Product leaders often feel they must present a perfect, unassailable plan to executives. However, the goal should be to start a discussion. Presenting an idea as an educated guess allows for a collaborative debate where you can gather more information and adjust the strategy based on leadership's feedback.

Don't just accept tasks from your boss. The initial request often reflects habit, not strategy. Your primary role is to pause and question if the proposed task truly solves the underlying business problem. This critical step prevents wasted effort and aligns work with actual goals, even when it means challenging a superior's directive.

When working under a less-experienced manager, you must take the lead in defining the relationship. Proactively push for clear goals, establish a check-in cadence, and ask for the feedback you need. In essence, you are teaching them how to be the manager you require.

Leaders set direction from a strategic vantage point but lack visibility into on-the-ground realities. It is your responsibility as an individual contributor to proactively communicate unforeseen challenges and propose better paths based on what you encounter directly.

Many 1-on-1s become rote reviews of past work. A more effective approach is to dedicate significant time to discussing future plans. Use this opportunity to check in on upcoming goals and direction, ensuring you and your manager are aligned before work begins.

To move from execution to strategy, stop waiting for permission or a promotion. Proactively demonstrate strategic thinking in your current role. Instead of just reporting what you did, frame your updates as "This is what I think we should do and why."

To gain the freedom to lead your own way, first ask your manager to define success. Then, confirm your understanding by repeating it back. Finally, frame your request for autonomy as the best method to achieve their stated goals.

When meeting with senior leaders, shift the focus from your status updates to their priorities. Ask what's top of mind for them, what challenges they face, and how you can help. This reframes you from a direct report into a strategic ally, building trust and social capital.

When communicating with executive leaders, always begin with the high-level, strategic view (the "macro") to establish context and alignment. However, you must be prepared to dive into any level of detail ("micro") they ask about. This approach respects their time while demonstrating your comprehensive understanding and credibility.