Emergent Leader Newsletter/001/How To Lead Difficult Conversations Like A Pro

Read time:  5 minutes

If you are holding off having difficult conversations with your team members, your team could be performing at a higher level. 

Here is the problem:  

Most clients I work with have no idea how they could improve, yet they have been referred to me because of performance issues. WHAT?!? That is right. I work with new and emergent leaders to help them develop their leadership skillsets so that they can succeed and thrive in their roles. And at the root of many of the skills gaps is either the unwillingness to lead difficult conversations or the lack of know-how to hold space for frank discussions. 

If you one day aspire to lead higher up in the ranks – or simply want to lead highly effective teams, the ability to hold space for difficult conversations is a skill that is very desirable and respected.  

Why is the inability to hold a difficult conversation a problem in the first place? 

One reason is to be able to intercept when a problem arises, such as performance issues on your team, lack of progress or results on a project, problematic behaviors, or unhealthy dynamics on the team. Left unchecked, with time, any of these issues will erode any positive team culture, productivity, trust, and bottom-line results – which, let’s face it, will be interpreted as a result of your leadership (or lack of). 

While for the team member in question, the consequences may involve being passed up for opportunities for more responsibility and growth – both professionally and financially and may even lead to being let go.  

So why not just have the conversation in the first place? 

You are paralyzed by fear. When we do not feel confident in a skill, such as holding the space for difficult conversations, we tend to focus on everything that could go wrong and wiggle our way out of going through with it. With my clients, the following reasons frequently come up:  

  • They are afraid of hurting the other person’s feelings; 

  • They are afraid of how the other person might react; 

  • They are afraid of turning someone against them. 

All valid concerns HOWEVER, here’s what I also know to be true: if the critical conversation is not had, the problem will no longer be about the team member. The negative attention will eventually shift to you and your inability to lead effective teams. 

How should you hold space for difficult conversations? 

Mindsets reframe: 

  • Remember: the rest of your high-performing team will appreciate the fact that you are not letting a poor performer erode the team’s efforts OR that unhelpful habits will not become a distraction to the excellent work your team does. 

  • If having a difficult conversation with someone that is based on facts turns them against you, that is their business. Not yours.  

  • Avoiding difficult conversations has never led to a higher sense of loyalty from a valuable, high-performing team member. It only breeds complacency from those who already limbo under the bar of “acceptable” quality work.

  • If the conversation is based on facts, the repercussions will be on the positive side. Everyone will move forward more effectively. 

  • By having the conversation, you are avoiding similar situations in the future, thus freeing up your time for more important things, such as providing more outstanding value to your team.

Preparing for the conversation:  

  • Communicate what the expected behavior/performance/quality of work is in the first place. While it may be obvious to you, it may not be for all your team members. Set the expectation for everyone and then hold them to that standard from now on. 

  • Understand that as a leader, you are there to support your all of your team members in pursuit of their success. Be present and check in regularly. 

  • Document instances where the individual was off-track – and how it impacted on the team’s ability to perform. Sometimes going through the “why” helps some individuals better understand how their work matters in the bigger picture and can be a huge motivating factor in their future work.

  • Book the conversation for a time when you both have enough space to prepare and discuss. Do not stun the individual. When you book a time in your calendars, fill them in on what the meeting will be about. Keeping them guessing will only have them imagining the worst – or blind-side them, neither of which will work in your favor.  

  • While you should not stay attached to any outcome from this conversation, be clear in your mind what it is that you need the other person to walk away with. What are the non-negotiables? What is up for negotiation?

In the moment:  

  • Be mindful of the energy you bring into the space. If you cannot keep your emotions, body language and tone in check, then you cannot expect the other individual to keep theirs under control either. People tend to mirror others they are in conversation with. If you appear calm and collected, they are more likely to remain that way also. 

  • Before stepping into a potentially tension-filled conversation, clear up any assumptions you have about the person in front of you. In fact, the only thing you should assume is that they are doing their best, and that you both want to succeed. By removing any labels or assumptions, you will bring a completely different energy into the conversation.  

  • Enter the conversation with a curious mindset and listen. Seek to understand rather than finish their sentences. If the other party truly feels heard and understood, they are again, less likely to react emotionally. 

  • Offer the individual the opportunity to ask clarifying questions. Think of this as a 2-way discussion that will not only serve to better set them up for success in the future but will also help you better understand what they need to succeed.  

  • Together, create a clear plan of action for the period until your next meeting. Not only should you paint a clear picture for them, have the other person re-iterate in their own words to ensure they fully understand what is expected.  

  • Practice with team members that may be less prone to react negatively before going about it with a more serious conversation. 

By getting into the habit of having an open and regular constructive conversation with all your team members, it will significantly reduce the need for more “difficult” conversations in the future. 


Whenever you are ready, there are 2 other ways I can help you:

1. If you are still looking to further improve your leadership skills, let me recommend starting with an affordable course:

→ The New Leader’s Survival Guide: Time Management 

→  Stand Out From The Rest: Communicate Like An Effective Leader  

2.  If you are looking for a more customized leadership development experience, leadership coaching may be the better option to get you to your professional development goals faster. Book a complimentary “Discovery Call” to discuss your goals and see if working with a leadership coach might be the way to go.