August 5

Follow These Coaching Guides to Handle Difficult Conversations

What does a difficult conversation mean to you? When was the last time you had a difficult conversation with your people at work? And how did you handle it?

Difficult conversation often relates to delivering unfavourable news or message. Poor performance, attitudinal change, layoff, denied promotion, change of working rules, turn down of a request, and many more, you name it.

It is more than just telling the news. The news you are telling can possibly affect the person's emotion state, well-being or even disrupt his career advancement. IF you have overlooked the human psychology aspect, you could end up with an unpleasant experience for both sides.

In the same context, if you bulldoze your way in the conversation, you are likely experiencing resistance, backfire, and possibly communication breakdown in the process.

Difficult conversation can be quite daunting and relationships damaging if it is not handled well. So, what is the best way to handle it?

Search around you will realise this is not a new topic. Books, journals, articles, and online reading materials all advocate different recommendations, strategies, and solutions handling it. One of the interesting articles I have read recently is, Daisy Wademan Dowling on her HBR's article: HBR: 7 Tips for Difficult Conversation shares some useful tips that are worth trying. And some of these tips are indeed related to coaching skills.

Someone once said to me, coaching is not the sole approach used to handle difficult conversations. Totally agree. But if you do it right the coaching way, you will gain tremendous positive outcomes in the conversation.

The next time you have a difficult conversation to manage, try the following guides:

Yes, it starts with the end in mind. Know what you want to achieve out of the conversation. Plan your communication strategy. Get to know what communication style will help you create positive outcomes in the conversation.

Ask yourself these few questions:

  • 1
    What do I want to achieve by the end of the conversation?
  • 2
    How will I know if I have achieved it?
  • 3
    What will help me to create positive outcomes in the conversation?
  • 4
    What will encourage him receive the news and speak with open heart?
  • 5
    What do I need to watch out in the conversation?
  • 6
    What action do I want him to take after the conversation? 

In difficult moment, people tend to seek out for feeling safe, accepted and supported by others. Earn your trust no matter how close the relationship you have with the person. Show your genuine interest, validate thoughts and feelings, and give unbiased feedback. If you do them well, you are building a deeper level of trust with the person. And the effect is reciprocal.

Ask yourself the following questions:

  • 1
    What are my unconscious biases?
  • 2
    What I need to do more so that he won't shut his mind?
  • 3
    What is the best communication style to create an inclusive conversation?
  • 4
    What will I do more making this conversation easier?
  • 5
    How can I stay non-judgmental and be unbiased in what I say?
  • 6
    What behaviours or actions of mine will hurt the conversation? 

Many difficult conversations turn futile when emotions overpower everything in the process. The conversation stays fuzzy and heated. It ended with no conclusion of concrete solution or forward action plans. If this happens, it will be good to end the conversation for the time being. Find another time come back and continue the conversation again. But before you go for the second round, spare yourself some private time and evaluate what really happened in the conversation.

Can it be the end goal (Guide #1) still not clear and specific to you and him? Or you paid too much attention of wanting to achieve the outcome and made light of giving him some space for self expressions? Or perhaps you were not assertive enough making your points clear, and unable hold him take responsibility seriously to implement the agreed-upon actions.

Ask yourself the following questions:

  • 1
    What was really missing in the conversation?
  • 2
    How will I do it different next time?
  • 3
    How can I hold his attention on what is important for him?
  • 4
    What will I do to support him take actions moving forward?
  • 5
    What will encourage him to take the first step and do it?
  • 6
    If it still does not work out well, what is my next course of action? 

No one can predict how the actual conversation will be. But, if handled well, he will feel better with by taking positive actions and move forward after the conversation.  

And the coaching approach has what you need to make the conversation easier and beneficial to both sides. Having said that, knowing these techniques will only do good for your knowledge. It makes no difference to your ability to handle the conversation, unless you apply and refine your skills of doing it.


coaching, difficult conversation, guide, staff

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