The Leadership Dance: Navigating Leadership in Uncertain Times with Christina Hennington

Episode 14 of "The Leadership Dance," hosted by Alissa Hsu Lynch, features an insightful conversation with Christina Hennington, Executive Vice President and Chief Strategy and Growth Officer at Target. Released on April 2, 2025, this episode delves into Christina's journey from her Scandinavian roots to leading strategic growth initiatives at a global retail giant. Below is a comprehensive summary capturing the essence of their discussion.

1. Introduction

Alissa Hsu Lynch opens the episode by introducing Christina Hennington, highlighting her impressive tenure at Target since 2003. Christina's role encompasses ensuring Target's strategy remains cutting-edge, fostering strategic partnerships, and leveraging technology and generative AI to propel business growth. With accolades like "Merchandiser of the Year" by Women's Wear Daily and a recognized influence in retail, Christina brings a wealth of experience to the conversation.

2. Early Life and Scandinavian Influence

Christina shares her upbringing across Denmark, Norway, and Sweden, describing herself as a "Scandinavian mutt." Moving to the United States at eight years old broadened her horizons, sparking dreams of becoming an astronaut as she gazed at the stars from her snowy yard (02:09). This multicultural background instilled in her values of global citizenship, language proficiency, and a relentless work ethic. She emphasizes how her parents' multilingualism and global perspective shaped her ability to lead diverse, global teams today (02:34).

3. Career Journey at Target

Starting her career as a consultant at PwC, Christina quickly realized her passion lay in business strategy over technology. Her transition to Target occurred after returning to business school and being uniquely recruited as a buyer straight from Kellogg School of Management (07:05). Initially managing categories like sporting goods and toys, Christina found retail's fast-paced, consumer-centric environment exhilarating. Her journey at Target has been marked by diverse roles, including leading merchandising categories, overseeing major transformation efforts, and engaging in mergers and acquisitions, notably partnering with CVS for Target's pharmacies (09:43).

4. Leading During the Pandemic

Christina recounts being promoted to the leadership team in January 2020, just months before the pandemic reshaped the global landscape (11:12). As Chief Merchant, she navigated unprecedented challenges such as lockdowns, supply chain disruptions, and inflation. Emphasizing "clarity over certainty," Christina focused on establishing common assumptions to guide decision-making amidst chaos. She highlights the importance of maintaining safety and trust with consumers, which proved pivotal as Target's e-commerce platforms, including drive-up and same-day services like Shipt, scaled rapidly to meet soaring demand (12:15).

5. Current Role and Focus on Strategy & Growth

In her current role as Chief Strategy and Growth Officer, Christina steers Target's long-term strategic roadmap. She likens her team to a "compass for the organization" and "WD40," facilitating smoother and faster progression towards synchronized goals (16:11). Her focus areas include experimenting with innovative business models, leveraging technology, data science, and enhancing organizational efficiency to maintain competitive advantage in a rapidly evolving market (17:38).

6. Embracing Technology and AI

Christina discusses Target's extensive use of traditional AI for price optimization, demand forecasting, and personalization. She elaborates on the transformative potential of generative AI, highlighting applications like AI-aggregated customer reviews and internal tools aiding store team members in task management (21:11). These technologies enhance operational efficiency and customer experience, reinforcing Target's robust e-commerce and in-store presence. Christina anticipates further AI integration in call centers and marketing, balancing innovation with cost management (23:38).

7. Leadership Philosophy and Team Management

Christina emphasizes the power of teamwork, drawing from her athletic background and the collaborative nature of rowing (25:31). Her leadership approach centers on creating clear directions, empowering team members with necessary resources, and fostering a culture of mutual accountability and celebration. She advocates for embracing ambiguity, encouraging teams to navigate uncertainty with creativity and collective problem-solving. A poignant example from her tenure at Second Harvest Heartland showcases her ability to leverage diverse perspectives and creative solutions during crises (28:35).

8. Overcoming Barriers and Finding Superpowers

Addressing challenges, Christina reflects on her immigrant experience and being a woman in a predominantly male technology environment. She identifies her unique perspective and comfort with ambiguity as her superpowers, enabling her to empathize with underrepresented groups and navigate complex, uncertain scenarios effectively (29:56). Christina underscores the value of embracing differences to foster innovative thinking and inclusive leadership.

9. Mentorship and Networking

Christina acknowledges the critical role of mentors and sponsors in her ascent to the C-suite. She credits former senior leaders at Target and her involvement with the Henry Crown Fellowship and Aspen Institute for providing guidance, opening doors, and offering honest feedback (36:57). Emphasizing reciprocity, she strives to mentor others, advocating for paying it forward to build a supportive professional community.

10. Balancing Work and Personal Life

As a working mother of a 16-year-old daughter, Christina candidly discusses the challenges of balancing career and personal priorities. She prioritizes intentional time with her family, investing in meaningful friendships, and indulging in hobbies like skiing and woodworking to maintain personal well-being (41:20). Christina highlights the importance of grace and flexibility, acknowledging that achieving perfect balance is an ongoing process.

11. Advice to Younger Self

Reflecting on her career, Christina advises her younger self to embrace risks and address imposter syndrome head-on. She shares her initial feelings of inadequacy during the Henry Crown Fellowship and encourages leaning into opportunities despite self-doubt. Christina advocates for embracing personal growth opportunities and maintaining confidence in one's unique path to avoid future regrets (43:46).

12. Conclusion

The episode concludes with Alissa praising Christina as an inspirational role model and thanking her for sharing her leadership journey. Christina reciprocates the appreciation, emphasizing the mutual benefit of sharing stories and insights to empower listeners in their own leadership dances.

Notable Quotes

• Christina Hennington ([00:01]): “People often have a lot more regret around the things they didn't do than the mistakes that they made... It has allowed me a level of comfort with taking the next step for sure.”

• Christina Hennington ([02:09]): “I remember laying in snow... promising the stars I'd be there someday or the moon, that I'd be there someday.”

• Christina Hennington ([07:05]): “Retail was recruiting at Kellogg that year... I was the only one that they had hired with that profile.”

• Christina Hennington ([11:12]): “This idea of a rookie mindset... there's no right answer.”

• Christina Hennington ([16:11]): “My team is the compass for the organization and the WD40... how do we get there with less friction and faster?”

• Christina Hennington ([21:11]): “If you went on target.com today, you'd see that we have our reviews are aggregated by Genai to give you a summary of what consumers are saying about this product.”

• Christina Hennington ([25:31]): “This idea that you can do more with others is just fundamental to what I believe.”

• Christina Hennington ([29:56]): “I have a unique superpower of my own... comfort with ambiguity I think is a strength.”

• Christina Hennington ([36:57]): “I need to know that I can go to bed at night comfortable that I made the best decision or tried to do the right thing.”

• Christina Hennington ([43:46]): “Embracing it... it's a missed opportunity if you don't.”

Key Takeaways

• Global Perspective: Christina’s multicultural upbringing fosters a global mindset, essential for leading diverse, international teams.

• Adaptability: Transitioning from consulting to retail, and later into strategic growth, showcases Christina’s ability to adapt and thrive in varying roles.

• Leadership in Crisis: Her leadership during the pandemic underscores the importance of clarity, adaptability, and team cohesion in navigating crises.

• Technology Integration: Embracing AI and other technologies is pivotal for operational efficiency and enhancing customer experience in modern retail.

• Empowerment and Teamwork: Christina’s emphasis on empowering teams, fostering trust, and embracing ambiguity highlights effective leadership practices.

• Mentorship and Community: The role of mentors and structured networks like the Henry Crown Fellowship are instrumental in professional growth and success.

• Work-Life Balance: Intentional prioritization of personal life and self-care is crucial for sustained professional performance and personal fulfillment.

• Overcoming Imposter Syndrome: Acknowledging and addressing self-doubt can unlock potential and lead to meaningful career advancement.

Conclusion

Christina Hennington's journey is a testament to the power of embracing diversity, continuous learning, and resilient leadership. Her experiences offer valuable lessons for leaders navigating uncertain times, emphasizing the significance of adaptability, technological innovation, and fostering inclusive, empowered teams. This episode serves as an inspiring guide for individuals aspiring to choreograph their own leadership dance in the ever-evolving business landscape.