Real-world examples of asking open-ended questions that actually work

Why the best examples of asking open-ended questions matter now

In 2024–2025, more of our conversations happen through screens, quick messages, and back-to-back meetings. It’s very easy to stay on the surface: “You good?” – “Yeah.” – and that’s it.

That’s where good examples of asking open-ended questions come in. Open-ended questions invite more than yes/no answers. They give people room to:

• Explain how they really feel
• Share context and backstory
• Reflect on their own thinking
• Explore options instead of defending a position

Research in counseling and motivational interviewing shows that open-ended questions can increase self-reflection and engagement in change conversations (NIH / NCBI). In coaching and leadership, they’re a powerful way to build trust and psychological safety.

Let’s skip the theory-heavy approach and go straight into real examples of asking open-ended questions, then break down why they work and how you can adapt them.

Everyday life: simple examples of asking open-ended questions

Before we get into coaching and leadership, let’s start with everyday conversations. These are the best examples to practice because you can use them today with friends, partners, or family.

Instead of: “Did you have a good day?” (yes/no)
Try: “What was the most interesting part of your day?”

Why it works: It invites a story. There’s no right or wrong answer, and it nudges the brain to scan the day for a highlight.

Instead of: “Are you mad at me?”
Try: “How are you feeling about what happened between us earlier?”

Why it works: It focuses on their experience, not just their label of an emotion. It also opens the door to nuance: annoyed, confused, hurt, mixed feelings.

Instead of: “Do you like your new job?”
Try: “What’s your new job been like so far?”

Why it works: They can talk about good and bad parts, expectations vs. reality, and how they’re adjusting.

These are small, simple examples of asking open-ended questions, but they completely change the tone of everyday conversations. You move from checking a box to actually connecting.

Coaching: real examples of asking open-ended questions with clients

If you’re a life coach, mentor, or manager who coaches your team, your questions are your main tools. Here are real examples of asking open-ended questions in a coaching context, with the intention behind each one.

Example 1: Exploring goals

“When you imagine your life a year from now, what feels different from today?”

This question invites vision and emotion, not just a bullet list of goals. It helps clients paint a picture in their own words.

Example 2: Understanding motivation

“What makes this goal important to you right now, at this stage of your life?”

Instead of “Why is this important?” (which can feel like a challenge), this version is more curious and grounded in timing.

Example 3: Unpacking obstacles

“When you’ve tried to make this change in the past, what usually got in the way?”

This normalizes difficulty and invites honest reflection about patterns, not self-blame.

Example 4: Building on strengths

“Think of a time you handled something similar really well. What did you do then that might help you now?”

Here, the client becomes the expert in their own life. You’re guiding them to find their own strategies.

These are examples of asking open-ended questions that support insight, not interrogation. They nudge the client to look inward, connect dots, and generate their own answers—core skills in effective coaching conversations.

For more on the impact of reflective and open-ended questions in coaching and counseling, you can explore resources on motivational interviewing techniques from the National Institutes of Health (NIH / NIDA) and related training materials.

Work & leadership: examples of asking open-ended questions with your team

Leaders who only ask, “Is everything on track?” usually get one answer: “Yep.” That doesn’t mean everything is fine; it just means people don’t feel invited to share more.

Here are examples of asking open-ended questions in a work or leadership setting.

During 1:1s

• “What’s been the most challenging part of your workload this month?”
• “How are you feeling about your growth here over the last six months?”

These invite honest feedback about workload, stress, and development, instead of forcing people to say, “It’s fine.”

After a big project or launch

• “Looking back at this project, what are you proudest of?”
• “If we ran this project again, what would you want us to do differently?”

Notice how these questions focus on learning and reflection rather than blame. That’s how you build a culture where people feel safe bringing up problems early.

When someone seems disengaged
Instead of: “Are you unhappy here?”
Try: “I’ve noticed you seem quieter lately. How have things been feeling for you at work?”

This is one of the softer but powerful examples of asking open-ended questions because it names what you see without accusing, and it gives them space to talk about workload, burnout, or personal stress.

Psychological safety research from places like Harvard Business School shows that when leaders ask genuine, open-ended questions and really listen, teams are more likely to speak up, innovate, and report problems early (Harvard).

Tough conversations: examples of asking open-ended questions when emotions run high

Conflict and sensitive topics are where open-ended questions really earn their keep. You’re not just trying to collect information; you’re trying to lower defenses and increase understanding.

Here are examples of asking open-ended questions during hard conversations:

When someone is upset with you

“Can you walk me through how you experienced what happened?”

This invites their story from their point of view. The phrase “how you experienced” makes it clear you’re interested in their internal reality, not just the facts.

When you disagree but want to stay curious

“What experiences have most shaped how you see this issue?”

This question gently moves the conversation away from who’s right and into how we each got here, which is often where empathy lives.

When someone shuts down

“What would make it feel safer or easier for you to share what you’re thinking right now?”

This is a powerful example of asking an open-ended question that respects their boundaries while still expressing interest.

When talking about mental health or stress
Instead of: “Are you okay?”
Try: “How have you been coping with everything on your plate lately?”

This aligns with guidance from mental health organizations like the National Institute of Mental Health (NIMH), which encourage open, nonjudgmental questions when checking in on someone’s well-being (NIMH).

Digital life: examples of asking open-ended questions over text, chat, or video

In 2025, a lot of our personal and professional conversations happen in short bursts: Slack messages, DMs, quick Zoom calls. It’s easy to default to closed questions like, “All good?” or “You there?”

Here are real examples of asking open-ended questions that work well in digital spaces:

Checking in with a remote teammate

“What’s been the hardest part of working remotely for you this week?”

This acknowledges that remote work has ups and downs and shows you’re open to hearing the real answer.

Following up after sending feedback by email

“After reading my feedback, what’s standing out to you the most?”

This gives the other person a chance to share their interpretation, concerns, or questions, instead of silently stewing.

Supporting a friend over text

“You mentioned things have been heavy lately. What’s been weighing on you the most?”

This is one of the best examples of asking open-ended questions via text because it focuses the conversation while still giving them room to choose what to share.

In group chats or online communities
Instead of: “Everyone good with this?”
Try: “What concerns or questions do you have about this plan?”

Notice how the wording assumes there might be concerns, which makes it safer for people to speak up.

How to turn closed questions into examples of asking open-ended questions

You don’t need a giant script. You just need a habit: when you catch yourself asking a yes/no question, pause and reframe.

Here’s a simple pattern you can use to create your own examples of asking open-ended questions:

1. Start with “what,” “how,” or “tell me about.”
These open the door. “Why” can also work, but it can sound accusatory if you’re not careful.

• Closed: “Did you like the workshop?”
• Open: “What stood out to you from the workshop?”

2. Aim for stories, not verdicts.
Instead of asking if something was good or bad, ask for experiences.

• Closed: “Was the meeting helpful?”
• Open: “How did the meeting help you, and what’s still unclear?”

3. Focus on feelings, thoughts, or next steps.
This naturally creates richer answers.

• Closed: “Are you stressed?”
• Open: “How have you been feeling about your workload lately?”

Once you get used to this, you’ll be able to invent your own best examples of asking open-ended questions on the spot, tailored to the person and situation.

Common mistakes when trying to ask open-ended questions

Even with good intentions, some questions shut people down. Here are a few traps to watch for when you’re trying to create better examples of asking open-ended questions:

Stacked questions

“How are you feeling about the project, and what do you think went wrong, and what should we do next?”

Too much at once. People don’t know where to start. Break it into separate questions.

Disguised judgments

“What made you think that was a good idea?”

Technically open-ended, emotionally closed. It puts people on the defensive.

Try instead: “What was going through your mind when you made that choice?”

Leading questions

“How overwhelmed are you by this new system?”

You’ve already told them how to feel. Try: “How has the new system been affecting your work?”

Asking, then interrupting
An open-ended question only works if you actually give the person space to answer. Ask, then be quiet. Let the pause happen. Often, the most honest part comes after the silence.

FAQ: examples of asking open-ended questions in real life

Q1: What are some quick examples of open-ended questions I can use every day?
Some simple, go-to examples include: “What’s been on your mind lately?”, “How did that experience feel for you?”, and “What would you like to see happen next?” These work in friendships, relationships, and even casual check-ins with coworkers.

Q2: Can you give an example of an open-ended question for performance reviews?
Yes. Instead of asking, “Are you happy with your performance?”, you might ask: “When you look back at this review period, what are you most proud of, and where do you most want to grow?” This example of an open-ended question invites reflection, ownership, and future-focused thinking.

Q3: What are examples of open-ended questions to support someone’s mental health?
You might ask: “How have you been sleeping and taking care of yourself lately?”, or “When things feel heavy, what helps you get through the day?” These examples of questions open the door without forcing someone to label themselves as “not okay.” For more guidance on supportive conversations, you can explore resources from the Mayo Clinic on mental health and communication (Mayo Clinic).

Q4: Are there examples of asking open-ended questions that work with kids or teens?
Absolutely. Try “What was the best and hardest part of your day?”, or “If you could change one thing about school right now, what would it be?” These examples include room for both positive and negative feelings, which helps kids and teens feel more understood.

Q5: How can I remember to use more open-ended questions in the moment?
Practice turning your first thought into a second version. If you think, “Did you like it?”, pause and rephrase to, “What did you like or not like about it?” Over time, you’ll build your own mental library of examples of asking open-ended questions that feel natural to you.

If you take nothing else from this, let it be this: open-ended questions are invitations. They say, “I’m willing to hear more than the headline.” Start with a few of the real examples here, notice how people respond, and then customize. The more you practice, the more your conversations will shift from surface-level to genuinely meaningful.