Leadership Coaching for Mission-Driven Professionals

Craft your Strategic Leadership Compass to lead effectively and in alignment with who you are.

Whether you’re new to leadership or have managed a team for years, you’re not alone if you feel like you have more questions than answers about leadership. 

Along your career path, it’s not unusual to…

  • Be tapped for a managerial role… without any leadership training or additional support

  • Get feedback about developing your “executive presence”... without any clarity on what that actually looks like

  • Pursue a promotion to reach a new level of leadership… but feel uncertain about how to articulate and leverage your experience

  • See leadership examples that you don’t quite want to emulate… but feel stuck when it comes to doing things differently

At a certain point in your career, leadership can feel like a skill that’s expected from you just like all of the job-specific expertise you bring to your work. For some people, this is exciting – you’re eager to manage and lead! For others, the thought of leadership can feel daunting – you’ve had training in so many of the skills you use day-to-day, but this big one wasn’t exactly covered in your last webinar. 

Either way, it makes sense to call in some additional support, and leadership-focused coaching can help set you up for success.

Leadership isn’t about fancy job titles, direct reports, and senior positions

Real leadership is about being prepared to navigate the unknown. 

A title change isn’t what makes you a leader (and a promotion definitely doesn't magically give you the skills or confidence you’re looking for). 

Leadership also isn’t a level you can achieve when you “finally know enough,” because that keeps you trapped in a chicken and egg situation. What comes first, the knowledge or the experience? And what does finally knowing enough even look like?

Instead, you can approach leadership as a practice, one that you’re able to authentically develop from wherever you are. 

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 with and for your team. 

And whether you’re seeking support to manage a team 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 supports your confidence, competence, and career path. 

Employees and employers see results from leadership coaching, which strengthens the impact of your work and your mission.

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

Build your Strategic Leadership Compass and thrive as a leader with purpose and resilience

Transform your leadership over just 10 weeks.

Developing your leadership ability starts with cultivating your navigation system—the compass that enables you to clearly, confidently, and strategically guide yourself and your team.

At Penney Leadership, we help you build your unique Strategic Leadership Compass, which is made up of the key elements of who you are, what you stand for, and what you bring to the table.

Over 10 weeks, you’ll get clear on your authentic leadership style, the core values that drive your work, the strengths that you and your team bring to the table, and your vision for the impact that you want to have. 

Defining your Strategic Leadership Compass allows you to operate from a strong foundation, no matter your role or the challenges ahead. Even in those moments when you feel unsure, you’ll be able to assess the situation, help others feel safe as you take a beat, draw upon your collective resources, and make intentional decisions about how to move forward.

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.

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

  • 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."

  • Heather

    Business Developer & Leader

    “I was able to restructure my role at the company, enhance my compensation, and feel reenergized and excited for what comes next. Asking for help can seem like a weakness, but working with Penney Leadership has made me stronger in a way that I could not have achieved on my own.”

  • Rakib

    Biotech Leader

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

  • Rebecca

    Director of Operations at a RI Tech Firm

    “Carole-Ann asked all the right questions and led me into thinking about my skills and what I bring to the table in a way I needed to hear. Her questions challenged me and helped me dig deeper and discover more about myself, which is EXACTLY what I needed. Now, I'm confident that I have the skills to manage this promotion and lead this team of people.”

  • Carin

    HR Manager, Automotive Industry

    "Having this individualized approach is like nothing I've ever had the opportunity to do! I went into this thinking I was literally just starting my leadership journey, but I realized that I'm actually already in the midst of it. I am a leader already. I learn more and more everyday that no one has this whole leadership thing figured out 100%. It is always changing, and I am definitely learning and bettering myself as I go! I didn't realize there were so many resources I could rely on."

Individual Leadership Coaching

Develop your aligned leadership style and become a leader people are inspired to follow.

Wherever you are in your leadership journey, 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.

 

Your leadership coaching experience includes:

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

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

  • Weekly customized leadership plans to apply your new insights at and in your work

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

  • Your clear and complete Strategic Leadership Compass—your guide to authentically and effectively navigating leadership challenges and opportunities

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

  • Hand-picked, current resources tailored to your specific questions

  • 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—we can walk you through how to ask!

We support a limited number of 1:1 leadership coaching clients each quarter, so if you’re interested in working together, don’t wait to reach out. 

 

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

Any role, any industry, any identity.

  • "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. I gained new ways of thinking about leadership and skill sets, and clear ways to articulate what I bring to the table."

    — 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 coaching 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

Discover Your Own Leadership

Meet Your Leadership Coach

Carole-Ann Penney, CPC

Strategic Career & Leadership Coach | Leadership Trainer

As a leadership trainer and coach, I’ve guided mission-driven leaders like you for over 10 years to step into their authentic leadership and build their toolbox of mindsets, skills, and resources to make a meaningful impact.

I also know firsthand what it’s like to muddle through leadership on your own. As a nonprofit leader, initially I felt like I had to model what leadership “should” look like—wearing a lot of blazers to work and copying the management style of my predecessors.  I felt like I was making things up as I went along (with much trial and error) and desperately trying to prove myself. It was an important time to try new things and see what fit, but I definitely didn’t feel like I was developing a sense of confidence in myself. 

Only after stepping back to define my personal mission, my values, and my vision for who I wanted to be as a leader did I see that intentional self-knowledge combined with practice was the key. With newfound confidence and a sense of groundedness, I could make strategic decisions about what would bring me closer to my vision and show up as the leader I intended to be. 

Now 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.

We’re here for your questions. 

Here’s what you might like to know before working with us.
Click a question to get the full scoop.

  • In short—yes! Being mission-driven is about doing work that’s meaningful to you. It’s about feeling called to make a positive impact that matters to you—and this can be true in any role, in any sector.

    We’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, and so many more.

  • Most clients don’t come to us already sure of themselves as leaders, and that’s okay! We’re taught to think of leaders as someone with a certain job title or set of responsibilities, but leadership is actually a practice, not a destination.

    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.

  • Your employer is making a smart decision to invest in you! Occasionally, employers will ask to speak with us at the beginning of the process to learn more about how we work or to share their perspective, and we’re happy to connect.

    However, we 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. We 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.

    We 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, your coach offers 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 us to bring the highest level of skill and service to our work together. Carole Ann is 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 each been coaching for over a decade and have helped hundreds of clients get unstuck and find their paths.

  • Yes! We also provide coaching, training, and facilitation services for teams and organizations. We’d be 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, our signature small group leadership development coaching program

    • Customized team strategy sessions

    • Tailored skill development workshops

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, we’re ready for you.

Leadership Coaching Application

In order to provide you with in-depth partnership & coaching support, I work with a limited number of clients at a time. At this time, coaching spots are full through the end of 2024. Please check back in early 2025 when I will reopen applications and subscribe to The Strategic Leader’s Toolbox to be the first to know about open spots!