Mastering difficult conversations

Are you putting off having a difficult conversation with one of your team or a colleague? Perhaps it is to address poor performance, give feedback about behaviour, or even to let a supplier know they haven’t won this years’ contract.

If you are nodding with acknowledgement then let me reassure you, you are not alone. Difficult conversations are a common and integral part of leadership.  

Although challenging conversations can be uncomfortable at times, crucial conversations are likely to result in increased awareness and solve problems.

The question is, what is the best way to approach them?

Although it can be tempting, burying our heads in the sand in the hope it will resolve itself, rarely works. As Raymond Hull once said, “peace of mind is attained not by ignoring problems, but by solving them”.

Sweeping issues under the carpet can lead to a build up beneath the mat – one we are likely to awkwardly trip over eventually.

Similarly, using inappropriate communication methods for these crucial conversations can result in misunderstandings. Hiding behind the security of an email may not be conducive to addressing the matter –  after all, it is called a ‘conversation’ for a very good reason.

Difficult conversations are an integral part of successful leadership.

Difficult conversations are an integral part of successful leadership.

Here are my top five tips to approaching difficult conversations:

1.  Preparation and reflection. Ask yourself the following questions:

  • What will be the unintended consequences of not having this conversation?
  • What am I trying to achieve with this conversation? 
  • What is my desired outcome? Be honest with yourself about your motives.
  • What are my own attitudes or history towards this person or situation that may be influencing the conversation.  
  • What is my ‘backstory’?
  • What are my own needs and fears around this conversation?
  • What will it be useful for me to know or consider about the other person prior to embarking on this conversation?

2.  Intent.

In the book Crucial Conversations, the authors talk about cultivating a positive intent focused upon curiosity and discovery. It is as important to understand, as it is to be understood, therefore the intention should always arise from a positive starting point.

3.  Body language.

Research has shown that between 60 and 70 percent of all meaning is derived from nonverbal behaviour.  Give full attention to voice tone, body positioning, hand gestures, and movement to produce body language which is calm and non-threatening.

4.  Practice.

If unsure about how to best approach the situation, then practice the words – both mentally and with a trusted other.  This will provide a sound testing platform, where we can become familiar with the words, and what they feel and sound like.  It is also a great opportunity to obtain feedback about what it’s like to be at the receiving end of the conversation.

5.  Don’t necessarily measure the success of your conversation by the immediate response.

Sometimes a person’s initial response will be anger, defensiveness, hurt or tears.  This can be tied up with the fight or flight response.  If this happens, do not take it personally.  Often, people require time for reflection – after which their response is more likely to have been considered and not driven from heightened emotion.  Providing time and space for them after the initial discussion and then ‘checking in’ with them is also wise if emotions run high.

What tips do you have for approaching difficult conversations?


  1. […] tough decisions and crucial conversations am I willing to have in order to achieve […]

  2. vincent cornelius on May 29, 2013 at 6:37 pm

    Thank you for an interesting and detailed post Suzi. I’m running a leadership and management workshop on this topic at my university on Friday; I will provide the group to a link to this post.

    I find it useful to think of five typically ‘difficult’ conversation types, each with a slightly different strategy:
    * Providing feedback
    * Conveying ‘bad news’
    * Getting past ‘no’
    * Gettting to ‘yes’
    * Refusing a request

    As Shakespeare wrote in Hamlet – “There is nothing either good or bad but thinking it makes it so”; even though some conversations are easier to manage than others, the act of thinking a conversation is (or will be) is very likely to make it so.

    • The Leader's Digest on May 30, 2013 at 9:55 pm

      Hi Vincent,

      Thanks for your comments. I really like your classification of 5 sorts of ‘difficult’ conversations – you’re so right, each one will have a slightly different approach. Sounds like a great workshop! Thanks for the link.


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Suzi McAlpine

Suzi McAlpine is a Leadership Development Specialist and author of the award-winning leadership blog, The Leader’s Digest. She writes and teaches about accomplished leadership, what magic emerges when it’s present, and how to ignite better leadership in individuals, teams and organisations. Suzi has been a leader and senior executive herself, working alongside CEOs and executive teams in a variety of roles. Her experience has included being a head-hunter, an executive coach, and a practice leader for a division at the world’s largest HR consulting firm. Suzi provides a range of services as a Leadership Development Specialist, including executive coaching, leadership workshops and development programmes for CEOs, leadership teams and organisations throughout New Zealand.

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