Discovering the right leader for a team goes beyond a resume; it’s about asking the tough questions that reveal true character and capability. This article delves into critical interview questions designed by leadership experts to unearth the essence of a candidate’s suitability for a team. Gain valuable insights from industry veterans on how to assess potential leaders through a series of thought-provoking inquiries.
- Ask About Handling Unpopular Decisions
- Inquire on Data-Driven Persuasion
- Question on Navigating Tough Decisions
- Probe for Perspective Shifts
- Request a Candidate’s Life Story
- Ask About Leading Through Change
- Inquire About Mentorship Experiences
- Question Handling Disagreements with Boss
- Probe for Learning from Tough Decisions
- Ask About Leadership Philosophy
- Inquire About Handling Costly Mistakes
- Debunk the Silver Bullet Myth
- Question Conflict Resolution Skills
- Ask About Adapting Communication Styles
- Probe for Recognizing Leadership Mistakes
Ask About Handling Unpopular Decisions
One of the most revealing questions I ask potential leadership team members during the interview process is:
“Tell me about a time when you had to make a difficult decision that was unpopular. How did you handle it, and what was the outcome?”
This question is critical because strong leaders must make tough decisions—whether it’s restructuring a team, cutting costs, or changing strategy—often in the face of resistance. The way a candidate answers provides insights into several key leadership qualities:
- Decision-Making Under Pressure: Does the candidate demonstrate logical reasoning and confidence in their choices? Leaders must be able to analyze situations, weigh risks, and take decisive action without hesitation.
- Emotional Intelligence & Communication: Unpopular decisions require clear, empathetic communication to bring the team on board. I look for candidates who show self-awareness, transparency, and the ability to manage pushback professionally.
- Resilience & Accountability: A strong leader owns their decisions—even if they’re difficult. Do they take responsibility for their actions, or do they shift blame?
- Ability to Influence & Inspire: Great leaders don’t just enforce decisions—they gain buy-in by explaining the “why” and addressing concerns. I want to see if the candidate used persuasion, active listening, or compromise to navigate resistance.
Example of a Strong Answer: A candidate once shared how they eliminated a long-standing, underperforming product line despite internal resistance. They outlined how they gathered data, consulted stakeholders, and communicated the financial impact to justify the decision. Although the change was initially met with skepticism, within six months, the company reallocated resources to a more profitable initiative, leading to a 25% increase in revenue.
A vague or defensive response to this question signals hesitation, poor communication, or an inability to handle pressure. A strong answer, on the other hand, reveals a leader who is strategic, emotionally intelligent, and capable of making high-impact decisions—even when they’re difficult.
Margaret Buj
Interview Coach and Talent Acquisition Manager, Mixmax
Inquire on Data-Driven Persuasion
One essential question we always ask potential leadership candidates is, “Tell me about a time when you used data to change someone’s mind.” This question helps us spot leaders who can blend analytical thinking with people skills. We find that strong candidates typically share stories that show how they turned complex information into clear, compelling arguments. The best responses reveal someone who not only understands numbers but knows how to use them to build trust and drive change.
What makes this question so useful is how it reveals multiple layers of a candidate’s abilities. First, it shows us their comfort level with data and their analytical skills. But more importantly, it gives us insight into how they handle disagreement and influence others. We get to see if they can read the room, adjust their approach, and bring people along with them. The stories candidates share often tell us about their emotional intelligence too. Great leaders know that changing minds isn’t just about presenting facts; it’s about understanding and addressing concerns, building relationships, and making others feel heard.
In our experience, the most promising candidates share examples where they didn’t just win an argument but helped build stronger working relationships in the process. These are the kind of leaders who can drive real progress while keeping their teams engaged and motivated.
Julia Yurchak
Talent Sourcing, Acquisition & Management Specialist| Senior Recruitment Consultant, Keller Executive Search
Question on Navigating Tough Decisions
“How do you approach making a difficult decision that may not be popular but is essential for the success of the organization?”
Every executive, at some point, has to make and implement decisions that won’t be well-received—whether due to shareholder expectations, CEO directives, or market-driven necessities. I want to understand how a potential leadership team member navigates these challenges.
For me, as a Managing Director, it’s crucial that leadership listens to their team, acknowledges concerns, and ensures transparency in decision-making. A strong leader doesn’t just enforce a tough decision; they communicate its necessity, explain the reasoning behind it, and help the team understand the bigger picture.
Additionally, I look for a thoughtful approach to decision-making—someone who evaluates the situation from every angle, seeks input from both superiors and team members, asks the right questions, and builds a well-rounded understanding before taking action. The ability to balance strategic thinking with empathy and clear communication is what defines a truly effective leader.
Plamen Nakov
Managing Director, DSS – Digital and Software Solutions
Probe for Perspective Shifts
One key question I always toss to potential leaders is:
“Can you share an experience where you had to radically change your perspective on a core decision—even when you were convinced you were right—and what did that process teach you about leadership?”
It might seem like a simple query, but the answers can be surprisingly revealing. This isn’t just about decision-making skills—it’s about digging into how someone handles being proven wrong, which in turn tells you a lot about their humility, adaptability, and willingness to evolve. A solid answer typically shows:
- Humility: A readiness to admit mistakes and learn from them.
- Adaptability: The ability to pivot when new information challenges your assumptions.
- Self-Awareness: Recognizing personal biases and committing to ongoing growth.
- Balanced Judgment: Blending gut instinct with solid data to guide your team.
I remember early on, I was dead set on a particular product feature I believed was our golden ticket. Then a trusted team member challenged my perspective, and I had to step back and really rethink the approach. That uncomfortable moment not only reshaped our product strategy but also sparked a culture of open dialogue and agile thinking within the team. It drove home the idea that real leadership isn’t about clinging to your convictions at all costs—it’s about being flexible enough to learn from the unexpected.
This question has a knack for unearthing leaders who don’t just strategize on paper but can transform setbacks into growth opportunities. And that quality? It’s pure gold in any team aiming to thrive in today’s fast-paced world.
Derek Pankaew
CEO & Founder, Listening (dot) com
Request a Candidate’s Life Story
Hiring the right people can have a significant impact on the effectiveness and success of a leadership team in achieving the organization’s goals. In nearly 20 years of hiring, I begin all interviews with one prompt that offers many insights into the candidate and it allows me to see how the candidate takes the big idea of telling their life story and boils that down to what is most important. I start each interview by asking, “In 5-10 minutes, tell me your story up until now.”
First, this open-ended question allows the interviewer insight into what the candidate views as important in their story. I listen for whether they focus their answer on achievement and/or learning, people and/or process, success and/or failure, analysis and/or problem solving. I notice which parts of the story they are most excited to share. I also notice if their story is a complete picture, or focused on one aspect of their life, such as their career.
As the candidate shares, I actively listen for who they are in their story. Are they the driver of their story, or are they a victim of circumstances outside their control? I listen for stories of resilience, initiative, curiosity, team-building.
I am also listening for how the candidate includes other people in their story. Do they demonstrate collaboration with others? Do they work better solo? Do they mention times when they have consulted with a mentor, spouse, partner, friend or family member? Do they make big decisions on their own? Do they demonstrate care and gratitude for others?
By starting the interview by asking the candidate to share their story, you are able to assess the candidate’s suitability for the team. During the storytelling, you will notice what gives you confidence that the candidate will work well within the current composition of the team and the organization’s culture, and which aspects of the story you may want to explore more deeply later in the interview. There are many ways to assess an individual’s skills. This simple interview prompt is an excellent way to assess a candidate’s suitability for a position within a leadership team.
Erin Gregg
Svp, The Nebo Company
Ask About Leading Through Change
Choosing the right leaders for a team requires more than just reviewing their experience and credentials. It is important to understand how they tackle challenges, motivate others, and adjust to change. One of the most insightful questions I ask during leadership interviews is, “Can you share an example of a time when you led a team through a major change and what steps did you take to gain their support?”
This question helps evaluate key leadership traits. First, it sheds light on their ability to manage change, a crucial skill in today’s fast-moving work environment. Their response reveals how they deal with uncertainty, overcome resistance, and keep the team focused during transitions. It also highlights their communication skills since effective leaders must clearly share their vision and involve their team in the process.
Beyond communication, this question uncovers their level of emotional intelligence and empathy. Strong leaders recognize the concerns of their team members and actively foster trust and support. Their answer provides insight into whether they prioritize people, seek feedback, and adjust their leadership style to meet the team’s needs.
Finally, their response showcases their problem-solving skills and flexibility. The strategies they describe offer a glimpse into how they analyze situations, make decisions under pressure, and encourage teamwork.
This question does more than assess past experiences. It helps determine if their leadership style matches our culture and values, ensuring they are a good fit for the team.
Nirmal Gyanwali
Founder & CMO, WP Creative
Inquire About Mentorship Experiences
One question I always ask potential leadership team members is: “Tell me about a time you sought out a coach or mentor, and how that experience shaped your leadership approach. Also, how do you currently invest in mentoring others?”
This question helps me identify key leadership qualities like humility, self-awareness, and a commitment to lifelong learning.
Great leaders recognize they don’t have all the answers—they actively seek guidance, feedback, and growth opportunities. Just as importantly, they pay it forward, investing in the development of others. A strong leadership team isn’t just made up of high performers; it’s made up of people who elevate those around them.
If someone struggles to answer this question, it raises a red flag about their willingness to learn and their ability to develop future leaders. The best teams thrive on a culture of growth—”get a coach, be a coach”—always ready to learn more, always lifting as they go. Truly showing that rising tides raise all ships. Now that’s a good leader!
Melanie Booher
Engagement & Experience Officer, Talent Magnet Institute
Question Handling Disagreements with Boss
I like to ask, “Tell me about a time you completely disagreed with your boss—how did you handle it?” It cuts through the fluff and shows me how they think under pressure. Are they a yes-person, or can they push back with logic and tact? Great leaders don’t just follow orders—they challenge ideas, defend their convictions, and know when to compromise. This question reveals their communication skills, emotional intelligence, and whether they can navigate conflict without blowing things up. If they can’t give a solid answer, they’re probably not ready to lead.
Justin Belmont
Founder & CEO, Prose
Probe for Learning from Tough Decisions
“Tell me a time when you had to make a tough decision that didn’t turn out as planned—how did you bounce back from it, and what did you learn?” This is my go-to question when interviewing potential leadership candidates.
This question enables me to examine a few very significant things: ownership, adaptability, and resilience. In a fast-changing online learning environment, we need leaders who not only chase perfection but also embrace challenges, learn from failures, and keep pushing.
In most cases, I am mostly looking for someone who owns their mistakes, analyzes them, and grows from them—not someone who deflects blame or sugarcoats failure. If I’m being honest, the best candidates I’ve hired weren’t the ones with spotless records, but the ones who could reflect, pivot, and improve.
We innovate, and innovation means taking risks. I need leaders who are able to lead in uncertainty with confidence and use “failures” as stepping stones to success. Because leadership is not about doing everything right—it’s about making things right.
Vasilii Kiselev
CEO & Co-Founder, Legacy Online School
Ask About Leadership Philosophy
When assisting my clients to find exceptional leaders, my primary objective is to understand how deeply ingrained leadership is in their BEING. The question, “Please tell me about your leadership ethos/philosophy,” is very revealing. The level of confidence with which the candidate answers the question gives me a very good idea of how strongly they identify with being a leader. Beyond identification, I am also looking for individuals who LOVE leading, who are fascinated by people and who delight in facilitating their development and engagement. The more they have owned their leadership identity the more likely they are to be intentional about being and becoming exceptional in the role.
Because behavior stems from our root beliefs, the candidate’s ethos will inform the leadership behaviors we are likely to see. Often the philosophy that a candidate explains is very generic and cliched. Those candidates worry me. It feels as if they are trying to say the right thing. Some responses to this question reveal the candidates’ experience of being led. Great leaders often beget great leaders, but if applicants have had poor role models, I want to hear how they have altered their own approaches to be better than their predecessors.
I am looking for exceptional people who have clearly thought deeply about what it means to lead effectively, who have been influenced by original and progressive thinking on the subject. I am very impressed by those who can articulate the dilemmas and paradoxes that a leader must navigate and I am looking for the ability to translate sound core principles into situational realities.
I am especially averse to leadership behaviors that rely on coercive power, positional authority and generic rules. I am seeking leaders who know how to engage, enroll and grow people—embracing and unleashing their individual strengths and potential. I ideally want to find leaders who understand that leadership is fundamentally about people, who demonstrate that they know how to understand people, who prioritize listening and who are equipped to deal with the complexities and dynamics of human beings and human interaction.
Janet du Preez (MSc MOTI)
Leadership & Organisational Development Consultant, Engagement Dynamics
Inquire About Handling Costly Mistakes
In an interview, I love to ask people, “Tell me about a time you or your team made a costly mistake. What happened, and how did you handle it?” The applicant’s answer to this question will tell you a lot about their personality. If they blame the bad outcome on their coworkers or don’t describe a reasonable resolution process, it could be a sign that they lack leadership skills. On the other hand, if they take responsibility for the outcome and describe a resolution that includes open communications and the creation of systems to reduce the likelihood of future mistakes, it could be an indicator that they are a great hire, worthy of further exploration.
Dennis Consorte
Digital Marketing & Leadership Consultant for Startups, Consorte Marketing
Debunk the Silver Bullet Myth
I’m providing a bit of a “hot take” answer. No one “silver bullet” question exists and trying to find one is reductionistic and ill-advised. Leadership teams are too important to try to have one great question. Leaders should be selected based on a carefully constructed success profile of key competencies, and then they need to be assessed using reliable and valid measures against those competencies.
One small part of that is designing an interview guide with MULTIPLE competency-based questions, but interviewing alone is insufficient. We and our clients who engage us in the selection process use a multi-method approach including a business simulation, leadership styles (personality), and cognitive measures. Stopping short of a robust process designed by human capital professionals is simply going to result in a hit-or-miss approach to success.
Sandy Fiaschetti, Ph.D.
Founder and Managing Partner, Lodestone People Consulting
Question Conflict Resolution Skills
One great way to assess a candidate’s leadership skills during an interview is by asking them to explain a situation where they had to step in and resolve a conflict. It allows recruiters and hiring managers to better understand their critical thinking skills and management style, and see if they were able to make peace within their team successfully. Executive candidates are expected to be strong leaders who can resolve disputes effectively, so asking questions about conflict resolution can help guide the assessment.
Benjamin Farber
President, Bristol Associates, Inc.
Ask About Adapting Communication Styles
A question that has a significant impact on how the interviewee may fit in a multigenerational workplace, and especially in a mid-sized operations, is: “Can you describe if you have had to adapt your communication styles to collaborate effectively with a teammate from a different generation or cultural background?” This question is essential because it reveals the interviewee’s consciousness and sensitivity to the diversity of age and culture, as well as the adaptability and interpersonal skill of the candidate.
Requesting information on an actual situation gives the interviewee a chance to show their knowledge and expertise to unite different age groups, conform communication, and take care of a broad range of people. In addition, a response shows their ability to find answers and to show kindness and sympathy to different kinds of people. The query has affected our choices in people we wanted to hire. It helps us to find the people we need that can not only be able to help with our technical needs, but to bring together different age groups and make a better place to work.
Blake Smith
Marketing Manager, ClockOn
Probe for Recognizing Leadership Mistakes
“What’s one mistake you see leaders making again and again? How do you ensure you don’t make it?”
This question might seem straightforward at first glance, but it holds layers of insight into a leader’s mindset. It’s a trap question for those who aren’t thinking deeply because while it invites the candidate to critique others, it also reveals how they reflect on their own leadership approach. Do they simply list a mistake they’ve seen others make, or do they recognize how they’ve worked to avoid making the same missteps? What this question really uncovers is:
- Pattern recognition: Do you have the ability to spot recurring pitfalls, or do you give a surface-level response without deeper analysis?
- Self-awareness: Do you recognize your own blind spots or do you assume leadership mistakes apply only to others?
- Commitment to growth: Do you learn from observed mistakes and adjust your approach accordingly?
- Adaptability: Do you evolve as challenges arise, or do you hold onto rigid leadership approaches even when they no longer serve the team?
- Leadership philosophy: Do you see leadership as a means of control, or do you focus on influence and engagement to drive results?
- Accountability vs. deflection: Do you take ownership of challenges, or shift blame onto circumstances, teams, or past leaders?
A wrong way to answer such a question would be by simply stating, “Bad leaders micromanage their teams.” At first glance, this seems like a reasonable response. But it’s generic, overused, and lacks personal reflection. The interviewer now knows what you dislike in others, but you haven’t explained how they ensure they don’t fall into the same habit. Worse, it suggests they might not recognize their own tendencies toward control.
A better answer would be, “One mistake I’ve seen leaders make repeatedly is assuming their team understands expectations without clearly defining them. Early in my career, I made this mistake myself, believing that a talented, motivated team would naturally align without needing explicit direction. I quickly learned that clarity is a leader’s responsibility. Now, I make a conscious effort to over-communicate expectations, provide consistent feedback, and ensure alignment at every stage. If something isn’t clear, it’s on me to fix it, not my team to figure out.”
Leadership isn’t about avoiding mistakes; it’s about recognizing them before they happen, taking responsibility when they do, and being humble enough to course-correct.
Sylvie Di Giusto
Keynote Speaker & Author | Helping Professionals Lead Better, Sell Faster, Persuade Instantly, Sylvie di Giusto