539: How to cultivate an environment where innovation thrives – with Catherine Connelly

Product Mastery Now for Product Managers, Leaders, and Innovators

How product managers can build an environment for breakthrough innovation

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TLDR

In my conversation with Catherine Connelly, a 20-year tech entrepreneur who co-founded MyYearbook at 15 and grew it into The Meet Group (a $500 million exit), we explored how to build environments where breakthrough product innovation happens consistently. Catherine emphasized that innovation culture starts with founders but can be cultivated by anyone willing to embrace failure, iterate quickly, and keep customers at the center of all decisions. The key is creating psychological safety, celebrating learning from failures, and making risk-free experimentation possible.

Key Topics

• Building psychological safety that enables risk-taking
• Structuring product results meetings that celebrate learning from failures
• Creating systems that make experimentation truly risk-free
• Implementing a “kill fast” mindset for unsuccessful products and features
• Using customer stories to drive meaningful innovation
• Balancing operational execution with innovation initiatives
• Leveraging storytelling to gain support for innovation efforts

Introduction

Ever wondered why some teams consistently create breakthrough products while others are barely keeping up on maintenance work?

Today, we’re tackling how to build environments where product innovation actually happens! Every product leader has watched promising ideas die because of organizational roadblocks, excessive caution, or flawed decision processes. You know firsthand that brilliant concepts mean nothing without the right conditions to develop them. From this episode, you’ll walk away with methods to immediately transform how your team innovates.

Our guest, Catherine Connelly, is a 20-year female tech entrepreneur. She co-founded MyYearbook at 15 years of age and grew it into The Meet Group, a social dating company, later achieving exits totaling $600 million. Her recent book Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur captures two decades of creating environments where breakthrough innovations thrive despite constant market shifts.

Building a Foundation for Innovation Culture

Catherine explained that innovation culture starts with the founding team and how they approach work from the very beginning. At MyYearbook, the foundation for innovation began with a sibling dynamic between Catherine and her brothers that created natural psychological safety.

Working with her brothers meant they were used to bouncing ideas off each other without fear of judgment. This family dynamic established an environment where team members could pitch ideas without worrying about negative consequences if those ideas didn’t succeed. The understanding that a person’s worth isn’t tied to the success of their last idea became a cornerstone of their innovation approach.

For product managers looking to foster innovation, the culture supporting innovation typically comes from the founders or founding team. How things work from the very beginning shapes the organization’s approach to experimentation and risk-taking.

Catherine described how this initial foundation allowed her team to maintain a culture of innovation throughout the company’s growth:

• Open Communication: Regular team meetings where discussing failures was normalized
• Psychological Safety: Creating an environment where people could share “dumb ideas” without repercussions
• Focus on Learning: Treating unsuccessful experiments as valuable learning opportunities
• Collective Ownership: Recognizing that innovation can come from anyone, not just the product team

This foundation of psychological safety made it possible for the organization to take the calculated risks necessary for breakthrough innovation. When team members don’t fear judgment or career consequences for failed attempts, they’re more willing to propose novel solutions and challenge established thinking.

The key takeaway for product leaders is that building an innovative environment starts with establishing these foundational elements of safety, open communication, and a learning mindset. Without this foundation, other innovation practices and processes are unlikely to yield significant results, regardless of how well they’re implemented.

Structuring for Innovation: Product Results Meetings

Catherine shared how her team built systems that reinforced their innovation culture, with product results meetings being a crucial component. These weren’t typical status meetings focused on celebrating wins—they were structured learning sessions where teams reported experiment results regardless of outcome.

What made these meetings unique was their deliberate emphasis on failed experiments. Catherine explained that at The Meet Group, they dedicated more attention and discussion time to experiments that didn’t succeed than to those that did. This counterintuitive approach recognized that teams often learn more from products that aren’t performing well than from successful ones.

The structure of these meetings evolved from early practices at MyYearbook:

• Starting with 10:00 AM operations meetings primarily focused on what wasn’t going well
• Evolving into more formalized product results meetings as the company grew
• Requiring every team member to report on their experiments, successful or not
• Using failures as opportunities to brainstorm improvements and adjustments

This system normalized talking about failure and created a culture where experimentation was expected and valued. By making these discussions a regular part of operations, The Meet Group reinforced that innovation requires trying new things, measuring results, and learning from both successes and failures.

Beyond just the product team, innovation should involve everyone in the company. Regular all-hands meetings and company lunches ensured that all employees—whether in QA, trust and safety, product, or marketing—knew about current projects and initiatives. This approach recognized that innovative ideas could come from anyone, not just designated product teams.

For product managers looking to implement similar practices, the key is creating consistent structures that highlight learning rather than just outcomes. By focusing meeting time on understanding why experiments didn’t work and what could be improved, teams develop a more nuanced understanding of their products and customers while building comfort with the experimentation process.

Creating Risk-Free Innovation: Building Safety Systems

For experimentation to truly flourish, Catherine explained that organizations need systems that make innovation genuinely risk-free. She shared an example about an incident over a Thanksgiving weekend when someone accidentally deleted their app from Facebook’s developer account, breaking all Facebook login functionality.

Instead of asking “who did this?”, the team asked “how did this happen?” This fundamental shift in approach led to process improvements rather than blame assignment. The key was creating safeguards that allowed people to experiment without risking catastrophic consequences. By focusing on the process failure rather than individual blame, the team could identify ways to prevent similar issues in the future, such as limiting admin access to critical systems.

Catherine also shared an example from her performance marketing work at The Meet Group. When their parent company expressed concerns about potential mistakes in campaign spending, Catherine explained that they had built-in safeguards beyond just spending caps. Their systems allowed them to monitor performance in real-time and quickly identify and correct any issues.

What made this approach particularly powerful was that it enabled independent work without micromanagement. Team members could experiment confidently knowing that:

1. Systems were in place to catch major issues quickly
2. The focus would be on learning and improvement rather than blame
3. The organization valued the insights gained from experiments, even unsuccessful ones
4. Reasonable mistakes were viewed as part of the innovation process

For product managers looking to implement similar systems, Catherine’s experience suggests focusing on:

• Creating appropriate access controls without stifling creativity
• Implementing monitoring systems that catch issues early
• Establishing clear recovery procedures for when experiments go wrong
• Building a culture that separates mistakes from personal performance evaluation
• Designing redundancies into critical systems to prevent catastrophic failures

These systems didn’t just make innovation safer—they actively encouraged it by removing the fear factor from experimentation. This approach helped The Meet Group continue making innovative products over many years while building a reputation for creative solutions in a competitive market.

The “Kill Fast” Mindset

A “kill fast” mindset was essential to The Meet Group’s sustained innovation. This approach involved being willing to quickly end products or features that weren’t performing well, allowing the organization to reallocate resources to more promising opportunities.

The Meet Group maintained an “app graveyard”—an updated slide documenting all their discontinued standalone apps and features.

The team’s readiness to make decisive calls about what wasn’t working achieved:

• Quick resource reallocation: By killing underperforming products quickly, resources could be redirected to more promising opportunities
• Reduced attachment: Teams understood that each product was just one “shot on goal,” not a definitive measure of success
• Ongoing evaluation: Even successful features were regularly assessed for continued relevance
• Objective decision making: Data rather than emotions guided decisions about which products to continue supporting

Catherine shared how one of their features called “Match” (similar to the Tinder queue, but developed before Tinder existed) had been very popular and drove significant growth for years. However, when it eventually stopped performing well, the team was willing to acknowledge this and move on rather than keeping it alive out of sentiment or past success.

For product managers looking to implement a “kill fast” mindset, the key is creating clear evaluation criteria and regular review processes for all products and features. This approach requires:

1. Setting clear success metrics before launching new initiatives
2. Establishing regular review periods for all products and features
3. Creating a culture where sunsetting products is viewed as a success (you learned something) rather than a failure
4. Documenting discontinued products to preserve organizational learning
5. Celebrating both the launch and the ending of products as natural parts of the innovation cycle

The most valuable aspect of this mindset was recognizing that no single product determined the company’s success. By maintaining a portfolio approach with multiple “shots on goal,” The Meet Group could afford to kill underperforming products quickly while continuously developing new opportunities.

Learning Through Iterations

Catherine shared several examples of how iteration drove innovation at The Meet Group. She explained that their approach wasn’t about getting products right the first time, but rather about putting capabilities out quickly, gathering customer feedback, and making continuous improvements.

One of her favorite examples involved the evolution of a feature called “Battles.” This popular feature began as “Superlatives,” a yearbook-inspired concept where users competed for titles like “funniest” within their networks. When users provided direct feedback that they didn’t find the feature valuable, the team didn’t get defensive. Instead, they listened and recognized legitimate problems—the same people were winning the same categories repeatedly, making the experience stale and boring.

Rather than abandoning the concept entirely, they iterated by creating “Battles,” a one-on-one image contest between friends. This iteration transformed an underperforming feature into something significantly more engaging by addressing the core user complaints while preserving the competitive element that made the original concept appealing.

Another instructive example came from the team’s experience with video features. In 2012, they released a feature called “Live” that enabled one-on-one video chats with games like backgammon and checkers. Despite significant development resources, Catherine acknowledged that this feature did nothing interesting.

However, this apparent failure provided crucial learnings that influenced later successful products:

1. They discovered that most users were reluctant to appear on camera in one-on-one situations
2. They learned that playing simple games like backgammon with chat partners wasn’t compelling
3. They gained valuable experience with video moderation and identifying inappropriate content

These lessons directly informed their approach years later when developing a more successful livestreaming feature (also called “Live”). This time, they built it as a one-to-many feature rather than one-on-one, addressing the camera reluctance issue they had identified earlier.

The team also applied their trust and safety learnings from the earlier video experience. Catherine shared that they had discovered a correlation between faces visible in video streams and reduced instances of inappropriate content. This insight helped them develop more effective moderation systems for their later video products.

For product managers, the key takeaway is that iterations should be viewed as learning cycles. Each product version, successful or not, generates insights that inform future development. By embracing this perspective, teams can extract value even from unsuccessful products while continuously improving their offerings based on real user feedback and behavior.

Customer-Centered Innovation

Truly effective innovation must be grounded in deep customer understanding. Catherine explained how The Meet Group consistently put their users at the center of their innovation process rather than building features based on what the product team thought would work.

This customer-centered approach involved several key practices:

1. Regular user surveys: The team conducted frequent surveys to understand user pain points and preferences, not to determine exactly what to build next but to identify real user challenges.
2. Rapid deployment and feedback collection: Rather than trying to perfect products before release, they quickly deployed capabilities and gathered user reactions.
3. Direct incorporation of feedback: When users provided blunt feedback (like “this feature sucks” for their Superlatives feature), the team used this input to drive improvements.
4. Avoiding the “Tech Echo Chamber”: Catherine noted how important it was to resist the temptation to build features just because they were being discussed in tech circles.

Catherine explained that no user survey will explicitly tell you what to build next, but surveys can reveal actual pain points that users experience. By understanding these challenges, product teams can develop solutions that address real needs rather than perceived ones.

This approach helped The Meet Group avoid a common pitfall: building features that the product team wants rather than what users need. Catherine shared how they would use surveys to identify the gap between what they perceived as user pain points versus what users actually experienced as problematic.

For product managers, this customer-centered mindset requires:

• Regular, direct communication with users through multiple channels
• Developing systems to capture and analyze user feedback
• Creating quick feedback loops between user input and product iterations
• Maintaining skepticism about industry trends that aren’t validated by user needs
• Measuring success based on user-focused metrics rather than internal preferences

By keeping users at the center of their innovation process, The Meet Group was able to develop products that resonated with their audience even as market conditions and user preferences evolved over time.

Balancing Operations and Innovation

Catherine shared insights about navigating the tension between operational execution and innovation as organizations grow. She highlighted how traditional management approaches often prioritize efficiency and optimization, which can inadvertently push out the innovative spirit that fueled a company’s initial success.

One example Catherine provided was The Meet Group’s transition from web to mobile platforms around 2010. This transition presented significant challenges since the company had just gone public in a $100 million SPAC deal in 2011, with all their revenue coming from web properties. Public company investors typically expect consistent revenue growth, creating pressure to maintain existing business models rather than pursuing innovative directions.

Catherine explained that this critical juncture required balancing several competing priorities:

• Maintaining the existing web properties that generated current revenue
• Investing resources in mobile development with uncertain short-term returns
• Managing investor expectations during a period of strategic transition
• Shifting team focus and capabilities toward new platforms and technologies

The team recognized that despite having a successful web platform, mobile represented the future of social connection. For an app about meeting new people nearby, everyone having a GPS device in their pocket made perfect sense. The way people communicated through text messaging aligned perfectly with mobile experiences.

What made this transition successful was The Meet Group’s transparent communication with stakeholders. They clearly explained that investors would see declining web revenue for several quarters as users migrated to mobile apps where monetization hadn’t yet been fully established. Catherine emphasized the importance of educating investors about the long-term vision while acknowledging short-term performance impacts.

For product managers navigating similar transitions, Catherine’s experience highlights several key strategies:

1. Recognize when market and technology trends necessitate fundamental shifts
2. Communicate openly about expected “quarters of pain” during transitions
3. Create a compelling narrative around why change is necessary for long-term success
4. Balance resource allocation between current revenue generation and future growth
5. Use data to validate directional shifts while acknowledging short-term performance impacts

Catherine shared another example from later in The Meet Group’s journey when they made a significant bet on live streaming video in 2016. At that time, few companies were pursuing this approach in Western markets, though it was gaining traction in Asian markets like China with apps such as Momo. This represented another “bet the company” moment when the organization needed to balance current operations with forward-looking innovation.

Through these experiences, Catherine demonstrated that successful product organizations must continuously balance optimization of current offerings with exploration of new opportunities. The key is creating structures and communication approaches that allow both to coexist, even when they sometimes appear at odds with each other.

The Power of Storytelling in Innovation

Storytelling plays a critical role in gaining support for innovation initiatives. Product leaders must develop the ability to craft compelling narratives that help stakeholders understand the “why” behind strategic shifts and innovation efforts.

When The Meet Group was transitioning from web to mobile, transparent storytelling became essential for managing investor expectations. The team needed to communicate that while they would see declining web revenues as users migrated to mobile platforms, this short-term pain was necessary for long-term success. This required creating a narrative that helped stakeholders understand the future vision while acknowledging current challenges.

Catherine shared that effective innovation storytelling requires several key elements:

• Clear articulation of the vision: Explaining where the market is heading and why change is necessary
• Transparent discussion of trade-offs: Acknowledging short-term impacts while emphasizing long-term benefits
• Customer-centered perspective: Using customer stories to demonstrate why changes matter
• Data-driven foundation: Supporting narrative with relevant market and user data
• Emotional connection: Helping stakeholders feel excited about the future direction

Another example came from The Meet Group’s decision to build live streaming video in 2016. At that time, this represented a significant departure from their existing business model. Catherine explained that when presenting this direction to investors, they needed to focus on the story behind it and convince investors that the whole market would soon move toward live streaming.

For product managers, winning stakeholders’ hearts and minds is essential for successful innovation. Without effective storytelling, even the best product ideas may fail to gain the necessary support and resources. This applies to both external stakeholders like investors and internal team members who need to be motivated by more than just incremental improvements.

Catherine noted that engineers aren’t excited by instructions to add another penny to ARPU (Average Revenue Per User)—they want to understand how their work transforms the user experience and creates meaningful impact. By connecting innovation efforts to compelling stories about user problems and solutions, product leaders can inspire their teams while securing the organizational support needed for breakthrough innovation.

Actionable Strategies for Product Leaders

Catherine concluded our conversation by sharing specific strategies that product leaders can implement immediately to transform how their teams innovate. These actionable approaches don’t require organizational overhauls but can significantly impact innovation culture when consistently applied.

The first strategy Catherine emphasized was for product leaders to create structures for reporting experiments that didn’t go well, starting with themselves. By modeling vulnerability and openly discussing their own failed experiments, leaders establish psychological safety for their teams. This approach demonstrates that learning from failure is valued and expected within the organization.

Catherine suggested that product leaders should:

1. Create dedicated meeting time for failure discussions: Allocate specific time in regular meetings to discuss experiments that didn’t work and what was learned.
2. Establish a “learning from failure” framework: Develop a consistent approach for analyzing unsuccessful initiatives that focuses on insights rather than blame.
3. Celebrate meaningful learnings: Recognize team members who share valuable insights from failed experiments, reinforcing that this behavior is valued.
4. Connect experiments to customer impact: Always frame innovation discussions around how efforts ultimately affect customers and solve their problems.
5. Document and share learnings: Create systems for preserving insights from both successful and unsuccessful experiments so the organization builds cumulative knowledge.

Throughout our discussion, Catherine consistently returned to the importance of keeping customers at the center of innovation efforts. She stressed that bringing customer stories into product development discussions helps teams maintain focus on solving real problems rather than just building features.

Conclusion

Creating environments where product innovation thrives requires deliberate design and consistent attention from product leaders. As Catherine Connelly demonstrated through her experience growing MyYearbook into The Meet Group, successful innovation cultures combine psychological safety, structured learning from failure, customer-centricity, and a willingness to quickly redirect resources from underperforming initiatives. The most valuable insight from our conversation was that innovation requires regular action—taking multiple “shots on goal” rather than seeking perfection on the first attempt.

For product managers and leaders looking to transform their teams, Catherine’s advice offers a clear starting point: model vulnerability by discussing your own failed experiments, create dedicated structures for learning from what didn’t work, and keep customer needs at the center of all innovation efforts. By implementing these practices consistently, product teams can develop the resilience and creativity needed to deliver breakthrough products even as markets and technologies continuously evolve.

Useful Links

• Connect with Catherine on LinkedIn
• Get a free copy of Catherine’s book, Designing Success, just for Product Mastery Now listeners, and be sure to leave an Amazon review of the book
• Visit Catherine’s website

Innovation Quote

“Action is the foundational key to all success.” – Pablo Picasso

Application Questions

1. Learning from Failure: How could you restructure your team’s product review meetings to place greater emphasis on learning from unsuccessful experiments? What specific changes would make team members more comfortable sharing what didn’t work?
2. Psychological Safety: How could you demonstrate to your team that a person’s worth isn’t tied to the success of their ideas? What actions could you take in the next week to model vulnerability and create an environment where people feel safe proposing “dumb ideas”?
3. Kill Fast Mindset: How could your organization better identify and sunset underperforming products or features? What criteria or review process could you implement to make these decisions more objective and less emotional?
4. Customer-Centered Innovation: How could you bring more authentic customer stories and feedback into your product development process? What mechanisms could you create to ensure your team is solving real customer problems rather than building features based on internal preferences?
5. Risk-Free Experimentation: How could you create safeguards in your systems and processes that would allow team members to experiment more freely without risking catastrophic consequences? What specific changes would make innovation less risky in your environment?

Bio

Catherine Connelly is a marketing leader, entrepreneur, and author of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur.

Catherine co-founded The Meet Group, a NASDAQ-listed social dating and livestreaming company connecting millions of active users globally. The Meet Group was acquired in a $500 million sale in 2020. Catherine served as SVP of Marketing, leading marketing and communications across its portfolio of social entertainment apps and livestreaming and creator economy solutions.

Now, Catherine loves contributing to the entrepreneurial ecosystem through her weekly newsletter, Growing Up Startup, and her free office hours. Catherine graduated from Georgetown University and holds an MBA from The Wharton School of the University of Pennsylvania. To learn more about Catherine, visit https://www.cconnelly.me/.

Thanks!

Thank you for taking the journey to product mastery and learning with me from the successes and failures of product innovators, managers, and developers. If you enjoyed the discussion, help out a fellow product manager by sharing it using the social media buttons you see below.

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