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A Steady Space

How To Start A Challenging Conversation

Davina Hehn
Davina HehnPublished on July 20, 2022

Nothing seems more difficult than starting and having a challenging conversation with a successful outcome for both sides. And while many intelligent people are willing to communicate, get down to the real issue and find a solution for it, most of them find themselves absolutely stuck and paralyzed when they have to initiate a challenging conversation.

How to overcome the fear of starting a difficult conversation? Stay with us and learn how to communicate effectively with A Steady Space!

If you want to become a good communicator, you first have to identify what you’re dealing with!

In this article, we are talking about challenging or difficult conversations.

What exactly is a challenging conversation? How can we define it? Someone may say that it’s subjective – what’s challenging for someone, isn’t difficult at all for someone else.

But is it really so? There are some criteria that need to be fulfilled so that the conversation topic may be listed as “challenging”.

Usually, a challenging conversation may include some or all of the following elements.

  • A subject you don’t want to talk about
  • Conflicted opinions on both sides
  • Uncomfortable topics for discussion
  • A situation where you’re not sure what you should say
  • A high potential for conflict

We often make numerous excuses to avoid difficult conversations. Some of the most common ones include phrases like this:

  • “Now is not the right time, perhaps I should wait.”
  • “I don’t want to hurt their feelings.”
  • “It will definitely escalate into conflict; I’d better avoid that.”
  • “If I wait long enough, the problem will just go away.”

Have you ever used some of them? If you did, you already know that they don’t work at all. There is no point in delaying the inevitable, so the sooner you face the issue, the sooner you can find a pathway to effective and successful communication!

The reason most of us are scared and reluctant to initiate this type of conversation is simple: we feel like we have only one chance to get our message across and don’t want to ruin it.

That insecurity breeds fear of saying something wrong, fear of rejection and more often than not, it results in avoiding the complicated topic altogether, which is not healthy at all! Delaying, avoiding, and silence will bring no good, cause sooner or later, we all have to face our problems and address them properly.

Good preparation is everything. Before you start the conversation at all, you should ask yourself some really important questions, such as: Why do you want to have this conversation, what do you hope to achieve in the end, and what’s the most realistic final outcome you can expect.

When preparing, think very carefully on these questions, they may ultimately decide the outcome of your conversation:

  • What is the purpose of the conversation?
  • How do you think the other side will react and behave?  
  • What constructive suggestions can you propose to solve the problem?
  • What kind of outcome do you expect?

If it helps you, you can write down these questions and write your answers. You’d be amazed how much you can clarify seemingly unsolvable issues with just a pen and paper!

If you want to initiate a challenging conversation, you have to focus on clarification, and forget your fear of conflict. When you’re concentrated on clarification of the issue at hand, both you and the other side can approach the problem in a more constructive way and easily find a common ground.

Have in mind that although difficult, challenging conversations can be beneficial for any relationship. If you can’t initiate any conversation (no matter how tough it is), you won’t be able to communicate your needs, issues, or feelings to the other side and get an insight into their point of view. You’ll be stuck in a stale, avoidant communication mode, and that doesn’t contribute to clarification or better communication. Worst of all, you won’t resolve any of your problems, and if you’re reading this, it’s safe to say that’s not the outcome you really want.

If you follow the upcoming guidelines, very soon you’ll master the art of having any conversation, even the most challenging ones!

Good timing can make a huge difference in your communication – for the better!

It is essential for any talk, even more so for difficult conversations. After you’ve carefully identified the issue you want to talk about, observe the situation and ask yourself: when would be the best timing to start?

Nobody wants to engage in a challenging conversation if they’re busy, stressed, or overwhelmed.

It is always a good idea to set up a time for discussion beforehand. Choose a timeframe when both of you are available to talk freely, without any interruptions. Even if you have a scheduled conversation, it is always recommended to ask: “Is this still a good time to talk?” before you start.

Start the conversation in a collaborative and positive tone. When you’re approaching someone positively, they’ll immediately feel it via both verbal or non-verbal communication signals, so pay attention to both your body language and your words!

Don’t start with a vague statement like: “We need to talk”. That will just stir up unnecessary panic and fear. Communicate clearly what you want to talk about and how you feel.

Here are some really useful opening lines which can do wonders if you use them in a proper way:

“I would like to discuss this problem with you. I think we might have different ideas about how to solve it.”

“Do you have a few minutes to talk? I have something I’d like to discuss with you and I’d really appreciate it if you can share your thoughts with me”.

“I’d like to talk about this problem with you, but first I’d like to hear your point of view.”

“I hope we can achieve a better understanding of this issue. I really want to hear your insight about this and share my feelings, too. Would it be OK if we sit down and discuss it on Saturday?”

Whenever you can, always communicate clearly on WHAT exactly do you want to talk about. In that way, you’ll avoid many misunderstandings.

Finally, if you really want to achieve a successful outcome, you have to be aware of many subtle and not-so-subtle signals and/or distractions which may play a pivotal role in the final outcome of your conversation.

Here is what you should always be mindful of, especially when you initiate a challenging conversation:

  • Don’t ever try to start a difficult conversation by mail or phone. That’s definitely a big “No”! Always have it face-to-face, whatever the outcome may be.
  • Pick a private setting. There is nothing worse than starting this type of conversation in a public place. Nobody is obliged to listen to your private problems, so keep them to yourself and discuss them privately.
  • Make sure you won’t be interrupted. Pick a time that works out best for both of you and during that timeframe, leave your mobile phones in another room, turn off the TV and minimize all distractions.
  • Be aware of your body language. When you sit opposite to someone, it may be perceived as a hostile act. It’s always better if you sit next to them, not opposite to them.

Yes, it can be extremely difficult to have a challenging conversation if you don’t know how to start! We hope we have helped you to navigate this unknown territory, so that you can improve your interpersonal skills and the overall quality of your communication, both in your private and/or professional life!

We’re here to provide you with solutions and guidelines to all your communication problems, no matter how big or small they might seem!

Till the next reading, remember, there are no challenging conversations, only wrong questions!

Master the art of effective communication with A Steady Space!

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