Individual and Group Leadership Development Coaching for Corporations and Organizations

Organizations are only as impactful as their leaders. Let’s develop yours.

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The world your leaders are navigating has never moved faster or asked more of them.

They’re feeling it. Here’s how to make sure they’re equipped for it. 

The world of work is changing, and it’s a challenge for organizations to keep pace.

Your managers are confronting shifting dynamics, rapid technological change, the pressure to do more with less, and an increasingly complex landscape of human needs at work—often without the development and support to match what's being asked of them. 

When companies feel that pressure, the instinct is often to look for structural solutions. And there’s no shortage of ideas right now of solutions to strengthen organizations, from operationalizing AI to flattening structures and streamlining processes.

But the variable that strengthens everything else isn’t structural: it’s human. 

It’s the quality of leadership within your organization, and especially within the middle of your organization, with the managers translating goals into action and leading the people doing it. 

Developing those leaders well—so they have the self-knowledge to manage themselves, the skills to develop others, and the support to keep growing—strengthens the whole operation. 

Good leaders fuel more effective teams, more effective teams get better results, and better results fuel the organization’s impact. That’s the kind of investment that not only pays off, but compounds.

I’m Carole-Ann Penney, Certified Professional Coach and Founder of Penney Leadership

Practical, purposeful leadership development coaching that produces meaningful change—right away, and into the future

At Penney Leadership, my coaching approach focuses on developing both leadership character and leadership skill so that leaders are ready to meet the moment. 

The work begins with deepening a leader’s self-knowledge—understanding who they are, what they stand for, and how they can best show up and effectively reach people. Because a leader's presence is amplified, the ability to skillfully manage their impact is essential. 

From that foundation, leaders can build a wide and varied practical toolbox: a range of real skills they can draw on to meet different people, moments, and challenges as they actually arise. That way, leaders move beyond their default or what’s most comfortable for them and instead respond with what’s most effective for the person and situation at hand. 

And because real change takes time, practice, and integration, every Penney Leadership engagement is sustained, customized, and woven into both your top-line strategy and the day-to-day work of your leaders. 

  • High-ROI impact for leaders, teams, and companies

    “Coaching with Carole-Ann provided me with new tools, clearer structure, and actionable accountability practices that are already shaping stronger, more sustainable leadership both for myself and my team. 

    It has allowed me to grow in meaningful ways and has equipped me to further develop our team, strengthening our foundation in a way that will benefit our company for years to come.”


    - Patrick Hauser, General Manager, Porsche Monmouth, Penske Automotive

Leadership Development Coaching for Organizations 

Meeting your leaders where they are, to prepare them to meet the moment

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1:1 Leadership Coaching

For organizations investing in the development of individual leaders, 1:1 coaching provides both the space and the structure where a leader can slow down, think clearly, and do the real work of growing.

Across weekly sessions (typically spanning three to six months), leaders have the opportunity to work on both the overarching goals they're building toward and their immediate challenges. 

Leaders come away with:

  • More skillful leadership presence—how they show up, what they project, and how to manage their impact with more intention—which shapes a more positive, effective team environment

  • Greater confidence and skill in navigating difficult conversations,  so that issues get addressed before they become problems, and people know where they stand

  • Increased resilience and the ability to navigate change, because uncertainty is inevitable and the skills to manage it are essential

  • More effective delegation, which frees a manager up to lead at the level their role requires while also meaningfully developing each team member’s skills and potential

  • The ability to build real accountability across their team as a consistent practice of clarity, follow-through, and trust, so that expectations are clear, people take ownership, and results become more consistent and more predictable

  • A practical toolbox of skills and approaches they can draw on long after the engagement ends, for leaders who are equipped to meet the moment both now and into the future

The result is development that shows up in how your people lead right now—and that continues to compound long after the engagement ends.

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Group & Cohort Coaching Programs

A custom leadership development program doesn't require a full internal team to pull it off—it just requires the right external partner.

Penney Leadership offers group and cohort coaching programs designed for your people and your goals, built and delivered end to end. From the initial conversation about what your organization needs and who it's for, through the design of the curriculum and the delivery of every session, each element is meaningfully customized for your group. 

Past cohort programs have brought together high-potential leaders from across departments, affinity and employee resource groups, managers within a single function, and more. Working from a proven model, the structure, cadence, and content are all customized for impact within your specific organization and context. 

Organizations that invest in cohort coaching report:

  • Meaningful individual growth as participants develop their own leadership presence, deepen their self-knowledge, and build practical skills they can use right away—so that every person leaves better equipped to lead

  • Stronger cross-functional relationships and a more cohesive internal network among leaders, so that collaboration happens more naturally, silos break down, and leaders who might never have worked together find themselves supporting each other's work

  • Higher satisfaction among high-potential leaders (which deepens your bench over time!), as investment in their growth is a powerful retention tool

  • A shared language and set of leadership skills across the organization as accountability, communication, and collaboration become more consistent across teams, and leadership stops feeling like something each person is figuring out independently

  • A culture of learning and development that participants carry back into their teams and departments, rippling the program’s impact outward into the organization

The research is clear: coaching pays off for organizations…

  • The average ROI of corporate coaching is 7 times the initial investment.

  • Organizations with coaching cultures report stronger leadership development and employee commitment.

  • 51% of businesses that work with coaches report higher revenue than their industry peers. 

  • 70% of leaders report improved work performance after coaching. 

*Sources: PriceWaterHouseCoopers, International Coaching Federation (ICF), Human Capital Institute, ICF

… And coached leaders agree.

  • "One thing I’m doing differently as a leader is being more present and involved with my team. Instead of just setting expectations, I stay engaged—checking in, asking questions, and supporting them through challenges. This has built more trust, helped us address issues faster, and kept everyone more focused and motivated."

  • "This program felt more real than other leadership training I’ve been through. It focused on the day-to-day challenges I actually face as a leader, and it pushed me to take action—not just listen and take notes. That made it more personal and a lot more effective." 

  • "All the leadership training I have done in the past has been in large settings and more generalized. With the one on one aspect of this program, Carole-Ann is able to focus on my specific needs and pinpoint areas of immediate opportunity so I could take action." 

Here's a look inside some recent individual and group leadership coaching engagements across a range of organizations and goals:

  • Four-month coaching and training program | Ivy League university research center

    When a leading research center needed to strengthen its senior leadership team, I designed and delivered a four-month program combining individual and team coaching with practical training tools built around the organization's real challenges. Leaders worked on both their individual development goals and the dynamics affecting the team as a whole, building the trust, communication, and shared leadership practices needed to move their work forward. By the end of the engagement, leaders had not only grown individually but were operating more effectively as a collective.

  • Cohort-based leadership accelerator | Biotech company

    A growing biotech company wanted to invest in developing high-potential employees as well as Employee Resource Group leads who were already doing significant yet unsupported leadership work. I designed a custom cohort program that brought both groups into a shared learning experience, building leadership skills, deepening self-knowledge, and creating a cross-functional network of emerging leaders. 

    Post-program assessments revealed a net promoter score of 9.3, with 91% of participants reporting that they would go through the program again. Where participants had previously rated their organization at a 6.6/10 for effectively supporting their advancement goals, that score rose to an 8.0 post-program, with leaders feeling more confident, more connected, and more committed to the organization.

  • Individual leadership coaching | Fortune 500 automotive company

    A Fortune 500 automotive company identified high-priority leaders across departments and invested in dedicated 1:1 coaching for each of them. Each engagement was fully individualized—built around that leader's specific goals, challenges, and growth areas—while I also served as a consistent thought partner to the Senior Vice President of HR on the themes and patterns of common challenges emerging across the group so we could address them. 

    The result has been meaningful individual development at scale (40 leaders and counting) that has become a cornerstone of the company’s leadership strategy. The program has filled a gap that periodic group leadership trainings weren’t closing—instead of delivering a curriculum that assumes where leaders are, my coaching meets them where they are. The company is deepening their leadership pipeline by growing leaders at different levels, leaving people prepared to step up with confidence and skill.

  • Custom workshop series | Ivy League university

    An Ivy League university wanted to build a sustained leadership development experience for its students and alumni: not a one-time training, but a series of sessions that built on each other over time and connected directly to what participants were navigating in their roles. I designed and delivered a custom workshop series tailored to the program's goals and the specific developmental needs of the cohort, combining practical skill-building with the kind of reflection and integration that fuels a real shift in how people lead.

Meet Your Leadership Development Coach and Trainer

Carole-Ann Penney, CPC

After 15+ years of developing leaders across industries and organizations, I keep coming back to the same conviction: 

Leading people to do great work is one of the most important—and complex—responsibilities there is.

A leader isn’t just accountable for outcomes and deliverables. They’re charged with the care of their team, whose growth, development, and sense of being seen and supported is shaped by how they show up. 

What I've seen, over and over, is that the most effective leaders are the ones who deeply know themselves—who understand how they land on others, who have done the work of getting clear on what they stand for, and who have built a varied enough toolbox to meet the moment with intention rather than defaulting to habit. And this level of insight and skill requires structured space to slow down and develop. 

This is why I believe that investing in your leaders is one of the most consequential things an organization can do. A leader who shows up with self-knowledge, care, and real skill creates conditions for positive impact that ripple through their team, their department, and the organization as a whole. In a world that keeps asking more of the humans doing the work, those conditions matter more than ever.

Leadership coach Carole-Ann Penney smiling. She is wearing a sleeveless plum top and headband. She is sitting at her desk, laptop, a mug of tea, and a bowl of blueberries in front of her.

Carole-Ann Penney, CPC
Founder | Leadership Development Coach | Writer | Trainer & Facilitator

  • Certificate in Professional Coaching, Institute for Professional Excellence in Coaching (iPEC) 

  • Senior HBR Facilitator for Harvard Business Publishing’s Corporate Leadership Development programs

  • Instructor at Electives

  • Contributor to Harvard Business Review

  • Certificate in Nonprofit Management & Leadership, Tufts University

  • B.A. in Education Studies, Brown University

  • "Participants reported greater confidence articulating their values and growth goals, and stronger skills to make those goals happen. 

    We hired Carole-Ann to design and facilitate a group coaching program for Employee Resource Group leadership. The survey feedback from participants speaks for the impact of the work, as well as Carole-Ann’s compassion and curiosity. The mix of her command of content—and true care—makes her incredible at what she does.”

    - Caroline, Senior Director, Biotechnology Industry

  • "Carole-Ann’s accessible training style connects research frameworks with the real life experiences of participants.

    When designing a new program around preparing mid-level managers to lead with greater emotional intelligence, I knew I absolutely had to bring on Carole-Ann. I’ve not come across anyone who creates such an inclusive, warm, and impactful learning space as she does.”

    - Erin Wederbrook Yuskaitis, Director, Learning & Development, Greater Boston Chamber of Commerce

Let’s transform your leaders—and your organization’s results—together.