Empathy Coaching

John Combellick
Lead, With a Question
4 min readSep 15, 2023

A guide to making the most of any one-on-one conversation

Photo by LinkedIn Sales Solutions on Unsplash

Perhaps the most critical skill any leader must master is that of empathy gathering.

A good leader understands their effectiveness comes from their influence. Growing influence is done through being curious about people, observant of social situations, and aware of power dynamics.

Empathy gathering is what enables all this, and leveraging empathy during a one-on-one will be a game changer for driving your team’s performance.

Empathy is often used to mean two things. First, and most traditionally, empathy means feeling what someone else is feeling, at a variety of different levels. With the onset of design thinking, empathy has taken on a slightly deeper meaning. It is the act of giving space to someone else. You are removing yourself and inviting someone to fill the void with their presence, ideas, wants, and needs.

This is the act that leaders must master. It can be done through observation, experiences, and, most importantly in terms of one-on-ones, conversations. Leaders and their team members regularly interact in one-on-one conversations, and often, that time is not used effectively as it could be. There is an art to making someone comfortable in the presence of an empty space and encouraging them to fill it with their entire self.

This is what this guide is for.

What it is not for: While I personally believe in the power of empathy in nearly every setting, this guide is not intended for situations where you may have to have a corrective action conversation or need to deliver a very clear expectation.

As a leader in a one-on-one, your primary and most sacred objective is to establish and grow trust.

Let this lower the stakes. You don’t need to worry about results, team performance, deadlines, or any of that junk. Set it all aside, and keep the tone of the one-on-one light. This is a marathon, not a sprint. As trust grows, so will results and performance.

What to do

  • Set a time and stick to a time. When things need to adjust, communicate transparently and proactively.
  • Be on camera, even if they are not. This is a small way to demonstrate your openness and vulnerability.
  • Pause notifications.
  • Consider the setting. Where will they be? Where will you be? If you are together physically, what space would be conducive to easy, comfortable, private conversation?
  • Have an emotion wheel out and ready to use!

Prep your starter question. There is an easy formula for this.

  • Pick a starter — “Tell me about a time…” “When was the last time…?” or “How do you feel about…?”
  • Pick an ending — This can be an emotion or an event.
  • An example — “Tell me about a time you felt angry at work.” or “When was the last time you didn’t know what to say in a meeting.”

What to say

  • Check in with a quick “How are you?” Get a sense of how they are feeling in the moment. Maybe they came from a stressful meeting or personal event. They might have something else on their mind. Give space to talk about that. It might be more important. Follow that for the entire 1:1 if it makes sense. Remember: Build trust. What they want to talk about is more important.
  • If everything feels good, deliver your starter question.

Continue to follow that up with:

  • “Tell me more about…”
  • “Why?” or “Why did you do/say/feel ….?”
  • Statements of reassurance like “That sounds difficult.” followed by silence. Let them fill the space however they see fit.
  • Know when to sit in silence without saying anything and let them reflect. They will speak up eventually, and it will likely be more insightful!
  • Listen for contradictions and call them out. “I heard you say this, and that seems at odds with what you said here. Tell me more about this.”
  • Tap into your inner therapist and ask them how it made them feel. It often works really well to pull up the emotion wheel, ask them to look at it and pick emotions. Pulling up the wheel gives it a levity that makes it easier to engage with the emotions.
  • Trust. I have said it and will continue saying it. You need to sense when trust may be on thin ice, and you should change tactics or move away from the topic. In the rare event that you get into a particularly sensitive topic, you can even say directly “It is important to me to understand this, but I feel like I may not be approaching this topic the right way. Can we pick this up tomorrow?”

What comes after

  • Write down the conversation, in full clear ideas, immediately after.
  • Send those notes to the participant and ask them to review. Give them a chance to confirm your notes matches what they walked away from the conversation with.
  • If it all matches up, document those notes in wherever one-on-one notes should be officially kept!

And most importantly, get excited for the next one-on-one!

Thanks for reading, and I hope this helps and inspires you!

I also write about AI and ethics!

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John Combellick
Lead, With a Question

Striving towards a human-centered world through leadership, learning, and curiosity.