In my last article, I wrote about the stories we tell ourselves about other people’s behaviour and the importance of checking whether those stories are actually true. The obvious question is how. ALSO READ: How far can you go? Turn goals into results in 2026 The challenge is that testing our assumptions usually requires a conversation. Asking a colleague what they are really thinking can feel deeply uncomfortable. Yet the ability to initiate tough discussions is one of the most valuable skills you can learn. It helps you solve problems earlier, build stronger relationships and make decisions based on facts rather than assumptions. ALSO READ: ‘You got this’ is hard to hear and even harder to say This month, I conducted a workshop on tough discussions with HR leaders from leading Rwandan organisations. We explored the conversations people find most difficult, why they avoid them and skills that make them easier to navigate. ALSO READ: The antidote for office politics The conversations people dreaded most were speaking up to senior leaders, dealing with resistance to change, delivering bad news about job losses and giving difficult feedback to talented employees. ALSO READ: Automate admin, not trust Because tough discussions carry personal risk, many of us put them off. Yet participants in my workshop repeatedly described situations where delayed action had made matters worse for both the individual involved and the organisation. Given the fear people feel around tough discussions, we discussed strategies that can make initiating them easier. Step one is preparation. Tough discussions rarely go well when they are triggered in the moment. A little preparation helps you understand the situation more clearly, anticipate the other person’s perspective and consider how to move forward together. Giving people advance notice is also helpful. A simple message like, “Could we spend some time tomorrow discussing something important?” reduces the chance that the other person will feel ambushed. Another useful practice is to start the discussion by identifying shared goals. Before diving into the issue, explain why the discussion is worthwhile. Connecting it to a shared objective, such as serving customers better, reducing mistakes or helping the team succeed, creates a more constructive atmosphere. It also helps to place feedback in context. Many people hear criticism as a sign that they are no longer valued, even when that is not intended. You can reduce this risk by stating what you appreciate about the person before discussing the issue. This reassures them that the purpose of the discussion is improvement, not rejection. From there, it helps to share your facts, feelings and story. Explain what you have observed, how it has affected you and the conclusions you have drawn. This can feel vulnerable because you are inviting the other person to challenge your interpretation. Yet that vulnerability can also change the tone of the discussion. By acknowledging that your perspective may be incomplete, you invite the other person to become a partner in understanding the situation rather than an opponent in an argument. Then comes the step many people find hardest: listening to the other person’s perspective. Once you have shared your facts, feelings and story, ask them to share theirs. Resist the temptation to interrupt. Instead, ask clarifying questions and summarise what you have heard. Once both perspectives are on the table, it’s much easier to identify areas of agreement, acknowledge differences and work towards solutions that address the concerns of both parties. Finally, agree on next steps. The best discussions end with clear actions and a commitment to review progress later. Much of our workshop with HR leaders was devoted to role-playing tough discussions. Practising a structured approach made these conversations feel far less intimidating than many had expected. Conducting tough discussions well is a genuine superpower. It surfaces problems before they escalate, strengthens relationships when they are under strain and helps people achieve more than they thought possible. Few skills are more important. The writer is the CEO of Transforming Engagements Ltd, a Rwanda-based consultancy specialising in organisational culture, leadership development and performance improvement.
