The Complexity of Leadership

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 […]

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 […]

Purpose, motivation, and resilience are essential for an organization to sustain success. These client case studies focus on what happens when an organization faces significant challenges due to trauma, M&A, market conditions, etc. All show a lack of clear purpose and confused organizational responses to change. We emphasize the importance of leadership in fostering a […]

Role is a complex key component of all organizations. We offer a framework for defining the way one works-in-role: their specific assigned duties, part in the overall mission, unconscious function, and the way they understand and work within an organization’s systems of tasks and sentience.

Discover comprehensive insights into succession planning best practices through our analysis of 14 leading companies across multiple industries. This in-depth study examines the choices companies face when creating or improving their succession planning and management systems. It identifies several themes, including the role of human resources, the criteria for identifying high potential candidates, the relationship […]

Today’s performance management systems need a more effective approach that aligns with modern workforce requirements, emphasizing the importance of specific, in-the-moment feedback. One of today’s most valuable workplace assets is actionable, in-the-moment feedback, which is too often buried, lost or just not delivered in today’s ineffective performance management systems. Traditional performance management systems are out-of-sync […]

The 9/11 attacks on the World Trade Center devastated this investment bank. We discuss our work in helping Sandler O’Neill & Partners’ remaining managing director, employees and families, recover from the trauma of losing 39% of their friends and colleagues. We present the challenges and successes of bringing together survivors, families, volunteers and new employees […]

Through a case study of a senior executive at a foreign bank, we look at the complex dynamics between leadership, teamwork and organizational culture, and how to help leaders navigate the challenges of a rapidly changing business landscape. We address the importance of understanding the psychological factors that drive individual and organizational behavior and decision-making; […]

Leaders must be able to identify and manage workplace stresses and anxieties, what we call “troubling, frightening bits” or TFBs, that originate from employees, work, organizational dysfunction, and external events. If unaddressed, TFBs can negatively impact an organization. “Psychological containment” is the ability to keep TFBs within limits, enabling teams to stay focused and aligned […]