From a Woman to a Leader

Limor Bergman Gross

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From a Woman to a Leader is the women in tech leadership podcast — honest conversations with senior women in tech about promotions, visibility, and leading without burning out.

4 days ago

How to Sell When You Hate Selling (Emily McSherry) | From a Woman to a Leader

You know you should be putting yourself out there. Pitching the idea, asking for the meeting, telling people what you're working on. And you keep not doing it, because some part of you is waiting until it's more polished, more proven, more ready. Emily McSherry built her prototype for under a thousand dollars and sold it to five universities before it had a single feature that makes it impressive today. She started her career doing 500 cold calls a week, and she'll tell you plainly that 80 percent of whether it works is what's going on in your head before you pick up the phone. This conversation is the practical version of "stop waiting." Not a pep talk, but the actual mechanics of how you ask. In this episode: Why testing your assumptions is cheaper and faster than building the thingWhat "good enough to sell" actually looks like, and why it's much less finished than you thinkThe difference between pitching at someone and asking them a question, told through a story about buying shoesWho to go to first when nobody knows who you are yetThe two versions of you that can walk into the same conversation, and why only one of them gets a yes About Emily:Emily McSherry is the founder and CEO of Advize, a platform that helps students learn about careers by watching short video interviews with people actually doing the job. She grew up in a small town in rural Texas where she had no idea what was possible, did everything right in college, and still left feeling lost. She then spent close to a decade in recruitment in Los Angeles, training recruiters how to headhunt, which is where she figured out that the fastest way to learn about a career is to ask someone questions about it. Advize now holds over 12,000 video interviews. Connect with Emily: LinkedIn: https://www.linkedin.com/in/msemilymcsherry/Advize: https://advizehub.com Connect with Limor: Website: https://limorbergman.comPodcast: https://limorbergman.com/podcast/LinkedIn: https://www.linkedin.com/in/limorbergman/Substack: https://limorbergman.substack.com Search terms: how to sell when you hate selling, how to pitch your idea, getting your first clients, selling before your product is ready, cold calling confidence, women in tech sales, how to ask for what you want at work, minimum viable product
6 days ago

Eleven Months to Go Part-Time — Wendy Cocke on Making Flex Work

"The business does not care that you want to pick your child up at 3:30. They don't care. But what they do care is that whatever they want delivered is delivered." Wendy Cocke said that to me and I flinched a little. Then I thought about every version of this conversation I've had — in my own career and in years of coaching sessions — and she's right. Wendy is a chemical engineer, the founder of Engineering Leadership Solutions, and the author of Making Flex Work: Defining Success on Your Own Terms and Reimagine Your Work. She spent about a decade following the prescribed path before she stopped to ask whether she wanted any of it. Then it took her eleven months to get her first flexible work arrangement — and once she had it, she got promoted more and faster than she had in the previous ten years. This is a practical conversation. Wendy is an engineer, so her answer to "my employer isn't flexible" isn't to feel less. It's to bring data. What we cover: Why most of us never even ask — and what she did instead of quittingThe eleven-month fight for her first flexible arrangement, in a company that had a policy that wasn't meant for people like herWhy she hid it once she got it, and why she calls that naive now"They said generally they would have given me a solid B plus" — the gap between how you grade yourself and how everyone around you sees youDefining success on your own terms, and why running four people's scorecards at once guarantees you fail all of themStep one: seven days of journaling. Hours AND span — earliest start, latest stop. "Six hours compressed feels very different than six hours across sixteen hours."Why most people who feel overwhelmed are already working more than they're paid for — so the first move usually isn't part-time; it's getting back to full-timeThe VP who works 6- 11 a.m. and 8 p.m.- midnight on purpose, because her peers are in Europe and her team is in AsiaWhy leaders resist: we never trained them to lead flexibly, and asynchronous work means they have to get the request right the first time"Leading with your eyeballs" — and the people who are present, active, and completely unproductiveLeveraging small changes: experiments so small nobody has to approve them. "It's like boiling a frog."How to turn an emotional ask into a business proposal: this is what I want, this is what I know you need, here's how we both get itThe man near retirement whose wife found her dream house in another city — and how they turned his problem into a business case the company said yes to"You own a business that sells exactly one product, and that product is you" Find Wendy: makingflexwork.com — free templates, including an outline for building the business proposal she describes in this episodeEngineering Leadership Solutions — her company Connect with Limor: Website: https://limorbergman.comPodcast: https://limorbergman.com/podcast/LinkedIn: https://www.linkedin.com/in/limorbergman/Substack: https://limorbergman.substack.com Search terms: flexible work, part-time work, working mothers, women in tech, women in engineering, work life balance, negotiating flexibility, remote work, leadership, career growth, mom guilt, defining success
1 Sept

Why Women Keep Getting Told They're Not Strategic Enough | Jill Avey

Someone told you that you're not strategic enough. Maybe it was in a review, maybe it was said casually in a hallway, and maybe it has been sitting with you ever since. What made it so frustrating is that nobody explained what they meant, or what you were supposed to do differently on Monday morning. Jill Avey heard the exact same thing. She had spent fifteen years as a marketing strategist; strategy was her specialty, and she was still criticized for not being strategic enough. What she figured out was that she had been strategic the whole time. She just wasn't communicating it in a way anyone could see. As she says in this episode, it was happening on the inside, and nobody could see it on the outside. In this conversation, we get specific about what strategic thinking actually looks like when you put it on a calendar, why women get rated lowest on this one competency, and the sentence you can stop saying in meetings this week. What you'll take away: Why "you're not strategic" is almost never about your thinking, and almost always about what people can seeThe one leadership competency that decides who succeeds as an executive, and why women rank at the bottom of itWhy the shift from doing to leading is so much harder for women, and what we were trained to do insteadThe two areas Jill sees women score lowest on, and the exact habits that fix themHow to use AI to run your future thinking once a month, in the time you actually haveThe language shift that makes the same work sound strategic to the people above you About Jill Avey:Jill is a women's leadership coach with an Ivy League MBA and the founder of SisterSmart. She has spent more than twenty years working with leaders in Fortune 100 companies, and she is one of the first hundred coaches certified in the Big 5 of Strategy assessment. She built the Strategic Leadership Lab for Women around the exact problem in this episode. Connect with Jill: Strategic Leadership Lab (starts September 11): https://sistersmart.com/slaLinkedIn: https://www.linkedin.com/in/jillavey/Substack: https://jillavey.substack.com/YouTube: SisterSmart Leadership, https://www.youtube.com/@jill_avey Connect with Limor: Website: https://limorbergman.comPodcast: https://limorbergman.com/podcast/LinkedIn: https://www.linkedin.com/in/limorbergman/Substack: https://limorbergman.substack.com Searches this episode answers: what does it mean when your boss says you're not strategic, how to be seen as strategic at work, how to be more strategic as a leader, strategic thinking for women in tech, why women get passed over for executive roles, how to demonstrate strategic thinking in meetings.
27 Aug

Don't DIY Your AI: Anne Cantera on Adoption Without the Hype

"A Copilot license is not an AI strategy." Anne Cantera has the t-shirt to prove it. Anne is the founder of Elemental Intelligence. She's been inside enterprise AI projects that went sideways, mentors hundreds of designers, and has an unusually low tolerance for hype — she calls the last three years "the messy middle," and thinks we're finally on our way out of it. In this conversation, we get into what leaders keep getting wrong about AI adoption, and what individual contributors should be doing right now if they're worried about staying employable. What we cover: Why "don't DIY your AI" is the whole message to leadership — and what hiring an expert early actually saves youThe two things every AI strategy needs first: an outside expert, and a real governance plan. "The strategy is the plan, and governance is the rules."Why smaller companies are better positioned than enterprise right now — it's easier to turn a motorboat than the TitanicWhat Anne tells designers who are afraid the machines are taking their jobs (the risk isn't AI, it's static-screen thinking)Why upskilling beats applying: "It is easier to upskill than it is to apply for thousands of jobs and never hear back"How to time box 90 minutes a day for learning without burning out — and why she calls it a mental health hackThe number one AI skill nobody lists on a job description: knowing what to pay attention toHow to tell an expert from an influencer in about eleven secondsGrooming your LinkedIn feed so it becomes free education instead of an anxiety machineWhy your LinkedIn headline is SEO, and why you should never pay anyone to optimise it for youThe unpaid day-and-a-half "assignment" Anne turned down, and the three-day paid trial she thinks should replace it Chapters: 00:00 Welcome00:30 What the AI hype actually got wrong02:45 The mistakes leaders keep making — "don't DIY your AI"07:25 Start with governance: the plan versus the rules12:15 "If we keep thinking in static screens, designers are not going to have work"12:45 Why upskilling beats applying to thousands of jobs18:40 The #1 AI skill: knowing what to pay attention to24:00 Experts versus influencers — how to vet who you follow25:00 Touch grass: it's a marathon, not a sprint26:45 Your LinkedIn headline is SEO30:00 Groom your feed35:55 The unpaid assignment, and a better way to hire39:00 Where to find Anne Everything Anne recommended, all free: voiceofai.io — her upskilling site for designers. No email required; she makes nothing from it.https://agentics.org/— the Agentics Foundation. Their Friday hackerspace is a show-and-tell of what people are really building.Conversation Design Institute (https://www.conversationdesigninstitute.com/) — free and low-cost conversation design classes.Rosenfeld Media (https://rosenfeldmedia.com/)— her talk on the new design stack and omnimodal design, plus a lot of free material.DESIGNathon — Anne's podcast. Hard to find on YouTube (it lives inside the Swarm community), but it's on Apple and Spotify. Connect with Anne: https://www.linkedin.com/in/anne-cantera/ Connect with Limor:Website: https://limorbergman.comPodcast: https://limorbergman.com/podcast/LinkedIn: https://www.linkedin.com/in/limorbergman/Substack: https://limorbergman.substack.com Search terms: AI adoption, AI governance, AI strategy, upskilling, women in tech, career change, UX design, conversation design, job search, LinkedIn optimization, leadership
25 Aug

How to Be Visible at Work Without Bragging - Susan M Barber

You have been telling yourself that if you keep doing excellent work, someone will eventually notice. That is what most of us were taught. It is also why so many capable women watch someone with a louder voice get the project, the promotion, and the room. Susan M. Barber was named top talent in IT at a Fortune 500 company, and then a mentor sat her down and told her she wasn't being visible, wasn't talking about her work, and asked why she even bothered coming to the meetings. In this conversation, she walks through exactly what she changed, and none of it involved becoming a different person. We get specific about the words you use that quietly shrink your own work, the two-minute prep that gets you speaking up in meetings, and a weekly framework you can start on Monday. In this episode: • Why does "it's no big deal" cost you more than you think, even when you spent two years on it?• How do you talk about your work without it sounding like bragging?• What do you do when you freeze trying to think of the perfect thing to say in a meeting?• Why is deflecting a compliment the same as dismissing the person who gave it?• How do you make sure your team gets credit, and why is that on you?• What is the VALUE framework, and how do you run it in one week? About Susan: Susan M. Barber is a leadership visibility expert and a former Fortune 500 IT director. She spent years at Kraft moving through sales, supply chain, and food service before landing in technology, and she assumed for a long time that she didn't belong at the table because her degrees were in marketing and management. She now works with high-performing leaders on communicating their value strategically, and she is the author of The Visibility Factor and the workbook Your Journey to Visibility. She hosts The Visibility Factor podcast. Connect with Susan:Website: https://susanmbarber.com/LinkedIn: https://www.linkedin.com/in/susanbarbercoaching/Podcast: The Visibility FactorBooks: The Visibility Factor, and the workbook Your Journey to Visibility Connect with Limor:Website: https://limorbergman.comPodcast: https://limorbergman.com/podcast/LinkedIn: https://www.linkedin.com/in/limorbergman/Substack: https://limorbergman.substack.com Search terms: how to be visible at work, self promotion without bragging, why am I not getting promoted, how to speak up in meetings, minimizing language at work, how to accept a compliment at work, executive presence for women, visibility at work for introverts, getting credit for your work, women in tech promotion
24 Aug

Why Women Stop Trusting Themselves at Work - Karen Ann Bulluck

Have you ever caught yourself putting on a different personality the moment you walk into a meeting? Speaking more carefully, feeling less, holding back the thing you actually think, because that's what a leader is supposed to look like? And then wondered why leading feels so exhausting? My guest is Karen Ann Bulluck, the first woman promoted to Executive Vice President at AM Best Company, who left the corporate world to write novels about it. Her Ascending Ladders series follows women leaders facing the ethical dilemmas nobody puts in a leadership book. We talk about the disconnect between who you are and who you're performing as, why the corporate world taught us all to stuff our emotions down, and the moment HR told Karen to fire an employee who walked out of the building for three days — and what happened when she didn't. And we go deep on trust. Not trusting other people. Trusting yourself. In this episode: - Why so many women believe trusting themselves means never making a mistake, and why that's backwards - The disconnect between who you are inside and who you're forced to be at work, and what it costs you - The employee who walked out for three days, and why Karen refused to fire him - How to set boundaries as a leader without turning into a different person - Why remote work makes real trust harder, and what you have to do on purpose now - What fiction can say about women's leadership that a how-to book never could About Karen: Karen Ann Bulluck is a best-selling author, speaker, and founder of DARING TO TRANSCEND®. She was the first woman promoted to Executive Vice President at AM Best Company before leaving corporate to write fiction about women's leadership. She is the author of Discovering Power, Pursuing Truth, and Embracing Trust — the Ascending Ladders series — and a contributing author to three international bestselling anthologies. Connect with Karen: LinkedIn: https://www.linkedin.com/in/karenannbulluck Website: https://www.daringtotranscend.com Free resources and blog: https://daringtotranscend.com/resources Books: available on Amazon, Barnes & Noble, and in ebook, paperback and audiobook Connect with Limor: Website: https://limorbergman.com Podcast: https://limorbergman.com/podcast/ LinkedIn: https://www.linkedin.com/in/limorbergman/ Substack: https://limorbergman.substack.com Search terms: how to trust yourself, women in leadership, self-doubt at work, authentic leadership, setting boundaries as a leader, emotions in the workplace, integrity at work, leaving corporate, women leaders, building trust remote teams.
11 Aug

Confidence Doesn't Come From Competence | Tori Jenae | From a Woman to a Leader

Everyone tells you confidence comes from competence. Do the work, get good, and the feeling will follow. Tori Jenae doesn't buy it. She has three psychology degrees, ran HR for a 7,000-person company by the age of 30, and has spent 14 years coaching high achievers — and what she sees is women who are objectively excellent and still waiting to be found out. Her argument: confidence isn't built on competence. It's built on resilience, and on healing whatever shook your confidence in the first place. In this conversation we get very specific about where self-doubt actually comes from, and what to do with it on a normal Tuesday. In this episode: • Why doubt shows up every time you level up — and why that's the correct response• The "badass list": 20 things you were scared of and did anyway, and why it works• Why big swings fail and 1% a week doesn't — the brain science behind self-sabotage• How one sentence from a fifth-grade teacher shaped 18 years of what she believed she could do• The difference between "vent up" and "vent down," and who you should actually be talking to About Tori: Tori Jenae is a Transformational Life Strategist with three degrees in psychology, a background in HR leadership, and deep training in Energy Medicine, functional medicine, nervous system science, and spiritual development. Born into a world of addiction and trauma, she rebuilt her life from the ground up at 17, completely sober and entirely self-funded. She has been coaching since 2010, working holistically across identity, relationships, business, family, and health. Clients stay with her for years, refer their spouses and children, and credit her in published books. She works with international clients from Beverly Hills, California. Connect with Tori:Website: https://www.torijenae.comInstagram: https://www.instagram.com/tori.jenae/ Connect with Limor:Website: https://limorbergman.comPodcast: https://limorbergman.com/podcast/LinkedIn: https://www.linkedin.com/in/limorbergman/Substack: https://limorbergman.substack.comCoaching: https://limorbergman.com/coaching/ Search terms: confidence vs competence, how to build confidence as a woman, imposter syndrome women in tech, self-sabotage why it happens, limiting beliefs from childhood, new leader self-doubt, how to stop doubting yourself at work, small t trauma
4 Aug

Men Speak Up at 30%. Women Wait Until 70%. | with Topaz Zafrir

You have been telling yourself you'll put yourself out there once you know a little more. One more course. One more certification. One more round of edits on that post before you press send. Topaz Zafrir has been coaching women through exactly this, and she came on the show with a number that explains a lot: men will speak about a topic as experts when they know about 30% of it. Women wait until they know 70%. That gap is not a knowledge problem. It is the reason opportunities keep going to people who were less prepared than you and said yes faster. In this conversation, we get specific about what playing small actually looks like on a normal Tuesday, and what to do instead. In this episode: • Why does more training never make you feel ready?• What does playing small look like when you're already good at your job?• Why "step out of your comfort zone" is bad advice, and what Topaz says instead• How do you answer the inner critic without arguing with it?• Why being a little imperfect makes people want to work with you About Topaz: Topaz Zafrir is a life and business coach in British Columbia with a master's in organizational consulting and more than 14 years of experience facilitating groups. She went back to school for coaching when she realized the women she was advising didn't need more advice, they needed accountability and someone to believe in them out loud. She helps self-employed women press "send," show up, and talk about their business without freezing, overthinking, or hiding. Connect with Topaz:Website: https://topazcoachingandconsulting.com/LinkedIn: https://www.linkedin.com/in/topaz-zafrir/Instagram: https://www.instagram.com/topaz.coaching.consulting/Facebook: https://www.facebook.com/profile.php?id=61570375918181 Connect with Limor:Website: https://limorbergman.comPodcast: https://limorbergman.com/podcast/LinkedIn: https://www.linkedin.com/in/limorbergman/Substack: https://limorbergman.substack.com Search terms: imposter syndrome at work, confidence gap men vs women, how to stop playing small, why women don't apply for jobs, how to stop hiding in business, saying yes before you're ready, expand your comfort zone, women in tech confidence

From a Woman to a Leader is the women in tech leadership podcast — honest conversations with senior women in tech about promotions, visibility, and leading without burning out.

Creator

Limor Bergman Gross
Years Active

2023 - 2026
Episodes

201
Rating

Clean
Copyright

© Limor Bergman Gross
Show Website

From a Woman to a Leader

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Updated 22 Jun