Process Debt

Where does your work live? If the answer is “everywhere and nowhere”—scattered across Slack threads, buried in email chains, lost in forgotten SharePoint folders—then this episode is for you.

In this episode of Process Debt, Chris and Toby unpack the messy reality of modern knowledge work and ask a provocative question: Is your work homeless? Together, they explore what it means for work to lack a consistent, discoverable home and how that contributes to chaos, confusion, and stalled productivity.

From shared drives that feel more like junk drawers to the false promise of “pretty” over “practical,” they dig into why clarity, structure, and ownership matter—and how to begin “cleaning your room” before trying to fix the whole house.

Whether you're a seasoned executive or a new hire still hunting for your team’s silverware drawer, this episode offers a candid, often funny, and ultimately hopeful conversation about how to give your work a proper place to live.

In this episode of Process Debt, Chris and Toby explore one of the most overlooked issues in modern business: the invisible constraints that shape our work as knowledge workers. Unlike physical jobs, where constraints are visible and immediate—think long lines or broken machinery—knowledge work is plagued by hidden bottlenecks, shifting priorities, and the chaos of constant context switching.

Together, they explore:

• Why visibility matters—and how invisibility in knowledge work kills productivity
• How post-COVID workplace structures misread productivity signals
• The cost of endless communication and the myth of “inbox zero”
• Context switching and the surprising stat that it takes 24 minutes to refocus
• What managers and ICs can do to reduce friction: tracking blocks, guarding time, clarifying priorities
• Why “planning at 100%” is a recipe for burnout
• Lessons from Drucker, Cal Newport, and some real-life team fails (and recoveries)

This episode is a conversation about how we work, why we get stuck, and what we can do—individually and as leaders—to make invisible constraints visible and manageable.

We’ve all been there—drawn in by a sleek SaaS website, hypnotized by animated walkthroughs, and convinced this tool will finally solve our team’s biggest pain points. But behind the glossy UI and clever branding? A clunky mess that no one wants to use.

You just got SaaS-fished.

It’s the business version of catfishing:

• The video showed elegant workflows.
• The reps promised seamless integrations.
• Your team expected a miracle.

And what did you get? 💸 A tool that doesn’t fit the use case 🤯 A confused, overburdened team 🚫 Zero adoption and sunk cost

🚩 Common Red Flags You’re Being SaaS-Fished:

• “Low-code / no-code / some-code” buzzwords
• Beautiful mockups that don’t match reality
• It promises to solve everyone’s problem
• Add-ons that double the total cost
• Integrations that should work—but don’t

💡 Prevention Checklist:

• Sandbox it. Never trust the happy-path demo.
• Get real users. Not just execs or IT buyers.
• Proof of concept. Spend some money to test before scaling.
• Process first. Don’t fix a tool problem when you have a workflow problem.
• Watch integration scope. APIs ≠ automation.

Let’s stop believing every tool will magically solve process debt.

The grass isn’t greener—it’s just better marketed. 🌱

We made it to episode 35—halfway to 70, not that it means anything… or maybe it does? In this episode, Chris and Toby take a raw, hilarious, and deeply practical look at what it really means to be “productive” in a modern knowledge economy that thrives on exhaustion and disconnection.

From cobblers and calendars to Cal Newport’s Slow Productivity, we break down:

• Why most productivity systems are lying to us
• The difference between projects and tasks, and why our brains don’t treat them differently
• The social pressure of busyness and how it feeds into the exhaustion Olympics
• The seductive appeal of working at a natural pace
• Why you should give yourself permission to do fewer things with higher quality—and how to actually do that

We also explore how to:

• Set boundaries that prioritize clarity over constant accommodation
• Shift from reactive task-juggling to intentional, project-focused work
• Stop letting other people’s urgency become your problem

This one’s for anyone who’s ever ended the day staring at a task list and wondering: Was I even productive?

Mentioned in This Episode:

• Slow Productivity by Cal Newport
• The “Inbox-first” trap
• The power of time blocking and the myth of urgency

AI has transformed how we work—but not always for the better.

In this episode of the Process Debt Podcast, Chris and Toby unpack the paradox of AI-driven productivity. Yes, we can create more than ever before. But with that power comes rising expectations, ambiguous goals, and a growing sense of burnout.

Together, they explore:

• Why AI increases input volume but doesn’t guarantee better outputs
• The hidden pressure of “performing with AI” in the workplace
• How teams are skipping alignment and verification in favor of speed
• The false promise of AI as a magic problem-solver
• And how slow productivity might be the counterbalance we need

If you’ve ever felt like you’re drowning in tasks, prompts, and unspoken expectations—this one's for you.

📌 Featuring thoughts on Cal Newport’s Slow Productivity 📌 Real talk on what AI can’t fix in your systems 📌 A reminder that not every workflow needs a Ferrari

You're paying full price for tools your team barely uses. That’s not SaaS fatigue. That’s a zombie system.

Every business has them—tools nobody owns, nobody uses well, but everyone keeps paying for.

They hide in plain sight:

• That analytics platform no one logs into
• A CRM that only stores names, not relationships
• Jira instances you can't shut down because "there’s still some data in there"

Zombie systems don’t scream. They quietly erode your margins, confuse your teams, and fragment your workflows.

Here’s the kicker: Most teams don’t kill zombie systems because nobody is asking the hard question:

“What value are we getting out of this tool?”

Fix it Friday is your chance.

🔍 Pick one tool.

🤔 Ask what it’s supposed to do.

🧠 Learn one new function. Then decide—optimize it, or kill it.

Start small. Start curious. Want help auditing your zombie stack? I’ll show you how to track them—and bury them. 💀

#processdebt #opsstrategy #saaswaste #fixitfriday

In today's episode, Chris and Toby explore the crucial topic of how most businesses optimize their internal silos rather than focusing on what happens between them. They discuss the importance of curiosity, contextual understanding, and the detrimental effects of a myopic approach to business processes. The conversation spans various examples, including challenges faced in product development, client servicing, and system implementation, illustrating how misaligned incentives and poor communication lead to inefficiency. They also address the complexities of fixing organizational culture, drawing from experiences in the emergency department and corporate fiascos like Wells Fargo. The key takeaway: effective management and curiosity are essential for driving meaningful changes in business processes.

00:00 Introduction and Casual Banter

00:04 Episode Numbering Mishap

00:49 Today's Topic: Optimizing Between Silos

01:26 Human Nature and Myopic Tendencies

03:29 Examples of Silo Optimization Issues

13:41 Fix It Friday: Solutions and Strategies

17:59 Conclusion and Sign-Off

oin Toby and Chris in Episode 31 as they delve into the intricacies of supply chains, inspired by current headlines. They discuss the massive scale and impressive efficiency of modern supply chains, using examples like McDonald's fry factories and the production of iPhones. The conversation extends to historical contexts, such as the textile industry and the evolution of manufacturing across different countries. They also connect these large-scale processes to the everyday challenges in business, emphasizing the importance of standard processes and the pitfalls of customized outputs. This episode offers a compelling look at how mass production shapes our world and the lessons businesses can learn from it.

00:00 Introduction and Milestone Celebration

00:23 Diving into Supply Chains

01:19 The Efficiency of Modern Manufacturing

04:52 Historical Context and Evolution of Supply Chains

09:15 Challenges and Future of Supply Chains

14:38 Reflections on Business Processes

20:59 Conclusion and Final Thoughts

Follow up

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Underlord can make mistakes. We're all humans after all ;)

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In episode 29 of the Process Debt Podcast, the hosts humorously discuss their own performance and continue their exploration into how businesses manage customer expectations and deficiencies in process. They reflect on personal experiences, including the misconceptions regarding the success of big businesses and the reality behind corporate roles. The conversation addresses whether the customer is indeed always right and the complexities of serving a diverse range of stakeholders. The episode delves into how communication breakdowns often lead to process debt, with insights into incremental improvements and managing customer relationships effectively. Lastly, they touch on the impact of technology and artificial intelligence on modern business processes and customer satisfaction.

00:00 Introduction and Episode Kickoff

00:48 Corporate Culture and Misconceptions

02:04 Customer Expectations and Realities

03:41 AI and Future Technologies

06:16 Communication Breakdowns

10:01 Perfectionism and Feedback

14:44 Conclusion and Final Thoughts

Welcome to Podcast #28! It's Fix It Friday, and we're diving into why businesses struggle so much with change. Join hosts Toby and Chris as they explore why half of all business initiatives fail and discuss insights from the CEB Corporate Leadership Council's 2016 study. Discover why alignment, clear objectives, and understanding the 'game' are critical to successful change. Hear personal anecdotes, such as the pitfalls of implementing systems like SAP without proper alignment. Plus, learn about the innovative use of AI and generative prompts for efficient work processes. Tune in for a deep dive into the challenges of change management and proactive solutions.

00:00 Introduction and Greetings

01:05 Why Businesses Struggle with Change

01:45 Statistics on Change Initiatives

03:52 Real-World Examples of Change Failures

11:44 The Impact of Poor Change Management

13:46 Strategies for Effective Change Management

18:22 Generative AI and Prompt Engineering

20:41 Conclusion and Final Thoughts