Most leaders know they should have difficult conversations – about performance, behaviour, or broken commitments – but many lie awake at 2am rehearsing what to say or avoiding it altogether.
In my research with high performers, one difference stood out: they don’t enjoy difficult conversations, but they’ve learned how to approach them in a way that protects trust while still being clear. They see the conversation as part of an ongoing process, not a one‑off “big talk”.
In this article, you’ll learn six practical steps to handle difficult conversations at work so people feel respected, clear – and more likely to change.
Let's take a look at the six things that high performers have learned to focus on when it comes to tackling tough conversations.
Before you start: if there’s no trust, no script will save you
If you rarely invest in the relationship, only speak to people when something is wrong, or they don’t feel safe with you, even the best difficult‑conversation script will fail. Start with regular 1:1s, genuine curiosity, and small signals of care so that when you do need to do a performance conversation, they know you’re on their side.
This is where emotional intelligence matters – noticing your own fear, regulating it, and choosing a response that serves the relationship, not your anxiety.
What stops us from having a difficult conversation are thinking traps such as a fear of hurting the other person, coming across as critical or excessive worry about the outcome.
Yet, our fears about having a difficult conversation can pave the way for a terrible result.
A Zenger Folkman global study found that of people who’d received negative or redirecting feedback, 74% indicated that they were not surprised and had already known about the problem that was raised.
Most of the time, struggling employees know they can improve, but aren't sure by how much or how. They want constructive criticism that helps them develop in their role and be an asset to their team. And that's where great leaders come in and guide.
Prepare your mindset by knowing that you are there to help people perform the best they can. And that's what your people want and expect from you.
Our intentions drive our words and actions. Whether we are aware of them or not, people can really feel the real intention behind our words.
If your intention is to belittle the other person, make them feel wrong or stupid, then this is not the time to have a difficult conversation. It is also a complete waste of time because the other person will feel that you are not their side and will distrust anything you say. If anything, the conversation will work against productivity.
Work on your intention to really feel into how you can help support your report grow and be the best they can be.
Before the discussion, define the purpose and your desired outcome of the conversation.
A good idea is to prepare some talking points. Ideally, they are in dot point format, so that you can easily refer to them. Provide specific examples or evidence to support your statements.
When you plan the conversation also consider the other person's perspective. Put yourself in their shoes to gain empathy and understanding.
It's also a good idea to anticipate potential roadblocks or objections that may arise during the conversation and think about how you can address them.
Before the conversation, if you are nervous or worried, take some time to feel calm and composed. That way you will avoid coming across as defensive or aggressive. It also means you come to the conversation in true service of the other person. Otherwise, your fears are making the conversation all about you.
Practice deep breathing or other relaxation techniques if you feel yourself becoming overwhelmed.
During the conversation, if you feel yourself panicking, take a pause if needed to collect your thoughts and respond thoughtfully.
Effective communication is essential during difficult conversations to ensure that both parties feel heard, understood, and respected. Here are some strategies to enhance communication during conflict:
- Active listening: Give the other person your full attention, maintain eye contact, and listen without interrupting. Show empathy and understanding by summarising their points or asking clarifying questions.
- Use 'I' statements: Express your thoughts and feelings using 'I' statements to avoid sounding accusatory or judgmental. For example, say 'I feel' instead of 'You always' or 'You never'.
- Seek common ground: Look for shared interests or goals to establish common ground and build a foundation for finding solutions together.
- Be solution-oriented: Focus on problem-solving rather than dwelling on the past or assigning blame. Explore alternative options and propose compromises that can lead to a win-win outcome.
- Use non-verbal cues: Pay attention to your body language and non-verbal cues, such as maintaining an open posture, nodding to show understanding, and using appropriate facial expressions.
- Co-create a plan: Summarise the key points discussed to ensure understanding and clarify any misunderstandings or misinterpretations. Get their agreement and make sure there are clear action steps for them to take.
We often put all our energy into the lead up of the big conversation, not realising that the important work is in the follow-up. Where a lot of leaders trip up is they don't put the necessary structure around ensuring their report is improving their performance.
Here are some steps to consider:
- Follow up with actionable steps: Identify the necessary actions or next steps required to resolve any issues or address concerns that arose during the conversation. Keep everyone informed of the progress with regular updates.
- Schedule regular check in points according to what you agreed on during the discussion. This is where you need to start observing a turnaround. Provide more support and be specific about what you need to see and when you know you have the outcome you wanted.
- Reflect on the conversation: View difficult conversations as opportunities for personal and professional growth. Reflect on what you have learned from the experience and apply those learnings to future interactions. What would you do differently next time?
To effectively manage difficult conversations, it is crucial to approach them with empathy, open-mindedness, and a focus on finding a resolution rather than assigning blame. These conversations provide an opportunity for growth, understanding, and strengthening relationships within the workplace.
If your intention is to help people learn and improve, they will feel that. Growing is often uncomfortable and painful. If they decide, to be hurt and ruminate about the feedback, and blame you, that is their issue to work on. You are not responsible for how people take on feedback and react to it. All you can do is provide corrective feedback that is said with kindness and clarity.
And always keep in mind, dedicate most of your time to planning the conversation and diligently following up to guarantee tangible results. By investing effort and time into these steps, not only does the conversation become smoother, but it also becomes progressively easier with each interaction.
If you’re realising that scripts alone aren’t enough – that you also need the inner work of emotional regulation, self‑trust and relationship building – that’s the heart of my 12‑month Leadership Mastermind.
I’m running a free webinar on [title/date] where we’ll dive deeper into how to build the trust and emotional intelligence that make difficult conversations easier.
You can [register here] and learn more about the [Leadership Mastermind] if you’d like to embed these skills across your leadership team.