Why “Difficult Conversations” Need a Rethink, and Why Readiness Matters More Than Skill

The Moment Before We Speak

You know that moment. The conversation you know you should have, yet somehow never do.

It sits in the back of your mind, occasionally surfacing at 3am or during your morning commute. You replay it in your head, imagining what you might say and how the other person might react. And then, almost without noticing, you push it away again.

Maybe it is with your manager, about a workload that has become unsustainable and is slowly draining your energy. Maybe it is with a colleague, about behaviour that has been bothering you for months but that you have never quite found the words to name. Maybe it is with someone you manage, where they have shared something sensitive and you are unsure how to respond in a way that feels supportive and appropriate. Or maybe it is a moment when you need to disclose something personal yourself, knowing it could change how you are seen or how the relationship works.

Your heart rate rises. You feel the familiar churn in your stomach. You rehearse the words in your head. Then the “what ifs” arrive.

What if I make it worse? What if they take it the wrong way? What if it changes our relationship forever?

So you put it off. You tell yourself the timing is not right. You convince yourself it might not be such a big deal after all. And in the space where the conversation should have been, silence grows.

The Problem With How We Think About “Difficult Conversations”

When most people hear the phrase “difficult conversation” they picture a narrow set of scenarios. A performance review that contains bad news. Delivering negative feedback about someone’s behaviour. Informing someone they did not get the promotion they wanted. Breaking news about a restructure or redundancy.

These moments are important and often emotionally charged. But they are only a fraction of the situations people actually find difficult.

In my research, I heard story after story about conversations that were nowhere to be found in standard communication training. Many of these situations carried greater emotional and relational risk than the traditional set-piece moments leaders prepare for.

People talked about trying to tell a manager they were at breaking point, only to back out at the last minute. They described sitting in meetings listening to jokes or comments that were exclusionary or undermining, but deciding to say nothing to avoid awkwardness or backlash. They recalled moments where they wanted to share a mental health diagnosis or a family crisis but worried about being judged or treated differently. Some described spotting processes that were unsafe or ethically questionable but hesitating to speak because of fear they would be labelled as difficult or disloyal. Others shared the discomfort of being on the receiving end of a deeply personal disclosure and not knowing whether to respond with empathy, practical support, or silence.

These are not the highly choreographed conversations that come with a checklist and a script. They are often unscheduled, raw, and mutual, meaning that both people in the room are exposed in some way. They carry uncertainty about the reaction and uncertainty about the consequences. They test values, trust, and the core of working relationships.

When our definition of “difficult conversation” stays stuck in the traditional frame, we miss the reality of the moments people avoid most. We overlook the situations that shape trust, inclusion, and psychological safety on a daily basis. These quieter, less visible moments often have the biggest cumulative impact on relationships and culture.

If we do not broaden our lens, we also miss the opportunity to give people the kind of preparation and support that actually makes them willing and able to engage. Instead, we continue to equip them for set-piece conversations that may happen once or twice a year while leaving them unprepared for the unplanned, personal, or politically sensitive conversations that arise every week.

What we need is a more complete picture of difficulty, one that recognises the role of relational risk, personal vulnerability, and organisational climate in shaping whether a conversation feels possible. We need development approaches that do more than hand people a script. We need to help them:

• Recognise early when a conversation is needed, even if it feels inconvenient or uncomfortable.

• Understand how their own emotions, biases, and fears might influence what they say or avoid saying.

• Develop strategies for creating the right conditions, including timing, privacy, and shared purpose.

• Build resilience for moments when the other person reacts defensively, becomes upset, or refuses to engage.

• Work within their organisational reality, while also challenging cultural norms that discourage openness.

This is not about replacing communication skills training, but about reframing it so readiness is built in from the start. It is about moving from “here’s what to say” to “here’s how to get yourself, the other person, and the context to a place where the conversation can happen productively.” Without that shift, our interventions will keep addressing the symptom, awkwardness, while leaving the root cause, unreadiness, untouched.

Why We Avoid

Across my studies, a pattern emerged that went beyond simple discomfort. People often knew how to structure a conversation. They had learned models and frameworks. They had practised active listening and non-judgmental language in workshops. On paper, they had the skills.

Yet when the moment came, they held back.

Avoidance was rarely about an inability to speak well. It was about not feeling ready to speak at all.

Readiness was undermined in several ways. For some, it was emotional. They did not feel steady enough to hold the conversation without becoming overwhelmed or defensive. For others, it was relational. They were not sure the other person would listen without shutting them down or retaliating. And for many, it was cultural. The environment around them signalled that speaking up was risky and that those who did might face subtle or overt consequences.

These gaps in readiness are why so much workplace advice falls flat. It focuses on the words to use and the structure to follow without addressing the more fundamental question: what needs to be in place before the conversation can even happen?

What we need is a shift in focus from perfecting delivery to cultivating the conditions that make speaking up possible. This means recognising that before any model or framework can work, people need emotional regulation, trust in the relationship, and confidence in the organisational environment. Without these foundations, the best techniques remain theoretical, sitting unused while avoidance continues.

Readiness, More Than Just Confidence

Readiness is often mistaken for confidence, but they are not the same. Confidence is a feeling. It can be situational, fleeting, and even misplaced. It can rise in the moments when we are talking about something we know well, and vanish when we face uncertainty or pushback.

Readiness is more grounded. It is less about how we feel in a single moment and more about whether the conditions are in place for us to step forward. It is the point where capability, opportunity, and motivation align in a way that makes action not just possible but likely.

Capability is often assumed to be purely technical, the ability to communicate clearly, structure a message logically, or listen well. These are important, but they represent only part of the picture. In reality, capability also includes psychological clarity. It is about knowing exactly what you want to achieve in the conversation, what outcome would make it worthwhile, and what boundaries you want to maintain. It is also about having enough emotional regulation to stay constructive when the stakes are high, so the conversation does not collapse under the weight of your own reactions.

In my research, I saw capability falter in two main ways. The first was cognitive: people entered a conversation without having fully defined their purpose, so the discussion drifted, became reactive, or turned into a venting session. Without clarity, they struggled to steer the conversation towards a meaningful conclusion. The second was emotional: people anticipated becoming angry, defensive, or tearful and therefore avoided the conversation entirely, fearing they would lose control or undermine their credibility.

This is why capability is not simply a question of “Can I do this?” It is “Can I do this while staying the version of myself I want to be in that moment?” For example, someone might have excellent presentation skills but still avoid telling a colleague that their behaviour is exclusionary, because they fear sounding accusatory or losing their composure. Another might be comfortable giving structured feedback in a formal review but freeze when confronted with a personal disclosure they did not anticipate.

Building capability in this broader sense involves more than learning set phrases or conversation models. It requires practising self-awareness so you can spot your emotional triggers, strengthening your ability to pause before reacting, and rehearsing ways to articulate your point without diluting its intent. It also means learning to recover mid-conversation if you are thrown off balance, so you can return to your purpose without spiralling into defensiveness or retreat.

True capability blends skill with composure and clarity of intent. Without it, even the most motivated person in the most supportive environment can struggle to move from recognising a conversation is needed to actually having it.

Opportunity is sometimes framed as the rarest resource, but in practice it can become the most convenient reason to delay action. People point to timing, privacy, or organisational permission as barriers, and while these factors can be very real, they can also mask deeper readiness issues. It is easier to say, “Now is not the right time,” or “There’s no private space available,” than to admit, “I don’t yet know how to approach this,” or “I’m not sure I want to take the risk.”

In my research, I saw this pattern repeatedly. Participants would identify a missing opportunity, a manager on annual leave, a packed diary, a lack of an empty meeting room, as the reason for not engaging. Yet when those conditions changed, the conversation still did not happen, because the real barrier was capability (not knowing how to navigate the discussion without escalation) or motivation (not believing it was worth the potential fallout).

This is not to say opportunity is unimportant. In cultures where speaking up is punished or where private, focused dialogue is impossible, readiness genuinely suffers. But if we treat opportunity as the only missing piece, we risk letting it become a permanent holding pattern, a safe, socially acceptable reason to avoid addressing the more challenging work of building capability and motivation.

Motivation is the inner driver that tips the balance toward engagement. It is not simply a matter of “Do I care about this?” but “Do I care enough to face the discomfort and risk of raising it?” This is a higher threshold than many people realise. It is possible to care deeply about an issue and still choose not to speak because the perceived personal cost outweighs the expected benefit.

Motivation is shaped by a mix of personal values, past experiences, and expectations about the other person’s response. If speaking up aligns strongly with someone’s identity, for example, a value around fairness, integrity, or inclusion, they may feel compelled to act even when the stakes are high. But if the same person has experienced a punishing or dismissive response in the past, that value-driven impulse can be overridden by self-protection.

In my research, I saw the long shadow of previous conversations. One participant who had been publicly shut down by a senior leader described feeling “trained” not to raise concerns again. Even years later, they could recall the sensation of heat rising in their face and the instinct to retreat. For them, motivation had eroded to the point where avoidance felt automatic.

By contrast, another participant spoke about a moment when they challenged a manager on an unfair policy and were met with curiosity rather than defensiveness. The manager asked thoughtful questions, acknowledged the validity of their perspective, and agreed to review the policy. That single constructive exchange significantly increased the participant’s motivation to speak up in the future, not only with that manager but with others as well.

Motivation can also be dulled when the conversation is seen as unlikely to create change. If someone believes the other person will not listen, or that the organisation will not act, they may decide that risking the relationship or their reputation is not worth it. Over time, this can lead to what some psychologists call “learned helplessness” a belief that effort will not change outcomes, so there is no point trying.

The inverse is also true. Motivation can grow when people experience what I call “micro-successes”, small but positive results from speaking up. These can be as simple as being heard without judgement, having a concern acknowledged, or seeing even a modest improvement in behaviour. Each of these reinforces the belief that it is worth trying again.

For readiness to be strong, motivation needs to be more than a momentary spark. It must be supported by experiences that show speaking up can lead to something better, and by a clear sense that the risk is proportionate to the reward. Without that, the will to engage will wither, no matter how skilled or well-timed the attempt might be.

When capability, opportunity, and motivation are all present, readiness is strong. When any one is missing, the scales tilt toward avoidance. That is why well-meaning advice to “just be confident” so often fails. Confidence without capability can lead to clumsy delivery. Confidence without opportunity can lead to speaking up in the wrong setting. Confidence without motivation can fade at the first sign of resistance.

Readiness is not about a surge of bravery. It is about reaching a stable enough footing, internally and externally, to make the conversation both possible and purposeful.

How to Move from Noticing to Speaking Up: A Six-Stage Approach

In my research, I developed a practical framework called the Six-Stage Behavioural Model for Navigating Difficult Conversations. It is built on a simple idea: difficult conversations are not just single moments of dialogue, they are part of a longer behavioural process shaped by emotions, thoughts, motivation, and the environment you are in.

This process unfolds in six interconnected stages. You might move through them quickly, or you might circle back and forth, especially when the stakes are high.

Stage 1: Awareness – Recognising the Need

It often starts with a feeling. Something is unresolved, unsaid, or unbalanced. You might notice discomfort in yourself, tension in a relationship, or pressure from a situation that is becoming harder to ignore.

At this point, clarity is still forming. You may only know that “something” needs to be addressed. A useful way to pinpoint it is by asking three questions:

• Who is involved?

• What type of issue is it — personal, professional, or both?

• What is the subject — about you, about them, or about the work?

This is the starting signal, even if you don’t yet feel ready to act.

Stage 2: Appraisal – Evaluating the Stakes

Once you have noticed the need, the next step is to weigh it up. How difficult does this feel? What could happen if you speak up, and if you don’t?

Here, the stakes can feel bigger than the conversation itself. You might worry about damaging the relationship, triggering defensiveness, or putting your own role at risk. This is often where motivational ambivalence shows up, part of you knows it matters, but another part fears the cost.

In my work, I use tools like the Conversation Difficulty Continuum and Risk Profiles to help people make this evaluation more tangible. This phase is not about deciding what to say, but about understanding why the conversation feels the way it does.

Stage 3: Behavioural Assessment – Identifying Barriers

With the stakes in mind, it’s time to examine what might help or hinder you. Here I use the COM-B model, which looks at three behavioural conditions:

• Capability — Do you have the skills, clarity, and emotional steadiness to hold the conversation constructively?

• Opportunity — Is the environment supportive? Do you have the time, space, and relational safety to speak openly?

• Motivation — Do you feel it is worth doing, and do you believe there is a chance of a positive outcome?

This stage is where we separate the barriers that can be addressed from those that are harder to shift. It also helps normalise hesitation, reframing it not as weakness, but as the natural result of unmet behavioural needs. When many people in an organisation share the same barriers, especially low motivation, it often points to deeper cultural issues, such as a lack of trust or psychological safety.

Stage 4 & 5: The Action–Avoidance Fork

After you have recognised the stakes in Appraisal and examined your barriers in Behavioural Assessment, you reach a critical junction. Here, there are two possible responses to what you have just learned about the conversation:

Path 1: Moving into Preparation & Support Planning If the outcome of your appraisal leaves you believing the conversation is worth the effort and you see a way forward, you begin to prepare. You draw on the insights you have gathered to decide on timing, structure, and support. Sometimes, this preparation is minimal, a quick mental check before speaking up. More often, especially when the issue is sensitive, it involves deliberate readiness-building: rehearsing key points, seeking coaching, or ensuring the environment will be safe enough to have an open exchange.

Path 2: Jumping straight to Avoidance Not everyone passes through the preparation stage. In some cases, the act of appraising the stakes leads directly to avoidance. This can happen when the perceived risk is so great, or the confidence in a constructive outcome is so low, that further planning feels pointless. Skipping preparation is a clear signal that an intervention may be needed, whether that’s building skills, strengthening emotional regulation, or addressing the environmental barriers that make engagement feel unsafe.

When people move straight from Appraisal to Avoidance, it is often because the conversation has tipped from “difficult” to “impossible” in their mind. Without external support, they are unlikely to revisit it on their own. This is where managers, peers, or organisational systems can make a real difference by offering safe space, reframing the stakes, or tackling structural issues that keep avoidance in place.

Why the fork matters Whether you move into preparation or avoidance, the choice is informative. Proceeding into preparation means readiness is at least partially in place. Jumping straight to avoidance is feedback that something in the earlier stages, capability, opportunity, or motivation, remains unresolved. The model treats both outcomes as valid, but one clearly needs a proactive follow-up.

Stage 6: Reflection & Integration – Learning from Experience

The final stage is about making sense of what happened. Whether you spoke up or stepped back, there is value in pausing to reflect.

What did you notice about your reactions? What supported you, and what got in the way? What would you do differently next time?

This can be done through journaling, coaching, debriefs with a trusted peer, or structured team reflection. The aim is to turn experience into learning, so that each cycle through the model strengthens your future readiness.

When organisations embed reflection into their culture, not just for big projects, but for how people communicate, it reinforces psychological safety and normalises continuous improvement. Over time, conversations that once felt impossible start to feel like part of how the organisation works.

This is the Six-Stage Behavioural Model in action: not a script for what to say, but a map for how to get to the point where you can say it. It recognises that readiness is not a given, and that both action and avoidance can be valuable steps if they are followed by reflection and learning.

Redefining “Difficult”

One of the clearest insights from my research is that difficulty is not built into a topic, it lives in the interaction between the topic, the people involved, and the environment in which it happens.

The same subject can be easy in one setting and almost impossible in another. Offering constructive feedback to a trusted peer in a psychologically safe team might feel entirely manageable. Offering the same feedback to your manager in a culture where upward challenge is rare, or even discouraged, can feel loaded with risk.

What feels difficult for one person may feel relatively straightforward for another. It depends on the perceived risks and all the other factors already mentioned, trust, history, power, organisational culture, and the personal stakes involved.

This is why we need to stop speaking about “difficult conversations” as if they are a single category of interaction. There is no universal list of “the hard ones.” For some, performance reviews are no big deal but disclosing a personal health issue feels impossible. For others, addressing inappropriate behaviour in a meeting might be easy if it comes from a peer, but overwhelming if it comes from a senior leader. The label “difficult” is not about the conversation type, it’s about how it feels for this person, in this relationship, in this moment.

The level of difficulty is shaped by multiple variables:

• Relational dynamics — the history between you, the level of trust, and the power balance.

• Perceived risks — what you believe could happen to your reputation, career, or relationships if the conversation goes badly.

• Organisational culture — the spoken and unspoken rules about what can be said, to whom, and in what way.

When we generalise, treating all conversations on a given topic as equally difficult, we risk offering one-size-fits-all advice that misses the point entirely. A workshop on “how to have performance conversations” might teach a set of useful skills, but if someone’s personal difficulty lies in confronting exclusionary comments in a senior leadership meeting, those skills may not transfer without adaptation.

This is why improving how we approach difficult conversations cannot stop at teaching communication techniques. It requires addressing the conditions that make readiness possible in the first place, building trust, strengthening psychological safety, and reducing the risks that stop people from speaking up.

When we stop assuming that “difficult” means the same thing to everyone, we open the door to far more effective interventions. We start meeting people where they are, focusing on their actual barriers rather than the ones we think they should have.

Making Readiness a Shared Responsibility

If we want workplaces where people can speak openly about what matters, readiness cannot be left to individuals alone. While self-awareness and personal skill-building are important, they are not enough if the environment itself makes conversations feel unsafe or futile.

Leaders and organisations have a critical role to play in creating the conditions where readiness can flourish. This means fostering psychological safety so people believe they can speak without fear of embarrassment, career damage, or relational fallout. It means ensuring there is time and space for meaningful dialogue, rather than expecting difficult conversations to happen in hurried moments between meetings or in public settings that undermine confidentiality.

It also means modelling the behaviour they want to see. When leaders share their own experiences, the moments they prepared carefully, felt discomfort, and chose to engage anyway, they make it clear that readiness is not about fearlessness, but about preparation and purpose. These stories normalise the reality that difficult conversations are challenging for everyone, and they show that taking the step matters more than doing it perfectly.

When readiness is supported from the top as well as cultivated at the individual level, conversations that once felt impossible start to shift into the realm of normal workplace practice. Over time, this changes not only how issues are resolved, but how trust is built and maintained across teams.

A Different Kind of Conversation Culture

Imagine a workplace where “difficult” does not automatically mean “to be avoided.” Where readiness is seen as a core part of preparation, as essential as knowing the agenda or having the right data. In this kind of culture, people recognise that a conversation’s difficulty is not fixed, it is shaped by context, relationships, and support, and they work together to address those factors before the conversation even begins.

In such an environment, the conversations that once required courage become routine. Feedback is offered in the moment rather than stored up for annual reviews. Concerns are raised before they grow into crises. Personal disclosures are met with curiosity and compassion, not awkward silence. This is not an unrealistic vision. It is the natural result of shifting how we think about difficulty and focusing on the conditions that make engagement possible.

A healthy conversation culture does not remove all discomfort, some topics will always feel emotionally charged and personally challenging. That is normal, and it is not something to fear. The goal is not to eliminate discomfort, but to recognise it as a natural part of engaging with issues that matter.

In a supportive environment, discomfort becomes a signal to slow down, prepare well, and approach with care and compassion. Instead of triggering avoidance, it prompts people to consider the other person’s perspective, manage their own emotions, and choose language that supports connection rather than conflict.

When people know they can lean into difficult moments without being punished or shamed for speaking up, they start to see discomfort as an invitation to engage thoughtfully, not as a warning to retreat.

Where to Begin

Difficult conversations are never one-sided. They involve the person who initiates, the person who receives, and often the wider culture that sets the tone for how dialogue unfolds. Each plays a part in making readiness possible.

If you are the one initiating Start small. Name the conversation to yourself, even if you are not yet ready to have it. Ask which part of readiness is missing for you right now:

• Is it capability — not knowing how to frame it or keep it constructive?

• Is it opportunity — lacking the right time, space, or environment?

• Is it motivation — knowing it matters but fearing the cost?

Choose one step to strengthen what is missing: rehearse with a trusted colleague, block out uninterrupted time, or remind yourself why the issue matters. Momentum is often more important than complete confidence.

If you are the one being invited into a conversation Your readiness matters too. Pause and centre yourself before responding. Show curiosity and openness, even if the topic feels uncomfortable or unexpected. Ask clarifying questions rather than reacting defensively. Remember that your willingness to listen and stay present can transform the other person’s experience and the outcome of the conversation.

If you are a leader or shaping the culture Create conditions where readiness is not left to chance. Model the behaviour you want to see by sharing your own examples of leaning into uncomfortable conversations with care and compassion. Make time and space for dialogue, and ensure people will not be penalised for speaking honestly. Build systems, such as debrief practices, peer support, and leadership training, that normalise preparation and reflection on both sides of a conversation.

When all three perspectives are supported, the initiator, the listener, and the culture, discomfort is no longer a barrier to engagement. It becomes a shared moment of responsibility and possibility, one that can strengthen trust, clarify understanding, and spark change.

Final Thought

Readiness is not about removing fear. It is about making sure fear is not the deciding factor.

Redefining “difficult” is not about pretending these moments are easy. It is about recognising them for what they can be, opportunities for clarity, connection, and change, if we are prepared to step into them.