Middlegame Partners

Get Reliable Information From Your Engineering Organization

Paul Tevis

Executive Coach to Technology Leaders

Allison Pollard

Former Technical Director | Strategic Advisor

Clarifying which type you're asking for—and telling your teams why—changes what you get back.

Distinguish between 3 types of information to make visible

Get the information you need by sharing context, standing firm, and speaking directly to people’s concerns.

Work effectively with pushback

Turn better information into better conversations with your teams, managers, and stakeholders.

Stop defending your numbers & start shaping the conversation

Shape the future of business. Develop the vision, strategy, and influence to make design a critical driver of transformation.


Chief Design Officer | Advisor | Author

Samsung

Amazon

Bank of America

Expedia Group

PayPal

Rachel Kobetz

Chief Design Officer @ PayPal


DLSE07 – Q1 2026

DLSE08 – Q2 2026

A two-week cohort program for Senior Directors, VPs, SVPs, and CDOs ready to lead at the strategic level — not catch up to it. Build the position, influence, and operating model that AI and organizational pressure now demand from design leaders at the top.1. Lock in your strategic positionAlign design to business priorities so your role as a strategic driver (not a service function) is unambiguous.2. Make the business case in C-suite languageConnect design decisions to measurable outcomes. Demonstrate return on design in the terms that drive budget, headcount, and investment.3. Lead organizational change, not just design workBuild the cross-functional influence and stakeholder relationships that let you drive transformation — not just respond to it.4. Build an operating model that scalesStructure your team, systems, and rhythms so design delivers at scale — without the whole thing depending on you.5. Lead into what’s nextLead in territory that didn’t exist before, where roles are blurring, design is moving upstream, and human and AI systems are working side by side.Includes 2 Office Hours with Rachel for personalized guidance on your leadership challenges.

The leadership bar has moved. DLS: Executive is built for what it requires now.

Lead the next evolution of design

Turn design decisions into business results

Drive transformation across the organization

Build an operating model for what’s next

Lead your career with the same intention

Senior Design Leaders: Senior Directors and VPs ready to lead beyond the work and position design as a strategic business driver.

Senior Design Executives: VPs and SVPs leading large teams through AI, shifting org structures, and rising C-suite expectations.

Design C-Suite: SVPs and CDOs using design to lead the business through what’s next — not just respond to it.

Stop being the “number explainer.” Build the stories, systems, and credibility to lead with clarity and confidence in the age of AI.

Data & AI Leader, 19yrs of scaling data

Pier Martin

 Data & AI leader with 19+ years scaling global teams, Executive coach 

Cohort 6

Cohort 7

As a data leader, do you catch yourself asking questions like…- How do I get execs to actually act on my insights instead of tuning out?- How do I influence peers in Product, Ops, and Marketing when they don’t report to me? - How can I build credibility around AI adoption without just demoing tools?- How do I stop my team from being seen as a “ticket shop” and instead as a trusted partner?If you’re not confident about these, this course is for you. This is a hands-on leadership course designed for emerging data leaders, analytics managers, data science managers, and heads of data who want to grow from technical doers into visible, trusted, AI-ready leaders.Before this course, you may feel:- Stuck explaining numbers that don’t lead to action.- Anxious that AI will outpace your team or make your work irrelevant.- Reactive to hype or resistance, rather than steering the narrative.After this course, you’ll:- Turn “data dumps” into compelling stories that executives repeat in the boardroom.- Translate AI pilots into credible business cases that prove ROI, reduce fear, and win support.- Lead your team confidently through change, balancing optimism with realism.

Lead with Data. Inspire with Story. Win with AI.

How to Master Strategic Communication

How to Lead AI Change with Confidence

  How to Build Your Leadership Operating System

Folks who are early in their career, focused only on technical execution, or looking to break into data/analytics should not enroll.

This course is NOT FOR everyone

It is designed for data managers, analytics leads, and heads of data already managing teams and facing leadership challenges.

This is NOT a beginner-level technical course

Overlooked Data Manager delivering dashboards but dismissed in strategy conversations, eager to be trusted for impact.

Stretched Head of Data managing 5-15 people, stuck firefighting, and needing systems to show control and credibility.

Aspiring AI-Ready Data leader, newly promoted from IC, strong technically but lacking storytelling and executive presence.

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

Cohort 3

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.

Master the systems to stop micromanaging and transition from a referee to an orchestrator of a self-running team.

Founder at The Strength Hack

Daimler AG

Airbus

Audi

Toll Collect GmbH

Murk Creusen

Founder & Leadership Coach at Strength Hack

Founding Cohort

You cannot fix burnout by working harder. You have a matching problem.AI is making your team's hard technical skills obsolete faster than they can learn them. You cannot fix this "AI anxiety" or burnout by asking them to work harder. You don't have an effort problem; you have a matching problem.Most Engineering Managers spend 70% of their week trapped in the "Mediocrity Loop" - refereeing personality clashes, fixing broken handoffs, and watching their team's shared knowledge collapse as junior roles vanish. You're bleeding runway and morale.This 30-day accelerator gives you the system to break out. Using the Big Five (or CliftonStrengths) assessment, a proven framework, and the Strength Hack AI, you'll map your team's cognitive architecture and engineer the conditions for psychological safety - not just hope for it.In 4 weeks, you will:<ul><li>Stop Generalist Exhaustion: Identify energy leaks and delegate based on Cognitive Fit, not calendar space. </li><li>Engineer Swift Trust: Use the 6-dimension Matching Compass to translate friction into synergy.</li><li>Drive ROI: Transition from a reactive referee to a strategic orchestrator</li></ul>

Engineer Psychological Safety. Stop Refereeing Your Team.

Shortcut the "Storming" Phase to Engineer Swift Trust

Reclaim 70% of Your Week (Plug the Energy Leak)

Turn Personality Clashes into Solvable Data

Restore the "Who Knows What" Architecture Your Team Lost

Walk Away with a "Plug-and-Play" Facilitation Kit

To get ROI from this course, a real-world team (direct reports or agile squads) is recommended to apply the Matching Compass frameworks.

Team Leadership or Management Role

You must take the free Big Five test (or CliftonStrengths) before to map your personal psychological operating system.

Completion of a Baseline Assessment

The Overwhelmed Engineering Manager / Tech LeadYou lead a hybrid or remote team. You want a data-driven system, not another workshop.

The Ambitious Senior / Staff Engineer<blockquote>You're moving to people manager. You want proven frameworks to lead a team without micromanaging.</blockquote>

The People-Conscious CTO / CPO<blockquote>You own culture and delivery for 10–200 people. Your board wants AI readiness. You need L&amp;D that's credible.</blockquote>

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: The Challenge of Reliable Information

The Dream vs. Reality of Engineering Metrics

The Goal: Strategic Alignment Over Perfect Dashboards

Distinguishing Between Three Types of Information

Why Context is Key for Information Requests

How to Effectively Work with Pushback

Case Study: From Defending Numbers to Shaping the Narrative

Summary and Key Takeaways

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

Engineers and engineering leaders who build, deploy, and scale software systems.

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.

Day-to-day people management — 1:1s, feedback, performance management, hiring, and team operations.

Get Reliable Information From Your Engineering Organization

What you'll learn

Why this topic matters

You'll learn from

Paul Tevis

Allison Pollard