top of page

The Difficult Conversation: 5 Tips For Leaders

Have you ever been in a situation where you needed to have a difficult conversation with a team member? Of course you have - we all have. But what do you do when that happens? What steps should you take before and during the conversation to make it go as smoothly as possible?

Difficult conversations aren't fun. But leaders must take the time to hone this skill.

Creating a safe environment for all team members means finding a middle ground in the interactions you initiate with each member. A leader has a delicate balance between being friendly and approachable and keeping professional boundaries.

Having a game plan before beginning a difficult conversation is essential. If you're going to have a meaningful and challenging talk with someone in your company, here are five tips that will help keep the exchange professional and productive.

Establish a clear purpose for the conversation

Leaders need to be clear about why they are having the difficult conversation and what precisely they are looking to achieve. Is an employee doing something wrong? Does an employee require clarification on their role or responsibilities? People will be more engaged if they know the purpose behind the challenging conversation and that it will lead to change or improvement.

By establishing purpose, the tone is set and gives the team member something concrete to focus on instead of feeling blindsided or confused by what's happening.

Consider the situation from their standpoint

Before entering a difficult conversation, it's essential to consider the team member's perspectives. What is it that they are struggling with? What is keeping them up at night? How can you support them in addressing these issues? Asking yourself these questions and approaching the conversation with empathy will help you understand where they are coming from and help you better frame the conversation so that it addresses the primary concerns directly.

Be attentive

During a difficult conversation, it is vital that leaders remain present and actively listen while the team member is speaking - remember, this is about understanding where another person is coming from so that you can better address concerns and work towards a resolution together.

If we are thinking about what we want to say next or interrupt before they can express themselves, we are telling them in simple terms that we do not hear them. Through active listening, we can guide the conversation by asking probing questions like "Where do your challenges lie" or "Tell me more about that" to understand their perspective truly.

By remaining present, you may learn something about them that you didn't know or see the situation from a different angle. If they see that you're switched on and engaged with them, they're more likely to do the same for you.

Determine what will happen next

Regardless of how the conversation went, leaders should always send a follow-up email summarizing the discussion and listing any action items for agreed-upon next steps.

Reiterating what was discussed while it's still fresh in your and the employee's mind provides the following:

  • Documentation of what was said and a reference point that can be revisited in future

  • Confirmation that both parties were heard - if the summary is sent and the employee sees something that doesn't align with their takeaways, they have the opportunity for clarification.

  • Guideline for expected outcomes

Don't limit your conversations to corrective ones

Emotionally intelligent leaders use their EQ to stay in tune with their employees' feelings and needs. They understand what motivates them and how they can be most productive. The more you talk to your team, the better you'll know what they need to succeed.

With an established rapport, leaders can identify areas of struggle before they become performance issues. In addition, when delivering corrective feedback, a positive connection between leader and employee will likely guide feedback to be more positively received.

Why Master Difficult Conversations?

Leaders have to have difficult conversations from time to time, but successful leaders make them a priority. Difficult conversations are never easy, but they're necessary given the complex environments leaders are immersed in.

Being effective at having difficult conversations isn't learned overnight. Still, difficult conversation skills can be leveraged by creating a balance of power where both parties feel represented.

Outstanding leadership is all about communication; the better leaders can communicate with their team, the stronger the team will be.

To explore your leadership style further and empower yourself as a leader, check out our Whole Person Leadership Cohort.

Stay Curious!


bottom of page