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Madelyn Sierra

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Founder and Coach, Sierra Executive Advisory


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Madelyn has a global practice that ranges from Fortune 100 companies to start-ups.


A Harvard MBA, Madelyn leverages her knowledge of business and organizational dynamics to quickly understand client issues. She combines that with an ability to listen deeply to her clients, challenge their perceptions and provide a supportive and dynamic environment to achieve their goals. Clients describe Madelyn as impactful and success-oriented, someone who quickly inspires trust and partnership and helps them leverage their potential for growth.


Madelyn coaches clients on:

  • Organizational change
  • Communicating a strategic vision
  • Leading others
  • Influence and persuasion
  • Executive presence and personal branding
  • Team development


She launched and managed Harvard Business Publishing’s virtual leadership development program, designing and delivering programs to more than 1,000 global executives within a three-year period. After graduating from Harvard Business School, she held management positions in marketing, healthcare, corporate education, and real estate development.  


What coaching services do you provide?

I provide individual and team coaching, meeting facilitation and workshop, and leadership development delivery.


What services do you provide in addition to coaching?

I provide resume review and interview prep.


What is your coaching philosophy?

Most clients I work with are typically clear on the areas they have to address. I help my clients clarify their goals and develop a plan of action to achieve them. I'm supportive, direct and challenging.


What interests or excites you about coaching women lawyers?

Women often face greater challenges in advancement than their male counterparts. Whether it's confidence, work-life balance, focusing on their brand, or increasing their sphere of influence and network, I find helping them reach their full potential very satisfying.


Tell us about your training and certifications as a coach.

I have completed my professional coaching training at Goldvarg Coaching, I have a PCC and also completed a certificate in organizational development at Columbia University Teachers College.