Brag Like a Boss

New
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1 Day

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Cohort-based Course

Brag without the cringe: Turn your vague wins into clear, substantial, well-told stories.

I've coached and trained leaders at

Google
Dell
CHANEL
The Walt Disney Company
Caterpillar

Course overview

It's time to shine, not dim your light. Own your work story. Back it up.

“It’s not bragging if you can back it up.” So said Muhammad Ali — the late boxer, social activist, and cultural icon known as The Greatest.


He was right. And yet, too many of us resist bragging when we update our leaders, write our self-appraisals and self-assessments, even introduce ourselves to others. Crown achievements—the gems of our work or career—are buried or left out.


I know why. Often it's feeling unrecognized at work or the culture we emerged from that obstructs. A feeling we're impolite or "showy" or "too work focused" if we speak excitedly about our work. Sound familiar? Then read on.


Brag 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 many global finance companies.

 

Since entering the coaching industry five years ago, I've coached over 1,000 leaders and 8,500+ sessions. I've helped many re-find lost confidence, become briefer, more compelling, and less awkward with sharing their wins. Most go on to get promoted. It's these tactics I bring to this workshop.


It starts with understanding why we dim our light anyway, learning tools and tactics to share the facts, context, and claim the wins in service of you, your team, and the shared work.


We've one, three-hour fast-paced workshop bringing discussion, reflection, tactics, and practice. In this time, we'll:


-Unpack our blockers to bragging like a boss. (It always runs deep--but the mindset's often shared.)


-Write a compelling bio based on facts and narrative insights, no fluff in sight


-Workshop the prompts in your self-assessment/PERF reviews or describe your work for your resume. Write and report on what you did like a journalist, using humility and confidence


-Write an update you can share with your leaders that's so gorgeous, crisp and compelling you'll want to print out and frame it.


-Notice (without judgment) the language we use to dim vs shine our light. Re-cast with active vs passive voice, real vs corporate language, and with concrete facts.


-Add in vital context. Simple adds like the numbers of employees and customers at the company where you serve boosts confidence and heightens awareness, too.


Join the next cohort. Bring your team. You'll change how you write, speak, and think about your work for the rest of your career. You will soar from the insights and tactics gained.

Who is this course for

01

Humble professionals who emerged from a culture of humility where it's considered impolite and/or risky to talk highly of yourself.

02

Driven professionals who lost promotions or opportunities by staying vague, wordy, and choosing humility over confidence.

03

Job seeking professionals who must articulate their value well. Professionals who must showcase the value they and their team bring.

What you’ll get out of this course

Overhaul your bio.

Write your first bio that's substantial, timely, and anchored in well-written facts. Swim away from the sea of sameness.

Make your self-assessment a springboard, not a self-shrinking list

Craft meaningful, well-anchored vignettes (mini stories) about your work for your self-assessment and/or resume. Learn to bottom line, cherry-pick facts, show a range, and offer vital context.

Address and counter our cultural blockers around bragging to capture vs hide from opportunities

Fear of disdain from a dismissive boss. Critical, cautious loved ones. Lost confidence from missed promotions. Awkwardness from childhood messages that praised humility. Blockers on bragging run deep. Pull back the curtain.

Apply brevity and clarity tools to your weekly updates

Transform your updates from forgettable to clear, inspiring, and memorable using journalistic bottom-line-on-top tools, short, crisp lists, and adding a slither about why this matters to you, anyway.

Get peer and instructor feedback

Language choice is nuanced. You'll gain live feedback on how your audience receives your message. Learn where you can brag more, and back it up.

Walk away with a toolkit for communicating your value

You'll think differently about your work forever and learn communication tools that stick, resonate, and open doors while delighting vs frustrating your leaders.

This course includes

1 interactive live session

Lifetime access to course materials

In-depth lessons

Direct access to instructor

Projects to apply learnings

Guided feedback & reflection

Private community of peers

Course certificate upon completion

Maven Satisfaction Guarantee

This course is backed by Maven’s guarantee. You can receive a full refund within 14 days after the course ends, provided you meet the completion criteria in our refund policy.

Course syllabus

Week 1

Jul 2

    Jul

    2

    Live Workshop: Brag Like a Boss

    Wed 7/24:00 PM—7:00 PM (UTC)

What people are saying

        Working with Debbi has been life-changing; she helped me understand and communicate my professional value authentically. Debbi's coaching bridged the gap between my cultural values of humility and the need for confident self-promotion, showing me how to be true to myself while effectively communicating my work.
Stephen Lancaster

Stephen Lancaster

Vocal artist, baritone, Professor of the Practice at University of Notre Dame
        Debbi is one of the best coaches that I have worked with. She has been my coach for the last 2.5 years, and I have learned so much from her. She is caring, wise, and extremely good at listening. I highly recommend her to aspiring leaders and professionals trying to be better communicators.
Ali Khodai

Ali Khodai

VP of AI Product - SandboxAQ

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

Debbi Gardiner McCullough

Debbi Gardiner McCullough

I've coached over 1,000 leaders during highly uncertain, troubling times.

Debbi Gardiner McCullough is a New Zealander who has reinvented herself three times across three continents and industries, most recently leaving academia after 19 years of service to train as an ICF-certified coach.


Debbi’s coaching has helped improve the confidence and careers of over 1,000 leaders (and aspiring leaders) at the world’s largest tech, manufacturing, and financial corporations, including Google, Black Rock, and Dell.


Over 3,000 MBA and journalism students have improved their communications from her mentoring and training. 


Her reporting and writing on social trends and struggles, women leadership, and sustainability has featured in the Economist, the Financial Times of London, Engineering News-Record, the Guardian, and NPR. She's interviewed Fortune 100 leaders, the Property Brothers, Hector Garcia, and the Dalai Lama. She also won a UN Foundation press fellowship for reporting on enterprising ways women save their money when banks won't permit them.


Debbi has a Master’s degree in Journalism from the University of California at Berkeley, where she won the Bloomberg Prize for Excellence in Business Reporting two consecutive years. 


She hosts two podcasts, writes on Medium most weeks, and is publishing several memoirs.


Connect with Debbi on LinkedIn.

A pattern of wavy dots

Join an upcoming cohort

Brag Like a Boss

Cohort 1

$249

Dates

July 2, 2025

Payment Deadline

July 7, 2025
Get reimbursed

Brag Like a Boss Schedule

Three hours. One live workshop.

  • Wednesdays

    11 a.m. to 2 p.m. CST

    One live, highly interactive workshop with robust discussion, coaching, and training. You'll leave with a journalistic, confident-sounding bio, a description for a self-assessment or resume, and a project/work update you'll want to shout out in a meeting or print out and frame.

Free resource

It's not bragging if you can back it up

“It’s not bragging if you can back it up.” So said Muhammad Ali — the late boxer, social activist, and cultural icon known as The Greatest.


My Medium article offers self-coaching tips to help shift your mindset from humility to confidence.


We've also five tips to write a self-appraisal or self-assessment that helps you brag like a boss, back it up, and delight your reader. (Meaning: they enjoy vs endure the read.) 

Enjoy this free resource

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

Brag Like a Boss

Cohort 1

$249

Dates

July 2, 2025

Payment Deadline

July 7, 2025
Get reimbursed

$249

1 Day