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What does it truly mean to lead authentically in today's corporate landscape? Kim Seymour, a seasoned executive with decades of leadership experience, breaks down this question with refreshing clarity and hard-won wisdom.

"Leading people in a way that is sustainable for you, that you can believe in" forms the cornerstone of authentic leadership, according to Seymour. But this isn't just about showing up as your unfiltered self. Throughout this powerful conversation, she reveals the delicate balance between bringing your authentic voice to the table while understanding the ecosystem you're operating within.

Drawing from her impressive career journey, Seymour shares three essential unwritten rules that have guided her success: "Relationships are everything," "Always stay curious," and "Feedback is not optional." These principles aren't just platitudes—they're practical guideposts for navigating complex organizational dynamics while maintaining your integrity.

Perhaps most valuably, Seymour challenges conventional wisdom about the crucial first 90 days in any new role. Her counterintuitive advice? "Go hard for the first six months, then you never have to go hard again." This approach establishes your reputation and creates what she calls a "flywheel effect," where your initial investment continues generating momentum long after those intensive first months.

The conversation takes a particularly meaningful turn when discussing vulnerability in leadership—a quality that emerged as a superpower during pandemic challenges. Seymour reflects on how leaders who could blend strategic thinking with emotional intelligence created psychological safety while still delivering results during unprecedented uncertainty.

Whether you're just beginning your career journey or sitting in the C-suite, this episode offers invaluable insights on defining success on your own terms. As Seymour powerfully states, true success means having options—the freedom to choose your path forward rather than feeling trapped by circumstances. Subscribe now to continue growing as an authentic, effective leader who remains true to their core values.

Drive, Ambition, Doing, Leading, Creating... all good until we forget about our own self-care. This Village of All-Stars pays it forward with transparency about misses and celebration in winning. We cover many topics and keep it 100. We are Proven Not Perfect™️
https://www.provennotperfect.com

Follow me on Instagram at: shontrapowell_provennotperfect
Check out Proven Not Perfect ™️ YouTube Channel as well. Join the community for ideas and events at www.provennotperfect.com.

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Maggie O’Brien is Managing Director - Co-Head of Chicago at J.P. Morgan Private Bank. She is a Daniel Burnham Fellow member of Leadership Greater Chicago, the region’s premier civic leadership organization. Complementing Maggie’s offer as a corporate and community leader, she is a mom and wife, committed to the love and advancement of her family. This conversation is ‘real’ and ‘raw’, getting deep into the reality of a PROVEN woman leader who navigates her journey with resilience, mindfulness and authenticity.

Maggie never expected to be pulled over on the side of a road for our conversation about female empowerment, but as she puts it - "such is the life we lead." This unplanned moment perfectly captures the reality of being a working woman balancing career ambitions with family responsibilities.

From the earliest days of her finance career, Maggie questioned whether she belonged in the room. At 23, walking into meetings with manufacturing executives, she wondered why they would ever listen to her advice. This vulnerability around confidence, especially for women in male-dominated fields, becomes our central theme. The conversation reveals how women often need significantly more certainty before taking risks compared to their male counterparts - a hesitation that can hold us back from opportunities for growth.

The turning point in Maggie's confidence came after successfully turning around an underperforming team, giving her tangible proof of her capabilities. Yet even successful leaders face setbacks. Her most valuable leadership lesson came from a failed turnaround where feedback revealed she'd been perceived as a "bulldozer" who hadn't taken time to understand the team before implementing changes. This taught her the essential principle that "you've got to get people in the boat with you before you ask them to row."

For women whose confidence has been shaken, Maggie recommends cultivating a personal "cheerleading squad" - trusted friends who genuinely see your value and can remind you of it during difficult times. This becomes increasingly important as leadership positions become more isolated, with positive reinforcement growing scarce.

The parallels between professional confidence and financial empowerment are striking. Women approach money decisions with similar caution, yet 80% will need to manage family finances at some point. For young women entering finance careers today, there's reason for optimism as technological advances make work-life balance more achievable, but representation remains critical - we need to see women who've successfully balanced career advancement with family life to believe it's possible for ourselves.

Listen for practical wisdom on developing self-advocacy, overcoming imposter syndrome, and finding your own power outfit (Maggie's is a hot pink Veronica Beard suit) that helps you own your presence in any room.

Drive, Ambition, Doing, Leading, Creating... all good until we forget about our own self-care. This Village of All-Stars pays it forward with transparency about misses and celebration in winning. We cover many topics and keep it 100. We are Proven Not Perfect™️
https://www.provennotperfect.com

Follow me on Instagram at: shontrapowell_provennotperfect
Check out Proven Not Perfect ™️ YouTube Channel as well. Join the community for ideas and events at www.provennotperfect.com.

I'd love to hear what you think!

Send us a text

This episode explores the complex realities of caregiving, focusing on the sandwich generation—the caregivers juggling responsibilities for both their children and aging relatives. With insights from Sue Ryan, we discuss self-care strategies, workplace transparency, and the importance of community support in navigating this demanding journey.
• Understanding the sandwich generation and its pressures
• Importance of transparency in caregiving within the workplace
• Strategies for self-care as essential for caregivers
• The role of community support and accepting help
• Introducing the Caregiver's Journey initiative for resources and guidance

Drive, Ambition, Doing, Leading, Creating... all good until we forget about our own self-care. This Village of All-Stars pays it forward with transparency about misses and celebration in winning. We cover many topics and keep it 100. We are Proven Not Perfect™️
https://www.provennotperfect.com

Follow me on Instagram at: shontrapowell_provennotperfect
Check out Proven Not Perfect ™️ YouTube Channel as well. Join the community for ideas and events at www.provennotperfect.com.

I'd love to hear what you think!