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With Cheryl Haggerty, Chief Client Officer at Shalion, we explore nontraditional careers, values-driven leadership, and how AI reshapes teamwork and trust. 

From progress over perfection to building cross-team flow, Cheryl shares honest stories and practical tools:

• nonlinear career path and authenticity
• values as a compass for purpose
• progress over perfection as a team norm
• cross-team communication and effectiveness
• trust beyond titles and honest leadership
• AI for productivity with human empathy
• designing customer success from first principles
• practical ways to learn AI together
• advice at 15, 30, and last year

Follow the show, share it with some of those building teams, and keep an ear out for Cheryl's return after she finishes her London School of Economics degree, which she started just this year. 

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We challenge the people-process-technology cliché and show how companies behave like living systems shaped by perception, connections, and constraints. Six dynamics reveal why effort often fails, where leverage hides, and how simple rules can trigger better self-organization.

• spotlight logic driving silo dominance and clashes
• nonlinear effects turning effort into leverage or waste
• connection chains creating virtuous, vicious, and neutralizing cycles
• dominance shifts moving priorities as constraints change
• latency causing overcorrections and instability
• self-organization emerging from simple rules and incentives

We give you a simple experiment or exercise you can do this week that can leverage the system for big outcomes.

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Cogs or Cells: Is your company a creaky machine or a living organism? 

Rethinking that question could be the key to advance your career.

What if that metaphor of feeling trapped in a massive, creaky corporate machine is completely wrong? What if your company actually functions more like a living organism: messy, adaptive, and surprisingly biological in its behavior? And why could that make a difference in your career?

In this eye-opening episode, we challenge the traditional mechanical view of organizations and reveal how seeing your workplace as a living system can transform your career trajectory. We explore five fundamental aspects of organizational biology that explain why companies behave less like predictable machines and more like complex organisms: purpose (the DNA that drives behavior), resources (the nutrients that fuel growth), flow (the circulatory system that moves value), connections (the neural pathways that coordinate action), and accumulations (the energy reserves that provide resilience).

This biological perspective explains perplexing workplace dynamics: why handoffs between teams break down, why changes face resistance, and why some workflows never seem to improve despite obvious inefficiencies. Most importantly, it reveals how a few strategic "tiny tweaks" can create enormous positive change. Learn why Amazon discovered that just 100 milliseconds of extra page load time cost them $3 billion in revenue, and how this principle applies to every workflow in your organization.

Whether you're leading a change initiative or simply tired of organizational dysfunction, this episode provides a powerful new lens for understanding workplace challenges. By recognizing the biological nature of organizations, you'll develop the insights needed to navigate office politics, reduce resistance to your ideas, and position yourself for your next promotion. Don't miss the upcoming second episode where we'll dive deeper into the patterns, pitfalls and politics that make change feel risky, and how to overcome them safely.

Ready to see your organization with new eyes? Listen now and discover why the key to your success might be recognizing that you're not a cog in a machine, but a cell in a living system with the power to heal, grow and evolve.

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"Complex systems that work have invariably evolved from simple systems that worked." This powerful insight anchors our season finale as we explore how system dynamics determine the success or failure of transformation efforts in organizations of any size.

Why do most change initiatives fail? Because they attempt to overhaul complex adaptive systems through structural changes alone—new processes, new managers, new org charts—without addressing the system's fundamental purpose. As our panel of experts reveals, a system's true purpose isn't what we claim it to be, but what it actually does. And systems fail reliably by doing what they've evolved to do best: repeating familiar patterns.

Through illuminating examples from companies like Procter & Gamble, Netflix, Google, and Verizon, we unpack four counterintuitive principles that can help you navigate complex systems. We examine how System Dynamics predicts that successful digital transformations either small or driven by a bold leader with a new purpose, how hierarchies can either enable or obstruct performance, and why functional boundaries are not as effective as purpose-aligned structures.

Whether you're leading a transformation in a risk-averse enterprise or trying to inject speed and agility into parts of your business, this episode provides mental models that can help you work with—rather than against—system dynamics. Our panelists share personal experiences from the frontlines of organizational change, offering practical insights applicable to leaders at every level.

As we close our first season, we leave you with a powerful framework for approaching change: understand the system's current purpose, start small when building something new, and recognize that meaningful transformation requires more than superficial restructuring. The path to sustainable success lies in aligning purpose, paradigm, and practice in ways that embrace both discipline and agility.

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What happens when the Agile methodology becomes just another rigid process? In this thought-provoking episode, we dive into the critical difference between "doing Agile" and possessing true agility as individuals and teams.

Drawing parallels to athletics, we explore how business agility resembles a boxer's split-second reactions or a hockey player's ability to change direction at 30 mph. These skills don't come from processes—they come from practice, muscle memory, and instantaneous coordination between perception and action. Similarly, your organization's true adaptability comes from people, not project management frameworks.

We trace the evolution of Agile from its revolutionary beginnings in 2001—when it offered an alternative to the rigid structures causing 70% of software projects to fail—to today's reality where Agile terminology often masks traditional command-and-control approaches with the same 70% failure rate of the 1990s. Like today, it's easier and in many cultures very much 'safer' to blame a process for failure than to adapt to change quickly. 

The heart of the episode showcases our team taking SOTA's agility assessments and discussing the results in real-time. This unscripted conversation reveals how trust enables honest self-reflection, how teams can identify and address performance gaps, and whether to focus improvement efforts on strengths or weaknesses. You'll witness firsthand how psychological safety creates the foundation for true team agility.

Whether you're leading a business or AI transformation, managing software development, or simply trying to make your team more responsive to change, this episode provides practical insights for building disciplined agility among real people—not just implementing another process.

Ready to assess your team's true agility? Message us on LinkedIn for access to the same assessment tools we demonstrate in this episode, and join us in two weeks for our season finale on building systems that guarantee transformation success.

https://www.linkedin.com/company/new-school-it/

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What if the secret to successful digital transformation isn't experimenting harder but working with discipline? Our fourth episode tackles this powerful concept head-on, diving deep into the three crucial levels where discipline transforms organizations.

We begin by exploring how leadership discipline transcends titles and hierarchies—it's about people at any level insisting on good decision-making and aligning everyone toward shared purposes. The Leadership Diamond, an approach used by industry titans, examines how balancing vision, ethics, realism, and courage creates the foundation for sustained transformation.

The conversation shifts to operational discipline, where we unpack how OKRs (Objectives and Key Results) create clarity around outcomes while permitting flexibility in execution. This methodology, credited with Google's  extraordinary success, helps teams navigate the tension between rigidity and chaos in digital transformations.

We also explore discipline at a personal level, after all – digital transformation is about people, so it comes down to you, me, and all of us.

Most powerfully, we demonstrate discipline in real-time through a live OKR exercise. Listen as our team proposes objectives for the podcast, evaluates them through the diamond lens, and navigates the sometimes uncomfortable but necessary conversations about alignment and capacity. This raw demonstration reveals why discipline isn't about perfection but about honesty, intentionality, and continuous practice.

You'll leave this episode understanding why Andy Grove's observation that "there are so many people working so hard and achieving so little" perfectly describes failed transformations—and how discipline provides the remedy.

Whether you're leading a transformation effort or contributing from any position, these principles will help you direct energy where it truly matters.

Have you experienced the power of disciplined approaches in your organization? Do you have a story that could help others? We'd love to hear your insights, get in touch!

Credit where credit is due: mentions in this episode of New School IT (in order of appearance): 

Goals Gone Wild: The Systematic Side Effects of Over-Prescribing Goal Setting. Working Paper No. 09-083. By Lisa D. Ordóñez, Maurice E. Schweitzer, Adam D. Galinsky, and Max H. Bazerman. Boston: Harvard Business School, 2009. https://www.hbs.edu/ris/Publication%20Files/09-083.pdf

Leadership: The Inner Side of Greatness, A Philosophy for Leaders. New and revised, updated, subsequent edition. By Peter Koestenbaum. San Francisco: Jossey-Bass, 2002.

fassforward

• https://www.fassforward.com/
• https://www.linkedin.com/in/rosefass/
• https://www.linkedin.com/in/gmcmahon/

Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs. By John Doerr. New York: Portfolio, 2018.

stackoverflow 

• https://stackoverflow.co/

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What if there was a framework that could transform your organization's digital efforts from struggling projects into a powerful operation that drives real business results? The System of Disciplined Agility (SODA) might be exactly what you're looking for.

The New School IT team tackles the sobering reality that 70% of digital transformations fail despite trillions in spending. Roland, John, Nasheed, and Ryan bring their decades of combined experience to introduce SODA - a systemic framework that goes beyond traditional process methodologies to create lasting change across organizations.

This episode breaks down the three pillars of SODA: discipline (accepting digital transformation as a competency journey), system (defining boundaries and recognizing organization-wide impact), and agility (building behaviors that allow for effective pivoting). The hosts examine how these elements work together to create an environment where software development becomes a core business capability rather than just another IT project.

Through practical examples like Domino's Pizza's remarkable transformation into what one host describes as "essentially a tech company," the team illustrates how SODA principles can revolutionize any business. They share specific indicators to look for - from how initiatives are funded to what status reports measure - that signal whether an organization is truly embracing this approach.

The conversation delves into why traditional approaches fail, how SODA spreads beneficial behaviors throughout an organization, and what leaders need to understand about digital competency development. As Roland puts it, "Working in a SODA way makes employees happier because you go to work with a purpose... and you get stuff done."

Ready to transform how your organization approaches digital initiatives? Listen now to discover how SODA can help you build the discipline and agility needed for true digital transformation success. Stay tuned for our next three episodes, where we'll deep-dive into each SODA element individually!

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Digital transformation isn't just an upgrade—it's a full-scale business shift requiring trust, discipline, and cultural alignment across departments. We break down why software development is so challenging and what makes the difference between forgettable tools and those that become indispensable.

In this revealing episode of New School IT Digital, hosts Roland, John, Nasheed, and Ryan tackle the uncomfortable truth about why digital transformation is so difficult. Through candid stories and real-world examples, they uncover how even the most well-intentioned software projects can fail when developers lose sight of the actual humans who will use their tools. 

The conversation moves beyond technical challenges to expose the cultural and organizational barriers that derail transformation efforts. We learn how departmental silos create language barriers, turning what should be simple collaboration into a game of corporate telephone. The hosts contrast "old school" IT mindsets focused on project completion with "new school" approaches that embrace continuous evolution—revealing why companies stuck in delivery-mode thinking struggle to create software people actually want to use.

What makes the difference between software that gathers digital dust and tools that transform how work gets done? The answer lies in trust, discipline, and a willingness to connect deeply with users' needs. Through examples of software that gets it right (and some that miss the mark), the hosts provide a framework for evaluating your own company's digital efforts.

Whether you're a business leader frustrated by failed IT initiatives, a technical professional trying to bridge the gap with business teams, or someone caught in the middle of a transformation gone sideways, this episode offers both validation and practical guidance. Join us on this journey to reimagine how your organization approaches software development and digital change. 

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We give these examples of software that gets it right:

ZoomInfo (https://www.zoominfo.com)

Perplexity (https://www.perplexity.ai)

Miro (https://miro.com)

Tableau (https://www.tableau.com)

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Get clear on: "What even is a digital transformation? How does it affect your life, and do you love or hate it?"

The digital revolution has already claimed many casualties: Kodak, Blockbuster, RadioShack, Sears, and many others. But what separates the companies that successfully transform from those that become cautionary tales? Four veteran digital transformers bring decades of hard-won wisdom to unpack this critical business challenge.

Our hosts have lived digital transformation from every angle. Roland shares his journey through four major transformations spanning decades. John explains how digital disruption derailed his plan to retire at 55, instead inspiring him to build and sell a successful SaaS business. Nasheed reveals how transformation enabled his career of creative, impactful work, while Ryan describes his unlikely path from actor to Silicon Valley enterprise sales executive.

What emerges is a candid conversation about the realities of digital transformation beyond the corporate buzzwords. The hosts don't shy away from what they hate—the existential fear that triggers resistance, the false agility that masks waterfall thinking, and the exhausting battles between those protecting the status quo and those pushing for change. As John notes, "Traditional management skills often clash with the ambiguity of software development."

Yet they also celebrate transformation's power to democratize opportunity, free talented people from mundane tasks, and enable companies to better serve their customers. Their collective advice forms a practical roadmap: ensure top-down sponsorship with bottom-up implementation, surround yourself with people who have both skills and mindset, focus on external benefits rather than internal metrics, and think systemically about connecting people around shared purpose.

Whether you're leading a transformation, experiencing one, or wondering if your company will be the next Netflix or the next Blockbuster, this episode offers essential perspective on navigating the digital revolution.

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Welcome to New School IT, a Podcast dedicated to the conversation how to get enterprise Data and AI right! 

AI, Data, and Digital Transformation isn’t something you finish, it’s something you master.

1. Don’t let the system defeat your purpose

2. Do the right thing, measure what’s important

3. Don’t follow a plan or process to failure

"Companies with strong digital and AI capabilities have figured out how to generate compounding value." (McKinsey)

https://www.mckinsey.com/capabilities/mckinsey-digital/our-insights/rewired-and-running-ahead-digital-and-ai-leaders-are-leaving-the-rest-behind