How to have a difficult conversation

Difficult conversations: black and white chess pieces facing off

Many of the skills needed to manage difficult conversations and behaviour are often referred to, in a rather derogatory tone, as ‘soft’. But there’s nothing soft about dealing with an emotional or confrontational employee who may appear to be trying to unsettle or undermine you. – ACAS

There’s certainly nothing soft about Beyoncé’s latest single, ‘Formation’, and her Black Panther-inspired performance at the recent Super Bowl. As discussed on The Pool, ‘her video for Formation is fiercely political and hugely powerful. It is a call to arms. And it was listened to.’

The racial tensions in the United States; the #BlackLivesMatter movement; black women’s autonomy – these are all difficult conversations to have and to join. But by being assertive (not aggressive) and saying just what needs to be said, Beyoncé joined these difficult conversations and made a constructive contribution to each.

While we’re not all superstars addressing massive sociopolitical issues, the techniques necessary to have difficult conversations – and make sure they’re productive – are the same whether you’re talking to the nation, to your employee, your colleague or your friend.

Just be sure to follow these seven essential steps.

1. Change how you frame the conversation

‘Setting an emotional intention will help to shape your tone of voice when you deliver the message,’ argues Fast Company.

Don’t approach the conversation thinking that it’s going to be difficult. If you go in with negative emotions, it’s more likely the response will be negative too (not to mention you’ll feel stressed and anxious).

Instead think about what you want to communicate and what you want the outcome to be. If there is no good reason to have the conversation – improving performance, letting someone go who’s not a good fit, addressing harassment – then don’t have it: all you want to do is rant, and nothing good will come of that.

Be sure to frame the conversation for the other person as well: make space for the conversation and get permission from the other person to address the issues and, whatever you do, don’t spring it on them out of nowhere.

2. Preparation

Opinions are divided when it comes to preparation. Preparation is necessary to figure out:

  • What you think the problem is
  • What the other person may think the problem is
  • What you want to achieve

You also want to run through what you want to say and decide what is driven by emotions and what is driven by logic, and cut out the former.

From a psychoanalytical perspective, HR consultant Deryn McIntosh, suggests delving into Transactional Analysis, which argues that in any interaction we will fall into one of three identities: parent, child or adult.

Within each of those identities there are several subsets of that identity, and being able to understand and recognise those types in yourself and others may help you drive the conversation towards a purely logical, adult-to-adult conversation.

Whatever you do though, don’t script the conversation: the other person won’t know their lines and it’ll lead to frustration and a stilted conversation.

3. Have the conversation

Don’t avoid it: the situation won’t fix itself and it’s more respectful to the other person to address the situation head on. Two thirds of workers surveyed by the CMI said they feel stressed or anxious if a difficult conversation is coming up, so don’t keep them hanging.

Also: don’t do it over email.

‘The employee loses respect for the leader,’ says Marcia Reynolds, author of The Discomfort Zone: How Leaders Turn Difficult Conversations into Breakthroughs. ‘[Sending out an email] is an act of cowardice and makes the leader look weak in the eyes of their employees.’

4. Turn the conversation over

‘Be curious, not furious.’ – American Management association

This means active and empathetic listening and effective questioning to make sure you understand the other person’s perspective.

Fred Kofman, Professor of Leadership at Universidad Francisco Marroquin, offers a wonderful demonstration of this on the website, which shows how allowing someone to show you a perspective you hadn’t seen, makes them more willing to consider what you see.

In other words, taking the time to see someone else’s perspective increases the chances that both sides will come to a better understanding.

‘In the fog of a hard talk, we tend to forget that we don’t have access to anyone’s intentions but our own. Remember that you and your counterpart are both dealing with this ambiguity.’ – Harvard Business Review

5. Maintain balance

‘You are not the only one that’s right.’ – Rosalie Puiman

The CMI’s research also revealed that 43 percent of senior managers admit to losing their temper and shouting when placed in a difficult conversation, while 40 percent have admitted to panicking and telling a lie.

It is vital to maintain balance when expressing your own feelings and thoughts. Kofman suggests using ‘I’ statements not ‘you’ because ‘there is safety in I’: it’s not confrontational. Consider:

  • You don’t know what you’re talking about


  • I don’t understand what you are saying

Language makes a huge difference in difficult conversations: remember to avoid emotive terms and blame, and stick to logic, facts and constructive suggestions.

6. Negotiate and commit

‘The key in any tough talk is to always keep sight of the goal.’ – HBR

The entire reason you are having a difficult conversation is to resolve or tackle a situation. If you come out of the conversation and no action has been agreed, it has been a waste of time.

So negotiate a plan that addresses everyone’s concerns and commit to specifics: I will research x, you will look into figures from y and we’ll meet again in a week to discuss it.

7. Maintain perspective

Finally, everything will be much easier if you put the problem into perspective and realise that both you and the person you are talking to are only human.

Even people tackling the really difficult conversations, like Beyoncé, need to maintain a little perspective, as Emma Watson and bell hooks discussed in a recent article for Paper magazine. hooks explained when talking about feminism that:

Humor is essential to working with difficult subjects: race, gender, class, sexuality. If you can’t laugh at yourself and be with others in laughter, you really cannot create meaningful social change.

The same is true at work. Difficult conversations need training, courage and maturity, but they also need a little humanity.

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