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Facing a difficult conversation at work?

Are you facing a difficult conversation at work

Are you facing a difficult conversation at work?

As a leader, you need the ability to handle difficult conversations at work. For example, you might have to:

  • Address an underperforming team member
  • Speak up when there’s a problem
  • Pitch to a prospective client
  • Negotiate new terms with a supplier
  • Request a pay-rise or promotion

These types of conversations can take courage and confidence. This article gives you some ideas about the best mindset to adopt, which words to use and avoid, and the body language that will help you.

What are courageous conversations?

We all know that communication is key to success, and that conversations are a key part of effective relationships. But some conversations are easier than others.

You might have to hold difficult conversations with employees. Or you might be on the other side of a performance review where you have to accept feedback, perhaps even criticism. And you probably need to keep good relationships with third parties outside the organisation, such as clients and suppliers – yes, even the ‘tricky’ ones.

Having worked with many leaders over the years on how to navigate challenging conversations, and walked knowingly into conflict a number of times myself as part of my leadership career, I know that any conversation you perceive as being ‘difficult’ can be overcome with courage, preparation and skill.

Benefits of courageous conversations

It’s not an overstatement that a single constructive conversation at work can change the path of a working relationship, a career, or the whole company.

Initiate these conversations – even difficult ones – and you’ll get more respect for your openness and honesty. It will make you a better boss and a better colleague. And it’s the only way to achieve change.

Something niggling you? Don’t let it fester. Taking action and talking about it (to the person who can do something about it) is the only way to move forward.

What’s the impact of NOT having difficult conversations at work?

For their book Crucial Conversations, authors Joseph Grenny and David Maxfield studied 1,025 workers and found:

  • 72% said they or others failed to speak up when a peer did not pull their weight
  • 68% reported failing to address disrespect
  • 57% let it slide when colleagues skirted important processes at work
  • 40% reckoned they waste two weeks or more ruminating about the problem
  • They estimated an average cost of $7,500 per organisation in lost time and resources.


Wanting to avoid conflict is normal, but, if you don’t step up, be brave, and have those difficult conversations, the relationship will continue to deteriorate. The longer you wait, the more stuck you will become. Your resentment will build and that won’t do your health any good in the long-term.

Left alone, low-level disagreements disrupt your credibility as a leader. They can turn into major conflicts, negatively impact project timelines and budgets, reduce employee morale and engagement, and affect the overall corporate culture.

Practical tips: Choose your communication channel

To handle a difficult conversation, email or texting just won’t do. So don’t be tempted to avoid confrontation by putting your side of the story in writing, even if peppered liberally with emojis! It’s too easy for the written word to be misunderstood.

For your message to land effectively, you need to pick up the phone and talk, have a video call, or even arrange a face-to-face discussion over a cup of coffee or lunch. That way, you have more chance of achieving the results you want.

Why? Because talking makes it a two-way interaction, not a one-way broadcast.

Eye contact and tone of voice help, both you and the other person. The ability for each of you to ask questions, to recap what you heard, and to clarify understanding will all contribute to a productive outcome.

Practical tips: Mindset for effective difficult conversations

Don’t speak up while you’re angry, irritated or upset. Wait until you’ve calmed down. Perhaps practice the conversation with a trusted friend or coach before you do it ‘for real’.

During the conversation, it’s OK to acknowledge your own fallibility and vulnerability. But remember it’s not all about you. The other person will bring their own feelings and perspective to the conversation, so you need to be ready for any reaction.

It’s about dialogue. Invite the other person to share their point of view. Encourage them to disagree. Ask questions if there’s anything you’re unsure of. Really listen to what they say. Reflect it back so they know they’ve been heard.

Be ready to be flexible. You never know, they might even change your mind, or at the very least, give you a different perspective.

Practical tips: Words to use/avoid during difficult conversations

You might start the conversation by admitting that you find it difficult and feel uncomfortable but are doing your best because it’s important to bring the specific issue into the open.

Explain what you think and feel. Tell them the problem, the impact, and the outcome you want. Take the emotion out of it.

Be warm and authentic, direct and clear. Be concise. Say what you mean. Don’t waffle or fudge the issue.

Talk about their unwanted and expected behaviour, and its effect. Remember, it’s not about them, it’s about what they’re doing or not doing, and so don’t talk about them personally, or their personality. (Footballers call it “playing the ball, not the player”.)

Remember, you’re a human being talking to another human being. So treat the other person with respect and compassion. In Transactional Analysis (TA) this would be called communicating in Adult to Adult as opposed to Parent to Child (or Child to Parent/Adult). TA is a powerful school of thought that analyses every conversation as a ‘transaction’ and shows the three modes that we can all operate in, as shown in the diagram below.

Even when you’re in charge, you don’t have to go into in ‘parent’ mode as there’s a risk the other person will then go into ‘child’ mode. People won’t be defensive when they feel safe, so create a space of psychological safety, where it’s OK for people to be truthful about what they think and feel.

Come from a place of curiosity, with a positive attitude and the desire to help or learn. Look at what you have in common as well as your differences. Consider how you may have contributed to the problem. Remain focused on your desired outcome.

You’re aiming for a Win:Win situation on the grid below, where you both come out of the conversation with dignity:

  I win I lose
You win Win:Win Lose:Win
You lose Win:Lose Lose:Lose

And if you find yourself losing control, try the Power Pause, a technique I’ve developed to help you manage your emotions and stay calm under pressure.

Practical tips: Body language during difficult conversations

Before future tough talks, take a deep breath and gather your courage.

Don’t sit back with folded arms; equally, don’t lean too far forward as that might be perceived as aggressive. When you’re physically in balance, you’re more likely to feel emotionally balanced as well.

Keep breathing slowly, calmly and deeply throughout, so you stay centred and in the moment.

Be ready for some powerful emotions to come up. Try the Power Pause, a technique I’ve developed to help you manage your emotions and stay calm under pressure.

And bear in mind that you might need to practice some self-care after the conversation is over. It’s OK to take a break, get some air or a drink of water. Be kind to yourself, whatever the outcome, reflect on what worked (and what didn’t) and what you would do differently the next time.

If it doesn’t go well at first, don’t give up. Tell them you need time to reflect, prepare once more, and give it another go.

Recognise that the first phase might be about reaching mutual understanding rather than arriving at a particular solution.

What next?

Are there some conversations that you dread? What conversations are you avoiding right now? Ask yourself why.

Tough conversations don’t need to be tough.

Developing these skills for use in the work environment will also benefit you in your personal life. For personalised help with this, we run masterclasses for organisations on Courageous Conversations – for more information please get in touch.

For further reading, you might find these books useful (coincidentally, the authors share the same surname):


Antoinette Dale Henderson

The Gravitas Coach

Antoinette is an executive coach, keynote speaker and two-time author with over 25 years’ experience in leadership communications, including 16 years holding senior positions in some of the world’s top PR agencies.

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To discuss how Antoinette and her team can accelerate your success, book a call now!

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