Meet Karen Stein
After more than 30 years in professional services, including 24 years as a Deloitte partner, I became fascinated by one of the most important leadership transitions of all: midlife.
It is often the stage where successful leaders begin asking different questions. Questions about identity, purpose, confidence, relevance, energy, relationships, and what comes next.
Some are navigating organisational change. Some are managing life-stage biopsychosocial changes like menopause. Others are adapting to new technologies, changing family responsibilities, health challenges, or shifting priorities. Many are trying to work out how to remain engaged, relevant, and fulfilled while continuing to make a meaningful contribution.
Today, through executive coaching, keynote speaking and my Midlife Leadership Series, I help leaders navigate these transitions with greater clarity, confidence and intention. My work focusses on organisational systems, midlife transitions, and creating sustainable careers.
I bring conversations to organisations that are typically left at home - those of midlife identity, meaning and mattering; menopause in the workplace and having your unfair share of midlife women talent; midlife decisions regarding motivation, longevity at work, role changes and impact.
Lets talk about what is not simply a personal issue, but is a business, leadership and wellbeing issue. My professional experience, leadership and technical training offer a unique perspective which resonates quickly with audiences.
My Why
I believe too many talented people lose confidence, disengage, or quietly step back at exactly the point when they have the most experience and wisdom to offer.
Midlife should be one of the most rewarding stages of a career for all leaders.
My work helps leaders sustain momentum, strengthen their confidence, continue learning, deepen connection, and create meaningful next chapters.
I am particularly passionate about supporting women through perimenopause and menopause, helping individuals and organisations navigate a life stage that too often remains misunderstood or unsupported. I am M.A.D about menopause (making a difference in the workplace).
When leaders are supported through midlife, individuals thrive, organisations benefit, and everybody wins.
My Accomplishments
• 30+ years in professional services leadership, including 24 years as a Deloitte partner • Designed and delivered Deloitte’s Women Partner Coaching Program for close to a decade, coaching many hundred partners, with high Net Promoter Scores • Over 2500 Executive Coaching hours • Creator of The Midlife Leadership Series: Midlife Momentum™ M.A.D about Menopause™ (making a difference in the workplace) and Midlife mastery: The Next Chapter™ workshops and keynotes, executive coaching and group coaching • Author of the international award-winning book 'Be Your Own Leadership Coach (self coaching strategies to lead your way)' • Highly acclaimed keynote speaker and panelist • Master of Science in Coaching Psychology, Master of Laws, and Professional Certified Coach (PCC). Accredited Mental Health First Aider, Hogan Psychometrics, Mental Toughness Accredited, Capfinity Strengths Profile Accredited. • Menopause Champion, Certified Menopause Coach and Independent Panel Assessor for Menopause Friendly Australia • Co-founder of Deloitte's Managing Menopause in the Workplace Working Group, and Group Coach for managing menopause at work • Known for practical, evidence-based work that builds confidence, clarity, and career longevity
Fun facts
1. Karen’s three favourite P’s are Pilates, pickleball, and parkruns. Balance matters.
2. She learned to ski on the slopes of Korea in January - proof it is never too late to try something new.
3. Her love of learning led her to complete a Master of Science in Coaching Psychology, because great coaching deserves rigour.
4. Karen is a proud mum to two fabulous sons who keep her firmly connected to Gen Z thinking and language.
5. Her very first job was as a clown at children’s birthday parties; an early lesson in energy, presence, and reading the room.
6. She recently retired after 24 years as a partner at Deloitte, becoming the second longest-serving woman partner.
7. Her second book is officially underway, continuing her commitment to helping leaders thrive through change.
How I can help
Sustaining confidence, momentum, and leadership impact through midlife
Helping leaders remain relevant, adaptable, and engaged in a rapidly changing world
Supporting successful professionals to navigate transitions, identity shifts, and career crossroads with greater clarity and intention
Supporting individuals and organisations to better understand and navigate menopause as part of a sustainable leadership career
Strengthening self-awareness, connection, and self-belief so leaders can lead as their best or better selves
More from Karen Stein
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Profile information supplied through Cuppa’s talent directory. Availability and suitability are confirmed on enquiry.