Leaders Often Have Difficult Conversations…Here’s How to Have Them Successfully.


Share on LinkedIn

Having difficult conversations is one of the hardest parts of being a leader.

It’s emotionally charged (for both parties, my stomach would often also be in knots), we worry how it’s going to go (will I say the wrong thing, not get my point across, or OMG what if they cry, or worse…get really defensive), so rather than face that, we sweep it under the rug instead. The fact remains, as the leader, you have the responsibility of having these conversations, for everyone’s sake.

This difficult task fall under your territory, so, since that is the case, let’s tip the scales in our favor shall we?

What to consider…

Timing: for me, I would have these at the start of my day. The obvious reason is that I wanted to get it off my plate, plus, I would have my MIT (Most Important Thing) accomplished. The second reason I used to do this first thing may surprise you. I want to see how this person responded to our discussion. Be the example here and carry on the rest of the day without judgement, a grudge, or an air of awkward disappointment. I was always curious to see if they could do the same, it just tells you a lot about a person, that’s all.
But remember…you go first here.
If it is emotionally draining for them, do your best to let them take the rest of the day off. If they were passed up for a promotion for instance, it’s gonna hurt, and they will really appreciate having the option to remove themselves for the day to process.
Sometimes, the best time for you both is the end of the day. Where most of the team has left, it’s quiet, and they can leave without ‘being seen’. It’s all dependent on what is being discussed, with whom, and your take on the most effective or kindest timing for this talk.

Emotions: when you have a conversation with someone who takes what you say to heart, is open to learning and improving, then you really don’t have to worry about much here. They may be bruised, but they will carry on. BUT, there are always the extremes, you know your team, be prepared for that person’s response.
And take note if this becomes a pattern they cannot break, it may be a red-flag for this person. Emotional outbursts can sometimes be considered passionate, but more often are a sign that they cannot self-regulate their emotions. It’s a display of immaturity and a lack of self-awareness. That’s the kind of baggage leaders and their peers do not want to contend with.

Sensitive (crying): be supportive and show compassion. There’s not much you can do except for that. If you are not comfortable around this, then whoever you choose to be included in the conversation (more on this in a sec), they need to have that skill.

Anger: First, as you know, don’t engage in this behavior. If you know this person typically responds defensively, how can you diffuse this? There’s something that happens to an excuse when it is said out loud and the receiver (you) just let’s it hang there. It loses a lot of steam, a lot of its punch. The two of you can usually feel how hollow it is.

Completion: To close, review established expectations so they are crystal clear, remind them of your support, and have an agreement in place to move forward.

Last Rule…and yes, rule. A hard and fast one at that.

There must be 3 people in the room. Never, ever be just the 2 of you. This is for your own protection. You need to avoid any ‘he said-she said’ situations, you need to have a witness. Plus, sadly, you never know what may come forth in this day and age and you literally just need someone else in the room to be on the safe side (a supervisor, definitely not a peer). Now, the bonus is that if you have an up and coming leader in there with you, they will learn TONS.

If you really want to get this right:

Let’s back up and start with you. Whenever there is a situation and I want to be considerate and mindful, I not only prepare myself tactically with the facts, but I take the time to mentally prepare as well. And it has served me very, very well.

Admittedly, I’ve often times winged it. And that has turned out fine, but I feel I get even more out of myself, or in the past my team, when I take some time to consider the following questions:

1. What do I want to happen (come out of this)?

For instance…this post. I want to help you have a strategic way to approach difficult conversations, I want to provide a structure. Answering this helps clarify the end result and sets my sights on it.

2. How can I best make this happen (set this up for success)?

Look at what controllables I can influence that will affect the outcome. In the case of difficult conversations here are a few I can think of:

Environment: most likely your office is a great place. It’s quiet, private, provides a level of seriousness that allows for a focused conversation. Sometimes, depending on who I would be talking to, I may choose neutral ground. Go with that person for a walk or out for a cup of coffee. This can take some of the perceived embarrassment off the person, something to consider when they are part of your intimate closer circle.

Examples: people learn when they can connect what they did to what you are talking about. Be prepared with examples to help them connect the dots. Plus, you can’t argue that proof helps.

3. Why is this (i.e. conversation) important?

This will give you some courage as to the importance of having this conversation. It may just be self-serving. This person could be driving you nuts, and that’s reason enough. That, in conjunction with the fact that you have a professional responsibility to yourself, your team, your company, and the work you all put forth are prime reasons of ‘why’.

By mentally preparing using those questions, the anxiety of what can be deemed as confrontational is dialed down and you can focus on how you want to show up. Again, you lead the way here, set the stage for conversation…not confrontation. This allows you to relax and help makes the conversation as successful as possible. You’ve moved your focus to what’s important, how you can impact it, and why you need to make it happen.

These conversations are difficult, and that’s ok.

Having these conversations are extremely challenging, it takes a good dose of experience to ensure they go well (this is no walk in the park!). If you go in with a clear objective and prepared, you will be successful and become more comfortable in this role. Exposing your new leaders to these accelerates their comfort level and helps them develop this skill as they watch and learn. Pretty soon, they are engaging and contributing to the conversation. This gives them practice and establishes their authority amongst the team with every conversation. Debrief with them after what was learned.

What is eating at you? What are you sweeping under the rug that you know shouldn’t be? Mentally prepare, put your big-boss pants on, and have the conversation. You will feel such a weight lifted off of you and guess what, if you don’t, the individual and team will be wondering why you are not.

Remember, difficult tasks come with the territory…and you’re the best person for the job!

Karyn Chylewski
I spent 20 years working in a diverse range of leadership roles before starting my leadership coaching practice. From working as a backcountry hut master to restaurant management, to leading a team in the intense pet care industry, I learned that the key to leadership success is all in relationships. I now help leaders build better connections with their team, navigate their relationships, and understand the human side of leadership so they can become better leaders, improve team morale, and achieve higher performance. I love spending time outdoors, with my family, great wine & conversations.


Please use comments to add value to the discussion. Maximum one link to an educational blog post or article. We will NOT PUBLISH brief comments like "good post," comments that mainly promote links, or comments with links to companies, products, or services.

Please enter your comment!
Please enter your name here