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How to Master Difficult Conversations with Compassion and Confidence

The following is an extract from Lunchtime Learning for Leaders.

What’s so difficult about a ‘difficult conversation’? If this is a topic that causes you apprehension, you are not alone! In coaching leaders, it’s the one subject that results in clammy hands and high levels of anxiety, and everyone has stories of feedback going wrong – whether being on the giving or receiving end.

If we reduce a difficult conversation to its essence, it’s one where you anticipate a problem (and are uneasy about reaching a mutually positive outcome).

And it’s made difficult by the fact that the conversation matters to you, emotions run high and, if you are anything like most leaders, you have replayed this conversation again (and again!) in your head.

It’s the anticipation that causes hesitation, doubt and anxiety. Just framing the conversation as ‘difficult’ leads to an abundance of ‘what if’ thinking. What’s so pernicious about this thinking is that it causes the very outcome you were hoping to side-step! Because such thinking causes five different leader behaviors:

  1. Avoidance
  2. Minimizing the problem
  3. Blame
  4. Triggered behavior
  5. ‘Winging’ it

The big idea: Balancing compassion with confidence

What can go wrong indeed? Quite a lot really! Taking a difficult conversation seriously really does matter as the consequences of a poorly handled exchange can be far-reaching. Thankfully, there’s an alternative to a muddled exchange with confused outcomes. Before this, we need to talk about preparation and your mindset. Without mastery of this, no model can be effective. I suggest that the balance you are looking to strike is that of Compassion + Confidence.

Let’s start with compassion

Two factors are important about compassion. The first is empathy, compassion for someone else. The second factor is your ability to manage the tension between caring deeply about the people you lead, whilst understanding that at times you will be unpopular, so compassion for yourself.


Robust scientific findings across decades of social science research suggest we go through life wishing everyone was more like us. If you were more like me, thought like me, talked like me, there’d be no more difficult conversations. The primary determinant of chemistry in a professional relationship is similarity or attractiveness, or, put another way, we are drawn to people who are like us in ways that are important to us.

Why does this matter in a difficult conversation? It means you are more likely to be negatively triggered in a difficult conversation, because the person doesn’t react the way you do to a stressful situation. Perhaps they reflect whilst you talk; or they cry whilst you sit there in stony silence. Or they fold their arms, utter the deadly word ‘fine’, as you urgently try to find a way forward.

The Confidence Continuum

Confidence lies on a continuum, humility at one end and arrogance at the other extreme. This means you are neither apologizing for holding this conversation, nor do you think you are right above all else. And so, confidence in this context is a belief in your ability to handle this conversation in an acceptable way, without undermining the other person.

It’s also useful to know that like many leadership skills, confidence is not an innate, fixed characteristic. It can be acquired and improved over time – just like the skill of mastering a difficult conversation. For this reason, I often suggest to clients in coaching that they adopt some of the following confident beliefs before a difficult conversation:

  • This conversation needs to be had
  • I have prepared as much as I can
  • I understand myself well enough to remain calm
  • I feel compassion and know how to make it safe to talk.

Time to reflect: what might derail you?

For the balance of Compassion and Confidence to remain steady, it’s important to know what might derail you. And by this, I mean what emotions or behaviors might set you off course?

Practical inspiration #1

Six mindset questions

By now, it’ll be clear that your mindset to this difficult conversation matters! Indeed, it’s the only way to maintain the delicate balance of Compassion and Confidence. Let me help here with preparation questions designed to understand your intent and move your mindset to one of growth and openness. By answering these questions, you’re introducing some ‘grey’ thinking into what otherwise might be too rigid.

So, here are six questions to get your mindset in a useful place before you hold your difficult conversation:

  1. What is difficult about this conversation for you?
  2. What’s the problem for them?
  3. How are you feeling?
  4. How might you have contributed to this problem
  5. What outcome do you want for you, for them, for the relationship?
  6. How do you need to behave to realize your relationship outcome?

Try this out

Think about a difficult conversation you need to have and work through the six questions. I urge you to write down your answers, as the act of writing, as opposed to just thinking, will give you clarity. In answering the questions, what insight to your mindset did you gain? What did you notice needs to shift in your behaviour for a more successful outcome? What is your contribution to the problem?

Practical inspiration #2

After you have got your mindset in a good state, it’s time to plan this conversation. POEMS is a five-step model for you to use as a planning tool for difficult conversations. It’s not a script as no difficult conversation will go exactly the way you plan them, but I’ve given you examples to help you make sense of each step. It’s designed to help you slow down with structure.


  • Prepare yourself.
  • Be calm.
  • Have the factual evidence with you – whether seen, heard or written.
  • Book a safe space – virtually or face to face.
  • Ensure you have scheduled enough time for the meeting – if you haven’t enough time, postpone it until you have.


  • Frame a strong, assertive reason for the meeting by creating a ‘mutual purpose’ statement.
  • Start with facts. This is critical. Facts cannot be argued.
  • Tell your story. The facts alone are not enough. It’s the facts plus your conclusion that make this a two-way discussion.


  • Explore the other person’s point of view – allow them to talk about their interpretation, their ‘story’ situation from their point of view.
  • You can listen without necessarily agreeing.
  • Avoid closed and ‘why?’ questions. These will only cause defensiveness. Instead ask ‘what’ and ‘how’ questions.
  • Your goal here is to get the best possible outcome for you, for the other person and for the relationship. To do this you need as much information as possible.

Make it safe to talk

  • In any difficult conversation, there will undoubtedly be Roadbumps or Flashes, which indicate the conversation has just become ‘unsafe’. And it can happen very quickly. Flashes are speedy reactions, verbal or non-verbal, and can include a sigh, a turning away, a shrug, watery eyes or closing of the eyes. They might be expressions. Breathe, remain calm.
  • Roadbumps tend to be new information, a more serious behavioural reaction, or strong emotion. You need to slow down, listen and take it carefully to get the conversation back on track.
  • Roadbump or Flash, you have to make it safe for someone to talk openly to you – rather than act in a defensive or hostile way. We feel safe when we believe that someone has our best interests at heart; we respect that person’s opinion and trust their motives and ability.
  • To handle critical flashes, you need a blend of confidence, humility and skill. Here are the five best techniques to help you:
    1. Contrasting. Contrasting is a ‘don’t/do’ statement which addresses any misunderstanding and provides context and proportion.
    2. Stay curious. However provocative the response is, just ask yourself, ‘I wonder why they are reacting in this way’, which gives you a moment to think.
    3. Step in and step out. Step into the conversation whilst you are talking but remember to also step out and LISTEN. Remain calm. You can listen without agreeing.
    4. Say what you see in the room. And then move back to Explore:
    5. Say sorry. At times, a simple apology is all that is needed to get a conversation back on track. But make sure this is not a shift back to humility in the face of aggression, so use your apology sincerely and at the right time.

Summarize (with a solutions focus)

  • Summarize first. When you summarize, you show you have listened, reflected and heard their point of view:
  • After all this good work, the best next step is for mutual agreement for the way forwards:
    1. How would you like to resolve this?
    2. What would you like to see happening next?
    3. What do you suggest as the next step?
    4. What do you want to do going forwards?
    5. What support would you like from me?
  • Work out a win/win change: negotiate the next steps to be taken. What are the actions on which you can both agree? Look for the choices that will correct the problem, both now and in the future, focusing on the win/win approach.
  • Unfortunately, not all difficult conversations end with a mutually positive agreement. So, if this is not going to happen, state what behavior you expect to see in the future instead. You have two options here:
    1. Decide not to escalate, but state specifically what you expect to happen in future (plus the consequence of this not happening) and get agreement.
    2. Decide to escalate, explain why and what will be happening next.
  • Always summarize your conversation in writing.

You may already be asking yourself, do I really need to do this for one 15-minute conversation? Whilst this may take time (it will get easier with practice), I guarantee there’s a huge payoff. You’ll go into the conversation feeling prepared, acting with compassion, maintaining perspective and confidence to achieve a good outcome.

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