Ariella Sassover

Hard conversations are easier if you go in prepared

Decide what you want first, and don’t be afraid to postpone.

October 9, 2017

Everyone has those moments when they are completely stumped for words.  You know them – those times when you need to express yourself and simply fumble, or say what you do not mean to say, or freeze, speechless.

Often, you are later hit with the perfect response that you should have said – leaving you frustrated, annoyed and without having communicated your thoughts properly.

What happens when what you say can be the difference between having your needs met and suffering and you misstep the fine line between assertive communication and attitude?

At one time or another, it’s a struggle for all of us. How do we get those around us to truly listen to what we are saying? Simply put, how do we ensure that we both listen and are heard?

Here are some ideas to get you through those moments, planned or unplanned. Memorize it when they’re not happening and you’ll be prepared when they do.


Assess what your goal is. Do you want an extension on a test, for your parents to stop waking you up by banging pots and pans, or to apologize for a rude comment?

If you do not know your goal – if you are coming into a conversation with a feeling of vague discontentment – you should spend more time assessing what the problem is. Maybe you just want someone to validate your discontentment; this can also be a concrete goal. But if you do not know what you want from the conversation, it is very likely that the person you are talking too will not know either.

Once you have established exactly what you want from the conversation, make sure to envision – and write down – a list of all that your goal entails. This way any question directed towards you about specifics can be answered before the conversation.

For example, if your goal is to have your parents wake you up in a more pleasant manner, give them ideas of how you would like to be woken up. You want them to feel as if you are working together to find a solution. You don’t want them to feel like blame is being placed upon them and that it is their sole responsibility to ensure your relationship remains balanced and good.

Although that might not seem important when asking for a small compromise, when in a relationship with someone, there will usually be more than one instance of contention, and it is important to set a precedent of respect. This is so that when you need to have a serious conversation about something bigger there is a basis of how you approach conversations.


When you raise a problem you are having, they may raise one they’re having too.  Be careful with your tone, and the right mood will be set.

Set aside a time to converse that works for all parties, and if you need to reschedule, don’t be afraid to. As long as the mood is infused with a willingness to effectively communicate it is a good time to start the conversation.

Remember that every conversation is a two-way street, and as the famous Greek philosopher Epictetus said, “We have two ears and one mouth, so we can listen twice as much as we speak.”

Although this might be a tough standard, it is very important to listen to what is being said to you – especially because it is easy to get caught up in your own head and what you want from the conversation.

Listening helps you understand the other person and can help you react in a way that will be heard. This means that if you hear why your parents bang pots and pans and why they do not want to stop, you can give a counter-argument that respects their reasoning and addresses its flaws.


Stand fast to your boundaries and morals while still remaining flexible. This balance is probably the most difficult to address successfully. We must respect our limits and be honest, while validating and compromising when it does not cross our own values. Knowing the difference is something that just takes time and thought.  Therefore…

Take your time. You should not feel afraid or embarrassed to take time to process and think of your response before speaking. There is no need to blurt out the first thing that comes to mind.

When you are conversing in a respect-filled environment – as opposed to in a fight – there is no rush to get out what you need to say. In fact, when you show that you are taking the time to think before speaking, you show maturity and an honest investment in the conversation.

A first step to any effective communication can be to evaluate your emotional level.  In the book Dbt® Skills Training Handouts and Worksheets, the psychologist Marsha Linehan divides emotion into levels, one through 10, with one being the calmest and 10 being the most extreme.

When your emotions range in intensity from 4 to 10, she says, it is unlikely that your communication will be well thought out and successful.  Better to reschedule your conversation for later – which means not being afraid to say the time’s not right.

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