May 21, 2024

We are thrilled to welcome Alisa Cohn as our guest today.

Alisa is a rock star in her field! She is a top executive coach known for her work with senior leaders in major organizations. She wrote From Start-up to Grown-Up, a book packed with practical tips for business growth and leadership development, and she has also done a TEDx talk.

Alisa exemplifies the caliber of top-tier executive coaches companies rely on to cultivate talent and effective leadership strategies. We truly appreciate having her here today to share her insights and experiences.

Stay tuned to learn from Alisa’s expertise in fostering talent and driving organizational success.

Alisa’s Career Transition

After beginning her career consulting at PricewaterhouseCoopers, Alisa had a pivotal moment when she realized she was following a career path prescribed for someone else instead of following her true passion. That realization led her to transition into coaching, a decision catalyzed by her experiences in the start-up world and executive roles during the dot-com boom and subsequent challenges in the early 2000s.

Building Brand and Gaining Endorsements

Alisa has invested significant effort in networking, coaching clients pro bono, teaching courses, and consistently delivering high-quality services. She had a transformative experience while teaching a money course at EMC that ultimately led to her coaching executives within the company and garnering valuable recommendations and endorsements. She highlights the importance of persistence, creativity, and experimentation in building a robust personal brand in any professional field.

Business Ownership and Team Structure

Alisa initially found it challenging to balance client acquisitions, project executions, and business growth. She highlights the significance of discipline, hard work, and strategic planning in overcoming those challenges and scaling her coaching practice beyond its initial stages.

Managing a Small Team and Collaborating with Coaches

Alisa emphasizes the importance of clear communication and shared goals when managing a small team or collaborating with coaches. She advises leaders to create trust and transparency within their teams by encouraging open dialogue and actively listening to all ideas. She also suggests leveraging the strengths and expertise of various coaches to foster a collaborative environment where team members can learn from one another and work synergistically towards common objectives.

Escaping the Hamster Wheel

Alisa advocates for strategic business development to escape the cycle of constantly seeking new projects and clients. She emphasizes the importance of proactive planning and creating systems that generate steady streams of opportunities rather than relying solely on reactive measures. She suggests leveraging networks, building long-term relationships, and cultivating a good reputation in the industry to attract ongoing business. By focusing on value creation, continuous improvement, and strategic partnerships, entrepreneurs can break free from the hamster wheel and grow their businesses sustainably.

Post-Pandemic Executive Challenges

Alisa highlights the importance of leaders being intentional about culture, leveraging technology for effective communication, and reinforcing core values to nurture a cohesive and engaged workforce. Alisa stresses the need for consistent recognition and feedback mechanisms to sustain a positive organizational culture amidst evolving work dynamics.

Handling Cultural Differences

Alisa encourages leaders to manage cultural differences within teams and organizations by promoting cultural awareness and inclusivity. She highlights the value of clear communication, empathy, and developing an inclusive environment where diverse perspectives are encouraged, actively sought out, and respected.

Strategies for Navigating Diverse Management Styles

Alisa champions adaptability and empathy as the key strategies for navigating diverse management styles, stressing the need for leaders to understand each team member’s strengths, communication style, and preferences. She encourages leaders to foster open dialogue, actively listen to team feedback, and create a culture of respect and inclusivity. By embracing diversity in management styles and leveraging the unique talents of each team member, leaders can cultivate a dynamic and high-performing team that can thrive in diverse environments.

Overcoming Impostor Syndrome

Impostor syndrome is a common challenge faced by professionals at various career stages. Alisa advises people to acknowledge and explore feelings of self-doubt with curiosity rather than judgment, emphasizing the importance of self-reflection and reframing negative thoughts. She also encourages individuals to create a highlight reel of their achievements and strengths as a tool for building confidence and resilience in the face of challenges and viewing setbacks as opportunities for their personal and professional growth.


Alisa Cohn is an Executive Coach who has worked with C-suite executives at prominent start-ups (such as Venmo, Etsy, Draft Kings, The Wirecutter, Mack Weldon, and Tory Burch) and Fortune 500 companies (including Dell, IBM, Microsoft, Google, Pfizer, Calvin Klein and Hitachi.) She is the author of From Start-up to Grown-up, which won the 2022 Independent Press Award, the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name, which provides insights and tools for the journey founders (and all leaders) must go through as they scale their leadership.

She was named the Top Startup Coach in the World at the Thinkers50/Marshall Goldsmith Global Coaches Awards and ranked globally as the #1 Global Guru for the past four years by the Global Gurus Research Organization. A sought-after speaker, Alisa was named one of the top 100 leadership speakers by Inc. She has keynoted events for IBM, PwC, Dell, and Citi. She is the executive coach for Runway, the incubator at Cornell’s New York City campus. She is a regular contributor to the Harvard Business Review, Forbes, and Inc. She’s been featured as an expert on BBC World News and in the New York Times and The Wall Street Journal. She is an angel investor and a Broadway investor.

Connect with Eric Rozenberg





Connect with Alisa Cohn

On her website

Download Alisa’s 5 Scripts for Delicate Conversations

Podcast: From Startup To Grown Up

Buy a copy of Alisa’s Book, From Start-Up to Grown-Up

About the author 

Eric Rozenberg

For two decades, Eric Rozenberg has consulted with Fortune 500 companies and produced conferences in more than 50 countries across diverse industries. His focus is creating meetings that are not only breathtakingly memorable but which bring corporate strategies to life and amplify team motivation/performance.

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