Meet Natalie Glance, Duolingo’s Chief Engineering Officer, as she digs into the contradictions of modern leadership: How do you give employees the space to fail and learn while still hitting your team’s targets? Can you really build a diverse, empowering culture when you're sprinting on the startup treadmill?

In this conversation, she reveals what it felt like to be a math-loving girl and to encounter unsettling data at age 12. That experience still informs how she thinks about managing (and equipping others to manage) folks from underrepresented groups. 

She describes how she strives to scope roles thoughtfully and set folks up for success vs. “meddle” and explores why she now resists the temptation to over-invest in ensuring the success of a single team member, opting instead to attack problems at a “design level”. 

Joining the conversation is Natalie’s executive coach and founder + CEO of Talentism, Jeff Hunter. Together, with host Angie D’Sa, they expose Natalie’s journey with executive coaching and hard won lessons from the perspective of a woman in tech.

Talentism frameworks referenced in this episode: 

• Big4 (tool to learn about a person) 
• 4D (tool to understand levels of people management)

Meet Simmone Taitt, founder + CEO of Poppy Seed Health, who is rewriting the rules of pregnancy, loss and postpartum support. With 24/7 1:1 access to doulas, midwives, and nurses, Poppy Seed Health offers on-demand emotional and mental health support. 

Simmone opens up to Angie D'Sa, her executive coach, about how she transformed her personal trauma into profound purpose. And what it looked like to get out of her own way and build her team. 

Simmone shares a challenging part of her founder journey - one where she was slow to replace a star performer who left the company. And how limiting narratives got in the way of fast hiring and thoughtful onboarding.  When she faced those narratives head on, she evolved as a leader and her business experienced positive momentum.

If you've ever felt intimidated by putting together a team or been the new hire, this conversation is for you. Listen in and apply Simmone's hard won learning in your own life and work. To learn more about how Angie and other Talentism coaches guide their clients, check out Talentism.com

The Clarifier team wants to hear from you.

What are the challenges you are experiencing as a founder or manager right now? As the manager or the person being managed? Send an email or voice memo to [email protected] describing your challenge and we might just address it on the show.

Meet Joel Keating. He’s Grindr's SVP of Engineering & Chief Information Security Officer. He's joined by his Talentism coach, Gregory Kim.

Together, they describe how paying attention to Joel’s “This Sucks” response can open up the door to curiosity and unlock solutions to big problems at work. But, this only works if the curiosity is genuine. We learn that sometimes Joel can go through the motions: set up a meeting, ask questions, get feedback. But if under those behaviors Joel is actually harboring judgment, it doesn’t unlock anything. 

Greg and Joel have come up with a simple system to avoid the trap of hidden judgments. Joel exposes his expectations. All the time. This act is so simple, but when repeated regularly it has created powerful clarity for Joel and those around him. 

Everyday at Grindr, Joel applies the frameworks he learned through coaching. The problems at work don’t go away, but he is able to move through them with more agency and clarity, making the next challenge that much more manageable.

Listen in and apply Joel's hard won learnings to your work context. For more on the frameworks Joel references, visit Talentism.com

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 out
• How he methodically grapples with fear when it shows up at work
• How this deepens trust with his co-founder and they make better decisions as a result
• How his “super perception” drives faster feedback loops and better business outcomes

If you want to learn more about the framework Angie references in this episode, check out Purpose in the Big 4 model.

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.

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 expectations

• 16:27 Ope accepts that sharing her expectations and offering up frameworks and guiding principles are critical elements to managing well at Kibo

• 19:48 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

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.

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.