Purposeful, practical leadership coaching, training, and facilitation for the leaders carrying your work forward
Because stronger leaders fuel stronger organizations.
Leadership is deeply human work, and it deserves to be developed that way.
Work is one of the places where we humans spend most of our lives. It's where we connect with others, contribute to something larger than ourselves, and make a meaningful impact.
Yet most people have never been taught how to lead, whether that’s leading a team or organization in a formal management role, influencing informally, or even developing the self-leadership skill that’s necessary to navigate a modern career.
And in today’s ever-changing world, leadership is simply too crucial to be left to chance—that’s where I come in.
I’m Carole Ann Penney, Founder of Penney Leadership.
LEADERSHIP DEVELOPMENT COACH | TRAINER | FACILITATOR
At Penney Leadership, I grow leaders who know themselves deeply, lead with skill and intention, and create the conditions for their teams to thrive in a changing world.
As a Certified Professional Coach (iPEC) with over 15 years of experience developing leaders across industries, I’ve worked with thousands of leaders and organizations through individual and group coaching, workshops, and training. I also regularly write about career and leadership topics for publications including Harvard Business Review, Business Insider, and more.
My approach is grounded in the beliefs that work is fundamentally human, that investing in your leaders is the most effective way to strengthen your organization, and that leadership is an active practice that takes both skill and heart.
Trusted by
Invest in your leaders to strengthen your impact
The case for putting your leaders (especially your middle managers) at the center of your growth strategy
Everyone has a theory right now about how to build a more resilient, high-performing organization. Many of those theories focus on systems, technology, or structure.
But my approach, after 15+ years of developing leaders, focuses on something else: investing in the humans leading the humans.
Here’s my take on what it looks like to develop the managers closest to your people and your work, and the impact it has on moving your organization forward.
Coaching, training, and facilitation for stronger organizations and leaders within them
Work with Penney Leadership
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Leadership Coaching & Development
I partner with corporations and organizations through sustained, customized coaching that produces real change at both the individual and organizational levels.
Through 1:1 coaching and cohort programs, leaders develop both skillful leadership presence and a varied, practical toolbox that helps them meet the moment. The result is leaders who know themselves, lead with intention, and create the conditions for their teams to thrive.
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Workshops & Facilitation
For organizations looking to build leadership skills across a broader group or to bring skilled facilitation to a team offsite, I design and deliver experiences that are equal parts engaging, reflective, and actionable.
Sessions are tailored to meet your team’s specific needs, combining the latest in leadership strategy and thinking with real-world application. Participants walk away with practical tools they’ll use, perspectives they’ll integrate into their work, and culture-building connection generated through meaningful, shared experiences.
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"Carole-Ann is an expert strategic coach."
“She takes a highly personalized approach (no cookie-cutter advice), just genuine focus on your specific goals and trajectory.
Her structured methodology makes a huge difference. By pairing practical frameworks with custom visuals, relevant recordings, and curated articles, she turns complex corporate scenarios into a clear, actionable plan.”
- Sam Sarbaz
Strategy & Operations, Google -
"As a result of our coaching, I’ve developed more of a leadership voice and confidence around my approach."
“I’m more comfortable asserting my opinions and taking opportunities for visibility, and I’ve shifted my approach to individually coaching my team members.
My team is shining, and I’m seeing others respond to their leadership and influence. “
- Cliff
Insurance Team Leader
Ideas worth leading with
Explore original articles on leadership development, career navigation, and purpose-driven work
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What is Modern Leadership, Anyway?
Whether you’re a new or seasoned leader, this is your guide to modern leadership. Learn to develop and own your leadership with an introduction to these strategies, resources, and tools.
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New Managers: You Don’t Need to Know It All
It turns out that leadership isn’t about knowing it all. It’s about how you show up when you don’t know, and how you guide your team through with resilience and intention.
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Navigating Your Career Path With Intention
It’s time to leave behind the forward-and-up career expectation and trade it in for a career path that gives you the freedom to follow your curiosity, own your professional identity, and do work that’s meaningful to you.
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Join the Program
THE CAREER RESET COURSE
Learn to navigate your career with renewed clarity and intention inside the Career Reset Course, a self-paced program for individuals.
It’s all about exploring key mindsets and practical tools to help you define your own direction and recharge your momentum in the changing world of work. And after just a few weeks, you’ll be able to confidently move forward with intention and adaptability.
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Check Out Tools
RESOURCE LIBRARY
Let us be your source for practical, actionable guidance, so you can focus on doing your great work.
Inside the Resource Library, you’ll find Penney Leadership’s most popular guides and workbooks available for download, as well as a selection of original articles, expert podcasts, helpful books, and practical tools.
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Get the Newsletter
THE STRATEGIC LEADER’S TOOLBOX
Join the Penney Leadership community by subscribing to the Strategic Leader’s Toolbox, a monthly newsletter with exclusive insights and curated resources to help you navigate your work with intention and confidence.
Subscribers are also the first to know about new offerings, including when spots open up for individual coaching.