Kathryn Kolaczek

Mastering the Message: What to Say When Everything’s Wrong

Kathryn is known for creating clarity and control in the moments that matter.

Find the balance between honesty and empathy to build trust when stakes are highest.

Tone, empathy, and truth in high-pressure communication

Prepare leaders to face tough questions and keep your message consistent across channels.

How to brief your spokesperson and manage media

Master the structure of first-response messages that protect credibility under pressure.

The anatomy of an effective holding statement

See real-world crisis responses that shaped reputations—for better or worse.

Real examples of messages that built — or broke — trust

🚀 Learn the 8 critical skills to make you a confident and compelling leader. 

Executive Coach, Prev VP in AI 

LinkedIn

Notion

Netflix

Google

Jess Goldberg - Teaches Leadership @ Columbia

Teaches @ Columbia, Top-Ranked Executive Coach & Prev. VP in AI Robotics

October 2025

December 2025

You want to present your ideas and opinions with unshakable confidence. You want to feel powerful in every room or zoom, but sometimes, when the moment is at hand, you start second-guessing yourself.You want to be both assertive yet kind. But you also don’t want to come across as pushy or a pushover. Maybe you’ve even spent the night counting the opportunities you missed instead of counting sheep. Or worse, you spent the night spiraling about that thing you regret saying.&nbsp;In this course, you'll learn how to step up without stepping on toes, inspire your employees to take meaningful action and captivate your boss with your words so your ideas are heard and valued. Whether you are delivering a presentation, leading a meeting, or having a difficult 1:1 feedback conversation, I’ll give you frameworks for what to say and how to say it so you can drive your team’s success and earn that next promotion or raise!&nbsp;

The Ultimate Leadership Edge

Give feedback that actually results in change

Accelerate your team's productivity

Get buy in for your strategies 

Confidently negotiate 

Command respect from your boss & peers

Level up your confidence and charisma

Experienced leaders looking to improve their skillsQuickly ﻿establish trust, improve productivity and amplify your influence

Startup founders &amp; business ownersBuild a culture that will empower your employees to create their best work

First-time managers (Congrats!) Develop the critical skills that differentiate a follower from a leader

But not everyone thinks the way you do, and you need the skills to be effective with everyone. Being your unfiltered self at work is like showing up in pajamas - comfortable, but not helping your career. Here's the truth: more than two-thirds of us are perceived differently than we intend at work. That gap is likely keeping you from achieving your goals - but you can fix it. In this live, cohort-based learning experience, you'll discover exactly how others perceive the strengths and weaknesses of your communication style. You'll practice concrete tools to help you adapt when needed. You'll leave knowing how to read any room and adjust your approach for maximum impact. Through live sessions, practical exercises, and real-world applications, you'll master the Communciations Comfort Zone framework. This isn't theory - it's a battle tested approach used by top performers to: 🏆 Win trust rapidly by identifying and breaking down communication barriers 💥 Approach challenging conversations with confidence 🤔 Stop wondering where conversations went wrong and learn to recognize the warning signs of misperception in real-time 🤖 Reinforce your learning and get suggestions post-course with our exclusive Communication Comfort Zone AI tool Want to learn more? Let's chat: https://calendly.com/sheilaosullivan/communication-style-course-exploratory-call-20-mins

Your authentic style is perfect - for people exactly like you.

Course syllabus

Please plan to be live and on camera at this time

Two 1.5 hour sessions in one week, with an optional office hour/Q&A

Cohort participants will need to complete a self-rating survey. The assignment must be completed no later than 24 hours prior to the start of the cohort.

Prep work

Course schedule

New managers or managers taking on new teams who want to quickly understand the team, gain its respect and get results quickly.

The experienced executive who wants to coach young managers on leadership communication to help them reach their potential.

The individual contributor who wants to successfully influence others and advance ideas more effectively.

Who this is perfect for:

What you’ll actually learn

<ul><li>Discover exactly how others perceive your communication style</li><li>Identify where your natural tendencies help or hurt you</li><li>Get concrete tools to adapt your approach when needed</li><li>Access ongoing AI powered feedback post-course</li></ul>

See your blind spots clearly

<ul><li>Learn to read communication preferences in real-time</li><li>Spot potential conflicts before they arise</li><li>Adapt your communication to build trust quickly</li><li>Get practical scripts for different scenarios</li></ul>

Map your stakeholders effectively

<ul><li>Handle high-stakes conversations confidently</li><li>Move seamlessly between zones</li><li>Turn potential tension into productive dialogues</li><li>Practice with real-world scenarios in a safe environment</li></ul>

Master cross-zone communication

Being your authentic self at work: is it working for you or against you? It's both. Learn a proven model to persuade and win more often.

Sheila O'Sullivan

Nov 3-5, 2025 12-1:30pm ET

Dec 8-10, 2025 12-1:30pm ET

In this 90-minute workshop, you’ll learn to develop practical storytelling frameworks that turn complex ideas into clear, memorable narratives that win attention, build credibility, and move decisions. We’ll apply these tools to high-stakes moments — executive updates, all-hands meetings, sales or campaign pitches — as well as everyday conversations. This isn’t a writing class or an AI hack (though we’ll cover both) – it’s a masterclass in learning to simplify and align messages, structure stories for engagement, and tailor delivery for different audiences. We’ll cover using AI thoughtfully to draft, iterate, and stress-test content without outsourcing your voice. The result? Stronger influence, tighter cross-functional alignment, and stories that make people lean in. You’ll walk away with enhanced skills to:• Turn presentations and pitches into compelling narratives that capture attention and build trust• Simplify your messages for clarity and team alignment• Use storytelling to reinforce culture, mission, and values Bonus: The same tools work outside of work — for toasts, job interviews, even eulogies. More than anything, you’ll see storytelling as a leadership superpower — and gain the confidence to share stories that make people lean in, trust you, and say three magic words: tell me more.

Strong Storytelling Is a Tool for Influence, Culture, and Impact

If your events are recurring and at the same time, it might be easiest to use a single line item to communicate your course schedule to students

Tuesdays & Thursdays

Feel free to type out dates as your title as a way to communicate information about specific live sessions or other events.

May 7, 2022

Schedule items can also be used to convey commitments outside of specific time slots (like weekly projects or daily office hours).

Weekly projects

Leaders companies who want to nail their value proposition for internal team alignment and external messaging

Founders, comms officers, HR directors, and other leaders navigating transitions such as funding rounds, growth, M&amp;A, hybrid workplaces

Professionals looking to grow in their current role or seek a new role now asking this vital question: How can I be a better storyteller?

Who is this course for...

The ROI on ROS (Return on Story) 

Good leaders build smart strategies, but influence and transformation aren't born from spreadsheets and flowcharts. To win hearts and minds, great leaders get buy in by painting a picture of their vision and taking others along on the ride.

Build Trust and Credibility

Stories are memorable and more motivating than data (the data, ironically, tells us that). Good storytelling helps win client interactions, sales calls, pitch presentations, and job interviews.

Closing Deals

Communicating the story of your "Why?”— the underlying purpose of your personal brand or your company's mission — is vital both for internal alignment and external engagement (it's why Simon Sinek's "Start With Why" TED Talk has 12 million views).

Nailing Your "Why?"

Gain the benefits of storytelling as a meta-skill: it doesn't just make you a better communicator, it elevates how you show up in every part of life.

Amplifying a Lifelong Skill

In 90 minutes, I will make you a better storyteller for the rest of your life.

Dell Technologies

Levi Strauss & Co.

Nuveen

Dropbox

ESPN

Larry Smith

Great Storytelling Is a Tool for Influence, Shaping Culture, and Team Connection at Work —  Let's Harness It.

Cohort 1

Cohort 2

This 4-week course strengthens your professional communication skills through practical tools and proven techniques —whether you're writing emails, leading meetings, or navigating tough conversations. If you’ve been told to speak up more, be more concise, or find yourself dreading on-the-spot questions, this course is for you. You’ll walk away with simple, repeatable frameworks and real-world practice to make these skills second nature. Plus learn the most effective ways that AI can help to refine your communication. Practice is a critical component to improving your communication skills. This course is a risk-free learning environment for you to practice, get feedback, and not be worried what your manager will say or if your flub will impact your performance. Each week, you'll get:• 90 minutes of live instruction (plus replays)• Hands-on practice with real workplace scenarios• Weekly challenges to apply the learning• The most helpful AI prompts and tricks• Optional office hours for personalized feedback You’ll learn practical tools that you can use right away to:• Turn your ideas into clear, structured messages that get results• Feel confident speaking up in meetings (yes, even those unexpected questions!)• Write emails that people actually read and respond to• Speak up and push back with clarity and respect• Influence across teams and levels• Improve your executive presence• Learn the best ways to use AI for communication We will review frameworks and best practices to improve both WHAT you say and HOW you say it. We will apply these concepts to written communication (emails, Slacks, business updates) and verbal (meetings, presentations, ad hoc conversations). *Note: this is not a doc writing course, but you can apply all of the frameworks to your doc! Why this course is different:This course leverages Myra’s Amazon leadership in Marketing, PM, and Learning &amp; Development. She has authored countless docs and trained thousands in effective writing, communication, and influencing without authority at Amazon. Her retail/tech expertise, irreverent humor, and desire to not waste any time create an engaging, impactful learning experience. Grab a spot today or DM her to chat more about the course!

There is a secret sauce to great communication (and it now includes AI)

Live sessions with Myra (recordings available)<ul><li>Week 1: Clear, concise communication foundations</li><li>Week 2: Compelling writing </li><li>Week 3: Confident verbal communication </li><li>Week 4: Prep for challenging scenarios </li></ul>

Fridays - Oct 17, 24, 31, Nov 7

Office Hours &amp; Feedback Sessions with Myra (optional)

Fridays - Oct 24 & 31, Nov 7

Weekly Homework Challenges

Week of Nov 10

Mid to senior level individual contributors or managers (e.g. L5 and L6 at Amazon) who are constantly communicating with stakeholders

Anyone who has received feedback to speak up more, communicate more clearly, and/or gets lots of feedback rounds on their writing

Learners who think in systems, who like frameworks and structure, and are willing to adapt them to make step changes in their communication

It's not for passive learners who are looking for quick tricks or minimal effort to be better communicators

This course is created for

What you’ll get out of this course

These enable you to structure any communication clearly and persuasively and tailor your message to your audience (from execs to peers)

Frameworks to tackle any situation

That will enable you to focus on the things that matter and speak up in meetings and say what you really mean

Feedback, self-awareness, and confidence

Practical ways to adapt these frameworks to real-life scenarios and the most challenging situations

Tips and tricks on real-world situations

Spend less time drafting, editing, and re-working your communications by adopting these frameworks consistently

Time savings

Need help tailoring your communication so it lands better? Get the tools and feedback to communicate confidently and effectively.