We caught up with the brilliant and insightful Krupa Tailor a few weeks ago and have shared our conversation below.

Krupa, looking forward to hearing all of your stories today. Can you tell us about a time where you or your team really helped a customer get an amazing result?

Two years ago, one of my clients faced a crossroads during a company reorganization. Uncertain about her place in the organization and her career trajectory, she sought clarity and practical guidance but wasn’t sure where to begin.

Through our coaching, we explored her strengths, passions, and core values. This process allowed her to see herself more clearly and identify Product Management as a potential path—a field she had no prior experience in. Together, we created a roadmap to help her experiment with this direction while aligning her career aspirations with what truly mattered to her.

With this clarity and purpose, she secured her first Product Management role, doubling her salary and expanding her impact. Our coaching addressed everything from resume refinement and interview preparation to negotiating her offer with confidence. Alongside these tactical steps, we developed her authentic leadership style, enabling her to embrace her new responsibilities while staying true to her values.

This wasn’t just a career pivot—it was a transformation. By connecting self-discovery to practical career strategies and leadership development, she redefined how she saw herself and what was possible. Today, as she continues to excel, we’re refining her personal measures of success, ensuring her leadership aligns with her values and balances professional excellence with personal fulfillment.

This story highlights the power of self-discovery and clarity. When individuals see themselves holistically, they can move with confidence, intention, and impact, creating ripple effects in their careers and beyond.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m a career and leadership coach who helps individuals rediscover themselves, navigate pivotal transitions and lead with clarity, confidence, and alignment. My journey to coaching began with my own transformation. As COO of a pre-series A start-up, I achieved a title I had long aspired to, only to find it left me burned out, disconnected, and questioning what true success meant. That turning point led me to redefine my own path, and in doing so, I uncovered a deeper calling: helping others find fulfillment by aligning their careers and leadership with who they truly are.

At the heart of my work is the belief that leadership excellence starts with self-awareness. Whether you’re navigating your career or stepping into greater responsibility, success requires bridging external achievements with internal clarity. For career clients, this means practical strategies—refining resumes, preparing for interviews, or negotiating roles that reflect their worth. For leadership clients, it’s about developing an authentic style that aligns with their values while creating environments where teams can thrive.

Beyond one-on-one coaching, I facilitate community circles designed to foster connection and shared growth. These circles provide a space for individuals to explore who they are and be seen authentically by others. It’s in these moments of connection—whether with oneself or with others—that true growth happens.

What sets my approach apart is its holistic nature. Many people feel stuck not because they lack skills or ambition, but because they’re operating from outdated patterns, fear, or obligation. By helping clients reconnect with their values, embrace their full selves, and design a vision that reflects their aspirations, we unlock sustainable growth—both professionally and personally.

Over the past 2+ years, I’ve partnered with more than 50 clients to create meaningful transformations. They’ve secured new roles, increased their salaries, stepped into leadership with confidence, and built more fulfilling relationships with themselves and others. From redefining success to creating inclusive leadership practices, my clients leave with not just tactical skills but a deeper sense of purpose and alignment.

What I’m most proud of is seeing my clients flourish—not just in their careers but in their lives. There’s nothing more rewarding than watching someone rediscover their potential, lead with authenticity, and move through the world with greater clarity, confidence, and connection.

Have any books or other resources had a big impact on you?

My management and entrepreneurial philosophy has been profoundly shaped by a blend of books, frameworks, and practices that all center around a common theme: leadership starts with self-awareness, authenticity, and alignment. The resources that resonate most deeply with me reflect this ethos and continue to influence how I support my clients in their growth journeys.

Brené Brown’s work on vulnerability and courage has been a cornerstone of my approach to leadership. Her insights on daring to lead with heart, embracing imperfection, and fostering trust have fundamentally shaped how I help clients step into leadership with authenticity. She reframes vulnerability as a strength, not a weakness—a concept I’ve seen transform how leaders connect with their teams and themselves.

Shakti Gawain’s Creative Visualization introduced me to the power of mindset and intentionality. Her teachings have been instrumental in helping me—and my clients—reframe challenges and align with visions of success that are expansive yet deeply personal. It’s a reminder that the reality we create begins with the thoughts and beliefs we cultivate.

James Clear’s Atomic Habits has provided a practical framework for understanding change. His principles of building habits, making incremental improvements, and creating systems for sustainable success are tools I frequently draw on when helping clients create growth that lasts—whether in their careers, leadership, or personal lives.

The principles of design thinking, pioneered by IDEO, have significantly influenced my perspective on problem-solving and innovation. By focusing on empathy, experimentation, iteration, and creativity, design thinking provides a framework not just for finding solutions but for cultivating environments where exploration and collaboration thrive—whether in organizational leadership or personal development.

Recently, I’ve deepened my exploration into somatic and breathing practices, discovering the profound interconnectedness of the mind, body, and soul. These modalities add another layer to my work, enabling clients to process emotions, ground themselves, and access their intuition in ways that extend beyond traditional cognitive approaches. By integrating somatic awareness with strategic tools, I guide clients toward holistic and sustainable transformations that honor their full selves.

Together, these resources and practices form the foundation of my philosophy: growth is not a rigid climb but an organic, iterative process rooted in alignment, intention, and well-being. By embracing this perspective, I help clients move with clarity and confidence, creating lives and careers that feel authentic and impactful.

Can you share a story from your journey that illustrates your resilience?

Resilience has been a constant theme in my entrepreneurial journey—something I lean into every day. It’s not a one-time story but an ongoing practice, an essential part of navigating the ups and downs of building something meaningful.

This isn’t my first venture. Over a decade ago, I set out to create a peer-to-peer clothing rental platform for South Asian clothing. I saw a gap in the market and felt compelled to fill it. The concept gained traction, and investors even showed interest in helping me scale. But at the time, I hesitated to seek outside funding. I wanted to retain full ownership of my idea and protect my vision. Looking back, I see that desire for autonomy was important to me, but it also meant I carried the weight alone. Eventually, I decided to pause that venture, but the experience left me with invaluable lessons—about trusting my instincts, learning from setbacks, and embracing the unknown.

Over the past 10 years, I’ve always had something brewing—ideas, experiments, projects—all reminding me that building something impactful was still part of my journey. But it wasn’t until two years ago that I took the leap into full-time coaching. This decision came with its own set of challenges, and there were many moments of uncertainty when I wasn’t sure if this would work out. But resilience, for me, wasn’t about having all the answers; it was about showing up every day and taking steps forward, even when the path wasn’t clear.

Resilience isn’t about being unshakable; it’s about embracing change and taking risks, no matter how uncertain the future may feel. It’s about trusting that the work I’m doing matters, even when the results aren’t immediate, and knowing that the journey, with all its twists and turns, is part of a larger story. Every step, whether a win or a lesson, is fuel for the next.

For me, resilience is a continuous commitment—one that I draw on daily to stay aligned with my purpose. It’s about trusting the process, believing in what I’m building, and knowing that every setback is an opportunity to learn and grow.

Contact Info:

• Website: https://www.krupatailor.com
• Instagram: @kruptail
• Linkedin: https://www.linkedin.com/in/krupa-tailor/

Image Credits

Elena Kosharny