Ask These Questions to Align with Your Boss

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.

What do you wish you had more time to work on? This uncovers the work that’s important to your manager that keeps getting pushed aside by more urgent tasks. Look for opportunities to take on these high-value tasks to lighten their load while developing skills that benefit your career.

What does good performance look like? Great performance? Let them define the baseline first, then dig deeper to determine what they value most in an employee.

What emerging trends should we be mindful of? Your boss hears conversations and sees data you don’t. Understanding upcoming shifts in company strategy or industry trends positions you well to anticipate change and adapt.

How does [a particular task] compare to my other responsibilities? This question can kick off a conversation to clarify why certain priorities rise to the top while others get put on the back burner. Should you need to set boundaries, this has the added benefit of making your boss aware of your bandwidth—without sounding like you’re complaining.

Read the article: “7 Questions to Decode Your Manager’s Priorities,” by Melody Wilding.

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