A 4-Step Framework For Mastering Difficult Conversations at Work

Influencing people who don’t agree with you can be frustrating.

I was reminded of this insight last week after talking with my ex-partner about high school options for our children. I went first in the conversation, and in my view, my logic was sound, inclusive, and thorough. Problem was, he felt like he was getting backed into a corner and became defensive. His ego kicked in. I realised I was on a slippery slope and tried a different angle to influence him. It didn’t work. The conversation ended abruptly. On reflection (why does hindsight always have to be after the fact?) I could have handled the conversation differently, which has been my inspiration for writing this newsletter.

When someone has a sharply different point of view than your own, the natural tendency is to either avoid a conversation with that person or to try to convince them of your perspective (which they interpret as you wanting to be right about what you’re saying).

Neither is a productive approach.

How often do you avoid tricky conversations or don’t get what you need (or expect) from them?

A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have – Tim Ferris (Author of 4-Hour Work Week)

Everything happens in conversation

The quality of an organisation’s culture depends on the quality of relationships, which depend on the quality of conversations. While COVID has shown what’s possible – that we’re adaptive, agile and can pivot under pressure, how ‘bout when we’re not faced with a crisis and still need to create layer upon layer of change?

Even when we’re working in a great culture, people will still rationalise away their voice and go with the flow. There’s a benefit vs risk equation being continually played out. Sometimes the fear being of being wrong or judged is higher than the decision to speak up.  And even when we do speak up, our worry and fear, for example, can make us talk more than we listen. Reality is, conversations won’t always go our way.

The number of crucial conversations we have predicts the influence we have.

Leadership today is working in the shades of grey where there is no right answer, yet a right answer still needs to be found.

Tricky problems often require tricky conversations

Don’t put off tricky conversations that lead to snowballed problems. Use this 5-step framework to help you plan and have your next tricky conversation.

Key 1: Know that it’s okay to feel/be vulnerable

Acknowledge that for you, this is a difficult conversation (even if it isn’t for them). For example: “I’m nervous about having this conversation, because I don’t know how it will pan out and that leaves me feeling nervous. Please be patient as I say what I’m about to say. I’ll probably fumble my way through but I think that having the conversation is important and my intention here is….”

Key 2: Understand your thinking / feeling patterns


  • What’s this conversation about for you? (often, the problem isn’t the ‘real’ problem feeding your emotional state). What’s important to you in how this conversation goes?
  • How might your emotions be impacting your viewpoint?
  • How might your emotions impact how you talk to someone else about the issue?
  • What assumptions might you be making that is impacting your thinking? How are those assumptions helpful to you?

Key 3: Think about what’s important to them


  • What might be at stake for them in this conversation? Why might this conversation be helpful to them?
  • What expectations might they have of you or their relationship with you that might be challenged?
  • What might they want you to understand about them? What are their needs and concerns?

Key 4: Keep the conversation on track

Ask yourself:

  • How can you convey your message in a non-judgmental way so they don’t default to being defensive?
  • What might they react to what might take the conversation off track?
  • How will you know if the conversation was successful?

Bringing it all together

We all need to have difficult conversations from time to time.

The more difficult conversations you have, the easier they will become.

How you prepare for a difficult conversation matters. In short, don’t start a conversation with the conclusion you want. Co-create the conversation so you both feel heard, validated, and respected. Who knows where you’ll end up? Your conversation might lead to an outcome that’s even better than the idea or solution you came up with.

Let me know how you go with your next tricky conversation. I’m cheering you on.

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