The Stacking Benjamins Show

Episode SB1763 — "How to Actually Listen (Not Just Wait to Talk)"

Date: November 19, 2025
Host(s): Joe Saul-Sehy, OG
Featured Guest: Katie O’Malley, Executive Coach

Episode Overview

This episode dives into the art and power of intentional listening—how it can transform relationships at work, home, and even around the holiday dinner table. Executive coach and TEDx speaker Katie O’Malley joins Joe and OG to break down her "AIR" method of listening, offering strategies to foster connection, deepen understanding, and improve professional as well as personal outcomes. The hosts also debate the latest investing thesis: should you really just own stocks 100% of the time, as recent research suggests? The episode balances practical communication advice, career and money insights, and the usual Stacking Benjamins banter.

Key Discussion Points & Insights

1. The Importance of Listening: Lessons from Katie’s Childhood

• Katie’s Foundational Story
  • [14:24] Katie recounts a formative incident where her mother grounded her for dominating a childhood phone call without giving her friend a chance to talk or asking about her day.
  • Quote:

    "You got off the phone without even asking her a single question about her day or even pausing... That’s simply not how we treat people in this house. So you’re grounded for two weeks."
    — Katie O’Malley, quoting her mother [16:24]

  • Katie’s mother’s lesson: True communication is a two-way street. This experience shapes Katie’s lifelong focus on being a better listener.

2. Why Listening Matters (Especially at Work)

• If you’re not listening, you lose:
  • The opportunity to connect at a deeper level
  • Trust-building potential
  • True understanding, not just hearing words
• Quote:

  “Communication did not happen if the message wasn’t received and if the other person couldn’t hear it, couldn’t listen to it.”
  — Katie O’Malley [18:07]

• Connection does not mean agreement: You can genuinely connect with someone even if you disagree, provided you model curiosity and acceptance of differing perspectives.

3. Money & Listening: The Financial Benefits

• Ability to listen can:
  • Lead to better workplace navigation (handling bosses, negotiating raises or deals)
  • Help maintain strong personal and professional networks (critical since 86% of jobs are landed via networking)
  • Reduce the “cognitive bandwidth tax” of financial stress (as referenced in the earlier Karen Holland snippet [05:25])

4. Katie O’Malley’s AIR Formula for Listening

A = Attention

• Attend both to the person you’re with and to yourself (your own internal responses—heart pounding, sweating, etc.)
• Somatic inquiry: Notice physical cues that signal you’re getting reactive.

I = Intention

• Keep your intention simple: Your ONLY goal is to understand the other person, not to form your reply.
• Quote:

  “Your only intention when you are listening to somebody else is to do your very best to understand what they’re saying.” — Katie O’Malley [28:20]

R = Recognition

• Show the other person that you “get” why the issue matters to them, even (and especially) when you don’t agree.
• Recognition is NOT praise—it’s about dignifying someone’s experience or emotion.
• Example: Instead of immediately giving bad news or disagreeing, pause to verbalize the importance of the issue for the other person.

AIR in Action

• [43:38] Example response formula: Paraphrase what you heard, state a physical/emotional observation, reflect/confirm feeling.

  • "Joe, when you were telling me about the contractors in your house, it sounds like there’s a lot going on...That must be causing you some stress..."
    — Katie O’Malley [43:04]

5. Overcoming Internal Barriers & Bias

• Recognize your own triggers, judgments, and assumptions (e.g., Katie’s unconscious bias against southern accents [38:04]).
• Courage means being honest about when you’re too reactive to continue a productive conversation (“I’m having a pretty strong reaction. Can we come back to this?”) [34:02]

6. Practical Application: At Work and Home

• Work Benefits:

  • Improves employee retention and satisfaction
  • Fosters belonging and connection—people don’t readily leave communities where they feel heard
  • Boosts productivity and clarity, ultimately impacting the bottom line
  • Quote:

    “When we listen in this way...it leads to greater understanding, connection, and trust. Those three things lead to sense of belonging...and people do not readily leave their community.”
    — Katie O’Malley [46:28]

• Holiday Scenario:

  • When faced with a difficult relative (e.g., an uncle obsessed with crypto), use recognition to shift from debate to understanding motivation:

    • “Hey, Uncle Larry, I’m pretty sure we disagree when it comes to crypto. And it’s also apparent to me this is something you really believe in...I want to better understand where that passion is coming from.”
      — Katie O’Malley [49:02]

Notable Quotes & Memorable Moments

• On the AIR Formula and Self-Awareness:

  “Everything is a feeling before it’s a thought. Everything is a thought before it’s a behavior. But it’s so difficult to catch the feeling and the thought.”
  — Katie O’Malley [27:01]

• On Modeling Courage and Self-Correction:

  “There’s courage in the recognition piece...We have to be willing to understand what’s getting in the way of us being able to really understand them—our judgments, assumptions, unconscious biases."
  — Katie O’Malley [35:42]

• On the Impact of Listening:

  “Listening is a deposit into the bank of goodwill that you will one day get to make a withdrawal from.”
  — Katie O’Malley [24:35]

• Joe Personally Reflects:

  “Megan, I don’t mean to out you, but...she has practiced this. Katie, like it is a technique and she’s really practiced it. And we spend most of the time talking about me. And I like her so much because we talk about me.”
  — Joe [25:34]

Detailed Timestamps for Major Segments

• Intro, Banter & Karen Holland’s Financial Literacy Project: [02:00–07:00]
• Katie O’Malley Interview Begins: [11:22]
• Grace Hopper Conference reflections: [11:27–13:31]
• Katie’s childhood grounding story: [14:24]
• Why listening matters at work & in life: [17:44]
• Connection ≠ agreement: [20:22]
• AIR Formula explained: [25:48–30:29]
• Application & self-awareness/somatic inquiry: [27:01]
• Handling internal reactions, courage: [34:02–35:42]
• Personal stories about bias, recognition: [37:08–40:26]
• Practical steps for paraphrasing, observing, reflecting: [43:04–44:35]
• Benefits at work & for retention/productivity: [46:28–48:27]
• Handling holiday dinner debates: [49:02]
• TEDx experience and final thoughts: [50:59]

Investing Headline: Should You Own Stocks for the Long Run?

[56:06]

• Headline Segment Overview

  • Wall Street Journal’s Jason Zweig examines new research advocating an all-stock portfolio—even in retirement—but cautions about risk and volatility.
  • Key finding: Historically, bonds are weak diversifiers over very long periods; stocks offer higher returns but require ironclad patience.
  • Quote:

    “TINA feels friendly right now as stocks flirt with record highs…but over a lifetime, investing as if there’s no alternative to stocks will demand that you have the patience of a tortoise and the emotions of a stone.”
    — Jason Zweig read by Joe [69:21]

• OG’s Take:

  • Stocks are the “right way to invest” over long time periods, but the real challenge is behavioral—can you handle the wild ride, especially when losses are large in real dollar terms as you age?

• Practical Advice:

  • Hold two to three years’ worth of cash or safe assets to weather downturns in retirement.
  • All-stocks is for those who can stomach it; it’s okay to leave some “on the table” emotionally for better peace of mind.

Final Takeaways

• From Katie O’Malley: Intentional, courageous, and practiced listening—using the AIR formula—can transform not just your relationships at home but your long-term financial and professional outcomes.
• From Joe & OG: Stocks are the historical winner—but only build your plan on risks you can personally stomach, not what looks best on paper.

Relevant Links

• Katie O’Malley’s TEDx Talk (as referenced in show)
• EncourageCoaching.org
• Jason Zweig’s Wall Street Journal column (subscription required)
• StackingBenjamins.com/stackinghope (financial literacy challenge)

Summary for Listeners

This episode provides actionable tools and a fresh mindset for anyone wanting less conflict, more connection, and stronger outcomes—at work, with family, and in investing. Katie O’Malley’s simple but powerful AIR formula makes better listening tangible for all, while Joe and OG’s investment discussion reminds us that emotional endurance and clear-eyed self-awareness are just as critical for wealth as they are for relationships. Whether you want to hold your own at the holiday table or stack more Benjamins in 2026, this is a toolkit episode worth revisiting.