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In partnership with

Welcome, builders of the future.

Today, it’s about controlling high-pressure moments.

If you’ve ever had a CEO throw a half-baked idea at you mid-sprint and expect a fully-formed plan by EOD, you’re not alone.

When the stakes are high and expectations vague, jumping straight into build mode is tempting - but it may be risky.

This guide is your cheat code for holding the line, asking the right questions, and turning chaos into strategy without looking like a blocker.

Plus: tools to turn Python into apps, automate Windows, supercharge prompts, handle support, bookkeeping, and Copilot on Mac (Yes! you heard that right)

Let’s dive in.

My favorite weekly finds

🛠️ Tools

• Use Brainnote as an AI thought organizer to summarize your ideas in seconds

• Preswald: Transform your Python scripts into interactive data apps and dashboards—no frontend code required.

• Microsoft Copilot for Mac: Microsoft's AI chatbot is now available on macOS, offering features like image generation and summarization.

• Pig: Automate Windows applications through chat or code, enabling remote control without programming skills.

• Lemni: Set up AI agents for all your customer interactions—from phone calls to email support and proactive outreach.

• Mesh: Automate your bookkeeping and get instant answers to your financial questions with this AI-powered tool.

• Promptize: Instantly improve your prompts across all AI tools, getting better results without the hassle of manual prompt engineering.

📰 Intelligent Insights

• OpenAI recently discussed using AI to accelerate drug evaluation with the FDA, with Elon Musk’s DOGE team also involved.

• Uber has teamed up with Pony.ai to roll out autonomous robotaxis on its platform, starting in the Middle East this year, with global expansion plans.

• Amazon unveiled Vulcan, a “touch-sensitive” warehouse robot that can process 75% of its inventory.

• Apple’s SVP Eddy Cue hinted at integrating AI search engines from OpenAI, Perplexity, and Anthropic into Safari, potentially replacing traditional search engines as Google’s stock drops by 7%.

• And if you’re in HR, beware: IBM automated the roles of 200+ HR employees using AI, redirecting savings to hire sales reps and coders.

📰 ICYMI

• AI Roadmaps Need Experiments, Not Features (learn more)

• Leading with Confidence Around Powerful Stakeholders (learn more)

• Your ‘Perfect’ Strategy Plan Is Already Dead (learn more)

Staying Strategic When the CEO Drops a Curveball

Why should I care?

Picture this: the CEO drops into Slack or walks over after a VC call with a “brilliant” new idea. Maybe they just heard it from a customer.

Or dreamt it up in the shower. (you know what I mean…)

Either way, they’re jazzed. It’s vague.

And somehow, you’re supposed to turn it into a rock-solid plan… by end of day.

Sound familiar?

Yeah. It’s an unreasonable ask. But welcome to the job.

As a PM (especially if you’re gunning for that Director+ seat), your job is to bring clarity to chaos.

The tricky part?

When urgency kicks in, the pressure pushes you straight into "do" mode; wireframes, roadmaps, delivery dates; before you've even named the actual problem.

You don’t want to seem like a blocker. So you dive in. Start typing. Maybe mock something up.

But guess what? That’s not a strategy. That’s just speed.

And it’s a trap.

This dance happens a lot in fast-paced startups or when the trust between you and leadership is still forming. But if you want to be seen as a true strategic partner; not just the Feature Factory foreman; you need to hold the line.

Here’s what helps.

A simple five-step tool for staying strategic under pressure. It’s not fancy.

It’s not long. But it helps you respond with clarity when you’ve got zero time and max expectations.

Let’s dive in.

1. Get Clear on What, When, and Why

The key to understanding what’s really needed is asking for more context.

Big difference here; did the CEO hear this idea at a conference and want to casually add it to the backlog?

Or are they prepping for a board meeting or a customer pitch, and they need a solid plan now?

Before you fire off any questions, reassure them you’re on it.

This helps set the stage for your questions to land in the right way.

It’s not about pushing back; it’s about getting the full picture to make sure you’re heading in the right direction.

2. Ask Questions That Get Them Thinking

Your job here is to help them think through their idea more clearly.

You could ask something like, “I want to make sure we’re on the same page. I’m guessing the goal here is X, right?” Or, “So if we do X, then Y should happen, is that the idea?”

This requires you to think big-picture in real-time, which takes practice. Don’t stress if you don’t nail it the first time, but keep pushing yourself to get the clarity you need.

Walk away (or leave the chat) with a solid grasp of what they want and the logic behind it.

Heads up: Not every CEO is great at explaining the reasoning behind their requests, and not everyone’s logic is flawless.

But everyone has a reason for asking you to do something, even if it’s just their gut feeling.

Your job is to figure out that reasoning.

3. Set Expectations and Give an ETA for a Plan

By now, you’ve got a good idea of what’s needed and when.

If you’re confident you can meet the request, let them know: “I’ll have a draft for you in 2 days.”