Difficult workplace conversations are now routine, but many managers lose confidence when emotions rise and listening matters most. Joseph Conway explores why employees feel dismissed, what the psychological safety data reveals, and how L&D can build people’s skills for listening under pressure, with practical strategies that strengthen trust and wellbeing.
Difficult conversations in the workplace are no longer few and far between. For line managers, they’ve become a routine part of leadership, whether it’s navigating performance concerns, responding to interpersonal tensions, or supporting employees through organisational change. Managers are expected to handle these emotionally charged conversations with confidence and care. Yet many are being asked to do so without feeling fully equipped.
Managers lack the confidence to truly listen when conversations become uncomfortable
The challenge isn’t always theoretical knowledge. In many organisations, managers have already been trained in communication techniques, mental health awareness, and employee wellbeing. The problem is often more subtle and overlooked: managers lack the confidence to truly listen when conversations become uncomfortable, emotional, or uncertain. The biggest risk in difficult conversations is not necessarily saying the wrong thing, it’s failing to hear what’s actually being said.
Employees often feel dismissed
When managers rush to solve problems or focus too heavily on “getting through” the conversation, they can overlook important cues. Even with the best intentions, employees can come away feeling dismissed, misunderstood, or judged. Over time, this can erode trust, leave issues unresolved, and can ultimately compromise an individual’s wellbeing.
Research helps to highlight the scale of the issue. 45% of employees say they do not feel comfortable raising issues at work, including flagging mistakes or potential risks. As a result, employees are remaining quiet about other issues, almost half said they do not feel comfortable expressing their needs at work, while 35% claim they do not feel safe asking for help.
The consequences are not only personal, but organisational too. Reluctance to speak up is contributing to preventable mistakes, with 15% of workers admitting they’ve made errors because they felt stressed, unsafe, or unable to raise concerns. Meanwhile, just over three in ten employees aged 18 to 24 have considered leaving their role because they do not feel psychologically safe at work.
Understanding active listening and practising it are two different things
For L&D professionals this presents a growing challenge. If organisations want better workplace conversations, training managers in listening techniques alone is not enough. As a psychotherapist and workplace mental health trainer, I often see managers who understand active listening in principle but struggle to apply it in practice once emotions enter the room. Most worry about making things worse, saying the wrong thing, or not having the answers, all entirely understandable concerns.
As a result, managers can unintentionally retreat into surface-level responses or problem-solving mode, rather than genuinely listening. But active listening is one of the most powerful tools managers have. When people feel heard without interruption or judgement, conversations tend to become more honest and productive, and employees are far more likely to open up about challenges early, before problems escalate.
Six practical strategies to help managers listen with confidence
Managers do not need to become therapists. Often, employees are not looking for solutions; they simply want to feel acknowledged, understood, and supported. In the same sense, the expectation is not for managers to have the answers, but for them to stay present in difficult conversations.
That confidence is something that can be developed. L&D teams need to shift focus from simply teaching listening as a skill, to helping managers feel capable of using it under pressure. Here are six practical strategies that can help managers in these moments:
1. Stay present in the conversation
In difficult conversations, distractions can quickly undermine trust. Hybrid and remote working have made this even more challenging, with managers often multitasking during conversations without realising the impact.
Intentional listening requires full attention. Close email tabs, silence notifications, and remove anything that competes for focus. Presence communicates value and employees can usually tell when someone is only half listening.
2. Learn to tolerate silence
One of the biggest signs of listening confidence is the ability to sit with silence without rushing to fill it. Many managers become uncomfortable when conversations pause, particularly when emotions are involved. The instinct is often to reassure, advise, or move things forward quickly. Silence can give employees the space they need to process thoughts, regulate emotions, and speak more openly.
L&D programmes should work to normalise this discomfort. Silence is not failure; often, it’s where the most meaningful part of the conversation begins.
3. Pay attention to non-verbal communication
Listening is about far more than hearing words. Tone of voice, posture, facial expressions, and pace of speech all provide important context. Managers should also remain aware of their own non-verbal signals. Eye contact, nodding, and open body language help demonstrate attentiveness and empathy. Small behaviours can have a significant impact on whether someone feels safe enough to continue speaking honestly.
4. Ask open questions instead of jumping to solutions
Managers can be conditioned to solve problems quickly. But difficult conversations usually require curiosity before action. Open questions encourage employees to expand on what they’re experiencing and help managers understand the issue more fully.
Questions such as, “Can you tell me more about that?” or “What feels most difficult at the moment?” create space for reflection and dialogue. This approach also reduces the pressure managers often place on themselves to immediately “fix” the situation.
5. Reflect back what you’ve heard
One of the simplest and most effective listening techniques is summarising and reflecting. Reflection also slows conversations down, helping managers remain thoughtful rather than reactive. Phrases such as, “What I’m hearing is…” or “It sounds like…” help confirm understanding and give employees an opportunity to clarify if needed. This demonstrates that the manager is genuinely engaged, rather than waiting for their turn to respond.
6. Be consciously non-judgemental
Employees quickly sense when they’re being evaluated or criticised. Even subtle judgement can shut conversations down. Remaining neutral doesn’t mean agreeing with everything being said. It means creating a space where employees feel able to speak honestly without fear of blame or dismissal. This is particularly important during conversations around mental health, stress, or interpersonal conflict.
Listen for the opportunity
For organisations investing in management capability, this is the real opportunity. Technical listening skills matter, but confident listening is what allows those skills to be used effectively when conversations become difficult.
As workplace pressure intensifies and expectations on managers continue to grow, listening should no longer be viewed as a “soft skill”. Instead, it should be viewed as a core leadership capability, directly influencing wellbeing, engagement, retention, and trust.
Joseph Conway is a Mental Health Trainer and Psychotherapist for Vita Health Group
