August 2026
By Jessica Benjamin
Do you know you have the power to help someone understand and communicate their heart through the questions you ask? The power of good questions opens up greater awareness of oneself, others, and the surrounding circumstances.
There will be times when someone you love is going through a hard season. Perhaps they’re facing an unexpected pregnancy. Perhaps they’ve lost a job, or a family member, a relationship has crumbled, or they received a hard diagnosis. They may not know what to do, or even understand the emotions they’re experiencing.
As much as we want to share our thoughts, advice, and suggestions in support of their well-being, there are immense benefits to being a good listener, rather than just a good talker. It is so helpful when we take the time to explore how our loved ones are feeling in the midst of their circumstances, and hear their perspectives, fears, and hopes.
The ability to ask good questions is an exceptionally useful skill. It can open the doors to better dialogue and allow our loved ones to share their hearts and even better understand themselves, their situations, and their hopes.
LET’S IMAGINE… you are supporting a young adult friend, Samantha, who just found out she’s unexpectedly pregnant. Click to read more.
Samantha had been acting unlike herself, and after asking her whether everything was alright, she opened up and shared that she found out she was pregnant, and she doesn’t know what to do.
One way to support a loved one is to be a safe place for her to talk openly and navigate her circumstances, thoughts, hopes, and fears surrounding the situation. Asking permission to talk about what’s going on and moving to a space where your loved one feels comfortable is a great start to being a good listener and letting your loved one share her heart.
LET’S IMAGINE… Click to read more.
Samantha is clearly feeling a lot of conflicting and overwhelming emotions, but doesn’t express herself beyond vague, generalized worries and broad statements about herself and her circumstances. You wonder if there is more that she wants to share, and invite her to join you in a quiet and comfortable place where you can take time to talk a bit more.
Asking good questions is a skill that encourages deeper and clearer discussions. Good questions move you from generalized conversation to generative conversation—where you uncover new ideas and insights rather than casual and superficial topics.
LET’S IMAGINE… Click to read more.
With a warm cup of tea in hand, you make sure Samantha feels ready to talk and agree that the living room is a good place for a heart-to-heart. She briefly shares about her relationship with Jacob, realizing she’s pregnant, and says she doesn’t know what to do next. She shrugs and trails off, staring at the floor. You notice gaps in the story she’s shared, so to better understand, ask some “closed-ended” questions to get more information.
The Power of Closed-ended Questions
Closed-ended questions ask for specific information and can usually be answered in just a few words. They don’t require a detailed response.
Good uses for closed-ended questions:
- Getting essential, factual information
- Helpful if people are having a hard time sharing
- Can be used to clarify or bring a point to light
- Can lead to open-ended questions
Drawbacks to closed-ended questions:
- Receive limited information
- Can become an interrogation-style conversation
- Can guide loved ones into responses you desire
Examples of closed-ended questions:
- How long have you been in this relationship?
- Would you describe your communication with your partner as strong or weak?
- Have you told your parents about your pregnancy?
- How old are your children?
- Did you know nearly half of pregnancies in Canada are unplanned?
LET’S IMAGINE… Click to read more.
After you ask Samantha closed-ended questions like, “How long have you and Jacob been dating?” and “Does he know about the pregnancy?”, she responds with short, direct answers: they have been dating for about two years, but no, she hasn’t told him yet.
Next, you ask her open-ended questions, a general question like: “How is your relationship with Jacob?” and then a more specific question like: “How do you feel Jacob may respond to this pregnancy?”
The Power of Open-ended Questions
Open-ended questions encourage the responder to freely expand on a topic. Yet not all open-ended questions are equally open. You can build more or less structure into your questions, encouraging your loved one to speak specifically about their situation. Learning how to do this is where the true power of open-ended questions can lie.
Good uses for open-ended questions:
- Can be structured to provide conversational depth
- Lets loved ones answer in more detail
- Can naturally move a conversation along as new insights are uncovered
Drawbacks for open-ended questions:
- Broad open-ended questions can be too vague and may not help the person know what to talk about
- Unstructured open-ended questions may keep things superficial, generalized, and vague
- Open-ended questions may move conversation off topic
Here are two similar open-ended questions (with unstructured and structured examples):
Compare “What was your childhood like?” to “What do you remember about the way love was expressed in your family as you were growing up?”
- The first question can be answered in many ways
- The second open-ended question is more specific and guides the person on what to include in their answer
LET’S IMAGINE… Click to read more.
Samantha responds to your open-ended question (How is your relationship?) that it has been great. She feels love for her partner and is excited about a possible future together. She mentions some favourite dates they’ve gone on, and that she’s enjoyed being welcomed by his family.
Your follow-up question (How do you feel your partner may respond to this pregnancy?) helps guide the conversation toward the pregnancy while staying open-ended. She answers that she hopes Jacob would be supportive, but she doesn’t really know how he will respond, and that worries her. She knows she should tell him but doesn’t want to wreck or change the direction the relationship is going.
While you sympathize with the uncertainty, you continue to ask a variety of open-ended questions with an attitude of compassion, to help her explore her thoughts on the pregnancy and the next steps she’s thinking about.
Guidelines for Good Questions to Ask
Open-ended questions encourage your loved one to talk about themselves and their feelings. They are usually based on something already said and are used to explore the situation in greater depth to gain new insights. They also provide a model for future problem-solving.
Good questions usually begin with How, What, Which, When, and Where. Here are some examples:
- How do you feel about your pregnancy?
- What makes you think your parents will never accept your relationship?
- How do you feel about adoption, and is it something you’d like to talk about?
- Which living situation do you think you would like the most?
- How may I help you tell your mom that you’re pregnant?
LET’S IMAGINE… Click to read more.
As you and Samantha talk, you ask her a variety of open-ended questions that let her share her heart and feelings and understand her situation better. It slowly paints a picture of Samantha’s perspective and how she hopes to be a parent one day.
- How do you feel this pregnancy may change the relationships around you?
- Where do you see yourself in five years?
- When do you think life begins?
- What are your views on abortion?
- Would you consider adoption?
- What do you think about parenthood?
- When was a time your parents supported you through something hard? How did they show up for you?
- How do you think Jacob will respond when you tell him the news?
- What are ways I can support you as you share this news with Jacob and your families?
You mostly utilize open-ended questions and sometimes clarify a point with a closed-ended question. Samantha repeats and understands that she has a supportive family, even in hard situations, and becomes more aware of the support network around her that she could tell about the pregnancy. You can tell she is seeing a clearer picture of her situation, and that her next step is telling her boyfriend.
Some questions require caution or should be avoided. Let’s explore some of these “caution-tape” questions.
LET’S IMAGINE… Click to read more.
At one point, you ask a question that comes out wrong. Samantha tells you she recently lied when Jacob had pressed her about what’s bothering her. Without stopping to pause, you blurt out, “Why would you do that?” Samantha bites her lip and looks at the floor, clearly uncomfortable again.
You wonder: did that question come across the way you wanted it to?
You say, “I’m sorry, let me rephrase that: Is there a reason you didn’t tell him the truth when he asked?” That subtle shift in how you asked the question changed it from judgmental to neutral and exploratory. Samantha breathes out slowly and explains that her fears overwhelmed her in the moment, even though she really wanted to get the news of the pregnancy off her chest.
Questions to Avoid
“Why” questions:
These can have the subtle effect of implying judgment and put loved ones on the defensive.
Example: Why did you call him when you knew he wasn’t interested in a relationship with you?
When you need to understand the “why” behind a behaviour, use a gentle voice and instead of asking, “Why did you do that?” ask, “What led you to do that?” This rewording emphasizes exploring your loved one’s experience and transforms the question from a threat into an invitation to be introspective.
Rapid-fire questions:
These are several questions combined into one sentence. They confuse and pressure the other person, and are a poor communication technique.
Example: Where will you live, how will you pay your bills, and who is going to help you?
Questions containing the answers:
These are used to state opinions rather than genuinely inquire into the other person’s thoughts. This can be manipulative, whether that’s your intention or not.
Example: You don’t think you can have a baby and continue to work, do you?
LET’S IMAGINE… Click to read more.
You continue to be thoughtful about the questions you ask and what Samantha shares with you. Your good questions have helped her understand her feelings and fears, her hopes for her future, and also explore her current circumstances and steps she might want to take.
While she is still afraid and is aware of the uncertainties ahead, she is less overwhelmed and not feeling that her life is over due to the pregnancy. She is becoming aware that she can adapt her plans for the future and that good could come out of these circumstances. She also recognizes she is not alone. She has a supportive network of family and friends she can lean on.
Good questions will offer our loved ones the opportunity to better understand themselves and their situations. Good questions can help us recognize fears as well as hopes, and empower our loved ones to make decisions aligned with their hearts. When we bring what our fears and hearts hold into the open, they can be navigated, addressed, and guide our loved ones through the difficulties they may be facing.
In the simple story we imagined throughout this article, Samantha has had a positive relationship so far and a supportive family around her, yet she still faces fears and uncertainties about what lies ahead. Other unexpected pregnancy situations may be filled with more complicated relationships, financial or housing insecurities, absent support networks, and a myriad of other concerns.
Good questions can still help loved ones navigate very challenging or complicated circumstances. You can also check out this article from last month, where we share helpful steps that will complement asking good questions.
Finally, a great next step is to connect your loved one with a pregnancy care centre near them or online, where they can continue the conversation and access helpful support and resources.