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Most of us check the odds before we try something big. MIT-trained engineer and serial founder Sanjay Manandhar, author of The Why Not Advantage, says that's the wrong number to look at. A statistic describes the crowd, not you.
At 16, Sanjay applied to US schools from Kathmandu. He needed a full scholarship and airfare, and his friends asked if he was nuts. In this conversation, he shares the formula he uses to rewrite his odds, what a Nobel Prize winner's 40 years of persistence teaches about timing, and why your odds change the moment you take action.
In this episode, you'll learn:
About Sanjay Manandhar: Sanjay Manandhar is a serial technology entrepreneur, mentor, and author of The Why Not Advantage: How Small Probabilities Create Outsized Outcomes. Originally from Nepal, he is an MIT-trained engineer. In 1994, he helped bring the internet to Nepal, and he has since founded and led multiple technology companies. He lives in Cambridge, MA, and loves trekking and motorbiking.
Connect with Sanjay: Book and author site: https://sanjaymanandhar.com/ LinkedIn: https://www.linkedin.com/in/sanjaymanandhar
The Why Not Advantage is available on Amazon in paperback, Kindle, and audiobook.
Mentioned in this episode: Bruno de Finetti, Italian mathematician Katalin Karikó, Nobel laureate and mRNA vaccine pioneer Bronnie Ware, The Top Five Regrets of the Dying
Know someone usure of which path to follow? Send them this episode.
Quotes from Sanjay: "Your odds change in your favor the moment you take action." "You don't get to run your venture 1,000 times or your career move 1,000 times. You have one chance, maybe two." "Negotiating with a counterparty is hard. The harder part is actually negotiating with yourself."
Chapters: 00:00 Agency, and why the odds you're quoted aren't your odds 01:17 "If you think of it, do it": his mother's advice about time 05:01 One talk to 60 people that led to an $80M startup 08:07 "Probability does not exist": the idea behind the book 10:39 The BPCA formula: why one zero sinks your odds 13:11 The Nobel winner who waited 40 years for her moment 18:05 The variable people underestimate most 19:55 Survivorship bias: is beating the odds just luck? 23:29 Why almost everyone who starts a marathon finishes 26:04 Activation energy: why water won't boil at 99.5°C 30:13 Overthinking? Any action beats the perfect action 34:00 Conviction vs. the crowd: lessons from bubbles and Theranos 39:07 The deathbed test: what you'll regret not doing
How do you disagree with a superior or your boss when you see a problem in a decision you still have to deliver? How do you influence senior leaders when you don't have the final say?
In this episode of Speak Your Mind Unapologetically, Ivna Curi explores managing up and upward influence through two real workplace stories from her book, Unapologetic Voice.
Amy spent six months building a business case after senior leaders dismissed a gap she saw in their plan. Rebecca challenged a leader's approach to restructuring by proposing an alternative that addressed his concern about confidentiality.
Their experiences reveal practical ways to challenge a decision, earn consideration for your ideas, and help your organization improve.
You'll discover:
If you're a manager, director, or VP navigating a rejected idea, an overlooked risk, or a decision you believe needs reconsideration, this episode is for you.
Share this episode with a colleague working to get a useful perspective heard, and follow Speak Your Mind Unapologetically for more on leadership communication and upward influence.
Being kind at work is easy when things are going well. Smiling, saying thank you, listening, remembering birthdays. The real test is what you do when there is a problem, a conflict, or a disagreement.
This episode is a self-assessment. Twelve everyday workplace moments that look polite on the surface and cost someone else something real. Escalating to a manager before ever telling the colleague what the problem is. Staying silent in a meeting, then criticizing the decision privately afterward. Calling someone disrespectful instead of naming the behavior. Saying yes when you mean no. Redoing a team member's work instead of telling them what to change.
The pattern underneath all twelve is the same. Avoiding an uncomfortable conversation feels like kindness to the person doing the avoiding, and transfers the cost to someone else in the form of lost information, lost time, lost reputation, or a lost opportunity.
Here is the test: if your discomfort leaves someone else worse off on information, time, reputation, or opportunity, that is not kindness.
Go through the twelve. For each one, decide honestly whether you are being kind or protecting your own comfort. Then pick one to change this week.
Key takeawaysMost people who challenge a superior's decision get it wrong. They oppose. Nita Patel, VP of Engineering at Otis, says the people who have changed her mind did something else: they stayed curious. They asked what happens after step two. They wanted to understand rather than object. By the end of the conversation she is the one asking them what they think, without realizing she was challenged at all.
That works because of the larger skill underneath it. Nita calls herself a translator, estimating 30 to 40% of her time goes to it: working out why a meeting matters, what the goal is, and which pieces of information will get someone there. The translation changes depending on whom you're speaking to. What she presents to a CEO is different from what she presents to the team building it or to a cross-functional peer.
She splits translation in two. Translating an idea to stakeholders means finding the intent and explaining it separately to each group that has to buy-in. Translating an idea into action means breaking the problem down and moving forward before the full plan is in place. She used both to launch the first IEEE Women in Engineering International Leadership Conference, arguing that sometimes you take the leap and build the wings on the way down.
She also names the Toastmasters feedback that changed her most: that she assumes too much and jumps straight to the answer. And she explains why technical leaders labeled direct or difficult are usually being read as too focused on the detail.
If you have ever had a good idea die on the way up, this episode is about the trip.
00:00 Meet Nita Patel, VP of Engineering at Otis 01:17 What Chess Teaches About Anticipating the Other Side 02:11 Know the Rules So the Unexpected Move Does Not Derail You 02:58 How to Make a Fair Call When the Rulebook Runs Out 03:56 Where Confidence Comes From in a Gray-Area Decision 04:35 Rules, Experience, Fallbacks: The Three Sources of Confidence 06:15 When Following the Process Costs You the Objective 07:30 Why the Analytically Best Move Is Not Always the Right One 09:02 How to Translate an Idea So Each Stakeholder Cares 10:25 Breaking a Big Idea Down So Others Can Act on It 10:47 Pitch Before It Is Perfect: Build the Wings on the Way Down 13:09 Hold the Why, Stay Flexible on the How 14:03 How to Challenge Your Boss Without It Feeling Like a Challenge 16:39 The Questions That Actually Change a Leader's Mind 19:39 Why "Too Direct" Usually Means "Too Detailed" 22:13 Find the Real Problem Before You Solve the Wrong One 25:56 The Feedback That Changed How She Briefs Executives 30:57 Why 30 to 40% of a VP's Week Goes to Translation 32:13 Nita's Closing Advice: Everyone Has Influence to Use
Two Ways to Fail: Give Up or Die." How Sigma Software CEO Katherine 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'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 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:
About Katherine: 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.
Her first year in corporate. She noticed her male peer was getting more technical work than her. She raised it with her supervisor — not loudly, not aggressively, just directly. Instead of addressing it with her, the supervisor took it to a broader forum and told others there was "a trouble candidate in the team." The message filtered back to her. She had asked for fair treatment and had been labeled a problem for it.
What happened next is what makes the story worth hearing. A senior leader stepped in, routed someone to talk to her properly, understood what she actually needed, and gave her a product certification project. She suspected it was a test. She treated it like an opportunity. She delivered. That quarter, she won a company excellence award.
Aditi is Managing Director at Accenture's Cloud First Data and AI Group, where she leads digital transformation for large clients. She has been called outspoken — a label she has never apologized for — and decisive, a word she noticed women rarely claim for themselves.
In this episode she gets specific about what it actually looks like to speak up when you're new, when the reception is hostile, and when the outcome is uncertain.
You'll hear:
About Aditi: Managing Director, Accenture Cloud First Data and AI Group. Digital transformation leader.
She Stopped Leading With Her Title and Started Saying "I'm a Technology and Business Diplomat." People Immediately Wanted to Know More. Equifax SVP D'Lovely on Networking, Personal Boards, and Career Infrastructure
She was laid off twice. Both times, by the time the hiring manager called her, three or four people at the company had already been talking about her. Not because she got lucky. Because she had spent months having breakfasts, following up on cold contacts, asking questions instead of pitching, and making it easy for people to pass her name along. One of those contacts had been on a month-long holiday — not ignoring her. She kept following up. They finally had lunch. That person said: "You're the real deal." She talked to people. The hiring manager called within a month.
D'Lovely is SVP of Product, Data and Analytics, and Technology Planning and Execution at Equifax, a finalist for Woman of the Year in Engineering by the Women in Technology organization, and the person who calls herself a "Technology and Business Diplomat" — a title that took years to develop and immediately makes people want to know more.
In this episode, she breaks down how networking actually works as a career infrastructure system, not a social obligation.
You'll learn:
About D'Lovely: SVP of Product, Data and Analytics, and Technology Planning and Execution at Equifax. Finalist, Woman of the Year in Engineering, Women in Technology. Self-described Technology and Business Diplomat. Based in Atlanta.
She credits three people with transforming her career trajectory at AWS and beyond. Tatiana got her into AWS. Wayne sponsored her advancement within it. Dan helped her break into venture capital as a partner at Felicis Ventures. She did not stumble into these relationships. She built them intentionally, maintained them with discipline, and gave back at every stage — even when what she could give seemed small compared to what she was receiving.
Nancy was Director and General Manager at AWS Data Protection when this episode was recorded. She has since been promoted to CTO. She is also the founder of Advancing Women in Tech (AWIT), a venture partner at Felicis Ventures, and served on the board of UPenn's School of Engineering Online. She gave the commencement speech at the University of Pennsylvania. The central idea of that speech: build your personal board of directors.
In this episode, she breaks down the full framework.
You'll learn:
About Nancy: At the time of this recording, Nancy was Director and General Manager, AWS Data Protection at Amazon Web Services. She has since been promoted to CTO. She is also the founder of Advancing Women in Tech (AWIT), a venture partner at Felicis Ventures, and has served on the board of directors of the UPenn School of Engineering Online. AWIT's Coursera curriculum has reached tens of thousands of learners globally.
Advancing Women in Tech: https://www.advancingwomenintech.org/
She came to the United States from Cameroon almost 30 years ago with a master's degree in education, almost no exposure to computers, and a goal to pursue a doctorate. Her two sisters, both already in IT careers, redirected her. She thought she could never succeed in the field. She became an IT help desk worker. Then a network administrator. Then an IT manager. Then a director. Then a CIO. Then a COO in Spain. Then a Chief Technology and Innovation Officer. Then a Vice President and CIO at a California State University. Her PhD — the original goal from 1995 — she completed in 2019. Twenty-four years later than planned.
Dr. Monique is Vice President for Information Technology and CIO at California State University, Chico, and a multiple CIO award winner. In this episode, she shares the specific moments — some planned, some forced on her — that defined how she uses her voice to steer her career.
You'll learn:
About Dr. Monique: Vice President for Information Technology and Chief Information Officer at California State University, Chico. Multiple CIO award winner. Immigrant from Cameroon. Former CIO at Colorado School of Mines, Chief Technology and Innovation Officer, and Chief Operating Officer in Spain. PhD in Education and Organizational Leadership. Started her IT career at the help desk.
Her Peer Kept Misattributing Statements to Her Team. She Let It Slide Once. The Second Time She Confronted Her Directly.
She had a verbal offer within four days. They were eager. Before she accepted, she called HR and said: "Before I accept, I want to speak with my manager's manager." That request could have cost her the role entirely. She had already weighed it: if they say no, that tells me everything I need to know about this culture. If they say yes, I make a more informed decision. Within 24 hours, the executive cleared his calendar during a conference lunch and took a 30-minute call. He opened with: "What questions do you have for me?" She asked everything. She took the job.
Saadia is Global Chief Information and Technology Officer at Coverys, a medical liability company, with 20 years of IT experience across multiple Fortune 100 companies. In this episode, she walks through the specific moments in her career where courage was required — and exactly how she built it.
You'll learn:
About Saadia: Global Chief Information and Technology Officer at Coverys, a medical liability company. Saadia has 20 years of IT leadership experience across multiple Fortune 100 companies and is a recognized voice on courage, leadership, and building speak-up cultures in technology organizations.
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