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The one question every leader should ask before having a difficult conversation


Constantly changing, complex environments often require leaders to step into challenging conversations that are often crucial to sustain relationships, drive performance and ensure good organisational outcomes. In this article, two of SMG’s most accomplished executive coaches—both specialists in leadership behaviour-change—address why we label some conversations as “difficult”. They offer guidance on how to mentally and emotionally prepare for a challenging conversation to maximise its success.

When applied to a workplace conversation, the label ‘difficult” is highly personal. A conversation one person worries about will be a situation that holds no fear for someone else. Some leaders may find negotiations around their own salary and benefits easy but struggle to manage difficult clients; others may be strong in providing feedback about work performance but uneasy setting personal boundaries with peers.

No matter what situations earn your “difficult” label, if you enter that conversation with the assumption or mindset that it’s going to be hard, your body language and outward projection will tell that story before you start speaking. You’re already ready for battle – and this is more likely to result in ‘battle’ outcomes: a win / lose structure rather than delivering the best possible outcomes for both parties.

So even the act of labelling a conversation as “difficult” in your mind is a signal that there is work to do in order to set yourself up for success.

The one crucial question to ask before having a difficult conversation

The one indispensable question to ask before having a difficult conversation is: Why have I applied the label of “difficult” to this conversation?

Answering this question allows us to go beneath the surface of our instinctive reaction and understand what is driving it. The answer will give you valuable information and allow you to understand your trigger and unpack your reactions. That, in turn, gives you the opportunity to enter the conversation with more self-awareness and provides the ability to manage your own emotional responses more effectively.

The answer to this question is often bound up with some kind of fear, anxiety or worry. These emotions can be triggered by issues including:

  • Discomfort with conflict
  • Anticipation of negative reactions or consequences
  • Fear of damaging relationships
  • Worry about the implications of the conversation
  • Apprehension about the need to be vulnerable or ask for help
  • Unease about dealing with strong emotions
  • Anxiety around how power dynamics may play out
  • Fear of rejection or fear of being misunderstood
  • Worries about feeling judged
  • Feeling insecure at the prospect of not being in control

Notice the story

Whatever the base fear or anxiety that has led you to label this as a ‘difficult’ conversation, the next step is to notice the story that you are telling yourself to support and justify your emotional reaction.

  • Are you anxious about conflict because you’ve had previous conversations like this that have not gone well? (“I tried this before and I had a bad experience”)
  • Are your feelings being triggered by emotional histories? (“My father used to criticise me and that made me feel belittled. I don’t want to make anyone else feel that way.”).
  • Is it a limiting mindset? (“I’m not important enough to have this conversation – no-one will take me seriously.”)

No matter what the story is, take the time to examine it. While you do that – name the fear and acknowledge and honour the story. Accept and be grateful for the experience that has led to your emotional reaction as an opportunity to understand and change the script.

“When we have the courage to walk into our story and own it, we get to write the ending.”

Brene Brown, Dare to Lead


In the late 1970s, Prochaska and DiClemente developed the Transtheoretical Model of Change (TMC)[1] to provide a framework for patients who were trying to give up smoking. The model has also proven to be a powerful tool for any complex or challenging decision that results in action.

Unless this is a conversation that you have no choice in having (you’ve been directed to have or it’s a part of your role), now is the time to allow yourself a period of contemplation. Grant yourself the time to weigh up your feelings about whether you actually need to have this conversation at all. Be open to both options and allow yourself to stay in an ambivalent space until you feel clear about your decision. Sometimes, when we fear the conversation, we avoid thinking about it. Remember, contemplation is not a commitment! You will feel better if you give yourself time to think about it and be honest with yourself.

Objective analysis

Switching from feeling an emotion about a situation to thinking strategically and analytically can help you think more clearly and be more objective about yourself and the situation.

List the current circumstances that are different from your fearful ‘story’. Think about your intentions, your agenda, consider your awareness of yourself and of others, and your relationship with the person with whom you will have this conversation.

Now with your strategy in place, complete a mini risk analysis to understand both the level of risk and the likelihood of the risk occurring in this situation.

  1. What is / are the risks of having the conversation? Name all the risks you feel, no matter how irrational or unlikely, and the level of risk for each. For example:
    • Are you worried that your project will be impacted? Would this be a massive impact, or negligible?
    • Are you anxious that you will lose the support of the other person? Would this impact your career in a significant way?
  2. How likely is it that these will eventuate? Taking into consideration all the work you’ve done on how different this situation is, assign a likelihood to each risk.
  3. What is / are the risks of NOT having the conversation? Name all the risks you can identify, the level of risk for each, no matter how irrational or unlikely.
  4. How likely is it that these will eventuate if you don’t have the conversation?

Of course, timing plays into this decision as well. Although ‘going in hot’ is never the best idea with conversations that have triggered strong emotions – allowing too much time to pass makes it difficult for both parties to recall specifics and develop a clear action plan together.


If you decide you do want to have the conversation (or if you have no choice in the matter), now is the time to prepare.

As much as possible, the goal during any significant conversation is to be present and responsive to what’s happening, and empathetic to the other person, which requires a level of emotional detachment. By preparing before the meeting, you can be clear and succinct with your messages.

  1. Develop your opening statement:
    • “My intention for this meeting is…”
    • “I’m raising this now because it is my hope that…”
    • “My goal is to make you aware and get your perspective on…”
  2. Develop a context statement for the meeting:
    • “This is the first in a series of meetings… “
    • “We’ve discussed this in previous meetings… “
    • “As you know, we’re looking at resourcing and budgets…”
  3. Note down how you will frame the subject matter – as much as possible keeping it:
    • specific and succinct
    • fact-based (and emotion-free)
  4. Identify your objective for the conversation. In an ideal world, what will you both leave the meeting with?
  5. Prepare to ask the other person for their input after you have framed the issue. And prepare to hold space for the response without interruption.

You may also need to prepare emotionally for the meeting. Note down:

  1. How you want to feel going into the meeting
  2. How you plan to get yourself into that emotional state
  3. What might throw you off, or trigger you within the meeting (hint: this will often link to the story you have been telling yourself)
  4. What to do if that happens
  5. How you want to feel at the end of the meeting

Mitigating the risks of emotional triggering

Key strategies to help you manage any emotions that may be triggered in the meeting:

  • Breathe deeply – give yourself time to take a few breaths
  • Notice your body, and what emotions are surfacing
  • Try to be composed and empathetic to other feelings in the room
  • Tune into the other person – really listen to understand
  • Allow space for the other person to contribute – to make it a real conversation
  • Remember to come from a place of curiosity – ask open questions


Once you have completed the preparation, with the understanding of the story that has driven your fear/ anxiety, you are ready for action.

Come to the meeting with a clean slate, without any assumptions about how the other person may react. Allow yourself and the experience to be feel fresh and new.

Your preparation should have led to a good start to the meeting. You will have been clear about your intention, set the context and framed the issue clearly. You will have asked for input and been open and have listened to the response.

By the end of the meeting, ensure that there is a clearly communicated plan of action, with commitment to both sides. Be aware that this may be different from your initial objective for the meeting, based on the content of the conversation.

If the other person is shocked or has a strong emotional reaction to the conversation – be aware that they will not be able to do their best thinking, as their brains may be awash with the stress hormones cortisol and adrenaline. Agree on next steps after they have had time to process the news. Either way, leave with a commitment to a next action. People sometimes feel so relieved that they have faced into the ‘difficult’ thing, that they forget to commit to the actions that will improve the future state.


After the meeting you may well be feeling a sense of relief, and sometimes surprise that it went so well. Many people take a deep breath and move on at this stage. However, a short period of reflection – of considering what went well, what could be improved, how you might do things differently next time – will help you affirm a more positive story in your head so that at some stage you may not even apply the ‘difficult’ label to this type of conversation at all!

final thought

Everyone has conversations or situations that they find stressful, and even after doing the work to understand the fears and the stories they are telling themselves, it’s still a difficult experience.

The only way you can get better at managing these feelings is to feel the fear and do it anyway.

Build capacity and skill by practicing and reflecting on what worked, and what didn’t.

Always start by asking yourself the important question: Why have I applied the ‘difficult’ label to this conversation?


[1] Prochaska, J. O., & DiClemente, C. C. (1983). Stages and processes of self-change of smoking: Toward an integrative model of change. Journal of Consulting and Clinical Psychology, 51(3), 390–395.

Janet Horton, Executive Coach, SMG

Joanne Lum, Executive Coach, SMG


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