Turning Difficult Conversations Upside Down

Say the words “difficult conversation” in a workplace context and most people will picture the same scenario. A manager calls an employee into their office. There’s a formal agenda: performance review, behavioural feedback, perhaps a conflict that needs resolving. The conversation feels heavy, awkward, but necessary.

This image is so dominant that it has come to define what “difficult conversations” (DCs) mean in organisational life. HR manuals, leadership training, and countless Harvard Business Review articles reinforce this view. The subtext is clear: difficult conversations are top-down managerial tools. The challenge lies in equipping managers with the right frameworks and communication skills to handle them well.

But what if this framing is only half the story?

Through my research into how employees experience and navigate difficult conversations at work, I discovered that the hardest conversations are not always these formal, manager-led encounters. The most difficult, the ones employees most often avoid or agonise over, are different. They are bottom-up. They are personal. And they are far less visible in organisational discourse.

It’s time we turned difficult conversations upside down.

The Traditional Framing of Difficult Conversations

Mainstream thinking on DCs is shaped by a fairly narrow set of assumptions:

• They are manager-led. The manager initiates, frames, and directs the exchange.

• They are about performance or conflict. The topics are work-related, measurable, often formalised.

• They are skill-based. The challenge is one of technique: how to structure the conversation, control emotions, deliver feedback.

This framing shows up clearly in the acronyms and models commonly taught in management, HR, and even healthcare training. They are designed to give structure and reduce anxiety for the speaker, the person delivering the “difficult message”, but they almost always position the other person as a recipient rather than a co-participant.

Take the SPIKES framework, originally developed in healthcare for breaking bad news to patients:

• S – Setting up the interview

• P – Assessing the patient’s Perception

• I – Obtaining the patient’s Invitation

• K – Giving Knowledge and information

• E – Addressing Emotions with empathic responses

• S – Summarising and strategising

While SPIKES has been widely praised for giving clinicians confidence in emotionally charged situations, it is still fundamentally a delivery model. The professional has the knowledge; the patient is guided through receiving it.

Corporate training has borrowed this logic. Models like BEERS (Behaviour, Effect, Expectation, Result, Support) or DESC (Describe, Express, Specify, Consequences) provide neat scripts to “manage” a conversation. They tell managers how to state the issue, outline the impact, propose changes, and make clear what will happen if behaviour doesn’t shift.

These frameworks do serve a purpose. They help managers avoid vagueness, anchor feedback in observable facts, and offer support alongside accountability. But the underlying assumption is the same as in SPIKES: that a difficult conversation is a structured message from one party (the one in power) to another (the one with less).

The implicit goals are:

• Clarity of delivery – ensuring the message is understood.

• Minimising fallout – reducing defensiveness, emotion, or escalation.

• Maintaining authority – positioning the manager as the decision-maker.

What gets lost in this framing is reciprocity. The idea that the other person may have their own difficult truth to share. That the real difficulty may lie not in delivering a message but in disclosing one. That “difficult” conversations are often most difficult when the person with less power is the one doing the speaking.

In other words: these models prepare managers for one-way traffic. But the hardest conversations in workplaces are usually two-way, relational, and deeply human.

This approach has value, there are times when leaders must have structured, challenging conversations about behaviour or performance. But as a universal framing, it is deeply incomplete.

It overlooks the conversations that employees themselves find most difficult. It assumes difficulty is a deficit of skill, rather than a reflection of relational risk. And it ignores the fact that many of the most emotionally charged conversations in organisations are not about tasks or performance at all, they are about people.

The Reality — Bottom-Up and Personal

In my research, participants consistently rated conversations as more difficult when:

• They were with managers (rather than peers or direct reports).

• They were about personal matters (rather than task-related issues).

• They were about themselves (rather than about others).

This finding flips the dominant script. It suggests that what employees dread most is not being called into a performance meeting, but approaching their manager to disclose something personal or identity-related.

These are the conversations where employees feel exposed:

• Asking for adjustments because of a health condition.

• Disclosing a mental health struggle.

• Naming an experience of exclusion, bias, or harassment.

• Raising concerns about workload or burnout.

• Coming out or sharing an aspect of identity – telling a manager about being LGBTQ+, neurodivergent, or part of a faith group not widely recognised in the organisation.

• Expressing disagreement with leadership decisions – challenging a policy, restructure, or change initiative that feels harmful.

• Reporting bullying or toxic team dynamics – risking being labelled a “troublemaker” for speaking up.

• Disclosing financial hardship – asking for salary advances, support funds, or explaining the need for additional work flexibility.

These moments are difficult because they invert the usual balance of power. The employee, often with less formal authority, must take the risk of disclosure. The manager, with greater power, controls how that disclosure is received, judged, or acted upon.

All of these share the same DNA: they require the employee to step into vulnerability, often against cultural or structural barriers, with no guarantee of how their honesty will be received.

For the employee, the stakes are rarely just professional. They are relational and identity-based. “If I say this, will I still be seen as competent? Will my role or progression be affected? Will my manager still respect me? Will I even be safe here?”

It is not hard to see why silence can feel safer than speech.

Why These Conversations Feel Harder

So why do these employee-initiated, personal conversations feel so much more difficult?

From the themes in my interviews, several interlocking factors emerged:

1. Power Dynamics

The asymmetry of power in the workplace makes disclosure fraught. When an employee speaks “upwards,” they are not just sharing information, they are stepping into a space where their words could be judged, scrutinised, or even weaponised against them. Employees often worry that being open might label them as “difficult,” “needy,” or “not resilient enough.” The potential for career repercussions, missed opportunities, stalled progression, or subtle shifts in how they are perceived, magnifies the risk. In short, power makes vulnerability costlier.

2. Emotional Risk

Unlike a task-based discussion, personal disclosures require revealing something deeply tied to identity, health, values, or lived experience. For many employees, this is not just about explaining a situation but exposing a part of themselves that feels fragile. The emotional labour begins long before the conversation itself: rehearsing what to say, worrying about how it will be heard, and bracing for possible rejection. By the time the words are spoken, the employee may already be emotionally exhausted.

3. Relational Factors

The quality of the relationship with the other person profoundly shapes the risk. An employee who trusts their manager may still feel anxious, but trust provides a foundation of safety that makes disclosure possible. Where relationships are formal, transactional, or marked by past breaches of trust, avoidance dominates. Participants in my study often described “testing the waters”, dropping hints, gauging tone, or observing their manager’s reactions to others, before deciding whether to risk disclosure. In this sense, the conversation is as much about the relationship as it is about the topic.

4. Organisational Signals

The wider culture of the organisation matters enormously. In workplaces where silence, compliance, or performance are prized, the perceived cost of speaking up is higher. Employees quickly learn which topics are “safe” and which are taboo. A culture that rewards visible resilience but quietly penalises vulnerability sends a clear message: keep personal struggles hidden. Conversely, in organisations where leaders model openness, where wellbeing is prioritised alongside performance, and where mistakes are treated as learning opportunities, employees described feeling more able to speak, even when the topic was difficult. Psychological safety doesn’t remove difficulty, but it shifts the calculation of risk.

5. The Aftermath

Many participants described how the follow-up, or lack of it, mattered as much as the conversation itself. A disclosure that was acknowledged and acted upon could feel empowering, even if the conversation was awkward in the moment. But when employees took the risk of speaking up and were met with silence, inaction, or avoidance by the manager, the impact was doubly damaging. Not only did the issue remain unresolved, but the act of disclosure itself felt like a mistake. This sense of being ignored or dismissed could erode trust, increase disengagement, and make future disclosure far less likely.

Taken together, these factors show that what makes a conversation “difficult” is rarely the words themselves. It is the context, the power dynamics, emotional labour, relational history, cultural climate, and consequences that follow.

From Skill Deficit to Behavioural Dynamics

The traditional approach to difficult conversations is built on the assumption of a skill gap. The logic goes: if we teach managers to listen actively, deliver feedback constructively, regulate their emotions, and follow a clear structure, the “difficulty” will diminish.

There is some truth in this. Communication skills can help managers be clearer, calmer, and more attuned. But my findings suggest that difficulty is not primarily a matter of skill. Instead, it is a function of behavioural dynamics, shaped less by what people know to do, and more by whether they feel able, supported, and motivated to do it.

This is where the COM-B model of behaviour change provides a more powerful lens:

• Capability – an individual’s knowledge, self-efficacy, and emotional regulation. Do I feel confident enough, prepared enough, and steady enough to have this conversation?

• Opportunity – the external conditions that either support or hinder action: privacy, time, organisational culture, power structures, psychological safety. Do I have the space, backing, and safety to speak?

• Motivation – the internal drivers that determine readiness to act: fear, values, anticipated outcomes, personal goals, and emotional state. Do I want to have this conversation, and do I believe it will lead to something constructive?

Seen this way, the barriers to difficult conversations are less about lack of skill and more about calculations of risk. Many employees already know what they want to say, they may have rehearsed the words in their head a dozen times. What holds them back is the fear of repercussions, the absence of trust, or the cynical sense that “nothing will change.”

In this light, avoidance is not cowardice. It is a rational, self-protective behavioural response to risk. When the potential costs of speaking feel greater than the likely benefits, silence becomes the safer, more logical option.

To capture this dynamic, I introduced the concept of the resistance–avoidance loop. It describes the cyclical process employees described:

1. Preparation – they start to ready themselves to speak, often rehearsing what they would say.

2. Anticipation – they imagine the possible reactions: dismissal, judgement, retaliation, awkwardness.

3. Calculation – they weigh up the potential fallout versus the potential gain.

4. Withdrawal – they decide it isn’t worth the risk and retreat into silence.

The loop doesn’t end there. Each time avoidance feels safer than disclosure, the behaviour is reinforced. Over time, the act of speaking up comes to feel harder and harder. The loop becomes self-perpetuating, deepening disengagement, mistrust, and sometimes even resentment.

This is why skill-based training, while useful, is insufficient. You can teach someone the “right words” or a new framework, but if they are caught in the resistance–avoidance loop, the conversation still won’t happen. Breaking the loop requires more than communication tips, it requires changing the conditions of opportunity and motivation so that speaking feels possible, worthwhile, and safe.

In other words, the pathway to better difficult conversations is not “teach people to talk differently.” It is “build workplaces where people feel able, supported, and motivated to talk at all.”

Conversations as Cultural Signals

If we stop seeing difficult conversations as isolated exchanges between two individuals and start treating them as cultural signals, they take on a new significance. They become diagnostic tools that reveal far more about the health of an organisation than a staff survey ever could.

• Every avoided conversation is feedback. When employees hold back from speaking, it is rarely because they have “nothing to say.” More often, it signals a lack of safety, a deficit of trust, or a belief that raising the issue won’t make a difference. Silence, in this sense, is not emptiness, it is information.

• Every disclosure is a moment of courage. For an employee to share something personal, risky, or identity-based, they must believe, even if only tentatively, that they will be heard. These moments show where trust already exists, or where it is being tested in real time.

• Every manager’s response is a cultural inflection point. How a manager responds does more than resolve an individual issue. It communicates, to the individual and often to the wider team, whether the organisation values openness or punishes it.

Seen in this way, difficult conversations act as a barometer for organisational health. They surface the hidden dynamics of inclusion, power, and belonging. They show whether espoused values (like “we care about wellbeing” or “we value diversity”) are lived out in practice, or remain aspirational slogans.

Cultural Signals and Norms

Workplaces are full of signals, subtle cues that tell people what is acceptable, what is risky, and what is off-limits. These signals may never be written down, but they are felt everywhere:

• Who speaks in meetings, and who stays silent. If only senior voices are heard, employees quickly learn that speaking up is not rewarded.

• What stories are celebrated. When resilience and “toughing it out” are praised, vulnerability becomes stigmatised.

• How mistakes are handled. If errors lead to blame and punishment, people avoid surfacing problems. If they lead to learning and support, people feel safer to disclose.

• The language leaders use. Leaders who talk openly about their own struggles or uncertainties model that it is safe to be human. Leaders who speak only of targets, metrics, and performance send a different message.

• Who gets promoted. When those who prioritise people and inclusion rise, others follow suit. When only “results at all costs” is rewarded, silence becomes the rational strategy.

These signals accumulate into cultural norms. Norms are the unwritten rules that govern everyday behaviour. They determine whether people feel free to ask questions, raise concerns, or share personal truths. They explain why two organisations can use the same HR policies but produce entirely different climates of openness.

In cultures where the prevailing norm is silence, employees quickly learn that difficult conversations carry too much risk. Avoidance thrives. By contrast, in cultures where the norm is voice, where openness, curiosity, and respect are modelled and reinforced, the difficulty does not disappear, but the calculation of risk shifts. People still feel anxious, but they also feel supported.

The Research Link

Amy Edmondson’s work on psychological safety shows that teams where people feel safe to speak up, to ask questions, admit mistakes, or raise concerns, consistently perform better. My research echoes this: the perceived difficulty of conversations decreases when cultural signals of safety increase.

In other words, the difference between silence and voice is not about how brave individuals are. It is about the signals they receive and the norms those signals create.

Reframing Difficult Conversations as Opportunities

What happens if we reframe difficult conversations not as threats to be managed, but as opportunities to be heard?

The shift may sound subtle, but it is profound. When difficult conversations are seen as problems, organisations focus on containment: “How do we minimise disruption? How do we stop conflict escalating? How do we control the fallout?” But when they are seen as opportunities, the focus changes: “What is this conversation telling us? What can we learn? How can we grow from it?”

Reframed in this way, difficult conversations become catalysts for growth at three levels:

1. Individual Growth

For employees, initiating a difficult conversation can be an act of agency and courage. Speaking up, whether about health, identity, workload, or values, is not simply sharing information, but reclaiming a voice in the system. Even if the outcome is uncertain, the act itself can be empowering.

For managers, receiving such a conversation is not just a challenge but an invitation. It is an opportunity to practice empathy, humility, and attunement. It requires them to step out of the “problem-solving” mindset and into the role of listener and partner. Many managers in my research reflected that the most transformative moments in their leadership came not from giving polished feedback, but from being trusted with someone’s vulnerability.

2. Relational Growth

At the relational level, difficult conversations recalibrate trust. They are moments of truth where relationships are either fractured further or strengthened. When handled with openness, they can:

• Repair breaks caused by past misunderstandings.

• Reset boundaries where expectations were unclear.

• Deepen authenticity by moving beyond superficial politeness into genuine dialogue.

These moments may still feel awkward, messy, or emotionally charged. But it is precisely that messiness which makes them real. A relationship that survives, or even strengthens, through a difficult conversation carries a deeper resilience.

3. Organisational Growth

At the systemic level, difficult conversations act as a mirror. They expose the gap between what organisations say they value (wellbeing, inclusion, integrity) and what employees actually experience. A disclosure about workload may highlight unsustainable practices. A complaint about bias may reveal structural inequities. A conversation about health may show where policies are failing to meet lived realities.

These moments are opportunities for organisations to:

• Redesign practices and processes that unintentionally silence or disadvantage people.

• Address inequities that remain hidden in day-to-day operations.

• Build cultures of trust where values are not just words on a website but lived commitments.

In this sense, every difficult conversation is an organisational feedback mechanism. Ignoring them means missing opportunities to adapt and evolve.

The Shifts Required

This reframing does not happen automatically. It requires conscious shifts in mindset and practice:

• From top-down feedback → to bottom-up disclosure. Difficult conversations are not just about managers giving direction, but about employees risking honesty.

• From work tasks → to personal wellbeing and identity. The issues that feel hardest are not about deadlines or deliverables but about health, inclusion, and belonging.

• From skills training → to cultural conditions. Teaching people scripts and techniques helps only when the environment is safe enough for honesty. Culture is the soil in which skills either flourish or wither.

• From individual bravery → to collective responsibility. The burden should not fall on individuals to summon extraordinary courage just to speak. It is the organisation’s responsibility to create conditions where ordinary courage is enough.

The Role of Skills in Context

This reframing does not mean that communication skills and frameworks have no place. Skills matter, but their role is often misunderstood.

Without cultural safety, skills are cosmetic. A manager may follow the perfect script, but if the employee does not trust the system, the words ring hollow. Similarly, employees can rehearse their lines endlessly, but if they believe they will be punished for speaking, the conversation will never begin.

With cultural safety, however, skills become amplifiers of trust. A well-timed question, a clear structure, or an empathetic response can take a moment of honesty and transform it into a moment of growth. Skills are the scaffolding, but the foundation is always trust, safety, and cultural norms.

Reframing difficult conversations in this way shifts them from being sources of anxiety to being portals of possibility. They stop being events to fear and start being opportunities to build stronger people, stronger relationships, and stronger organisations.

Turning Difficult Conversations Upside Down

When we “turn difficult conversations upside down,” we challenge the assumptions that have dominated management literature for decades. We stop imagining DCs as primarily about managerial authority, a boss giving feedback, correcting behaviour, or enforcing standards. Instead, we begin to recognise them as moments of mutual vulnerability, where both people stand to risk and gain something real.

The hardest conversations in workplaces are rarely those where a manager delivers tough feedback. Far more often, they are the moments where an employee hesitates, weighing the risks of speaking out. These are the conversations where identity, health, and values collide with organisational power.

This reframing demands a new organisational stance, one that shifts the burden from the individual to the collective:

• Leaders must build environments where employees trust they will be heard rather than punished. This is not a one-off workshop, but a continuous practice of modelling vulnerability, addressing inequity, and acting on what people share.

• Managers must respond with curiosity, empathy, and meaningful action, even when the topic feels uncomfortable, personal, or beyond their immediate expertise. A manager’s role is not to have all the answers but to create a safe container for dialogue.

• Employees must be supported to understand that avoidance is not personal failure. It is a signal about context: if a conversation feels impossible, the conditions are not yet right. Shifting the narrative from “I should be braver” to “we should be safer” relieves the unhealthy burden of individual heroism.

• Organisations must pay attention not only to the conversations that happen, but also to the ones that don’t. The silences, the hesitations, the things employees talk about with each other but never with leadership, these are just as revealing as the conversations that reach HR or senior management.

In short, difficult conversations are less about technique than about truth. They are less about the words we say than the willingness to create conditions where honesty is possible.

Conclusion: The Call to Action

If we want workplaces where people can thrive, we need to fundamentally reframe what we think of as a difficult conversation.

The conversations we avoid say more about our workplaces than the ones we script. The hardest, and most important, conversations are not the polished exchanges managers rehearse in HR training rooms. They are the ones employees hesitate to have: the disclosure of a health condition, the naming of bias, the quiet request for help, the expression of values that don’t align with “how things are done here.”

When we turn difficult conversations upside down, we stop treating them as managerial threats to be controlled and start seeing them as cultural signals to be heard. This shift changes everything:

• From control → to curiosity.

• From threat → to opportunity.

• From silencing difference → to valuing diversity.

• From individual burden → to collective responsibility.

The invitation is clear: stop asking, “How do we teach people to deliver difficult messages?” and start asking, “What needs to be true in our culture for people to speak their truths?”

Because in the end, the health of an organisation is not measured by how smoothly its managers deliver scripted feedback. It is measured by how safely its people can share their truths, and how the organisation responds when they do.

That is the real test of trust, inclusion, and resilience at work.

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