Imperfect Leaders

Jeffrey Cohn, Podcast Host
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Jun 21, 2025 • 1h 1min

How Can Good Lawyers Become Great Leaders? – with Anastasia Boyko

I recently wrote an article called, "How Yale Law School is Becoming the Next Harvard Business School."In this article, I showcased Anastasia Boyko, who was an Assistant Dean at Yale Law School (#1 law school in the country) build one of the most inspiring leadership programs in the country - "The Tsai Leadership Program."Joe Tsai (YLS, '90) and YLS Dean Heather Gerkin must have so much pride in what the school has accomplished in just a few short years.Today, more than ever, the world needs lawyers who know how to lead. We crave leaders with integrity, who clearly understand their core values, and know how to effectively communicate and inspire others.Anastasia is the perfect person to talk to about this topic.Share comments.
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Jun 9, 2025 • 57min

"I am in a Pacaso State of Mind" – with Founder & CEO, Austin Allison

Pacaso is more than a startup that allows individuals to buy a piece of a beautiful home...it's a state of mind. Being part of the Pacaso ecosystem helps people get off the day-to-day hamster wheel and focus on more important things in life, like relationships, discovery, and self-awareness.Bringing this vision to life requires a special kind of leader...one who balances strength and vulnerability...left brain analytics and right brain creativity...charisma and authenticity....confidence and humility.Today's guest - Austin Allison - Founder and CEO of Pacaso - is one of these very special leaders....what I like to call an ambidextrous CEO. In today's episode, find out why iconic leaders, like former Starbucks CEO Howard Schultz is a mentor to Austin and investor in Pacaso. And find out why you should be part of the Pacaso ecosystem as well – either as an investor or as an owner. To take creative liberty with Billy Joel's song ..."I'm in a Pacaso State of Mind."
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May 22, 2025 • 49min

How Can Emerging Leaders Develop a Breakthrough Mindset? – with Larry Connor – Philanthropist, Founder, & CEO of The Connor Group

How many great business leaders – in the entire world – can you name who have done any of the following: A) Helped pilot a rocket into space; B) Built a hot air balloon that could ascend 38,000 feet; C) Jumped off that hot air balloon at maximum height; D) Won highly competitive, off-road car races; or E) Explored the deepest depths of the ocean floor?Today's guest – Larry Connor – has done all of the above...not to mention his day job building one of the most successful real estate companies in the United States.  What's his secret?  A breakthrough mindset. He doesn't set artificial limits on what others think is possible. Instead, he asks a simple question, "why not?" More often than not, he succeeds. And when he fails, he learns from those setbacks and applies the wisdom to his next venture.
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Apr 27, 2025 • 1h 1min

Think Different. Can Autistic Children Develop into Innovative Leaders? - with Dr. Trenna Sutcliffe

"Think Different". That was the iconic tagline popularized by legendary Apple Founder, Steve Jobs. Autistic children have significant challenges – at work and at home. No doubt about it. But they also have a competitive advantage in the world of innovative leadership - they think different. Which begs the question – can autistic children develop into innovative leaders – in society and in business?To help us answer this question, we talk today with Dr. Trenna Sutcliffe. She created the world-renowned Sutcliffe Clinic, that is like a mini-Mayo Clinic, taking a holistic and multi-disciplinary approach to helping neurodiverse children reach their full potential and lead happier, more productive lives.Join – The Leadership Mindset Challenge
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Apr 2, 2025 • 41min

McDermott – The Ultimate Career Accelerator in Big Law, with Chairman, Ira Coleman

McDermott, Will & Emery is a leadership factory. They are career accelerators. This is their special sauce. It's what helps separate them from other elite, big law firms. It's why they are a talent magnet and have a unique, fun-loving, hard-working culture.Find out why firm Chair, Ira Coleman, still enjoys interviewing law students – and doesn't even get upset (in fact he gets excited) when candidates – who haven't even been hired yet – talk about their lives post-McDermott. Ira loves it when candidates ask, "what's my exit strategy?"
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Apr 6, 2024 • 1h 4min

Harvard College Dean Rakesh Khurana - How I Feel About Antisemitism, Racism, and Violence on Campus - and How We are Changing Our 387 Year Old Culture

Harvard is an iconic, 387 year old institution of higher education.  And it's time for a cultural overhaul. The events of the past year – racism, antisemitism, violence on campus, the removal of its president - have thrown their imperfections into stark relief for the world to see. Today’s guest - Harvard College Dean Rakesh Khurana – is very open and humble about Harvard’s imperfections. But that doesn’t mean he’s sitting still. Far from it. Recognizing he casts a long shadow and embracing a 'beginner's mindset', Khurana is spearheading the Intellectual Vitality effort which he hopes will revitalize the school’s culture. The lofty goal is to create a safe space environment across the entire campus and community – both physically and psychologically – that encourages tough conversations about divisive problems, in which students can learn from each other, regardless of how uncomfortable it is, at first. As Dean Khurana says, “let’s be hard on the problem, but easy on each other.” We should all be keeping an eye on Harvard's progress. Lessons gleaned may help other universities - and other divided institutions and partisan leaders across America in the media, politics, education, and business. www.imperfectleaders.com, Jefffrey Cohn
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Mar 18, 2024 • 26min

What makes 2024 SEC Champion - Coach Bruce Pearl so Special - Authenticity & Auburn University?

Coach Bruce Pearl teaches his players to be 'great receivers.' Find out in today’s podcast what this means and why it's so important.  Auburn Coach Pearl’s lessons of empathy and authenticity don't just apply in basketball – but in politics, business, and life.  Get ready for the Big Dance. www.imperfectleaders.com
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Mar 18, 2024 • 54min

What I Learned Running for President of the United States - U.S. Representative, Dean Phillips

U.S. Representative Dean Phillips is an innovative leader. He has drawn praise from modern day business heroes - like hedge fund icon Bill Ackman - for his willingness to shake things up - like staid industries including vodka, gelato, and most recently, U.S. politics. He even threw his hat in the ring and ran for President of the United States, even though everyone knew it was a long shot campaign. Find out what he learned during this intense process. www.imperfectleaders.com
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Feb 19, 2024 • 39min

Humanizing Private Equity - Ted Bililies, Global Head of Transformative Leadership at Alix Partners

On any given day, a casual investor can tune into CNBC and be in total awe.  Public companies are showcased and glamorized by messianic analysts in a concerted effort to push stock prices higher. But in reality, as I recently wrote, the future economy is increasingly being financed in private markets, far away from the glitz and glamor of the New York Stock Exchange. Today’s guest – Ted Bililies – is a world leading private equity expert. Long gone are the old, wild west days of KKR and Barbarians at the Gate, when private equity investors would buy a company, saddle it with massive debt, ruthlessly squeeze out costs, and sell the company for a quick buck. According to Ted, PE investors, in today's world, are taking a radically different approach to adding value – a fundamentally more human approach that offers a more enduring advantage, and one that is certain to appeal to a entirely new generation of talent.   www.imperfectleaders.com
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Nov 27, 2023 • 49min

Tim Connelly, Minnesota Timberwolves GM - The Emotionally Intelligent Leader

One of the best leaders in the NBA is today’s guest – Tim Connelly – General Manager of the Minnesota Timberwolves. Before billionaire owner Marc Lore and co-owner Alex Rodriguez lured him to Minnesota, Connelly worked side by side with Stan and Josh Kroenke and Coach Michael Malone - as the team's GM who helped the Denver Nuggets win their very first world championship. What is Tim’s secret sauce?  Is it superior analytics and competitive intelligence? Nope. Actually, it’s the exact opposite. Tim is an incredibly emotionally intelligent leader – comfortable in his own skin and able to forge authentic relationships with star talent like Anthony Edwards, Karl-Anthony Towns, and Rudy Gobert. Although Tim prefers to stay out of the spotlight – and rarely will you see him do public interviews on ESPN or the NBA on TNT– he was gracious enough to share wisdom with our listeners. We hope you enjoy! www.imperfectleaders.com

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