#19: Leading with Curiosity, Building Culture, and Finding Joy at Work

Overview

Anne Raimondi, COO of Asana, shares her insights on leadership, culture, and personal growth. Drawing from her experiences at companies like Zendesk and SurveyMonkey, as well as her role as a board member and educator, she discusses the power of curiosity, building resilient teams, integrating AI, and finding joy in work and life.

Notable Quotes

- The most impactful thing you can do is take responsibility for making the things and the people around you better—big or small, starting with yourself. – Anne Raimondi

- Ambition directed at the right things is super powerful. Ambition when it becomes internal competition can be destructive. – Anne Raimondi

- Everything doesn’t have to be done in a certain way. There’s freedom and joy in the messiness of it. – Anne Raimondi, on balancing perfectionism and family life

🌟 Curiosity as a Leadership Superpower

- Anne (Raimondi) describes herself as a problem solver, happiest when tackling complex challenges.

- She emphasizes curiosity as a key leadership trait, fostering continuous learning and collaboration.

- To solve the right problems, she advocates aligning on the problem’s scope, audience, and success metrics.

- Success is measured by the value exchange created for customers, whether through product adoption or meaningful feedback.

🤝 Building Advocacy and Resilient Teams

- Advocacy stems from creating meaningful impact for employees and customers, making them feel understood and supported.

- Anne highlights the importance of rallying teams around the customer’s voice, using direct feedback to inspire alignment and action.

- She stresses that high-impact individuals excel by delivering consistently and influencing beyond their job descriptions.

- Healthy ambition focuses on shared goals, while territorial behavior limits growth and scalability.

😂 Humor and Humanity in Leadership

- Anne believes humor and levity are essential in high-pressure environments, helping diffuse tension and foster connection.

- She shares examples of using self-awareness and humor to move conversations forward during intense discussions.

- Leaders should adapt their communication style to remain authentic while being effective in different situations.

🧠 Culture, Leadership, and Growth

- Anne defines culture as the intersection of mission, values, and norms, emphasizing clarity in decision-making and behavior.

- She advises evaluating a company’s culture by asking how decisions are made and whether values align with personal strengths.

- At Asana, leadership training focuses on conscious leadership principles, such as curiosity and accountability.

- She encourages aspiring board members to express interest, seek feedback, and align their unique skills with company needs.

🤖 AI and the Future of Work

- Anne notes that AI is reshaping how teams are built, reducing the need for repetitive tasks and enabling smaller, more innovative teams.

- She highlights the importance of fostering an AI-first mindset across all functions, empowering employees to integrate AI into their workflows.

- For those in resistant cultures, she recommends prototyping AI solutions to demonstrate their value and inspire adoption.

- AI amplifies the need for generalists and first-principle thinkers who can adapt and innovate continuously.