Article 6: The difficult conversation starts long before anybody speaks

When we talk about difficult conversations at work, we tend to focus on the moment the conversation actually happens. We think about what was said, how it was said, whether somebody became defensive, whether emotions were managed effectively and whether the people involved eventually reached some kind of resolution. Most of the advice available to us follows the same pattern. Prepare what you want to say, choose your words carefully, listen actively, regulate your emotions and try to keep the conversation constructive.

There is value in all of that, but I increasingly think it starts too late.

For many people, the difficult conversation has already been happening internally for days, weeks or sometimes months before another person hears a single word. If we only pay attention to the visible interaction, we miss a substantial amount of the psychological work involved in getting there and, perhaps more importantly, we miss what determines whether the conversation happens at all.

The conversation nobody else can see

It often starts with awareness that something is not quite right. Perhaps a colleague's behaviour has begun to bother you, your workload has become unsustainable, you need to tell your manager about a health condition, you disagree with a decision or something has happened that you believe is unfair. You might need an adjustment, want to challenge inappropriate behaviour, raise a concern about somebody else or give feedback you know will be uncomfortable to receive.

At that point, nothing observable may have happened. You have not booked the meeting, written the email or approached the person, but internally you may already be trying to decide what to do. You think about whether the issue is important enough to raise, replay what happened and question whether you interpreted it correctly. You imagine how the other person might respond, rehearse what you could say and then think of all the reasons that particular version might go badly. Perhaps you talk to somebody you trust, write an email and leave it sitting in drafts, or decide that tomorrow will be the day you finally say something.

Then tomorrow arrives and somehow it does not feel quite right.

From the outside, this can look like nothing is happening. From the perspective of the person contemplating the conversation, there may already have been considerable cognitive and emotional effort.

What looks like delay may actually be appraisal

We can be remarkably impatient with this stage of the process. When someone eventually tells us that they have been worried about something for weeks, one of the obvious responses is to wonder why they did not raise it sooner. In workplaces particularly, there is often an assumption that earlier communication would have prevented the issue from becoming more complicated, and sometimes that is undoubtedly true.

What interests me, however, is what was happening during those weeks.

The person may have been trying to establish what speaking would mean for them. They may have been thinking about whether they would be understood, whether the other person would become angry or defensive, whether they were overreacting, whether they could explain themselves clearly enough, whether becoming emotional would undermine what they were trying to say, or whether raising the issue might damage a relationship they still need to maintain afterwards. They may also be weighing something even more fundamental: whether anything useful is likely to happen as a result.

When power is involved, that appraisal can become considerably more complicated. Telling a colleague that something they said upset you is different from telling the manager who assesses your performance that their behaviour is affecting your wellbeing.

Questioning a decision among peers is different from challenging the senior leader who made it. Disclosing a health condition or disability may involve deciding whether the support you might gain is worth the uncertainty created by revealing information you cannot subsequently take back.

Seen from that perspective, hesitation begins to look rather different. What we describe as procrastination or avoidance may involve somebody making a perfectly serious assessment of risk, consequence and possibility.

We can have the conversation many times before we actually have it

Most of us probably recognise the experience of mentally rehearsing a difficult interaction.

We practise an opening sentence, imagine the other person's response and then construct our response to the response they have not actually given us. We try to anticipate objections, decide how much detail to share and think about how we will keep ourselves composed. We may worry that sounding too emotional will weaken our position while simultaneously worrying that sounding too calm will fail to communicate how much the issue matters.

By the time the conversation finally happens, one person may therefore have mentally experienced several different versions of it. They may have anticipated conflict, rejection, understanding, embarrassment, relief and regret before they even enter the room.

The other person may have experienced none of this.

That creates an interesting imbalance that is easily overlooked when we judge what happens next. One person may arrive having spent three weeks preparing emotionally and cognitively for the interaction, while the other has had thirty seconds to process what they have just heard. We then look at the behaviour of both people during the meeting as though they entered it from the same psychological starting point.

They did not, and understanding that difference may help explain some of the reactions that otherwise appear surprising. Someone who has spent weeks worrying about a disclosure may become emotional almost immediately. Someone receiving unexpected criticism may become defensive before they have had time to understand what is being said. Neither response exists solely within the few minutes we can observe.

Preparation can become part of the problem

We quite reasonably encourage people to prepare for difficult conversations. Good preparation can help clarify what matters, distinguish assumptions from evidence and make it easier to communicate something coherently. However, I think there is a point at which preparation can stop increasing readiness and begin feeding hesitation.

Thinking through one possible outcome reveals another risk, which prompts another rehearsal, which creates another question about what might happen. The individual becomes increasingly prepared in terms of what they could say while becoming progressively less certain that they should say anything at all. What begins as planning can gradually become rumination.

This became particularly interesting in my research because people's accounts did not suggest a neat progression from recognising a conversation was needed, preparing for it and then having it. There was much more movement backwards and forwards. People assessed the situation, considered acting, reconsidered the risks, delayed, prepared again and sometimes returned almost to the beginning of the process.

That is why I have become cautious about treating avoidance as though it is simply the absence of behaviour. Someone may ultimately decide not to have the conversation, but that decision can sit at the end of a very active psychological process involving considerable thought, emotion and effort. Silence tells us what somebody ultimately did. It does not necessarily tell us how much happened before they did it.

The emotional work begins before the meeting

There is a similar issue with the way we think about emotion. Difficult-conversation advice often concentrates on regulating emotion during the interaction itself, but the emotional work may have begun long before the meeting invitation appeared in anybody's calendar.

Someone preparing to disclose a health condition may already be managing fear about how they will subsequently be perceived. A manager preparing to give difficult feedback may be worrying about upsetting somebody or damaging a previously positive relationship.

An employee preparing to challenge their manager may be simultaneously angry about what has happened and anxious about the consequences of saying so.

By the time the conversation takes place, that emotional effort may have accumulated considerably. This matters because we can otherwise misinterpret what happens in the room. Tears that appear surprisingly quickly, frustration that seems disproportionate to the immediate exchange or somebody suddenly struggling to articulate something they had planned carefully can make much more sense when we understand that the interaction has a history.

The conversation might have started five minutes ago for the person receiving it. For the person initiating it, this may simply be the first time the internal conversation has become audible.

If this is where difficulty develops, this is where support needs to begin

Once we understand difficult conversations in this way, conventional support starts to look somewhat incomplete. Teaching people what to say remains useful, but we also need to understand what is happening while they are deciding whether to say it.

That means asking different questions. What is the person actually worried about? Is the barrier uncertainty about how to communicate, or uncertainty about what will happen when they do? Are they struggling to find the words, or do they know exactly what they want to say but do not trust the environment into which they would be saying it? Is additional preparation increasing their readiness, or has preparation become a way of remaining safely outside the conversation?

These questions also shift some of our attention away from the individual and towards the organisation. If people routinely spend weeks trying to decide whether it is safe to raise ordinary concerns, it is difficult to argue that the answer is simply better communication skills. We also need to examine what is creating the hesitation. Perhaps disagreement has historically been poorly received, previous concerns have disappeared without action, managers are comfortable discussing tasks but uncomfortable with emotion, or formal channels exist without employees trusting what happens when they use them.

In those circumstances, the person may indeed need support to have the conversation, but the organisation also needs to understand why so much psychological effort was required to get there.

The process continues after people stop speaking

Thinking about difficult conversations as processes rather than isolated interactions also means recognising that they do not necessarily finish when the meeting ends. Afterwards, people often begin another period of interpretation. They think about whether they explained themselves properly, whether the other person really understood, what a particular reaction meant and whether they should have said something differently. They may wonder whether the relationship has changed, whether anything will happen next and, particularly following disclosure, whether they will now be seen differently.

What happens in the days and weeks afterwards can also shape the next difficult conversation. If speaking resulted in respect, support and meaningful action, the individual has gained evidence that raising something difficult can be worthwhile. If it resulted in dismissal, defensiveness, embarrassment or consequences they had feared, they have learned something very different.

Every difficult conversation therefore has the potential to alter the conditions surrounding the next one. Previous experiences become part of future appraisal, which means organisations are not starting from zero each time they encourage somebody to speak.

People bring histories with them, including histories of what happened when they, or people around them, tried before.

Perhaps we are intervening too late

This is ultimately why I think we need to broaden what we mean when we talk about supporting difficult conversations at work. If our intervention begins when somebody is already sitting opposite another person trying to remember the communication model they learned on a training course, much of the psychologically important work has already happened.

The difficult conversation may have begun when somebody first noticed there was something they needed to say. Everything that follows, the appraisal of risk, the imagined consequences, the emotional regulation, the rehearsal, the delay, the decision to act and sometimes the decision to retreat again, shapes whether the visible conversation ever takes place.

Understanding that process also gives us a different way of thinking about silence. Instead of assuming that nothing happened because nothing was said, we can become curious about what prevented thought from becoming speech. We can ask what tipped somebody towards action, what pulled them back towards avoidance and what conditions would have made engagement feel more possible.

Because if we really want to understand difficult conversations at work, we cannot begin our analysis when somebody finally starts speaking. By that point, we may already be well into the story.