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How To Lead A Difficult Conversation In A Way That Builds Trust

“I’ve noticed that you’ve been late on a few deadlines recently.  Your motivation also seems to be quite low in our weekly meetings. My concern is that this is affecting your performance.  Do you have any thoughts on where my observations might be coming from?”

Giving positive feedback or announcing a promotion are examples of conflict-free conversations you may lead.

However, when it comes to addressing a poor performance issue like the above example, the conversation can be much more challenging.

Just because you need to address a critical situation, doesn’t mean the conversation needs to be difficult.  It’s actually a fantastic opportunity to build trust.

The way you approach critical conversations paints a good picture of how you approach your role as a leader.

Above all, these conversations should be embraced, not dreaded or avoided!

However, there are a few important things to consider before jumping in.




Step 1:  Create a safe environment.

Questions to ask yourself:

  • Are the conditions right for a fruitful exchange: time, place, situation?
  • How can I make the environment a safer place (put yourself in their shoes for this one)?
  • What can I say or do to communicate respect at the very start?


Step 2:  Listen with your ears, eyes, voice & body.


  • Is my body language open to receive and exchange – do they feel free to open up?
  • What is their non-verbal communication saying? Their tone of voice?
  • Do my body language and voice match my words?

BTW, how would you feel if you got this message delivered with this face?


Step 3:  Ask smart questions to engage their creative thinking skills.


  • Are my questions designed to judge and criticize or to clarify and explore?
  • How can I frame my questions to get them to open up without needing to defend or justify?
  • How do my questions stimulate their creative thinking skills?

BTW, which of these questions do you prefer:

  • De-energizing question:  “Why did you do that?”
  • Energizing question:  “What would be another way you could do this in future?”

TIP: Avoid using “why”.


Step 4:  Communicate your messages clearly and respectfully.


  • Are my messages clear or is there room for doubt or interpretation?
  • Is my voice and non-verbal communication delivered in a respectful way?
  • Am I clear on what I want to communicate and the reasons behind my messages?


Step 5:  Co-create the next steps.


  • Have the decisions or next steps been agreed and/or created together?
  • Do we have a common understanding on the next steps?
  • Have I offered my support?



The next time you need to have a difficult conversation with someone, look at it as a chance build a bridge with them – a bridge that can help you cross a potential danger area together.

Rather than approaching it as a dreaded task that’s going to be difficult, approach it as a way to deepen your connection.

After all, if you go into a situation expecting it to be difficult or painful, it probably will be.

But if you go into it with eyes that are looking to connect and co-create, you’ll generate positive energy to lead the conversation effectively while building trust.

How do you approach your difficult conversations?  Please leave me and my readers a comment below.  Thanks!