Article 8: There are two people in a difficult conversation, but only one may know they’re having one

There is something about difficult conversations that I do not think we pay enough attention to: the two people involved may arrive at exactly the same interaction from completely different psychological starting points.

One person may have spent days or weeks thinking about it. They have replayed events, questioned their interpretation, rehearsed what they want to say and imagined how the other person might respond. They may have spoken to friends or colleagues, written notes, deleted emails, lost sleep over it and finally reached the point where they feel ready enough to speak.

Then they say, “Can I talk to you about something?”

For the other person, the conversation has just begun.

We often evaluate what happens next as though two equally prepared people have entered an interaction together. I am increasingly convinced that this difference in preparedness may explain a great deal about why some difficult conversations go wrong.

One person has had weeks. The other has had seconds.

Imagine telling your manager that something they have been doing is affecting you negatively. You have spent considerable time trying to find a way of explaining it that feels fair. You have thought carefully about examples, tried not to make assumptions about their intentions and perhaps worried about whether saying anything could affect your relationship.

By the time you finally raise it, you are likely to have processed at least some of your initial emotional response. You know what the issue is, you know why it matters to you and you have some idea of what you hope might happen next.

Your manager may be hearing for the first time that their behaviour has been experienced as a problem.

They have not had the benefit of your preparation. They may simultaneously be trying to understand what you are saying, remember the events you are describing, work out whether they agree with your interpretation and manage their own emotional reaction to discovering that somebody has experienced them in a way they did not intend.

If their immediate response is defensive, we may understandably judge that response negatively. Sometimes defensiveness is damaging, particularly where there is a significant power imbalance. But I also think there is value in understanding where it comes from, because understanding a response is not the same as excusing its impact.

We are asking somebody to process potentially threatening information in real time while another person has already had considerable time to make sense of it.

The person initiating the conversation may already be several steps ahead

This difference becomes even more apparent when the conversation involves something deeply personal.

An employee disclosing a health condition, for example, may have spent weeks deciding what to share, researching possible adjustments, anticipating questions and thinking about what they need from their manager. They may arrive at the conversation with a relatively clear idea of what they want.

The manager may be trying to process several things at once. They might be concerned about the employee, unsure what they are allowed to ask, worried about saying the wrong thing, thinking about workload implications and trying to remember what organisational support is available.

The employee may interpret hesitation as discomfort with the disclosure. The manager may simply be trying to process unfamiliar information responsibly.

Equally, the manager's good intentions do not mean their response cannot cause harm.

They might immediately start offering solutions when the employee wanted to be heard, ask intrusive questions because they think showing interest is supportive, or unintentionally communicate concern in a way that makes the employee feel newly perceived as fragile or incapable.

Both people are trying to navigate the same conversation, but they may be doing so with completely different levels of preparation, knowledge and emotional readiness.

Surprise changes behaviour

We tend to have fairly high expectations of people during difficult conversations. We want them to listen calmly, remain curious, avoid defensiveness, regulate their emotions and respond thoughtfully. Those are reasonable aspirations, particularly for managers and leaders whose reactions can have significant consequences.

But difficult information can be psychologically threatening.

Being told that you have hurt somebody, that your leadership has created a problem, that an employee does not feel supported by you, or that something you thought was working well is not can challenge the story you hold about yourself. Even when feedback is delivered carefully, the recipient may experience an immediate need to explain, correct or defend.

The problem is that the person speaking may interpret that first response as the answer to a much bigger question: Was I right to tell you?

That is where asymmetrical preparedness becomes particularly important. One person's relatively ordinary moment of surprise may be experienced by the other as confirmation of weeks of anticipated risk.

A manager might say, “I didn't realise you felt like that,” because they are genuinely surprised. An employee who has spent weeks worrying about whether their experience will be believed might hear disbelief.

A colleague might ask, “Why didn't you tell me sooner?” because they wish they had known. The person raising the issue might hear blame for not speaking earlier.

The intention and impact of a response can diverge very quickly when people arrive carrying different histories of the conversation.

Perhaps the first response does not need to be the final response

This makes me wonder whether we need to give people more permission not to resolve difficult conversations immediately.

There can be a strong desire to sort things out in the room. We want the conversation to end constructively, agree actions and achieve closure. In some situations that is entirely appropriate, but in others it may place unrealistic demands on the person who has only just discovered that there is something to process.

Sometimes a genuinely constructive response might be, “I want to think properly about what you've told me before I respond.”

That does not mean shutting the conversation down or leaving somebody indefinitely without an answer. It means recognising that thoughtful processing can be preferable to an immediate response produced under emotional pressure.

The important part is what happens afterwards. If somebody asks for time, they need to return to the conversation. Otherwise, what was intended as reflection can easily be experienced as avoidance.

Creating space for a second conversation may sometimes produce a better outcome than demanding that two people with completely different levels of preparedness somehow reach understanding within the first one.

This matters for the person initiating the conversation too

There is also something useful here for those of us preparing to raise something difficult.

When we have spent a long time thinking about an issue, it is easy to forget that the other person has not been part of that internal process. We may arrive with a carefully developed understanding of what has happened and expect them to grasp it immediately.

Their questions can then feel frustrating. Their surprise can seem implausible. Their need to think can feel like resistance.

Sometimes it will be resistance. Sometimes people genuinely do respond poorly to challenge, vulnerability or feedback. Power matters, and we should not use surprise as a convenient explanation for behaviour that is dismissive, aggressive or harmful.

But sometimes the other person simply needs time to get to where we already are.

Recognising that does not mean reducing our expectations of respectful behaviour. It means recognising that listening well and processing quickly are not necessarily the same thing.

Managers may need particular preparation for being unprepared

There is a paradox here for leaders. They cannot prepare for every difficult conversation somebody might unexpectedly bring to them, but they can prepare for the experience of not being prepared.

That may be a much more useful leadership capability than memorising the perfect response.

Managers can learn to notice their own defensiveness, tolerate uncertainty and resist the pressure to immediately explain or solve. They can become comfortable saying that they do not know something and need to find out. They can learn which questions create understanding and which ones unintentionally interrogate. Most importantly, they can understand that the way they respond in the first few moments may carry disproportionate weight for somebody who has taken a significant risk in speaking.

Perhaps that is part of what being approachable actually requires. Not always knowing what to say, but being able to receive something unexpected without making the other person regret saying it.

Difficult conversations do not necessarily begin at the same time

I think this changes how we understand difficult conversations more broadly. We often imagine two people entering a shared interaction, but psychologically they may be entering at very different points.

One may already have experienced awareness, appraisal, hesitation, preparation and emotional processing before the other even knows there is an issue. The visible conversation brings those two processes together, but it does not erase their different histories.

That helps explain why reactions can become misaligned so quickly. One person wants resolution while the other is still trying to understand the problem. One has processed their strongest emotions while the other's have only just been activated. One interprets the conversation through weeks of anticipation while the other is responding to information received moments ago.

Perhaps better difficult conversations therefore require something more than good communication. They require an awareness of time, preparation and perspective, including the possibility that the person sitting opposite us is not psychologically standing in the same place.

Because there may be two people in the conversation, but that does not mean the conversation started at the same time for both of them.

And sometimes understanding that difference might be what allows the second conversation to be considerably better than the first.