Leadership
Management, teams, and executive skills
78 articlesThe Tiered Context Architecture: Managing AI Working Memory at Scale
When AI context files grow to 1,000+ lines, they degrade the collaboration they were built to support. The tiered context architecture solves this with three in
From Tool to Team: Managing AI as Distributed Engineering
When you're running multiple AI sessions in parallel, you're not using a tool anymore — you're managing a team. The skills that matter shift accordingly.
Synthesis Project Management
A lightweight project management system for human-AI collaboration. Designed for context preservation across conversation sessions and context compaction events
Scaling Synthesis Coding in Your Organization
A practical guide for CTOs and engineering leaders: cost analysis, team rollout strategy, training curriculum, and metrics for adopting synthesis coding at s...
The Future of Engineering Services: Building and Measuring Human-AI Teams
Engineering services must shift from billing hours to delivering capabilities. New measurement frameworks, team structures, and pricing models for AI-augmented
The CTO and chief product officer in the Age of Generative AI: A New Playbook for Technology Leadership
How CTO and CPO roles must evolve in the generative AI era: from chief builder to chief orchestrator, from feature factory to experience architect.
The Power Playbook: Decoding Leadership Dynamics in OpenAI’s Executive Announcement
Twelve power dynamics decoded from OpenAI's executive announcement, revealing how leaders control narratives, reinforce hierarchy, and manage organizational cha
Why I Stopped Chasing ‘High Risk, High Reward’ and You Should Too
Why rewarding risk-taking over value creation is dangerous, and how leaders can shift to prioritizing innovation, skill, and sustainable business practices.
The Power of Being Present: Why Working 24/7 Reduces Your Productivity & Innovation
Why constant connectivity kills productivity and innovation, with research-backed strategies for mindfulness, boundary-setting, and being fully present at work
Beyond Outcomes: Why Great Leaders Prioritize Inputs
Great leaders prioritize inputs over outcomes: how Bhagavad Gita wisdom, Stoic philosophy, and case studies from Pixar and Patagonia support input-focused leade
Every Year, Restart in Your Current Job
The practice of approaching your current role as if you were just hired: listening tours, relationship building, fresh eyes on old problems.
The Evolution of the 50/25 Meeting Format: Why Starting Late is the New On-Time
An updated take on the 50/25 meeting format: why starting meetings 5-10 minutes late creates buffer time that improves focus, reduces stress, and boosts product
An Executive’s Daily Routine for Productivity and Balance (Summer 2023)
A CPTO’s daily routine from 5am workouts to structured deep work and evening wind-down, designed to maximize executive productivity while maintaining balance.
Understanding the Role of Product in Media Companies and Tech Companies
How product team roles differ between tech and media companies, covering stakeholder dynamics, empowered teams vs project management, and four product categorie
Yale CEO Summit June 2023: The Intersection of AI and Leadership
Key themes from the 2023 Yale CEO Summit on AI: regulation challenges, transparency, job displacement, and why AI should augment human judgment, not replace it.
The Poetic Power Play: A Lesson from Indian Poetry and Professor Jeff Pfeffer
Lessons on power dynamics from Dinkar's Hindi poetry and Stanford Professor Jeff Pfeffer's work: why virtues like forgiveness require strength to be respected.
Roles and Responsibilities for Digital Product Development Teams
A comprehensive guide to roles and responsibilities across product management, engineering, design, and operations teams in digital product development organiza
Project Estimation with T-Shirt Sizing & Evidence Based Scheduling Models for Scrum Teams
Introduction "How long will this project take?" and "How much will it cost?" — two questions that can strike fear into the hearts of even the most se...
The Many Hats of Product Managers: Their Indispensable Hands-On Roles as Individual Contributors
Product managers wear many hats as individual contributors across 21 hands-on responsibilities from user research to product launches and roadmap management.
A CEO's Guide to Working with CTOs and CPOs
What non-technical CEOs should expect from their technology and product leaders, how to evaluate them, and what they need from you to succeed.
The Room Where the Story Was Told
A leadership fable about what happens when a capable executive assumes results speak for themselves, and discovers that someone else has been narrating his orga
The World Economic Forum Seven Years Later
Seven years after being inducted as a Young Global Leader, the letter I would have benefited from in 2014: how to engage with the WEF community, what the sessio
Be Curious, Not Judgmental
Why replacing premature judgment with curiosity is one of the most underrated leadership practices, drawing on a Stanford talk by Jeffrey Pfeffer.
Choosing the Right Boss
A leadership fable about how the relationship with your direct manager determines your career more than the company, the title, or the compensation.
The Fable of the Illusory Truth
A leadership fable about how repeated narratives become accepted truths in organizations, and how one leader fought back with data, discipline, and a better sto
How Stakeholders and PDE Should Work Together
The relationship between business stakeholders and product teams is broken at most companies. Here is a framework for how it should actually work.
Activities, Outputs, and Outcomes — A framework for your job
A framework for distinguishing activities, outputs, and outcomes in your work, replacing static job descriptions with a living system for creating real value.
An Example of Respectfully Declining a Meeting at Work That is Already in Your Calendar
A practical example and template for respectfully declining a workplace meeting you previously accepted, with guidance on time prioritization.
OKRs in Media Companies
OKRs work differently in media than in pure tech companies. The editorial side creates unique challenges. Here is what I learned implementing them at the Wall S
The Role of a CPTO
What a Chief Product and Technology Officer does, why the role exists, and why engineering, product, and design should be separate disciplines under one leader.
IT Culture vs. Product Culture
Most media and publishing companies think they have a product culture. They have an IT culture with product titles. Here is how to tell the difference.
Management & Technical Career Growth Tracks (v3)
Version 3 of the management and technical career growth tracks framework, covering engineering, product, design, data, and project management levels.
Reflections on the Yale CEO Summit 2016: Disruption and Leadership in Focus
Reflections on the 2016 Yale CEO Summit, where leaders discussed disruption and leadership, and honored CEOs Terry Lundgren of Macy's and John Legere of T-Mobil
How to be an effective CTO
How to be effective as a CTO by mastering culture, technology, and operations, with five lessons on building stakeholder relationships and organizational influe
90 Day Plan for a CTO in a New Job
A seven-part framework for CTOs starting a new job, covering organizational assessment, metrics, vision, team building, culture, processes, and technology.
7 minus 1 reasons why technology/engineering teams should work on projects
Six valid reasons to justify engineering projects -- product, speed, quality, cost, security, and survival -- plus one anti-pattern to avoid.
CTO Mind Map: Culture, Technology, Operations
A visual mind map organizing the CTO role into three domains -- culture, technology, and operations -- to help technology leaders prioritize and identify gaps.
Dear Makers, On Fridays My Office is Yours — An Experiment
A CTO's experiment sharing his private office with software engineers on Fridays to support maker's schedule productivity and workplace culture.
A Technologist at Summer Davos: Notes From the WEF Annual Meeting of the New Champions
Notes from the World Economic Forum's Annual Meeting of the New Champions in Tianjin, the YGL community, and what a CTO actually gets out of a gathering like th
3 Dimensions of a Technology Team
A three-dimensional organizational design for technology teams balancing product-aligned delivery, partner relationships, and profession-based career growth.
3 Roles of a CTO: Culture. Technology. Operations.
A CTO's three-part framework for 1:1 meetings covering culture, technology, and operations, with detailed checklists for each area of review.
3-5-7 Meeting Format for Weekly Staff Meetings
The 3-5-7 staff meeting format gives each team member 3-5 minutes to answer 7 structured questions covering work, learnings, issues, and collaboration.
Posted Signs for Productive Meetings
Downloadable slides to post as signs in meeting rooms and offices that promote productive meeting habits, available as PDF and Google Slides.
Template For Requesting an Outcome-Focused Meeting
An outcome-focused meeting request template that transforms meetings from time-consuming rituals into results-producing collaborations, with patterns and exampl
Templates for Replying to Meeting Requests & Polite Ways to Decline Meetings
Templates for replying to meeting requests and politely declining meetings where your participation would not add value, with time management tips.
When to have and when not to schedule meetings
Why companies should avoid scheduling meetings before 10am or after 5pm, and why makers need a four-hour uninterrupted block each day.
50/25 Meeting Format
The 50/25 meeting format shortens hour-long meetings to 50 minutes and half-hour meetings to 25 minutes, giving teams time to recharge between sessions.
Using Laptops or Smartphones in Meetings
Why using your phone under the table is like picking your nose, and what to do about device culture in meetings.
What I Learned During the Hacking Attacks of August 28, 2013
Lessons from the 2013 NYT domain hijacking on crisis leadership, human collaboration during emergencies, and technical disaster recovery with backup domains.
Leadership Requires Loyalty, Kindness, and Ethics
Leadership requires three non-negotiable qualities: loyalty, kindness, and ethics. Without all three, a position of power does not make you a leader.
Ray Dalio, Randall Munroe and I Think Alike – Culture of Courage & Candor
Why badmouthing colleagues behind their backs is toxic to organizations, and how senior executives can build a culture of courage, candor, and open courts.
Maker’s Schedule (For Managers Too)
How to implement a maker's schedule with meeting-free Friday afternoons for focused coding and creative work, presented as a team policy memo with FAQ.
HR Classification and Discretionary/Business Job Titles for Makers, Managers and Leaders in Technology
A dual job title system for technology organizations separating HR classification titles from discretionary business titles, with policy guidelines and examples
5 Productivity Tips for Executives in Leadership & Management Roles
Five productivity tips for executives built around the number five, covering daily priorities, concise emails, short presentations, and time management.
Sometimes a Battle Picks You
Every leadership book says 'pick your battles wisely.' But sometimes you don't get to choose. Sometimes a situation demands you stand up, ready or not.
Case for a Consistent, Comprehensible & Cost-Effective Vacation Policy
A case for giving every full-time employee 25 days of paid time off per year, with analysis of unlimited vacation drawbacks and fair accrual policies.
Management & Technical Career Growth Tracks (v2)
Version 2 of the career growth tracks framework, adding a product management track, C-level band, and minimum direct report guidelines for managers.
The Art of the Dual Report: Serving Business and Editorial
Why the senior technology leader at a serious newspaper reports to both the CIO and the Executive Editor, what that structure makes possible, and why translatio
A Players Hire A Players
A players hire A players. B players hire C players. C players hire randomly. Each step reveals something different about insecurity, judgment, and organizationa
A Book That Changed How I Think About Meetings
Patrick Lencioni's Death by Meeting and the principle that has shaped my calendar discipline ever since: a meeting must solve a problem, make a decision, or sha
Schedule Time to Think Every Day
Scheduling dedicated thinking time every workday, separate from meetings and email, is the most important and most neglected habit a leader can develop.
Productive Business Meetings
A comprehensive guide to productive business meetings with links to formats, templates, scheduling guidelines, and device etiquette.
A Memo on Leadership by a Colleague
A colleague's leadership memo covering ego management, active listening, taking blame, treating people with respect, and constructive criticism.
Organizing a Digital Technology Department in a Media Company By Functional Areas
A framework for organizing large digital technology departments in media companies across seven functional areas from engineering to client services.
Confidence in Leaders & Managers and Their Performance: Reinforcing Loop
A systems thinking analysis of how confidence in leaders creates reinforcing loops of success or failure, with strategies to break negative cycles.
Some Pathways for Career Development in a Product Engineering Organization
Career development pathways in product engineering organizations, mapping trajectories from engineer to CTO across engineering, product, and QA tracks.
Trinity Method of Technology Management
The Trinity Method of Technology Management categorizes roles into Creator, Guardian, and Recycler for balanced organizational effectiveness.
CAREER-CLEAR: An Employee Evaluation and Career Development System
The CAREER-CLEAR employee evaluation system with five categories and a 100-point scoring scale for fair, consistent performance assessments.
Benefits of Using IRC or Group Chat & Video Conference During Incident Management
Why technology teams should use IRC or group chat during incident management, with benefits for coordination, transparency, and post-incident analysis.
Build and maintain a cohesive leadership team
Why a cohesive, collaborative leadership team matters more than individual brilliance, with practical advice on building team cohesion.
Organizing a Digital Technology Department of Medium Size in a Media Company
A framework for organizing a medium-size digital technology department into site engineering, platform engineering, and technology operations.
Management Tip: Thank Your Employees For Jobs Well Done
Management tips for effectively thanking employees, covering when to thank, how to personalize appreciation, and avoiding trivialized praise.
Opinion on the Amazon S3 Outage; Checklist for Dealing with Outages
Communication checklists for during-incident and post-incident responses, with leadership principles on owning responsibility for outages.
Management & Technical Career Growth Tracks
A framework for parallel management and technical career growth tracks that lets technologists advance without becoming people managers.
Interviewing By Putting To Work: Evidence-Based Hiring for Superior Results
Three models of work-based hiring assessments that directly observe candidate performance instead of relying on traditional interview questions.
7 Tips for Effective Email
Seven practical tips for effective email communication at work, covering highlighting recipients, avoiding sneaky BCCs, and reply-all etiquette.
The Art and Science of Project Management: Beyond Tools and Techniques
People determine project outcomes more than methodology. A framework for project leadership covering purpose, psychological safety, and quality over speed.
What is Leadership?
Defining leadership as distinct from management: leaders innovate and serve, managers execute plans, and the best leaders win people rather than defeat them.