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In most organisations, the hardest conversations are not the ones that go badly. They are the ones that never happen at all.
As a learning designer and facilitator of change in internationally operating organisations, I often hear people say: “Our organisation is going through a transformation.” Strategies are revised, structures are adjusted, and new ways of working are introduced. Yet, beneath all these visible changes, I frequently see another challenge: we struggle to have the conversations that real transformation requires.
I recently worked with an MDF client: an international organisation operating in countries affected by conflict and disasters. Its staff work under considerable pressure, often across cultures, time zones and rapidly changing circumstances. The organisation was adapting its structures and ways of working to respond more effectively to this environment.
During the process, it became clear that the formal changes were only part of the challenge. Teams also needed to talk about workload, trust, decision-making and collaboration. Some colleagues felt that expectations were unclear. Others experienced frustration about how decisions were made or how responsibilities were divided. These concerns were visible in meetings and daily interactions, but they were rarely discussed openly.
This is something I recognise in many organisations. Our environment is changing quickly. Established ways of thinking and working no longer always fit, and patterns need to be questioned or broken. This requires people to speak openly about what is not working, what needs to change, and what they need from one another. But these are precisely the conversations that are often postponed.
Leaders often delay conversations about performance, motivation, or conflict because they feel uncomfortable, are unsure what to say, or worry about hurting the relationship. But avoiding these talks does not solve the problem. Instead, it allows frustration and misunderstanding to grow where there should be clarity.
These conversations require skill more than confidence. Leaders need to give clear feedback, understand what is really behind someone’s behaviour, and agree on specific next steps. Every situation is different. A colleague who lacks clarity or confidence needs a different approach than someone who is unmotivated or avoids responsibility. Treating them the same way is often where things go wrong from the start.
What people often get wrong
Certain common assumptions make these conversations more difficult than necessary.
The first mistake is believing that feedback has to be confrontational. It does not. A conversation can be clear and respectful at the same time. Good feedback focuses on what you observe and its impact, not on someone’s character.
For example, imagine a colleague sends out a report with several errors. If a leader says the work was not careful enough, it sounds like a judgment about the person. If the leader instead points out that the report had figures that did not match the source file and the client questioned the numbers, they are describing what happened and its impact. The second approach is not softer, just clearer and easier for the colleague to address.
The second mistake is jumping too quickly into giving advice. Many leaders think it is their job to provide the solution, so they immediately explain what should happen next. However, asking questions instead of instructing often works better. When colleagues find the answer themselves, they are more likely to act on it because it comes from their own thinking.
For instance, if a colleague keeps missing deadlines, a leader who thinks they know the reason might just remind them to manage their time better. But a leader who asks questions first might discover something else: maybe the deadlines were unrealistic, the workload had grown too much, or the colleague was unsure which task was most important. The right questions can reveal issues that advice alone would miss, such as unclear expectations, too much work, poor team dynamics, low confidence, or not enough freedom to make decisions.
The third mistake is seeing conflict as a sign that a team is not working well. Differences and tension are normal in diverse teams. Amy Edmondson's research on psychological safety at Harvard Business School found that the best-performing teams did not have fewer problems than others. They were simply more willing to speak up about them, discussing mistakes and disagreements openly rather than staying quiet to avoid friction. Handled early and constructively, these differences tend to lead to better decisions and stronger working relationships.
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Here is what that can look like in practice: take two colleagues who disagree in a planning meeting about which approach to take on a project, one wants to start with community consultations, the other wants to finalise the budget first. A leader who reads this as a sign the team is not getting along might step in and pick one option quickly, just to move the meeting forward. A leader who recognises the disagreement as normal is more likely to ask each person to explain their reasoning. That often surfaces a risk or a piece of information neither had considered alone, and the plan that comes out the other side is usually stronger than either starting position.
What changes when leaders get this right
These steps do not take away the discomfort of a tough conversation, but they change what comes from it. When you address issues early, clearly, and with the right approach, you can solve problems before they turn into resentment or distrust. Teams that do this spend less time dealing with tension and more time making progress. This is often what separates teams that avoid problems from those that use them to improve.
Build this into how you lead
MDF's Leadership and People Management course develops exactly the skills this article covers: giving clear feedback, coaching instead of instructing, and reading the difference between a colleague who lacks confidence and one who lacks motivation. Learn more about our training here.
