Unlock Potential with 70 Insightful Questions for Leadership Development

Imagine you're on a treasure hunt. Potential is buried deep within every team member, manager, and leader. But you need a map. The problem? Most of us don't have it. Enter the realm of powerful, probing questions designed to dig deep.

Good leadership development questions are the golden keys that unlock hidden potential and guide your leaders toward a motivating development path and enhanced efficiency. 

This article will:

• Give you a list of 70 leadership development questions to nurture growth. 
• Show you why you should be asking those questions in the first place. 

🤔 The art of asking: A catalyst for leadership development conversations

A study conducted by Google found that an essential quality for success was not the brilliance of individuals but the psychological safety of their environment. Specifically, an environment that encouraged employees to win big and take risks without fear of reprisal. 

This safety can be found in open dialogue initiated with thoughtfully asked questions in your workplace. 

It is key to ask the right questions and to ease your leaders into the whole process of answering well. 

💡 You don't want to scare your leaders off or make them feel guilty for not having perfect, intelligent answers right from the very start. 

Answering these questions and developing a growth plan is an ongoing, adaptable process, and it's essential that you guide your leaders along the way. 

👀 To use these questions effectively, follow our guide to creating leadership development plans. For extra help, check these leadership plan examples - you can draw a lot of inspiration for your own processes. 

❓ 70 Questions for leadership development

Here are 70 situation-based questions that activate introspective thinking. Each group of questions comes with explanations of what insight these questions offer. 

Growth conversation starters

Describe a moment where you truly felt your growth was being realized.

Context: Personal growth is often accompanied by moments of epiphany or realization. This prompt encourages sharing such pivotal moments.

Share a hurdle you've faced and how it has influenced your growth trajectory.

Context: Every leader faces hurdles. Discussing them offers a platform to share lessons learned and showcase resilience.

Discuss a time when feedback significantly impacted your development.

Context: Feedback, both positive and constructive, plays a pivotal role in personal growth. This starter aims to delve into the transformative power of feedback.

What accomplishment in the last six months makes you the proudest?"

Context: This question is designed to make individuals reflect on their recent journey. It asks them to sift through their actions and pinpoint a significant moment of achievement.

These conversation starters are crafted to initiate deep reflections and open discussions and foster a supportive environment where leaders can learn from each other's experiences.

Exploring leadership perspectives

1. In a rapidly evolving business landscape, how would you redefine leadership?
2. Share an example of when your unique leadership approach led to an unexpected positive outcome. 
3. What are some non-negotiables in your leadership values? 
4. What would you ask if you could have a conversation with a leader you admire? 

These questions look at how a leader handles change and understands their own impact.

Essentially, they offer a panoramic view of a leader's core skills: adaptability, influence, and inspiration.

These are relatively broad and easier to answer. You could start with these to make your leaders comfortable thinking creatively without getting too specific. 

Fostering self-growth

💡 When discussing self-growth, we recommend tailoring your questions to your leadership competency model. Leadership competencies can give a holistic view of a leader's development.

Name a leadership strength you recently discovered in a high-pressure situation.

This question digs into how a leader responds to unforeseen challenges. ‍

Targeted competency: managing crises and adapting to new situations.

What's a leadership trait you wish to refine, and how do you plan to do it? 

This question assesses the leader's self-awareness about their weaknesses and commitment to self-improvement.

Targeted competency: continuous learning. 

Recount a leadership decision that, in hindsight, taught you a priceless lesson.

Every decision has outcomes, and this question evaluates a leader's competency in making decisions and, more importantly, 

Targeted competency: the ability to reflect on decisions and learn from them.

When faced with leadership stress, what's your go-to strategy?

Leaders who can manage their emotions and stress influence their teams positively. 

Targeted competency: emotional intelligence and handling stressful situations.

What is your leadership style?

 Leadership style is often about how a leader interacts, communicates, and motivates their team.

Targeted competency: interpersonal skills and effective communication.

Incorporating leadership competencies into these questions provides a structured way to evaluate answers and aligns the responses with the organizational expectations of a leader's skills and behaviors. This alignment can guide training, professional development, and future leadership strategies.

Goal resetting

Goal resetting is crucial because it allows individuals to reassess their direction, prioritize tasks, and ensure alignment with changing circumstances or newfound insights. 

• Given your reflections, are there any development goals you'd set differently now?
• How do you envision recalibrating your leadership growth plan for the remainder of the year?
• How do your current achievements and setbacks align with your original expectations, and how might this insight reshape your goals?
• Considering the resources and support available now that weren't when you first set your goals, how would you modify your objectives?
• In light of what you know now, which goals would you prioritize, which would you modify, and which might you set aside for the time being?

Goal resetting questions are vital as they promote adaptability, resourcefulness, and resilience. They allow individuals to remain proactive and agile in their growth journey, ensuring they are always on the most effective path toward their objectives.

Building communication and relationships

1. How do you foster an atmosphere where every team member feels their voice matters? 
2. Describe a situation where your mediation resolved a budding conflict within your team. 
3. What unique actions have you taken to create a culture of trust within your team?
4. How did a piece of feedback from your team change your leadership approach? 
5. What initiatives have you implemented to build a positive and inclusive team culture?

These questions examine how a leader manages team issues like communication, conflict, and trust. 

They also show if the leader listens to constructive feedback and helps everyone get along, keeping the team strong.

Championing vision and strategy

1. Paint a picture of the future you envision for our team.
2. How do you ensure each team member's goals are in harmony with the larger organizational vision?
3. Describe a risk-heavy decision you made and how you managed the potential downsides. 
4. What's one strategy you've adopted to spur innovation within your team?
5. Which unconventional performance indicators do you use to track team progress?

In strategy meetings, include questions that make leaders define their vision and make it fit with the organization's goals. These questions focus on a leader's ability to think strategically and innovatively. 

They look at how well a leader can create and share a strong vision, align team goals with bigger objectives, make tough decisions, encourage creativity, and use different ways to track progress.

Promoting succession planning and leadership development

1. If your successor were to take over tomorrow, what skills would they have?
2. Tell me about a time you helped a future leader's career.
3. How would you teach someone to do your job?
4. What makes a good future leader?
5. How do you make your team better at leading?

These questions help you understand how ready your leader is to train the next leader. They also show how leaders think about helping others grow into leadership roles.

Next steps? Use what you learn from these answers to make better training programs for more effective leaders.

For example, if a boss emphasizes that problem-solving is crucial, you could set up workshops or training sessions focused on decision-making and creative thinking. That way, you directly address what leaders believe is essential, strengthening the next set of leaders.

Boosting diversity and inclusion

1. How did you add diversity to your team?
2. Describe a project you led to make things more inclusive.
3. How do you tackle biases that might exist within your team?
4. How do you encourage open communication?
5. How do you adapt your leadership to different team members?

Based on the answers, consider hosting team-building exercises celebrating diversity or a Lunch & Learn series featuring speakers on topics like unconscious bias or cultural sensitivity. 

If a leader talks about the importance of open dialogue, set up a regular team meeting dedicated solely to discussing diversity and inclusion issues. This way, you're not just listening to leadership but actively responding to their valuable insights.

Handling failures and challenges

1. Share a setback that reshaped your leadership philosophy.
2. How do you keep the team's spirits up during challenging times?
3. Tell me about a hard choice you had to make as a leader quickly.
4. How do you turn team mistakes into learning moments?
5. How do you balance leading and working with your team in tough times?

These questions show how flexible a leader is when plans fail. They also help you see how a leader helps their team stay positive and learn from mistakes. 

If a leader stresses the value of communication during hard times, consider creating clear guidelines for communicating during crises. 

If a leader mentions learning from failures, put together 'failure post-mortems' where the team can openly discuss what went wrong and how to improve. 

Enhancing employee engagement and growth

1. How do you celebrate big wins with your team?
2. What's your secret for keeping everyone engaged?
3. How do you help your team members achieve their career goals?
4. Tell me about how you handle team members who aren't performing well.
5. How do you make learning a regular part of your team's workday?

These questions focus on how a leader keeps their team motivated and helps underperforming team members improve. 

Let's say a leader talks about using team lunches to celebrate wins. You could use this input to create a 'team lunch fund' that teams can tap into when they hit milestones. 

If a leader mentions that career growth is a priority, consider setting up regular one-on-one career chats between team members and their managers. 

Boosting customer orientation

1. How do you get your team to really care about customers?
2. Tell me about a time you used customer feedback to make a significant change.
3. How do you handle a really unhappy customer?
4. How does your team know if they are meeting customer expectations?
5. Can you share a story about turning a customer complaint into something good?

These questions help you understand how a leader ensures their team always has the customer in mind. Their answers reveal how leaders use customer feedback to make improvements and how they handle situations where things go south with a customer.

If a leader stresses the importance of resolving customer complaints quickly, you could look into training sessions on effective complaint resolution. That is an added benefit of asking the right questions – to take what works for them and see if it can benefit the whole organization.

Enabling innovation and creativity

1. How do you get your team to think outside the box?
2. Tell me about an idea that your team came up with that had a huge impact.
3. Do you give your team what they need when they want to try new things?

These questions help you see how natural leaders help their team get creative, if at all. Is your leader enabling innovation, even when success is not guaranteed? 

Fostering work-life balance and well-being

1. Is anyone on your team frequently burnt out? How do you help with this?
2. Any cool stuff you've started to keep your team healthy?

These questions show if the leader prioritizes long-term health over getting the job done – which they should.

They also tell you if the leader is alert and steps in when someone is stressed or if they have specific ways to keep the team healthy.

Navigating through change

1. Have you ever changed a policy or an outdated rule at work?
2. How do you help your team deal with change (e.g., budget cuts, new management)?
3. How do you ensure your team is okay when things are not so okay? 

The economy going south, industry priorities shifting—a lot can happen in corporate. 

Is your leader good at talking people through these changes and providing actionable solutions? 

Stories of past changes they've led will be highly revealing: how they handle tricky situations demonstrates their leadership skills.

The way they talk to their team about changes can say a lot, too. 

Are they straight-up and clear, or does their team end up confused? 

And then, of course, how they look out for their team during turbulent times gives you a peek into their leadership styles.

Leadership coaching

1. How do you know when someone on your team is struggling? 
2. Do you have any stories about how your coaching helped a team member do better?
3. How do you fit coaching into your already busy schedule?
4. Have you ever run into problems when you're trying to coach someone? How'd you handle it?

These questions help you determine if a person in a leadership position spots employees who need extra guidance and what their go-to techniques are for helping them out.

Suppose they've got a good story about coaching making a real difference. In that case, that's a great sign their methods work and that professional development for others is their priority.

We also see how good leaders juggle coaching with everything else they have to do and what they do when coaching gets tough.

⚠️ Are your leaders falling short on the coaching skills front? Then, it's time to invest in coaching skills training.

Thought-provoking leadership questions

1. How do you keep your team always learning and growing?
2. What's the gutsiest decision you've made as a leader?
3. How do you ensure you're not cramping your team's creative style?
4. Fast forward ten years: What do you think makes a great leader then?
5. Got any do-overs in mind? 

These questions nudge your team leader to ponder the bigger picture, like how they're prepping their team for the future or how they handle risky decisions. These aren't yes-or-no questions; they need real thought and invite meaningful conversations.

You could also get fresh ideas for your teams based on the answers.

❓ For more questions to include in a performance review, check out our article on feedback questions for leadership.

💡 6 Tips for using questions for leadership development

Knowing when, how, and where to pose these queries optimizes their impact. Here, we offer practical tips to leverage these questions.

Customize to context

Every individual and situation is unique. Tailor your questions to the specific context. If you're debriefing after a project, "What did you learn from this leadership challenge?" might be fitting. But during annual reviews, a more overarching question like, "What can you do to become a better leader this year?" could be more relevant.

Leverage one-on-one meetings

Personalized attention makes people feel valued. Use one-on-one meetings to ask deep-dive questions.

For example, "What's holding you back from being the leader you envision?" might be better explored privately.

Foster self-reflection

Leadership development involves self-reflection using these questions.

"How do you define leadership?" or "Which leadership skills would you like to develop?" are perfect for introspective exercises.

Use them in group workshops

Use questions to spark group discussions.

Ask questions like "What critical skills need to be honed for our current growth strategy?" or "What kind of culture would you like to create within your team?".

Remember the timing

Timing is crucial. Ask questions when the person is most receptive. A question about skills learned may be best asked after a project's completion.

Encourage open-ended responses

Steer clear of 'yes' or 'no' answers. Ask specific questions that require a bit of thinking and more elaborate answers. This doesn't mean you over-complicate anything.

You create an environment where instead of asking, "Did you finish the project?" you ask, "What challenges did you face in finishing the project?".

➡️ Grow your leaders with Zavvy

Looking to step up your leadership game? 

Our employee enablement software is specifically designed to help you ask thought-provoking and actionable leadership questions. Here's how:

• ❓ Tailor your questions based on clear competencies for every role. 
• 🔁 Leverage competency-based 360 feedback to focus your questions on specific skills or development areas.
• 💬 Align managers and employees in productive and focused one-on-ones.
• 🧮 Use our skill matrices to pinpoint where your leadership questions can be most impactful, whether building on strengths or identifying weaknesses.
• 🌱 Create development action plans based on solid data.
• 🎯 Manage goals for your managers and their teams and keep track of manager effectiveness.

📆 Book a demo today.