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I help creative + impact leaders take decisive action at pivotal moments

Faye Penn
Faye Penn Executive Coach

When you’re at a crossroads in your career or business, the right questions can move you forward. They can unlock new insights, remove barriers and challenge your thinking in the most productive ways. 


Before I studied executive and leadership coaching, I spent decades in New York City newsrooms, where your success rests on the questions you ask. Later, as a senior leader in NYC government advancing gender equity and innovation industries, I learned how the right questions can cut through complexity and lead to sound decisions.

I pursued coaching because I saw the power of inquiry to help people achieve more satisfaction and better performance in their work lives. My own practice is enhanced not only by my experience as a client, but also by my love for storytelling — helping clients craft messages that amplify their strengths and resonate with the market. While I work across industries, my core clients are creative and impact leaders, including elected officials. 

Major professional decisions are hard, and facing them without the right support is even harder. If you’re at a pivotal point in your business or career and seek coaching to help you chart your path, let’s talk.

The one thing you need your coach to do is ask the right questions

“Faye's coaching is truly exceptional. Her background in journalism gives her a unique ability to help her clients identify their passions and create structured plans to achieve them. With her disarming candor, she's not afraid to challenge her clients and help them overcome obstacles, all while providing unwavering support and accountability.”
— Non-profit communications agency lead
“My time with Faye is my favorite meeting every week — it's always so energizing. She has this amazing gift of reflecting back a deeply embedded core value that I didn't even know I had.”
— Executive Director of Women's Rights Legal Policy Organization
“Faye is different from other coaches because she really leverages her media background to zero in on messaging and branding. She has a strong bias for action and no BS.”
— Senior leader in risk management
“Our sessions are incredibly productive and really amp me up. Faye always pushes out the edges of my thinking on how I can profit from my expertise. She has motivated me to pursue a lifelong dream that I never took seriously until now.”
— Senior attorney in fintech
“Powerhouse, leader, superstar—I am not being hyperbolic when I say Faye is all these things. Her insightful questions have led to many ‘aha’ moments for me and given me a lot of clarity about my value and career path. She got me to think bigger about a creative project, so now, instead of just creating a product, I am building a brand.”
— Startup branding consultant
“Working with Faye has been invaluable as I navigate a career transition. She has helped me better articulate my success stories, strengths, and talents. Thanks to consistent goal tracking, accountability, and pointed questions from Faye, I have shifted from feeling unsure to regularly asking, "How do I win?”
— Multicultural marketing leader
“When leading a nonprofit in need of change, everything is moving so fast it's hard to know what to tackle first. As a new executive director, weekly sessions with Faye give me the time and space to face the hard questions and gain clarity about how to move forward.”
— Executive Director, arts non-profit




Whether you’re an emerging leader, an executive director or the head of your own company, you’re managing complex, ever-evolving demands. When it’s challenging to stay clear and focused, I can help you and your team anchor on what’s most important.


A lot goes into getting a business idea out of your head and into the market. When you’re ready, I can help you establish a launch plan and timeline, articulate your vision, identify a clear lane, craft a brand and design your business offerings while helping you stay focused and forward-moving.


If you feel like there's a more fulfilling way to use your professional talents, you may be right. When you're thinking about making a change, I will help you explore the possibilities, find clarity, chart a path forward and maintain momentum along the way.


Got a job interview, a high-stakes meeting, an urgent conflict to resolve or an important decision? I’m available for individual prep sessions to help you craft your talking points and attain the best outcomes. 


Magazine cover stories, public testimony, speeches, reports, press releases, web + marketing copy — I've written and edited it all. When you need just the right words to achieve your brand, business or career goals, I can help.


When you need a team-building event or offsite, I collaborate with professional development experts across industries to design lively group experiences that enhance teamwork, communication, accountability and other leadership skills.


​​First Executive Director of Women.NYC, serving New York women through salary negotiation training, business bootcamps, 1:1 career coaching and more. We also advocated for childcare as an economic development issue.

​Led innovation sector growth  for the New York City Economic Development Corporation, helping New Yorkers of all backgrounds future-proof their careers by tapping into growth industries.

Trained at Brown University’s ACT Leadership Program as well as the Center for Executive Coaching.

Faye Penn and Michelle Obama
Faye Penn and Michelle Obama
Faye Penn and Michelle Obama

Led a collaboration between First Lady Michelle Obama and seven top American fashion designers to create an original line of tote bags to benefit Let Girls Learn.

Faye Penn Guest Speaker
Faye Penn Guest Speaker

Founded Brokelyn, a buzzy local site (sold in 2016) about life on the cheap In Brooklyn. Drove revenue via a viral series of beer, wine and cocktail passports to hundreds of Brooklyn bars.

Currently serve as a board member for the Borscht Belt Museum, a new museum celebrating the Catskills resort era.

Faye Penn Leadership
Faye Penn Leadership

Have held senior positions across print, digital, video and e-commerce at New York Magazine, the New York Post, The New York Observer, A+E Networks and InStyle.

Wrote the Style & Error humor column for InStyle magazine, chronicling my misadventures in personal style.

Get in Touch

Please use this form to reach out with coaching questions, speaking opportunities, editorial work and other inquiries.

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