I’ve had a number of coaching calls this week with leaders who have to deliver tough news to a team member, and I’ve noticed a couple of similarities.

First, all these leaders are putting up with disruptive and insubordinate behavior to the detriment of the rest of the team, because their intention is to demonstrate empathy.  Second, all my clients asked this question, “OK, if I’m ready to tackle this conversation, how do I do it in a way that demonstrates empathy and holds the boundary on behavior we expect?”

Great questions, right?  Before we dive into these questions, I want to pause and let you know what I’m going to share with you applies to all of our roles as leaders – parents, partners, siblings, friends and while we are at work.  I’m going to stick to the ‘work’ setting. The information and tips I’ll share with you translate across all leadership roles.  So, let’s dive in.


Understand Empathy

Empathy is simply the ability to feel with another person.

Read that again.  To feel ‘with’ another person.  NOT ‘for’ another person.  This is a key distinction when we talk about empathy because it’s so easy to cross the line and act from a place of sympathy (feeling for someone) instead of empathy (feeling with someone).

When applied to the team member who isn’t meeting expectations or is being disruptive and insubordinate, our role as their leader is to understand why this might be happening, to try and feel with them.  Our role is not to make excuses, or ‘put up’ with this behavior, because we feel for them.

Empathy is not fixing or agreeing with someone.  Empathy does not endorse or condone behavior.  Empathy is simply demonstrating understanding.


Self Check-In

As with any difficult or tough conversation, it’s absolutely critical that you check in with yourself and make sure you are in as neutral of a state as you can be.  What is neutral?  You’re physically, mentally and emotionally at the centre of your being.  You’re rested, nourished, calm, clear in thought and open to receive.   If any one of these aspects is out of balance when completing this check-in, ask yourself if there is a way you can bring this aspect into balance before you have the conversation.  Some suggestions are:

  • Plan conversations for the morning when you’re more likely to be rested.
  • Have a snack before or provide snacks during the conversation.
  • Exercise before the conversation – even a 15 minute brisk walk helps bring us back to center.
  • Journal about how you are feeling and what’s most important in this conversation for you.
  • Talk to a trusted advisor, coach or friend prior to having the conversation to ensure you are open to exploring and not stuck in your own thoughts.


Be Curious

Get curious about why this behavior you are seeing might be happening.  It seems important to state that behavior stems from feelings or emotions which are generated by the thoughts, judgements and conclusions we make about situations, people and circumstances.  Here are some open curious questions to help you understand what’s really going on for this person.

  • I’ve noticed [insert behavior here]; as this isn’t typical for you, I’m wondering what else might be going on for you?
  • How are you feeling about [insert situation here]? Followed up with; Why do you feel that way?
  • Help me understand why you reacted/behaved that way?
  • What are the implications of your behavior?
  • How do you see your behavior affecting the team?


Check for Understanding – Don’t Assume!

Once you’ve asked a few curious questions and have a sense of what might be at the core of the issue for the team member, repeat back what it is you think you’ve heard.  You can use the following sentence starters to help you get going:

  • What I heard you say was …
  • If I understand you correctly

Until you have confirmation from the team member that they feel heard and understood, you will not be successful in moving the conversation forward.  Repeat curious questioning and checking for understanding as many times as necessary until the team member confirms that you have heard them completely.


Communicate Expectations

Now that the team member feels heard and understood, you can communicate your expectations.  State clearly and directly what it is you expect from them going forward and why this expectation is important to them personally and the team.  This might look like …

  • My expectation is that all team members show up on time for meetings. This means either early or within 2 minutes of the meeting start time.  If you are unable to do this, prior communication to the team about your absence is expected.  This is important for you because doing what we say we will do builds trust and trust is important to the team productivity and effectiveness.


  • My expectation is that all paperwork is completed within [X] timeframe. This is important as it protects your personal liability and helps reduce errors/omissions which cost our team additional time and resources.

Remember communicating something is a two-way street, so before you jump to the next step be sure to check for understanding.  A simple yet powerful statement is “Tell me in your own words, what the expectations are.”

If there was understanding, you’re ready to move on.  If they didn’t quite hit the mark, go back and restate the expectations and check again to ensure there is understanding.


Align and Offer Support

Now that you have a clear understanding what’s going on for the team member and have laid out the expectations, you can confirm alignment and offer support, so they are successful in meeting the expectations.   This might look like …

  • Now that you understand the expectations and I understand what’s getting in your way, what do you need from me to overcome these challenges?
  • How can I support you in meeting the expectations we just spoke about?
  • It sounds like we agree that you will meet [the expectation] and I will provide [this] support. Is that accurate?

You can practice empathy and hold a boundary or expectation firm.  The two are not mutually exclusive.  In my experience, leaders I’ve worked both with and for, who took the time to understand my situation and feelings while maintaining a high bar for expectations, produced the best results. They had the most fun and were leaders I ultimately wanted to follow and emulate.


I write these articles to support leaders in becoming more effective by embracing all parts of themselves and increasing their capacity to practice empathy.

Thank you for being here.  



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