Top 20 Questions to Ask Your Boss—Backed by The Predictive Index

Whether you’re stepping into a new role, joining a fresh team, or just aiming to build a stronger relationship with your current leader, asking great questions is key. Not only does it show initiative and emotional intelligence, but it also sets the foundation for trust, collaboration, and long-term growth.

That said, not all questions are created equal.

Some questions clarify expectations. Some help you get noticed. And others? They reveal your boss’s true leadership style—especially when they’re informed by behavioral science, like The Predictive Index, delivered in Canada by Predictive Success.

In this post, we’ll walk through the top 20 questions to ask your boss—broken down into smart, fun, and strategic categories—and show you how aligning these questions with your manager’s PI profile can give you a serious edge.

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Why Ask Questions Based on The Predictive Index?

At its core, The Predictive Index is about understanding people: how they think, communicate, make decisions, and lead. The PI Behavioral Assessment identifies four key behavioral drives—Dominance, Extraversion, Patience, and Formality—that shape how a person works and interacts with others.

Delivered by Predictive Success, the Predictive Index helps organizations across Canada hire smarter, engage teams better, and unlock leadership potential. But it’s not just a tool for HR. When you, as an employee, understand your boss’s behavioral tendencies, you can adapt your communication style, anticipate their needs, and align your efforts with what they value most.

Let’s dive into the questions—and the science behind why they matter.

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🔍 SMART Questions to Ask Your New Boss

When you’re new to a role or team, showing curiosity and alignment early on is essential. These smart questions to ask your new boss will help you understand expectations, communication preferences, and how to succeed under their leadership.

1. What does success look like in this role after 30, 60, and 90 days?

This question shows your goal-oriented mindset and eagerness to deliver results fast. If your boss scores high in Dominance on the PI spectrum, they’ll appreciate your direct, results-driven approach.

2. How do you prefer to communicate—email, Slack, face-to-face, or something else?

Everyone has a communication preference. Bosses with high Extraversion may prefer in-person chats, while those lower on the scale might opt for written updates.

3. What are the biggest challenges our team is facing right now?

Asking this shows strategic thinking and empathy. It also helps you spot opportunities to contribute early.

4. How do you prefer to give and receive feedback?

Bosses with high Formality appreciate structured feedback cycles. Those with lower Formality may prefer informal, in-the-moment chats.

5. What are your key priorities this quarter, and how can I help move them forward?

This positions you as a team player who’s already thinking beyond your own tasks. It aligns perfectly with the Predictive Index’s philosophy of talent optimization—ensuring people are in roles where they can help achieve business goals.

6. What does your ideal team dynamic look like?

This question gets at your boss’s leadership style. Some prefer close collaboration (think high Extraversion, low Dominance), while others favor independence and accountability.

7. Is there anything that has surprised you about people in this role—either good or bad?

You’ll gain valuable insights into common missteps and standout behaviors.

8. How can I support you in making your job easier?

This one’s a game-changer. Bosses with high Dominance or Patience will see this as a sign that you’re proactive and trustworthy.

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😄 FUN Questions to Ask Your New Boss

Work is serious—but relationships are built on authenticity and connection. These fun questions to ask your new boss break the ice and create memorable, human moments.

9. What was your first-ever job? What did you learn from it?

Great for storytelling and seeing what values shaped them early on.

10. If you weren’t in this job, what would you be doing instead?

Reveals interests and motivations beyond the job title.

11. What’s your favorite part of the workday?

If they say “morning strategy sessions,” maybe you prioritize important questions in the a.m. If it’s “brainstorming with the team,” lean into collaborative moments.

12. Is there a book, movie, or show that really speaks to how you lead?

This can be hilarious, insightful, or both. (We once heard a boss say Ted Lasso, another said Succession—very different vibes!)

13. What’s something on your bucket list?

These conversations go a long way toward building real rapport—and might even spark some shared interests.

14. Any guilty pleasure songs or snacks during the workday?

Lighthearted, personal, and a great way to bond over coffee breaks or music playlists.

15. What’s the most unexpected lesson you’ve learned as a leader?

Fun with a touch of depth. You’ll gain wisdom and insight into what shaped their leadership philosophy.

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💡 STRATEGIC Questions to Ask Based on The Predictive Index

Now let’s level up. These strategic questions reflect a deep understanding of workplace psychology—specifically, behavioral data provided by The Predictive Index. These help you predict how your boss thinks and operates.

16. How do you typically make decisions—gut feeling, data, consensus?

This maps to the Dominance and Formality drives. High-A, low-D bosses may make fast, intuitive decisions. High-D leaders might expect detailed analysis.

17. When something goes wrong, how do you prefer to hear about it?

Timing and tone matter. A boss with high Patience might prefer calm, detailed breakdowns. A fast-paced leader may want the headlines first, then details later.

18. What types of updates do you find most helpful: big-picture strategy, task-level check-ins, or something in between?

Match your reporting style to theirs, and you’ll build trust faster than most.

19. How do you measure success for the team and individuals?

Uncovers what metrics or behaviors they truly value—be it innovation, output, collaboration, or efficiency.

20. What does career growth look like on this team—and what earns m

ore responsibility?

A powerful, forward-looking question. If your manager is a Venturer or Captain on the PI profile (high-D, high-E), they’ll love your ambition and initiative.

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🔁 How to Use The Predictive Index to Your Advantage

Understanding your own PI profile and that of your manager can transform your work dynamic. If your organization uses PI through Predictive Success, request a copy of both profiles (yours and your boss’s). Study how their behavioral drives align—or clash—with yours.

Here’s a quick cheat sheet:

PI Profile	Manager’s Style	Best Questioning Approach
Captain / Maverick	Fast-paced, results-driven	Ask about goals, big wins, and autonomy
Analyzer / Specialist	Detail-oriented, cautious	Ask for clarity, structure, and expectations
Promoter / Collaborator	Social, persuasive, high-energy	Use open-ended, conversational questions
Operator / Guardian	Reliable, consistent, calm	Focus on process, predictability, and timelines

When you frame questions with these tendencies in mind, your conversations will land better, feel smoother, and produce more productive results.

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Final Thoughts: Curiosity + Behavioral Insight = Career Power

Whether you’re a new hire or a seasoned employee looking to strengthen your relationship with leadership, asking the right questions is one of the smartest things you can do.

But when you pair curiosity with science—like The Predictive Index—you move beyond “smart questions” into the realm of strategic influence. You start communicating in a way that resonates with your boss’s behavioral makeup. And that’s how trust is built.

So whether you’re asking about feedback loops, work styles, or favorite snacks—every question is a chance to understand your boss better, perform at a higher level, and build a career that aligns with who you are.

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Want to learn how to bring Predictive Index insights into your own team?

Check out Predictive Success for team-building workshops, leadership development, and custom assessments that will help you and your team work better—together.

Because great teams don’t just happen—they’re designed.