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How do I have that ‘Challenging’ Conversation?

Passive aggressive

This article explores 5 key principles to help you manage that challenging conversation effectively to ensure a good outcome for both you and them.

What’s a Challenging Conversation?

A challenging conversation is one where you are anxious about your ability to handle the outcome. So for example where you know that your opinions are significantly different from the person you’re having the conversation with, or where emotions run strong, or where the stakes are high and you may put yourself or the organisation’s reputation at risk. The conversation may be with your manager, your staff, your donors, service users, or other stakeholders.  One thing is for sure – you can’t put it off forever!

So you need to deal with it – the question is how? This article explores 5 key principles to help you manage that challenging conversation effectively to ensure a good outcome for you and them. We also introduce you to the ‘tell a story’ approach to changing your own approach.

Often emotion dictates our response, the adrenaline is pumping, the brain diverts blood away from the reasoning centres and reverts to basic impulses: fight (violence) and flight (silence).

Towards the end of this article you’ll find some examples of where we have worked with customers on Emotional Intelligence and Challenging Conversations. If you’d like to know more contact Yvette Gyles, Director, on 0207 978 1516 or

Mastering Challenging Conversations

The key is to create a successful dialogue. There are two things that get in the way of successful dialogue. Silence makes it hard to accurately assess meaning – worse still it may be misinterpreted as passive aggression. Violence in language or body language can force opinions to become polarised. Neither of these approaches works.  Here’s a checklist of what does:

1) Focus on What You Really Want

Skilled people, with emotional intelligence, begin a challenging conversation by knowing what they really want – what’s the goal?

Is it to get one over on somebody, to salvage your wounded pride, or to achieve a positive outcome? Only the last brings any benefits. The other two are risky and likely to promote a direct negative response in the person you’re having the conversation with.

So before you go into any challenging situation take time to consider what’s the outcome you really want.

Think too about a Plan B – an outcome you can live with. Direct all your energies towards the plan A outcome, and if that proves unachievable work on Plan B.

2) Check Your Motives:

Our motives often change without any conscious thought on our part. The dialogue can be threatened by one (or more) of three natural desires:

  • Wanting to win
  • Seeking revenge
  • Hoping to remain safe

To check which desire is at work stop and ask yourself these questions:

  • What do I really want for myself?
  • What do I really want for others?
  • What do I really want for the relationship?

Now add a fourth question:

  • How would I behave if I really wanted these relationships to work? (And what’s stopping me doing that…often the answer is one of those three desires.)

People with emotional intelligence believe that dialogue is always an option i.e. not a case of who’s right / who’s wrong, but how can we find a solution that will work for us both.

3) Notice When Safety Is at Risk: Practice Acuity.

It’s good to be clear on what you want, but you also need to watch for how other people are feeling and analyse their behaviour. Look out for three things in yourself or others:

  • Learn to spot challenging conversations ‘signs’: be aware of physical signs (tightness in stomach, dry mouth, tension), emotional signs (feeling scared, hurt, or angry), and behavioural signs (raising voice, pointing finger, becoming quiet.)
  • Learn to look for safety problems – do people feel safe? Or fearful? Only with safety will dialogue happen (e.g. ability to receive difficult feedback because of feeling it’s been given with your best interests at heart – i.e. safely). This means watching out for silence (flight) or violence (fight).
  • Look for your preferred style under stress – what do you do as a default? Check if these habitual behaviours are helpful or hindering. Often the best way to get someone else to change is to begin by changing yourself. Try almost anything different to see if you get a different result – where you have the conversation, how you start it, your voice tone…

4) Silence and Violence

Silence or violence are two key elements of a guaranteed unsuccessful conversation. Watch for these:

three elements of silence:

  • Masking – understating or only selectively showing our true opinions – e.g. through sarcasm or humour
  • Avoiding – simply not ‘going there’ and dancing around the subject without admitting a reluctance to talk openly
  • Withdrawing – leaving the conversation or steering towards something safer when things get tough.

three elements of violence:

  • Controlling – coercing others to your way of thinking – e.g. through overstating (“everyone knows…”), speaking in absolutes (“we tried that and it was a disaster”)
  • Labelling – putting a label on people or ideas so we can dismiss them – e.g. “that idea is Neanderthal,” or “that’s exactly what someone from HQ would suggest”
  • Attacking – making the person suffer – belittling / threatening them through your body language or what you say.

5) Master My Stories: How to Stay in Dialogue When You’re Angry, Scared, or Hurt>

When you’re in dialogue make sure you observe these principles:

  • Own your emotions, rather than using “s/he made me feel” language. No one can make you ‘feel’ anything. You have to allow yourself to feel.
  • Act on your emotions, rather than allowing your emotions to act on you. Be aware of them and check out if your ‘gut’ response is best.
  • The most emotionally intelligent aren’t held hostage by their emotions, nor do they try to hide or suppress them. Instead, they act on their emotions.
  • Try to see it from the other person’s perspective.  What does this behaviour look like from the ‘other side’? What would an objective observer say?

Having a challenging conversation with yourself – tell a new story

There is an intermediary step between a situation or stimulus and our emotional response. We can think of this as the story we tell ourselves: we add meaning to the action we have observed. We also add judgement – was it good or bad?

This can happen incredibly quickly, e.g. someone laughs at me and I feel angry and upset. But this doesn’t happen every time someone laughs at me. Sometimes I feel proud and a bit smug. So I have told myself different stories.

The path to action:

The good news is since we are telling the story, we can take back control by telling a different story. And until we tell different stories, we cannot break the repeat loop.

Skills for Mastering our Stories

Retrace your Path. Slow down by working backwards:

  • [Act] Notice your behaviour. Ask: am I in some form of silence or violence? Am I just repeating a loop that is comfortable even if it doesn’t work?
  • [Feel] Get in touch with your feelings: What emotions are encouraging me to act in this way? (How rich is your vocabulary for your emotions? how accurate is it?)
  • [Tell story] Analyse your stories: What story is creating these emotions? Question your assumptions? e.g. “Louis is a bully” is not a fact, it’s a story.
  • [See/hear] Get back to the facts: What evidence do I have to support this story? Focus on factual behaviour e.g. “he was sarcastic” is not fact, it’s subjective.)

Watch out for three ‘clever stories’ we tell ourselves:

  • Victim stories – “it’s not my fault” – the other person is bad/wrong: we exaggerate our own innocence.
  • Villain stories – “it’s all your fault”: we overemphasise the other person’s guilt and attribute bad motives to them
  • Helpless stories – we were powerless to do anything else, and so absolve ourselves of responsibility.

While Villain and Victim Stories look back to explain why we’re in the situation we’re in, Helpless Stories look forward to explain why we can’t do anything to change our situation.


  • All clever stories enable us to abdicate responsibility for our actions so we tend to like them.
  • The can also help us cover up for ‘selling out’ – i.e. you don’t act according to your principles.

Clever stories are inevitably incomplete – they omit crucial information about us, about others, and about our options. To counter clever stories tell a useful story – i.e. one that leads to healthy action and dialogue. So:

  • Turn victims into actors: ask “am I pretending not to notice my role in the problem? What am I doing to create this situation?”
  • Turn villains into humans: ask “why would a reasonable, rational and decent person do what this person is doing?” – replace judgement with empathy.
  • Turn the helpless into the able: ask “what do I really want for me, others and the relationship?” Then ask: “what would I do now if I really wanted these results?”

Our Work

=mc has worked with a number of organisations on challenging conversations:

  • Action Aid:  We worked with a range of fundraising and marketing staff to develop techniques for giving constructive feedback, and also used the Facts/Story/Emotion/Behaviour model to explore new options and approaches in role play situations. This has helped them internally bit also been useful to communicate more directly and openly with supporters.
  • Amnesty: A team had experienced stress due to changes within the team and the challenge of managing a large budget.  Communication styles within the team also varied significantly. So while there was respect and care within sometimes behaviours could become unhelpful.  We created a programme that covered dealing with stress, emotional intelligence and flexibility of communication style helping ease tensions.
  • Shepway District Council:  This small but ambitious local council is going through a radical change programme aiming to deliver services more efficiently and effectively through new “Ways of Working.” We ran a series of workshops to help middle managers create strong change messages, manage their emotional responses and have difficult conversations with staff feeling at risk.

To find out more about how =mc could help you manage difficult conversations, introduce emotional intelligence in your work, of facilitate difficult team situations contact us.

Some elements in this article are based on the book

Crucial Conversations Tools for Talking When Stakes Are High, Second Edition [Paperback] Kerry Patterson (Author), Joseph Grenny (Author), Ron Mcmillan (Author), Al Switzler (Author)


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Charlotte Scott

About Charlie Scott

Charlie specialises in leadership development, team facilitation and strategy development. Charlie worked for over 20 years in the not-for-profit sector. Before joining =mc ten years ago, she created and...