If you want to know a simple move to come across to others as more likable, engaging, and enjoyable to be around, you need to understand one fact; most people love to talk about themselves. That’s not a negative about the other person, most people find personal value in sharing with others. 

I’ve leveraged this knowledge several times in the past by going all in on asking a lot of great questions during my first few interactions with the person. It helps build rapport, fast-tracks relationships, and helps accelerate your career.  Today we’ll look at how great questions can serve your relationship-building skills and help you discover problems before they escalate to become larger issues. 

Ask great questions by listening

You’ll always want to start off with questions that get the person to open up and begin sharing information with you. Some good starting points include:

  • Open-ended questions around a shared purpose. This could be around the reason for the meeting or gathering. (What has been your favorite session at the conference so far? What are your thoughts on the CEO’s announcement last week? How do you think the recruiting season is going?)

  • Inquisitive in thier personal endevors. Questions that center on a person’s interests, hobbies, or passions are great starts to open a number of doors to further the conversation.  (What gives you energy, What are you working on outside of the job that gets you excited?) 

  • Listen to their reply for opportunities to dig further in or highlight a topic. (You said _______, tell me more about that.) This will continue a line of discussion until you have exhausted your questions or the topic naturally wraps itself up. 

The secret to a great facilitator is their ability to navigate a conversation by listening to what is said and then asking follow-up questions. It may almost seem effortless as they guide the group through self-discovery or the right path forward. That should be your goal as well. Listen for the right points to send the conversation deeper while doing it in a way that seems natural. It shouldn’t feel forced, inauthentic, or clumsy. 

Simplify your questions


There are going to be times when you have all sorts of thought-provoking questions in your head or you may really excited to hear more or receive additional details. As a result, you may bundle your questions without even realizing this. 

I was recently at a conference where a local well-known entrepreneur gave the morning keynote address and had a Q&A at the end. There was no shortage of questions from the audience! One attendee asked something along the lines of, ” What made you want to do this, what continues to inspire you and what are your goals for the future?” Those are all great questions, but the speaker had to pause and took a moment to process the bundled questions, ultimately missing one of the questions altogether. 

When you find your mind trying to bundle a bunch of questions, sort through them and pick up the most important 1 or 2. Ask one, and then the other as a follow-up if it’s still appropriate. You’ll keep your person engaged and get higher-quality answers as a result. 

Shoot for the deep but be satisfied with the surface


Mining the depths of a person’s thoughts, motivations and insights can be invaluable to getting a better understanding of the person and the topic at hand. Remember that not all conversations will go into the inner crevices of your mind and soul. Think of those deep conversations as cave diving. The surface-level conversations that you have are the safety gear and support systems so that you can safely travel down below. 

In conversations with some of my closest friends, we’ve discussed some very deep and personal topics. We’ll also talk about video games or running beforehand or afterward. Don’t be disappointed if a conversation doesn’t go as deep as you had hoped. Surface-level conversations carry value as well and provide a sense of trust and safety to go deeper into another conversation. 

Don’t be afraid to ask a question

Be brave and ask those questions that may make you look naive. It is better to approach it on the front end and learn valuable information as opposed to playing along and being left in the dark in directions or walking away with the wrong information. 

If the idea of putting yourself out there makes you nervous, address that as well to help you get through the conversation. I’ll often say something along the lines of, “Forgive my ignorance here, but can you tell me what _______ means?” or “This may be a naive question, but can you help me understand _____?”

Typically the other party is going to affirm that your question is in fact not dumb, and will be happy to help give more clarity. There is also a chance that someone else has the same question, but is too afraid to ask themselves. 

Keep those questions coming! Great, thought-provoking questions, help you and those around you grow in knowledge and trust. 

Make a better tomorrow. 
-ZH