How to have difficult conversations

Difficult conversations. Maybe your boss yelled at you during a heated discussion; or your friend didn’t talk to you for a few weeks; maybe your brother decided to hang up the phone on you. Tough conversations are not to be avoided as they can cause more harm in the long run. Instead, learning to handle difficult conversations in a way that makes it most productive for yourself and the person you are talking to is a skill that will increase your social effectiveness (i.e. how well you communicate with others).

In this article I’ll review 7 tips that will help increase your fluency in having difficult conversations.

Consider the following example:
You own a small business and one of your employees, Nancy, has been performing poorly for the past few months. She’s undergone training and has not made any improvements. You want to have a conversation with her to tell her your side of the story; she’s not performing well, you’d like to understand her perspective and possibly let her go.

Keep the objective in mind
The first thing to do is to ensure you have the objective in mind. By keeping the objective front and center in your mind, you will be able to focus on the important aspects of the conversation and ensure you say what’s necessary.

  • Why are you having the conversation?
    • To talk to Nancy about her poor performance
  • What is the outcome you want?
    • To understand her side of the story and possibly let her go

Separate Objective vs. Subjective
Separate facts from your thoughts and emotions.


From the table above, facts are separated from thoughts and emotions. This allows the conversation to be focused on facts and observations rather than on your thoughts and emotions towards the situation at hand. In the example above, implying that Nancy is performing poorly because she’s distracted at work is a thought unless Nancy says so herself.

Calm your mind
Having a difficult conversation requires a lot of concentration and is taxing on your mental energy. Often times you might find yourself building up a situation in your head with outcomes that are unlikely to happen. Take a step back, breathe and focus on why you have to have this conversation. In this example, the profitability of your company and the productivity of other employees are at stake. Nancy’s low performance might affect her co-workers in negative ways. Mindful breathing is a great way to stay calm and centered. Click here to read about how you can practice mindful breathing.

Speak slowly and clearly
Difficult conversations are almost always important conversations that must be done. Ensure your message is effectively communicated by speaking slowly and clearly. To increase the effectiveness of your communication, avoid the following when having a difficult conversation (and in speaking in general):

1. Hesitation words

  • “um”
  • “err”
  • “ah”

2. Diectic language – generic descriptions without detail that cannot be understood without context

  • “I want to talk to you about that thing we discussed that day” instead of saying “I want to talk to you about your performance trend and continue our discussion from where we left off on Monday afternoon”

3. Overly formal language

  • “Therefore”
  • “Supposedly”

4. Tag questions – Adding mini questions to statements to ‘soften’ the blow

  • “Your performance is low, don’t you think?”

5. Intensifiers – overuse of adjectives/adverbs that add no value

  • “It’s very, very distressing to see this performance trend” instead of saying “It’s distressing to see this performance trend”

6. Hedges – making statements less direct

  • “I guess”
  • “Kind of”

Be comfortable silence
There will be moments in the conversation where a silence occurs. Do not rush to speak just to break the silence. Silence allows the person listening to your message to process and let it sink in. Extroverts tend to be uncomfortable with silences and are used to thinking while speaking. This can be perceived as steamrolling or forcing a conversation if the other person is an introvert. Introverts on the other hand, want to think before they speak. Stop talking after delivering your message and give the other person a chance to reply. If they are taking a long time (more than a few minutes), you could simply say “I don’t know how to interpret your silence, did you understand what I just said?” This will prompt them to explain that they’re processing, or thinking and confirm they understood the situation.

Ask the other person for their point of view
Starting the conversation and stating the issue a good way to start a difficult conversation. The next part is to inquire and ask the other person their point of view. By separating the facts from your thoughts and emotions, the other person will be able to explain the facts based on their point of view. Continuing the example, Nancy reveals that she’s been overwhelmed with the amount of work and is unable to prioritize on her own, because all her projects important because assigned to her from different VPs in the company. This information is helpful since it gives you insight into the problems the other person is facing.

Find ways to be constructive or suggest other solutions or alternatives
Hard conversations are centered around issues that we would like resolved one way or another. Stating the problem at hand is important, but equal importance must be placed on the solution to resolve the problem. Always have a solution or solutions to the problem you are about to bring up.

After hearing Nancy’s side of the conversation, we know that the training needs to be focused on prioritization and managing expectations with her VPs. If this is unsuccessful she can be transitioned to another role or let go. After stating the problem, expressing your point of view, hearing her side of the story, the final step is to come up with solutions to move forward. Creating a two way discussion instead of a one way lecture, helps both parties express their concerns, and find middle ground.

These are my 7 tips for having difficult conversations. How do you have difficult conversations? What was the last difficult conversation you had? If you’re feeling brave share in the comments section below!

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2 Comments, RSS

  1. Razi March 6, 2017 @ 23:18

    My last difficult conversation is with my son. Although he said sorry he didn’t want to do anything to improve the decorating warmath between us or communicate effectively regarding what went wrong. In this situation what do you suggest.

    • Azfan Jaffeer March 21, 2017 @ 23:40

      clearly define the objective situation from the subjective situation. separate your thoughts and feelings from your observations and communicate this to your son.

      For example:
      Your son is calling home less frequently, and this makes you think and feel that he doesn’t care.

      fact: son is calling less
      thoughts: i think he doesn’t care
      feelings: i am hurt

      now that the components are separate, you could stitch them together in the following manner:
      “Son, I noticed you are calling home less. This makes me think that you don’t care about me and makes me feel hurt. Could you explain your perspective?”

      This clear expression of the problem and asking for another perspective should clarify things.

      Good luck!

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