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My favorite weekly finds

🛠️ Tools

• Cursor is super strong product for coding with AI that a lot of our nerdiest friends are using.

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

• Trickle helps you build apps, landing pages, and forms from just text prompts.

• Love Blitzit! It’s a desktop timer app that helps you stay focused by tracking your time and removing distractions

• Findr is your personal search engine that remembers everything for you across apps, files, and notes (five free uploads / searches per day).

• You can literally talk to and text ChatGPT by calling 1-800-ChatGPT in the U.S. or by sending a WhatsApp message to the same number

📰 AI Insights

• Listen to Ilya Sutskever’s predictions (former OpenAI Chief Scientist) for the next chapter of AI.

• New data from Carta shows non-AI startups struggle more than AI startups to raise money at high valuations.

• A Qualtrics report reveals that 75% of people distrust companies to use AI properly, with AI's overall approval dropping 11% in the past year. Reddit's reaction: "Surprised it’s not higher, honestly."

• Mistral plans to open an office in Silicon Valley to grow its presence in the U.S.

👀 ICYMI

• How to Create a Team That Owns Every Outcome (Listen or read Link)

• How to Build Emotional Resilience (Listen or read Link)

• The 5 Levels of AI Agent for Autonomy (Listen or read Link)

Bottom-Up Planning: A Necessary Evil?

Why should I care?

In This Is Us movie, Rebecca Pearson forgets cupcakes for her kids’ school event, buys some last minute, and makes them look homemade.

It’s a relatable moment about everyday decision tradeoffs.

As a parent, I make trade-offs too. Meals aren’t always ideal, but my kids know they’re loved—that’s non-negotiable.

Work is no different!

Product leaders often face constraints that force us to adjust plans.

Roadmap planning, for example, should ideally align with company strategy, but tight deadlines or a fast-paced environment don’t always allow it.

Even when time is short, focus on essentials. A bottom-up approach, paired with strategy, ensures you deliver meaningful results.

Use a simple three-step process to keep delivering user value for every release when time is limited.

Let’s dive in.

1- The Five Whys, reimagined at feature level

You’ve probably heard of the "five whys." It’s a problem-solving method where you ask "why" repeatedly—usually five times—until you uncover the root cause.

It’s a powerful way to ensure you’re tackling the real issue, not just the symptoms.

In product management, we often use this technique to dig deeper into requests from customers or stakeholders.

They might talk in terms of features, but it’s our job to understand the underlying problem they’re trying to solve.

But here’s a twist: use the five whys on yourself when planning.

Think about the initiatives you’re considering for next year.

For each one, ask yourself why it’s on the list. Then ask why again. Keep going—five times or until you hit something fundamental to your strategy.

Here’s an example:

• We need to add a new security layer.

• Why? Because security is core to our product.

• Why now? Customers have started asking for it.

• Why are they asking? They’re becoming more focused on security.

• Why is that? We recently expanded into healthcare, where security is critical.

• Why healthcare? It’s a strategic market we’ve decided to target.

This process clarifies priorities and gives better context for each feature on your roadmap.

Try it with your plans—it can help ensure your strategy stays sharp and focused.

2- Focus on the bigger picture

The five whys help you shift focus from features to the reasons behind them.

While it’s not as strategic as starting from goals, it’s a solid way to plan when working bottom-up.

Once you’ve uncovered the reasons, it’s time to organize them.

Group your features into broader initiatives that connect to these reasons, not just outputs. You’ll likely notice overlap—use that to your advantage.

For example, in the earlier case of the healthcare opportunity, you might find other features tied to it. Even if a feature aligns with another reason, like "supporting the company’s vision," if healthcare drove its priority, group it under that initiative.

Being pragmatic here creates a more cohesive plan.

Aim to align everything under 3–5 major initiatives or themes. If you have more, combine them by asking "why" again, but this time, focus on the reasons.

For example, if you see "removing sales barriers" and "shortening onboarding time," those could roll up into a bigger goal like "scaling our sales process."

This grouping simplifies communication and ensures your plan has strategic clarity and focus.