Chris Butler is a seasoned technology leader with a proven ability to lead teams, drive innovation, and deliver results in a fast-paced and dynamic industry. He is a highly accomplished executive with over 20 years of experience in the industry. Prior to his current role at Google, Chris held several leadership positions at companies like Microsoft, Facebook Reality Labs, Kayak, and Waze, where he gained extensive experience in the areas of product management, engineering, and business development. In this episode of Unlearn Podcast, Chris joins Barry O’Reilly to discuss his career journey. He emphasizes the importance of challenging mental models and learning from user research and data analysis to shift perspectives towards new technologies.

Where Novelty Leads

Chris talks about his passion for novelty and his interest in exploring new things since his youth. He mentions his early interest in technology, having created “red boxes” to make payphone calls. Chris credits his father, who was an art director, for introducing him to the transition from traditional typesetting to digital typesetting using programs like QuarkXPress, Adobe Illustrator and hand coded HTML. [Listen from 1:20]

Chris initially believed that project management was about being as certain as possible. However, after several years in product management, Chris realized that burning away certainties was an essential aspect of the job. His first job at Microsoft involved a mix of project management and product management. He emphasizes the importance of recognizing when to strip away established practices and experiment with new methods to achieve desired outcomes. Barry suggests that these moments of inflection occur when individuals change roles or take on new responsibilities. “A lot of the learning journeys [teach you] these practices in a way to recognize when you need to strip them away,” he adds. [Listen from 3:10]



User Research and Industry Shifts

You need to be adaptable and open to change in the technology industry, Chris and Barry agree. With new innovations emerging all the time, you need to be willing to question assumptions and try new approaches. By doing so, you can stay ahead of the curve and continue to make a positive impact in your organization. Chris and Barry discuss the challenges of transitioning from desktop web experiences to mobile ones. Chris recounts how difficult it was to convince executives to invest in mobile, even though it was clear that more people were using their mobile devices to browse for travel options. He had to help them understand that mobile was not just another channel, but rather a new type of omnichannel experience that required a different approach. Barry shares his own experiences with this kind of shift, recalling how customers’ behaviors were starting to change, but the technology was not yet there to support it. He asks Chris how he was able to identify these changes in behavior and help executives understand the need to invest in new technologies. “I had a bit of natural distrust in my leaders,” he replies. Chris often questioned the dominant logic theory that most leaders operated on, which involved using past successes as a mental model for future circumstances. He emphasizes the importance of personal user research and asking the right questions of customers. Chris cites his experience with Complete Seating, a restaurant tech startup, where they were able to “steal” high value accounts from Open Table by focusing on usage segmentation rather than channel segmentation. [Listen from 7:45]

While there are many ways to learn, Barry adds, he appreciates the value of immersing oneself in the real experience of observing people’s behavior, in addition to using technology to measure data. He notes that people tend to stick to what they know and are comfortable with, which can limit their ability to innovate and adapt to new technologies. [Listen 11:00]

The PM Experience

Chris talks about his current role as a lead product manager at Google for the core machine learning group. His team builds all the machine learning solutions for Google and also helps other companies build theirs. “My job is unique in the team because I help corral the strategy for my VP,” he shares. He also helps with PM effectiveness, and works on special projects for his boss. The future of software development, he believes, is a combination of human values and principles with machine learning, creating an environment where probabilistic systems can operate and alter over time. The team’s work is not just about building technology, but also creating development tools that allow for the integration of probabilistic systems. They build atriums for new things that will exist in some way, he says. [Listen from 14:30]

Machine Learning and Artificial Intelligence

Unlike traditional product management where you build a product and test it to see if it works as expected, working with AI and ML models involves feeding the model some information and then examining the output to determine if it’s correct. Chris explains that this process is fraught with uncertainty, from ensuring that the input data is accurate to verifying that the model was coded correctly to producing the desired output. Barry asks Chris about the skills he’s had to develop while working with AI and ML models, as it’s difficult to observe the behavior of a technical model in the same way that one can observe a person’s behavior. Chris notes that explainability is critical in understanding how the model arrived at its output. Additionally, he highlights the importance of naturalistic decision making, which is the ability to transfer expertise from one person to another. He also notes that there are aspects of product management that machines will be able to do better than humans, such as hyperparameter tuning or writing models that can be deployed on multiple devices. [Listen from 18:00]

They talk about the importance of standardizing machine learning components for simpler, long-term model building, emphasizing the need to be centered on helping people solve problems and focus on the customer. [Listen from 22:15]

Collaboration in Decision-Making

Humans have developed cognitive biases over time as a way to conserve energy, time, and information processing. However, working in a group allows individuals to separate their own thinking from themselves and obtain feedback that can help alleviate these biases. Chris cites studies that show how group collaboration can significantly increase success rates in cognitive tasks compared to working alone. Barry agrees, highlighting the importance of discourse and argumentation around a subject in group meetings to improve decision-making processes. He notes that the discourse should be prioritized over the decision-making itself, which is separate and ultimately rests on the authority of an individual. The point of collaboration, he says, is “what you need to learn from the audience, and what the audience needs to learn from you. That’s the information that needs to be exchanged.” [Listen from 25:40]

Both Chris and Barry acknowledge that there are other biases that can emerge in group settings. However, they point to methods such as Red Teaming as ways to address these biases. They also discuss the need for a space where feedback can be presented on a regular cadence to ensure that decisions are well-informed and the decision-making process is robust. Chris highlights the potential of hybrid work and asynchronous communication, but notes that the long-term goal should not be Google Docs that everyone comments on, but rather a separation between discourse and decision-making. [Listen from 27:45]

Looking Ahead

Chris mentions how he uses speculative futures to situate the future in a way that is tangible and more interesting than traditional company missions and visions. “Everything we do when building software is a speculative future because it aims to impact the future and make the world a better place,” he explains. He emphasizes the importance of looking forward when making decisions in product management and aligning the spine of product between strategy, roadmap and tasks. Chris believes that this approach to product management can be powerful and inspiring. [Listen from 29:50]

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