Workday CTO Gabe Monroy reveals why leaders must stop chasing flashy launches and start focusing on product friction.
Sydney Scott
Editorial Strategist, AI
Workday
Weeks into his career at the company, Workday CTO Gabe Monroy walked into a conference booth at Workday Rising and did something most high-ranking executives rarely do. He sat down and used his own company's tools as a regular developer would. This undercover boss move revealed the gritty reality of the friction that makes software feel like a chore.
While many tech giants focus on the flash of a new product launch, Monroy argues that the real battle is won in the unglamorous trenches of fixing what is already there.
Chatting with Workday’s Head of Developer Relations Nick Moores for the latest Future of Work podcast, Monroy sounded the alarm on a hard truth most companies ignore. Instead of polishing current tools, organizations chase the next big feature. It creates a gap where the market expects a transparent platform, but the software delivers a black box that is hard to open and even harder to use.
While many tech giants focus on the flash of a new product launch, Monroy argues that the real battle is won in the unglamorous trenches of fixing what is already there.
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The incentive structures within software companies are often the biggest enemy of a smooth user experience. Product and engineering teams are usually rewarded shipping products. Stepping back to look at how all the pieces work together—from the first day of onboarding to advanced tasks—is rarely a priority. This lack of focus turns software into a collection of features rather than a cohesive tool.
“A thing I've learned managing large teams of products and engineering and other disciplines is that the job of reducing friction in products is never ending,” Monroy says. “There tends to be a lot of incentive in big companies to not prioritize doing that because most companies are interested in launching the next big new product or the next big new feature.”
When companies fail to prioritize this work, they don't actually save any effort. They simply outsource the labor of finding and fixing problems to the people paying for the software. "What would end up happening is your customers end up doing that work," Monroy says. "And they're the ones who are complaining."
Reducing friction is not a one-time project; it is a never-ending discipline. For Monroy, this work must come before any marketing or public promotion.
“In past lives, I asked folks to first make sure that they felt like their products had minimal friction, were easy to adopt, easy to pick up, easy to learn,” Monroy says. “The core feedback that was being addressed by end users in the market was something we had to get a handle on and only then should we prioritize going out to market, taking that megaphone out and really blasting the message out to the world of developers. I gotta say, that was a big mindset shift.”
Moores notes that identifying these pain points is something to celebrate rather than hide. In a healthy developer community, discovering friction is like "solving a puzzle together."
“When you're trumpeting the things that have been made better and you're not trying to shove it down people's throats, it brings so much more respect and trust to your audience because they know you're talking about real things,” Moores says.
“You are not glossing over friction. Discovering friction with a developer is something almost to celebrate.”
“A thing I've learned managing large teams of products and engineering and other disciplines is that the job of reducing friction in products is never ending”—Gabe Monroy, CTO, Workday
For years, the gold standard for enterprise software was a closed, controlled environment. Some organizations even preferred software that ran on a server in a physical closet because it felt like a safe, literal black box. However, this mentality has become a primary bottleneck for modern innovation. A closed system is the ultimate source of friction because it prevents the outside world—and modern tools—from seeing or interacting with the data inside.
Lack of transparency creates a massive hurdle in the world of AI. Agents require APIs to function, but a black-box system lacks the necessary natural language metadata and documentation to make those APIs usable. When a platform is closed, developers just have to hope an agent follows rules that aren't clearly defined by the system. Maintaining an opaque posture is a strategic barrier that forces developers to waste time fighting the software's limitations instead of building on its capabilities.
The shift from a curated and exclusive partner model to an open platform is a massive change in how tech companies think. While closed systems can sometimes offer higher quality because they are strictly controlled, they offer much less choice. Moving to an open ecosystem allows a variety of partners, including small startups and individual developers, to build on top of a high-value platform.
This transition requires a mindset shift across the entire organization. It means companies must prioritize agent-ready APIs and reduce the friction of accessing the platform. It also means moving away from vibe coding when dealing with high-stakes data. For mission-critical tasks like payroll or finance, companies need confidence that the software will work correctly every time.
“When you're trumpeting the things that have been made better and you're not trying to shove it down people's throats, it brings so much more respect and trust to your audience.”—Nick Moores, Head of Developer Relations, Workday
At the end of the day, reducing friction is about respecting the humans who use the tools. A great developer community thrives on the connectivity between people who share lessons and help each other move faster. When an organization invests in the quiet discipline of reducing friction, it’s making a strategic investment in the success of those individuals.
The work of making software easy is a never-ending commitment that requires leaders to lean into the discomfort of change. It demands staying focused on the small, unglamorous details that most organizations ignore in favor of the next launch. The goal is to build a platform where the hard work of removing hurdles is done behind the scenes, allowing the people using the tools to focus on creating real value.
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