Most CTOs Have Shipped Agents. Very Few Have Scaled Them. The question in 2026 is no longer whether agentic AI works. It is why some organizations are compounding value while others are seeing pilots stall and costs spiral. The agentic AI conversation has moved past experimentation. Most CTOs have already shipped something. The issue now […]
When AI Activity Gets Mistaken for AI Productivity. Token leaderboards are the new lines of code. They look rigorous, they travel well in a board deck, and they reward the wrong behavior within six months. Here is why tokenmaxxing took hold, why it will not survive contact with a serious board, and what the scoreboard […]
The Role Convergence Debate. Should your CTO and CPO be one person or two people in distinct roles? There is no universal answer. The right structure depends on your product’s complexity, your team’s maturity, and how tightly your competitive advantage is bound to technical execution. What AI is changing is not the urgency of the […]
The Agentic AI Governance Framework Every CTO Needs in 2026. Deploying AI agents has become the easy part. Most engineering organizations are doing it faster than they can govern it and that gap is where the real risk accumulates. Agentic AI governance has become a defining challenge for leaders in 2026. Dell Technologies recently changed […]
The AI ROI Pressure Point. The conversation has shifted. Most CTOs are not struggling to invest in AI, but they’re struggling to account for it. Boards that spent 2024 asking “what’s your AI strategy?” are now asking “what did it cost, what did it return, and how do you know?” Those are different questions, and […]
What Your CEO Actually Needs From You. Managing up is the skill most CTOs and CPOs never got taught. Your good at building teams, shipping product, and navigating technical complexity. The relationship with your CEO is a different kind of problem, and quietly, it’s where some of the most capable technical leaders I coach and […]
From SDLC to Agentic SDLC. I’ve lived through a lot of process evolutions. The move to agentic development is different in kind, not just degree. It’s changing what it means to lead an engineering organization altogether. CTOs aren’t asking “should we use AI?” anymore. That debate is over. They’re asking: how do we rebuild our […]
Courageous leadership isn’t about individual bravery — it’s about building systems where courage is distributed amongst many. This fourth and final article in the series examines how organizational systems enable or suppress courageous action, and what leaders can do to design distributed courage into the fabric of […]
Discover how CEO coaching helps you grow into a confident and successful leader. In building and leading a company, the hardest challenge is in how you evolve as CEO. Understanding the CEO role requires courage, deeply knowing your product and your people, and navigating the terrain of markets, investors, and the unknown. It’s a struggle! […]
I’ve spent 25 years scaling product and engineering teams, and one thing I’ve learned is that the hardest part of being a CTO is not about technology. For most CTOs and engineering leaders I know and have worked with, it’s not technical competence that holds them back. It’s the leadership aspects of the job that […]
In 25 years of working in and around technology leadership, I’ve watched a lot of shifts and coached many CTOs and CPOs. But how AI is changing the CTO and CPO role feels different from anything I’ve seen before. It’s not just in how software gets built, but in what it means to lead a […]
Courageous leaders don’t just accept a job description — they shape the role they inhabit, including the risk they are willing and able to hold. This article explores the “Role” dimension of the PRS framework: how leaders navigate role given and role taken, manage fear and uncertainty, […]
Leading with courage begins with the self. This article explores the “Person” dimension of the Person–Role–System framework — examining how leaders build courage through self-knowledge, managing information overload, strengthening their mindset, and practicing presence. What is personal courage? Aside from “bravery” and the like, personal courage requires […]
Psychological courage is not optional — it is the foundation of effective leadership. This opening article introduces the Person–Role–System framework and examines how fear and noise undermine leadership judgment, and how courageous leadership can be deliberately cultivated as a skill. Finding your voice in a noisy world […]
The Person-Role-System framework, developed by organizational psychology experts James Krantz and Marc Maltz in 1997, provides a comprehensive approach to understanding how individuals navigate organizational roles. This systems-psychodynamics model reveals the intricate relationship between personal identity, role expectations, and organizational systems. Understanding the Person-Role-System Model for Effective Leadership, Management and Coaching What is the Person-Role-System […]
In this executive leadership episode of EdTech Elevated, Lisa March, President and Founder of Partner in Publishing, interviews Leigh Newsome, Partner at Hoola Hoop and New York University adjunct professor. This episode focuses on scaling EdTech companies through navigating the complexities of technology leadership. Drawing from his experience as both a Silicon Valley engineering leader […]
As executive coaches to CEOs, C-suites and boards, we see a lot of approaches to the role of the CEO. Some are successful and many are not. So what does a CEO do? CEO Priorities and Key Responsibilities Let’s start with the most important things CEOs need to be thinking about: Emotional Intelligence (EI) […]
Chief Technology Officers (CTOs) and Chief Product Officers (CPOs) navigate the complex intersection of technology, product strategy, people leadership and business objectives. At Hoola Hoop, we offer specialized executive coaching tailored to the unique challenges faced by these tech leaders. Let’s start by dispelling some common myths about CTO and CPO coaching. Common Myths About […]
Chief Executive Officers (CEOs) must navigate the complex relationships with their Board of Directors with acumen and dexterity. At Hoola Hoop, we provide executive coaching from former CEOs, C-suite executives and experienced Board members to help you successfully develop and manage your board. Let’s start by dispelling some common myths about board management. Common Myths […]
At Hoola Hoop, CEO coaching is considered part of the executive team’s development. CEOs do not operate alone, they engage and, in many ways, are dependent on the broader team. Team development focuses on the following: Enhanced Strategic Thinking It is critical to equip your executives with advanced problem-solving skills and a forward-thinking mindset […]
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