Why Difficult Conversations at Work Feel So Hard – And What My Research Reveals About Making Them Easier

Most people can remember a time at work when they needed to speak up but felt a knot in their stomach instead. Perhaps you had to give feedback, raise a concern, or say something that felt uncomfortable but necessary. In moments like these, many of us hesitate. We wait for the right time, rehearse possible opening lines, or decide that silence might be less risky than speaking honestly.

When I began researching difficult conversations at work, I assumed the main issue would be communication skill. I thought people might simply not know how to approach a sensitive topic or how to phrase things in a way that prevented tension. What I found was far more complex and much more human.

The consistent message across my interviews was that difficult conversations rarely fall apart because of what people say. They fall apart because of everything surrounding the conversation. The conditions, expectations, relationships and emotions shape the outcome long before any words are spoken.

In other words, difficult conversations are not really communication problems. They are relational and organisational problems that show up through communication.

What actually counts as a difficult conversation

Most workplaces treat certain topics as inherently difficult. Performance issues, conflict, feedback, or behaviour concerns are usually assumed to be challenging by default. Yet when I asked participants to define a difficult conversation in their own terms, their answers pointed to something different.

A conversation becomes difficult when something important feels at risk. This might be trust, reputation, belonging, professional identity or a valued relationship. People also spoke about the uncertainty that sits around these interactions. They worried about how the other person might react or how the conversation might change their working relationship. For some, there was anxiety about whether the organisation would support them if the conversation did not go well.

This means the difficulty is less about the topic and more about the stakes. A perfectly ordinary issue can feel daunting if the context is fragile or unclear.

Why we avoid them, and why this reaction makes sense

A common organisational belief is that avoidance reflects weakness or poor capability. My research strongly suggests the opposite. Avoidance often reflects careful thought, emotional awareness and a realistic understanding of the risks involved.

People avoid difficult conversations because they want to protect relationships or because they worry about unintended consequences. They may feel unsure about what is expected of them or whether their concerns will be taken seriously. Many described situations where power differences made honest conversation feel unsafe. If the other person has more authority or influence, speaking openly can feel personally or professionally risky.

This is not a failure of courage. It is a rational response to the environment people are operating in.

The invisible work people do before a difficult conversation

One of the most striking findings from my study was the amount of emotional labour people carry before the conversation even begins. This preparation is often private and unseen, yet it shapes the entire experience.

People described replaying the issue repeatedly in their mind, trying to work out how to phrase things in a way that reduced the chance of conflict. They predicted how the other person might respond and considered all the possible outcomes. Many questioned themselves, wondering if they were overreacting or misunderstanding the situation. Some worried about whether the conversation would be viewed as unprofessional or whether it might damage their relationship permanently.

This mental and emotional effort can be exhausting. Several participants said the anticipation felt worse than the conversation itself. It highlights the importance of the organisational context. When people do not feel supported or safe, the emotional burden increases significantly.

The real problem lies in the conditions around the conversation

People rarely said that their conversations went well because they chose the perfect words. Instead, they talked about feeling respected, having a clear purpose and trusting the person they were speaking with. They appreciated conversations where there were no surprises and where they could express their thoughts without fear of judgement.

When these conditions were present, even difficult topics could be handled constructively. Conversely, when people lacked clarity, trust or safety, conversations that should have been simple became complicated and uncomfortable.

Many organisations respond to difficult conversations by offering communication training. While training can be helpful, it does not address the deeper issue. You cannot expect people to communicate openly in environments that feel unsafe or inconsistent. Skill alone is not enough. The system has to support the behaviour.

Difficult conversations are not inherently negative

It is important to note that participants also shared positive experiences. Many described difficult conversations that strengthened relationships or created greater clarity and alignment. Some felt more confident afterwards or reported improved trust between colleagues. These outcomes were not accidental. They happened when the right foundations were in place.

This suggests that the goal is not to avoid difficult conversations but to create conditions where they can happen more easily and more often.

Key insights from my research

Although I am avoiding heavy bullet lists, there are several central points worth drawing out clearly.

Difficult conversations tend to feel harder when people feel unsafe, when expectations are unclear, when power dynamics are ignored or when there is limited belief that the issue will be taken seriously or acted upon. In contrast, conversations feel easier when the relationship is strong, the purpose is clear and there is enough trust for people to express their thoughts without worrying about negative consequences.

Organisations that understand and support these conditions see better communication, healthier relationships and more effective problem solving. Those that overlook them often end up with avoidance, frustration and unresolved issues that quietly accumulate over time.

What comes next

This blog is the first in a series that explores the findings of my research in more depth.

The next posts will cover topics such as the emotional labour behind difficult conversations, why line managers often struggle, the conditions that make conversations easier and the ways organisations unintentionally make things harder. Later in the series I will offer a practical, human framework for navigating these conversations with more confidence and clarity.