Photo by Camylla Battani on Unsplash

Want to be more interesting, ask better questions

Leon Purton
Jun 25, 2019 · 6 min read

Find your second question and a more authentic connection

First Questions

I walked up to someone I’ve been wanting to connect with the other day. I knew they might have information that could help me, and I wanted this quick chat to create a connection with them that would enable me to get to an ‘ask’ at some point. I’ve been wanting to ask this favour for some time, but hadn’t had the chance — I also wasn’t sure how to create a win-win situation for them — where they felt like they’d get something out of it too. I walked up to them, and the conversation went a little like this (not their real name)…

“Hello Jim, I’m Leon, nice to meet you — how was your weekend? You doing well?”….. “Yeah, doing well, had a nice weekend, did a few chores but pretty relaxing — how are you?”…..”Good thanks!”.

Now — they know my name, but where do I go from here? How do I proceed with this conversation? Typically, I’d have asked some other veneer, shallow questions and if I felt like there was sufficient enough of a connection, I’d get to asking how I could help them and if they could help me with this one thing. After failing at creating anything substantial I’d traditionally await the next opportunity to engage in dialogue, and hopefully build on the information and detail I’d gathered at our first interchange. For instance, next time I might ask “Any chores done this weekend?”, or “Still doing well?” — Wow — such a deep and insightful question….

With enough of these little shares, I’d build up enough rapport to ask them. Sometimes you can have some trust and credibility that allows you to ask straight away, but sometimes you don’t. Either way, asking without any rapport or connection will not always get you what you need, even with some attached credibility.

These types of questions fit into the bucket of first questions, they focus on short answers and most of the time don’t require any thought in answering. If you want to create a connection, you want to be remembered by them, you need to find a way to shift you both out of ‘first gear’ in a conversation. You need to find your second question.

In this, I’ve been influenced by a great connection builder. Someone who has provided such great content and now made a living out of asking deep insightful questions and creating authentic relationships — Lewis Howes. Lewis will regularly ask this question on his wildly successful ‘The School of Greatness Podcast’.

This is coupled to Lewis’ attitude of gratitude focus. He will even sometimes ask “What are you most excited about right now?”.

Each of these are powerful questions to ask, and fit into the grouping I like to call second questions.

Second Questions

Second questions are not the literal ‘second question’ you ask, but they should not be too far into the conversation. These are the important depth changers, they shift the gears of the conversation and engage a different part of the brain. They create a relationship and the release of information that not many people will actually know. They give you an opportunity to really understand someone and in this, you create the opportunity to identify how to give them some of your thoughts and energy. You create value for them and really get to understand them as well.

Imagine that instead of retreating from a quick chat with Jim, knowing that I’ll have to work on that deeper connection with a few more conversations, I’d instead followed on with; “What is your biggest challenge right now?”. After some thought, he may answer “Choosing the right school for Andy”, or “Convincing the Board to find resources for this project”, or “Staying consistent with my Marathon training”. I would now have some information, and Jim would know that I was interested in what was troubling him.

In another alternate reality, I could have asked “What is it that you have done recently, that as you were doing it, you lost track of time?”. He might have answered, after some thought, “On the rower this morning”, or “Dancing with Marie last weekend”, or “Building my latest Lego” or “The Saturday morning crossword”. Again, each of these tell me a little more about Jim, and what he loves to do.

Imagine that, if I ask this question of him, he may in turn ask that question of me. Instead of us exchanging banality and vanilla questions at a very superficial level, we are now exchanging questions at a deeper, more thoughtful level.

This is a game changer where real, genuine and authentic connections are so important to happiness, growth, progression and development. Brene Brown say’s it so well:

“I define connection as the energy that exists between people when they feel seen, heard, and valued; when they can give and receive without judgement; and when they derive sustenance and strength from the relationship”. — Brene Brown

So, now what?

I was talking to someone the other day, and they said, “You seem so good at mingling — I don’t know what to say”. I asked them, “What is your favourite second question?”. After a blank stare and asking what I meant, I explained my definition. After a few seconds of consideration they responded, “I have no idea, I’ve never thought about that”.

After giving them some of the above examples they realised what I meant, and how powerful it could be to have some questions that didn’t make them uncomfortable to ask. This is important, you have to feel comfortable asking it, and even more, comfortable answering it if it is asked back to you.

I’ve compiled a brief list of second questions for you look over, but I’d really recommend thinking about it yourself. Think about which questions you find interesting, and how you might answer them, then think about when you could use them.

Here is a tip — you can use them everywhere!

These questions will create deeper, more thoughtful connections with your family, friends, peers and colleagues, your boss, your sports team, whomever you choose and are brave enough to ask. Here a few that I have collected or created over time:

  • What are you most grateful for?
  • What are you excited about?
  • What is you biggest challenge right now?
  • What is it you were doing lately, that while you were doing it, you lost track of time? (p.s. this is a definition for adult play).
  • If you could change one thing about X, what would it be?
  • When have you recently felt the happiest?
  • What is your strongest childhood memory?
  • What’s the one question you need answered right now?
  • What was the last thing you did that took you out of your comfort zone?

Importantly, this selection is aimed at creating deeper connections and stronger relationships. This applies at work, but can benefit in all areas of your life.

So, create your second question list, focus on the body language and demeanour of the person you are speaking too, and ask away. The worst thing that can happen, is that they believe you ask questions that require thought. The best thing — you create relationships that can help two people.

Comment your favourite questions. Tell me what works for you, or why you think this could help you.

Stay safe and keep smiling.


A photo of a stunning sunset over sugar cane fields in the Clarence Valley — Leon Purton

You can find me on Twitter here.

Sparks Publication

An accumulation of ideas that provide an opportunity to transfer a spark from one persons mind, to another persons soul. Leadership, growth, productivity and personal development.

Leon Purton

Written by

Spark writer — creating little sparks of inspiration in peoples soul. Engineer — Leader. Top Writer in Leadership

Sparks Publication

An accumulation of ideas that provide an opportunity to transfer a spark from one persons mind, to another persons soul. Leadership, growth, productivity and personal development.

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