Leadership Development Workshops & Facilitation
Where insight meets application for lasting change
Your people are already full of insight, expertise, and potential. What’s often missing is the structure, the space, and the skilled facilitation to bring all of that to the surface—together, in a way that actually sticks.
That's the work I lead at Penney Leadership. Through custom workshops, leadership training, and facilitated offsites, I design experiences that meet your people where they are, 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 by strategic shared experiences.
Workshops & Training
Interactive leadership development experiences that advance employee engagement, build your bench, and strengthen your organization
The strongest organizations aren't built on strategy alone—they're built on people’s ability to lead, communicate, and work well together. Investing in that ability is one of the highest-leverage things an organization can do, and that’s the type of impact I love to support through well-designed workshops and trainings.
Signature Sessions
As the Founder of Penney Leadership and a seasoned facilitator and speaker, my approach is equal parts interactive, reflective, and actionable.
My talks and workshops draw connections between leading research and the expertise in the room so that participants walk away with both inspiration and implementable insights.
Below are some of my most requested sessions, and you can also browse the full Career & Leadership Training Menu for a wider selection of workshops.
Strategic Influencing: How to lead up, down, and across when you don’t have authority
Skill-building for professionals to lead effectively through influence rather than authority
Leadership isn’t just for the people with grand titles, direct reports, and formal authority.
In this interactive workshop, participants learn how to step up as a leader no matter where they sit in the hierarchy. We'll explore practical tools to lead at all levels and in all directions in order to support individual, team, and company success.
Participants will walk away with:
A clear understanding of what “managing up” means and why it’s critical to their success.
New mindsets on what leadership is.
Strategies to lead through influence no matter their role.
Four steps to influence and improve their relationships with their managers.
A Leading Through Influence Workbook to takeaway, which walks them through the steps of influencing a decision at work.
Building a Culture of Accountability
A practical process for the element of management many leaders find hardest
Accountability is one of the things organizations most want from their leaders, and that managers most want from their team members. But too often, people approach it as a one-time performance conversation rather than an ongoing process of clarity, support, and follow-through.
In this interactive workshop, participants learn a practical model that breaks accountability into three critical phases—including the parts leaders often overlook. Using a framework of actions to take at each stage, they’ll explore how to set clear expectations, provide the right support, and follow up in ways that empower their team.
Participants will walk away with:
A reframe of what accountability actually is, and why the way most leaders approach it makes it harder than it needs to be
A practical three-phase model they can apply to any accountability conversation or situation
Concrete strategies for setting clear expectations before issues arise
Tools for having the difficult follow-up conversations with more confidence and less dread
A framework for making accountability a consistent leadership practice rather than a last resort
Receive Feedback Like a Pro
Helping professionals transform criticism into fuel for success
There are countless trainings and articles out there to help managers effectively deliver feedback—but few focus on the receiving end of the conversation, despite how scary and emotional it can be.
In this interactive workshop, participants will learn to reframe their mindset about the role of feedback and learn how to manage their unique responses to criticism with resilience. We’ll explore three key questions you can ask to turn vague comments into actionable feedback—so that you become an active part of creating a quality feedback conversation.
Participants walk away with:
Guidance on getting into the driver’s seat of the conversation, instead of getting swept along on a wild and unpredictable ride.
Strategies to ask for the specific type of feedback they want.
A new framework to strategically integrate feedback to enhance their performance.
Tools to transform their response to criticism in order to be more resilient.
I’ve designed workshops and facilitated sessions for…
“Everyone left Carole-Ann’s session feeling ready to leverage actionable tools to strengthen their leadership paths and champion meaningful change in their lives!
Carole-Ann has a true gift for coaching, facilitation and teaching. She brings an unmatched spirit, energy, humility and rich knowledge to every engagement. Our members vary greatly when it comes to years of experience, industries and career challenges yet Carole-Ann was able to unite the group, connect with each audience member, and leave them with a greater understanding of what it means to live a life and career in total alignment to one's core values and ideology. We can't wait to bring her to the group again!”
– Carrie Majewski, Women in Leadership Nexus
Facilitated Offsites & Retreats
Build connection, create change, and ignite action
As the pace of work (and change!) only continue to speed up, creating space and structure to slow down is a strategic decision.
Every organization has moments that call for more than a meeting, whether you’re going through a period of significant growth, a leadership transition, a strategy that needs to move from “on paper” to shared conviction. The same is true within teams, when you need to rebuild trust, establish norms, begin to shift the culture, or get re-aligned before heading back into the work.
These are the moments that a well-facilitated offsite is designed for, and the times where the quality of facilitation is critical. After all, the agenda isn’t the only element that influences whether an offsite produces real momentum or quickly fades away. Having a guide in the room who knows how to draw people out, hold tension when it's productive, move the group forward when it's not, and design an experience that connects individual insight to collective action is essential.
That’s why I design and facilitate custom offsites and retreats for leadership teams, departments, and organizations. Every session is built around your specific goals, your team's dynamics, and the impact you’re hoping to create.
Tailored. Context is key. The Signature Sessions above have been some of my most-requested offerings, but I always curate—or build!—sessions around your particular audience and goals. You can inquire on behalf of a tight-knit department, large group, cross-functional team, slate of senior leaders, or any other group, and I’ll customize the content, format, and delivery accordingly.
Interactive. Effective training goes beyond presenting content. Whether it’s hosted virtually or in person, each workshop is strategically crafted to be engaging and interactive. Through structured exercises, facilitated discussion, and genuine connection between participants built in by design, the session becomes time well spent.
Actionable. Insight, ideas, and inspiration must be applied in order to produce real change. Every session gives participants the time and tools to connect new ideas to their actual work, so they can leave with something concrete to do differently.
What to Expect
Every leadership development workshop and offsite is…
“As a facilitator, Carole-Ann always shares her extensive breadth of leadership knowledge, but what’s far more impressive is her ability to make learning accessible and practical for leaders.
She inspires groups through her own example—creating a psychologically safe space that makes learners comfortable enough to try new skills, ask questions, and share wins and failures. One hundred percent of surveyed leaders in our program reported behavior change as a result of participating!”
- Christina Lewandowski, Sr. Leadership Development Lead, Arch Insurance
Carole-Ann Penney, CPC
Leadership Development Coach | Trainer | Facilitator
Meet Your Leadership Development Trainer and Facilitator
Carole-Ann Penney, CPC
As the founder of Penney Leadership, I coach individuals, teams, and organizations to deepen their leadership practice in order to take on pressing challenges. Through coaching, training, and facilitation, I guide leaders to develop the presence and the skills to be more engaged employees, more effective managers, and ultimately support more impactful organizations.
I hold a B.A. in Education from Brown University and certifications in Nonprofit Management & Leadership from Tufts University and Professional Coaching from the Institute for Professional Excellence in Coaching (iPEC). I mentor emerging leaders through Brown University's Women's Launch Pad, Social Enterprise Greenhouse, and the Institute for Nonprofit Practice. When I’m not coaching, I’m developing the most important emerging leaders in my life—my two young daughters.
Answering questions is my favorite thing to do.
You might be wondering:
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Yes! I regularly deliver both in-person and virtual sessions, and know how to facilitate genuine engagement whether we’re in a room together or spread out across the globe.
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I do! I’m based in Providence, Rhode Island and regularly travel for engagements. After you inquire, we can talk through some possibilities for travel.
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All pricing is custom depending on the needs and size of your audience, travel, planning needs, and level of the training.
After you reach out and we discuss your event, you’ll receive a proposal with detailed information about your customized session and investment.
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Absolutely. While the sessions described here are one-time workshops, we also offer a range of coaching and training programs for organizations. Please reach out if you’re interested in more sustained work with your company or team!
Empower your participants & strengthen your impact
Inquire About Workshops & Facilitation
At Penney Leadership, I design engaging, reflective, and practical virtual and in-person workshops for audiences at conferences, businesses, colleges, and organizations. Each workshop is tailored to your community’s needs. Sessions can be adapted to various time frames, and rates are customized for your event.
I’m looking forward to getting back to you!