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People Business w/ O'Brien McMahon

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May 6, 2025 • 53min

Take Back Your Time w/ the "Time Bandit" Michael Cupps

Michael Cupps is a productivity expert who has been in technology sales and marketing for over thirty years. He learned the importance of productivity from an early age due to his upbringing on a farm in Texas, which taught him the value of hard work, prioritization, and managing time wisely. Michael applies these lessons to his work helping individuals and teams to make the most of their time and priorities. He is also the host of The Habit Architect podcast and founder of the Time Bandit. Michael’s book and mobile app, Time Bandit, is the ultimate guide for those looking to leave behind chaotic and unmanageable to-do lists and ultimately reclaim their time to live a more balanced and productive life.Mentioned on the ShowLearn more about Michael Cupps and his Time Bandit system, including the app, book, and his podcast. Website: https://www.timebandit.io/indexConnect with Michael Cupps on LinkedIn: https://www.linkedin.com/in/michaelcuppsLearn how to make GPT prompts work for you! Jeff Su and his video on making prompts: https://youtu.be/jC4v5AS4RIM?si=3eX0vE3_YvA_bLOs | Jodie Cook shares prompts for small business: https://www.jodiecook.com/chatgpt-prompts-for-entrepreneurs/Tricia Sanders on the People Business podcast: https://peoplebusinesspodcast.com/triciasanders/The Checklist Manifesto book: https://a.co/d/3W40pZBAddiction help at SMART Recovery: https://smartrecovery.org/_______________________Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/Learn more about O’Brien: https://obrienmcmahon.com/________________________Timestamps(00:00) – Welcome to People Business(02:04) – How did you become a time management expert?(04:59) – What commonalities do you see in time management that doesn’t work? (06:59) – The Eisenhower Matrix explained.(12:20) – Leveraging AI for productivity.(17:01) – What advice can you give people on establishing habits? (25:56) – The value of accountability partnerships.(34:49) – How the Eisenhower Matrix works in practice.(38:15) – How can managers and staff have productive conversations about priorities? (43:52) – How can teams adopt effective habits?(46:26) – Breaking addictive habits.(51:17) – Contact Michael Cupps and final thoughts on habit building.
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Apr 22, 2025 • 59min

Breaking Free from the Cage of Ambition, Perfection, and the Need for More w/ Keren Eldad

Keren Eldad is the author of Gilded: Breaking Free from the Cage of Ambition, Perfectionism, and the Relentless Pursuit of More. She specializes in taking high achievers out of the futility of constant pursuit and into their greatest levels of success and fulfillment. Her coaching clients include Olympic athletes, politicians, Hollywood stars, supermodels, Special Forces operatives, and serial entrepreneurs. Keren is a former C-suite executive who has lived and worked in 17 countries and on four continents, and who now coaches leaders all around the globe in four languages: English, Spanish, Hebrew, and French. Mentioned on the ShowKeren’s website: https://kereneldad.com/home/Connect with Keren on LinkedIn: https://www.linkedin.com/in/keren-eldadKeren’s book, Gilded: Breaking Free from the Cage of Ambition, Perfectionism, and the Relentless Pursuit of More: https://a.co/d/2D8JJGeThe Status Game by Will Storr: https://a.co/d/4MgVu2J10x is Easier than 2x by Dan Sullivan: https://a.co/d/7iQ0HivRichistan by Robert Frank: https://a.co/d/745PSeZGood by Jocko Willink: https://youtu.be/IdTMDpizis8?si=Etj6h7iQx2X8BVcFThe Man in the Arena, excerpt from Teddy Roosevelt: https://youtu.be/A311CnTjfos?si=tx-9Jz5zjllcRkcg_______________________Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/Learn more about O’Brien: https://obrienmcmahon.com/________________________Timestamps(2:40) - Meet Keren Eldad.(2:58) - How did you come to do the work that you do today?(9:18) - Why are overachievers reluctant to admit they’re overachievers?(10:38) - What’s the difference between healthy and unhealthy achievement?(16:51) - What does it mean to want to become "nobody"?(18:47) - How do you coach people to let go of status without losing the natural achiever desires?(26:04) - How does a person rein in their ego and stop playing the status game?(33:01) - What is and what isn’t self-acceptance?(38:41) - How do you help people break up with anger?(50:35) - What do people get wrong about happiness?(54:25) - How do we cultivate more of a service mindset?(55:03) - True purpose: Climbing the "second mountain".(57:33) - Final thoughts for overachievers.
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Apr 8, 2025 • 1h 1min

Succession Planning w/ Lilly Lin

Lilly Lin is an Executive Director with Russell Reynolds where she advises clients on broad talent management issues, including succession, leadership development, and assessment. Throughout her career, Lilly has worked with large and small, for-profit and mission-based organizations, establishing herself as a trusted advisor who is highly skilled in preparing clients for their near- and long-term succession needs. She is an active member in the Society for Industrial Organizational Psychology and is often chairing or speaking at SIOP’s annual conference.Mentioned on the Show:Lilly’s profile on the Russell Reynolds website: https://www.russellreynolds.com/en/people/consultant-directory/lilly-linConnect with Lilly on LinkedIn: https://www.linkedin.com/in/lillylin1The Roy Family – a cautionary succession tale: https://www.hbo.com/successionThe New CEO by Ty Wiggins (book): https://a.co/d/7xQj5yn________________________Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/Learn more about O’Brien: https://obrienmcmahon.com/________________________Timestamps(1:30) – Meet Lilly Lin of Russell Reynolds(3:29) – What is succession planning?(5:08) – Does succession planning include planning for leaders below the CEO?(7:53) – Why is changing out the leader so hard for an organization?(11:11) – Is it always a good idea to have a successor ready to take over?(16:42) – Successor talent pools.(17:25) – Where does the succession plan begin?(20:20) – The Board's role in succession planning(23:38) – What are the attributes of a good CEO?(25:57) – Internal vs. External CEO candidates.(27:49) – Are CEO candidates asked if they want to be CEO?(35:33) – What happens to candidates not selected to be CEO?(43:53) – How does a selection committee assess the potential of a candidate for 3-5 years in the future?(47:32) – The NFL: dropping the ball on effective succession planning?(50:01) – How to transition from old guard to new guard.(53:55) – What are the characteristics that make a good leadership transition team?(55:56) – What are some of craziest things you’ve seen in a succession transition?(58:51) – How to contact Lilly. 
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Mar 25, 2025 • 1h 2min

The Seven Tensions of Negotiation w/ Cash Nickerson

Cash Nickerson is chairman of AKKA North America’s Business Unit. He was President, CFO, General Counsel, and the second largest shareholder of PDS Tech prior to its purchase by AKKA Technologies. Prior to that he served as an attorney and marketing executive for Union Pacific Railroad, a partner at Jenner & Block, and chairman and CEO of an internet company. Mr. Nickerson, author of several books including The Seven Tensions of Negotiation, is an avid writer and speaker on the workplace, jobs, and the economy. Mr. Nickerson is the founder and president of the David H. Nickerson Foundation, which supports prostate cancer research.Mentioned on the ShowCash's website: https://cashnickerson.com/Connect with Cash on LinkedIn: https://www.linkedin.com/in/stevencashnickersonThe Seven Tensions of Negotiations by Cash Nickerson: https://a.co/d/h0PnViRGetting to Yes, the negotiation classic by Fisher, Ury, and Patton: https://a.co/d/1veJWUsThe War of Art by Steven Pressfield: https://a.co/d/c7ZyKUI________________________Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/Learn more about O’Brien: https://obrienmcmahon.com/________________________Timestamps(00:00) - Welcome to People Business(1:58) - Introducing Cash(2:18) - What is the difference between Positional and Principled negotiation?(5:20) - What are the Seven Tensions of Negotiation?(6:42) - Is Power the same as leverage?(11:08) - What’s the definition of ‘negotiation’?(12:22) - Is there a type of person who does better with negotiation? What makes a good negotiator?(21:59) - How do we battle scarcity when negotiating?(23:30) - Do you have tips for people to reset their expectations in negotiations?(29:52) - How do you think about Outcome tension?(33:33) - What does prepping a negotiation look like?(41:23) - When is it a good idea to use leverage and when is it not?(45:06) - The role of bluffing in negotiations.(47:20) - Team negotiations: speed and proximity(50:18) - Can you have a direct conversation with one person when negotiating with a team?  (53:18) - How do digital/virtual platforms impact negotiations? (54:36) - Have the other party make the hard decision.
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Mar 11, 2025 • 1h 1min

Up Your Interviews w/ Jordan Burton

Jordan Burton is an executive assessor and interview trainer, working with top VC/PE investors and high-growth startups to hire the best of the best. He has trained over 3,000 executives and investors on hiring and interviewing skills, working with companies like Sequoia Capital, TH Lee, Insight Partners, Twilio, and Scale AI, and over 50 venture-backed startups. He was formerly a Partner at leadership advisory firm ghSMART, a consultant at Bain & Company, and he holds an MBA from Harvard Business School.Mentioned on the ShowConnect with Jordan Burton on LinkedIn: https://www.linkedin.com/in/jordanwburtonLearn more about Talgo Team Building and Training: https://www.talgo.io/Listen to futurist Alexandra Levit on People Business: https://peoplebusinesspodcast.com/alexandralevit/________________________Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/Learn more about O’Brien: https://obrienmcmahon.com/Timestamps(1:44) - Welcoming Jordon(2:17) - How does one become an expert in interviewing?(3:27) - How should you structure different types of interviews?(5:03) - What makes a good candidate? (10:53) - Are there any counterintuitive aspects of the interview process?(16:05) - How and What questions vs. Why questions (24:34) - When it comes to hard skills, how do we create good problem-solving interviews?(27:24) - Is there a similar way to test soft skills?(38:50) - The importance of motivation and will. (32:03) - How do we assess the actual skills required in real-time?(35:14) - What are your thoughts on the statement  "hire for attitude, train for skills"?(42:12) - Tips for candidates and interview teams to get organized and prepare(45:13) - How do we decide the best questions to be asked?(45:07) - How does an individual prepare for an interview?(46:19) - How do you analyze an interview?(49:09) - How do we develop our gut instincts? (52:32) - What is disciplined decision-making? (55:02) - Track, with honesty, which decisions worked out.(58:46) - Can you share a crazy interview story?
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Feb 25, 2025 • 51min

Forecasting the Future of Work w/ Alexandra Levit

Alexandra Levit is a writer, consultant, speaker, workplace expert, and futurist. She has written ten business and workplace books and is currently a nationally syndicated columnist for the Wall Street Journal. In 2019, she was named to "The Thinkers 50 Radar" List.Mentioned on the ShowConnect with Alexandra on LinkedIn: https://www.linkedin.com/in/alexandralevitLearn more about Alexandra and her Inspiration at Work content: https://alexandralevit.com/Alexandra’s books: https://alexandralevit.com/booksReady Player One (book): https://a.co/d/f4dPAST________________________Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/Learn more about O’Brien: https://obrienmcmahon.com/Timestamps(1:48) - Welcoming Alexandra(2:12) - How did you start doing futurist work?(5:08) - What were you doing to self-destruct your career?(7:08) - What were your insights from the Dale Carnegie class?(8:15) - What is your take on the "bring-your-whole-self-to-work" movement?(10:33) - Developing skills in forecasting and strategic foresight.(15:08) - Did you cultivate the ability to see beyond just tomorrow?(16:55) - How do you recommend building the skill of vigilance?(19:29) - Balancing an optimistic view of the future with a pessimistic view of the future.(26:52) - What trends are you seeing people pay too much attention to and why?(30:15) - How do we effectively make sense of new technologies?(34:20) - Are there any other trends people are paying too much attention to?(36:30) - Which trends are not receiving enough attention?(43:37) - How would you encourage people to think about trends for success?(47:03) - Why are you buying property in Vermont?(49:38) - Final thoughts: Don't be scared and see opportunities. 
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Feb 11, 2025 • 49min

Leading a Creative Culture w/ Ashley Elmore of Meow Wolf

Ashley Elmore is the Vice President of Human Resources at Meow Wolf, an arts production company that creates immersive, multimedia experiences that transport audiences of all ages into fantastic realms. In this conversation, she shares lessons learned from building and perpetuating a creative, collaborative culture. Mentioned on the ShowWatch Origin Story, the Meow Wolf Documentary: https://meowwolf.com/about/origin-story (film trailer on YouTube here)The Meow Wolf website: https://meowwolf.com/Ashley Elmore at Meow Wolf: https://credits.meowwolf.com/people/ashley-elmore/Timestamps(1:24) - Welcoming Ashley(1:53) - What is Meow Wolf?(4:21) - What is the culture like at Meow Wolf?(6:03) - How do art and business meet in the organization?(8:51) - What are Meow Wolf's values?(10:02) - What does creative collaboration look like and how do you foster it?(11:37) - Do you have any other examples of what "giving creation space" looks like?(13:20) - Where did the idea for giving downtime for a week come from?(15:54) - What is "provocative playfulness"?(18:43) - How do you navigate the polarity of creativity and profit?(23:03) - How does the organization approach broader social and/or political topics?(27:53) - How does leadership communicate with employees?(30:10) - How often are you talking about your values?(32:12) - How and what do you celebrate?(34:43) - Who’s driving the celebrations?(37:59) - How do you treat and deal with failure?(42:14) - Is there anything else about Meow Wolf that we didn’t talk about that makes it a special organization?(43:18) - Does working in a creative organization bring out the creativity of non-creative employees?(46:52) - What are your personal creative pursuits?
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Jan 28, 2025 • 1h

How to Set (and Stick to) a Strategy w/ Tricia Sanders

Tricia Sanders is the Founder & Lead Strategist at High Five Strategies. She and her team are the people leaders call when they need help connecting the dots between current- and goal-state. Tricia is an expert at challenging long-standing assumptions and drives creative yet pragmatic results. Prior to this work, she was COO at First Bank in St. Louis and an officer in the United States Army with tours in South Korea, Qatar, and Afghanistan.Mentioned on the ShowConnect with Tricia on LinkedIn: https://www.linkedin.com/in/patriciaasandersHigh Five Strategies: https://www.highfivestrategies.com/Brian Emerson discussing polarities on the People Business podcast: https://peoplebusinesspodcast.com/brianemerson/Coach Rachel Hanson on People Business: https://peoplebusinesspodcast.com/rachelhanson/________________________Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/Learn more about O’Brien: https://obrienmcmahon.com/Timestamps(1:50) - Welcoming Tricia(2:08) - What is the work of High Five Strategies?(10:17) - Why is setting strategy so uncomfortable?(15:30) - How do you help clients come up with the right set of goals?(21:20) - How do you pick one goal without letting the others slip?(25:42) - The "Even Over" statements exercise(31:29) - It's good to know the actual culture of a company(36:23) - Why is clarity so important when it comes to goals as well as knowing your "why" and your "what"?(42:03) - Why won’t you take on a client for less than an 18-month engagement?(43:52) - Where are the biggest pitfalls in implementing strategy?(49:41) - How do you help people become open to change?(57:04) - Where can people reach you?(57:42) - Do you have a personal 35 word strategy?
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Jan 14, 2025 • 1h 5min

Talent Scarcity: The Boiling Pot We Are All Swimming In w/ Ben Eubanks

Ben Eubanks is a writer, speaker, and researcher living in Huntsville, Alabama. His work has been featured in numerous industry publications and his books have been cited by some of the world’s most prestigious universities as a method for instructing the next generation of HR professional. Ben spends his days as the Chief Research Officer for Lighthouse Research & Advisory, a firm that examines and delivers groundbreaking insights on the HR technology market as well as workforce trends in hiring, training, retention, and more.Mentioned on the ShowConnect with Ben on LinkedIn: https://www.linkedin.com/in/beneubanks Talent Scarcity: How to Hire and Retain a Shrinking Workforce by Ben Eubanks: https://a.co/d/akBprGPLighthouse Research Advisory: https://lhra.io/Listen to Loran Nordgren’s return interview on People Business: https://peoplebusinesspodcast.com/lorannordgren2/________________________Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/Learn more about O’Brien: https://obrienmcmahon.com/________________________Timestamps(6:10) - Why did you write Talent Scarcity?(10:31) - Can you explain what has been happening with the birth rate in America?(14:59) - What’s the difference between a scarcity and a shortage?(17:56) - How are companies approaching the people/talent scarcity dilemma?(26:04) - Where does the gig economy play into the scarcity discussion?(33:01) - How do you see companies shifting hiring to remain competitive in the coming market?(37:10) - What is the hidden labor market?(48:34) - How do you see organizations embracing this as part of the culture?(51:46) - Leading is reminding/the Forgetting Curve(56:10) - Do you see organizations doing anything different in how they market themselves to attract qualified applicants?(1:00:08) - Final thoughts: AI, the creativity killer? 
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Dec 17, 2024 • 1h 5min

Changing the Stories We Tell Ourselves w/ Rachel Hanson

Rachel Hanson is a Builder with Built to Lead, a band of personal and leadership coaches helping individuals and teams awaken and transform. Prior to joining BTL, Rachel spent 12 years as a Division I Women's Softball head coach at Stanford and Dartmouth. Mentioned on the ShowLearn more about Build to Lead: https://builttolead.com/Rachel’s profile on the Build to Lead site: https://builttolead.com/rachel-hanson/Rachel on LinkedIn: https://www.linkedin.com/in/rachel-hanson-48121817Meru (film): https://www.merufilm.com/Listen to Chet Scott’s interview on People Business: https://peoplebusinesspodcast.com/chetscott/Timestamps(2:14) - Welcoming Rachel.(3:01) - How do you describe Built to Lead and the work you do?(4:43) - How did you get introduced to Built to Lead in the first place?(5:37) - How has your coaching changed since starting? (13:01) - How do we see clearly the stories we are telling ourselves?(14:38) - What does discovery look like with a new client? (16:16) - What are your favorite discovery questions?(17:55) - What does the work in those first practices look like?(19:44) - How can you tell if someone lacks clarity? (23:35) - How do we change our beliefs once we’ve discovered them?(37:23) - Is there anything else we haven’t covered on the concept of changing the stories we tell ourselves?(46:03) - Where do you recommend people start with the writing/journaling?(48:55) - How do you help people who won't be honest with themselves because they are scared it will mean having to make a drastic change?(55:02) - How do you coach your clients when it comes to defining their purpose?(59:50) - What elements of this work have most influenced your life?(1:01:15) - What is a story that you changed about yourself?

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