A four-step process for having tough conversations with difficult people

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James Scouller looks at how to structure those challenging conversations so that everyone wins

So instead they avoid them altogether. Or they engage in “join the dots” conversations where they give half the story and expect the other person to figure out the rest, which they rarely do. By avoiding tough conversations or tiptoeing around them, they let the organisation down. So how can leaders help themselves and others to engage in tough conversations that work?

If you’re thinking of arranging training programs on this subject I suggest organising the content under three headings:

1) Knowing when to be assertive

2) Knowing how to be assertive

3) The key dos and don’ts

Knowing when to be assertive

There are times to assert and not assert your position. Knowing the difference is crucial. The two points to consider are intent and wisdom. These questions can help you:

Intent: What is my aim? Do I want a verbal or emotional reaction from the other person; if so what? Do I want a behavioural change; if so what? Or do I simply want the satisfaction of venting my feelings? Be specific. And be wary of the third aim.

Wisdom: Will I lose something I value in following this intent? Or might I gain something I don’t want? Either way, do the benefits from asserting myself exceed the unwanted consequences?

Knowing how to be assertive

This technique uses a four-part framework.

One: describe the other person’s behaviour

  • You describe, without judgement, the specific behaviour in question. That means describing it factually without applying negative labels. This avoids giving the other person a chance to dispute what you’re saying while holding your connection with them. This could focus on what they’ve done or failed to do. The key is to talk specifically, clearly, simply and accurately. What you’re saying must be indisputable. So stick to the behavioural facts – don’t label the person (e.g. “you’re a bully”) or try psychoanalysing their motives. Get this step wrong and the rest of the framework won’t work.

Two: summarise your feelings about the other person’s behaviour

  • If you’ve navigated the first part successfully, the second part becomes all-important. Here you say what you feel about the person’s behaviour. This builds on step one to give this framework its power. Without this injection of emotion, your feelings, you’ll weaken your intervention, meaning it may fail. Why is it so important to inject emotion? It’s because emotion acts as the bridging force between ideas and actions. It brings intensity and direction to your description of the person’s behaviour by adding your feelings. This makes it penetrate the other person’s psychological shell. It’s like the extra power needed to send a rocket into orbit. Without it, the rocket won’t blast beyond the atmosphere.

Three: explain the wider impact of their behaviour

  • Now you explain the wider (perhaps less obvious) impact and consequences of their behaviour on you and/or other people. This might cover how you see them, your future relationship with them, the impact on your team’s reputation, how it negatively affects customers, or how it makes life harder for teammates and so on. By providing the big intellectual answer to the “so what?” concerning your feelings, it builds on the emotional power of step two.

Four: explain what you want instead

  • Here you request a specific change in the person’s behaviour. It must be clear so they can’t misunderstand what you want them to change – and by when. Don’t leave them wondering. Occasionally, but not always, it’s important to say what will happen if they don’t deliver the change you want, especially if you may have to dismiss them if they don’t shift their approach.

You can vary how you apply this four-step tool. You can insist your colleague shifts their attitude or behaviour (or both) and make the implications (the “or else”) ultra-clear if they don’t change.

But you can use it in a softer, kinder way by varying your voice tone and body language. So don’t see assertiveness as “going into battle”. This tool is more flexible than it first appears and you can use it in different ways.

Do’s and don’ts of challenging conversations

  • Ideally, do it in private (although sometimes that isn’t possible).

  • It’s usually best to start step one in an empathetic way. If you can, say you understand the other person’s feelings. This gives you the best chance of showing you’re not trying to pick a fight and may help settle their emotions at the start.

  • Make sure what you’ve described in step one is factually correct. It must be watertight. No wriggle room allowed. Get that wrong and you’ll find the process unravels.

  • In step one, don’t use labelling or judgemental words (like “useless”, “lazy”, “bully”) that say what a person is in your opinion. Instead focus on what has been done or not. Nor should you label the behaviour (e.g. “incompetent”, “bumbling”). Lastly, don’t generalise (“you always…”). Stick to the facts. Simply describe what they’ve done or failed to do in a specific situation or situations.

  • Just as important, in step one don’t try to guess why they’ve done what you’re objecting to. Don’t play psychoanalyst. Don’t try to read their mind.

  • Don’t omit step two, it makes your act of assertiveness pack a punch.

  • Make sure you align your body language with your words. Face the other person. Stand or sit up straight. Keep your voice calm, not abrasive. Don’t use dismissive gestures.

  • Use “I” statements. This is crucial. Everything you say must centre on your feelings. Not someone else’s feelings, nor your team’s feelings. Your feelings. You must own this statement.

  • With more difficult, high-risk or high-impact conversations, rehearse beforehand. If necessary, practise your statement with a trusted friend and hear their thoughts.

Essential conversations

Having tough conversations with difficult people is an essential skill for L&D leaders, as it directly impacts team performance and satisfaction. By understanding when to be assertive and how to effectively employ the four-step framework of describing behaviour, expressing feelings, explaining impact, and outlining desired change, leaders can navigate these challenging conversations with finesse.

While it may be uncomfortable at times, embracing these principles will not only improve relationships and team dynamics but also fulfil one of the fundamental desires employees have from their leaders – the willingness to address and resolve issues head-on, ultimately fostering a more productive and harmonious workplace.


James Scouller is an executive coach and author of the trilogy, How To Build Winning Teams Again And Again

James Scouller

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