Leadership
Management, teams, and executive skills
50 articlesThe CTO and chief product officer in the Age of Generative AI: A New Playbook for Technology Leadership
Last week, I watched an AI agent debug a production issue, write a fix, create comprehensive tests, and deploy the solution—all while the product and tech ...
The Power Playbook: Decoding Leadership Dynamics in OpenAI’s Executive Announcement
The Meta-Strategy: Controlling the Narrative In the high-stakes world of AI leadership, those who control the narrative control reality itself. A recent pr...
Why I Stopped Chasing ‘High Risk, High Reward’ and You Should Too
As someone who's spent years in the trenches of entrepreneurship and corporate leadership, I've had my fair share of encounters with the age-old mantra: "...
Beyond Outcomes: Why Great Leaders Prioritize Inputs
Introduction Mediocre leaders focus on outputs, good leaders focus on outcomes, but great leaders, the truly transformative visionaries, prioritize inputs....
The Evolution of the 50/25 Meeting Format: Why Starting Late is the New On-Time
Introduction: An Updated Perspective on Time Management In a continuous quest to boost workplace effectiveness, it's useful to revisit our approaches. Ten ...
An Executive’s Daily Routine for Productivity and Balance (Summer 2023)
My friends occasionally ask how I keep a mostly even keel despite the pressures of an industry that needs to do more with less, and how I’ve managed to com...
Yale CEO Summit June 2023: The Intersection of AI and Leadership
I've admired Jeff Sonnenfeld for more than a decade since I studied his book Firing Back and wrote a review. Having attended Professor Jeffrey Sonnenfeld's...
The Poetic Power Play: A Lesson from Indian Poetry and Professor Jeff Pfeffer
In this post, my first venture into bilingual blogging, I extend my thoughts primarily towards my English-speaking readers, while also preserving the rich ...
Roles and Responsibilities for Digital Product Development Teams
I'm writing this article to share some insights on a topic that's been crucial throughout my professional journey – Roles and Responsibilities in Digital P...
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
Introduction Throughout my career at large companies and startups, I've worked closely with many talented product managers and leaders. Their dedication an...
Cloudflare TV: The CTO Show
Cloudflare‘s CTO, John Graham-Cumming, interviewed Rajiv for the The CTO Show on CloudFlare TV. The CTO role varies enormously from company to company. In ...
Importance of Mentorship Article by Yujin Kim, CTO of WorkMarket
In his recent article about the importance of mentorship, Yujin Kim, Chief Technology Officer at WorkMarket (an ADP company) talks about what he learned fr...
An Example of Respectfully Declining a Meeting at Work That is Already in Your Calendar
Here is an example of how to respectfully decline a meeting to make time to work on a higher priority. We occasionally find ourselves in meetings when our ...
How to be an effective CTO
A CTO's job combines Culture, Technology, and Operations. Each of the three is necessary; a field of knowledge, experimentation, and learning in itself; an...
90 Day Plan for a CTO in a New Job
Starting as a CTO in a new organization is like conducting an orchestra you've never heard before. You need to understand the musicians, learn the repertoi...
7 minus 1 reasons why technology/engineering teams should work on projects
Here are 6 reasons that should be used to justify, prioritize and classify projects engineering teams work on. The 7th item is not a valid reason to be use...
CTO Mind Map: Culture, Technology, Operations
In the role of chief technology officer, you have to be concerned with many topics. Some relate to functions you have direct supervisory responsibility for...
Dear Makers, On Fridays My Office is Yours — An Experiment
Some senior leaders choose to work alongside their teams in cubicles, eschewing private office rooms. New York City’s former mayor Michael Bloomberg is an ...
3 Dimensions of a Technology Team
Organizing Software Engineering Teams to Balance Products, Partners & Professions This organizational design for a technology department aims to optimally ...
3 Roles of a CTO: Culture. Technology. Operations.
This is a guide for CTOs, VPs of Software Engineering and other technology managers responsible for a software engineering organization. The purpose of thi...
3-5-7 Meeting Format for Weekly Staff Meetings
If you are the manager of a team of people at your job, here is a format we suggest for running your staff meetings. We call it the 3-5-7 format because of...
Posted Signs for Productive Meetings
You can post these slides as signs in your meeting rooms and offices or include them at the start of your presentations. You can also open the original Goo...
Template For Requesting an Outcome-Focused Meeting
Most meetings are wasteful because they're organized around what people will discuss rather than what they will accomplish. "Let's meet to talk about the ...
Templates for Replying to Meeting Requests & Polite Ways to Decline Meetings
By default, we should only attend meetings where we are active participants, not passive attendees with not much to contribute to the desired outcome of th...
When to have and when not to schedule meetings
Companies should, by default, avoid scheduling meetings that start before 10am or end after 5pm. If an employee comes to the office at 8am on some days, it...
50/25 Meeting Format
Update (2023 September 17): I published an update to this system based on data, experience, and the advice of colleagues. If you manage a team, value your ...
Using Laptops or Smartphones in Meetings
Using smartphones — or worse, laptops — during in-person meetings diminishes productivity, is disrespectful to others and decreases your brainpower. Yes, s...
What I Learned During the Hacking Attacks of August 28, 2013
One of the most important lessons that was reinforced to me during the Aug 28th hacking attacks on Melbourne IT, the domain registrar for the Web sites of ...
Ray Dalio, Randall Munroe and I Think Alike – Culture of Courage & Candor
On the matter of bad behavior of complaining against others behind their backs, Ray Dalio, Randall Munroe and I share the same viewpoint. This article star...
Maker’s Schedule (For Managers Too)
The following memo from a department head to staff is an example of how to implement a productive maker's schedule at your workplace. This approach recomme...
5 Productivity Tips for Executives in Leadership & Management Roles
Here are 5 productivity tips for executives in leadership & management roles. Each tip involves the number 5. Every morning (or the night before), make a p...
Case for a Consistent, Comprehensible & Cost-Effective Vacation Policy
This article makes a case for having a vacation policy that is simple, sane and standard across the organization. Some organizations have unnecessarily com...
Productive Business Meetings
Here are some suggestions for making business meetings more productive, efficient and effective. Based on readers' feedback, I have split this article into...
A Memo on Leadership by a Colleague
I regularly ask other people for their advice, insights and knowledge about leadership and management. The following is a memo a colleague recently wrote f...
Organizing a Digital Technology Department in a Media Company By Functional Areas
This article presents a system to organize your digital technology department in a media company. It is written for a CTO, CIO or EVP Technology looking fo...
Confidence in Leaders & Managers and Their Performance: Reinforcing Loop
When stakeholders, executives and team members have confidence in the abilities of a leader/manager, it results in their lending greater support to that le...
Janet Kasdan, Director of Technology, Conde Nast Digital
Janet Kasdan shared this recommendation for Rajiv on March 28, 2011 via LinkedIn: Rajiv is an excellent leader. He demonstrates true respect for everyone h...
Trinity Method of Technology Management
In the Trinity Method of Technology Management, tasks and responsibilities are categorized under three types of roles: Creator, Guardian and Recycler. If y...
CAREER-CLEAR: An Employee Evaluation and Career Development System
CAREER-CLEAR is a system for doing fair, consistent and constructive employee performance evaluations and determining employee rank, title and compensation...
Benefits of Using IRC or Group Chat & Video Conference During Incident Management
When a team of engineers is dealing with a real-time incident, such as a system outage, troubleshooting a problem or dealing with a malicious hacking attac...
Build and maintain a cohesive leadership team
For an executive, having a management team of people who are good at their jobs and work well with each other is one of the most important factors that lea...
Organizing a Digital Technology Department of Medium Size in a Media Company
There are many good ways to organize your technology department. This article presents some of them. It is written for a CTO or VP Technology leading a med...
Management Tip: Thank Your Employees For Jobs Well Done
If you supervise employees or are in a senior position relative to some others, make it a habit to thank employees when they do a good job. Here are some t...
It is all about Balance
To be effective at anything in life, balance is required Be it personal life, leadership, management, technical work: balance is essential. You need to be ...
Interviewing By Putting To Work: Evidence-Based Hiring for Superior Results
Originally published April 17, 2007 – Updated and expanded March 17, 2025 Hiring decisions are among the most consequential choices leaders make. A single ...
7 Tips for Effective Email
Some tips for making better use of email at work and in personal life Realize that busy people may skim your email instead of reading it thoroughly, especi...
The Art and Science of Project Management: Beyond Tools and Techniques
Originally published April 1, 2006 – Revised and expanded March 23, 2025 Starting Early, Not Driving Recklessly Fast In my original 2006 article, I shared ...
What is Leadership?
Victory is not defeating others. Victory is winning others. The three skills that people in an organization have are leading, managing, and working. Every ...
Respect and the American Way
Respect must be earned and maintained not expected and demanded. Unlike in some other cultures, I believe the American way is to give respect to those and ...