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Meet Evan O'Donnell an early-stage investor + co-founder of the VC firm, Timespan.
Evan shares his powerful journey of overcoming the deep-seated fears instilled from growing up closeted as a gay man, striving for perfection to avoid the perceived catastrophe of being outed. Through self-work, Evan shed the limiting armor he had built up and transformed his heightened perception from a self-protective mechanism into a "superpower" for intuition, creativity, and problem-solving.
By continuously confronting his fears, he has found a way to unlock new possibilities for personal growth and professional success.
Host Angie D'sa, Talentism coach + partner, highlights how fear so often limits leaders' ability to learn and unleash their unique potential. In conversation with Evan, Angie learns:
How pursuing entrepreneurship felt scary -> "it's the purest form of self-actualization”How his armor still showed up at work, even after he came outHow he methodically grapples with fear when it shows up at workHow this deepens trust with his co-founder and they make better decisions as a resultHow his “super perception” drives faster feedback loops and better business outcomesIf you want to learn more about the framework Angie references in this episode, check out Purpose in the Big 4 model.
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Meet Meghan Joyce the founder + CEO of Duckbill, an AI-and-human powered answer to tiresome but deeply necessary life admin - think renewing your passport or making appointments with doctors who actually take your insurance.
But MJ wasn't always "Founder or Bust." In fact, she has spent most of her career working for pretty iconoclastic founders. First at the ride-sharing app Uber, then at the health insurance provider Oscar. In this episode, MJ vividly describes what it felt like to be baffled or upset by her boss’s behavior. And admits she now sees herself doing some of those same baffling things as founder and CEO! As Joni Mitchell might put it, she’s looked at life from both sides now.
Her executive coach of over 11 years, Libbie Thacker (coach + partner at Talentism), has been with her through all the ups and downs and joins us as well. Listen as MJ brings rare insight into how bosses and employees so often miss each other and what to do about it. -
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Meet Ope Bukola. She’s founder and CEO of Kibo School, an online university in Africa.
Ope is both relatable and remarkable. Relatable because, like so many founders, at one point she looked around her company and felt a pang of disappointment - everyone was falling short of her expectations. Remarkable because, instead of blaming her team, she did the uncomfortable thing and asked how she was contributing to that dynamic.
She realized she was giving her people lots of autonomy - the thing she most craved. But she was failing to give them what they needed. This included clarifying her expectations, driving alignment around a problem statement, and giving regular feedback.
In this episode, you also get to hear from Ope’s coach Mandisa Khanna! Mandisa helped untangle Ope’s frustration and helped her acknowledge a blindspot: because Ope thrived in ambiguity, she was blind to the structure that others on her team might need.
With Mandisa’s support, Ope experimented with new and sometimes unnatural behaviors. Eventually, Ope learned that managing her team more closely (the thing she silently dreaded) actually unlocked a way more entrepreneurial culture (the thing she wanted most). When people understood what she wanted, they were more creative, risk-taking, and agile.
If you’ve ever thought, “Do I have to fire everybody?” Ope shares an inspiring alternative.
Favorite moments of the episode:
5:04 Ope “hits a management wall”. She cancels 1:1s with direct reports when she sees the agendas (they were supposed to populate) are empty!11:04 Ope realizes that by not making her expectations explicit and known, she is making it virtually impossible for her direct reports to meet those expectations16:27 Ope accepts that sharing her expectations and offering up frameworks and guiding principles are critical elements to managing well at Kibo19:48 Mandisa shares how Ope's talent for structured thinking and strong goal orientation feeds into a "talent blindspot" (Ope underestimates how distinct and rare that talent / distinction truly is)27:16 Mandisa and Ope describe what it feels like to design & run experiments squarely inside your blindspot and how Ope applied her structured, methodical approach to this challenge. Angie references Mandisa’s article “Escaping the Feedback Loop” (4 min read)34:39 “What she was actually afraid of didn't come true.” Mandisa and Ope reflect that investing more into management, allowed for more autonomy and creativity from the team and cultivated a culture of learning that Ope deeply craved for Kibo.
To learn more about how Talentism works with leaders like Ope, visit www.talentism.com -
Meet Joshua Walsky. He was co-founder and CTO of Broadway Technology and came up during the dot com boom. Now he’s a Talentism coach, guiding the next generation of founders.
If you’ve worked in tech, you’ve probably met someone like Joshua. Exceedingly smart, exceedingly talented, and digging an exceedingly big hole for himself...
Like many technical leaders, his views on management have evolved dramatically since his early days as a software engineer. He used to believe that he was the one who should solve the problems so others could focus on execution. Through coaching, he came to understand the unseen cost of failing to create space for emerging engineers to get reps solving problems themselves. By unwittingly under-investing in developing his reports, he “borrowed against the future”.
Joshua devoted nearly 20 years to building Broadway’s offering and a team of 230+ people spanning five continents. He also helped raise $42M in strategic minority funding to accelerate growth and eventually negotiated the sale of Broadway.
In this episode, Joshua describes a painfully common pitfall in management - unknowingly limiting the development of your people - in a way we’d never heard before. Whether you are managing or the one being managed, we hope Joshua’s story unlocks learning for you too.
Note about this episode:
We love the ideas Joshua shares here. There are parts of this episode, however, where we don’t love the sound quality. In the spirit of not letting perfect be the enemy of good, we wanted to share this episode because Joshua’s words are so powerful.
Learn more about clarity coaching at www.talentism.com
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Meet Kathie Chao. She’s a Managing Director and Head of Digital Retail at Charles Schwab. Never one to back down from a challenge, her role has changed almost every year for the past decade.
In 2021, her scope shifted dramatically. She realized her anxiety about work was tipping into an unhealthy point. She started working with a coach and learned how to use those signals of anxiety to focus her attention on critical areas rather than overwhelm her, ensuring the anxiety and confusion she encountered was ultimately productive vs. limiting.
Kathie, a Harvard and Wharton Business School alum, is never going to stop attacking increasingly complex problems at work. She can’t stop, won’t stop. But if she wanted to get better at facing bigger, messier challenges, she realized she had to accept that along the way, she might not get an A+ at every turn.
In order to achieve her ambitious goals and thrive in senior roles, Kathie learned the most important relationship she could manage, is the one with herself.
Tune in to hear Kathie's journey, peppered with a ton of humor, pop culture references, and really practical ways she upped her game as a senior leader.
4:34 “It's hit an unhealthy point” Sifting through anxiety to understand herself and her context
6:07 “Are you driven by excitement or fear?” What the root of your momentum might tell you about how things will likely unfold.
9:55 Kathie uncovers a "status trigger" and how it shows up for her and others at work
18:29 Spoiler: Senior leaders are fallible, operating with their own fears and anxieties! Self-management is critical to scaling well.
27:09 Confusion as a learning tool: Kathie opens up a candid convo with a partner about a confusing remark he had made. Result? Deeper trust and a richer understanding of the risks and opportunities they were facing together
33:47 How Kathie prioritizes what confusion to dig into: “Does it get in the way of me accomplishing the goal?” If YES, must address.
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Meet Stef Sy, founder and CEO of Thinking Machines (TM). TM is a leading data consultancy, using AI to transform the way governments and conglomerates in South East Asia do business. Stef created TM because she wanted to put the power of data in all employees' hands, regardless of rank. And she wanted to make better jobs for emerging tech talent in her home-country, the Philippines.
In 2015, when Stef created TM, it had a rock band ethos – a motley crew making beautiful music, often chaotically, where each individual was unique and indispensable.
A few years later, this rock band vibe was getting in the way of TM's growth. To scale, TM needed to become an orchestra – a place where defined roles and processes enabled harmony. But Stef had always been more of a lead singer than a conductor. She faced a conundrum. No less than the future of her company - her mission and her life's work - was at stake.
In this episode, you’ll hear Stef share:
1:43 How she hired her early team back when Thinking Machines was relatively unknown: “It’s a miracle that these people said yes.”5:29 What it was like to uncover her own hidden motivations and compulsions – the deeply personal reasons she had started TM.15:24 Her moment of reckoning: “Either the company changes or I change.” 23:20 Accepting that her superpower might have become a liability and taking the scary leap of hiring people who would operate in new and different ways. 30:36 Learning to trust and empower the people she had hired – even when their actions ran counter to all her instincts. 40:00 Talentism’s 4D model for achieving scale: Do, Decide, Design, and Decode. For more on the 4D model check out this article (4 min read) -
BlackRock's Larry Fink sees pervasive fear and says we need hope. Talentism's Jeff Hunter says hope isn't enough - leaders need clarity.
Jeff provides tangible steps leaders can take to understand the root of fear, reorient with purpose, and turn unprecedented challenges into opportunities.
Gain a new leadership perspective.
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Meet Christina Sass, founding partner of Dive In Labs and co-founder of Andela. Tune in to learn:
How to productively analyze feedbackKey challenges faced by foundersWhy your context matters When to empower your team and let go
This episode has been updated since its original upload on 9/14/2023 to better reflect the standards of Talentism and was reuploaded on 9/22/2023. -
CEO coach Trevor Hunter unpacks his contrarian POV on goals. Tune in to learn…
How to set effective goals that winThe science and psychology of goalsThe problems with conventional thinking about goals -
Founder and CEO Jeff Hunter reveals why being a good manager is not about learning skills—it's about uncovering your fears.
Listen to learn:
The origin of today's thinking on management and why it’s wrongChallenges leaders face when managing their peopleKey practices for becoming a better managerEssential frameworks for developing effective management system -
"How do I take responsibility for a system that I, as a leader, have created?" Jeff Hunter tackles this question by sharing his reflections as a founder, CEO, hiring manager and executive coach.
Tune in to learn the three steps to ‘Start With Me’ and begin taking responsibility to your contribution to a suboptimal system.
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When the time comes for founders and CEOs to build their executive teams, it can feel challenging or even threatening. By not acknowledging their fear of letting go, these leaders either stay too distant or swoop in too quickly to grab the wheel. This results in founders and CEOs undermining themselves and their executives. Tune in to learn...
The struggles leaders face when letting go of responsibilitiesMethods for evaluating the talent needed at each stage of your organization’s growthStrategies for successful onboarding and management of new executivesThree essential frameworks for determining who should own what responsibilities within your organization -
Today employees’ expectations of their work experience and of their leaders are heightening. This creates inevitable, sometimes painful, confusion for leaders. Founder and CEO Jeff Hunter explores how the talent market is evolving, how we explore these great expectations, and how leaders can recognize their own confusion and adapt.
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The complexities of co-founder relationships are vast. Founder and CEO Jeff Hunter provides practical guidance for navigating these complexities and the inevitable challenges.
