Mastering Difficult Conversations: A Comprehensive Guide for Leaders

Have you ever been in a situation where a difficult conversation was needed? Me too! Did you like it? Me neither! However, conflicts and the need for difficult conversations are fundamental aspects of leadership - and life in general. Over two decades in management, I've navigated numerous tough conversations, from issuing formal warnings to terminating relationships. Each situation significantly impacted those involved, teaching me to align these discussions with my personal values and maintain my integrity. In this article I have gathered some perspectives and advice.
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Leading effectively requires the ability to navigate difficult conversations – whether they involve delivering bad news, addressing performance issues, or managing conflicts. These conversations are pivotal as they test a leader’s competence and emotional intelligence. However, when approached with the right mindset and strategies, difficult conversations can become powerful tools for fostering trust, encouraging professional growth, and strengthening team dynamics.

A difficult conversation is usually about providing feedback related to an undesired situation or behaviour. Therefore as a starting point, be clear about what your motives are and which ambitions you have for future situations and behaviour. Remember, feedback often says more about the giver than the recipient, so be clear about what your motives are for having this difficult conversation.

Preparation: Laying the Groundwork for Success

Preparation is vital but should not be confused with the attempt of scripting every part of the dialogue. Human interactions are dynamic, and over-preparation can lead to rigid conversations that fail to address spontaneous concerns or reactions. Instead, you should focus on outlining key points and objectives, understanding the broader context, and anticipating possible responses. 

A vital part of preparation is getting the appropriate data. When gathering facts about the issues at hand it is important to do it with as much neutrality and objectivity as possible. It’s crucial to approach the gathering of facts without bias, almost like a CCTV camera that simply observes without interpretation. This ensures that you have a clear and undistorted understanding of the situation, allowing for a flexible and informed approach during the conversation. An important perspective about the feedback is to keep it brief and to the point. Do not fall into the trap of providing a long list of sins that the counterpart has committed. A good rule of thumb is to limit it to what you can write on a Post-It, otherwise it most likely becomes too overwhelming and the desired change unlikely to happen.

Planning should thus focus on outlining key points and objectives, understanding the broader context, and anticipating possible responses, while also being prepared to adapt based on the dynamic nature of human interactions. As you cannot control the flow of the conversation you must be able to improvise. With sufficient preparations you lay the groundwork for improvising during the conversation, and the next step is presenting your observations during the conversation.

Presenting Observations Neutrally and Clearly

Once in the conversation, it is of highest importance how you present the data. It is essential to do this in a neutral way being specific about time, situation and behaviour. Do not fall into the trap of generalising because this first of all is influenced by your personal bias, with the result that the recipient most likely will question the legitimacy of your comments and start defending or stating that you are simply wrong. 

I particularly like the SBI model for providing feedback because it is simple and neutral. Here is how it works:

  • Situation is where you begin. Share with the recipient the situation where you observed the behaviour occur. Be concrete about time and place. This helps make the feedback specific and helps the recipient to better understand it.
  • Behaviour is next. Describe the specific behaviour you are giving feedback about. Tell the recipient what you observed, not your interpretation of it. It is critical to leave your judgement out of the feedback. As a rule of thumb only share what you can see, hear or touch. That helps you stay away from interpretations and judgements.
  • Impact is where you explain the consequences of the observed behaviour. This can range from what you thought and felt and why, to broader impact on others or the whole team.
  • Intent is an optional thing you can add, but it is a great idea to ask about the intention behind the behaviour. There might be a sound reason that is unknown to you – or at least different from your assumptions. This can greatly help explain the gap between the intent and the actual impact.

Here is an example of how you can use it: 

“Peter, yesterday at the weekly team meeting, I saw you enter the room 10 minutes after it was scheduled to start. It also happened the week before. Your absence hindered the rest of the team in really getting the meeting started. I also saw that Paul needed to fill you in, taking the focus from the current topic, once you were there. I have observed that a few other of your colleagues have started coming a few minutes after the scheduled start as well. This has the consequence of the first 15 minutes of the meeting not really being useful. We should spend our time in a more valuable way. Is there something hindering you in being there at the scheduled time?”

As you can see in this example, the feedback giver is avoiding judging the situation by not using the word ‘late” about what observation. It is also demonstrating curiosity as the reason for Peter coming after the scheduled start could be a matter of the schedule of public transportation rather than laziness. It opens up a conversation about the matter and at the same time states that things must change. Either by Peter being on time or the meeting being rescheduled to a more feasible time.

Once you have provided the feedback, encourage reflection. Remember feedback is only useful when it is considered and acted upon. Encourage the recipient to reflect on what you shared and how to possibly act differently in the future. If you asked about the intent, it can be a good starting point for discussing what to change.

You can use the SBI-tool to provide clear feedback in a non-judging way. There are other ways of providing feedback, like the Sandwich model, Here the intended feedback is merged in between a positive start and a positive ending. It is probably a matter of taste, but I find this model dishonest and a sign of weakness. Of course feedback should be given with the intention of a positive change, but why suckercoating it? Are you scared about the consequences of providing the feedback? My own experience with people providing me feedback using the Sandwich model is that I meet it with scepticism. Once a feedback giver starts with a positive statement, I instantly start thinking: “Yes, but what are you really trying to tell me?” To be honest, I lose a bit of my respect for the feedback giver when this happens. While positive feedback is encouraging, constructive and honest feedback is crucial for personal and professional development

Acknowledging and Valuing Perspectives

It is important to remember that human beings in general are acting with their best intentions. They are usually also acting according to their personal values, otherwise they will be in distress. Therefore, recognising and validating the viewpoints of others is important. This is not just about being polite – it is rather a strategic approach that facilitates more effective communication. 

By understanding and acknowledging the perspectives of others, you can address the underlying concerns that may be fuelling the conflict or resistance. A great question to ask yourself is: “If it makes sense for the person to think/talk/act like this, how can that be? What is the good intention behind this behaviour?” This approach not only enhances the dialogue but also strengthens the relationship by showing respect and consideration for the individual’s feelings and viewpoints.

Staying in Control: Harnessing Emotional Intelligence and Breath

As previously stated, you cannot control the flow of the conversation, but you can control yourself! Maintaining composure and control over your emotions is crucial for you when engaged in difficult conversations. This control stems from a well-developed emotional intelligence, which involves understanding and managing your emotional responses. It is okay to have feelings about the matter, but during the conversation it is essential to dose these feelings in the right amount. Have an awareness of what is triggering your emotions. I for example have a deep awareness of the feeling of fear which prevents me from being overwhelmed by fear and avoids me from having counter productive responses caused by fear.

Techniques such as focused breathing are instrumental in achieving this control. Deep, deliberate breathing helps mitigate stress responses, enabling you to remain calm and think clearly during tense discussions. By practising mindful breathing regularly, you can ensure to be centred and composed, ready to tackle the challenges of the conversation without becoming overwhelmed.

Staying in control not only addresses issues effectively but also sets a positive example.

Enhanced Listening and Communication Skills

Active listening is essential. You must focus fully on the one speaking, showing genuine interest in their words. This involves not just hearing their words but also paying attention to non-verbal cues such as body language and tone, which can provide additional context. For example, are the arms of the person crossed or does it indicate a more open attitude? Are you capable of having eye contact? These signals tell you something about how comfortable the person feels. 

You are providing feedback and that alone creates an uncomfortable situation, but if too uncomfortable, your message might not fully be received and acted upon. Remember, this context is most likely not powerless (and it probably should not be either), but the approach you are using might hinder you in succeeding. I have had conversations with employees where I realised that the person was uncomfortable sitting in front of me. He avoided having eye contact at all times. In this situation I changed the context from a meeting room to a walk and talk. Having a situation where we naturally did not have to look each other in the eyes helped the conversation towards a feasible solution.

Having an awareness of your inner voice is helpful. Is it supporting your focus on listening and understanding your counterpart or is it simply helping prepare your next reply? When I experience my inner voice taking over the conversation and preventing me from listening, I usually apply the technique of forcing it to repeat what the speaker is saying. I might also vocally mirror back to the speaker what I heard, This also strengthens the speaker’s feeling of being heard and understood. Doing that, I might paraphrase what the speaker said, so it comes out in a more positive tone. This is not to ignore the negative aspects, but rather with the purpose of fostering a positive atmosphere towards the change which must happen.

Slowing down the conversation pace can also help in digesting the information fully and responding more thoughtfully, thereby reducing misunderstandings and promoting clearer communication. Do not fear the pauses in the conversation. Silence is often a sign of reflections or simply information sinking in and being accepted, so strain away from bombarding the counterpart with words!

Strategic Tips for Conducting Difficult Conversations

Here are a few tips which can help you conduct difficult conversations.

  • Empathise: Try to understand the emotional state and needs of your counterpart. Empathy can transform a defensive situation into a collaborative discussion.
  • Be Direct but Compassionate: Convey your messages clearly and directly to avoid ambiguity, but also temper your directness with compassion to avoid coming across as harsh.
  • Offer Constructive Feedback: Frame your criticisms in a way that emphasises improvement and development, rather than personal disappointment or frustration.
  • Seek Mutual Benefit: Aim for solutions that address the needs of both parties. This not only resolves the immediate issue but also promotes a cooperative relationship moving forward.
  • Reflect and Learn: After each difficult conversation, take time to reflect on what went well and what could be improved. This continuous learning approach can significantly enhance your communication skills over time.

Cultivating an Inclusive and Open Culture

Finally, the culture within an organisation can significantly influence how difficult conversations unfold. Leaders who consistently demonstrate openness, inclusiveness, and appreciation create an environment where honest dialogue is valued. 

An important part is your own role modelling of actively seeking and using feedback from your subordinates. This requires some gut from your side in order to feel comfortable in showing vulnerability. Scary, isn’t it? However, it helps you in forming a culture which is not only making difficult conversations less daunting but also helps in resolving issues proactively. Regular feedback, both positive and constructive, should be normalised to foster an atmosphere where continuous improvement is embraced by all.


Leaders who master the art of conducting difficult conversations can significantly enhance their leadership effectiveness and contribute to a more positive organisational culture. By integrating emotional intelligence, strategic preparation, and empathetic communication, leaders can transform challenging interactions into opportunities for growth and development. The goal is not merely to get through these conversations but to emerge from them having made positive impacts on relationships and organisational outcomes.


Photo credit: Vitaly Gariev onm

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Mastering Difficult Conversations: A Comprehensive Guide for Leaders

Have you ever been in a situation where a difficult conversation was needed? Me too! Did you like it? Me neither! However, conflicts and the need for difficult conversations are fundamental aspects of leadership - and life in general. Over two decades in management, I've navigated numerous tough conversations, from issuing formal warnings to terminating relationships. Each situation significantly impacted those involved, teaching me to align these discussions with my personal values and maintain my integrity. In this article I have gathered some perspectives and advice.

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