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Communication Breakdown

Difficult conversations are an inevitable part of business. But as uncomfortable as they can be, avoiding them can make the situation even worse.

Michele Chiappetta
October 28, 2019

Difficult conversations. None of us particularly enjoys those words. It’s a rare person who looks forward to having a hard discussion, especially in the confines of work. After all, it’s not like we take a class in school on how to tackle tough subjects, though that kind of thing would be tremendously useful in all our relationships.

And though tough issues arise time and time again in our lives, most people tend to avoid talking them through. There are several reasons we do so — from negative past experiences and feelings of insecurity to being afraid of what we’ll lose and worries that talking won’t help solve things. But the choice to avoid these conversations only guarantees what we’re facing will continue to be a problem, and possibly grow worse the longer we leave the issue undealt with.

It pays off to tackle tough conversations. And if you’re a small-business owner or freelancer, knowing some useful ways to handle a difficult conversation is a boon. You’ll appreciate having some skills in this area whether you’re firing an employee, letting go of a client, addressing big changes in scopes of work, violations of a contract, or any of the many other issues that can arise when you’re dealing with people.

Here are some tips from the experts the next time you’re facing a situation that warrants a difficult conversation.

Know yourself
One of the keys to handling your work relationships better is to understand what drives you. If discussing issues with a colleague, boss, or client feels hard, ask yourself why. Are you assuming the conversation will be angry and heated? Do you dislike confrontation? Are you afraid being honest will get you fired? Knowing why you feel as you do can help you assess how realistic (or not) your assumptions are, and may open up possible solutions.

Consider the bigger picture
Many times, a difficult conversation is even more difficult because there is missing information or misinformation that leads to wrong conclusions. So, before you dive into a discussion, first consider how you see the issue. Then challenge your perceptions. Are you telling yourself a story that may not be true? What questions haven’t yet been answered? And when you do talk with the other person, find out how they see the situation. If you ask and listen, you may realize their concerns are entirely different from what you initially assumed.

Plan ahead
One of the worst mistakes you can make is to leap into a conversation when you are either unprepared to discuss it, or worse, feeling emotional about it. As much as possible, take some time to calm down before having a tough discussion. And take time to consider what you want from the conversation. That way, you can aim better at your goal.

Focus, focus, focus
Our natural tendency when having any conversation is to take little rabbit trails. This tendency is more pronounced when having difficult discussions, when we may want to deflect responsibility, get defensive, or feel emotional. So, before you have the hard conversation, choose one or two things tops to focus on. Even if you want to talk about a lot of things, it’s a bad idea to do so. People hear you better, and you’re more likely to arrive at a win-win if you focus relentlessly on one or two issues at a time.

Talk about the situation, not the person
Making the discussion personal is a sure path to failure. Once you start telling the other person there is something wrong with them or that they’re a “bad person,” you’re heading away from dealing with the issue that needs resolving. If you want the other person to understand you, try to stay objective and issue-focused.

Listen well
Ah, the art of listening. It’s so underrated. Excellent listening skills pay off in many ways — from helping you come across as empathetic and caring to ensuring you get needed details that can help you arrive at a win-win. Keep in mind, listening isn’t just about being quiet when the other person is talking. It’s active. So, ask questions, repeat ideas back to the other person, and get clarification to make sure you understand them accurately.

Keep it short
The longer a hard conversation continues, the more likely it is to either get off-track or get emotional — or both. But neither of those possibilities is going to help you arrive at a solution that serves everyone. So, discuss things only as long as necessary to handle the one or two issues you’ve chosen to focus on. Don’t belabor the point. And if someone is getting tired or frustrated, go ahead and end the conversation by setting up a time to come back together later and talk more.

Be open to feedback
Ultimately, any conversation is a two-way street. And if you’re going to arrive at a win-win, you need to expect that the other person may have some feedback for you that’s not entirely sunshine and rainbows. If you’re planning to say something tough, expect to hear something tough in return. Beyond that, try to see it as a gift. It’s not all the time that you get information that can help you grow in your work and as a person. Take the feedback for what it’s worth. Even if you don’t agree, listen respectfully. And use anything productive to improve your career and your relationships.