Leadership Matters: 5 Ways to Prepare for Tough Conversations

It seems like there are innumerable tough conversations to be had in the workplace—for situations like mediocre performance reviews, cancelled projects, peer feedback and so on. The five tips below will help you prepare ahead of time, so you’re positioned for better outcomes more often.

But before we get into the tips, there’s a type of tough conversation that deserves special mention: tough conversations that never happen. These tend to be conversations that aren’t required in the strictest sense, but they often have great potential. After all, a cancelled project must be discussed, but telling someone that their body language makes them seem disinterested is a conversation that could, but shouldn’t, be avoided. The tendency to avoid or postpone can be especially strong when the subject is something personal or embarrassing. If you’re thinking, “I’d want to know if it was me,” then remind yourself that the conversation is a gift—not a burden—that you can bestow.

Also, a word about timing. In most cases, issues that call for tough conversations should be handled sooner rather than later. However, use common sense in scheduling ample time to have the conversation and to process it. For example, timing it right before a stressful presentation wouldn’t be ideal.

Now for the tips. There are a variety of skillsets that are helpful in having tough conversations, but preparation is one of the keys.

1. Practice Makes Better

The more tough conversations you have, the easier and less uncomfortable they will become. Just like any other skill, repetition usually leads to improvement.

• Don’t expect every conversation to go perfectly, but do take time afterwards to think through how it went and what you could have done differently to make it go better. Remember you’re building skills, not just trying to survive.
• Roleplay can be extremely effective because it helps you practice a specific conversation ahead of time. Enlist someone to play the other person, then switch roles. The conversation won’t go the same as the roleplay, but it’s invaluable for deeply considering different points of view.

2. Clear Objectives

Get as clear as you can about why you’re having the conversation and what you’re trying to accomplish. Writing it down for yourself can help keep the discussion focused, as these situations have a tendency to go in unexpected directions. For example, if someone is consistently missing deadlines, an objective could be to encourage them to reprioritize so they can get more things done on time and support the organization in moving on its strategy more quickly. This will result in a different conversation than one where the objective is to get the person to communicate better and sooner about roadblocks so they can be handled more quickly and efficiently. Different still is the conversation when the objective is to communicate the seriousness of the issue, find out what is causing deadlines to be missed, and decide on actions to take.

3. Stick to the Message

Now that you’re clear on the objectives, decide on the message you want the person to receive. Thinking about this in advance increases the chances of the message landing the way you want, even though it’s not completely in your control. Don’t dilute the message during the conversation. Confusion can creep in when people attempt to soften the blow or broaden the conversation with other messages.

• What is the desired minimum outcome of the conversation and what is the ideal outcome?
• What tone should you use as you deliver the message? As noted above, delivering a tough message in an overly soft tone can be confusing; likewise, an overly harsh tone may also cause the message to be lost in the delivery.
• Clarify the points you want to make to support the message. Think about the essential facts, events, timelines, etc., the person needs to know and make sure any supporting information or examples are at your fingertips. Stick to your strongest points—quality examples over quantity is key. Also identify questions that you want to ask. It’s not unusual to have some missing information that needs to be filled in.
• Think through what questions the other person might ask and what points they may make.
• Identify any nonnegotiables ahead of time so there isn’t confusion. If the person is being transferred to a different position and that decision won’t be changed, it’s best to be clear about that from the start.
• What potential solutions or action plans are you prepared to suggest?
• What do you need to see and hear from the other person that will let you know they are clear on what you are trying to communicate?

4. Be Curious

Tough conversations are typically tough because you think—right or wrong—that the other person will find it hard to hear what you have to say. This means that you may be on different pages, which makes it critical to be prepared to listen and be open to what they say. It could change your mind. Be curious so you can learn and see the situation through a different lens. That said, keep the non-negotiables in mind.

5. Emotions Check-In

Take a moment to consciously think about your emotional state prior to the conversation. Check in with what’s happening in your body, too, since that’s a reflection of your emotional state. The idea isn’t to eliminate emotions but to be aware of them. A check-in may reveal that you’re nervous because you don’t want the person to dislike you. It’s good to know that this is a source of your discomfort. Acknowledging it can help put it into perspective.

Also, think about how you want the other person to feel during and after the conversation. Recognize that you don’t have control over how the person receives the message or feels, but thinking about it in advance and being intentional in the delivery increases the chances of a better outcome.

Regardless of the reasons for your tough conversations, these five preparation steps can help bring more successful outcomes. The conversations won’t always go as planned, but with preparation and more practice, the better and less uncomfortable they will be.

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