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 […]
In mergers, acquisitions, and investment decisions, comprehensive product and tech due diligence is crucial for informed decision-making and risk mitigation. This strategic evaluation process examines critical areas including technical debt assessment, architectural decisions, R&D investment analysis, and team capabilities evaluation. Beyond surface-level code review, it provides deep insights into a company’s technological sustainability, product validation, […]
Running an effective board meeting is one of the CEO’s key responsibilities. When well-conducted, these meetings are informative, insightful, and impactful, benefiting the organization by harnessing the diverse experiences and perspectives of the board team. In reality, many CEOs find board meetings burdensome to prepare for—a duty to fulfill, an obstacle to overcome. This often […]
Preparing for Technical Due Diligence Technical due diligence requests arrive at the worst possible time — mid-fundraise, mid-acquisition, mid-everything. The engineering leaders who handle them well aren’t the ones who scramble. They’re the ones who were already prepared. It’s common for engineering leaders to receive technical due diligence requests on behalf of an investor or […]
As a Chief Technology Officer (CTO) in today’s dynamic tech landscape, mastering the core responsibilities of technology leadership is crucial for organizational success. Through years of CTO coaching and technology leadership experience at Hoola Hoop, we’ve identified four fundamental pillars that determine a technology executive’s effectiveness and impact. Whether you’re a new CTO or a […]
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