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625: Melody Wilding - Effectively Managing Up, Designing Your 1:1s, Getting Paid What You're Worth, Creating The 1 Pagers, & Earning The Triple Win

The Learning Leader Show With Ryan Hawk

Release Date: 03/09/2025

668: Brian Kelly (The Points Guy) - Building a Media Empire, Crafting a Big Vision, Relentless Leaders, Hiring Well, Scaling Up, & How To Win at Travel show art 668: Brian Kelly (The Points Guy) - Building a Media Empire, Crafting a Big Vision, Relentless Leaders, Hiring Well, Scaling Up, & How To Win at Travel

The Learning Leader Show With Ryan Hawk

Go to for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Brian Kelly is the founder of The Points Guy, which he built from a side hustle blog into a travel media empire that he sold for $28 million. At 42, he's now an angel investor in 15+ companies, including Bilt (valued at $11 billion). In this conversation, he shares lessons on...

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667: Nick Gray - How to Host World-Class Events, Why Leaders Need a Personal Website, Writing Like You Talk, Mastering Introductions, the Viral Tokyo Trip, & Adding Value Before Taking It show art 667: Nick Gray - How to Host World-Class Events, Why Leaders Need a Personal Website, Writing Like You Talk, Mastering Introductions, the Viral Tokyo Trip, & Adding Value Before Taking It

The Learning Leader Show With Ryan Hawk

Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Nick Gray is the author of The Two-Hour Cocktail Party and founder of Museum Hack. He's mastered the art of hosting events that strengthen networks and build genuine connections. In this conversation, he shares practical systems for hosting gatherings, why every leader needs a personal website, and lessons learned from...

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666: Angie Hicks (Founder of Angie's List) - The Power of Selling Door-to-Door, Executive Presence, Being Told She Was 'Too Nice,' and Her 2-Question Career Filter That Kept Her at One Company for 30 Years show art 666: Angie Hicks (Founder of Angie's List) - The Power of Selling Door-to-Door, Executive Presence, Being Told She Was 'Too Nice,' and Her 2-Question Career Filter That Kept Her at One Company for 30 Years

The Learning Leader Show With Ryan Hawk

Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Angie Hicks, co-founder of Angie’s List (now called Angi). She started the company at just 23, going door-to-door as a self-described introvert and non-salesperson, and turned it into a national platform trusted by millions. During our conversation, we discuss what it takes to lead with authenticity and build lasting...

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665: Pat Lencioni - Five Dysfunctions of a Team, Fear-Based Success, Working Genius, Anticipating Objections, and The Hidden Cost of Proving Yourself show art 665: Pat Lencioni - Five Dysfunctions of a Team, Fear-Based Success, Working Genius, Anticipating Objections, and The Hidden Cost of Proving Yourself

The Learning Leader Show With Ryan Hawk

Go to for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Patrick Lencioni is the founder of The Table Group and a bestselling author of 14 books, including The Five Dysfunctions of a Team and The 6 Types of Working Genius. Behind his achievements (valedictorian, straight A's, business success) were childhood wounds that drove him to prove...

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664: David Adelman - 664: David Adelman - Campus Apartments CEO and 76ers Co-Owner on Losing a Big Bet, Bar Mitzvah Real Estate Deals, His Grandfather's Holocaust Survival Story, and Building Philadelphia's New Arena show art 664: David Adelman - 664: David Adelman - Campus Apartments CEO and 76ers Co-Owner on Losing a Big Bet, Bar Mitzvah Real Estate Deals, His Grandfather's Holocaust Survival Story, and Building Philadelphia's New Arena

The Learning Leader Show With Ryan Hawk

Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: David Adelman is the CEO of Campus Apartments, founder of Darco Capital, and co-owner of the Philadelphia 76ers. During our conversation, we discussed how losing a basketball bet at age 11 changed his life, investing his bar mitzvah money in real estate, becoming CEO at 25, his grandfather's Holocaust survival story, and...

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663: Priya Parker - The Art of Gathering with Purpose: Power, Preparation, Magical Questions, and the Psychology of Bringing People Together show art 663: Priya Parker - The Art of Gathering with Purpose: Power, Preparation, Magical Questions, and the Psychology of Bringing People Together

The Learning Leader Show With Ryan Hawk

Go to for full show notes Join tens of thousands of leaders pursuing excellence: This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: Priya Parker is a master facilitator, conflict resolution expert, and author of the bestselling book The Art of Gathering: How We Meet and Why It Matters. Priya has spent decades facilitating difficult conversations in boardrooms, communities, and conflict zones. In...

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662: Nicholas Thompson - The Atlantic CEO on Growing Up With a 662: Nicholas Thompson - The Atlantic CEO on Growing Up With a "Precariously Insecure" Genius Father, Hiring Leaders with an Edge, How Running Builds Discipline, and Why Moving at an Uncomfortable Pace Built a Million-Subscriber Media Empire

The Learning Leader Show With Ryan Hawk

Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: Nicholas Thompson is the CEO of The Atlantic and former editor-in-chief of WIRED. He's the author of the best-selling book (and one of my favorites of the year), The Running Ground. Nick shares why great leaders must balance being decisive with staying open to being wrong, how to build teams that challenge your thinking...

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661: Suzy Welch - How to Identify Your Core Values, Close the Authenticity Gap, and Live with Purpose show art 661: Suzy Welch - How to Identify Your Core Values, Close the Authenticity Gap, and Live with Purpose

The Learning Leader Show With Ryan Hawk

Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Suzy Welch is known for co-founding the Jack Welch Management Institute and writing bestsellers like 10-10-10: A Life Transforming Idea. Her career includes roles as an editor-in-chief for Harvard Business Review, a crime reporter, and a professor. She teaches at NYU and is the best-selling author of...

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660: James Clear (Live at Ohio University!) - The Four Laws of Behavior Change, Systems vs Goals, Building Better Habits, Mastering the Two-Minute Rule, Having a Great Marriage, & The Plateau of Latent Potential show art 660: James Clear (Live at Ohio University!) - The Four Laws of Behavior Change, Systems vs Goals, Building Better Habits, Mastering the Two-Minute Rule, Having a Great Marriage, & The Plateau of Latent Potential

The Learning Leader Show With Ryan Hawk

Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: James Clear is the author of one of the most influential books of our generation, Atomic Habits. He’s sold over 25 million copies worldwide and has helped millions of people transform their lives through the power of small changes. We brought the podcast to the campus of Ohio University, where we recorded live in front...

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659: Derek Sivers - Not Waiting for Permission, Hell Yeah or No, Leadership Lessons From The Dancing Guy, & Why The Standard Pace is for Chumps show art 659: Derek Sivers - Not Waiting for Permission, Hell Yeah or No, Leadership Lessons From The Dancing Guy, & Why The Standard Pace is for Chumps

The Learning Leader Show With Ryan Hawk

Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Derek Sivers is the founder of CD Baby and author of "Hell Yeah or No" and "Useful Not True." He shared how he graduated from Cal Berkeley in two years instead of four because the "standard pace for chumps" - a lesson that shaped his entire career of institutional skepticism and unconventional thinking. From creating...

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The Learning Leader Show with Ryan Hawk

Notes:

  • “I sensed something was terribly wrong when I dialed into the conference line at 8:00 a.m. and heard an unfamiliar voice. “Hi, Mel ody, I’m Janine. I’m with an external HR firm. Unfortunately, this call is to let you know that your employment has been terminated, effective immediately.”
  • Managing up is not kissing up. Managing up is strategically navigating relationships with those who have more positional power than you, namely your boss. It’s a critical skill set for maneuvering through the complex web of power dynamics, conversations, and unspoken expectations that shape our daily work lives.
  • The triple win – What is something you can do that is good for you, good for your boss, and good for the company? Focus on those issues and solving those problems, and good things will happen for you as you grow your career. Like Carly Fiorina. Run towards the fire. Solving those tough problems will help you, your boss, and your company
  • Meeting with a CEO. Connect what you did with what matters. Adapt your communication to that.
  • Have upward empathy. Put yourself in their shoes. What matters to them? Prior to the meeting, meet with their Chief of Staff. Anticipate objections and answer them before they are asked.
  • Create a one-pager for your boss when they are doing your performance review. Highlight your wins. Remind them. Make it easy on them.
    • Do what Lee Rivas told me to do. Every week, send an email with bullet points for all the things you did to help your boss and the company.
    • For the one pagers - be proactive, start with wins, results and outcomes. it's not self-promoting; it's informing. Identify 1-3 key areas where you need their support. Help them become a trusted advisor or partner.
  • Design your 1:1. Send them the topics to talk about so you can drive those discussions. Make their life easier. They have enough other things to worry about.
  • Feedback can only happen after alignment, styles, ownership, boundaries... They go in order.
  • Define your A B Cs
    • Assumptions, Behaviors, Change you want to see
  • The advancement conversation - Be open, and share what you want to do and how you can get there. My Dustyn Kim example and how I messed it up.
  • The Money conversation - You don't get a raise just because time has passed. It has to be tied to results. Don't talk about the past and what you've done. Talk about what you can do to earn the company more. Don't do the "I deserve this" thing. Bosses hate that.
  • Managing up is not kissing up. Managing up is strategically navigating relationships with those who have more positional power than you, namely your boss. It’s a critical skill set for maneuvering through the complex web of power dynamics, conversations, and unspoken expectations that shape our daily work lives.
  • Everything changes when you understand the art and science of influencing others while keeping your own emotions and insecurities in check.
  •  “Managing up isn’t really about making your boss’s life easier. It’s about taking control of your own work experience.”
  • 10 Key Conversations:
    • The Alignment Conversation How can I get in my boss’s head to understand their needs, motivations, and goals?
    • The Styles Conversation Will I earn more respect from my manager if I get to the point quickly, or should I try swapping stories and building rapport? 
    • The Ownership Conversation How can I solve the problems that make my job frustrating? How can I seize opportunities without stepping on toes?
    • The Boundaries Conversation How do I say no and push back with tact when my manager saddles me with yet another task?
    • The Feedback Conversation How can I respectfully and effectively give my manager feedback in order to improve processes and communication?
    • The Networking Conversation How can I build other allies in the workplace? How can I turn day-to-day interactions into opportunities that open doors?
    • The Visibility Conversation How can I effectively advocate for myself and show off my strengths?
    • The Advancement Conversation What do I need to do to get to the next level? 
    • The Money Conversation When is the right time to negotiate salary? How can I make sure I am getting the compensation I deserve?