Key Moments
Alisa Cohn - Prenups for Startup Founders, Reinventing Your Career, and More | The Tim Ferriss Show
Tim FerrissKey Moments
Alisa Cohn on self-awareness, leadership, and critical conversations for career and startup success.
Key Insights
Self-talk and self-compassion are crucial for personal and professional growth, as negative self-talk hinders performance and creativity.
Effective feedback, including both positive and constructive, is vital for employee development and building strong team relationships.
The 360-degree feedback process, while challenging, provides invaluable insights into leadership blind spots and areas for improvement.
Pre-mortems are a powerful tool for anticipating potential project failures and proactively planning to avoid them.
Meaningful meetings require clear goals and defined success metrics to avoid wasting time and demotivating staff.
Co-founder 'prenups' are essential for addressing potential disagreements and aligning on long-term vision, even for successful ventures.
THE UNEXPECTED PATH TO COACHING
Alisa Cohn's career journey began far from coaching, starting in journalism and moving into non-profit and strategy consulting. Her time at PwC as a fast-track partner candidate ended dramatically after a health crisis revealed a deep dissatisfaction, prompting her to search for work that offered a sense of purpose and the ability "to make a difference." This led her to discover coaching, initially through exposure to a dynamic speaker at a 'body and soul' conference, which resonated with her natural inclination to support and problem-solve.
EMBRACING THE UNKNOWN: FROM STARTUP CFO TO COACH
Despite a desire to pursue coaching, Cohn felt she lacked sufficient leadership experience. She took a detour into the startup world, initially as an early employee at Corporate Alumni (a LinkedIn precursor) and later as a reluctant CFO and then GM of a science startup. These experiences, though unplanned, provided invaluable leadership insights and practical business acumen. When the dot-com bubble burst, she seized the opportunity to transition fully into coaching, leveraging years of training and informal practice with friends and strangers to build her new career.
THE MARSHALL GOLDSMITH PILGRIMAGE AND 360-DEGREE FEEDBACK
Cohn's ambition led her to cold email renowned coach Marshall Goldsmith, securing a meeting that evolved into a professional collaboration. This connection introduced her to the powerful concept of 360-degree feedback, a process she later facilitated for Tim Ferriss and numerous CEOs. This method gathers anonymous feedback from colleagues, identifying strengths, development areas, and behavioral suggestions. While often confronting, especially when revealing blind spots or perceived failures, the process is invaluable for fostering self-awareness and providing a roadmap for leadership improvement.
UNDERSTANDING AND IMPLEMENTING 360-DEGREE FEEDBACK
The value of 360-degree feedback lies in its ability to highlight behavioral patterns and areas where an individual's self-perception diverges from how they are seen by others. Cohn emphasizes the importance of not just receiving the feedback, but also internalizing it, identifying actionable themes, and communicating a plan to stakeholders. This transparent approach, including apologies where appropriate, helps to heal relationships and foster open dialogue, moving beyond defensiveness to genuine growth and improved team cohesion. Tim Ferriss's personal experience underscores the emotional challenge and ultimate utility of this comprehensive feedback.
THE POWER OF PRE-MORTEMS AND PRODUCTIVE MEETINGS
Beyond post-mortems, Cohn advocates for 'pre-mortems,' a strategic exercise where a team assumes a project has failed and identifies all the factors that could have contributed to that failure. This proactive approach allows for early identification of risks and the implementation of preventative measures, as demonstrated by a client who averted communication breakdowns in a large partnership. Similarly, Cohn stresses the importance of running productive meetings by establishing clear goals, defining success metrics, and ensuring all participants understand the desired outcome, thereby preventing wasted time and staff demotivation.
CULTIVATING SELF-AWARENESS, COMPASSION, AND TALK
Cohn highlights three crucial aspects of personal development: self-awareness, self-compassion, and self-talk. Recognizing and transforming negative self-talk is paramount, as it saps energy and hinders effective problem-solving. Leaders, in particular, benefit from self-compassion, which prevents harsh internal criticism from seeping into team interactions and fostering an unhealthy work environment. By adopting a mindset of "I will be okay no matter what," individuals can approach challenges with greater agency and resilience, detaching their well-being from external circumstances.
SCRIPTS FOR DELICATE CONVERSATIONS: FROM POSITIVE FEEDBACK TO FIRING
Cohn provides comprehensive scripts for navigating various delicate workplace situations, recognizing that many struggle with the exact words to use. She starts with positive feedback, emphasizing its importance for motivation, confidence, and building goodwill. This progresses to developmental feedback, which helps employees build on strengths, and then to difficult feedback for persistent issues. Her five-step firing sequence includes preparatory conversations and a clear, humane script for termination, ensuring employees are not surprised and leaders have exhausted all avenues for improvement.
FOSTERING CAREER GROWTH THROUGH EFFECTIVE ONE-ON-ONES
One-on-one meetings are presented as a foundational tool for building strong manager-employee relationships and fostering career development. Cohn offers scripts for setting and resetting expectations, encouraging employees to prepare discussion topics beyond mere status updates. Key questions focus on employee satisfaction, career aspirations, company vision, and peer relationships. Crucially, managers are encouraged to coach rather than simply solve problems, empowering employees to take ownership of their growth. Proactive career coaching sessions further solidify the manager's supportive role.
MANAGING ORGANIZATIONAL CHANGE: LAYERING AND NETWORKING
Cohn tackles the sensitive issue of "layering" – bringing in more seasoned leaders above existing employees, a common challenge in growing startups. Her script emphasizes transparency, acknowledging the incumbent's contributions while clearly explaining the business need for specialized executive experience. This direct yet compassionate approach aims to manage employee reactions and reinforce the overall company strategy. The episode concludes with practical networking scripts, advocating for consistent relationship building ('dig your well before you're thirsty') and providing templates for reconnecting or making specific requests.
FROM STARTUP TO GROWN-UP: A GUIDE FOR LEADERSHIP JOURNEYS
Cohn's book, "From Startup to Grown-Up: Grow Your Leadership While Growing Your Business," is structured to address key leadership challenges founders face. It's divided into three sections: "Managing You" (self-awareness, managing personal journey), "Managing Them" (hiring, onboarding, firing, delegation), and "Managing the Business" (board relationships, co-founder dynamics). The book aims to inspire self-reflection, prevent avoidable mistakes, and provide tangible tools for leaders, underscoring that leadership is an acquired skill, not an innate talent. The creation of the book itself was a personal journey, overcome by confronting her own 'immunity to change' and resistance.
THE CRITICAL CO-FOUNDER CONVERSATIONS
A significant focus in Cohn's book and coaching is on co-founder relationships, often likened to a marriage, with her advocating for 'prenup' discussions. These involve critical questions, such as what to do if a co-founder isn't scaling, how to resolve massive disagreements, and aligning on the ultimate vision and exit strategy for the company. Neglecting these conversations, driven by initial excitement, can lead to significant problems down the line, even for successful ventures. Establishing a shared understanding of company culture and individual financial aspirations is also paramount.
Mentioned in This Episode
●Products
●Software & Apps
●Companies
●Organizations
●Books
●Concepts
●People Referenced
Startup Leadership & Communication Cheat Sheet
Practical takeaways from this episode
Do This
Avoid This
Common Questions
Alisa Cohn started in traditional corporate roles, including CPA and strategy consulting, but a moment of burnout led her to re-evaluate her career. She sought out a coach, which inspired her to pursue coaching as a profession. She gained experience through startups and formal coach training before fully transitioning.
Topics
Mentioned in this video
A Japanese multinational conglomerate corporation, mentioned as one of the enterprises whose CEOs and C-suite executives Alisa Cohn has coached.
A private research university in Boston, where Alisa Cohn worked as chief of staff to the provost.
An American business magazine, where Alisa Cohn's articles have appeared.
An American fashion house, mentioned as one of the enterprises whose CEOs and C-suite executives Alisa Cohn has coached.
An Ivy League university, where Alisa Cohn attended business school, focusing on finance, accounting, and strategy.
An American daily newspaper, where Alisa Cohn has been featured as an expert.
A product review website, mentioned as one of the companies whose founders and executives Alisa Cohn has advised.
A general management magazine, where Alisa Cohn's articles have appeared.
An American business magazine focused on small businesses and startups, where Alisa Cohn's articles have appeared.
A private research university in Boston, where Alisa Cohn completed her undergraduate studies as a journalism major.
A Houston-based hedge fund specializing in trading energy products, founded by John Arnold.
A new company launched by Helix Sleep, making premium customizable sofas and chairs that ship directly to your door at a fraction of traditional costs. Products are spill, stain, and scratch resistant.
An American fashion company, mentioned as one of the companies whose founders and executives Alisa Cohn has advised.
A strategy consulting firm where Alisa Cohn had a stint before business school.
A mattress company mentioned as the parent company of Allform, whose mattresses Tim Ferriss has been using since 2017.
A multinational computer technology company, mentioned as one of the enterprises whose CEOs and C-suite executives Alisa Cohn has coached.
An American newspaper publisher, mentioned as one of the enterprises whose CEOs and C-suite executives Alisa Cohn has coached.
A financial software, data, and media company, mentioned as one of the enterprises whose CEOs and C-suite executives Alisa Cohn has coached.
A company offering premium bone broth made with 100% grass-fed and grass-finished cows and organic free-range chickens. Their broths support gut health, immune system, weight loss, and fasting regimens.
An e-commerce company focused on handmade or vintage items and craft supplies, mentioned as one of the companies whose founders and executives Alisa Cohn has advised.
A Big Four accounting firm where Alisa Cohn worked after business school, though she ultimately felt it wasn't the right fit for her.
A business and employment-oriented social media platform, mentioned as a more successful iteration of Alisa Cohn's first startup, Corporate Alumni.
An automated investing platform (robo-advisor) that helps clients diversify portfolios, minimize fees, and lower taxes, overseeing $20 billion in assets.
A daily fantasy sports and sports betting company, mentioned as one of the companies whose founders and executives Alisa Cohn has advised.
A leading global investment banking, securities, and investment management firm, which Alisa Cohn considered for a role in private client services before deciding on a startup.
A prototyping and collaboration platform for design, mentioned as one of the companies whose founders and executives Alisa Cohn has advised.
An American multinational technology company, mentioned as one of the enterprises whose CEOs and C-suite executives Alisa Cohn has coached.
Alisa Cohn's first startup, described as an early precursor to LinkedIn.
A men's basics brand, mentioned as one of the companies whose founders and executives Alisa Cohn has advised.
A Japanese multinational conglomerate, mentioned as one of the enterprises whose CEOs and C-suite executives Alisa Cohn has coached.
An American multinational technology corporation, mentioned as one of the enterprises whose CEOs and C-suite executives Alisa Cohn has coached.
A multinational technology and consulting company, mentioned as an example of a large company with a different set of problems compared to a startup.
A book by Kim Scott, recommended for its insights on giving feedback, emphasizing building strong relationships before delivering it.
A book by Karen Pryor, recommended for its insights into effective training methods and the ineffectiveness of overwhelming negative feedback.
A companion book to 'Crucial Conversations,' also recommended for addressing difficult conversations.
Alisa Cohn's book, described as a guidebook for entrepreneurs on the leadership journey from founder to CEO, containing scripts for delicate situations.
A men's magazine, for which AJ Jacobs wrote an article titled 'I Think You're Fat' about radical honesty.
A book by John Breglio, recommended as a helpful resource for understanding the economics and ecosystem of Broadway.
A recommended resource for improving difficult conversations, which gives tools to address challenging discussions.
A book by Jim Loehr, which contained an inventory exercise for self-assessment that greatly impacted Tim Ferriss in high school.
A book by Harvey Mackay that inspired Alisa Cohn long ago about the power of building and nourishing a network proactively.
A book by Tim Ferriss, in which John Arnold's insights on time and money were featured.
A book by Robert Kegan, whose process helps individuals identify and overcome internal obstacles to desired change by exploring 'what's on the brake.'
A book by Richard Koch and Greg Lockwood that reinforces the importance of building and nourishing a strong network.
Author of 'Don't Shoot the Dog!', a book about the effectiveness of positive reinforcement in training.
A well-known executive coach, referred to as the 'number one coach in the world,' whom Alisa Cohn sought out and later worked with on coaching engagements.
A behavioral scientist and author, mentioned as someone who took an interest in Marshall Goldsmith early in his career.
A friend of Tim Ferriss and doctor, who interviewed John Arnold on his podcast.
A dynamic coach who inspired Alisa Cohn to pursue coaching after an encounter at the Body and Soul conference.
Co-author of 'Superconnect,' a book about the power of networking.
Author of 'Mental Toughness Training for Sports' and expert who has worked with top-level athletes. His book's inventory exercise helped Tim Ferriss with self-assessment.
Co-author of 'Superconnect,' a book about the power of networking.
A fan-favorite podcast guest and ketogenesis expert who originally recommended Kettle & Fire bone broth.
The guest on the podcast, an entrepreneur coach for nearly 20 years, author of 'From Startup to Grown-Up,' angel investor, and advisory board member.
An incredible investor and effective philanthropist, youngest US billionaire in 2007, who shared insights on time as money and the opportunity cost of unproductive meetings.
A friend of Tim Ferriss and author known for undertaking absurd yet profound experiments, who wrote an article for Esquire on radical honesty.
A coach who provided Tim Ferriss with the reframe of life's challenges as 'pop quizzes from the universe.'
Co-founder of Airbnb, who reportedly cried in his car after receiving 360-degree feedback.
Author of 'Radical Candor,' a book about delivering effective feedback by building solid relationships.
An astrophysicist whose quote about life being the obstacles, not the path, is shared as a helpful reframe.
A fellow coach and one of Marshall Goldsmith's '100 Coaches' who guided Alisa Cohn through the 'Immunity to Change' process, helping her overcome writing blocks.
Author of 'Immunity to Change,' whose process helped Alisa Cohn overcome internal resistance to writing her book.
Author of 'Dig Your Well Before You're Thirsty,' which advocates for proactive networking.
Author of 'I Want to Be a Producer: How to Make a Killing on Broadway... or Get Killed,' a book about the Broadway industry.
The capital and most populous city of Massachusetts, where Alisa Cohn attended Boston University and worked early in her career.
A small town in Massachusetts where Alisa Cohn grew up.
A town in Massachusetts, neighboring Holliston, known as the starting point of the Boston Marathon.
A coastal town in San Diego County, where Marshall Goldsmith resides and where Alisa Cohn met him for the first time.
More from Tim Ferriss
View all 566 summaries
76 minHow to Quiet the Ruminative Mind and Avoid The Traps of Self-Help — Tim Ferriss
86 minNYT Bestselling Author on Writing 200+ Children's Books — Tish Rabe
134 minChampion of "Alone" on The Art of Survival — Jordan Jonas
105 minTim McGraw — Selling 100M+ Records and 30+ Years of Creative Longevity
Found this useful? Build your knowledge library
Get AI-powered summaries of any YouTube video, podcast, or article in seconds. Save them to your personal pods and access them anytime.
Try Summify free