Founder, Tech for Product

Colin Matthews

Founder of Tech for Product, Fractional PM leader

How to communicate high-stakes decisions

Amazon

Google

Dell

Walmart

Etsy

PM @ Datavant, MicroSaas Founder, 8000+ Students

Follow a battle-tested method for building buy in and communicating high stakes decisions

Craft a decision doc that streamlines communication

Prepare clear and concise communications for executive review

Improve communication with senior stakeholders

Hone your judgement by taking a structured approach to problem solving

Build your decision making & influence skills

You’ll learn practical tools, frameworks, and hacks that you can use right away to:

Founder of Leadership Lab, ex-Amazon

Leadership Lab

The Wharton School

Myra Deshmukh

Ex-Amazon Leader, Communication Coach, and Highly-Rated Facilitator

May 2026 Cohort

Sept 2026 Cohort

If you’ve ever been told to “get to the point,” felt your ideas were strong but your delivery wasn’t landing, or dreaded being put on the spot in meetings—this course is for you.In 4 weeks, you’ll build a repeatable executive communication skillset: organize your thinking, write and speak with intention, and deliver confident messages that stick—whether you’re sending an email, presenting to leadership, or answering a tough question in real time. You’ll also learn how to use AI to sharpen your message without losing your voice or critical thinking.Participants consistently say they’re using these tools immediately at work and have improved confidence, clearer feedback from peers and managers, and better responses in meetings. Scroll down for verbatims!Over four weeks, we’ll focus on both what you say and how you say it, then practice until it becomes second nature.Each week includes:<ul><li>90 minutes of live training + learning labs for personalized feedback</li><li>Real workplace scenarios and low-risk practice that doesn't impact your work performance</li><li>Weekly challenges to build the habit</li><li>AI prompts you’ll actually use</li><li>1:1 coaching</li></ul>

Executive communication, without the overthinking.

Turn your ideas into clear, structured messages that land

Feel confident speaking up in meetings (yes, even those unexpected questions!)

Manage stakeholders and leaders more effectively

Push back, disagree, and give feedback with clarity and respect

Build credibility and visibility, earn trust faster

Learn the best ways to use AI for communication

Mid to senior level individual contributors or managers (5-15 years of experience) who are communicating with stakeholders &amp; leaders

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

Technical roles (software engineers, PMs, data analysts) looking to better represent their work and earn trust with stakeholders

You will learn how to make and recommend strategic decisions grounded in business reality -  not feature logic.

ex-Product Exec @Spryker, Commerce, eBay

Spryker Systems

BigCommerce

eBay Inc.

PayPal

Elena Leonova

Founder & CPO, OneRank.io,  ex-CPO @ Spryker, VP of Product @ BigCommerce

Cohort 2

Cohort 3

At senior levels, product leadership stops being about having the best answers. It becomes about being trusted with decisions. You’re expected to connect product bets to revenue, cost, and risk — and defend those decisions under pressure.But most product leaders were never taught how those decisions are actually made.So decisions move forward without you. Not because you lack context. But because others are framing the business problem more clearly. They connect strategy to financial reality, risk, and trade-offs. And their judgment lands.This course exists to change that. This is a 6-week, high-touch cohort where your judgment is tested the way it's tested in leadership rooms.You will practice making strategic decisions through real scenarios:• diagnosing business pressure • translating KPIs into strategic bets • navigating financial tradeoffs • defending strategic decisionsYou won’t just learn frameworks. You will apply them live and receive direct feedback on whether your reasoning holds up.It’s judgment that holds when the stakes are real — and the room is deciding whether to trust you. If you want to move from executing strategy to shaping it, this is where that shift happens

Think like a VP before you become one. Ground Product Strategy in business.

Understand the business before building the strategy

Use financial metrics to guide strategic decisions

Build a credible, business-backed product strategy

Present strategy to executives and boards

Partner effectively with Sales, Marketing & Customer Success

Lead with strategic judgment & influence without authority

You already operate as a Senior or Principal PM or Product Lead. You don’t need help shipping, running discovery, or managing teams

Strong Product Execution Fundamentals

You’re used to making calls with partial information, competing metrics, and real tradeoffs. You understand the importance of judgment

Comfort Making Decisions with Imperfect Data

Your judgment is - or soon will be - evaluated by executives, boards, or clients. You’re responsible for explaining why a decision is right

Accountability for Strategic Decisions

Senior &amp; Principal PMs who already deliver at a high level and want to be trusted with larger, riskier decisions - not just execution

Group PMs, Directors, and above who own strategy, make real tradeoffs, and defend decisions under executive scrutiny

Product consultants, coaches, and advisors who want to bring executive-level judgment to their client work and recommendations

Make high-stakes product calls with clarity to earn a bigger scope and influence

Product & Design Leader at Owtcome

Owtcome

Krasi Bozhinkova

Product & Design Leader, turning product success into repeatable growth

July 2026

The gap between mid-level and senior is not knowledge. It is judgment. The ability to make the call earlier, with less certainty, and explain why it matters in terms the business cares about.You may already have strong instincts, but instincts alone don’t earn trust. What gets your work second-guessed is not always that someone else is right. It is that they can connect the decision to adoption, retention, revenue, or strategic advantage more clearly than you can.This course is about closing that judgment gap. You will learn how to identify the real decision inside a messy debate, name the trade-off others avoid, and defend your logic before perfect data arrives. It blends product, design, and business thinking because role boundaries are disappearing and the expectation to make an impact has never been higher.The goal is to become the person leadership brings in earlier, trusts with harder problems, and gives a bigger scope.

Make high-stakes product decisions with clearer logic, stronger conviction, and language that leadership can trust.

Frame the real decision behind a messy debate

Build for critical user needs without waiting for perfect data

Know when to improve, pivot, or rethink your roadmap

Connect every product and design decision to a growth loop

PMs, designers, and cross-functional leaders with 3-5 years of experience, working through ambiguity, trade-offs, and business outcomes.

Level of experience

Bring one live product, feature, or strategic decision to apply the course directly to your own context.

What to prepare

This course is designed for practitioners who want to make better product decisions in AI-shaped markets, not to teach a specific AI tool.

No technical AI background required

Mid to Senior level PMs stuck in execution mode who want to become the senior person leadership trusts to make the harder decisions

Designers who are strategic but can't articulate it and lose the argument when they don’t connect the decision to business impact.

Developers stepping up to own a product area, who need a repeatable way to make hard decisions with incomplete information.

Strengthen inner confidence, inspire others, and sharpen leadership skills through hands-on exercises and real-world tools

Leadership Coach 

Ha Tran

Founder, Ex-Google, Chief of Staff, U.S Department of State Professional fellow

Cohort 1

In high-stakes moments, three things show up at once: 1. what you know is true2. what it might cost3. what you think you should do Most people try to resolve this by thinking harder or speaking better.It does not work. Because the problem is not clarity. The problem is authority. When no one is clearly leading, you: - hesitate even when you know the answer- over-explain to justify your position- say something, then walk it back- leave conversations feeling misaligned This is not a confidence issue. It is a governance issue. What changes after this workshop- You speak without over-explaining or softening your position- You make decisions faster without needing full certainty- You stop negotiating against yourself in real time- You handle pushback without collapsing or escalating- You stay aligned with your decision after the conversation ends This workshop is for you if: - You know what you want to say, but change it in the moment- You make decisions, then second-guess them after- You feel tension between what is true and what is acceptable- You are seen as capable, but do not feel fully in control under pressureMaximum 20 people/workshop to keep it intimate and practical.

You are not confused. You are running multiple leaders.

Make decisions under pressure without internal conflict

Senior leaders and managers looking to lead with conviction and assurance.

High-performing professionals who want to build stronger, more confident leadership skills.

Emerging leaders who seek to develop self-assurance, overcome self-doubt, and project confidence in high-stakes situations.

Agentic AI

Coding with AI

AI Workflows

Claude Code

OpenClaw

Vibe Coding

AI Evals

AI Transformation

RAG & Search

AI for PMs

AI for Engineers

AI for Designers

AI for Marketers

AI for Founders

Product Sense

Product Discovery

User Research

Prototyping

Growth

Analytics

Tech Foundations

Strategy

Influence

Leadership

Career Growth

Machine Learning

LLM Ops

Context Eng

Security

System Design

Figma

Design Systems

Visual Design

Design Strategy

Automation

Content Marketing

Demand Gen

Go-to-Market

Product Marketing

Positioning

Social Media

Brand

B2B Marketing

SEO & AEO

AI for Leaders

AI Governance

Communication

Management

People Operations

Exec Presence

Storytelling

Goal-setting

Personal Brand

Fundraising

Everyone

Operators

Data Scientists

Business Analysts

User Researchers

Customer Success

Project Managers

HR Professionals

Sales People

Lawyers

Finance

Investors

Real Estate

Educators

Creators

Introduction and Agenda

Speaker's Background and Experience

Core Principles for High-Impact Decisions

Tailoring Communication to Your Audience

Case Study: A High-Stakes Migration Project

The Initial "Migrate Everything" Strategy

Outlining Four Alternative Migration Options

The Winning Strategy and the Decision Document

Analyzing Options with Value, Effort, and Risk

Q&A: Estimation and the Stakeholder Review Process

The Nature of Estimates and Lightweight Decision-Making

Case Study 2: Improving Amazon's Recommendations

Course Information and Q&A: Reversing a Decision

Framework: One-Way vs. Two-Way Door Decisions

Final Q&A and Conclusion

Product managers who drive strategy, development, and launch of products.

Executives and senior leaders who set strategy, lead teams, and drive organizational outcomes.

Broad professional audience — content relevant across many roles and functions.

Executive communication — presenting to boards, writing memos, running all-hands, and high-stakes messaging.

Developing leadership skills — inspiring teams, building culture, navigating organizational complexity, and driving results through others.

Persuading stakeholders, presenting ideas, and getting buy-in across an organization without formal authority.

How to communicate high-stakes decisions

What you'll learn

Why this topic matters

You'll learn from

Colin Matthews