Whether you're evaluating a CFO, VP, or Operations leader, the quality of your direct manager determines culture, clarity, accountability, and ultimately, your career trajectory. Yet many professionals hesitate to ask deeper questions out of fear they’ll appear confrontational or reduce their chances of receiving an offer.
The reality?
Top companies respect candidates who evaluate leadership thoughtfully and intentionally.
Below are high-impact questions that help you assess a hiring manager’s leadership style, team culture, and approach to developing people.
Why You Should Interview Your Future Manager
Interviewing your boss gives you valuable insight into:
You're not just accepting a role, you’re accepting a leader and that choice matters.
Questions to Ask a Hiring Manager in an Interview
1. “Have you had to let anyone go from your team? If so, what led to that decision?”
This reveals:
A strong leader gives clear criteria, not vague stories.
2. “Who are you grooming to take your spot?”
This question surfaces:
Good leaders have an answer. Weak ones don’t.
3. “How do you handle feedback from your team? Can you share an example from the last six months?”
This uncovers:
You’re assessing whether this is a leader who listens, or one who steamrolls.
What These Answers Reveal About Leadership Style
Each of these questions gives you clarity around:
This is how seasoned executives avoid landing under a toxic or absent leader.
Final Thoughts
Every interview is a two-way evaluation.
You’re not just interviewing for a job, you’re evaluating a leader who will shape your professional growth.
By using intentional questions and taking note of how a manager responds, you walk into offers with confidence and into roles that align with your long-term goals.
If you're preparing for an executive job search or navigating multiple interview processes, ONWARD Headhunting helps candidates assess leadership, culture fit, and career trajectory with clarity and confidence.