To succeed in your role, you need to understand what truly matters to your manager. But many leaders struggle to communicate their priorities clearly. Instead of waiting for direction, you can ask them smart questions to not only decode what they need, but also to position yourself as a strategic partner. Here’s where to start.

What goals do you discuss with your boss? This reveals what drives their performance reviews and decision-making. Listen for key metrics, repeated themes, and unexpected priorities—you may discover areas where your work has a bigger impact than you realized.

What keeps you up at night about our team or projects?Unlike asking about general challenges, this invites vulnerability and honest insight. It helps you anticipate risks, proactively solve problems, and position yourself as someone who alleviates stress—rather than adds to it.

What actions or changes would make the biggest difference in 90 days? The timeframe forces focus. If their answer is vague, follow up with: “What’s one specific change we could make to achieve that?” If they’re unsure, offer options to guide their thinking.
This tip is adapted from “7 Questions to Decode Your Manager’s Priorities,” by Melody Wilding.
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