Luis Goncalves
Last updated on | Agile Coaching/Team Coaching

Getting Beyond Small Talk: Initiating Significant Conversations

by Luís Gonçalves
Significant Conversations


Hi guys, as a coach, it’s your job to get to know the team you’ve been hired to work with, to understand their needs and what motivates them as people, today I am going to talk about significant conversations.

Doing so in a short space of time, however, can be challenging; how does one get beyond basic questions, such as “How are you?” and “What’s new with you these days?” How does one catch the attention of hard-working employees and steer the conversation toward significance?

To answer this problem, I bring you some suggestions that I found in the book: “Coaching Questions: A Coach´s Guide to Powerful Asking Skills” by Tony Stoltzsfus. If you have the opportunity buy the book, it’s an excellent resource to have.

Start With Icebreakers

Icebreakers are every bit as useful in the office as they are at social gatherings; they help us to launch conversations, even if we have never met the individual we wish to converse with before.

By starting with something simple and non-threatening, we lower the guard of others, making them receptive to more intimate questions.

  • “How are you today?” Is always a good place to start—why? You can follow up the person’s answer to a question, e.g. “What’s beautiful about today?” or, “Just feeling okay? Why not very good?”
  • “What do you like best about what you do for a living?”
  • “I have a lot of new faces to familiarise myself with—can you tell me something memorable about yourself?”
  • “What’s your family like?”
  • “Where are you from?” Then, “Do you miss it, or do you like it better here?”
  • “What do you hope to gain from [the current event or situation]?”
  • “How´s your day going?” Then, “What´s been your favourite thing about today?”

Significant Questions

After trying out an icebreaker, take a moment to assess the listener’s body language: Does he or she look receptive to further conversation? If the answer is yes, start to delve into significant questions, which dig a bit deeper than icebreakers.

They usually tap into a person’s desires, identity, or get him or her to think about something important. Such questions can either be used to start a coaching conversation or be used at informal events of all kinds just to get to know the people around you a bit better.

Examples of significant questions are provided below:


  • “What´s the most important thing that´s been going on in your life over the last few months?”
  • “And what’s the best thing going on right now?” (If it does not obviously coincide with the important thing.)
  • “What’s on your mind right now? Is there anything I can do to help you out/Advice I can offer?”
  • “What are your concerns as a leader right now?”
  • “Name a joy and a sorrow that have affected you deeply over the last year.”


  • “Can you name an event in your youth that really shaped you as a person?”
  • “Do you have any spiritual beliefs? If so, why?”
  • “Did you have any mentors growing up?”
  • “If you could go back in time and meet a historical figure, who would you choose? Why?”
  • “What are your strengths?”

Personal Desires

  • “Do you have a dream or central goal you wish to achieve in life?”
  • “Are you actively pursuing it right now? If not, why?”
  • “Which burden would you most like to shed from your life?”
  • “If you had unlimited wealth, what would you do?”
  • “What´s challenging you right now? How do you feel about it?”

Tapping into the Minds of Organisational Leaders

  • “What was the best thing you did this month while acting as a leader? Is there anything this month you wish you had done differently?”
  • “In an ideal world, what would you like your organisation achieve?”
  • “What do you enjoy most about working with this (company, team, project)?”
  • “What does your team or organisation do best? What’s challenging it/them currently?”
  • “What do you think would propel your team to the next level?”
  • “Is there anything you want to change about your company? Why do you want to change it?”
  • “What is making you happiest as a leader right now? What’s stressing you out the most?”
  • “What makes you passionate about your organisation, and your job?”
  • “How does your work bring out the best in you?”

I would like to hear your ideas… Please leave a comment below.


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Luís Gonçalves

About Luís Gonçalvesçalves1979

Luis Gonçalves is an Entrepreneur, Author & International Keynote Speaker. He works with Senior Executives to implement his ‘Organisational Mastery’ system so they can greatly increase the effectiveness and efficiency of their organisations; enabling them to become recognised and highly rewarded Leaders.


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