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Portrait of Courtney Kaplan
COURTNEY KAPLAN  •  Founder and Coach

Generate Powerful Results

As Founder of Iconic Leadership Coaching, I help executives generate powerful results and create impactful careers based on their values. Working with designers for over 20 years in the technology industry, I provide practical guidance using the tools and techniques to empower clients to recognize and develop their innate leadership style.

I show my clients how to better navigate the work landscape by leveraging their strengths and developing the skills they’ll need to lead with clarity and confidence. Whether you are a seasoned executive, stepping into a leadership role or searching for a professional path in which you feel passionate, my practical and supportive approach will propel you on a clear trajectory of growth and opportunities that fit you perfectly. Together we’ll unlock your leadership potential and transform your life.

Deep Questions and New Practices

We live in stories. The stories about ourselves, our lives and our world create or limit our possibilities. As a leadership development coach, I help you get curious and ask deep questions that unpack how you frame your world and your approach to leadership. I guide you to explore new possibilities that build on your natural skills. Together we will establish new practices that move you closer to your goals.

In the professional realm, we often think, analyze and operate from the neck up, ignoring the wisdom and guidance our bodies and emotions provide. I teach you how to use all of the rich information available to you. By harnessing body wisdom, identifying feelings and understanding emotions in your work landscape, you can open more possibilities for a satisfying future. (And have fun while doing it!)

Client-Focused Transformation

In a world of constant change, we are continuously faced with the need to successfully adapt to new circumstances. My coaching process is transformational, not transactional. That means we’re not fixing small tactical things. We’re looking at a larger point of view -- the big picture of how we frame our life and our work. And when one area moves, the whole picture quickly improves.

I connect the dots that aren't obvious and can make sense of things that seem chaotic or unrelated. I am good at observing and catching small details and am able to listen deeply and pick out things my clients are assuming or taking for granted. I often hear “I never thought about that before” and “That’s a great question”. 

Iconic Leadership Coaching creates the space for us to have a meaningful conversation that will shine a light on new approaches that will generate fresh results. Every coaching session will begin with your most pressing issue. We’ll address the situation through rigorous questioning and conversation to establish a wider more creative perspective and more possibilities. We'll then establish a practice to ensure you can apply your new learning immediately.

Access your curiosity, creativity and commitment in four steps.
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Uncover what you want to create at work and at home. Discuss where you’d like to go and what success looks like for you.

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Unpack old stories. Debunk outworn beliefs. Design a new approach leveraging your strengths and support.

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Establish practical applications you can benefit from immediately.

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Build on your practice. Develop mastery of leadership skills and shine.


Cultivating leadership and strong management skills with the support of a dedicated coach can be deeply transformative—for both you and your team. My coaching approach introduces you to new ways of showing up with authentic confidence. You will be encouraged to identify patterns, to access your emotional intelligence and to solve complex problems by asking and answering big questions.

My sessions will help you

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leadership and management skills

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your communication using all of your resources

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a clear vision and set goals to bring
your vision to life

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stronger relationships for more
effective team dynamics

Who I Work With

If you find yourself saying, "What used to work in the past isn’t working anymore" or "I don't know how to get from here to there," I can help you see new possibilities and actionable steps forward. 

Most of my clients are high performers who are looking to chart a clear trajectory of growth and unlimited opportunities. My clients are the feelers, believers and makers who possess certain gifts that require vulnerability and risk in order to create new ideas and concepts. They think differently. I work with clients to unlock the superpowers inherent with ADD/Dyslexia and other neurodivergencies that are so common in creative fields.

My clients have the experience and don’t need confirmation that they are spending time in the right areas, but they generally DO need to build better ways to connect, collaborate and create alliances to produce the results expected of them. 

If this sounds like you and you are looking for support and encouragement from someone who understands, let’s talk.

Courtney Kaplan Portrait


I've been honored to help unlock leadership potential for executives at

Apple LogoGrab logoMailchimp logoLyft logoShopify logoPinterest logoMotorola logo

In Need of Authentic Guidance

My clients desire to be more expressed and authentic in all aspects of their lives. They are seeking a way to develop different skill sets as they move their careers forward into leadership positions. 

Most of my clients come to me with a professional concern, but often the issues they face are impacting their personal lives too. Our work lives and home lives are intertwined more than ever, so the coaching we do for your professional life will change all aspects of your world. Together we'll undertake discovery conversations, design better outcomes and put our findings into practice to build your leadership and improve your life.

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I Can Help You

  • Show up to demanding leadership challenges with confidence and ease
  • Resolve imposter syndrome
  • Improve interview skills to build your team or find a better job
  • Develop strong relationships at work, even with difficult people
  • Understand blindspots that are holding you back from advancing
  • Build stronger, more effective teams by hiring and retaining great talent
  • Become a clear, effective communicator
Let's work together
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How it Works

I help clients better navigate the work landscape, leverage strengths, nurture authentic presence and develop the skills needed to lead with clarity and confidence. Together we work on strategies to build strong and effective teams and retain high-potential employees. We’ll uncover new opportunities by identifying old patterns and asking the questions that will encourage you to connect to what you truly want both personally and professionally. I provide practical, authentic guidance using the tools and techniques of conscious communication, mindfulness and empowerment to help clients recognize and develop their innate leadership style.

Through a series of 1:1 meetings (on Zoom), we dive into thought-provoking conversations that reveal new ways of understanding how you’ll achieve what you really want. Sessions end with a new practice or practical homework to apply what we've uncovered back into your everyday life.

Design-minded leaders are impassioned individuals who are always looking to solve big problems in inspiring and beautiful ways. Are you ready to discover YOUR brilliance?

Why It Works

Coaching works because you create the space and time to analyze some of the automatic ways you're living and working. When you have an experienced partner to shine the light, open the conversation and bring a wealth of wisdom and life experience, you can go beyond the discussion of what is not working and take active steps to change. Coaching requires commitment. You're committed to PRACTICING new ways of being until they become your new normal. I facilitate the process so you can dive into the possibility with curiosity and dedication.

You Will Experience

  • Stronger self-awareness and confidence
  • Improved communication and relationships
  • Enhanced creativity, ideas and solutions
  • Opportunities for greater impact
  • Skill-building to help teams excel and retain talent
  • A sense of belonging, satisfaction and ease

Step Into Bigger Opportunities

See Yourself
(and the world)

Iconic Leadership Coaching will equip you with new ways of seeing the world. You will become a better observer of yourself and others which will allow you to be a more generative leader. When you have a deeper understanding of who you are and what you're capable of, you can start to make commitments that move toward new possibilities. My clients experience more peace, more confidence, more ease and more potential in their lives. We will turn your beliefs upside down, so that problems will turn into possibilities.

My clients experience more peace, more confidence, more ease and more potential in their lives.
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What You
Can Expect

This is a dynamic coaching process; one that is approached with compassion, lightheartedness and a sense of humor. Working with me, you will be met with my full presence. I listen intently to every word and pick up on subtle body language so that I can ask you the big questions to help you see things differently. We will define your strengths, improve your communication skills and clarify goals that fit you best as you step into more authentic leadership. I will help you clarify your priorities, strengthen your time management, build strong teams and support networks. I will help you build the next generation of leadership and navigate the boundaries of delegation. We are working towards transformation for you as a leader.

I use the following techniques (and associated inquiries) to bring my clients to a deeper understanding of their professional path:


Who can support you to get through what you might not know? Where can we find help?


Examine old beliefs and create new perspectives that will move you forward.

Missing Conversations

Where are the breakdowns and what conversations are missing?

Making Speech

Using speech acts to open a new future and move forward productively. We make a declaration, an offer or a request.


How do we break ineffective patterns of communication?


What do you know that you don’t realize
you know?

When we are only transactional (as many workplaces can be), we don’t know how to have conversations that open new possibilities to take care about what we care about most.

These conversations will open new futures.


Interested to hear what my clients have to say about working with me?

"I was working 10 hours a day and knew I wanted a change but I was too overwhelmed to begin the process. Weekends and evenings were my time to zone out. By working with Courtney, I became unstuck by seeing I could make the time commitment to meet with her. From those meetings, I was able to take new steps, reconnect with my networks and explore new ideas.” - Heather H.

“I have always hated change and Courtney was extremely helpful in helping to ease my nerves. During COVID, we spoke a lot about making changes to adapt to the "new norm". In one session, we practiced a body scan to help ease some of my anxiety. From there, we kept building new habits to check in with my anxiety. Courtney helped to change my perspective on owning the things I can control and letting go of the things I can’t.”

“Being a part of the inaugural Finding Joy workshop was such a special experience. It felt like a true act of resistance to choose joy despite all we have been dealt this year. I found this workshop to be just the right balance of opening my eyes while also being tangible, actionable and accessible. I immediately started leveraging these new tools which transformed multiple relationships in my life. One of the most meaningful takeaways for me was that finding joy is not just about seeking out joyous experiences, but also in addressing the things that can leak joy or make joy feel inaccessible.”

“During a period of tremendous transformation in most areas of my life, I was guided to Courtney’s coaching. I had lingering blindspots that were preventing me from making the final push to step into a new career. Working with her has been such a gift. Her warm, grounded energy and clear guidance is a force. With her support and direction, I moved through some pretty intense emotions that ultimately empowered me to make the plunge into purpose-fueled work.”

“My coaching conversations with Courtney are calming and comforting, while also helping me claim and cultivate the career and lifestyle I want. Courtney welcomes my ideas and gives me strategies to uncover hurdles. She shows me the patterns in my life that are supporting my creativity and those that are causing conflict. I’ve learned that coaching is not remedial, it’s necessary. It’s the edge and nudge that keeps me committed to the life I want to live.”

“I moved to the Bay Area right before the Pandemic and have been looking for my next role here. Working with Courtney gave me the edge that I was missing. It was hard connecting with people during such a strange time and also to connect in a way that went beyond the surface. Courtney has been such an amazing guide through this whole journey. She has helped me to showcase the best version of me so I can find the perfect role for my new life.”

“Working with Courtney helped me identify my strengths and forced me to think about where I excel. My interview prep with her helped refine and sculpt ideas about who I am. We built cohesive stories about the experience I have. Today, I have a better understanding of my big picture. I have clarity about my career and what I want it to look like.”

“Courtney leads her Finding Joy workshop with warmth, creativity, and humor. I found an opportunity to connect, learn and challenge myself in an intimate and supportive group that works to break patterns and make new discoveries.”

“My coaching relationship with Courtney had such a great impact in my recent career journey. Having her on my side and as a sounding board really helped clarify and untangle what is often not obvious in transition and development as a design leader. I appreciate how Courtney points out her observations with clarity. We explored them together, at my pace, which resulted in actionable insights that were authentic.”

“I love her gentle guidance that is based on wisdom, intuitiveness and a wealth of experience. It's because of Courtney’s support that I am where I am.”

“I think of our coaching sessions just about everyday. They were incredibly helpful in moving through mental obstacles in my personal life and professional life. In my professional life, the obstacles are still there. I just navigate them differently.”


Throughout my life, the consistent thread has been an eagerness to explore problems and find beautiful solutions. 
Understanding how to ask questions, listen carefully, think broadly, gather wisdom from clients and creative partners frequently resulted in beautiful solutions to real problems. As a Development Coach and Founder of Iconic Leadership Coaching, I guide my clients to help them realize their full leadership potential by asking big questions. I help designers and creative executives grow, build effective teams that generate results and create a satisfying professional path that helps them realize their full potential.

Prior to coaching, I worked in the design field for over 25 years, first as a designer, then as Principal at Hot Studio, a consulting firm in San Francisco. Most recently, I founded and led the first Design Operations discipline at Facebook, where I developed a global team of Design Program Managers (DPMs) from the ground up. I have studied with the Institute of Generative Leadership, Strozzi Institute and Newfield Network Certified Coach Training. These programs have helped me see the interconnection between our professional and personal lives. 

I experienced many career changes and challenging work environments which have required reinvention and pivots. These experiences revealed that the more I changed myself on the inside, the more my outside conditions changed, too. This was a radical transformative breakthrough; one that greatly informed the coaching work I do today. We don’t need to wait for something outside ourselves to change in order to live the life we want. We can be the change. 

Having a coach to partner with you provides an advantage in a complex and demanding world. Learning to listen to your life and recreate your story can be a failsafe guide. 

Let’s take a look together.

I'm ready to realize my own brilliance
Courtney Kaplan