He 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.

Disrupt 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.

Getting 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.

A 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.

His 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/

Her 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.

She missed the scholarship deadline for her MBA. She asked anyway. She got it. She was the only woman in her group project cohort, a single mom with a one-year-old, living paycheck to paycheck. She told her group on day one exactly what she could do and when she was leaving. They respected it. On a business trip with a relatively new manager, she admitted mid-conversation that she wanted to move into a strategy role that didn't even exist yet. That manager became her greatest champion. That pivot launched the career that led her to become Chief Strategy and Innovation Officer at Lee Health.

Lisa has spent her career figuring out what fearless authenticity actually looks like in practice: not as a concept, but as a set of specific choices made in specific moments of risk. In Part 1 of this two-part conversation, she walks through the mindset shifts and early career moves that built her foundation.

You'll learn:

• The exact moment Lisa realized intimidation was her own internal problem, not something others were doing to her and how that realization changed every difficult room she walked into after
• Why the post-it on her monitor reads "no one wants to feel insignificant, incompetent, or unlikable", and how she uses it to decode defensiveness in herself and others
• The MBA-as-single-mom stories: how she advocated for a scholarship she'd missed the deadline for, set hard boundaries with her group project team from day one, and created an independent study that wasn't in the curriculum
• How a candid conversation on a business trip, admitting she wanted a completely different role, launched her entire strategy career, and what she learned about speaking up to managers about your real aspirations
• Why her first attempt at people management felt completely wrong, and the leadership philosophy she arrived at: "developing leaders, not amassing followers"
• How conflict made two of her most important professional relationships stronger, not weaker

About Lisa: Chief Strategy and Innovation Officer at Lee Health, Lisa leads strategic planning, innovation, and organizational transformation across one of Florida's largest health systems. She is a passionate advocate for women in leadership and women of color in senior roles.

The Mirror Method, the WAIT Acronym, and Why "Learn Fast" Beats "Fail Fast": Lee Health CSIO Lisa on Challenging the Status Quo — Part 2

She walked into a conference room as the only woman in a room full of men in technical data roles. They introduced themselves to each other and started the meeting without acknowledging her at all. She paused, said "excuse me," stated her name, her role, and why she was there. It startled them. She was glad she did it. Because if she hadn't, she wouldn't have belonged in the conversation that followed.

In Part 2 of this conversation, Lisa, Chief Strategy and Innovation Officer at Lee Health, moves from personal story into the specific leadership tools she uses every day to challenge the status quo, orchestrate high-stakes conversations, and move organizations through change without creating enemies.

You'll learn:

• The Mirror Method: why the most dangerous thing you can do when entering a new organization is come in with a fix-it mentality, and the structured listening approach that gets people to agree the status quo needs to change before you ever propose a solution
• WAIT — "Why Am I Talking?" — the acronym she uses to decide when her voice advances a conversation and when silence does more
• How she reads the nonverbals of an entire organization the same way she reads body language in a room, and what signals tell her when trust is building and when it isn't
• Why she stopped relying on PowerPoint and what changed when she started looking people in the eye instead of at her slides, including the mentor advice that saved her: "be ready to deliver a 5-minute version of what you just created"
• The difference between intellectual sparring and debate, and how she creates conditions for divergent thinking that actually leads to decisions, not just more discussion
• Why she says "learn fast" instead of "fail fast", and how she navigates naysayers, skeptics, and the inevitable "you paid how much for what?" moments in healthcare innovation
• What she looks for when building a team: curiosity, courage, and comfort with ambiguity, and why trustworthiness ranks above everything else

About Lisa: Chief Strategy and Innovation Officer at Lee Health, Lisa leads strategic planning, innovation, and organizational transformation across one of Florida's largest health systems. She is a passionate advocate for women in leadership and women of color in senior roles.

For years, Daisy's performance reviews said the same things: hardworking, great team player, result-driven, quiet. Cycle after cycle, different managers, same words. Then she realized: those were her brand hashtags, and they were never going to get her to where she wanted to go. She wanted "confident," "influential," "driven," "leadership." And nobody was going to give her those labels. She had to earn them by using her voice.

Daisy is Head of Strategy and FP&A at Revolut, one of the world's fastest-growing fintechs. Originally from China, she built her career navigating the cultural expectation that hard work and results would speak for themselves. They didn't. In this episode, she breaks down exactly how she changed that, and what she now teaches every junior person who reports to her.

You'll learn:

• The performance review pattern that finally made her realize she was building the wrong brand, and the specific words she decided to own instead
• Why she stopped being the silent note-taker in every meeting, what she lost by doing it, and why AI has made that role completely obsolete
• The 4-phase framework for asking questions in town halls and large meetings, from canned questions that still get you seen, to strategic dialogue that opens collaboration doors with senior executives
• The "golden three months" strategy: how to use your newness as a security blanket to ask anything, map broken processes, and deliver visible value before anyone expects it
• Why there is no such thing as over-communication at work ,and how staying quiet to avoid being "too much" is actually the riskier move
• The one mandate she gives herself and every person she mentors: say something in every meeting, even if it's just a rephrasing

If you've ever been called "hardworking" but not "leadership material," or if you have great ideas that only come out in one-on-ones but never in the room, this episode is the blueprint.

About Daisy: Head of Strategy and Financial Planning & Analytics at Revolut, Daisy leads strategic and financial operations at one of the world's largest fintech companies. Originally from China, she coaches and mentors junior professionals on speaking up, building visibility, and translating strong technical work into leadership presence.

Stop Taking Notes, Start Getting Noticed: Revolut Head of Strategy Daisy on Building Your Brand Through Your Voice

Two Ways to Fail: Give Up or Die." How Sigma Software CEO Katherine Tuluzova Built a Foreign Office, Completed a Half Ironman, and Learned to Lead on One Rule

"There are only two ways to fail: give up or die. And neither is a reasonable option."

That is the saying Katherine Tuluzova's team uses to remind themselves who they are. She means it literally. When she was trying to open Sigma Software Group's first Latin American office, she tried recruiting agencies, acquisition targets, universities, and different countries for an entire year. Nothing worked. Then in a brainstorming session, someone mentioned speaking at a developer conference. She found one in Brazil, submitted a paper, got accepted to one of the most selective conferences in the region, went, fell in love with the community, and pivoted the entire Latin American strategy to Brazil on the spot.

Then she went back to the same conference the following year and gave her talk in Portuguese. She had submitted the paper in December, in Portuguese, with a translator. The conference was in March. She did not speak Portuguese. She had three months to learn.

Katherine Tuluzova rose from junior software developer to CEO of Sigma Software Group Americas in 16 years. In this episode, she is completely direct about how she actually did it — not as a philosophy, but as a series of specific situations where she refused to stop.

You'll learn:

• How she spent a year hitting walls trying to open a Latin American office, the random brainstorming idea that changed everything, and why resolve in the goal combined with total flexibility in the approach is what finally broke through.
• Why she submitted a conference paper in a language she couldn't speak, learned Portuguese in three months with 15 minutes a day of consistent practice, and used the speech itself to encourage Brazilian engineers not to be afraid of making mistakes in English.
• The grandmother she is named after: a high-level judge described by everyone as tough, smart, and fair. Never nice or sweet. And why Katherine wants to invoke strong opinions rather than be universally liked.
• Why she believes being perceived as aggressive is an acceptable trade-off for being decisive and authentic — and where she draws the line between assertive and actually offensive.
• Her father's career advice that drives her decisiveness: "A wrong direction is better than no direction." Make the call, correct fast, keep moving.
• What she learned from completing a Half Ironman — 1.2 miles of swimming, 56 miles on a bike, then a half marathon. She was terrified of the bike, had crashes, had scars, genuinely questioned whether to continue. She finished. She signed up for another one.
• How she managed a solo transatlantic flight from Barcelona to Dallas with a one-year-old and a not-yet-three-year-old by accepting beforehand that it would be horrible — and why pre-accepting the struggle removes the frustration when it arrives.
• The two tools she uses when doubt sets in: reminding herself of hard things she has already done, and surrounding herself with people who will do the same reminding when she can't.

About Katherine Tuluzova: CEO of Sigma Software Group Americas, Katherine rose from junior software developer to CEO in 16 years. She leads the Americas expansion for a global software company originally founded in Eastern Europe, including building the company's Brazilian office from the ground up. She is also a Half Ironman finisher and a Portuguese speaker.

Connect with Katherine on LinkedIn: https://www.linkedin.com/in/katherine-tuluzova/