourselves as the global leader in providing vehicle history and information that helps consumers. Over those same 40 years, we built a great set of industry partners, including car dealerships, service shops, banks, insurance companies, law enforcement agencies, and more, on the B2B side of the house. We do business throughout the world. I’ll focus mostly on our U.S. market today, but we also operate in Europe, Canada, and Mexico. 

I think the most interesting thing about portfolio management for us is that literally half of our staff is directly involved with product and technology delivery. Whether we do portfolio management well or not, we’re touching a lot of people’s lives. And the other half is affected indirectly by what they can market, what they can sell, and what they can collect revenue on. 

These are some important statistics about our positioning in the marketplace. Like I said, we’re just over 40 years old. For the first 30 years, our focus was like a laser beam on vehicle history—gathering data, making it available to consumers, establishing ourselves in the industry, and really helping consumers through the purchase process. For many of us, buying a home is crazy and stressful, and buying a vehicle can be just as challenging, followed by dealing with all that comes next.

In the last several years—or, to put it another way, in the more recent period—we started to view the automotive process as more of a life cycle. If you look at that blue ring on the outside, most consumers are in one of those phases: either shopping for, buying, owning, or selling a vehicle at any given time. And the many questions in the bubbles around that ring reflect what consumers often ask. We recognized that there are tons of questions consumers have. 

So, we set out to build powerful products and capabilities that answer these questions—whether it’s knowing which vehicles are available, when to service a vehicle, how to sell one, or what a vehicle is worth. For the past eight to twelve years, we’ve been focused on building very focused products and many sub-products—around 40 different ones—that ladder up to these orange items, leveraging what you can see in the center, our core product, delivery, availability, and the trust and strength of our neutral consumer brand, and then the partnerships we have across the B2B space, and of course, our great culture. We’re going to come back to Carfax’s culture a few times today. We combined all these elements and remained laser-focused on building dedicated teams that were really effective at developing these focused products. 

But here’s the key: as we moved into this decade—post-pandemic, really—we began to realize that the time for building isolated, discrete products had passed. Instead, we needed to integrate those products and create a lifecycle capability—a suite of integrated products that helps consumers, even if they don’t yet know they need it, move smoothly through that lifecycle. As you can imagine, our initiatives and our business became much more complex. We had to shift away from a discrete delivery and decision-making model into a much more integrated, and frankly, more complex, decision-making and delivery model, which is what really has driven our march down the path toward more strategic portfolio management.

I hope this gives you a bit of context about our business, our journey over the first 40 years, and where we’ve been over the last 2-3 years. And ultimately, we’re still working through it today. As I said, it’s a journey—and we’re on it.

What is Strategic Portfolio Management (SPM)?

Becky Flint: It is a journey. It’s definitely a journey. Thank you so much for the context—I really appreciate it. You mentioned many interesting topics, so I want to start with a question on strategic portfolio management. How do you think about it as your organization moves through this journey? As your company grows and breaks down the process of buying cars into many pieces, how do you think about strategic portfolio management? I also know you teach a class on project and portfolio management, so I would love to hear your thoughts on its evolution and how companies operate in that context today.

Aaron Hall: Yeah, that’s a great, great question. It’s funny—the first two words that came to my mind were “art” and “science.” Every time I discuss portfolio management, I usually say it is the art and science of continuously selecting and managing the optimum set of projects, programs, or initiatives that deliver maximum business value, and hence allow us to achieve strategic objectives.

I mention “art and science” because I believe many organizations look for a formula or a set rubric, some mechanism. For example, some might send an email asking for an executive vote, and if the votes exceed 37, they proceed. Some organizations do that, and perhaps it works best for them. For us, there is both a scientific component and the art of conversation—recognizing that our organization, as well as our business, is a living, breathing entity full of human beings who have different experiences, different risk tolerances, and things like that.

But we want to make sure, so we are focusing on four key questions as we progress along this journey:

• Are we investing in our products and platforms at the right levels, in the right way, and at the right time given the market dynamics?
  
• Are we working on the right projects?
  
• Are we applying our resources correctly, and do we have the right number and types of resources?
  
• Are we responding dynamically to changes within the organization and in the market?
  

It’s a mechanism to enables us to answer to those important questions.

How does SPM operate alongside Product & Project Management?

Becky Flint: Right. You mentioned many interesting topics. Traditionally, people often think of product management and project management as separate areas, and sometimes there is even a stigma attached to the term “project management” these days. Many also view portfolio management as something new, even though it’s not new for us have been practicing it our whole career. So, how do you see the evolution of product management, project management, and portfolio management? Sometimes we even come across titles like “product operations” today. How do you see these terms evolving and fitting into your current operating model?

Aaron Hall: That’s a good question. For you and me, there’s a clear distinction between these roles. However, many people tend to lump anything that starts with a “P” and an “M” together. I look at them on the one hand very distinct, but, on the other hand, quite complimentary—almost like a three-way yin and yang—they complement each other. I truly believe that if an organization is phenomenal at one, without working on and having a capability in the other two, it’s going to be sub-optimized. In the short term, it might generate some wonderful things, let’s say some outputs from the entity, but over time, you have to have a strength each.

So if I look at portfolio management, I think about, “Are we meeting the organization’s strategic goals?” There are many other aspects to consider there. On the product management side, the focus is on whether our offerings are competitive—how we price, position, and package them, what feedback we receive from customers, and how our features and capabilities evolve. Finally, at the execution level, program and project management focus on whether are we tactically executing our projects effectively. And those projects are driving the evolution of our products and platforms right to deliver value.

I want to be careful. I know we may have some Project Management folks with us, and you know, I’m a PM. Sorry, I did it. I’m a project manager at my core but I don’t mean to imply that project management is tactical, while the other two are not. Just relative to portfolio management. I think portfolio management is much more of a strategic activity than the other two, which are probably more in the operational and tactical dimension or paradigm.

How did you evolve your organization to integrate multiple roles—where team members use a blend of project and product management skills—to drive strategic portfolio management within your operating model?

​​Becky Flint: Right. Very interesting—the way you describe these roles, I 100% agree. In many cases, one person may play multiple roles. We all use some level of project management skills, whether we are C-level executives or have titles like project manager. As we move up to more executive roles, our decision-making broadens, and product management becomes part of our overall skill set. For example, the conversations we have and the talks we give are themselves products that educate our customers or users. These skills are extremely valuable. You can’t just have a good strategy or a good product if you fail in execution. Before we dive in further, you mentioned the triangle as an analogy. I’d love for you to share how you evolved your organization to have these different roles work together in the context of strategic portfolio management and your operating model.

Aaron Hall: Yeah, that’s a great question. At Carfax, we’ve long used what we call a “boat model.” Originally, we actually called it “The Triangle.” Years ago, one of our engineering leaders and I were discussing how to make our delivery teams more effective. We stood at his whiteboard and drew three roles. We said that for a team to deliver, you need strong and aligned product, project, and technology leaders. All three have to be competent, and aligned. And they have to have a bond, it’s got to be trust-based to lead the team forward.

We drew a triangle around these roles, but we realized that the name “Triangle Team” didn’t sound very inviting. Around that time, I noted that design plays a key role in our projects, so we expanded our model to include design, forming a box with four key leaders: product, project, design, and technology that have to be working together. Interestingly, the triangle remained just above the box, looking much like the bow of a rowboat. We thought, “Aha! That looks like a boat.”. The idea of these 4 leaders rowing in a boat on a body of water in the same direction, at the same pace, to keep us moving forward versus zigzagging all over the lake, was simply too good to resist. Over the past 8-9 years, the boat metaphor has really taken off, and it’s a wonderful connection to Dragonboat, given the iconography and intent behind your name.

How do strategic planning and agile organization operate together?

Becky Flint: Exactly. That’s definitely our intent—everyone rowing in the same direction—because it takes more than one function and one skill to move the organization forward. Often, people focus on one area, like engineering or product management, or even go-to-market strategies. But if you don’t put everyone together, you could build the best product that nobody buys, or the best roadmap that the engineering team can’t deliver because one team has resources while another doesn’t. We really have to tie everything together. 

As you mentioned earlier, Carfax is a very large organization that has evolved significantly, breaking the core product into multiple pieces, so we see a lot of the organization is involved. You have agile, empowered teams—so how does agile work alongside strategic planning and strategic portfolio management in your organization?

Aaron Hall: Yeah, that’s a good question. For the last 15-16 years, one of the biggest challenges I’ve had is explaining to people that dynamic but structured strategic planning—whether it’s at the enterprise level or all the way down to the tactical level where projects get executed—can and do actually work quite well together along with agile project, product, and technology delivery. I think a lot of people are zealots: they think agile is all about iterative, fun, no planning, and no documentation, which isn’t really true. It’s just that agile values certain things more than others.

I firmly believe these two are not polar opposites; they can and do co-exist quite well. This is a great source of debate in the MBA class I teach. People who are coming, they’re just hardcore project managers, and they think agilists are, you know out to lunch and full of it, and vice versa, by the way, so we have some really good spirit, good debate there, but I’ve had a lot of it in the workplace as well. 

At Carfax, we’ve developed our software in an agile manner for probably 10-12 years. Even before we really got into strategic portfolio management, our strategic planning already worked in an agile delivery context. It mostly came down to how many teams we had and how those larger teams functioned. If you think about the smaller sub-product teams I mentioned earlier, they were effectively kind of portfolio, managed or optimized from an investment perspective based on having dedicated teams and the size of those teams because that equates to money, which is the investment the company puts into the machine. The transition to a more integrated lifecycle strategy in the past several years prompted us to pivot away from persistently dedicated teams. We’re still in the middle of that shift—or perhaps on the tail end.

One concern I’ve heard repeatedly is about esprit de corps. Some worry that by shifting away from dedicated, highly focused product delivery teams, you lose the bond that forms around a particular product or platform—the tattoos, the theme songs, and so on. My view is that it doesn’t really vanish. In some cases, focusing on projects can increase esprit de corps, and a more flexible staffing model, led by the portfolio management intent, can create different phases or types of team spirit. Concluding a project, for example, can bring a sense of excitement and accomplishment.

It’s been an interesting transition for us, and to be clear, agile delivery and strategic portfolio management aren’t the same. But they share foundational principles such as communication, transparency, iteration, and a willingness to seek feedback. Both rely on having conversations rather than rigid formulas or plans. At the end of the day, strategic portfolio management is about being flexible with one’s business as things change in the marketplace. On the agile side for you to be successful and agile, you’ve really got to be flexible and agile up and down the organization, meaning inside and outside of your development teams. That same agility is going to benefit you from a strategic portfolio management perspective as well. So I think there’s a lot more in common than most people think.

Carfax’s “Jeopardy-Board” for Product Operating Model

Becky Flint: I 100% agree with you. Over the past decade or so, across various companies and different levels of operational maturity, I’ve observed a few important points. Whether it’s strategic portfolio management—which drives business outcomes—or agile product development—which focuses on customer and business outcomes, you shouldn’t fall in love with the functions or group I’m in. If you only remain in one efficient “production machine,” it becomes a sort of a peanut buttering your portfolio because you have this dedicated team doing the same thing right? It’s definitely not the best.

The other critical aspect is strategic agility, which involves solving problems on a bigger scale. Agile practices fit within this umbrella of strategic agility, meaning teams must shift as needed. For example, look at what happened, OpenAI happened, and everyone is shifting their business. If you don’t, I think your days are numbered. Right? So it’s just the reality that we operate is you don’t just agile at the local team level. You have to be agile at the portfolio level. That means the strategy will drive what problem the team is going to solve. It could be the tattooed thing, or it could be something else but we really should be falling in love with the problems we try to solve, and then this piece of whatever wedge or whatever things we’re going to build right? So I think that really coming together nicely.

Of course, this becomes hard and complex in larger organizations. Scaling beyond a couple of Scrum teams in Jira. Early on, when our team first talked to yours, there was a well-known Jeopardy-style diagram that actually looked very similar to the product operating model. Can you explain what that diagram is, why it’s important, and how you use it?

Aaron Hall: Oh my goodness—I call it infamous! Let me tell you: I’ve had several moments in my career where I did some brainstorming on something on this whiteboard behind me, and one of our C-level executives came by and said, “Hey, what is that? That looks really good. Can you make it portable and presentable and bring it to our executive conference room?” I have a long-time colleague who sits right outside my door, and she’s gotten a kick out of that more than once.

But there’s really no rocket science behind the Jeopardy Board. It’s basically a color-coded, functionally tagged depiction of the major changes we needed to initiate and manage collectively in order to implement strategic portfolio management at Carfax. One of the most common things—and you might notice our Carfax playbook behind me—is that if you search for “Carfax playbook,” you can find this artifact. It’s a wonderful depiction or representation of our culture that we truly embody, and it is a very having worked a lot of places. As you said earlier, we have a very different culture there.

Transparency is key within our culture, and I’ve openly acknowledged that the amount of change that we are bringing to the organization is probably too much. More than once, I’ve admitted that. These changes are interconnected, though. We needed a clear set of strategic objectives, with an articulated problem that the business is trying to solve, along with three or four significant value-driving initiatives associated with them. That’s fundamental. By the way, I’d say that’s even pre-portfolio management—that’s about business strategy, and then the portfolio management process picks it up and goes.

Just going through that exercise was challenging, and it’s still going on—it never really stops, in my opinion, that’s ongoing, and that’s just one piece. Establishing a common delivery lifecycle with defined roles and responsibilities once we get into execution is another. Then there’s stopping the projects that don’t align with the business strategy, which can be tough. And by the way, I’m not a traffic cop, but sometimes I do feel like a crossing guard right? And my sign doesn’t say, stop, I turn it around. My sign says slow. And I’m like, “Okay, guys, let’s just make sure that this thing that you’re trying to either start or make sure continues truly is aligned with that objective because it doesn’t sound like it to me.” But I don’t get a vote. I mean, I think that’s an interesting part of this discussion, too. My role is one of neutrality, I am not advocating in one way or another. Don’t get me wrong, I want to see the company move forward and be successful. 

But these are just 3 or 4 different. Probably there were 12 or 15 items, Becky, that we had to move forward together. Capacity management, a whole new view into what people are doing and how they’re doing, classifying our work in a different way, and so it was simply a way for me to share, but then also maintain a view of where we were on the paradigm across each of them, and then ultimately overall.

Transformation & Tooling at Scale – Why Dragonboat?

Becky Flint: I think you’ve raised so many key points, we could probably have three sessions just on those topics. But one key thing is that people are proud of their work, and you know, regardless of the sort of tattoo on your team, or in the case, the projects or initiatives going to stop and then go. It is difficult to see it locally because people make optimization decisions based on the information you have. But when you take a step back, and look at portfolio level all of a sudden, this that seems to be a good idea in the beginning, may no longer be a good idea because things changed, or this became a much bigger effort. So you make the effective decision at any level – executive and the team level – to say, “Is our thesis still correct? Are we still investing? There’s something new coming around?” 

And the only thing that’s not changing is the change itself, right? Everything is changing and changing very fast, this changing faster and faster in this world. Let’s talk about it. Let’s talk about transformation. You mentioned it’s a never-ending journey that keeps evolving, just like the world around us is evolving. Let’s also discuss tooling. With an organization of this size, and the speed of so much change, many people are involved. I know you chose Dragonboat after a thorough evaluation—that’s not a small decision. I’d love to hear more about how you think about it, about tooling itself, what checked the box, and why it’s important.

Aaron Hall: Yeah, another great question. First and foremost, we don’t start with the tool. We just don’t. I’m not ashamed to say that every time we’ve identified a need for a new process at Carfax—over the last ten years—that I knew would ultimately be enabled and automated and optimized by a myriad of tools out there, we started manually. That meant a lot of Post-it notes, Excel, and PowerPoint, and that was OK. Whether it was portfolio management or basic roadmapping day-to-day projects or work, management, etc, we found it really effective. Define a process, get it going, and get some feedback on it before looking at a tool. Because I don’t want to zoom in on a tool, find one we like, and then have to bend our process and our culture into the tool. 

And I’ll tell you the other thing that’s interesting for Carfax, and we haven’t had – I got to give credit to our CIO, I haven’t had this freedom elsewhere – we have definitely taken a best-of-breed strategy, not one that’s driven by a single company or brand who’s built a tool or an enterprise strategy to all be on one platform. And of course, this brings some interoperability and sometimes cost-efficiency challenges but I really believe that best of breeds approach has served us well.

If I think back to our path to beginning to work with your team and leverage Dragonboat over the last year, we looked at a lot of tools in the portfolio management space, no doubt. Many of them were much heavier, much more integrated, and really intricate insights and analytics. But at the end of the day, our culture is not one that requires nor would it tolerate all of the governance and administration associated, or required really for all the work. 

We needed enough of it so that we could integrate with Jira, deliver really engaging visualizations, some of the great views that you guys have, the capacity management I mentioned earlier, but we also wanted to find an organization like yours, that had a great culture that matched ours, that was growing, and that we could grow along with. That was all really important to us.

I should probably mention, that we’ve also had sunsetted tools just in the last 10 years that I’ve been here, even ones that I brought into the organization, and I don’t look at this as a failure. I think of this as a journey. If you think about being agile and iterative, as our maturity has grown and the complexity of our business, we recognized some of the tools that made sense for us in the 2010s just don’t make sense for us in the 2020s. So let’s make a conscious decision and move on.

Change Management: Best Practices for Large-Scale Transformation

Becky Flint: This is super insightful. Someone in the audience raised their hand—please type your question in the chat so I can catch it, as live audio can be tricky for the host. Meanwhile, I want to circle back to something you mentioned about transformation involving people, processes, and ultimately technology, not the other way around. You don’t choose tools before the other things, I really appreciate that.

So, a question we often hear is: What are some of your change management best practices for large-scale transformational change? How do you handle change at a big scale?

Aaron Hall: Yeah, I’ll throw in a couple of things that come to mind. One is to communicate early, communicate often. It sounds like a little cliché but one of the downsides or the tricky parts of that is, when you’re talking to folks early, you don’t always know everything. I’m a pretty honest guy, and I want to be transparent with folks. I’ve done this with my team, with our engineering leaders, and with our executives. I know where we’re going to, I have a plan for how we’re going to get there but I can’t tell you each step, each day, each hour of how that’s going to unfold. And part of that is because I think there’s more value in getting going, and getting some feedback, and then charting the next course. I mean, it’s almost like sprinting, to be honest with you. But I think your organization has to be willing to accept that, and some organizations really want to know exactly how and when are we going to get there.

Another point—also a bit cliché—is to know your audience. When I’m sitting down with my PMO folks and talking through things with them and hearing their challenges and pain, I’m having a different conversation than when I’m our executive conference room talking with our C-level folks. It’s not that one is better, different, or smarter than the other; the problems and the challenges are different, the tolerance for jargon is different, those types of things. For example, I don’t refer to Dragonboat as Dragonboat with our C-level folks. It’s our portfolio management platform, and sorry for your marketers, if that makes anybody upset, but the reality is, it makes them scratch their heads because our Head of Marketing and our CFO don’t really get it, they can’t make the connection. But we first started talking about portfolio management, I said, “You guys all have a 401(K), right? That’s a portfolio, and your investment decision-making is exactly what we’re going to do here. We just need to identify the parameters, and how often we’re going to look at it and so on, just like you do with your own investments”.

Overcoming Challenges to Accelerate Strategic Impact

Becky Flint: Super helpful. People sometimes forget that every Scrum team has about 5 people, we’re easily talking about a couple 1 million dollars. If you have a 10 scrum team, how many 1 million dollars we’re talking about just the cost alone, not the opportunity cost and not the application. Just people cost alone, let alone the surrounding people around it. That’s definitely portfolio management, if we don’t have a broader view on where it goes, then it could go to things that are not driving the most important impact. And in today’s world, so competitive, and fast-changing, if we’re not making the most important impact then we would be losing opportunity and/or losing market share–so in both cases, it’s not good. 

So, one question we hear a lot from customers is: What are some of the main challenges or lessons you’ve learned about accelerating strategic impact?

Aaron Hall: Well, on the challenges front, let’s just get it out on the table: change is hard. I’ll own it, I’m not great with change—my wife will tell you that first—it’s hard for everyone and all organizations, no matter how you look at it. It might be easy for you but tough for someone else, and acknowledging that is key.

If I go back to what I said when we were talking about the Jeopardy Board, too much change can be too much. We’re actually having a pretty spirited debate right now with one of our C-level execs around one of those jeopardy board components, and whether we should pull it back. I’m definitely on one side of that debate, and he is on the other, and one of my directors is right in the middle trying to get us to come together, and I don’t want to come together. I’m just sharing that with you guys to be transparent because it’s hard, and I may have to give, even though I don’t particularly want to, and I’m not being personal about it, I just don’t think it’s in the best interest of the company but I may not be right, I don’t have a trump card to play. So I think those are certainly some of the challenges.

Another thing, I don’t know many organizations that can stop the trains for 30 or 60 days, figure all this stuff out and start from scratch. I can’t tell you the number of times I’ve said, “Hey, team. Let’s just pause for a minute. If we all showed up tomorrow, all 50 or 5,000 of us, or whatever, and said, how should this work? We could chart the course right? We could put the tools in, we could put the processes in and we would get going.” But the reality is, we are a living, breathing organization, we’re taking revenue in, we’re spending money on a whole bunch of different things, we have projects that are in flight. We are flying a plane while we’re trying to build another. How about that? We’re building a second plane in the air while we’re flying a parallel one, and that’s tricky, that is hard. So again, deep breath every once in a while, there’s not coffee in this cup that gets me through some of the weekends, evenings, maybe, definitely, a lot of challenges there.

Leading organizations in various industries and eras: what’s changed in the last decade, and what remains the same?

Becky Flint: This is very interesting. I want to add a little bit of color from my experience, as well. Change is very difficult, and it’s a long journey. One of the key things is to show people the progress you’ve made because then you actually can get people continuously engaged onboarded. So, how do you show people what you’re getting? When we started Dragonboat, we had a complete product operations platform that cover strategy, roadmaps, intake capacity management, PDLC, and delivery orchestration, and some companies were just not ready to take all of that. The Jeopardy Board is an example. What we found out is that, regardless there’s a baseline–visibility. People want to know where we are, people want to know where we’re going. Now we are starting to see more companies say, “Hey, we are not ready on all the other stuff, but we’re ready to see where we are today in terms of our portfolio.” We call it “Portfolio Intelligence”: You know where you are today and then link to all the different data and systems, so you know where you are today. And then from there, you can say, “Okay, now we can add other capabilities”. 

As we’re discussing this, I’d like to hear more from you, Aaron, about what’s changed over the last decade or so, from your observation, as you’re teaching the MBA class and also moving from different types of companies and industries and practice, into the world we are today. Then we can talk more about the Jeopardy-like Board, as well.

Aaron Hall: Yeah, it’s interesting. You mentioned the different companies I’ve worked at. One of the neat things about my profession of project, portfolio management is that it’s very portable. If I look back on my career, whether it was the time I served in the Army or worked with the Federal Government as a civilian, and whether I was in the telecommunications, internet, education, or automotive industries, a lot of the needs are quite similar. The context changes but the function, the needs, the worries, the challenges, are very similar. 

Before Carfax, I was at a great company called K12, and probably one of the most passionate organizations I’ve been part of. It was full, at the time that I joined, of really experienced and academically credentialed leaders, focused on making super high-quality products for kids who go to school virtually, which is wonderful. I had young kids at the time, and I was very passionate about it as well, but portfolio management is very tricky in that space. Getting to a decision based on a composite view of the organization’s goals as opposed to solely making decisions based on the educational impact of an investment, was really not a popular approach. I definitely had some headwinds. 

Another key differentiator is where each organization is on its growth curve. When I joined Neustar way back in the day (the old Neustar, not the current organization today) we had just spun off from our legacy parent company and gone public. We had a lot of capital, we were in big-time growth mode, and we were trying to demonstrate to everyone we were a viable standalone entity in business. That was very different than when I was at AOL, that little internet company you may have heard of. By the way, I didn’t get rich off of AOL. I joined after its heyday, and lived through the Time Warner acquisition. It was not a merger, it was an acquisition where we purchased them, and ultimately, through the begin of AOL’s decline. You might not say that AOL was as mature as General Electric, or Verizon, or whatever, but it was rather mature as far as strategic investment, decision-making, and much more so than Neustar. So the dialogue was different. I think a lot just depends on where an organization is on its growth curve.

Visibility – Your key to accelerating strategic impact at scale

Becky Flint: That is so cool. We hear this a lot in what we call a product operating excellence maturity curve. I want to highlight here that every company has a strategy and outcomes, as you mentioned–like K12 may have a different strategy because they focus on different outcomes versus AOL versus Carfax. Maybe Carfax today vs. 5 years ago. That is always there. They may not have had the level of portfolio maturity yet; maybe they are just operating on their own, or maybe they have a focus on customers and capacity management, or PDLC—whatever the case, maturity grows over time.

Anyway, that brings us to wrapping up this session. I know there are still some questions coming in; we can address them offline. Ultimately, we gather here to ensure everyone is rowing in the same direction, but it’s not just about one team. We have executives, multiple teams, stakeholders, cross-functional groups, plus capacity, program and project management, delivery, engineering, PDLC, and operations. In the end, we all come together to build product, the right product for the customer, the right product to drive business, and then we have a good way to deliver it. 

That’s really what Dragonboat is about: supporting your end-to-end strategic portfolio management. But you don’t have to take all of them; you can take one, two, or three as you’re getting ready. If you’re interested in the space, or if your company is going through the journey, talk to us, and see how we can help you. As Aaron and I mentioned earlier, having visibility into the data is foundational. From there, you can get people buying change, see where you’re going, and you can make changes along the way. So we can even just start with that, just integrating with all the data.

It’s been a great session—thank you so much, Aaron. I can’t wait to see more of your insights as you’re evolving your journey at Carfax—what worked best, and other learnings. If you want to learn more or get in touch with Aaron, here’s his contact and I know you teach MBA classes as well. So I’m sure there’s lots of fun, even more interesting conversations that we can learn from. 

And here’s Product Ops HQ, a community where we can all learn, share insights, and ask questions. With that, we’re wrapping up today’s session. Thank you, everyone. You know where to find the people and the community you’re interested in. I also welcome you to join us to learn more about Dragonboat. 

Thank you, Aaron. Thanks, everyone. Bye-bye!

Reference

• Product Ops HQ: https://www.productopshq.com
• Dragonboat: https://www.dragonboat.io
• Aaron Hall on LinkedIn: https://www.linkedin.com/in/aaronhallpmp/
• Carfax: https://www.carfax.com
• S&P Global: https://www.spglobal.com
• New York Stock Exchange: https://www.nyse.com
• Virginia Tech: https://www.vt.edu
• US Army: https://www.army.mil
• Project Management Institute: https://www.pmi.org
• Stride/K12: https://www.stridelearning.com
• AOL: https://www.aol.com
• Neustar: https://www.neustar.biz
• Carfax’s Playbook: https://jobs.jobvite.com/carfax/p/playbook
• Federal Government: https://www.usa.gov
• Time Warner: https://www.warnermedia.com
• General Electric: https://www.ge.com
• Verizon: https://www.verizon.com
• Jira: https://www.atlassian.com/software/jira