Updated June 28th, 2023

There comes a point in your career as a team leader where you need to have difficult conversations with your team. Even if you have the best team, you still have to face these situations. Whether it is about attitude, performance, tactical issues or even something else, these conversations can be uncomfortable. But, the right approach can lead to positive outcomes and strengthened relationships. In this blog post, I’ll share four tips to help you navigate challenging conversations with your team members.

Handling difficult conversations, starter pack

Let’s face it tough conversations are a hard pill to swallow. Nobody likes to engage in conflict, especially when you’re a people pleaser and desire approval; maybe every tiny thing will feel like a difficult conversation for you. Your starting point is to know yourself well. What’s your management style like, what are your strengths and weaknesses, and how can you work with them? The good news is that every leader can improve continuously to achieve better results. 

There are four things you need to handle to achieve success while holding difficult conversations; I call it the “Handling Difficult Conversations Starter Pack.”

1. Prepare yourself emotionally and with the right thoughts and words
2. Focus on the issue
3. Be clear
4. Ask questions and promote open communication.

Let’s go into detail and check out how you can start preparing for your next talk, shall we?

#1. Prepare for handling difficult conversations

Anthony Saint Exupery, the French author of the famous book, “The Petite Prince,” said, “A goal without a plan is just a wish.” You don’t want to keep wishing things get better if you don’t plan for success.

That is why I recommend to my NMA students to prepare in three ways: with thought, words, and emotions. 

Prepare with thought.

First, clarify your thoughts, identify the key points you want to address, and anticipate possible reactions or responses. Second, you have to be clear on the issue and the problem you are addressing. If you are hazy on the facts, it will come out messy and you won’t have the desired effect because you can’t articulate the issue. Take time to get your facts straight. Why is it a problem?

Plan your words.

Once you have jotted it down, the next step is to pick your words.  “Stay away from words that trigger defenses.” You must choose your words carefully to ensure your message is effectively communicated while being mindful of the emotions involved. 

Stay away from accusatory words or sentences about the person. Be clear that the person is not the issue, just the behavior, actions, or performance.

Prepare yourself emotionally.

If you know the personality style of the person you will talk to, you can prepare for the reaction. If you will be addressing a highly emotional person, prepare yourself emotionally – that their response is not personal to you. Learn to accept that their personality just lends them to be sensitive to what you say. What helped me was remembering that everyone is fighting their own battles. Yes, this is a place of work, but we are all bringing our traumas and issues to work. It is part of who we are and will manifest itself in all sorts of ways.

#2. Focus on the issue.

Ok, so you’ve prepared, you’ve got your outline and everything, and you are in the conversation itself; what do you do?

The next step is to get there quickly.  Dancing around the issue and not getting to the point is one of the biggest mistakes I see in new managers when having difficult conversations with employees. They get nervous and then end up talking about everything under the sun before jumping to have the discussion. 

This gibberish makes you more nervous because you’re not ripping off the band-aid; instead, you’re working yourself up into a knot about what could happen when you do. And it makes the person on the receiving end nervous because their head is probably going to the worst place possible. After all, that’s what we do as humans, right?

So tell them right away why you’ve called them in. Make use of the following examples:

• “Hey, I brought you in here because I want to talk about a few things I noticed during the last project you led.”
• “Hey, I brought you in here because I want to talk about your punctuality over the past couple of weeks.”
• “Hey, I want to talk to you about how you reacted in our team meeting.”

Get straight to the point – it is the right thing to do.

#3. Be clear.

Once you have stated what you want to talk about, aim to be clear about the issue and its impact. 

Nothing is more frustrating than having to sit there and figure out what your manager has an issue with. It is why we prepared so that you can work out the kinks. Instead, be clear, let them know the issue, and then help them see how this impacts things. 

Here’s an example,

“Hey, you have shown up 20 minutes late for your shift the last three days. This pushes Suzy back with the ability to leave her station, which affects her being able to show up on time for a mentoring session she’s having with other team members.”

Notice how I was clear? I even stated three days, not a couple of days, not a few days; I specifically said what it was so that there was no room for not understanding. If they want to push back, that’s fine, but I, as the manager, am being very straight, and I’m stating what the impact is so that they know the domino effect of issues those actions caused. 

Listen, most people aren’t coming into work looking to piss you off. Sometimes they just don’t know or have not thought through the first or second-order consequences. Especially as an individual contributor because they can see only their own world. Whereas you, as the manager, are seeing a wider range, so it’s up to you to help them understand the impact.

via GIPHY

#4. Be curious.

The next thing you want to do is be curious. Ask some questions. You can ask clarifying questions or dive deep into questions.

Asking questions opens the door to a conversation rather than just talking in front of them, which could make them feel attacked. It also gives way for you to listen, which we know is one of the most important things a person can do in a conversation. Listening could give you insights as to why something might be happening or why it happened – this is not to excuse the behavior; it simply gives you a better understanding. 

Having difficult conversations with employees takes work; just remember to prepare yourself mentally, choose your words wisely, clearly explain the purpose of the discussion, be specific about the issue, and foster dialogue by asking questions. These four tips will help handling difficult conversations with your team members effectively, strengthen relationships, and promote a positive work environment. Let me know in the comments if you’ve experienced these situations and how you handled your tough conversations.

Before you go, don’t forget to download the free guide: The Ultimate Team Leader Guide it will help you to lead well and effectively in your new role as people manager.