Leadership Coaching for Individuals

For professionals who are ready to lead with more intention, more impact, and more of who you authentically are

Thank you for your interest in coaching! The Penney Leadership practice is currently full and individual coaching spots open infrequently. When spots do open, I’ll announce it via my newsletter, The Strategic Leader’s Toolbox.

Leadership is more expansive than many people think. 

Whether you’ve managed a team for years, you’re a new leader, you lead informally through influence, or you’re an individual contributor navigating your own career… that’s all leadership.

And most of the challenges that you face at work—how to navigate a difficult relationship with your manager, how to position yourself for what’s next, how to lead a group through something complicated—are, at their root, questions of leadership. 

Once you see them that way, the path forward opens up!

Because, like many of the skills that got you here, leadership is a skill that you can develop intentionally.

Leadership is a practice, one that you’re able to authentically develop from wherever you are and continuously apply to how you navigate your life and career. 

It’s not about "knowing it all”—it’s about how you’re prepared to show up when you don’t know. It’s about honing your ability (and developing the self-trust) to make consistent, confident decisions for yourself and with your team. 

And whether you’re seeking support to manage people more effectively, lead a project that’s never been done before, or show up in your work more strategically and authentically, leadership coaching can help. 

Leadership Coaching with Penney Leadership

Practical, purposeful support for leaders at all levels

Coaching is fully customized to your goals, strengths, and challenges. 

There’s so much that you already bring to the table, like your expertise, your drive, and your track record. There are also likely some changes you’d like to see: maybe you’re trying to shift how you’re perceived, strengthen your ability to influence others, or figure out how to lead with more confidence and less second-guessing. 

That’s why we start by getting clear on your values: what you stand for, what drives your decisions, and what kind of leader you most want to be. Your values are the foundation that shapes everything that follows. 

From there, coaching becomes a personal container for thinking, skill-building, and problem solving. As we meet, you have a confidential, strategic, reflective space to work through what’s most pressing, examine what might be getting in your way, try on new approaches, and debrief about what happened when you put them into practice. I bring in relevant tools, frameworks, and resources as they become relevant: not as a pre-set curriculum, but as curated support for the specific work you’re doing. 

And between sessions, you integrate those ideas and insights from coaching into your work. You try something, notice what happens, and bring it back to talk through together. Over time, that cycle of reflection and practice is what produces real, lasting change. 

Three overlapping circles in pastel purple, blue, and dark gray, forming a Venn diagram.

You won’t just get better at navigating change—you’ll feel change within

Here’s how leadership coaching can support you:

  • Every leader brings their own values and skills to their role. Defining your unique leadership style forms the framework from which you can leverage your natural strengths and build new skills for growth. 

  • Between managing day-to-day demands and the long view of strategic goals, you’ve got a lot on your plate. Dedicated coaching connects you with the latest evidence-based leadership methods and tools, so that you can put them into practice right away.

  • You navigate a complex web of people, projects, and goals within your organization. Unlike internal resources that may be available, an objective, external coach offers you a neutral space to brainstorm, learn, and take action. 

  • Coaching offers you the space to explore strategies for building a collaborative work environment, without any preconceived notions about your team. We’ll think through individualizing your approach and adapting your style to the needs of the situation at hand.

  • Taking the time to thoughtfully reflect on challenges that arise means that you can show up as a more intentional leader. Rather than reacting in the moment, you can respond with empathy and understanding—and effectively influence and inspire others.

  • Because change is constant, resilience, adaptability, and an inner compass are essential as you navigate your career. When you embrace your role as the leader of your own career, you can shift from a sense that things are happening to you and instead intentionally and actively create your own opportunities.

Leaders at all levels can learn to put insight into practice.

  • A man with short black hair wearing a navy blazer, white shirt, and patterned tie, smiling in front of a white background.

    Cliff

    Insurance Team Leader

    "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."

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    Heather

    Business Developer & Leader

    “Working with Penney Leadership has made me stronger in a way that I could not have achieved on my own. 

    I was able to restructure my role at the company, enhance my compensation, and feel reenergized and excited for what comes next.”

  • Rakib

    Biotech Leader

    "There were a lot of Aha! moments that gave me different perspectives on my strengths and weaknesses, and I walked away with deeper insights about my leadership style.

    This process was transformational. Without a doubt It boosted my self confidence and added value to my personal brand."

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Individual Leadership Coaching

Develop your aligned leadership style to effectively lead yourself, influence others, and grow your career

Whether you hold an official leadership role or you lead informally, coaching offers you the time and space to understand who you are, define what you value, and envision what it means to you to lead authentically. 

Turning towards that inner work prepares and sustains you to create a team environment where people flourish, meaningful work takes root, and your own sense of satisfaction can thrive. 

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Your leadership coaching experience includes:

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    Discovery and mapping exercises to define your key goals, challenges, and opportunities

  • Icon of a light bulb with rays emanating from it, symbolizing ideas or innovation.

    Weekly, one-hour coaching sessions via phone or video for consistent and actionable support and accountability

  • Outline drawing of three stacked books on a black background.

    Access to Penney Leadership’s extensive library of curated tools to develop professional skills, self-knowledge, and confidence

  • Icon of an envelope with motion lines indicating sending or speed.

    Unlimited email support between sessions to keep the action moving forward, put new discoveries into practice, and celebrate your successes

  • Icon of a clipboard with checkmarks and a large checkmark in a circle, representing a completed checklist or task list.

    Hand-picked, current resources tailored to your specific questions

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    Invitation to join the Penney Leadership community of learning and practice (upon program completion) for continued support

Investment: $3,500

(split into 1, 2, or 4 no-fee installments)


Some employers sponsor some or all of the cost of coaching—I can walk you through how to ask!

I currently have very limited availability for individual leadership coaching clients. Please join my email list, The Strategic Leader’s Toolbox, for updates about openings.

Wherever you lead from, there’s support for you here. 

Any role, any industry, any identity.

  • “I left with a stronger sense of what I value, what I enjoy about my work and what makes me feel engaged and energized. I also gained new ways of thinking about leadership and skill sets, and clear ways to articulate what I bring to the table.

    Carole-Ann was instrumental in helping lay out a framework for my professional growth. I am more confident in how I approach the leadership track.”

    - Communications Specialist

  • “Working together helped me to become clear on my values and what I bring to the company as a leader.

    It has helped to build my confidence as a leader within the company and gave me great tools and resources to refer to as I continue to advance in my career here.”

    - Lab Manager

  • “This program gave me an opportunity to focus on career goals and define my leadership style for the first time.

    Having this opportunity has inspired me to be more thoughtful and intentional about career planning and how I want to show up as a leader.”

    - Crisis Communication Manager

Meet Your Leadership Coach

A smiling woman with shoulder-length light brown hair, wearing a pink blazer over a black top, standing in front of a white background.

Carole-Ann Penney, CPC

Founder & CEO | Leadership Strategist | Speaker | Coach

As a leadership strategist and coach, I’ve guided leaders like you for over 15 years to step into their authentic leadership and build their toolbox of mindsets, skills, and resources to make a meaningful impact.

After 15 years of doing this work, it’s never been more clear to me that leadership isn't something you “arrive at” when you finally get a senior title or accumulate enough experience. It shows up in how you advocate for yourself or your team, how you influence others, and how you decide to respond when the pressure is on. Even navigating your own career is a continual act of self-leadership. And cultivating your personal leadership approach takes the space, structure, and support to understand who you are, build real skills, and practice with intention. 

As your coach, I’m here to guide you on your unique leadership path. Instead of seeing leadership as something to be found, copied, or proved, let’s create a lived experience of leadership that’s meaningful, aligned to you, and effective for your team. 

I’m here for your questions. 

Here’s what you might like to know before working together.

  • Yes! I work with leaders who are called to make a positive impact that matters to them—and this can be true in any role, in any sector. 

    I’ve worked with leaders from industries including international service, museums and libraries, data science, arts and design, healthcare, manufacturing, education, social work, law, entertainment, finance, marketing, automotive, and so many more.

  • You don’t need to be in a formal leadership or management role to work together, and it’s okay if you haven’t really embraced your identity as a leader yet.

    We’re all leaders and have been practicing leadership throughout our whole lives. We can lead formally or informally at work, by managing people or influencing what’s happening around us, and we can also practice self-leadership by being intentional about our careers and choices. After our time together, you’ll walk away with a clearer sense of what leadership means to you and how you show up as a leader, whatever your role. 

  • Not everyone needs to aspire to manage a team! Navigating your career with intention—figuring out what you actually want, positioning yourself for where you want to go, making decisions that align with your values—counts as self-leadership.

    Coaching can be a great source of support when you’re working through a career decision, preparing for a pivot, trying to show up more strategically in your current role, and more.

  • Yes and yes! Many of my clients have successfully pitched a coaching engagement to their employer. It’s becoming more common for organizations to cover the cost of coaching for their leaders. 

    I have a “request for professional development support for coaching” template that outlines this program and its benefits that I’m happy to share with you. After our discovery call, we can shape that document together so that you’re prepared to make the request.

  • Your employer is making a smart decision to invest in you! 

    Occasionally, employers will ask to speak with me at the beginning of the process to learn more about how I work or to share their perspective, and I’m happy to connect. 

    However, I follow the guidance of the International Coaching Federation's Code of Ethics and everything we talk about in your sessions is completely confidential between you and your coach. An important benefit of working with a coach is that you have an external and objective resource you can be fully open with. I don’t share the content of our sessions with your employer—what you decide to share with them is completely up to you.

  • Absolutely! When you invest in leadership coaching on your own, it’s your choice what (if anything) you’d like to share with your employer about it. 

  • Not at all. Seeking out coaching doesn’t have to be in response to a particular issue, and it isn’t a sign of weakness—in fact, it’s the opposite. You can proactively seek out support to strengthen your skills, deepen your self-confidence, and improve your team’s performance. 

    I give you a dedicated space to feel heard and supported, to share what’s on your mind without being judged, and to gradually untangle the jumble of goals and priorities on your plate. Instead of telling you what to do, I offer fresh tools and perspectives you may not have considered before. As we work together, you’ll discover and practice new skills and mindsets that can serve you for a lifetime.

  • Just about anyone can call themselves a coach, but it’s important to me to bring the highest level of skill and service to our work together. I’m a Certified Professional Coach through the Institute for Professional Excellence in Coaching (iPEC), a program that’s accredited by the International Coaching Federation (ICF). I’ve been coaching for over 15 years and have helped thousands of clients get unstuck and find their paths.

  • Yes! I also provide coaching, training, and facilitation services for teams and organizations. I’m happy to discuss how any of these offerings can be customized to your company’s needs: 

    • Individual coaching for manager and team members

    • The Leadership Accelerator, my signature small group leadership development coaching program

    • Customized team strategy sessions

    • Tailored skill development workshops 

Apply for Leadership Coaching

Authentic leadership is strategic leadership. 

Developing your leadership navigation system unlocks your capacity for intentional, effective decision-making—now and into your future. 

If you’re ready to step into your role as a leader with more skill and confidence, I’m ready for you.

Leadership Coaching Application

Thank you for your interest in coaching! The Penney Leadership practice is full and individual coaching spots open infrequently. When spots do open, we’ll announce it via our newsletter, The Strategic Leader’s Toolbox.