Podcast
Speak Your Mind Unapologetically Podcast
Hosted by For People Leaders Leading Bold Conversations | Ivna Curi · EN
Speak Your Mind Unapologetically is the leadership communication podcast for people leaders — managers, directors, and VPs — who want to speak up, lead bold conversations, and influence outcomes that matter.
Whether you're addressing conflict, delivering feedback, leading meetings, or navigating difficult conversations, this podcast gives you practical strategies to:
👉🏼 Communicate with clarity, confidence, and conviction=
👉🏼 Influence decisions and build trust across functions
👉🏼 Speak up under pressure — without sounding aggressive or backing down
👉🏼 Encourage your team to share ideas, concerns, and feedback
👉🏼 Tackle conflict, disagreement, and misalignment early and effectively
You'll hear insights, frameworks, and stories from real workplaces — all designed to help you grow your leadership impact through communication.
🎙 With 400+ episodes, the Speak Your Mind Unapologetically Podcast is trusted by people leaders across Fortune 500s, healthcare, tech, startups, and global organizations.
ABOUT THE HOST
Ivna Curi is a Fortune 500 speaker, TEDx speaker, and host of the Speak Your Mind Unapologetically Podcast. She's a Forbes contributor, author of Unapologetic Voice, and founder of the Assertive Way Institute. A former corporate leader with an MBA from INSEAD and over 20,000 leaders trained, Ivna brings global experience and real-world strategies that help leaders drive results through bold communication.
ABOUT THE COMPANY
Assertive Way Institute helps organizations empower people leaders to lead bold conversations, influence outcomes, and build courageous speak-up cultures. Our workshops and talks help people leaders become confident, clear communicators — and turn workplace communication into a competitive advantage.
39episodes
Episodes
Newest firstAll episodes
"There Is Only One Reliable Advocate You Will Always Have — Yourself." How Harley-Davidson's Head of Motorcycle Strategy Ashwini Built Her Career Without a Long-Term Sponsor
6d ago00:46:55Tap to summarizeShe Told Her Director "Your Actions Don't Support That Opinion." He Apologized. Harley-Davidson's Ashwini on Self-Advocacy, Disrespect, and Owning Your Career She had a new director who made every interaction feel disrespectful — no matter the topic, no matter how well she was performing. It wasn't the work. It was the treatment. She hit her limit, went to her manager, and said: "There are only two paths. I have a crucial conversation with the director, or we go different directions." The meeting was scheduled. She opened by asking the director directly what he thought of her work. He praised her for two minutes. Then she said: "Your actions don't support that opinion. I don't feel respected when we interact. I don't feel wanted in this department." He was taken aback. He apologized. They reset. She went into that meeting prepared to lose her job if she had to — and she walked out with a relationship she could actually work in. Ashwini holds a bachelor's and master's in mechanical engineering from the University of Michigan. She spent over 20 years in automotive before moving to the motorcycle industry, where she is now Head of Motorcycle Development Strategy and Operations at Harley-Davidson Motor Company — one of the most male-dominated sectors in manufacturing. She is also President of the Automotive Women's Alliance Foundation (AWAF). And she will be the first to tell you she has never had a long-term sponsor. In this episode, she is completely direct about what has actually driven her career forward. You'll learn: Why she spent the first decade of her career with her head down doing great work, why it was necessary but not sufficient, and the moment she realized nobody outside her immediate area knew she had the appetite or ability to grow beyond it. Why she believes there is only one completely reliable advocate you will ever have, why most women are better at being advocates for others than for themselves, and how she built that muscle precisely because she didn't have a long-term sponsor. The full story of the disrespectful director: how she identified the problem, how she structured the conversation, why she led with "what do you think of my work?" before stating her case, and why going in prepared to lose her job is what gave her the confidence to say what needed to be said. The mentee who called her on a weekend in tears saying "I feel stupid." How Ashwini diagnosed the real problem (disrespect, not technical gaps), reached into her network to move the mentee to a different department, and how the same HR contact she helped later reached out to recommend her for a strategy role — a direct return on giving she never could have predicted. Why she describes her sponsors as "situational" rather than long-term, what that means in practice, and why she thinks the traditional sponsor model is harder to find than people admit. How she uses her role as AWAF president — where she manages an entire P&L — as a judgment-free environment to build skills that corporate rarely hands to women: financial leadership, public speaking, board-level decision making. The four A's feedback framework she uses with her leadership team: Appreciate, Assess, Action, Align — and how it prevents feedback from crossing into personal attack territory. Why she believes assertiveness and humility come from the same foundation, not opposing ones — and how saying "I don't know, and here's my plan to close that gap" has enabled her to pivot more successfully than projecting false confidence ever could. About Ashwini: Head of Motorcycle Development Strategy and Operations at Harley-Davidson Motor Company and President of the Automotive Women's Alliance Foundation (AWAF). She holds a BS and MS in mechanical engineering from the University of Michigan and has spent over two decades in engineering and strategy leadership across automotive and motorcycle industries.
Transcribe →"If You Don't Tell Us What You Want, We Can't Help You Get There." VP Erika on Breaking Out of People-Pleasing and Advocating for Your Career
2w ago00:40:40Tap to summarizeShe Won a 40 Under 40 Award and Kept It Private. It Took Her 12 Years to Say Out Loud She Wanted to Be an Executive. People2.0 VP Erika on Self-Advocacy for People Pleasers She received the SIA 40 Under 40 award. It was a big deal. And she kept it almost entirely to herself. She didn't know how to celebrate it externally without coming across as cocky. She treated it like a private accomplishment. Then she called her former leaders Kip Wright and Sunny Ackerman for advice on how to own it and talk about it. Their response changed how she thinks about her entire career: "Erika, if you don't tell the people around you — your internal sponsors, your mentors, everyone outside — we don't know how to help you get there." That conversation also came with another realization. It had taken her over 12 years to say out loud, to anyone, that she wanted to become a company executive. Not because she didn't want it. Because the impostor syndrome was that loud. Erika is VP of Strategic Account Management at People2.0, a SIA 40 Under 40 honoree, and by her own description a recovering people pleaser. She spent most of her early career waiting for leaders to notice her, navigate for her, and tap her for opportunities. It worked — until it stopped working. When she hit a plateau at Manpower, she realized: "If I didn't take those steps on my own, I would have stayed where I was at and probably gone stagnant." In this episode, she breaks down what changed and how. You'll learn: Why she kept her 40 Under 40 recognition private, what it felt like to not know how to celebrate her own win, and the mentor conversation that finally unlocked her ability to speak about her accomplishments. What it means to hit a career plateau as a people pleaser, and the moment she understood that waiting for others to drive her career was a strategy with an expiration date. Why she reached out to former leaders Kip Wright and Sunny Ackerman when she was ready to make a move, and why outside perspectives from people who know your results but are no longer your direct managers are some of the most valuable career input you can get. The 3 criteria she uses to choose mentors and sponsors who will actually move the needle for you. How she negotiated for work-life balance after years of traveling up to 90% of the time as a mother of two, and why the interview stage is the highest-leverage moment to ask for what you need. Why data-driven conversations change everything in salary and promotion negotiations: "For the past 24 months, I hit my targets at X amount" is a different conversation than "I think I deserve a raise." How to talk about your accomplishments in a way that reads as confident and grateful rather than arrogant, including what to do if you don't have formal SMART goals to point to. About Erika: Vice President of Strategic Account Management at People2.0, SIA 40 Under 40 honoree, recovering people pleaser, and vocal advocate for women owning their career narrative. She has built her career across Manpower and People2.0 in strategic accounts and sales leadership.
Transcribe →She Didn't Know Who to Pitch Her Idea To, So She Pitched Everyone. How an AWS Leader Built Alliances and Attracted a Sponsor by Talking to Anyone Who Would Listen
3w ago00:45:06Tap to summarizeShe Moved to the US with $800, Changed Her Name to Fit In, and Built a Career at Merck, Oracle, Tableau, and Amazon. Helen on Going From Terrified to Outspoken Her legal name is Hongyi, which means "the water is deep and wide." When she moved to the United States from China, she changed it to Helen so people could pronounce it more easily. She arrived with $800. She was terrified. At grad school, she barely had to speak. Then she entered the workforce. Her first significant feedback at Merck: "You need to improve your communication." She was too intimidated to ask what that meant. So she made assumptions, started listening to radio broadcasts during her long New Jersey to Pennsylvania commute, and repeated every word she heard, even when she didn't know what some of them meant. She also completely changed how she structured her thinking: lead with the statement, give details only if someone asks. Helen is now Head of Data Analytics Partner GTM at Amazon Web Services. She has built her career across Merck, Oracle, Tableau, and AWS, switching domains multiple times from chemist to engineer to customer management to partner sales. In this episode, she breaks down exactly how she got here. You'll learn: Why she was too scared to ask her first senior leader what "improve your communication" actually meant, what assumptions she made instead, and how that experience shaped the way she now gives and asks for feedback. The Oracle account management idea she developed during the 2008 financial crisis, why she had no idea who to pitch it to, and what happened when she decided to pitch it to everyone who would listen: "I talked to anyone and anyone. And it worked." How that pitching-to-everyone strategy led her to the sponsor who first backed her idea, then backed her career, and why she believes sponsors select you rather than the other way around. The three factors she attributes to attracting a sponsor: visibility (being seen under pressure), adding value to the sponsor specifically, and consistency doing simple things reliably rather than many things sporadically. The senior Oracle executive who told her "everything can be simplified into three bullet points" and why that one insight transformed how she communicated with leadership for the rest of her career. What it actually looked like behind the "fast career" others saw from outside: 15-hour days, PowerPoint decks rebuilt at 4am and still not good enough, and switching domains so many times she felt perpetually behind. Why she credits letting other people shine and giving credit generously as one of the most underrated career moves she made, and how she discovered it mattered more than she expected. Her three closing principles: know your superpower, find your passion, and pay it forward because we have all been helped up the ladder at some point. About Helen: Head of Data Analytics Partner GTM at Amazon Web Services, Helen has built her career across Merck, Oracle, Tableau, and AWS, moving from chemistry to computer engineering to enterprise sales to partner leadership. An immigrant who arrived in the US with $800, she now mentors and sponsors others on the same journey.
Transcribe →Speaking Up Doesn't Have to Be Heroic: How PVH VP Shatabdi Uses Small Moments of Courage to Shape Cultures, Careers, and Global Teams
4w ago00:44:12Tap to summarizeShe Asked Her CIO for a New Challenge at Lunch. Got a "Poison Chalice" Role. Flew to Japan in December 2019. Beat COVID by Three Weeks. PVH VP Shatabdi on Small Acts of Courage With Big Consequences. At a lunch with her CIO, she asked a simple question: "Is there a specific role where you need help? I'm ready to take a new challenge, even change my domain completely." The answer was an invitation to lead PVH's global SAP/ERP transformation across Japan, Hong Kong, Taiwan, China, and North America. She had no team in Asia Pacific. She had less than two months to build one remotely from the United States. People in the room called it a poison chalice. She flew to Japan in December 2019, got the team in place, flew home in January 2020. COVID hit weeks later. She had made it by the skin of her teeth. That is one story. But Shatabdi, VP of Global Application Engineering Services at PVH Corp — home of Tommy Hilfiger and Calvin Klein — believes the more important stories are the small ones. The under-60-second moments. The ones that most senior leaders stay quiet through. In this episode, she shares both kinds. You'll learn: A woman in a meeting quietly mentioned her son kept missing his classes because someone kept scheduling meetings after 5 PM. Shatabdi backed her up in under a minute. That intervention spread into a best practice across PVH's global time zones including Hong Kong and Bangalore. Why she credits a single direct ask at a CIO lunch for the entire trajectory of her VP career, and what she said that made the difference between getting an opportunity and being overlooked. How she heard people call her new role a "poison chalice" and responded by using their doubt as fuel: "If my leaders believe in me, I should believe in myself." What happened when a co-op intern named Christopher walked into her office and told her the access request process could be simplified to save significant man hours — and added that an AI solution could auto-fill the whole thing. She was amazed. She calls it reverse mentorship. The moment her longtime colleague Brian McGrath introduced her in a room by saying "if she's in the meeting, I know it's going to go positive" — and why that kind of public acknowledgment primes an entire room to actually listen to you. The "we vs. I" leadership model she uses: collaborative "we" language for collective goals, firm "I" language for deadlines and deliverables. And why learning when to use which one took her longer than developing either. How she structures team communication across three levels — broad town halls, staff meetings that start with "how's your family?", and one-on-ones where she opens up first about her own week — to build the kind of trust that makes honest feedback land well in both directions. About Shatabdi: Vice President of Global Application Engineering Services at PVH Corp, the fashion company behind Tommy Hilfiger and Calvin Klein. Shatabdi leads a global team across North America, Europe, Hong Kong, and Bangalore. She previously led e-commerce at Hitachi Consulting and at PVH before pivoting into global ERP transformation leadership.
Transcribe →On Her First Day, They Dismissed Her Idea. Six Months Later, She Had the Budget, the Buy-In, and a Legacy That Outlasted an Acquisition. CHRO Deepashri on Getting Your Ideas Heard
Jun 1200:47:39Tap to summarizeHe Interrupted Her Mid-Sentence and Said "I Don't Agree." She Asked: "How Many Recruitment Drives Have You Led?" CHRO Deepashri on Standing Your Ground It was her first day in a new role. The leadership team was deep into planning the launch of a major production system. She raised her hand and asked: "What about the people strategy?" Everyone looked at her like she was speaking a different language. "What does people have to do with this? It's a manufacturing system." She asked again. Still dismissed. Still polite. Still ignored. She could have let it go. Instead, she spent six months building an irrefutable business case. She spoke to the consultants. She researched the ROI. She calculated exactly what would be lost if people failed to adopt the system. She pre-worked the stakeholders she already had relationships with, one by one, so she would not be the only voice in the room when the moment came. Then she walked into a meeting with the global head of manufacturing, the global head of HR, and the other senior sponsors. She was the only woman in the room. She was a nervous wreck. She had her game face on. She got the budget. She got the resources. She built a people pillar that outlasted her, survived an acquisition, and is still running today. Deepashri is Chief Human Resources Officer at 8th Ave Food and Provisions. In this episode, she shares two very different stories of standing her ground at work — one strategic and six months in the making, one instinctive and decided in seconds — and what she learned from both. You'll learn: Why she refused to use HR buzzwords like "empathy" or "doing the right thing" when pitching to hard-nosed manufacturing executives, and what she said instead to make her idea impossible to ignore. The pre-meeting strategy she uses before any high-stakes pitch: influence the people you already have relationships with one-on-one first, so you are never the only advocate in the room. How she walked into the biggest pitch of her career feeling like a nervous wreck, knowing that if she failed, she would be "just another person on the leadership team with no voice." The investment banker who interrupted her mid-sentence and said "I don't agree." What she said back, why she still calls him a friend today, and what happened when she pulled it off. Why she thought she was being assertive in a conversation that completely failed to land, what her coach told her, and the three-part technique she developed to deliver the most difficult messages in a way that registered clearly without feeling disrespectful. Why assertiveness looks and sounds different across cultures, and how she learned to calibrate between India's indirect communication style and the blunt directness expected in U.S. corporate environments. Her best career compliment: "Deeps will tell you the most difficult things in the nicest possible way." About Deepashri: Chief Human Resources Officer at 8th Ave Food and Provisions, Deepashri has built her career across global HR, change management, and organizational transformation roles in India and the United States. She is a coach, storyteller, and advocate for assertive communication across cultures.
Transcribe →She Trembled for 60 Minutes Straight in Front of 60 Students. She Went Back the Next Day. Thomson Reuters CTO Anuradha on Facing Fear and Disrupting Yourself First
Jun 500:45:15Tap to summarizeDisrupt Yourself Before Someone Else Does: How Thomson Reuters CTO Anuradha Turned Fear, Bias, and Discomfort Into Career Fuel She grew up in a small town in India, first daughter in a middle-class family, educated in her mother tongue through 10th grade. She was culturally trained to listen more and speak less. Then she accepted a role as an assistant professor straight out of university, in front of 60 students, because she needed a job and couldn't say no to an opportunity. She showed up for her first class and trembled for the entire 60 minutes. She didn't quit. She went back. She sat in her colleagues' classes to watch how they taught. She asked hard questions. She sought feedback from the students whose faces told her everything. Eventually, students started telling her: "No one ever taught this subject the way you do." Anuradha is Head of Engineering and CTO of the Corporate Tax and Trade Technology Group at Thomson Reuters. She has since moved internationally alone, changed industries multiple times, and built a leadership philosophy around one core principle: disrupt yourself before someone else does it for you. In this episode, she breaks down how. You'll learn: She asked for a Senior Director role and was told not only no, but "even if you applied, they wouldn't hire you." What she said next, why she didn't confront him, and how she used that conversation to get clarity about whether the problem was her or the environment around her. The mental model she uses every time she gets a no: is this about me not having the skills, or is this about the climate in this organization not being ready for someone like me? Both are valid answers, but you have to know which one before you decide what to do next. Why she deliberately paced herself after that conversation, asked for names of other people to speak to, and processed it over days rather than trying to resolve it all in one go. Why running away from fear doesn't make fear disappear. It just means you'll face it later, under higher stakes, with fewer second chances. How she built confidence and humility simultaneously by changing industries repeatedly: retail, financial services, banking, payments, tax and trade. The more she learned, the more she understood how much more there was to learn, and why she sees that as a leadership asset, not a liability. What she means by "disrupt yourself before someone else does" and why it applies equally to personal growth, career management, and technology leadership at scale. Her model for leading through failure: look forward first, understand what went wrong second. And why leaders who impose their own stress on a team under pressure take everyone down with them. About Anuradha: Head of Engineering and CTO of the Corporate Tax and Trade Technology Group at Thomson Reuters, Anu is a recognized tech executive and speaker at women's leadership and technology conferences. She has built her career across multiple industries and continents.
Transcribe →They Said No — Here's Exactly What to Say Next (8 Steps to Overcome Workplace Resistance)
May 2900:37:41Tap to summarizeGetting a "no" at work isn't the problem. Not knowing what to do with it is. In this episode, you'll get a proven 8-step framework to turn workplace resistance into genuine cooperation — without pressure, without losing your composure, and without damaging the relationship. Whether you're asking for a raise, requesting flexibility, pitching an idea, advocating for resources, or handling a performance review objection, these steps give you a repeatable approach for any high-stakes conversation where the stakes feel too high to get it wrong. In this episode, you'll learn: How to recognize workplace resistance — even when it's subtle, indirect, or disguised as agreement The most common mistakes that kill your credibility and close the conversation down How to ask the questions that surface the real concern, not just the surface objection How to address objections confidently without being aggressive, passive, or overly apologetic The exact 8-step framework to move someone from "no" to "yes" while keeping the relationship intact If you've ever left a workplace conversation feeling like you gave up too easily — or pushed too hard — this episode is for you.
Transcribe →She Waited for Someone to Offer Her a Promotion. Nobody Did. Ceridian SVP Geetanjali on Owning Your Career
May 2200:44:08Tap to summarizeA Recruiter She Never Asked for Advice from Told Her to Lower Her Ambitions. It Derailed Her for Months. What Geetanjali Learned About Who Gets to Define Your Ceiling. She was doing great work, getting strong reviews, and waiting for someone to recognize she was ready for the next level. Nobody came. Finally, she went and asked. They said: "Yeah, we think you're ready." She walked away with one permanent lesson: no one knows where you want to go unless you tell them. Your manager cannot promote you toward a goal they don't know you have. Geetanjali is SVP of Financial Planning and Analysis at Ceridian, and she has built her career across multiple industries, companies, and cities, often following her spouse's career moves and rebuilding her network from scratch each time. She has been told she had no career path because of a commute. She has had a recruiter give her unsolicited opinions about her ceiling — someone who had never worked with her and didn't even have a position for her. Both times, she fact-checked herself, pushed back, and moved forward. In this episode, she gets specific about how. You'll learn: Why she walked out of her first promotion conversation wondering why her manager didn't just offer it, and the mantra she built from that moment: "I own my career." How she separates "I can't do this" from "I don't want to do this" — a distinction her husband called her out on, and one that completely changes how you diagnose self-doubt. The worst-case scenario mindset she uses every time asking feels too risky: maximum they say no, and then at least you know exactly what you need to work on. The recruiter who told her to stay put and aim lower, without her asking for any of that advice, and how she spiraled — until she realized: this person has never worked with me, doesn't know what I do, and has no position for me. Why am I listening? The manager who told her she had no career because she was commuting. How she found a better position, and what she said in her exit interview when the CFO asked why she was leaving. How she negotiated leaving at 5 PM sharp with a male manager who was more supportive than she expected — and why building trust first is the prerequisite for every other ask. Her salary negotiation rule, applied to every job offer she has ever received: never accept in one go, always go back at least once, and negotiate the full package not just the base number. How she leads her team by modeling openness about her own mistakes first, which makes it safe for her team to take risks and tell her when she is wrong. Her networking approach: stay in touch with mentors even after years of silence, get involved in community organizations when you move cities, and commit to one lunch a month with someone new. About Geetanjali: SVP of Financial Planning and Analysis at Ceridian, Geetanjali has built a finance leadership career across multiple industries and cities. She is a dual-career couple partner, working mom, woman of color from India, and active member of the Association of Financial Professionals.
Transcribe →"Success Isn't About Who You Know. It's About Who Knows You." How a J&J Senior VP Went from Waste Picker to the Top
May 1500:46:46Tap to summarizeHis Boss Told Him He'd Never Rise Above Engineer Level. Three Years Later, That Boss Reported to Him. Samuel Santos on Getting Noticed at Work Early in his career, his manager told him the company had a prototype for success: blonde hair, green eyes. Samuel Moody Santos was mixed race, Black, an immigrant who had started his working life as a waste picker. His manager told him he would never advance past engineer level. Three years later, Samuel was a manager and that man reported to him. He went on to retire as Senior Vice President at Johnson & Johnson, one of the top 40 Fortune 500 companies in the world. He speaks five languages. He holds an engineering degree and an MBA. And he wrote the book on how he did it: "In Spite of the Headwinds." In this episode, Samuel shares the specific mindset shifts, communication strategies, and career moves that took him from invisible to indispensable, as a minority, an immigrant, and someone who was actively told he didn't belong. You'll learn: Why "success depends on who you know" is the wrong mental model, and the one-sentence reframe Samuel used to challenge a corporate trainer in a room of 40 people that changed how he thought about visibility for the rest of his career. Why doing excellent work and staying quiet about it is the same as doing nothing, and how he marketed his ideas without ever bragging about himself. How he turned a direct manager who tried to limit his career into a stepping stone by building relationships with leaders two and three levels above that manager. The "poor photograph" framework: why being visible without being skilled fails, and why being skilled without being visible fails just as badly. Why he treats every "no" the same way: either he didn't explain the idea well enough, or he needs a different audience. The Starbucks founder knocked on 242 doors. Samuel applied that same logic to ideas inside a corporation. How he disagrees with superiors without triggering defensiveness: "I never disagree with any person. I disagree with ideas." The specific language he used to pose challenges as questions so people moved toward his position instead of defending against it. The performance review confrontation where someone tried to penalize a team member for a mistake from two years prior, and how Samuel addressed the entire room to win that argument on the spot. Why he focused ruthlessly on the one skill he could take above average (presenting technical ideas to non-technical executives), and chose not to develop things that wouldn't move the needle, including declining to learn Mandarin during a two-year assignment in Shanghai. About Samuel Moody Santos: Retired Senior Vice President at Johnson & Johnson, Samuel is an engineer, MBA, minister, polyglot (five languages), honorary consul, former university professor, public speaker, and author of "In Spite of the Headwinds: My Journey from Waste Picker to Vice President at a Top-Forty Fortune 500 Company." Book: https://www.amazon.com/Spite-Headwinds-Picker-Senior-Executive-ebook/dp/B09KGRQ61W Connect with Samuel on LinkedIn: https://www.linkedin.com/in/samuel-moody-santos-56601a10/
Transcribe →She Told Both Job Interviewers She Wanted to Be CIO. They Hired Her Anyway. Calendly's Head of IT Darlene on Being Unabashedly Ambitious
May 800:44:50Tap to summarizeHer Dad Found a Rolex and Returned It. What That Taught Her About Asking for Everything. Her father came to the United States in 1989 with next to nothing. He found a Rolex in a locker room while working as a janitor and returned it. The owner gave him a job. He stayed 27 years. In that time, he asked his employer for a green card. They sponsored it. He asked for college tuition. They paid for his associate's and his bachelor's degree. He asked to pivot into chemistry. They made a role for it. Darlene watched all of this and had one thought: if he could ask for all of that with nothing in his pocket and no English, why was she self-editing her ambitions? She stopped. Now she opens job interviews by telling the people who will decide whether to hire her exactly what she wants: to be CIO of an organization. She told her future boss. She told the Calendly interviewer. Both were supportive. She uses it as a filter. Darlene is Head of IT at Calendly, and in this episode she breaks down the frameworks she's built for speaking up, pitching ideas, and asking for exactly what she wants without apology. You'll learn: How to know which conversations are worth inserting yourself into, and which ones to let go based on span of control, stakeholder complexity, and how badly you want the outcome. The self-interest framework: why "selfless" leads to burnout, "selfish" kills collaboration, and the middle zone of self-interest is where real buy-in happens. Why she describes senior leadership as "glorified salespeople" and what changed when she stopped clicking on the backend and started selling visions instead. The "directionally correct" approach to numbers: why giving a C-suite executive "$270K plus or minus 20%" is infinitely more persuasive than "decreased time" or a 6-decimal-point calculation that took two weeks to produce. How self-editing language like "I think the answer might be..." quietly signals low confidence, and how to hit the delete button on it. Why she tells every interviewer exactly what she wants out of her career, and how she uses their response as a filter for whether the organization is actually a place where she can grow. About Darlene: Head of IT at Calendly, Darlene has built her career at the intersection of technology leadership and organizational influence. Originally from a Venezuelan family in Rhode Island, she leads IT strategy and operations at one of the most widely used scheduling platforms in the world. She is candid, direct, and unabashedly ambitious.
Transcribe →