Article 10: Maybe there is no such thing as a “difficult conversation”

I have spent a considerable amount of time researching difficult conversations at work, which makes what I am about to say slightly inconvenient.

I am no longer entirely convinced that there is such a thing as a “difficult conversation”.

At least, not in the way we commonly use the term.

We talk about difficult conversations as though they are a recognisable category of workplace interaction. Giving negative feedback is difficult. Talking about poor performance is difficult. Addressing conflict is difficult. Disclosing a health condition is difficult. Challenging inappropriate behaviour is difficult. Asking for an adjustment is difficult. Talking about wellbeing is difficult.

But the more closely I have looked at these conversations, the less convincing that categorisation becomes. The same conversation can be almost routine for one person and enormously difficult for another. A conversation that feels manageable with one manager can feel impossible with another. Something we have discussed comfortably many times can suddenly become difficult when the circumstances, relationship or consequences change.

Perhaps the difficulty does not actually belong to the conversation at all.

Perhaps it emerges from everything surrounding it.

We have become very good at categorising conversations by topic

Much of the workplace advice around difficult conversations begins by identifying particular kinds of conversations that people find challenging. Performance management, feedback, conflict and underperformance feature heavily, which makes sense given how organisations traditionally think about workplace communication.

There is then usually a model, framework or set of techniques designed to help someone navigate that particular type of interaction.

The difficulty with this approach is that it can quietly encourage us to assume that the topic explains the difficulty.

But consider feedback. I might be perfectly comfortable giving feedback to a colleague I know well, trust and have worked with for years. The same feedback delivered to a senior person who controls an opportunity important to me may feel considerably more difficult.

Equally, feedback from someone whose judgement I trust might be uncomfortable but useful, while relatively mild feedback from someone with whom I have a difficult relationship may feel threatening.

The content has not necessarily changed very much. The relational and psychological context has.

The same is true of conversations about health. Telling a trusted colleague that I am struggling may feel relatively easy. Telling a new manager the same thing when I am uncertain how that information will affect their perception of my capability may feel completely different.

Calling both of these “health conversations” tells us what they are about. It tells us surprisingly little about why one feels easy and the other does not.

Difficulty seems to sit in the combination

This was one of the things that became increasingly clear through my research. People did not describe conversational difficulty as though it existed neatly within particular topics.

Their experiences were shaped by combinations of factors: who they were talking to, what the conversation involved and whom the issue concerned, alongside power, vulnerability, relationship, previous experience and anticipated consequences.

Change one part of that combination and the experience can change with it.

A conversation about somebody else's wellbeing may feel very different from talking about our own. Giving feedback to someone we manage may feel different from giving exactly the same feedback to our manager. Raising a problem with a colleague we trust may feel different from raising it with somebody with whom the relationship is already strained.

This is why I have become interested in thinking about difficult conversations as existing on a continuum rather than dividing workplace interactions into “difficult” and “not difficult”.

Difficulty moves.

It can increase or decrease according to the person, relationship, timing, context and what we believe might happen next. The conversation does not need to change dramatically for our experience of it to change substantially.

That creates a very different starting point for understanding what people need.

The conversation I find difficult may tell you very little about the one you find difficult

One of the risks of treating difficulty as an objective characteristic of particular conversations is that we begin designing support around what organisations assume people should find difficult.

We then risk missing the enormous variation in individual experience.

For one employee, giving critical feedback may be relatively straightforward while receiving it is extremely uncomfortable. Another may be comfortable discussing performance but find conversations involving emotion almost impossible. Someone else may have no difficulty challenging senior leaders about work but struggle enormously to ask their own manager for help.

None of these people is necessarily more or less capable of having difficult conversations.

They are responding to different forms of perceived risk.

That distinction matters because otherwise we can start making judgements about what people should find difficult. We might wonder why someone is anxious about what appears to us to be a relatively minor interaction or assume that because we would be comfortable raising something, they should be too.

But we are not entering their conversation with their history, their relationship, their identity or their perception of what is at stake.

Perhaps one of the most useful things we can do is stop deciding the difficulty of somebody else's conversation for them.

Power can turn an ordinary conversation into a difficult one

Power is a particularly good example of why the label itself can be misleading.

“Giving feedback” sounds like a type of conversation. Yet telling someone you manage that their work needs improving and telling the person who controls your progression that their behaviour needs improving are psychologically very different acts.

Both are feedback.

Only one requires you to challenge somebody with considerably greater organisational power than you.

This is why telling people to use the right communication technique can feel inadequate.

The employee may know perfectly well how to phrase their concern constructively. Their hesitation may have very little to do with finding the words and considerably more to do with what the person receiving those words can do afterwards.

The same applies to disclosure. Saying “I need to tell my manager about my health” sounds like a communication problem until we consider everything else attached to that sentence: privacy, identity, capability, stigma, career consequences, previous experience and uncertainty about who will know next.

Suddenly, the difficulty looks less like a property of the conversation and more like a response to the conditions surrounding it.

We may be trying to fix the wrong thing

This is where the language of “difficult conversations” can become more than a semantic issue.

If we assume the conversation itself is difficult, our intervention naturally focuses on helping the individual manage it. We give them a framework, a script, some training and perhaps a chance to practise. We build their confidence and teach them how to regulate their response.

All of those things can be useful.

But what happens if the person is already capable of having the conversation and the environment is what makes having it feel unsafe?

No amount of perfect phrasing removes a genuine power imbalance. Communication training cannot guarantee that disclosure will not affect how somebody is perceived. A feedback model cannot compensate for a manager who consistently responds defensively to challenge. Assertiveness training does not change an organisational culture in which people have learned that raising problems carries consequences.

At that point, asking how we can make the employee better at difficult conversations may be the wrong question.

Perhaps we should be asking what has made this particular conversation so difficult in the first place.

Difficulty can also be created between people

There is another implication here that I think organisations need to take seriously. If difficulty is relational rather than fixed, then managers and leaders can inadvertently increase or reduce it.

The same employee with the same communication skills may become much more willing to raise concerns with a manager who has repeatedly demonstrated that disagreement is tolerated, mistakes can be discussed and personal information is handled responsibly.

Conversely, relatively ordinary conversations can become increasingly difficult in relationships characterised by unpredictability, defensiveness or low trust.

This means that someone's reluctance to have a difficult conversation cannot always be understood by looking at them in isolation.

We need to look at the relationship they are having it within.

We also need to look at the organisation surrounding that relationship. What happens when people challenge? How are mistakes treated? How much control do employees have over personal disclosure? Are managers rewarded only for performance outcomes, or also for how they create the conditions in which people can communicate honestly?

The difficulty may be telling us something about far more than the conversational ability of the individual.

Perhaps “difficult” is an outcome of appraisal

I think a more useful way of understanding these interactions is to consider what happens when somebody first realises that something needs to be said.

They begin making judgements, sometimes very quickly and sometimes over a considerable period of time. Who am I talking to? What is our relationship like? How important is this? How personal is it? What might happen if I say something? What might happen if I do not? Do I trust this person? Do I feel able to manage their response? Is there any realistic possibility that speaking will improve the situation?

It is through that process that difficulty starts to emerge.

Two people can therefore encounter apparently identical situations and arrive at very different conclusions about how difficult the conversation feels. Neither is necessarily wrong. They are appraising different risks through different experiences.

This also helps explain why our own perception of a conversation can change. Something we avoided earlier in our career may feel manageable now because we have greater confidence, security or organisational power. Equally, a conversation we previously found easy can become much harder following a negative experience.

Difficulty is not fixed because neither we nor our circumstances are fixed.

So should we stop calling them difficult conversations?

Probably not.

The term is useful precisely because people recognise it. When somebody says they need to have a difficult conversation, most of us understand something about what they mean.

There is emotional weight attached to the interaction, something feels at stake and they are anticipating that it may be uncomfortable.

I am less interested in getting rid of the term than in challenging what we assume it tells us.

“Difficult conversation” should perhaps be the beginning of our curiosity rather than the diagnosis.

Instead of immediately reaching for a script, we could ask what is making this conversation difficult for this person, with this individual, at this moment.

Is it the topic? The relationship? Power? Vulnerability? Previous experience? Identity? Uncertainty? The anticipated response? The potential consequences?

The answer matters because each requires something different.

And perhaps that is the argument I have arrived at after spending years studying difficult conversations: there may be no particular type of conversation that is inherently difficult.

There are conversations that become difficult when something important feels at risk.

If we want better conversations at work, perhaps our job is not simply to make people more skilled at having them. It is to become much more interested in the conditions that make ordinary human conversations feel extraordinarily difficult in the first place.