Organizational Leadership Series with Kit Krugman, SVP People & Culture, Foursquare

Key Concepts

• Organizational Culture: The shared values, beliefs, and behaviors that shape how an organization operates.
• Velocity: The speed and momentum of a business's progress.
• Principles-Based Thinking: A leadership approach that relies on underlying principles rather than rigid processes to guide decision-making and action.
• Highly Aligned, Loosely Coupled: A framework where a clear high-level vision and context are provided, allowing individuals or teams autonomy in execution.
• Performance Improvement Plan (PIP): A formal process used to address underperformance, aiming to provide clear feedback and support for improvement.
• Continuous Feedback: An ongoing process of providing and receiving feedback, moving away from traditional annual reviews.
• Team-Based Performance: An organizational design that prioritizes the impact and success of teams over individual achievements.
• Network Analysis (O&A): A method of collecting data on influence, performance, and support within an organization using technology platforms.
• Builder Culture: An organizational environment that emphasizes hands-on contribution, innovation, and tangible output.
• Culture Fit vs. Culture Add: The distinction between hiring individuals who conform to existing norms versus those who bring new perspectives and challenge the status quo.
• Gender Equity: Ensuring fair treatment and equal opportunities for all genders within an organization.

Background and Early Influences

Kit Krugman's approach to people and culture work has been shaped by several pivotal experiences:

• Global Economic Downturn: Entering the workforce during a recession fostered humility, resilience, and a focus on adding value.
• Waitressing Experience: This taught foundational lessons in customer experience and team-based performance, particularly how pooled tips incentivized collaboration and shifted behaviors.
• Early Advertising Role: Despite being told her initial job of designing PowerPoint decks was going nowhere, Krugman advanced to run the creative department, highlighting the importance of communication in change and the potential to create opportunities.
• Columbia XMA Program: This program instilled a systems-thinking approach.
• Volunteer Organization Leadership: Leading a volunteer organization taught her how to craft a compelling value proposition that motivates individuals beyond compensation.

Mentorship and Leadership Inspiration

Krugman identifies three key influences on her leadership philosophy:

• Her Aunt: A powerful businesswoman and the first female corporate head of a New York City law firm, she modeled grace, confidence, and authority in leadership, demonstrating how to command influence without top-down control.
• Her Father: His role running IT at BU and his exceptional listening skills, characterized by direct eye contact and genuine attention, underscored the critical importance of active listening in leadership.
• Fantasy and Sci-Fi Literature: Reading books with strong female protagonists who develop their power and tackle increasing leadership challenges provides ongoing inspiration.

The Foursquare Chapter: Transition and Mandate

Foursquare, founded in 2009, initially began as a consumer app pioneering check-in technology and gamification. By 2011, it had achieved one billion check-ins. However, as gamification waned, Foursquare pivoted to a B2B model, leveraging its data for business insights, becoming the "geospatial layer of the internet." The company now serves apps, marketers, and advertisers with location-based data.

Krugman was hired as SVP of People and Culture after previously consulting for Foursquare at Co Collective. The initial conversation with CEO Gary involved a discussion about facilitating an all-company exercise on high-performance teamwork and introducing new leadership principles. During a subsequent meeting to discuss session design, Gary directly asked Krugman to join Foursquare.

The Mandate: Gary articulated that he had "overlooked the role that culture plays in transformation." He recognized that Foursquare's 13-year-old culture, reflective of its past business, was hindering its transition to a future-oriented B2B model. He sought an internal partner to drive this transformation, approaching it from an "internal change and transformation" perspective rather than a traditional HR one.

Krugman's reaction was a mix of excitement, intimidation by the unknown aspects of the role, and disbelief that it was actually happening.

Navigating a Stretch Role

Krugman's philosophy for taking on roles where she doesn't have a pre-existing formula is rooted in the belief that "you can figure it out." She emphasizes that learners can acquire almost any skill. Her approach includes:

• Leveraging AI: She famously used ChatGPT to generate a roadmap for a Chief People Officer's first year.
• Networking and Learning: She made it a mission to speak with as many people leaders as possible, adopting a strategy of making "five 20-minute calls" to gather insights and learnings, a method learned from Columbia Business School alumna Alfia.
• Rapid Skill Acquisition: She believes in the ability to "get smart fast" by talking to people, conducting research, and finding ways to become valuable quickly, even in unfamiliar territory.

Defining and Changing Culture

Krugman's definition of culture centers on "patterns of behaviors that are rewarding repeated patterns." She emphasizes that while often perceived as intangible, culture is fundamentally about observable behaviors.

The Culture System Framework

Krugman utilizes a framework that views an organization as a system, comprising interconnected elements:

1. Purpose: What the organization is trying to achieve.
2. Beliefs: The underlying values and assumptions (implicit or explicit).
3. Behaviors: The actions and rituals that stem from beliefs.
4. Systems: The structures, processes, and tools that support behaviors.
5. Rewards & Recognition: How behaviors are incentivized and acknowledged.

A breakdown in any part of this system can lead to misaligned behaviors. For instance, if safety is stated as important but not rewarded or incentivized, employees may not prioritize it.

Foursquare's Culture Shift: From Velocity Loss to Builder Culture

The primary mandate from CEO Gary was to restore "velocity" to the business. Foursquare had slowed down due to:

• Excessive Infrastructure: Large technology systems, processes, and management layers that no longer matched the company's scale.
• Internal Focus: More time spent managing internal processes and politics than shipping products.
• Lifestyle Business Tendencies: A shift towards prioritizing work-life balance over growth opportunities, signaling a lack of urgency and product delivery.

The desired new culture was one that emphasized speed, high performance, and a "builder" mentality.

Methodologies and Frameworks for Culture Change

Krugman implemented several key initiatives to drive this cultural transformation:

1. Principles-Based Leadership

• Core Idea: Moving away from rigid processes and towards guiding principles to enable faster decision-making and autonomy.
• Foursquare's Principles: Examples include "Get Going" (emphasizing speed) and "Highly Aligned, Loosely Coupled" (providing context and allowing for independent execution).
• Translating Principles to Action: The challenge is ensuring principles translate into tangible actions and behaviors. This requires aligning people systems with these principles.
• Critique of Traditional Engagement Surveys: Standard surveys often ask generic questions and don't probe whether employees have enough context to act quickly, a key aspect of being "highly aligned, loosely coupled."

2. Redefining Performance and Feedback

• Moving Beyond PIPs: Krugman advocates for a "post-PIP world" where clear, continuous feedback eliminates the need for formal performance improvement plans. She views PIPs as a sign of insufficient ongoing feedback.
• Eliminating Annual Reviews: Gary had already initiated the move away from annual reviews, recognizing their recency bias and tendency to halt organizational momentum.
• Implementing "Anytime Feedback": The risk of "anytime feedback" is that it can become "no time feedback" without the right systems and behaviors to support it.
• Addressing Individual Meritocracy and "Managing Up": The previous system overweighted individual merit and decision-maker opinion, leading to "managing up" rather than focusing on team impact.
• The "Messy" Performance System Audit: An audit revealed a fragmented system with anytime feedback, numerous PIPs, unclear career matrices, and calibration without sufficient data.
• Developing a Performance Philosophy: The need for a clear philosophy that informs pay principles, career matrices, and defined levels was identified.

3. Fostering Team-Based Performance

• Core Belief: "A high-performing team is more impactful than a team of high performers."
• Shifting Focus: The goal was to reward team output and impact, not just individual effort or quantifying effort over impact.
• Defining Team Behaviors: A framework was developed articulating four core team behaviors, directly tied to leadership principles.
• Integrating Team Focus Across Systems:
  • Career Matrix: Team behaviors were incorporated.
  • Hiring Questions: Interview questions were designed to assess alignment with team-oriented behaviors.
  • Coaching: Investment shifted from individual growth to highly facilitated team effectiveness coaching.
  • Team-Based Performance Evaluation: A tech platform (Confirm) was implemented for network analysis, asking questions like:
    • Who has influenced your work?
    • Who is a gold star performer?
    • Who would you flag for additional support?
    • This data provides a dynamic skills map and informs talent density discussions.
• Incentive Alignment: While not solely relying on incentives, the shift to team-based performance implied changes in how contributions were recognized and rewarded.

4. Organizational Restructuring and Flattening

• Engineering Team Example: Management was removed in the engineering team, with tech leads responsible for technical excellence within product pods. This was a deliberate choice to foster team effectiveness over traditional manager-employee relationships.
• Consequences: This led to a dip in perceived coaching and mentorship, prompting exploration of non-traditional methods, including AI-powered tools.

Data, Research Findings, and Statistics

• Velocity Increase: A self-reported 43% increase in velocity was observed within a year.
• Profitability: Foursquare achieved its most profitable year in history and its first profitable Q1 after implementing these changes.
• Inclusion Data: Engagement survey results consistently show 90%+ fair treatment across gender, race, identity, and ethnicity.
• Senior Leadership Representation: Strong representation of women in senior leadership roles.
• Maternity Leave: Krugman took her full four-month maternity leave, demonstrating support for parental leave at the executive level.

Key Arguments and Perspectives

• Culture is a System: Changing culture requires a holistic approach, addressing multiple interconnected elements, not just one aspect.
• Velocity is Crucial for Transformation: In a rapidly changing business landscape, regaining momentum and speed is paramount.
• Principles Over Processes: For agility, guiding principles are more effective than rigid, bureaucratic processes.
• Continuous Feedback is Key: Moving away from annual reviews to ongoing feedback fosters better performance and reduces the need for formal interventions like PIPs.
• Teams Drive Greater Impact: Prioritizing team performance over individual heroism can lead to more significant organizational achievements.
• Data and Human Judgment Complement Each Other: Performance evaluation requires both quantitative data and qualitative human judgment, applied at appropriate frequencies.
• Intentionality in Hiring: Focusing on "culture add" by seeking behaviors that contribute value and align with team orientation is crucial for scaling.
• Radical Change Requires Bold Leadership: Significant cultural shifts may involve difficult decisions, including potential attrition, and require leaders willing to embrace change.

Notable Quotes and Significant Statements

• "The culture of a company that has now been around for 13 years is a culture that reflects the business of the past. I need to bring the business into the future, and I need a partner who can help me do that from inside out." - Gary (CEO of Foursquare)
• "You can learn almost anything. And now, like the way that I the way that I thought about it, I feel I've never taken a job now that I knew how to do. But you can figure it out." - Kit Krugman
• "A pattern of behaviors that is rewarding repeated patterns." - Kit Krugman's definition of culture.
• "A high performing team is more impactful than a team of high performers." - Kit Krugman
• "We need to actually get things back in order and and go back to if I know, like I said, we need a performance philosophy and we need that performance philosophy to go into our pay principles." - Kit Krugman
• "It never goes to plan. I will just to be clear and you'll and you will always run into folks who are not satisfied with how you did it. No matter what change. That's a big learning." - Kit Krugman
• "Not every signal is one you need to listen to. You decide what signals you need to listen to in the context of what you're trying to achieve." - Kit Krugman
• "I think the culture fit one is always been a really interesting hot button because I think it's used in the right way and the wrong way. I think it's used to look for people that are like you, and I think that's really problematic." - Kit Krugman

Step-by-Step Processes and Methodologies

1. Initial Assessment and Audit:
   • Understand the current state of the organization's culture and systems (e.g., performance management).
   • Identify misalignments between stated principles and actual behaviors and systems.
2. Define the Desired Future State:
   • Articulate the core purpose and desired cultural attributes (e.g., velocity, builder mentality).
   • Establish guiding principles for leadership and operations.
3. Systemic Redesign:
   • Principles Integration: Ensure leadership principles are embedded in all people processes.
   • Performance System Overhaul:
     • Shift from annual reviews to continuous feedback.
     • Redefine performance to focus on impact and team contribution.
     • Implement team-based evaluation methods.
   • Team Effectiveness Focus:
     • Develop frameworks for team behaviors.
     • Integrate team focus into career matrices and hiring.
     • Provide team effectiveness coaching.
   • Organizational Structure Review: Flatten hierarchies and re-evaluate management roles where appropriate.
4. Implementation and Communication:
   • Develop comprehensive communication plans for all changes.
   • Roll out changes in a phased or prototyped manner (e.g., engineering team).
   • Gather feedback from executives, managers, and employees.
5. Measurement and Iteration:
   • Establish key metrics (e.g., velocity, profitability, inclusion scores).
   • Continuously collect data (e.g., through network analysis, surveys).
   • Analyze results and iterate on the system based on learnings.
   • Acknowledge that culture change is an ongoing evolution.

Synthesis and Conclusion

Kit Krugman's experience at Foursquare demonstrates a pragmatic and systems-level approach to transforming organizational culture. The core challenge was to shift from a legacy culture that had lost velocity to a future-oriented, high-performance "builder" culture. This was achieved not by focusing on a single initiative, but by redesigning interconnected systems: leadership principles, performance management, team dynamics, and organizational structure.

Key takeaways include the power of principles-based thinking to drive agility, the necessity of continuous feedback and team-centric performance evaluation, and the importance of bold leadership willing to make radical changes. Krugman's journey highlights that culture change is an iterative process, requiring constant measurement, adaptation, and a deep understanding of how beliefs, behaviors, and systems interact. The success at Foursquare, evidenced by increased velocity and profitability, underscores the tangible impact of a well-executed, systemic culture transformation. The ongoing evolution of their "builder culture" further emphasizes that culture change is a dynamic and continuous journey.