Avoiding Complacency After Success

“Success is the biggest inhibitor to future success,” says Barry O’Reilly, coauthor of Lean Enterprise: How High Performance Organizations Innovate at Scale. “When you’re running multibillion-dollar companies successfully, all your numbers look good, your charts are heading up and to the right, and all the strategies you’ve deployed your whole career have led you here, to the success you currently have. So, why change?”

It may seem counterintuitive to regard success as a risk, but it’s been shown time and again that enterprise companies can get complacent with their position, and while focused on incremental improvements, they lose sight of the bigger opportunity and get overtaken by younger, hungrier competitors.

“It takes real courage,” continues Barry, “to recognize that you constantly need to challenge yourself—to see if what you’re doing is working. Should you be trying something else? Should you change?”

Staying Disciplined After Success

“The hardest thing is that you have all the money in the world,” says Lisa Long, VP of Product for Telenor, a Norwegian telco with over 200 million customers in 27 markets. “What are you going to spend it on? Unlike startup companies, where you’re starving for resources and you have to be very sensible about what you spend cash on, in a large enterprise company you have a lot of resources. The problem is you have so many resources that it’s very tempting to carry on with projects that are not particularly successful because you think, ‘Maybe there’s just one more discovery we could make around the corner.’ It’s very hard to know when to stop putting resources towards something, because it’s not as life-or-death as it is in a startup company.”

Maintaining Focus as You Scale

Any good product leader will tell you that you can’t be everything to everyone. All companies go through this struggle. They need to stay focused on a specific market while still scaling their business. For the most part, this might be easier when companies are small. Early-stage companies tend to be more focused on a specific problem, but this becomes harder as they grow. By the time they are enterprise size, the pressures of growth and scale diffuse any hope of staying focused.

As the product leader in an enterprise, you might find that the hardest part of your job is delivering value to existing customers while simultaneously growing existing or new markets. There is no silver bullet for overcoming this friction, but there are some patterns worth noting from successful product companies.

The first consideration for the product leadership is to ensure the organization has at least one product that truly sets it apart. Assuming you have multiple products, you’ll want one that stands head and shoulders above the rest. It doesn’t always have to be the same product, but for enterprises this would be something game changing or market leading, and that could deliver value for an extended period of time. For a consumer-focused company like Apple, this would be the iPhone. For a B2B company like Intuit, this would be QuickBooks. For Google, it’s search underpinned by AdWords. This product is your flagship and will carry the dual duties of delivering massive value to the customer and the business, while also acting as the tallest peak in your publicity engine. For those companies that have a suite of products but no clear big hit, we recommend you pick the product with the greatest potential and focus on making it the standout.

Tightly connected to this is understanding which of your products is the most effective wedge device for introducing your value to the customer. In many cases this will be the same product that stands out above the others, but it may not be. Figuring out which product opens doors and builds relationships with your customer base means you’ll have an entry point for the other products in your suite. If your standout product is the marketing engine, then this product will drive your sales.

Finally, the product leadership needs to focus on the most interesting customer segment. Not all customers are created equal. Some are responsible for high revenue but don’t have a big market share. Other segments have powerful networking influence but may not generate significant bottom-line value. It’s essential that the leadership determines which of these customer segments are going to achieve which OKRs. Connecting the dots here means launching a highly focused marketing effort that aligns with product delivery goals.

Previously of HSBC and currently Senior Product Owner, Digital Workplace and Collaboration at Sainsbury’s, Randy Silver expands on these ideas: “Things operate on a different scale in enterprise. At smaller firms, I felt like a failure if I couldn’t show results in two or three months. At an enterprise, a global change can take two or three years. Add a few more months if you’re in a regulated environment. Trying to deal with things like cross-border data transfer, bringing on a new vendor, or even asking for feedback from staff in other countries can be really complex. And not just the legacy systems. Processes can be absolutely byzantine, and the organizational dynamics even more so. Companies of this size often grow by merger and acquisition, and inherit different systems and processes between business units or geographies. There are also often undocumented checkpoints that you’ll need to go through to get any existing systems or processes changed, above and beyond the known structures.”

Barry O’Reilly adds, “Typically the factors constraining innovation are conflicting business goals, competing priorities, localized performance measures, and success criteria. While these have traditionally been the tools of management—to control workforce behavior and output—in highly competitive and quickly evolving business environments, they also have had the adverse effects of killing creativity, responsiveness, and ingenuity.”

“We have over 140 products in our portfolio,” shares Maria Giudice, VP of Experience Design at Autodesk. “You can imagine that there is a lack of cohesion from one product experience to the other. That made sense many years ago, but now as we are moving from being very software focused to being very experience centered, cohesion is a requirement. You have to ask yourselves, are your customers getting consistent experiences, or are you shipping the seams of your organization to them?”

Delivering a Customer-Centered Go-to-Market Strategy

We are going to make an assumption here, but in most cases if you are building for the enterprise or you are an enterprise organization, you are most likely a publicly traded organization. If this is the case, as a senior leader, the term “beat and raise”¹ should be front and center in many of the discussions you are having each week. A big tension for a senior leader in product management is the sales and marketing teams’ influence in the product’s go-to-market strategy. Does product marketing live in product or does it live in marketing? Who is the tip of the spear of the how, the what, and the when for product releases? Who decides what features need to be built? Many of these kinds of decisions in the past were often, if not always, revenue driven.

This won’t come as a surprise, but many of the companies we interviewed have their enterprise product roadmaps dictated to them by the upper third of their revenue-generating customers. The reason most often cited for this is that an organization can hit its annual growth forecast for the “beat and raise” model. Predictability around these metrics drives shareholder growth and value for nearly all of these companies. Sprinkle in some employee restricted stock units (RSUs) or other forms of equity for senior leaders and individual contributors, and you have a tenuous environment. This situation can get nasty if it’s not aligned with delivering customer value. Having been in this situation, we empathize with you. We know that this can seem like a bow wave that is insurmountable. However, the best product leaders in the world have the ability to get ahead of this pressure. They have the ability to foresee what is on the horizon before the go-to-market teams do. A secret weapon that the most successful product leaders deploy is discovery and human-centered research principles. Collecting insights and data well before the executive and market pressures start dictating changes is critical at large product organizations. Product leaders need this customer-generated information before an analyst on an earnings conference call asks the inevitable difficult questions.

The old saying “data doesn’t lie” comes in handy when attending executive and market metric-related meetings. Armed with statistically significant and repeatable data that show overlapping themes gives the product leader a huge head start. Data that reinforces what the customer segments want—and is willing to pay for—shows a path for future releases and innovations. It points out the importance of building a sustainable experience rather than a features and benefit model. By doing the research, a product leader is able to tease apart the wants of the upper third and the “beat and raise” situations, while simultaneously solving for the valuable user and buyer base problems.

Communicating and Collaborating Effectively

The other common thread with successful product leaders in enterprises is their communication skills—and not just with their teams and direct bosses but with sales and marketing as well. The best product leaders have a kinship with their counterparts in sales and marketing. In some cases, leaders told us that they share desks to ensure consistent collaboration on all projects. For communication between these departments to be effective at scale, we recommend at least a weekly meeting. The sales and marketing groups should regularly be informed of all the appropriate discovery and delivery updates. Equally important is for the sales and marketing counterparts to be passing insights back from their departments to product. After all, sales and marketing are at the frontline every day and have lots of customer feedback to share.

Avoiding Sanitized Data

Barry O’Reilly outlines what he views as one of the biggest challenges in enterprise environments: “So much of the information that gets to executives is sanitized. For example, a product development team might be working on something and they push a report through, but there’s something they’re a bit ashamed of—or it’s a vanity metric rather than actual metric that they want to talk about, something that’s really a problem—and they hide it because they’re afraid how it’ll be treated. Or, they put something red in a project and it goes to a more senior person and they don’t want get into trouble, so they turn a red to an amber. Then a more senior person changes that amber to a green. Suddenly, you’ve got leadership of these large companies looking across a dashboard that’s all green, and they’re going to make strategic business decisions based on this information. In other words, they’re making decisions off incorrect information. So it shouldn’t be a surprise when the decisions they make are wrong. Then the results are wrong. Now you have this cycle of bad information running up and down the organization, and as a result, bad decisions being made up and down the organization, which result in more bad decisions, because the cycle is actually toxic.”

This is where a product leader’s ability to simply get up and walk around the office, or out of the building, to speak to their teams and their customers really helps. Because getting that raw information directly from the source ultimately ensures you make better decisions.

“Probably the best example of this,” adds O’Reilly, “is Reed Hastings at Netflix. He has a standing 30-minute meeting with all the directors of the company every 12 weeks. Every three months, he has a customer-testing session with everyone who runs or leads a major department in the business to understand what’s happening, what’s working, and what’s not.”

Building this sort of sensory network—inside and outside the organization—to funnel accurate, unsanitized information and feedback up to the right people so they can make better decisions is the hallmark of an exceptional product leader.

Measuring the Right Thing

As we outlined earlier in this book, building great products relies on measuring the success of those products and your team’s ability to move the needle on those metrics. Most enterprise organizations, however, are measuring the wrong things.

YouTube’s Jacquelle Amankonah measures success in a few different ways. On the creator side, what’s very important to YouTube is their satisfaction. “We have something called CSAT, which is creator satisfaction. We aim to make that high as possible. Creators are the lifeblood of the product. Without them we only have viewers and their satisfaction.” The CSAT score measures YouTube’s product success by scoring the ease with which a creator can build a community on YouTube.

“How much are we communicating to them in a way that is helpful to grow their business on the platform? Are we giving them the tools they need to proceed? Are we clearly articulating strategies that they can use in order to grow on YouTube? Our services, our support, our partnerships, etc. That’s a big metric for us on the creator side.” Amankonah also uses a number of surveys that her team sends to creators at various frequencies and with various types of questions. “I’d say that is the biggest driver [of data] into that metric,” she says. “We also make sure that we cross-check that metric in conversations with creators, to uncover more about the why behind some of the things that they’re telling us. Trying to dig into any variances we see between different groups or different verticals. Perhaps a music creator feels differently than a gaming creator; why is that? We aim to survey our creators so we can hear in their words and their opinions how well we are hitting the mark with them as a platform.”

During their first 25 years, Adobe measured just one thing as its key metric: how many software packages it sold. But this metric doesn’t tell you anything about adoption rates, usage, or customer satisfaction, nor does it incentivize developing a long-term relationship with customers. What it does incentivize is selling customers a new version as often as possible. When Adobe moved to the cloud model, it also fundamentally changed its success metrics to focus on subscriptions—signups and renewals—which is a very different relationship to have with your customers. This change led to the Marketing Cloud, a whole new business area for Adobe, because it directly aligned the product (online marketing tools) with the customers’ needs (acquiring and retaining customers).

How do you determine which metrics and measurements are right for your organization? Given that you need to pick your KPIs (key performance indicators), OKRs (objectives and key results), or whatever measurement framework you choose to determine success, how do you know what will give you the right feedback? The initial problem for many product leaders is they have a massive reservoir of data and insufficient methods for turning that data into insights. Leaders need a process for how to pick and choose which measurements to focus on and why those are meaningful.

Jonathan Gowins, a Product Manager at D+H, describes the company’s approach: “One KPI is revenue. That’s just a simple one. If we can’t sell it, can’t generate revenue, then it’s not performing. The other [metric] is NPS, net promoter score, which has swept basically all industries by storm. So we’re in touch with how well it’s performing with clients and what perception is. Also just the hard dollars behind it, because some of you can sell something and you can really adapt the pitch, or the premise, or the value prop. Then once something’s live, maybe it actually tanks and it’s problematic. NPS will come in and pick up that sentiment and share that with us and give us that feel for the product. We use both of those things.”

D+H is a fintech product company with a focus on designing and developing B2B solutions for the banking and finance industries. Money is inherently emotional. Saving to buy a new house, purchasing a gift for a loved one, or figuring out how to pay for costly car repairs all spark emotional responses. In an age where we’re instantly connected to people around the world, we expect the same level of access and control over our finances. Gowins and other product managers like him are listening to diverse stakeholder groups and distilling those wants into products that work for real people and their assets. Gowins knows that even though his company produces a B2B product, the end user is a priority, and it puts an emphasis on measuring that with NPS scores.

Whatever scoring and measuring system you opt for, remember that what you’re choosing to measure will get the attention of your team and company, so choose wisely. “As far as data goes, we work with our clients because they set the precedent for what they need,” says Gowins. “Ultimately we deliver the solutions that they need. If they buy it, that’s validation number one. If we get a strong NPS, that’s validation number two.”

This underlines the importance of choosing balancing metrics—tracking both performance-oriented numbers like revenue, ARR, and CAC, and quality or customer satisfaction numbers, such as LTV and NPS.

Working Within the Company Culture

“Some  people can have an entire career—with many different job experiences—within one large firm,” says HSBC’s Randy Silver. “This creates a unique corporate culture, which may be hugely resistant to change, but may also be the reason behind the company’s original success and why it hasn’t yet been disrupted. That can simultaneously be a huge frustration and a massive opportunity. Even if you never learn to love the culture, you’ll need to develop an appreciation for it. Without that, you’ll never be able to engage the lifers.”

Of course not every enterprise organization has this scale and culture, but even if it doesn’t, an enterprise product leader must consider how their team fits into the overall structure and its culture, while focusing (even more than their counterparts in smaller organizations) on communication. Their ability to influence, lead, and inspire both laterally and upward in the organization is more important in enterprise organizations that need to create the space for a customer-focused, iterative product-development function.

Enterprise product leaders must also be mindful of their company’s org structure, budgeting and control, and development process. “When you create an org chart, you are creating your product—the seams in the organization get reflected in the product; the depth of feature work gets reflected in resource allocation; the coordination across job functions gets reflected by the leaders you choose; and so on,” says Steven Sinofsky, former President of the Windows Division at Microsoft.

So in order to effect change, a product leader needs to be able to present it in a way that the organization understands. “By linking innovation to a growth strategy, it ensures it is a targeted, strategic, and funded priority for the organization, and provides alignment between business strategy and execution through the action of delivery,” adds Barry O’Reilly.

Communicating with Internal and External Customers

As the organization grows, so does the opportunity for poor communication. If your team is bigger than 20 people, it’s easy to forget to check in on a team member, or to overlook informal customer meetings. A healthy way to think about communication is this: everyone is a customer. That means that both internal teams and external users are your customers. As product leader you will get a better perspective when you see the world through the lens of your customer. Treating your internal team like customers automatically puts you in the servant leader mentality. A servant leader focuses primarily on people’s growth and well-being. Traditional leadership generally involves someone at the top of the organization or team accumulating and exercising power. In contrast, the servant leader shares power, puts the needs of others first, and helps people develop and perform as highly as possible.

The best product leaders make time for communication by building it into their calendars. Just like getting fit requires you to add your workout to your schedule before meeting the rest of the obligation, so too does good communication. “I’ve made it a practice of mine to spend time with my peers and colleagues to make sure we’re all connected. The human element is essential,” confirms Matt Asay, VP of Mobile for Adobe Marketing Cloud. This applies to connecting with teams and with customers. In maturing companies it’s easy to turn to the reports or the data and conclude you’ve done your homework, but the real insights still happen with face-to-face communication. “It’s not possible to do it any other way,” says Matt Asay. “Data is essential, but people matter more. Each week I buy lunch for anyone doing anything with mobile, assuming they are in the Utah office.”

This kind of regular contact with team members is key, but there are other actions you need to take in order to understand your customer needs as well. Zmags’ Cait Porte says that communication in an established company needs to happen in a variety of ways: “This is probably par for the course for product management. In some capacities I’m doing usability and user experience testing with my team. I’m working with our UX team right now to build out what those scenarios are, and to make sure that we’re listening to that feedback. In other scenarios, I’m understanding what our customers’ top priority issues are, whether as a company or specific to our products.” This combination of formal and informal communication provides a good chunk of what Porte needs, but she prefers to use structured exercises to get specific insights. “We do something called the hundred-dollar question: How would you spend one hundred dollars in our platform if you only had one hundred dollars to spend? It’s a great prioritization exercise to do with customers.” These highly targeted or structured communications are designed to extract specific data or insights from customers.

As with most leadership positions, a product leader is a bottleneck for communications and, subsequently, decision making. If the product leader isn’t getting the right information, they won’t be able to make informed or timely decisions. Knowing which channels and exercises get the most relevant and important information is part of the job. Just being a catchall for all the inputs solves nothing. In fact, the scenario of having to filter all the information through the product manager or leader makes the bottleneck problem even more acute. The best product leaders are also masters at filtering good communication from mere distractions. They are highly selective when it comes to communication inputs and sources. Without question, the best source is the customer. Direct contact with customers and users is by far the highest-value input. “I probably talk to customers at least once a day in some capacity, and I really like that because it grounds you when you’re thinking more strategically as a business,” says Porte. “Hearing from the customers and understanding what their problems are is really critical for product managers, and I like to make sure that I’ve kept that consistent through every role that I’ve been in.”

“When we’re building the product, we do a lot of user interviews before we start the design work,” says Joe Ranft, cofounder and Head of UX of Cinch Financial. “We conduct one- to two-hour interviews with users, and that helps us define what information people need.” Ranft explains how his team would develop insights by making communication with customers easier: “We have one product which asks people to snap and post a picture of a monthly bill, and we let them know if they should change it. That was how we realized people don’t just want to shop around, they want advice. What we learned translated into working on a brand new product. I like UserTesting.com, but I also like to be sitting next to the user to be able to ask them questions, which I find harder with some of the online testing methods. I’m still a big fan of traditional user testing where you recruit users, bring them in, watch them use the product, and ask them questions about what they’re thinking as they’re using it.”

Ranft confirms what Porte and others told us: that face-to-face communication with customers is the preferred method of getting useful insights. “You see their faces,” says Ranft. “You can tell when they’re confused. You can see, especially now in testing phone design, or mobile designs, people try to tap on things that don’t work. I think you really have to watch. With online user testing, it’s harder to tell what their feelings are. That’s why the old-fashioned way works: bring them in.”

Because so much of the product leader’s work is digesting information and using that information to make decisions, they also need to understand that they are essentially acting as a filter to the team. They must ensure that only the most important information and critical insights are available to their team members. Taking this a step further and determining how to share these insights with the team is also part of the product leader’s job. “I also work on analytics with our customers because one of the things that we’re looking to do is build out an analytics dashboard,” says Porte. “We’re really interested in understanding how the customer is measuring success. What factors are important to their business? What do they want to see in our products?”

Promoting Collaboration

Great product management “is about change, and change demands leadership,” says Autodesk’s Maria Guidice. “Therefore, today’s product managers and designers must be leaders. Go from being producers of artifacts to champions of a connected society. The best ideas and solutions come from multidisciplinary teams where everyone feels like they contributed to the process. Everyone is creative. Make everyone part of the creative process.”

Treat your peers and coworkers as co-creators, and respect the fact that each person is able to bring something to the table based on their area of expertise and their own view of the world. Be mindful that diverse teams may share the same goals, but they speak different languages. More brains produces more ideas and better solutions. How do you build a strong internal community?

“People think that cross-functional only matters at a small product team level,” adds Barry O’Reilly, “and that’s incorrect. The highest-performing leadership teams, we’ve discovered, operate at a cross-functional level across an entire business. That’s the whole point of having people who lead departments. It’s just at a macro scale rather than a micro scale, relative to an individual product development team.”

Changing the Corporate Culture

“To break the silos, we are identifying big problems to solve, and then we are handpicking people from different products to solve that problem together,” says Maria Giudice. “This breaks down the silos, but it also makes for a better product experience because their individual product biases get baked into the strategy. We are also creating practice taskforces. We have people who are passionate about research, people who are passionate about visual design, people who are passionate about information architecture, and they convene and they have their own charters. Their job is to elevate the practice throughout the organization so they can ship better products for the future.”

Engendering change in a corporate environment isn’t something you can do alone, no matter how great a leader you are. Being collaborative about change and innovation, and employing the resources already available to help you make those changes, is critical.

“Tap into internal sources of ideas so that every part of the organization is involved in the innovation process,” suggests Barry O’Reilly. “This often requires a shift in corporate culture—removing the ‘not invented here’ mentality—to ensure that intrapreneurs and other leaders are willing to open up to external sources of innovation. Be prepared to tell people within the business to consider the possibility that another part of the organization might be best placed to exploit some of their ideas—together or maybe even without them.”

Showing, Not Telling

“With senior leaders, I constantly try to create scenarios where you can break their mental model of the world through safe-to-fail experiments—either testing what a new product might be, testing what a new process might be, or actually testing some of the changes that they’re trying to make in themselves as a leader,” says O’Reilly.

Lead by example and show your team or peers how to live and breathe this user-centric, iterative product-development process so that they can truly understand how it works, how valuable it is, and how hard it is to execute well.

Tanya Cordrey, former Chief Digital Officer at the Guardian, adds: “Find a way to get some quick wins, and get some metrics moving. Everyone gets really excited about that. You should celebrate every time figures go up. You have a job to build your own credibility and build your team’s credibility. When you’ve done some of those things, everyone gets really excited, and this lets you make a case for bigger changes.”

“Doing iterative and experimental, test-and-learn product development, although it looks really simple on paper, is exceptionally hard,” O’Reilly concludes. “Getting executives and team members to experience that is actually one of the most transformative things you can do. They start to empathize with leadership, and leadership starts to empathize with the people on the ground about how difficult this stuff is, rather than just thinking it’s easy to do these things.”

Maintaining Vision Clarity

“The role of the roadmap is to illustrate our vision of where we’re going,” says Matt Poepsel, Predictive Index’s Vice President of Product. “I think we’re doing some pretty innovative things in this space, and to be honest, a lot of our competitors are not; they’re sort of stagnant by comparison.” Predictive Index, a workforce analytics company that’s been in business for 50 years, generates over 3 million job seekers and employee assessments every year for more than 5,000 clients worldwide. “For us, the roadmap is really the culmination of how we expect to grow into our vision,” says Poepsel. The key with this roadmap/vision matching is that it’s very dynamic and gets reviewed and revised every 90 days. It balances the reality of a dynamic, evolving product environment while addressing the need to provide a long-term vision. “The first week of each quarter, we’ll produce the latest version of the roadmap, but it’s actually a 15-month roadmap,” he says. This approach balances the counterintuitive requirements for the product leader: to focus the team on the distant future while managing for the near future.

Poepsel describes how this works in more detail: “The reason we publish a 15-month roadmap is that it recaps what we accomplished during the prior quarter. This is huge for us, because sometimes it’s hard to keep up with an organization that is moving very quickly. To answer the question, ‘What did we just do?’ we include a 90-day in arrears of what we most recently delivered, and then we outline a forward-looking 12-month forecast of what we believe we’re going to be able to deliver within specific timeframes. This way, our partners can be aware of what’s coming and make sure that they’re fully versed in what to expect.”

Taking a Product Portfolio Approach

Knowing how to deploy an enterprise organization’s considerable resources in the most effective manner is key to successful product leadership there. Because every product is different, whether it’s in the idea stage or in a mature stable market, ready for growth or ready to be sunsetted, it’s important to set up your product organization accordingly. A portfolio approach lets you consider all the products in a holistic manner while assigning resources to each product according to its current stage and needs.

Telenor, like IBM and Microsoft, has designed a five-stage system to categorize its products internally. From the first stage, where a product is simply an idea around a group of users exhibiting similar behavior that needs more research, to the final stage, where the product is in a mature state and needs optimization, the stages allow Telenor to focus its resources accordingly.

In the first stage there are going to be a lot of ideas that fail—and that’s OK. By staging its resource allocation, Telenor can ensure that only validated ideas progress to product development and that only validated products progress to the growth and marketing stages.

Importantly, throughout the five stages, everything they learn is stored in a central database. VP of Product Lisa Long says, “The database has all this information about what kind of stuff we have tried so that other product managers who are saying, ‘I’d really like to know what we’ve done in education in Bangladesh,’ can look it up in the database and find out, ‘Oh, OK, we did do a project on this before. This is what we learned.’ It springboards them for the next piece of learning they need to make their own product better.”

Thinking Small to Think Big

There’s nothing more empowering and more likely to drive innovation than allowing for entrepreneurship in your organization. And the only way to allow for it is to take executives’ hands off the reins and introduce a level of autonomy within your company, at the division, product, and team level.

Earlier in this book, we discussed how an autonomous cross-functional team that is close to the customer, and has the independence to execute its own strategy and tactics, is by far the best way to build products people love. But how do you enable this at scale?

Breaking components of your business into smaller parts is an obvious solution. Amazon famously adheres to the concept of the two-pizza team, where no team is allowed to grow so large that it can’t be fed by two (large) pizzas. With over 200,000 employees, that’s a lot of teams.

Trusting smaller teams to solve problems is another approach. Can four people at a huge enterprise company make a difference? At Adobe, they do. Talin Wadsworth, Adobe’s Product Design Lead for its latest product, Adobe XD, explains how such a large company can think small to get big new products out the door. As most product people will remember, the story starts with the shift in design tools from stalwart products like Photoshop and Illustrator to hybrid tools like Fireworks. “It was built for our job,” says Wadsworth, of Firework’s relevance to digital product designers. “Although we still had designers using Photoshop, and we all used Illustrator to some extent, Fireworks was the ideal tool because you didn’t have to think about resolution. You were designing for screens, and this was a tool for screens, so you could trust that it was going to be accurate.” Then the axe dropped on Fireworks and a small startup called Sketch started threatening Adobe’s dominance in the digital design tool market. Fireworks had been a small part of the company’s creative tool suite, but the shuttering of the product sent ripples of frustration and confusion through the digital design industry. This sent a message to Adobe that there was an opportunity to direct new efforts to tools that would help designers and product people craft new designs.

“We missed it,” says Wadsworth. “We knew the end was coming, but at the same time, we were exploring all of these other tools to help us do our jobs better.” Sketch was already making waves, but designers were also trying to solve the problem of how to create new products at the earliest stages and would try any prototyping tool they could get their hands on. Keynote seemed to be the favorite of many. Wadsworth empathized with this product design challenge: “The majority of my work for pretty much a solid year was done in Keynote. In my role, as a lead [product designer] it’s really about doing the early concepting and storytelling. I started building in more and more interactivity and more dynamic flows to my presentations to my design.” Wadsworth and his team discovered that Keynote was a really handy tool to prototype quickly. “Then of course we saw what was happening and realized that we need that modern tool,” he says. Instead of doing their designs in one app—for example, Photoshop or Sketch—and then prototyping in another, the team wanted a single tool to design and build their ideas into testable prototypes. Design and prototyping needed to be combined. “We started feeling that this was one tool, a design tool that, of course, could give pixel-accurate designs that I trust and feel like I can rely on, but with the added aspect of prototyping. We wanted motion and interactivity built into the DNA of our tool.”

Product leaders are often challenged by the situation where the tools they use influence outcomes. “It’s this chicken-and-egg cycle where there’s a problem, a tool comes along, and then once the tool becomes integrated into the process, it can influence those outcomes,” says Wadsworth. “If you had a tool that brought design and these new features—motion and interactivity—together, you would end up with a tool that designers could use to really push the boundaries of interactive design. We started with this need as designers here at Adobe.”

Making It Before You Make It

The phrase “fake it ’til you make it” has likely motivated many early-stage product teams. As these teams become more established, we recommend going beyond this idea and building prototyping into all new idea development. Wadsworth says, “Our process began with a real startup feeling. It was four of us, so we could talk about something in the morning, implement it, and be testing by the end of the day.” He explains that the initial product design work was done in Keynote, with the first prototypes trying to address pieces of this puzzle, as there was early agreement that the team couldn’t take on the whole task immediately. The very first prototypes were simple tools and features focused on screen design, in the web browser. “One of the first [prototypes] we made was just a simple repeater,” Wadsworth continues. “We knew in UI design that you sometimes need to have the ability to quickly lay out repetitive pattern of shapes. With this prototype, you could take a shape and then you could repeat it as many times—either horizontally or vertically, in rows and columns—as you wanted.” This humble approach is necessary in any size organization, but the process of simplifying the early prototyping and testing is even more important when there’s an embarrassment of riches. Too many resources and not enough constraints can make the process bloated and the participants lazy. “We needed some process to organize what problems we were going to tackle. There were so many we could have been focusing on, but what we chose could be likened to any number of processes. Basically we had to prioritize. We had to figure out the story we wanted to tell and then we had to figure out how we were going to get there. You’re bootstrapping it, figuring it out as you go.”

Even once the prototyping and testing is done, the desire to keep the bootstrap mentality should persist. Wadsworth describes how they took the initial validated concepts through the next steps: “From there, it was really about generating excitement, continuing to refine our story. That was the sexy part. The other parts of getting the tool made were really just doing our own work.” Despite the fact that Adobe is a large company, it didn’t assume anything about its customers’ potential adoption of the tool or their unspoken needs. “We’re a company focused on selling creative tools, so we did a lot of work on market and user research,” Wadswoth says. “We started showing some of the early prototypes and lining up partnerships with external design groups, just showing them and validating some of the early concepts that we had.” Adobe attacked this product opportunity with the startup mentality to ensure scalable success.

Pat Petitti, cofounder of Catalant (formerly Hourly Nerd), told us how he was able to generate significant traction both internally and with prospective customers and investors by continually prototyping new features and concepts: “It started out as a 5- or 6-page mockup in Keynote, but as time passed it grew into a 70-page analog of the product we were building behind the scenes.” Ultimately Petitti credits the prototype for locking down the company’s largest client, GE, and helping to raise $33 million for its emerging project matching platform.

This type of prototyping can be valuable to companies of almost all sizes—whether you’re an established brand like Adobe or a disrupter trying to maintain the post-startup momentum like Catalant.