The Art of Asking Good Questions
If this is your first experience with CityLead, or your first time reading our CityLead TakeAway, we want to welcome you! Here at CityLead, we believe that by coming together once a month as a business community, we can make each of our cities a better place to live, work, worship, play, and raise a family. In every CityLead session, we look at one of three types of leadership through a Biblical lens: self-leadership, team leadership, and organizational leadership.
Today, we’re talking about asking good questions – a skill that sounds simple but is surprisingly difficult to master. As you go through the content in this CityLead TakeAway, think about the questions you ask in your business, your relationships, and your own personal growth. Are they leading you to deeper understanding, or are they keeping you stuck in shallow conversations?
Why Questions Matter
Questions are the gateway to learning, connection, and wise leadership. Here’s why they’re so important:
- They avoid small talk and get to deeper issues. Without good questions, you’ll only talk about the weather or last night’s game – things that don’t move the needle.
- Profound questions affect your ability to provide wise leadership. The better your questions, the better your decisions.
- Good questions allow you to learn and process. They help you understand situations, people, and problems more fully.
- Asking good questions increases your confidence. When you truly understand a person, company, or need, you’re better equipped to help.
- Your attitude when asking questions is critical. Questions can build people up or tear them down. Avoid using questions to critique or condemn – ask with genuine curiosity, not a critical spirit.
Two Golden Rules for Asking Questions
1. Only ask one question at a time.
Don’t rapid-fire questions without waiting for answers. Ask, listen, follow up. Then ask another. Give the person space to give you a thoughtful, articulate response.
2. Don’t diminish your question.
Never say, “I know this is a stupid question, but…” You’re not expected to know everything. Asking questions isn’t a sign of weakness – it’s a sign of wisdom. The people who never ask are the ones who stay stuck.
Be Prepared to Learn
You never know when an opportunity will present itself. Pastor Bill shares two stories of sitting down for lunch at events, only to have the president of one of America’s largest retail companies – and later, the head of a top-five global nonprofit – ask to join him.
What did he do? He asked questions. And he took notes.
Two tips when you get that unexpected lunch:
- Pay for the meal – even if they’re a billionaire.
- Take notes – you will forget what was said if you don’t write it down.
Two Purposes of Questions
Questions serve two purposes, and it’s helpful to clarify which one you’re pursuing:
- Questions for your learning – You need information, so you ask.
- Questions for their learning – You’re coaching or helping someone grow through guided questions.
Let the other person know which mode you’re in. “I need to understand this better – can I ask you a few questions?” versus “Let’s talk about you – I’d like to ask some questions to help you think through this.”
All of us coach, whether we’re paid to or not. When someone does something well, we encourage them. When they miss the mark, we help them improve. Questions are a core part of that process.
Four Types of Questions
1. Brainstorming Questions
These help you and your team maximize ideas and think creatively.
- What problem are we trying to solve?
- What if money and staffing were not an issue – what could we do?
- Why not try this?
- Would you put your personal money into this idea?
- Is it ethical? Is it moral? Is it legal?
2. Decision-Making Questions
These bring clarity so the right decisions are made.
- What decision are we facing?
- What would happen if we didn’t make this decision?
- What are the best options and their implications?
- What is the best timing to make this decision?
A word on timing: Don’t kick hard decisions down the road. Pastor Bill recalls helping a company with strategic planning – they identified difficult issues but placed them in years three, four, and five. Those issues will still be there in two years, pushed back again.
Short-term pain is better than long-term pain. Deal with it now. As the Bible says, “Don’t let the sun go down on your anger.” The longer you wait, the bigger the problem becomes.
3. Interviewing Questions
Good questions help you get behind the candidate’s smile and beyond their resume.
- What was your life like in fourth grade? This question reveals more than “Tell me about your family.” By age ten, children understand dysfunction at home – and they carry it with them. You’re not condemning anyone; you’re understanding what they bring to the table.
- Why do you do what you do? Why do you want to work here?
- Are there any skeletons in your closet that might affect your work? (Check with HR on phrasing, but find a way to surface potential issues early.)
- What is your life dream?
- If you could only accomplish three measurable things in this role, what would they be?
- How would you describe your decision-making process?
- Do you prefer to set and achieve goals? (Doer)
- Do you prefer to define and solve problems? (Thinker)
- Do you prefer to see and seize opportunities? (Risk-taker)
You need all three types in your organization – but not all three in every role. Make sure you’re hiring for the right fit.
- What are the three most important principles that guide your life?
Values matter. If someone believes they’re only accountable for what’s in writing – and you believe your word is your bond – that’s a values mismatch. Ask about values before you hire.
4. Organizing Questions (Personal)
These help you maximize your time, choices, and personal decisions.
- What is causing you stress? What decisions do you need to make to alleviate it?
- What are your responsibilities and commitments? Your strengths and weaknesses?
- What are the top things you need to do today?
- What should you not do today? What should you stop doing altogether?
The Post-It Note Exercise:
Give two sticky notes to someone you work with. On one, they write what they think you should be doing. On the other, they write what they think they should be doing. You do the same for them. Exchange notes.
The differences are often shocking – and clarifying. Twelve hours a week might be freed up because someone was doing work you never asked them to do.
The Biggest Question
Pastor Bill closes with a story from early in his career. He was in his twenties, selling a large tract of land. To get aerial photos, the landowner flew him in a small plane. They landed on a rural road – and were immediately surrounded by helicopters, SWAT teams, and armed officers in full tactical gear.
After searching everything, the lead officer removed his helmet, looked Pastor Bill in the eye, and asked:
“What on earth are you doing here?”
That question has stayed with him ever since – not because of the drama of the moment, but because of its deeper meaning.
You are here for a purpose. What is it? Why are you here – not just at this event, not just in South Florida, but on this earth?
All the other questions are good. But this is the one that matters most.
Reflection Questions
- When was the last time you asked a truly profound question – one that moved a conversation from shallow to meaningful?
- Do you tend to ask questions for your own learning, or to help others learn? How can you be more intentional about both?
- Which of the four question categories (brainstorming, decision-making, interviewing, organizing) do you need to grow in most?
- Are there hard decisions you’ve been kicking down the road? What would it look like to deal with them now?
- How would you answer the question: What on earth are you doing here?
We hope you learned something valuable from today’s CityLead session. Take a moment to identify your top takeaway – and decide what you’re going to do about it this week.
We can’t wait to see you at the next one!
