Most people think great leaders have all the answers. But that’s not true.
The best leaders ask tough questions — to themselves and to others. They ask because they want to understand, not just to look smart.
When I was young, I believed that smart people always had quick answers. In school, we got high grades for knowing answers, not for asking questions. That’s how we were trained. We learned to stay quiet and wait for someone else to lead.
But when I started leading people, I learned something powerful. Good answers can help you today, but good questions can help you grow for life.
That lesson changed how I lead. Today, when I train leaders and teams across the Philippines, I always tell them:
“You don’t need to know everything. You just need to ask better.”
Every great idea, every strong team, and every brave decision starts with one thing — a tough question.
I’ll show you why asking tough questions can make you a better leader, a better teammate, and a better person.
Why Asking Tough Questions Is Important
Many Filipino leaders believe they must always have the answer. They think people will respect them more if they speak fast and sound sure.
But leadership is not about having all the answers. Leadership is about helping people think, grow, and act with wisdom. And that starts when you learn to ask tough questions — even when it feels uncomfortable.
1. Tough Questions Help You See
When you ask tough questions, you slow down. You take time to understand what is really happening, not just what looks true on the surface.
Sometimes, people rush to fix a problem. They choose the first answer they can think of. But the first answer is not always the best one. A tough question helps you dig deeper. It helps you see the real reason behind a challenge.
For example: Instead of asking, “Who made the mistake?” Ask, “What made this mistake easy to happen?”
That question changes everything. It moves the focus from blaming to learning.
2. Tough Questions Help Your Team Grow
A leader’s job is not to give orders all the time. Your job is to help people think for themselves.
When you ask tough questions, you give your team a chance to lead. You help them find their own answers and build confidence.
Try asking:
“What do you think we should do next?” “What options do you see?” “What’s one small step we can take today?”
When people answer questions like these, they become more responsible. They stop waiting for you — and start owning their work. That’s how leaders create more leaders.
3. Tough Questions Build Trust
Some leaders are afraid to ask because they don’t want to look weak. But the truth is, when you ask with honesty, you build trust.
Your team sees that you care. You are not pretending to know everything. You are learning with them, not above them.
That kind of humility makes people open up. They share ideas, speak honestly, and feel safe. And when people feel safe, they do their best work.
4. Tough Questions Keep You in Learning Mode
Every leader faces pressure. Sometimes, you will feel the need to decide quickly. But when you pause and ask a question, you switch your mind from judging to learning.
Instead of saying, “This is wrong,” you can ask,
“What can we learn from this?” “What’s another way to see this?”
Good leaders never stop learning. And people who never stop learning never stop growing.
A Quick Reflection for You
Think about your last big decision. Did you ask enough questions before deciding? Or did you rush to give answers?
If you want your team to grow, start by changing how you lead. Ask tough questions. Listen deeply. And watch how your people — and you — begin to change.
How to Ask Tough Questions Effectively
Asking tough questions is not easy. Some people get scared when you ask. Others feel defensive. That’s why it matters how you ask.
Good leaders don’t use questions to embarrass people. They use questions to help people think better and grow stronger. Here’s how you can do that.
1. Ask with an Open Mind
The way you ask a question changes the answer you get. If you sound angry or judgmental, people will hide the truth. If you sound curious and kind, they will open up.
Use open questions — the kind that cannot be answered by just “yes” or “no.” These questions often begin with who, what, when, where, why, or how.
For example: ❌ “Did you finish your task?” ✅ “What helped you finish your task?” or “What got in the way?”
Open questions help people explain their thoughts. You learn more. They feel heard.
2. Focus on Learning, Not Blame
When something goes wrong, it’s easy to ask,
“Who made the mistake?”
But that kind of question makes people afraid. They will defend themselves instead of learning.
Try asking:
“What made this mistake happen?” “What can we do better next time?”
These questions create a learning culture. They show that you care more about growth than fault.
3. Be Present and Listen Fully
Good leaders know how to listen. When you ask tough questions, don’t rush the answer. Pause. Look at the person. Nod. Let them finish.
Sometimes silence feels uncomfortable, but silence is powerful. It tells the other person that their answer matters.
Listening is half of asking. If you ask but don’t listen, you only collect words — not wisdom.
4. Ask Appreciative Questions
Don’t only ask what went wrong. Also ask what went right.
Appreciative questions bring energy and hope. They help people see what’s working so they can do more of it.
Ask things like:
“When did our team work really well?” “What made that success possible?” “What can we repeat next time?”
When people talk about what works, they build confidence and motivation.
5. Keep It Simple and Clear
Avoid long, complicated questions. If your question has too many parts, people won’t know where to start.
Ask one question at a time. Keep it short and focused.
Instead of:
“Why do you think the project was delayed, and who was responsible, and what can we do to make sure this never happens again?”
Say:
“What made the project take longer than expected?”
Then listen. After that, ask a follow-up question if needed.
Simple questions often bring the deepest answers.
6. Use the Leadership Question Loop
Here’s a small habit you can start using every day. I call it The Leadership Question Loop.
Ask → Listen → Act.
- Ask: Ask one meaningful question.
- Listen: Truly listen to what people say.
- Act: Take one small step based on what you learned.
Repeat this loop every day. In time, you’ll notice big changes — in how you think, how you lead, and how your team responds.
Try This Now
Before your next meeting, write one tough question you’ve been avoiding. It might be:
“What do my people need that I’m not giving yet?” “What truth am I not facing?”
Ask that question — to yourself, or to your team. Listen. Don’t defend. You might be surprised by what you discover.
The Impact on the Leader and the Team
When you learn to ask tough questions, everything changes. You begin to see people, problems, and possibilities in a new light. It changes how you lead — and how others respond to you.
Let’s look at what happens when leaders make asking questions a daily habit.
1. You Become a More Authentic Leader
Leaders who ask tough questions are not afraid to say,
“I don’t know yet — let’s find out together.”
That honesty builds trust. Your team sees that you are real — not pretending, not proud, just human.
When people see your honesty, they give you honesty in return. They tell you the truth, even when it’s hard. They stop hiding mistakes because they know you care about learning, not blaming.
Asking tough questions also makes you humble. It reminds you that leadership is not about power; it’s about purpose.
2. You Build Stronger, Smarter Teams
When you ask your team for their thoughts, you show them that their voice matters. That simple act builds confidence. They begin to see themselves not just as workers, but as problem solvers and decision makers.
Teams that learn to ask and answer tough questions together become unstoppable. They talk openly. They solve problems faster. They help each other improve.
I’ve seen this many times in workshops across the Philippines — from small schools to big companies. When leaders ask questions like “What can we learn from this?” or “What do you think will work better next time?” the room comes alive. People start thinking. They start owning their work.
That’s when magic happens.
3. You Create a Culture of Learning and Trust
When one leader starts asking better questions, others follow. Soon, it becomes part of the culture.
People stop being afraid to speak up. They share ideas, raise concerns, and learn from mistakes. Instead of saying “That’s not my job,” they start saying, “What can I do to help?”
This is how trust grows — not from big speeches, but from small, honest questions asked every day.
4. You Stay Calm in Tough Situations
Tough situations test every leader. But if you’ve learned to ask tough questions, you stay calm.
Instead of reacting with anger, you can ask,
“What’s really happening here?” “What do we need to understand before we act?”
That short pause makes a big difference. It helps you think clearly and choose wisely.
Good questions protect you from bad decisions.
5. You Inspire Others to Lead
People follow leaders who make them feel seen and heard. When you ask questions, you invite people to grow. You show them that their ideas matter.
Soon, they start doing the same. They ask their own teams questions. They guide others with curiosity and care.
This is how leadership multiplies. Not by control — but by conversation.
A Small Shift That Changes Everything
If you remember one thing from this article, let it be this: Great leaders don’t always have the answers. They have the courage to ask.
When you ask tough questions, you open minds. When you listen, you open hearts. And when you act, you open doors to change.
Leadership starts with one brave question — and that question might just be yours.
Examples of Tough Questions Every Leader Should Ask
It’s one thing to know that leaders must ask tough questions. It’s another thing to actually do it.
Many leaders tell me,
“Sir Jef, I want to ask better questions. But where do I start?”
The good news? You can start anywhere. Below are examples you can use — questions that help you see clearly, build trust, and lead with courage.
A. When You’re Leading Change
Change makes people nervous. But if you ask the right questions, you help your team feel safe and ready.
Try these:
- “What’s worrying you the most about this change?”
- “What part of our work must stay the same?”
- “What would make this change easier for you?”
These questions help you understand people’s feelings before you act. When people feel heard, they help you make the change work.
B. When You’re Improving Performance
It’s not easy to talk about performance. Many leaders avoid these talks because they don’t want to hurt feelings. But avoiding questions won’t help anyone grow.
Ask with kindness, not blame:
- “What part of your work feels hardest right now?”
- “What’s one thing you want to get better at?”
- “What can I do to help you succeed?”
These simple questions open honest conversations. They show care and build confidence.
C. When You’re Planning for the Future
Great leaders think ahead. They don’t just plan tasks — they plan growth.
Ask:
- “What do you want to achieve in the next year?”
- “Where do you see yourself growing next?”
- “What new skill will help our team most?”
These questions help people dream — and connect their dreams to your team’s goals.
D. When You’re Facing Problems or Conflict
Tough times reveal strong leaders. Instead of reacting with blame, respond with curiosity.
Ask:
- “What’s really happening here?”
- “What part of this problem can we fix first?”
- “What can we learn from this situation?”
When you ask calm, curious questions, you turn tension into teamwork.
E. When You’re Reflecting on Yourself
The hardest person to lead is yourself. That’s why self-questioning is part of leadership.
Ask yourself:
- “Am I living a good life?”
- “Am I walking the talk?”
- “What habit do I need to let go of?”
- “Am I proud of the person I’m becoming?”
These questions are not just for reflection — they are for direction. They help you become the kind of leader people want to follow.
Use This Table to Guide You
| Situation | Sample Tough Question | Purpose |
|---|---|---|
| Change | “What is worrying our people the most?” | Builds empathy and readiness |
| Performance | “What support do you need from me?” | Builds accountability and trust |
| Strategy | “Is this our vision or just mine?” | Creates shared ownership |
| Conflict | “What can we each do to make things better?” | Promotes teamwork and understanding |
| Self-Reflection | “What truth am I avoiding right now?” | Grows honesty and self-awareness |
Remember
The goal is not to have a perfect question. The goal is to create honest conversation.
When you ask tough questions, you open doors — for learning, for healing, and for change.
Closing Reflection
The best leaders I’ve met are not the ones who speak the loudest. They are the ones who ask the right questions — even when the answers are uncomfortable.
When you ask tough questions, you show courage. You tell your people, “We can face the truth together.” You remind them that leadership is not about pretending to be perfect. It’s about being honest, curious, and willing to learn.
I’ve seen this again and again in my work with leaders across the Philippines — from city mayors and school heads to supervisors and entrepreneurs. The moment a leader dares to ask instead of tell, everything shifts. People begin to speak honestly. Teams become more creative. Problems turn into possibilities.
Asking tough questions doesn’t make you weak. It makes you wise.
So start today. Ask one question you’ve been afraid to ask — to yourself, your team, or your organization. Then listen. You might discover the answer you’ve been waiting for all along.
If You Remember One Thing
Leadership begins with curiosity. Growth begins with courage. And both begin when you ask tough questions.
Sources
- Carol Kinsey Goman, Ph.D. 10 Critical Questions for Change Leaders, American Management Association (AMA). https://www.amanet.org/articles/10-critical-questions-for-change-leaders/
- Frank Bucaro, 10 Questions Every Leader Needs to Ask, Corporate Compliance Insights (2015).
- Challenging Conversations and How to Manage Them, Acas Guide (2014).
- How Vulnerable Are You as a Leader? Women Rising.
- Allison E. McWilliams, Ph.D., Managers Need to Ask Hard Questions, Psychology Today (2023).
- Kelly George, The Power of Asking Questions as a Leader, Center for Sales Strategy (2023).
- Joan Cheverie, Why Asking Good Questions Can Help You Be a Better Leader, EDUCAUSE Review (2017).
- IPAT, The Question Never Failed Us: The Art of Asking Catalytic Questions, Interpeace, Geneva (2015).
