Tricks For Nailing Tricky Conversations

| July 27, 2017 | By
Tricks For Nailing Tricky Conversations

Whether it’s delivering bad news, giving critical feedback or copping to your own mistake, tough conversations stink.

There’s the overthinking leading up to them: what’s the right way to approach this? How will the other person react?

Then there’s the conversation itself. Am I saying the right thing? Is this going to have the outcome I want?

The problem is, try as you might to avoid them, you’re going to have to have your fair share of difficult conversations as an entrepreneur. The good news is they do get easier with practice. To ensure your tough talk goes as smoothly as it can, use these tried-and-true tricks for getting through it.

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There’s nothing worse than going into a difficult conversation unprepared. In tense situations, it’s easy to lose your cool and say something you don’t mean. You might also get blindsided by an unexpected reaction from the other person and completely lose sight of the purpose of the talk.

To avoid either scenario, make a plan that starts with the outcome you want. Are you hoping to bring to light a negative issue? Change the behavior of a subordinate?

Whatever the case may be, prepare a few key bullet points you want to hit that will help you’re your case and contribute to achieving your overall goal. If the conversation starts to veer off course at any point, redirect it back to these bullet points.

Don’t Procrastinate

The longer you wait, the worse things will almost always get.

Not only is it possible that the situation will escalate while you put off a having tough conversation, but we’re firm believers in the concept of “psyching yourself out” about something. The more you overthink it, the more apprehensive you get.

As soon as you’ve decided a difficult conversation needs to take place, bite the bullet and get it on the calendar.

Be Constructive

While the old strategy of ‘sandwiching’—couching a negative statement between two positive ones—is played out as a management technique, there’s credence to the psychology behind it.

Unfortunately, negative feedback weighs more heavily on our brains and affects us more acutely than positive feedback. And yet, employees that receive regular positive reinforcement are more productive, engaged and likely to stay with the organization than those that receive mostly negative feedback.

Minimize negative collateral damage by doing your best to keep the tone of the conversation constructive, rather than critical.

This doesn’t mean you have to provide false praise or hide your true message. If you’re addressing poor work performance, for example, you might open the conversation by expressing your appreciation for the person’s efforts or highlighting one of their strengths before switching gears toward the negative.

Once you’ve made your point, end the conversation by focusing on solutions. Discuss how you’ll move forward to resolve the situation and, if applicable, offer your support for making change happen.


Though we often don’t realize it, our breath dictates so much of our physicality, from the way we speak to the steadiness of our motions.

Calm your nerves and keep the conversation on track by remembering to breathe.

Before the conversation, take a few long, deep breaths to slow your heart rate and settle your mind. Then, while you’re talking, be mindful of your breathing. Pausing to take a breath before speaking will not only help you stick to the message but give you a few extra seconds to make sure you choose just the right words.

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Have you ever made up after fighting with a friend and gotten the feeling that it brought you closer together? Then you’ve seen firsthand how, sometimes, conflict can breed connection. Of course, this isn’t always the case, but it should be something to strive for.

Whenever possible, aim to find common ground and make a genuine connection with the other person as you have a difficult conversation. Finding common ground breeds “stronger, meaningful and progressive relationships,” according to studies on the topic.

You might be surprised to walk away from the conversation with a fresh perspective, a new ally or more positive feelings than when you went in.

How did you navigate a difficult conversation in your life? Share your experience in the comments below!

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