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Riding the Risky Waves of TPM: Chaos, AI, and the Art of Mitigation

Join me as I navigate the tumultuous seas of risk in Technical Program Management, from dependency disasters to ethical AI dilemmas, all while juggling chaos and automation. Here's what I’ve learned about proactive playbooks and real-time escalation in this unpredictable landscape.

TPMxAI

01 Jun 2025 — 4 min read

Riding the Risky Waves of TPM: Chaos, AI, and the Art of Mitigation

Navigating Startup Chaos And Risks

It's a Tuesday morning, and I find myself standing in front of a whiteboard covered in colorful Post-it notes, each representing a project dependency that could either make or break my week. As the resident TPM in a bustling startup, I've learned that chaos is not just a part of my job description; it’s practically my middle name. Today’s agenda? Assess the risks lurking in the shadows of our ambitious AI initiatives.

As I sip my third cup of coffee, a thought crosses my mind: risk management is like surfing. You can prepare for the perfect wave, but if you don’t know how to paddle through the riptide, your chances of wiping out increase exponentially. And let me tell you, there are days when my surfboard feels more like a flimsy floatie.

Let’s start with dependency risks. Imagine you’ve got a key component of your project relying on an external vendor. They send you a lovely email at 8 PM on a Friday saying they’re pivoting their entire platform, effective immediately. Cue the panic! In a proactive playbook, I’ve learned to establish contingency plans early on. Having a backup vendor or a way to pivot internally can turn a potential disaster into a mere inconvenience. I often joke that I’m not a project manager; I’m a professional juggler—except my balls are made of glass, and I can’t drop any.

Then there’s schedule risk. Ah, the ever-elusive timeline. As a TPM, I’ve found that creating a Gantt chart is akin to crafting a work of art. Each task is a brushstroke, and the final picture is a beautiful disaster waiting to unfold. In a world where everything seems to shift at the speed of light, I always leave room for ‘the unexpected’ in our timelines. It’s like planning a road trip: you can map out the route, but you better pack snacks for the inevitable detours.

Now, let’s talk technical debt. It’s like having a credit card balance that keeps accumulating interest. Initially, it feels great to take shortcuts to meet deadlines, but eventually, you find yourself in a fiscal crisis. As a TPM, I’ve made it my mission to advocate for regular tech debt sprints—yes, I’m that person in the meeting who insists on dedicating resources to clean up the code even when everyone else is itching to roll out the flashiest new feature. It’s not glamorous, but trust me—the long-term benefits are worth the temporary grumbling.

And speaking of unglamorous, let’s dive into AI and ethics risks. In a world where we’re programming algorithms to make decisions, the stakes are high. I often remind my team that with great power comes great responsibility—or in my case, great anxiety. There was a moment we were developing a recommendation engine, and I had to pause and ask, ‘What kind of biases are we unintentionally programming into this?’ We created a task force dedicated to ethical AI, and now we have regular checks in place to ensure our algorithms are as impartial as a robot can be. While the idea of AI is thrilling, the ethics surrounding it can feel like walking a tightrope over a pool of piranhas.

Now, as much as I love a good proactive playbook, let’s face it: sometimes, plans go awry, and real-time escalation becomes necessary. I vividly recall a day when our app went down due to a massive data breach. My heart raced as I watched the Slack notifications explode like popcorn. In those moments, I revert to my TPM training. I gather our incident response team, establish a communication plan, and ensure everyone knows their role—think of it as organizing a chaotic flash mob, but instead of dancing, we’re troubleshooting.

As we scramble to contain the situation, I realize that the true essence of TPM lies not in avoiding risks entirely, but in how we respond to them. It’s about fostering a culture of transparency and agility. When a team feels empowered to communicate potential issues before they escalate, we can mitigate risks before they spiral out of control.

So here I am, a startup TPM juggling chaos and AI automation, continuously learning how to surf the risky waves of dependency mishaps, schedule slip-ups, technical debt, and ethical conundrums. Each day feels like a new challenge, but like any good surfer, I enjoy the ride—even the wipeouts. After all, every wave teaches me something new.

In closing, I would encourage my fellow TPMs to embrace the chaos and remember that risk management isn’t just a checkbox on your to-do list; it’s a mindset. Whether you’re crafting a proactive playbook or managing real-time escalation, keep your surfboard balanced, your contingency plans ready, and don’t forget to have a little fun along the way.