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Oscar Trimboli, renowned listening expert and author, returns with transformative insights from his unique journey of coding listening behaviors into software. Inspired by personal experiences with his father's stroke recovery and extensive research within organizational teams, Oscar reveals how technology and conscious facilitation can dramatically improve listening dynamics, reduce meeting time, and foster authentic participation.
In this episode of the listening SUPERPOWER podcast with host Raquel Ark and discover how simple shifts—like asking shorter, clarifying questions and enabling everyone's voice to be heard—can overhaul team communication and unlock untapped commercial and human potential. Learn why "the hardest listening role is the speaker," how pre-meeting listening can boost confidence, and how vivid metaphors can make your message unforgettable.
Whether you lead meetings, manage teams, or want to deepen your listening practice, Oscar provides practical tools and data-driven strategies to elevate your communication for lasting impact.
On taking action: "The difference between hearing and listening is action." -- Oscar Trimboli
SUPERPOWER Notes:
02:00 — Stroke recovery communication breakthrough—Oscar's father's stroke taught him "you can communicate very effectively with somebody who can't speak" using hand squeezes and positioning techniques that forced medical staff to engage the patient directly
04:42 — Taking responsibility through direct engagement: Moving close to his father's face so medical professionals had to "look at him when they ask a question" helped his father "take responsibility for his recovery"
08:30 – From Microsoft vision to reality: Fifteen years after his boss said "if you could code how you listen, you could change the world," Oscar now uses AI to analyze meeting dynamics and participation patterns
12:15 –The 80% share of voice problem: Data revealed few participants dominated 80% of speaking time until a different facilitator in week six dramatically increased participation and meeting effectiveness
18:20 – Halving meeting time through inclusion: Better facilitation that included everyone reduced meetings from "90 minutes weekly" to "45 minutes fortnightly" because "people feel heard and get buy-in"
22:45 – Eight words or less rule: Questions of "eight words or less had higher impact" and create "collective understanding" rather than individual comprehension
25:30 –The three-question test: Before asking: "write it down, count words, then ask: is this for me, them, or the group?" Group questions have highest impact
28:15 – Clarifying questions transform meetings:Only "one or two participants" ask clarifying questions consistently, but their presence helps "questions get better and meetings get shorter"
35:45 – Listen before the meeting: Contact executive assistants beforehand to understand question patterns and presentation preferences for high-stakes meetings
42:20 – Metaphors beat numbers:Use compelling metaphors like "budget as jazz band" because "they remember the metaphor before the numbers"
50:30 – The quiet CFO's transformation: A shy CFO's single word "snake" (about shedding old systems) helped transform company growth from 32% to 170% when leadership finally listened
Key Takeaways:
On the universal listening gap: "We are not good listeners just because we need to be." -- Oscar Trimboli
On the speaker's challenge: "The hardest listening role is the person currently speaking." -- Oscar Trimboli
On meeting effectiveness: "If you want fewer meetings and shorter ones, when you do have them, focus on inclusive facilitation that ensures everyone is heard." -- Oscar Trimboli
On organizational potential: "My question to you listening is who are you ignoring in your organization that is holding you back from massive untapped potential commercially and human potential as well?" -- Oscar Trimboli
On taking action: "The difference between hearing and listening is action." -- Oscar Trimboli
Notes/Mentions:Listening Quiz: listeningquiz.com - Discover what gets in your way of listening effectively (35,000+ people have taken it)
Tools mentioned:
TalkTime and EqualTime (meeting analytics add-ons)
Google Meets, Zoom, Microsoft Teams listening add-ons
Equal Time (Munich-based company for gender and participation analytics)
Books referenced:
"What Doctors Say and What Patients Hear" by Dr. Danielle Offrey
Oscar's third book on listening (influenced by his father's stroke experience)
Listening measurement tools: Talk-to-listen ratios, question analysis, clarifying question tracking, curiosity index
Connect with Oscar Trimboli
www.oscartrimboli.com
Deep Listening: Impact Beyond Words
Connect with Raquel Ark:
www.listeningalchemy.com
Mobile: + 491732340722
Substack listening ALCHEMY newsletter
Podcast email: [email protected]
By Raquel Ark5
77 ratings
Oscar Trimboli, renowned listening expert and author, returns with transformative insights from his unique journey of coding listening behaviors into software. Inspired by personal experiences with his father's stroke recovery and extensive research within organizational teams, Oscar reveals how technology and conscious facilitation can dramatically improve listening dynamics, reduce meeting time, and foster authentic participation.
In this episode of the listening SUPERPOWER podcast with host Raquel Ark and discover how simple shifts—like asking shorter, clarifying questions and enabling everyone's voice to be heard—can overhaul team communication and unlock untapped commercial and human potential. Learn why "the hardest listening role is the speaker," how pre-meeting listening can boost confidence, and how vivid metaphors can make your message unforgettable.
Whether you lead meetings, manage teams, or want to deepen your listening practice, Oscar provides practical tools and data-driven strategies to elevate your communication for lasting impact.
On taking action: "The difference between hearing and listening is action." -- Oscar Trimboli
SUPERPOWER Notes:
02:00 — Stroke recovery communication breakthrough—Oscar's father's stroke taught him "you can communicate very effectively with somebody who can't speak" using hand squeezes and positioning techniques that forced medical staff to engage the patient directly
04:42 — Taking responsibility through direct engagement: Moving close to his father's face so medical professionals had to "look at him when they ask a question" helped his father "take responsibility for his recovery"
08:30 – From Microsoft vision to reality: Fifteen years after his boss said "if you could code how you listen, you could change the world," Oscar now uses AI to analyze meeting dynamics and participation patterns
12:15 –The 80% share of voice problem: Data revealed few participants dominated 80% of speaking time until a different facilitator in week six dramatically increased participation and meeting effectiveness
18:20 – Halving meeting time through inclusion: Better facilitation that included everyone reduced meetings from "90 minutes weekly" to "45 minutes fortnightly" because "people feel heard and get buy-in"
22:45 – Eight words or less rule: Questions of "eight words or less had higher impact" and create "collective understanding" rather than individual comprehension
25:30 –The three-question test: Before asking: "write it down, count words, then ask: is this for me, them, or the group?" Group questions have highest impact
28:15 – Clarifying questions transform meetings:Only "one or two participants" ask clarifying questions consistently, but their presence helps "questions get better and meetings get shorter"
35:45 – Listen before the meeting: Contact executive assistants beforehand to understand question patterns and presentation preferences for high-stakes meetings
42:20 – Metaphors beat numbers:Use compelling metaphors like "budget as jazz band" because "they remember the metaphor before the numbers"
50:30 – The quiet CFO's transformation: A shy CFO's single word "snake" (about shedding old systems) helped transform company growth from 32% to 170% when leadership finally listened
Key Takeaways:
On the universal listening gap: "We are not good listeners just because we need to be." -- Oscar Trimboli
On the speaker's challenge: "The hardest listening role is the person currently speaking." -- Oscar Trimboli
On meeting effectiveness: "If you want fewer meetings and shorter ones, when you do have them, focus on inclusive facilitation that ensures everyone is heard." -- Oscar Trimboli
On organizational potential: "My question to you listening is who are you ignoring in your organization that is holding you back from massive untapped potential commercially and human potential as well?" -- Oscar Trimboli
On taking action: "The difference between hearing and listening is action." -- Oscar Trimboli
Notes/Mentions:Listening Quiz: listeningquiz.com - Discover what gets in your way of listening effectively (35,000+ people have taken it)
Tools mentioned:
TalkTime and EqualTime (meeting analytics add-ons)
Google Meets, Zoom, Microsoft Teams listening add-ons
Equal Time (Munich-based company for gender and participation analytics)
Books referenced:
"What Doctors Say and What Patients Hear" by Dr. Danielle Offrey
Oscar's third book on listening (influenced by his father's stroke experience)
Listening measurement tools: Talk-to-listen ratios, question analysis, clarifying question tracking, curiosity index
Connect with Oscar Trimboli
www.oscartrimboli.com
Deep Listening: Impact Beyond Words
Connect with Raquel Ark:
www.listeningalchemy.com
Mobile: + 491732340722
Substack listening ALCHEMY newsletter
Podcast email: [email protected]

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