The cost of a poor leadership hire extends far beyond financial implications, affecting team culture, productivity, and organizational momentum. This isn’t a rare occurrence either—40-60% of external executive hires fail within their first 18 months, representing a significant risk to any organization making leadership decisions.
The challenge is to identify candidates who have mastered the interview process but lack genuine leadership capabilities. While traditional interviews often elicit rehearsed responses, behavioral questions requiring specific examples can reveal a candidate’s true leadership competence, both technically and emotionally. This approach helps distinguish between candidates who simply interview well and those who will actually lead well.
Why Traditional Interview Questions Fall Short
Standard interview questions often invite rehearsed, generic responses that sound impressive but lack substance. Candidates come prepared with polished answers to predictable questions like “What’s your leadership style?” or “What are your strengths and weaknesses?” – responses that reveal little about their actual capabilities.
Behavioral interviewing changes this dynamic by forcing candidates to provide specific examples of past leadership experiences. This approach is grounded in the principle that past behavior is the best predictor of future performance. By requiring detailed accounts of real situations, you can better assess how candidates actually lead, rather than how they theorize about leadership.
Question #1 – Measuring Success and Collaboration
“Tell me about a recent success story at work you were directly involved in. What made it a success? What role did you/others play?”
This question reveals how candidates define and measure success through meaningful metrics or vague outcomes. Listen for how they balance discussing their involvement while acknowledging team efforts. Effective leaders clearly articulate their specific role while giving appropriate credit to others, demonstrating strategic thinking and collaborative spirit.
Red Flags to Watch For:
- Taking full credit for team achievements
- Providing only vague descriptions of their input
- Inability to clearly articulate what made the initiative successful
- No mention of measurable results or impact
Pro Tip: Keep success questions open-ended to see how candidates naturally address their responsibilities and others’. Check whether they share credit and demonstrate how they gathered resources and solved problems.
Question #2 – Learning from Setbacks
“Tell me about a recent situation that did not turn out so well that you were directly involved in. Why didn’t it work out? What role did you/others play?”
Evaluating how candidates respond to failure often reveals more than their successes. Observe for appropriate accountability balanced with fair assessment—strong leaders own their part in failures without unfairly blaming others. Pay attention to whether they provide specific lessons learned from the experience and how they’ve implemented changes since. Their explanation of the problem-solving process, even during unsuccessful ventures, offers valuable insight into their leadership approach.
Red Flags to Watch For:
- Blaming others without acknowledging personal responsibility
- Defensiveness or inability to admit mistakes
- No meaningful learning or growth from the experience
- Vague descriptions that avoid specific details about the situation
Question #3 – Self-Awareness and Growth
“What feedback have you gotten from others about your leadership style–both the pros and the cons? You can think in terms of supervisors, peers, and direct reports.”
This question functions as a mini-360 assessment, revealing the candidate’s level of self-awareness. Exceptional responses include balanced examples from various stakeholders—bosses, colleagues, and team members—along with concrete steps they’ve taken to address development areas. The most self-aware leaders recognize how others experience their leadership and can speak candidly about both strengths and growth opportunities.
Red Flags to Watch For:
- Inability to articulate any weaknesses or development areas
- Dismissing or rationalizing critical feedback
- Vague generalities rather than specific examples
- Feedback limited to only one perspective (e.g., only from supervisors)
Pro Tip: Note whether candidates voluntarily mention feedback from different levels (supervisors, peers, and direct reports). Leaders with true self-awareness understand how they’re perceived across the organization, not just by their bosses.
Question #4 – Handling Difficult Decisions
“Tell me about a time you had to make a difficult decision that wasn’t popular. How did you handle the communication and emotions around it?”
Unpopular decisions separate true leaders from people-pleasers. When exploring this question, focus on the candidate’s thought process behind challenging choices and how they managed the aftermath. Top performers demonstrate transparent communication and genuine empathy, balancing business needs with people sensitivity. How they navigated emotional responses and maintained team cohesion despite disagreement offers critical insight into their leadership maturity.
Red Flags to Watch For:
- Avoidance of difficult conversations or necessary confrontation
- Insensitivity to emotional impact on team members
- Poor change management or communication strategy
- Prioritizing popularity over necessary but unpopular decisions
Question #5 – Creating Psychological Safety
“What strategies do you use to create psychological safety within your team?”
The concept of team trust has become central to high-performing teams, and for good reason—teams that feel safe taking risks and being vulnerable with each other consistently outperform others. Listen for the candidate’s familiarity with psychological safety beyond theoretical knowledge. Strong leaders describe specific techniques they’ve implemented to encourage speaking up, constructively manage mistakes, and create inclusive environments where diverse perspectives thrive. Their examples should demonstrate how they’ve built cultures where team members feel safe taking risks.
Red Flags to Watch For:
- Unfamiliarity with the concept of psychological safety
- Authoritarian or rigid leadership tendencies
- Vague platitudes without actionable strategies
- No concrete examples of encouraging vulnerability or risk-taking
Question #6 – Openness to New Perspectives
“When was the last time you changed your mind on something important because of someone else’s perspective? What happened?”
Intellectual humility distinguishes exceptional leaders from merely competent ones. This question uncovers whether a candidate values input from others or maintains rigid thinking patterns. The strongest responses include specific examples of meaningful perspective shifts—not just superficial adjustments but genuine reconsideration of views. Notice how they integrated this learning into their leadership approach and whether they acknowledge the value of being open to alternative viewpoints.
Red Flags to Watch For:
- Inability to recall instances of changing their mind
- Defensiveness about being wrong or challenged
- Only superficial or inconsequential adjustments mentioned
- Taking credit for others’ ideas after initial resistance
Pro Tip: Look for answers that demonstrate genuine openness to other viewpoints and the ability to evolve their thinking based on new information or perspectives from team members.
Question #7 – Conflict Resolution Skills
“Describe a situation where you had to navigate conflict between team members. How did you approach it?”
Complex team dynamics inevitably lead to conflict, making resolution skills essential for effective leadership. This question reveals a candidate’s approach to balancing competing interests while maintaining fairness and respect for all parties involved. The best leaders address underlying issues rather than implementing superficial quick fixes, demonstrating emotional intelligence throughout the process. Their conflict management strategies should show how they transform disagreements into opportunities for team growth and stronger relationships.
Red Flags to Watch For:
- Conflict avoidance or sweeping issues under the rug
- Showing favoritism or taking sides inappropriately
- Resorting to authoritarian solutions without dialogue
- Lack of established strategies for addressing team tension
Evaluating Responses – Reading Between the Lines
Effective assessment of leadership candidates requires looking beyond their initial answers to what’s truly being communicated. When responses seem vague or rehearsed, probe deeper with targeted follow-up questions while paying attention to nonverbal cues that often reveal more than words alone. A particularly revealing strategy involves asking candidates to write a one-page description of the role they’ve applied for—this exercise quickly identifies misalignment between their understanding and your requirements, providing insight that balances your intuition with objective evaluation criteria.
Pro Tip: At the end of the interview, ask the candidate to write a one-page description of the role they’ve applied for. At the leadership level, if they don’t write something that matches your sense of the role, that’s a significant red flag.
Final Thoughts: Finding Your Next Great Leader
Leadership hiring decisions have far-reaching implications beyond simply filling a position. The seven questions outlined above provide a framework for identifying authentic leaders who balance results orientation with strong people skills. While no interview process is foolproof, these behavioral questions help distinguish between candidates who interview well and those who will actually lead well when facing real challenges. By integrating these questions into your comprehensive assessment strategy, you’ll significantly increase your chances of finding exceptional leaders who drive sustainable success.
Ready to build stronger leadership in your organization? Explore our Leadership Development page for expert resources and programs designed to help you identify and develop truly exceptional leaders!