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The 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 ...

· 18 min read
Leadership New

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...

· 14 min read
Leadership New

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: "...

· 8 min read
Leadership New

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....

· 11 min read
Leadership New

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 ...

· 4 min read
Leadership New

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...

· 6 min read
Leadership New

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...

· 4 min read
Leadership New

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 ...

· 6 min read
Leadership New

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...

· 14 min read
Leadership New

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...

· 9 min read
Leadership New

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...

· 8 min read
Leadership New

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 ...

· 1 min read
Leadership New

William Lewis, Former CEO of Dow Jones & Publisher of The Wall Street Journal

William Lewis shared this recommendation for Rajiv on June 04, 2020. Rajiv is an inspirational digital leader, who combines technical expertise with strate...

· 1 min read
Leadership New

Kathryn Friedrich, EVP, GM of Operations at Conde Nast Entertainment

Kathryn Friedrich shared this recommendation for Rajiv on November 25, 2019 via LinkedIn: I started at Thrive Global at the same time as Rajiv. We were bot...

· 2 min read
Leadership New

Katharine Bailey, SVP, Product at The Wall Street Journal

Katharine Bailey shared this recommendation for Rajiv on November 21, 2019. This is the full version of what she wrote and also shared via LinkedIn: I work...

· 5 min read
Leadership New

Jordan Sudy, VP, Goldman Sachs

Jordan Sudy shared this recommendation for Rajiv on November 20, 2019 via LinkedIn: I’ve had the honor of working under Rajiv at both the NYT and the WSJ. ...

· 2 min read
Leadership New

Che Douglas, VP of Design at Booking.com

Che Douglas shared this recommendation for Rajiv on November 17, 2019 via LinkedIn: Rajiv is a professional, dedicated, smart and inspiring leader — his ac...

· 2 min read
Leadership New

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...

· 1 min read
Leadership New

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 ...

· 2 min read
Leadership New

The Leadership Fairy Tale Problem: Why Most Leadership Advice Will Sabotage Your Career

Walk into any airport bookstore and you'll find an entire wall devoted to leadership books. Browse LinkedIn and you'll see countless posts sharing "leader...

· 11 min read
Leadership New

Reflections on the Yale CEO Summit 2016: Disruption and Leadership in Focus

Yesterday, I attended the Yale CEO Summit for the second time. The summit, held at the Waldorf Astoria in New York City, brought together some of the world...

· 3 min read
Leadership New

Denise Warren, Executive Vice President, The New York Times

Denise Warren shared this recommendation for Rajiv on Aug 5, 2016 via LinkedIn: It is with strong conviction that I recommend Rajiv Pant. During our work t...

· 2 min read
Leadership New

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...

· 9 min read
Leadership New

Malu Menezes, Executive Director of Technology, The New York Times

Malu Menezes shared this recommendation for Rajiv on June 24, 2016 via LinkedIn: I worked with Rajiv at the New York Times while he was VP of Engineering a...

· 1 min read
Leadership New

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...

· 10 min read
Leadership New

Robert A. Sauerberg Jr., President & Chief Executive Officer, Conde Nast

Bob Sauerberg shared this recommendation for Rajiv on Apr 14, 2016 via LinkedIn: Rajiv is a visionary and a great tech leader. He has all the skills necess...

· 1 min read
Leadership New

Mark Thompson, President & Chief Executive Officer, The New York Times Company

Mark Thompson wrote this recommendation for Rajiv on April 13, 2016: Rajiv is a very strong digital executive with rock solid credentials in both engineeri...

· 1 min read
CTO
Leadership New

Womensphere Summit 2016

At the Womensphere Summit 2016 in New York City, Rajiv spoke on Supporting and Championing Women in Tech Leadership. (March 6, 2016)

· 1 min read
Leadership New

Joy Goldberg, Director, Portfolio Management at The New York Times

Joy Goldberg shared this recommendation for Rajiv on October 22, 2015 via LinkedIn: Rajiv is unique. He's intensely interested in every person regardless o...

· 1 min read
Leadership New

Womensphere Summit 2014 – NYC

At the 2014 Womensphere Summit, in addition to opening remarks with Analisa Balares – CEO & Founder of Womensphere and fellow YGL, Rajiv spoke in theCareer...

· 1 min read
Leadership New

Why I left being CTO of The New York Times, joined a startup, and am pledging 20% of my equity to charity

As The New York Times’ chief technology officer, I had a crucial role in guiding the company’s successful transition to digital, and an opportunity to work...

· 5 min read
Leadership New

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...

· 2 min read
Leadership New

Womensphere Summit 2015

At the 2015 Womensphere Summit in New York City – Rajiv spoke on Advancing Women's Leadership & Innovation. (February 25th, 2015)

· 1 min read
Leadership New

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...

· 2 min read
Leadership New

Reflecting on the Yale CEO Summit 2014: A Confluence of Global Leadership and Local Sensitivities

I recently attended the Yale CEO Summit, a gathering of some of the world's most influential leaders across various sectors. The summit, held at the Waldor...

· 4 min read
Leadership New

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 min read
Leadership New

IESE Business School Executive Education Course

Rajiv was invited to be a Guest Speaker in the Executive Education course at the IESE Business School. He spoke about leadership, management and organization...

· 1 min read
Leadership New

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 ...

· 11 min read
Leadership New

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...

· 5 min read
Leadership New

Landmark CIO Summit 2014

At the Landmark CTO Summit 2014, Rajiv spoke with Rhonda Vetere, Chief Technology Officer – Estee Lauder and Abe Cytryn, Chief Technology Officer – Time In...

· 1 min read
Leadership New

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...

· 2 min read
Leadership New

Stanford University’s Graduate School of Business – Guest Speaker on Organizational Behavior

At Stanford University's Graduate School of Business, Rajiv was a guest speaker / panelist and spoke about organizational behavior at two sessions to MBA s...

· 1 min read
Leadership New

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...

· 1 min read
Leadership New

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 ...

· 11 min read
Leadership New

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...

· 2 min read
Leadership New

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...

· 1 min read
Leadership New

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 ...

· 3 min read
Leadership New

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...

· 4 min read
Leadership New

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 ...

· 7 min read
Leadership New

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...

· 11 min read
Leadership New

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...

· 6 min read
Leadership New

Matt Stowe, Director of Technology, Conde Nast

Matt Stowe shared this recommendation for Rajiv on May 21, 2013 via LinkedIn: Rajiv is a compassionate leader who strives to help each individual in his or...

· 1 min read
Leadership New

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...

· 1 min read
Leadership New

Land du Pont, Executive Director, Product Management, Conde Nast

Land du Pont shared this recommendation for Rajiv on February 17, 2013 via LinkedIn: During the three years we worked together, I learned so much from Raji...

· 1 min read
Leadership New

Bane Hunter, Executive Director, Project Management, Conde Nast

Bane Hunter shared this recommendation for Rajiv on February 16, 2013 via LinkedIn: I had the pleasure of working with Rajiv during his tenure as an execut...

· 1 min read
Leadership New

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...

· 1 min read
Leadership New

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...

· 8 min read
Leadership New

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...

· 4 min read
Leadership New

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...

· 2 min read
Leadership New

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...

· 1 min read
Leadership New

Jessica Perry, Vice President, Product Planning/Management, Conde Nast Digital

Jessica Perry shared this recommendation for Rajiv on December 19, 2010 via LinkedIn: Rajiv is a terrific business partner who can skillfully translate tec...

· 1 min read
Leadership New

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...

· 3 min read
Leadership New

Oscar Sumano, Associate Director, Technology Operations, Conde Nast

Oscar Sumano shared this recommendation for Rajiv on May 12, 2010 via LinkedIn: Rajiv is very open-minded when it comes to technology. He looks for the rig...

· 1 min read
Leadership New

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...

· 3 min read
Leadership New

Ted Nadeau, SVP, General Manager, CondeNet, Conde Nast

Ted Nadeau shared this recommendation for Rajiv on September 10, 2009 via LinkedIn: Rajiv and I worked together for two years at Conde Nast Digital. Rajiv ...

· 1 min read
Leadership New

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...

· 3 min read
Leadership New

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...

· 2 min read
Leadership New

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 ...

· 1 min read
Leadership New

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 ...

· 6 min read
Leadership New

Shannon Brown, Director of Product Management, Knight Ridder Digital

Shannon Brown shared this recommendation for Rajiv on November 30, 2006 via LinkedIn: Rajiv is a visionary technologist with the ability to communicate and...

· 1 min read
Leadership New

Mark Sun, Senior Director of Engineering, McClatchy Interactive

Mark Sun shared this recommendation for Rajiv on November 27, 2006 via LinkedIn: Rajiv is a very resourceful manager. He always able to find supports from ...

· 1 min read
Leadership New

Fred Mann; former VP, National Programming and Regional VP, Knight Ridder Digital; GM, Philly.com

April 25, 2006 To Whom It May Concern: In my long career as a journalist, and digital media manager, I have learned that hiring the right people is probabl...

· 3 min read
Leadership New

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 ...

· 9 min read
Leadership New

Shannon Kinney, Senior Director, Product Development, Knight Ridder Digital

Shannon Kinney shared this recommendation for Rajiv on November 18, 2005 via LinkedIn: I managed Product Development at KRD and looked to Rajiv to help me ...

· 1 min read
Leadership New

Daniel Finnigan, President and CEO, Knight Ridder Digital

Dan Finnigan shared this recommendation for Rajiv on April 24, 2005 via LinkedIn: Rajiv is very bright, hard-working, creative and passionate about his eng...

· 1 min read
Leadership New

Ches Wajda, Design Director, Philly.com and Knight Ridder Digital

Ches Wajda shared this recommendation for Rajiv on September 27, 2004 via LinkedIn: Rajiv already was at legendary status when I arrived at Philly.com (whi...

· 1 min read
Leadership New

Searching Instead Of Browsing: Organizing Information Using Labels as Meta-Data

Being able to assign labels to content to organize information for searching is superior to placing content in folders for manual browsing. The folder conc...

· 3 min read
Leadership New

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 ...

· 3 min read
Leadership New

Ken Doctor, VP/Content Services, Knight Ridder Digital

Feb. 22, 2004 Letter of Reference Re: Rajiv Pant From: Ken Doctor, VP/Content Services, Knight Ridder Digital Few people elicit great enthusiasm from refer...

· 3 min read
Leadership New

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 ...

· 3 min read
Leadership New

An All-Nighter at Work Followed by a Terrorism Threat Scare

We had too much excitement at work pulling an all-nighter. Then when we thought we could go home and sleep, there was a terrorism threat at our building. A...

· 3 min read
Leadership New

Tony Ridder, Chairman and CEO, Knight Ridder

Congratulatory letter from Tony Ridder, Chairman & CEO, Knight Ridder P. ANTHONY RIDDERCHAIRMAN ANDCHIEF EXECUTIVE OFFICER KNIGHT RIDDER50W. SAN FERNANDO S...

· 1 min read