Need to Have a Difficult Conversation? Here’s How to Have Them Successfully

The secret is in these 3 questions PRIOR to having the conversation.

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Body language is very telling...what do you sense the person in black is feeling just from this snapshot?

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 (and keep sweeping) 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? How can we get the most out of these and set ourselves up for a successful conversation and outcome?

Let’s start with the pre-game…
Whenever there is a situation and I want to be considerate and mindful of how I show up, this may be for a coaching client, a networking event, a meeting…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:

Here are the 3 questions to ask yourself as you approach this conversation:

  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, tips, how to’s. Answering this helps clarify the end result and sets my sights on it. In the situation of a disciplinary conversation, most likely you will want your employee to make a behavior change, to stop or start doing what is bothering you and/or everyone.

  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, and 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? 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’. You are in your role to ensure those are all being upheld.

Difficult tasks come with the territory.

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 of 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.

Final thoughts 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 would want to see how this person responded to our discussion. It’s important to close the conversation on an upbeat, positive, going forward kind of vibe. 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. (For more tips on how to lead better…click here for the 15 hallmarks of great leadership).

The Crier and The Beast

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. BUT, there are always the extremes: the overly sensitive person and the angry/defensive person. You know your team, you need to be prepared for that person’s response. Having compassion will never steer you wrong, in anything.

Crier: be supportive and let it happen. There’s not much you can do except for that. The good news is, it’s not that terrible to bear. If you are not good around this type of situation, then whoever you choose to be included in the conversation (more on this in a sec), they need to have that skill.

Beast: you know this person typically responds defensively, how can you diffuse this? Feel free to let them be heard, perhaps to offer an excuse for their behavior. 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. But, you’ve done your part and let them have that moment (don’t let this drag on).

Then, steer the conversation towards helping them see the impact of their actions, but ask them to lay it out. Having them connect the dots of their bad behavior to the impact on the team, the people that they care about and work with, almost always turns them around (and is further revealing when it doesn’t). It’s rare that when they walk themselves through the path of impact that someone will still dig their heels in and hold onto their angry response. Plus, by this point their initial wall they threw up will have fizzled. It’s typically a knee jerk response.

From here, it’s all about supporting them on what they can now do (help them brainstorm) to put their behavior change into effect.

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.

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 (those of you who are new leaders, do not feel bad if you’re uncomfortable here, this is no walk in the park!). The more exposed they are to these, the more comfortable they become with them over time and develop their own skill. Pretty soon, they are engaging and contributing to the conversation, playing an active part, which 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.

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