Transformative Leadership Coaching & Training for Organizations

Empower your leaders and elevate your impact

Do what you do best even better with coaching.

The world of work is constantly evolving, and so is your organization. But whether you’re focused on driving innovation, deepening your impact, or developing high-functioning teams, the common denominator remains: Effective and impactful leadership at all levels is crucial.

Leadership, like any other professional skill, can be cultivated, honed, and refined—and that’s where expert coaching makes all the difference. 

Investing in coaching for individuals, teams, or cohorts helps to: 

  • Fast-track individual leadership development, using the latest evidence-based methods and tools that can be put into practice right away. 

  • Gain new insight and perspective, from an expert and external coach who creates opportunities to reframe challenges and take action. 

  • Build emotional intelligence within your organization, heightening leaders’ ability to effectively influence and inspire others.

  • Establish a sustainable leadership framework, developing a more consistent approach across the organization.

  • Try adaptable approaches to team development, helping to build a collaborative and more effective work environment. 

Research shows that leaders who have been consistently coached*:

Outperform peers by

27%

Apply more effort

+18%

Are more promotable

11%

Are less likely to leave

+25%

Training information retained

4x

Are significantly more engaged

+25%

*Sources: Integrity Solutions, Sales Executive Council, Gallup, Hay Group, Harvard University, Goleman & Boyatzis

Leadership Coaching & Training for Organizations 

Across companies, industries, and levels of leadership

Individual, Team, and Cohort-Based Coaching

For individual leaders and managers, 1:1 coaching provides a neutral, productive space to deepen leadership skills, navigate transitions, and address specific role-related challenges and opportunities. Team and cohort-based coaching is ideal for fostering a culture of learning and growth, building organizational cohesion and strengthening performance. 

Comprehensive Support for Leaders at All Levels

We recognize that leadership development needs vary at different career stages. We have expertise in tailoring programs for:

Emerging leaders, emphasizing foundational leadership skills and developing leadership identity formation

New managers, honing their team management, communication, and decision-making skills

Mid-level leaders, exploring strategies for expanding their influence and leading larger teams and projects

Senior executives, delivering advanced coaching to enhance their strategic thinking and organizational impact.

Flexible Coaching and Training Programs

Our approach is adaptable and accessible, as we regularly develop both comprehensive, long-term programs aligned with your strategic objectives as well as targeted, daylong workshops and off-site retreats. Through both in-person and virtual engagements, we’ve worked with clients around the globe to coach leaders and train teams.

  • Inclusive & Accessible Training

    “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 to lead two sessions. Her accessible training style connects research frameworks with the real life experiences of participants, and I’ve not come across anyone who creates such an inclusive, warm, and impactful learning space as Carole-Ann.”

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

  • Transformative Coaching Sessions

    "Carole-Ann's coaching sessions are not just transformative; they're eagerly anticipated milestones. Her accessible presentation style, adaptability, and depth of wisdom create an engaging experience that lingers long after each session concludes."

    Rachel Wilson
    Assistant Director of Mentorship Programs
    Office of Alumni Relations, Brown University

  • Custom ERG Coaching Program

    "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, and the compassion and curiosity of Carole-Ann. Participants reported greater confidence articulating their values and growth goals, and stronger skills to make those goals happen. The mix of her command of content—and true care—make her incredible at what she does.”

    Caroline M.
    Senior Director
    Biotechnology Industry

  • Practical Leadership Knowledge

    “As a facilitator for Arch’s Boost leadership program over the past four years, 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 Arch leaders participating Boost reported behavior change as a result of participating in the program!”

    Christina Lewandowski
    Sr. Leadership Development Lead
    Arch Insurance

Curious about what working together could look like?

Our engagements have included:

  • Designing and facilitating a daylong offsite leadership development training for a leading confectionery company, building cohesion across department’s leaders of all levels 

  • A four-month team and individual coaching program for senior leaders at an Ivy league university research center, incorporating training tools that are immediately applicable to organizational challenges

  • A cohort-based leadership accelerator program at a biotech company, supporting the development and retention of high-potential employees and Employee Resource Group (ERG) leads

  • Individual leadership coaching for hand-picked leaders across departments at a Fortune 500 automotive company

  • Developing a custom workshop series for emerging leaders at an Ivy league university, training and coaching on key topics that align with program goals

Inside Penney Leadership

Carole-Ann Penney, CPC

Founder & CEO | Leadership Trainer | Strategic Career Coach

Carole-Ann Penney helps mission-driven leaders navigate their careers with purpose and resilience. As the Founder of Penney Leadership, she guides professionals to step into their authentic leadership and build their toolbox of mindsets, skills, and resources to make a meaningful impact.

A seasoned writer, speaker, and facilitator (in-person and virtually) on topics related to leadership and career development, Carole-Ann works with individuals and organizations across all sectors, industries, and roles. She is a Senior HBR Facilitator for Harvard Business Publishing's Corporate Leadership Development programs and an instructor for Electives, training professionals across the globe. Carole-Ann has led sessions for Fortune 100 corporations, higher education institutions, small businesses, nonprofit organizations, philanthropic foundations, and professional associations, and her writing has been featured in Harvard Business Review. 

Carole-Ann holds a B.A. in Education from Brown University and certifications in Nonprofit Management & Leadership from Tufts University and Professional Coaching from iPEC. She also mentors emerging leaders through Brown University's Women's Launch Pad, Social Enterprise Greenhouse, and the Institute for Nonprofit Practice. When she is not coaching, she’s developing the most important emerging leaders in her life—her two young daughters.

Our Coaching & Facilitation Philosophy

These core beliefs are at the heart of everything we do:

  • Commitment to diverse perspectives and individual experiences.

    Coaching is not teaching, advice-giving, or mentoring. We believe that each participant comes with unique strengths, values, and challenges, and there are no one-size fits all answers. We specialize in creating a space and structure that allows participants to make their own discoveries and connections that are individualized and meaningful to them.

  • Interactive, participatory approach that connects leading research with real life.

    Our facilitation approach draws connections between research and the expertise in the room. We honor participants’ lived experiences while challenging them to consider fresh perspectives and approaches.

  • Ideas and inspiration aren’t enough—it’s all about actionable, practical applications.

    Each session gives participants the time and tools to reflect on their own experiences and to personalize and integrate new approaches to advance their work.

  • Moving beyond one-time fixes to tools that foster long-term professional growth.

    Program tools are designed to be evergreen so that participants can revisit them again and again, forming growth-oriented habits that will serve them throughout their careers.

Let’s elevate your organization and transform your leaders together.

Now booking for projects in 2025!