Listen Like a Boss. A workshop for leaders wanting to connect more and say less

New
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3 Days

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Cohort-based Course

Gain more trust and credibility by fixing less, locking in, and listening well. My active listening playbook from 9,000 coaching sessions

Companies I coach for

Google
Dell
American Express
BlackRock
Caterpillar

Course overview

Listen Like a Boss: A workshop for leaders wanting to connect more and say less


Many believe we must talk our way to the top. I find active listening helps us get there far more quickly. And yet few of us know how to listen in deep, transformative ways.


When you lock in and listen, those you want to impress and help feel truly heard. Meetings halve in length. Problems become more quickly resolved and decisions smoothly made.


The best part? You feel less drained, less panicked amidst fiascos, and far more informed. You can self regulate (because active listening grounds you) and discover what others really care and worry about, and empower them 10X more.


Listen Like a Boss brings you my proven process, secrets, and habits I've built as a trusted executive communications coach with Google, the US Air Force, Dell, American Express, and major global finance houses and banks.

 

Since entering the coaching industry five years ago, I've coached over 1,000 leaders and 9,000 sessions. By listening, probing, and giving space, I've helped leaders resolve stubborn mindsets and tackle tricky issues. Together, we've created tactics boosting their position and confidence, just from becoming clearer and briefer. I can teach you how. It starts with committing to becoming a better listener and listening how you've never listened before.


We've three, 1.5 hour workshops bringing discussion, reflection, tactics, and practice:


Class 1: Learn how most of us typically listen and discuss our blockers to listening better. (The biggest blockers I've heard? Loneliness, anxiety, and fears of falling back, even unworthiness.) Discover my active listening process, and see me demonstrate it live time, with you.


Class 2: Discover three quick and easy frameworks from master coaches and journalists helping you listen deeply, reveal blockers and hopes, and co-creating action steps. Learn my own frameworks and questions with 1-3 word prompts. In an anchored, spacious conversation, "and?" or "because?" prompt and invite so much. Practice and unpack the learnings together.


Class 3: Practice and unpack the learnings together. Learn my best tips for getting comfortable with the pause. Gain more tips and refresh on questions that help receivers unlock and connect.


AMA: Ask me anything (whatever you want) about active listening and air in a trusted space your blockers.



By the end of this course, you will learn to:


-Frame conversations and meetings in the front end so we can listen better and converse less. Simple prompts like: "Do you want me to listen to listen or to solve?" changes your game—and theirs


-Interrupt in service of others. We struggle to focus when people ramble, bury their bottom line, or ignore the question. Create new ways to ask for the specifics and anchoring you need.


-Experience listening through reduced tech distractions and worries. Anchor with me. Go into thorny situations with a different mindset: To understand, listen, and then to help solve.


-Feel less squirmy about silence. Revisit pause as time for you to self regulate. Pause gifts your receiver time to think, reflect, and self empower


-Sense positive emotional shifts. Feel the potency of this often underestimated and misunderstood craft none of us truly master.


You won't get much from this course if you:


-Expect instantly to change a life-time of distracted, partial, or narcissistic listening habits. This workshop brings an excellent kickstart through self awareness, frameworks and tactics, discussion, and practice.


-Think active listening is flimsy and just for coaches. Come ready to feel challenged. Active listening's intensely powerful—for you, and your receiver.


Join the next cohort. Bring your team. You'll change how you listen and gain ideas and tips to put into action with your very next high-stakes meeting and everyday conversations, even with those you love.

A top coach’s frameworks and tactics to hush up, observe, mirror back, and empower others to figure things out. Build calm through pause.

01

C-Suite Leaders and Managing Directors needing to listen, not instantly solve nor lecture, to help win back client's trust

02

Chatty leaders seeking frameworks to bottom line and listen better, if they want to know what’s on the minds of many.

03

Leaders needing the coach approach to leadership, but who lack the time nor interest to formally certify with the Intl Coaching Federation.

What you’ll get out of this course

Active Listening strategies, tips, and secrets from a communications coach 1000+ global and Fortune 100 leaders adore and trust

  • Few of us trained to listen deeply nor thought we needed to. The world's changed. I built this workshop to share what helps me quickly reveal the fears, hopes, blockers, and brilliance in leaders I coach, so you too can pour in less, quit trying to fix, and win big

Awareness of how we typically listen and how that impacts our relationships, business, and growth

  • Discover listening psychology. Most of us listen with narcissism, selectivity, passiveness, domination, and direction. We listen to share what we know or "to fix."
  • Discuss our blockers, goals, where and why we zone out and all that we miss

Trust that silence is golden and profitable. Master the executive skill of knowing others have insights and answer(s) too

  • Truncate meetings through better listening and framing. Facilitate.
  • Be more curious. Notice patterns and shifts. Find comfort with pause and silence
  • Learn frameworks from coaching gurus, like Stephen Covey, whose simple question: "What's on your mind?" reveals surprising amounts

Brevity training. Learn paraphrasing, bottom lining, picking up and braiding in the speaker's language into powerful, open-ended questions

  • Build clarity through mirroring back and synthesizing the complex like a global reporter
  • See how weaponizing, judgmental, or directive questions shut down and reflective inquiry opens things up
  • Drive outcomes through questions vs quick answers

Seismic shifts in how you feel about yourself as a communicator, a problem solver, and a leader


  • Practice best practices. Get comfy with pausing, silence, curiosity, and noticing shifts, even asking after a sigh
  • Feel less drained from pouring in and more confident from learning more about your audience

A movement. Build your own EQ through Active Listening and your organization will follow

  • Discover a new personal brand as your listening improves
  • Become a life-long learner of an extraordinary craft which uplifts, empowers, and connects us

What’s included

D G McCullough

Live sessions

Learn directly from D G McCullough in a real-time, interactive format.

Lifetime access

Go back to course content and recordings whenever you need to.

Community of peers

Stay accountable and share insights with like-minded professionals.

Certificate of completion

Share your new skills with your employer or on LinkedIn.

AMA

A live Q&A where you can hit me with whatever questions and worries you have about deep, focused listening

Maven Guarantee

This course is backed by the Maven Guarantee. Students are eligible for a full refund up until the halfway point of the course.

Course syllabus

Week 1

Oct 7—Oct 9

    Oct

    7

    LIVE EVENT: Class One. Listen Like a Boss

    Tue 10/74:00 PM—5:30 PM (UTC)

    Oct

    8

    LIVE EVENT: Class Two. Listen Like a Boss

    Wed 10/84:00 PM—5:30 PM (UTC)

    Oct

    9

    LIVE Event: Class Three. Listen Like a Boss

    Thu 10/94:00 PM—5:30 PM (UTC)

    Oct

    9

    LIVE Event: AMA. Ask me anything on active listening

    Thu 10/96:00 PM—6:45 PM (UTC)

What people are saying

        Debbi‘s a pro listener. She asks thought-provoking questions, gets everyone engaged, and shares valuable lessons from coaching top industry leaders. I know because she’s my coach, trainer, and now co-facilitator for my own Sales Rocket Fuel course here on Maven. Check out “Listen Like a Boss” to sharpen your listening and facilitating skills. 
Chris Bogdan

Chris Bogdan

CEO & Founder, Sales Rocket Fuel
         Coaching with Debbi has been a game changer in my communications. Great communication requires great listening. And Debbi is an exceptional, attentive listener. Our conversations bring meaningful breakthroughs, clarity to tough situations, confident decisions, and refined expressions. Take her workshop to listen with empathy and precision.
Fernanda Noronha

Fernanda Noronha

Director of Finance at Grainger
         A coaching session with Debbi is truly transformative! The questions she asks help me think of things I've never considered and in ways that enlighten, help me understand, and explore. She is a master in coaching to your strengths while helping you discover the best listener you can be! Get ready to dive deep, uncover opportunities, and grow. 
Laura E. Jackson

Laura E. Jackson

Assistant Manager, Learning and Development
        Debbi is one of the best coaches I've worked with, now for 2.5 years. I've learned so much from her. She is caring, wise, extremely good at listening, and turns challenges to a positive learning or opportunity. I highly recommend her, especially if you're an aspiring leader wanting to become better at listening and communicating.
Ali

Ali

Group Product Manager at Google DeepMind

Leaders at the world's largest global corporations and military agencies trust me as their communications coach

D G McCullough

D G McCullough

Communications coach of 1k+ Fortune 500 leaders. Memoirist. Entrepreneur

I'm a New Zealander who has reinvented three times across three continents and industries, most recently leaving academia after 19 years of service to train as an ICF-certified coach.


I did not expect what happened next. I've coached over 1,000 leaders at the world’s largest tech, manufacturing, and financial corporations to listen better, communicate better, and tell beautiful stories about their lives and work. With that, many go on to higher promotions and bigger titles internally, externally, or feel inspired to launch their own venture.


I segued to coaching from academia and global business journalism where I reported on social trends and struggles, women leadership, and sustainability for the Economist, FT of London, Guardian, NPR, Engineering News-Record, and Wired.


I've had the pleasure of interviewing Fortune 100 leaders, the Property Brothers, Hector Garcia, and the Dalai Lama. It's these reporting, storytelling, and listening skills I bring to my communications workshops and cohorts on Maven.


I have a Master’s degree in Journalism from the University of California at Berkeley and am a first generation college graduate, which feels pretty amazing given I grew up in the wilderness of New Zealand and Asia. My oldest son took his moonshot to study at Harvard University and lassoed it in.


To keep my journalism skills fresh, I host two podcasts, write on Medium, and am publishing several memoirs and communications guides for the joy, and to democratize the life-changing effects of communications coaching.


Connect with Debbi on LinkedIn.

Leaders at these orgs hire me to coach

Google
Boston Consulting Group (BCG)
Accenture
BlackRock
Meta

Career highlights

  • Coached 9,000 coaching sessions with devoted, returning clients across the globe. Most clients are foreign-born, like me.

  • Served as a translator at Yamanouchi Pharmaceutical in Tokyo, Japan at age 25. Learned from this Japan chapter to pause and listen well.

  • Won a UN Foundation press fellowship for reporting on alternative ways women entrepreneurs save their money when banks won't permit them.

  • Taught 1,500 journalism and MBA students. Former lecturer of business communication and journalism at UNC Chapel Hill.

  • Certified with Positive Intelligence, as the 81st certified mental fitness coach globally. ICF-certified with MCC certification underway.

A pattern of wavy dots

Join an upcoming cohort

Listen Like a Boss. A workshop for leaders wanting to connect more and say less

Cohort 1

$899

Dates

Oct 7—9, 2025

Application Deadline

Sep 24, 2025

Listen Like a Boss Workshop Schedule

Two 2-hour workshops. 15 Minutes Prep.

  • Tuesdays

    11:00 a.m. to 1 p.m. CST

    With small prep work (15 minutes) and 2 hours live discussion, training, demonstration, and practice, you’ll have a handful of tips on how to Listen Like a Boss by lunchtime.

  • Wednesdays

    11:00 a.m. - 1:00 p.m. CST

    With small prep work (15 minutes) and 2 hours live discussion, training, demonstration, and practice, you’ll learn beautiful frameworks to Listen Like a Boss by lunch time CST.

Learning is better with cohorts

Learning is better with cohorts

Active hands-on learning

This course builds on live workshops and hands-on projects

Interactive and project-based

You’ll be interacting with other learners through breakout rooms and project teams

Learn with a cohort of peers

Join a community of like-minded people who want to learn and grow alongside you

Frequently Asked Questions

A pattern of wavy dots

Join an upcoming cohort

Listen Like a Boss. A workshop for leaders wanting to connect more and say less

Cohort 1

$899

Dates

Oct 7—9, 2025

Application Deadline

Sep 24, 2025

$899

3 Days