Article 1: We Train People for Conversations They May Never Feel Able to Start
Updated: Aug 22

There is no shortage of advice about how to have a difficult conversation at work. Prepare what you want to say, choose the right moment, stick to the facts, ask open questions, listen properly, manage your emotions, show empathy and be clear about what needs to happen next. It is mostly good advice. Communication skills matter, and poorly handled conversations can cause considerable harm. But the more I have researched difficult conversations, the more I have found myself wondering whether we are starting in the wrong place.
Most of the advice we give assumes that something quite significant has already happened: the person has decided to have the conversation. Yet sometimes that is the hardest part.
Think about the last conversation at work that felt genuinely difficult. Not simply an awkward meeting or a piece of feedback you would rather not have given, but something that mattered to you. Perhaps you needed to tell your manager that you were struggling, challenge something you believed was wrong, disclose something about your health, ask for an adjustment, address the behaviour of a colleague, admit that you had made a mistake, or tell somebody that something they had done had affected you. When did that conversation actually begin?
I would argue that it probably wasn't when you opened your mouth. It may have started days, weeks or even months earlier, when you first noticed something and began wondering whether it mattered enough to raise. You probably thought about who you would need to speak to and imagined how they might respond. You may have considered what could happen if the conversation went badly, rehearsed sentences in your head, changed them several times and decided that you would mention it at your next one-to-one. Then the one-to-one arrived and somehow the moment did not feel right. Perhaps you told yourself you were overreacting, decided to wait and see whether things improved, spoke to somebody else first, or drafted an email and left it sitting unsent. Eventually, you may have had the conversation. Or perhaps you never did.
That entire process is largely invisible to organisations, yet my doctoral research into difficult conversations at work has made me increasingly convinced that it is one of the most important parts of the conversation.
The conversation before the conversation
We tend to treat difficult conversations as communication events. Someone says something, somebody responds, and afterwards we can judge whether the conversation was handled well. Psychologically, however, there can be an enormous amount happening before either person speaks. There is anticipation, appraisal, emotion, uncertainty and an assessment of risk. We are not simply deciding which words to use; we are trying to predict what using those words might cost us.
That distinction matters because knowing what to say is not the same as feeling able to say it. Psychology has long recognised a gap between intention and behaviour. People can genuinely intend to do something and still fail to act, and Sheeran and Webb's (2016) review of the intention-behaviour gap demonstrates how significant that distinction can be across human behaviour. My own research suggests that it is equally important when we think about difficult workplace conversations.
Someone can recognise that a conversation needs to happen, know exactly what they want to say and possess perfectly good communication skills. They may even have attended training specifically designed to help them navigate difficult conversations, yet still avoid having it. This became one of the questions I found increasingly interesting during my research: what happens in the space between I need to say something and actually saying it?
Because that space is not empty.
Perhaps we have mistaken capability for readiness
One of the behavioural frameworks I drew upon in my research was COM-B, developed by Michie, van Stralen and West (2011). At its simplest, COM-B proposes that behaviour depends upon the interaction of capability, opportunity and motivation. It offers a useful way of thinking about difficult conversations because it moves us beyond the assumption that behaviour is simply a question of whether somebody knows what to do.
Capability clearly matters. People need the knowledge and skills to communicate effectively, particularly when conversations are emotionally charged. Opportunity matters too because people need an environment in which the behaviour is realistically possible. But there is also motivation: whether, in that particular situation and at that particular moment, someone feels sufficiently willing and able to act. In my own research,
motivation emerged as particularly important, and that complicates the way we often approach difficult-conversation training.
Imagine an employee who is concerned about something happening within their team. They have completed communication training, understand assertiveness, know how to structure feedback and have repeatedly been told that the organisation values openness. Their manager regularly says that their door is always open. On paper, this person appears perfectly equipped to speak. Yet they have also watched their manager become defensive when challenged, remember what happened to a colleague who raised a concern six months earlier, are waiting to hear whether they have been promoted, worry that speaking could alter an important relationship, and are not particularly convinced that anything will change anyway.
Does that person really need another communication workshop? Perhaps, but probably not for the reason we think.
Sometimes silence makes sense
This is where some organisational conversations about speaking up become uncomfortable. We often interpret silence or avoidance by looking for something that is missing within the individual. Perhaps they lack confidence, need to become more assertive, dislike conflict, lack resilience or simply need better communication skills. Sometimes those explanations will be right, but they are not the only explanations, and assuming that they are can place responsibility in entirely the wrong place.
Employee voice research has long demonstrated that speaking at work involves judgements about risk and potential consequences. Morrison's (2011, 2014) work on employee voice and silence, for example, shows that decisions to speak are shaped by individual and contextual factors, including whether people believe that speaking is safe and likely to make a difference. Psychological safety is also relevant. Edmondson's (1999) foundational work conceptualised psychological safety in relation to whether a team is safe for interpersonal risk-taking. I think that idea of interpersonal risk becomes particularly important when we turn our attention to difficult conversations.
Speaking can carry risk without that risk being as dramatic as losing a job or facing formal consequences. People may wonder whether a manager will think differently about them, whether disclosing a difficulty will make them appear less capable, whether challenging a colleague will permanently change the relationship, whether they will be labelled difficult, whether they will be believed, or whether raising the issue will simply make an already uncomfortable situation worse. When the conversation concerns health, identity, wellbeing, discrimination, interpersonal conflict or something deeply personal, these judgements can become even more significant.
Seen from this perspective, avoidance starts to look rather different. Someone who remains silent has not necessarily failed to be brave enough. They may be making a perfectly understandable assessment of the environment around them and concluding that, for now at least, the potential cost of speaking is greater than the potential benefit.
Are we asking people to be courageous in environments that require too much courage?
I understand why organisations talk about courageous conversations. We want people to speak. We want managers to address problems rather than allow them to grow, employees to challenge inappropriate behaviour and teams to discuss disagreement rather than quietly accumulate resentment. There is something appealing about encouraging people to be courageous, but I increasingly wonder what that language places on the individual.
If a conversation requires courage, perhaps we should also be curious about why so much courage is necessary.
There is a danger that organisations repeatedly ask employees to become braver while leaving untouched the conditions that make bravery necessary. We can teach people to speak up in cultures where challenge is quietly punished, teach managers how to invite feedback without examining what happens when the feedback they receive is uncomfortable, and encourage employees to disclose personal difficulties without paying sufficient attention to what happens after that disclosure. An organisation can tell people that its door is always open, but employees will form their judgement about whether to walk through it from what they have seen happen to themselves and others.
That is why culture matters so much here. Organisational culture is not simply what is written in a values statement or communicated during a leadership programme. It is also what people learn through experience about what is welcomed, tolerated, ignored and punished. Every difficult conversation, and every response to one, therefore teaches people something about whether it is worth having the next one.
Training matters, but perhaps it needs to begin earlier
None of this means that we should stop teaching communication skills. Knowing how to listen, ask useful questions, regulate emotion, communicate clearly, respond without immediately becoming defensive and navigate disagreement constructively can make an enormous difference. Difficult conversations can cause real harm when they are handled badly, even when the intentions behind them are good.
But communication skills are only one part of the picture. If we want to support people properly, preparation may need to begin before we start constructing the perfect opening sentence. We need to understand what someone believes could happen if they speak, what they are trying to protect, what makes this particular conversation feel risky and what previous experiences they are carrying into it. We also need to consider whether the risk is primarily emotional, relational, professional or structural, because those different forms of difficulty are unlikely to be solved in the same way.
Most importantly, we need to distinguish between someone avoiding a conversation because they do not know how to have it and someone avoiding it because they do not believe it is safe, worthwhile or possible to have it. The answer matters because it changes the support required. A genuine skills gap might benefit from training, while uncertainty or low confidence might be better addressed through practice or coaching. If hesitation comes from a damaged relationship, however, another communication framework does little to rebuild lost trust. Where the barrier lies in hierarchy, power or psychological safety, placing responsibility back on the individual to communicate more effectively risks missing the problem altogether.
This is why I am increasingly sceptical of generic approaches to difficult-conversation training. We can teach the words, but the words are only useful if somebody reaches the point at which they feel able to use them.
We tend to train the part we can see
Perhaps this is ultimately the problem. Organisations notice a difficult conversation once somebody speaks because that is the visible part. We can observe the meeting, assess the manager, practise the script, teach a framework and evaluate what happened afterwards. What we cannot easily see is the psychological process underneath it: the noticing and appraisal, the worry and internal negotiation, the imagined consequences, the sentence rehearsed on the drive to work, the conversation nearly started on Tuesday, the email written and deleted, and the repeated decision to wait until a better moment.
By the time somebody finally says, "Can I talk to you about something?", they may already have been having that conversation internally for weeks.
My research has made me increasingly uncomfortable with the assumption that somebody who avoids a difficult conversation necessarily needs to become better at having difficult conversations. Sometimes they might. But sometimes the much more revealing question is what made this conversation so difficult to begin with.
That question takes us beyond communication technique and towards relationships, leadership, culture, power and organisational systems. It asks us to consider not only whether employees have been equipped to speak, but what happens when they do. It asks managers not simply whether they invite difficult conversations, but whether their behaviour makes a second conversation more or less likely. And it asks organisations to consider whether silence is always an individual problem, or whether sometimes it is feedback about the environment people are being asked to speak within.
If we genuinely want workplaces where people can talk about the things that matter, perhaps that is where difficult-conversation training needs to begin. We still need to help people think about what they might say, but we also need to become much more interested in what needs to be true around them for saying it to feel possible.
Because sometimes the most important part of a difficult conversation happens long before anybody speaks


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