Why are difficult conversations put off, and how do you prepare? A practical step-by-step guide for managers on performance, behaviour and personal issues.
Almost every manager has a conversation in their diary that has been put off for months: the one that needs to happen with the foreman who is always late, with the experienced specialist who creates tension in the team, or with an employee who has withdrawn noticeably in recent weeks. Difficult conversations do not shrink as they are postponed; on the contrary, the problem grows, the team senses unfairness, and in the end the conversation takes place at a much more charged moment, in anger. In this guide, for business owners, production managers, team leaders and HR professionals, I look at why difficult conversations are so hard, how to prepare, which steps help during the conversation and how your organisation can spread this skill.
What Are Difficult Conversations, and Why Are They Put Off?
A difficult conversation is any discussion in which the parties are emotionally affected, the outcome is uncertain and there is a sense that the relationship could be damaged. The types most often met in working life are these:
- Performance conversations: Missed targets, quality problems, repeated mistakes.
- Behaviour conversations: Lateness, rude communication, conflict with colleagues, not following rules.
- Conversations about personal circumstances: Signs that an employee is going through an emotional or family difficulty, bereavement, illness, caring responsibilities.
- Bad news conversations: Not getting a promotion, a change of duties, budget cuts, restructuring.
The reasons these conversations are put off usually lie in the manager's own inner world. The worry "What if they're hurt, what if they cry, what if they resign?"; the belief "As a good manager, I should be liked"; having learned to avoid conflict; or the mark left by a conversation that went badly in the past. From a cognitive behavioural perspective, avoidance reduces anxiety in the short term but feeds it in the long term. With every postponement, the conversation grows bigger in the mind. To understand this cycle, the explanation of the avoidance cycle in our article on what cognitive behavioural therapy is may be useful.
The Cost of Unspoken Problems to the Business
Although avoiding difficult conversations may look like an individual discomfort, its consequences are organisational. In the ESENER 2024 survey, which covered 41,458 workplaces in Europe, the biggest difficulty in managing psychosocial risks was reported as "reluctance to openly talk about these issues", at 59% (EU-OSHA, 2025). In other words, knowing about the problem is not enough; being unable to talk about it becomes the first obstacle to a solution.
A similar silence exists on the employee side. In the OSH Pulse survey of more than 27,000 workers in Europe, 50% of employees thought that disclosing a mental health problem would harm their career; only 58% said they would feel comfortable talking to their manager about mental health (EU-OSHA, 2022). Roughly one in two employees believes that speaking openly with their manager will come at a cost.
In Turkey, this picture may be considered even heavier. According to Gallup's 2026 report, 66% of employees in Turkey say they experienced stress and 36% anger for much of the previous day, while the share of genuinely engaged employees is only 8% (Gallup, 2026; 2025 data). In an environment where stress and anger are this high, every unspoken problem can turn into gossip, resentment, quiet withdrawal or a sudden outburst. Performance problems that go unspoken also send the rest of the team the message that "the rules here don't apply to everyone", and they erode the motivation of the best employees.
How Should Managers Prepare for Difficult Conversations?
Half of a good conversation is the preparation done before it. During preparation, answering the following questions makes things easier:
- What is my aim? "To put them in their place" is not an aim. "To understand why deadlines are being missed and to make a joint plan for next month" is an aim.
- What concrete observations do I have? Take notes at the level of date, event and behaviour. Saying "In the last three weeks you arrived 20 minutes late to the start of the shift five times" instead of "You're always late" moves the discussion from interpretation to observation.
- What are my assumptions? Our minds quickly fill in missing information: "They don't care", "They're testing me". Note these assumptions down and turn them into questions in the conversation rather than treating them as confirmed.
- How might the situation look from their side? Keep possibilities in mind such as workload, problems within the team, health, home life and economic pressure.
- What am I feeling? If you are angry or very anxious, it may be better to postpone the conversation briefly and calm down first. But do not stretch "briefly" into months.
Imagine a production supervisor who has noticed that an experienced technician in quality control has been missing defective parts for the last two months. His first reaction may be "He doesn't care about the job any more." By noting this assumption down and setting it aside during preparation, he can go into the conversation with the sentence, "In the last two months, errors have slipped through in three batches; I want to understand the reason for this together." In the conversation, it may emerge that the technician has still not fully learned the interface of the newly purchased measuring device and has told no one because he is embarrassed. In this case, the problem is not a disciplinary matter but a matter of training and open communication. A conversation entered with an assumption, on the other hand, would most likely have ended in defensiveness, resentment and repeated errors. The real function of preparation is to give the manager time to test the story in their own mind against real information.
Practical details matter too. Hold the conversation not in a crowded corridor, at a shift change or at the last minute on a Friday evening, but in a quiet setting where the door can be closed and with enough time set aside. Giving the employee brief notice in advance ("Could we talk for half an hour tomorrow at 3 pm about the deliveries over the last few weeks?") reduces the element of surprise and unnecessary anxiety.
A Step-by-Step Approach During the Conversation
Every conversation is different, but the framework below provides a safe footing for most difficult conversations.
1. Open briefly and clearly. Going round the subject with a long introduction increases anxiety. "I want to talk to you about the lateness over the last three weeks. My aim is to understand what is happening and to find a solution together."
2. Separate observation from judgement. Describe the behaviour, its effect and your own concern separately: "When you arrive late for the start of the shift, the opening of the line is delayed and your colleagues cover for you. This has started to create tension in the team."
3. Ask, and really listen. Being able to stay silent after the question "What's going on from your side?" is the hardest and most valuable moment of the conversation. Listen without interrupting the employee and without becoming defensive. Briefly summarising what you have heard ("So because you have to take your child to school in the mornings, you can't catch the shuttle on time. Have I understood correctly?") makes them feel understood.
4. Make room for emotions, but do not lose the purpose of the conversation. The employee may cry, become angry or fall completely silent. None of this means the conversation has failed. Taking a short break, offering water and saying "I can see this conversation is difficult" is enough. Once the emotion has settled, gently return to the subject.
5. Produce the solution together. The question "What do you think could be done to put this right?" makes the employee a partner in the process. State your own expectations openly too; make clear where you can show flexibility and where you cannot.
6. Set a concrete plan and a follow-up date. Who will do what, and by when? Planning a short follow-up conversation two weeks later prevents the discussion from being left in the air. Keeping a short written summary of important conversations is useful both for transparency and for preventing misunderstandings that may arise later.
The success of a difficult conversation is measured not by nobody being upset at that moment, but by the relationship and the work resting on clearer ground afterwards.
The Manager's Role When Emotional Distress Is Noticed
Some difficult conversations are not about performance but about the employee's wellbeing. When changes are noticed such as insomnia, marked tiredness, sudden irritability, absent-mindedness, frequent sick leave or social withdrawal, the manager's task is not to diagnose but to notice, ask and signpost. A non-judgemental sentence such as "I've noticed you seem tired lately. Is everything all right? If you'd like to talk, I'm here" is often enough to open the door.
The following points need attention here:
- Keep what the employee tells you confidential, and share it only with their permission and only as far as necessary.
- Avoid dismissive phrases such as "Everyone has problems" and "Don't dwell on it".
- If your organisation has an employee assistance programme (EAP), an occupational physician or psychological counselling, remind them of it with concrete details. You can find detailed information on this in our article on the employee assistance programme.
- If the employee talks about thoughts of harming themselves or ending their life, do not leave them alone; direct them to professional support, and in emergencies call 112 (Turkey's emergency services).
These skills are not innate; they are learned. In the World Health Organization's guidelines on mental health at work, the recommendation with the strongest evidence is mental health training for managers (strong recommendation, moderate-certainty evidence) (WHO, 2022). In a randomised controlled study in a fire service in Australia, after managers received four hours of mental health training, work-related sick leave in the teams of the trained managers was found to have fallen by 18% compared with the baseline (Milligan-Saville et al., 2017). It should also be noted that the study was carried out in a single organisation and needs to be replicated; even so, it is an important indication that the way a manager talks is reflected in team health.
Common Mistakes and the Role of Organisational Culture
The traps managers most often fall into in difficult conversations are these:
- The sandwich method: Squeezing criticism between two pieces of praise often causes the real message to be lost. Being clear and respectful is better.
- Trying to solve an individual problem with a mass message: Announcing one person's lateness problem to the whole team by email as a "reminder to everyone" punishes the employees who have no problem.
- Targeting the personality: Statements such as "You're lazy anyway" trigger defensiveness and make change harder.
- Having a difficult conversation by message or WhatsApp: Without tone of voice and body language, the risk of misunderstanding is very high.
- Not following up after the conversation: If a plan is made and not followed up, the employee concludes that the conversation was not taken seriously.
The skill of individual managers is important, but organisational culture determines how far that skill can be used. In the classic study of 51 work teams in a manufacturing company, team members' shared belief that "the team is safe for interpersonal risk taking", that is, psychological safety, was found to be related to the team's learning behaviour (Edmondson, 1999). In an environment where mistakes, concerns and differing views are not punished, difficult conversations are held earlier and more calmly. I cover this subject in more detail in our article on psychological safety.
How Do You Get Started in Your Organisation?
Instead of leaving difficult conversations to the courage of individual managers, it is possible for the organisation to build a systematic approach. A three-stage roadmap can be suggested:
Needs analysis: Identify which types of conversations managers find hardest, through a short survey and focus group discussions. Add items such as "I can comfortably discuss a problem with my manager" to employee surveys. Complaint records, exit interviews and absence data can show where unspoken problems are accumulating.
Programme: Plan face-to-face workshops for managers that use role plays and real scenarios. Instead of a one-off seminar, offer reinforcement sessions a few weeks apart and one-to-one support they can turn to in a difficult case. A workplace psychologist or external consultant can provide supervision support to managers, especially in conversations that involve emotional distress. You can see such training and consultancy models on the corporate services page.
Measurement: Before the training and at regular intervals afterwards, monitor managers' confidence levels, the communication items in employee surveys, and complaint and conflict records. The International Labour Organization also recommends absence, turnover, complaint reports and employee surveys as monitoring indicators (ILO, 2026).
Frequently Asked Questions
Should an HR professional attend difficult conversations too?
Everyday performance and behaviour conversations should mostly take place between the manager and the employee; the presence of a third person can make the conversation more formal and threatening than necessary. In disciplinary procedures, serious complaints or situations that may have legal consequences, however, it is appropriate for HR to be involved and, where necessary, to consult an employment law specialist.
What should I do if the employee cries during the conversation?
Without panicking, take a short break, offer a tissue and water, and say that their feeling is understandable. You do not have to end the conversation immediately; you can return to the subject when the employee is ready. If the reaction is very intense, postponing the conversation to another day is also an option.
Difficult conversations make me very anxious as a manager. Is this normal?
Yes, it is quite common. Preparing, rehearsing the conversation and gaining experience by starting with smaller conversations reduce anxiety over time. If the anxiety clearly affects your sleep, your work and your private life, getting support from a professional can also be helpful.
How do you have a difficult conversation with a remote team?
Prefer a video call where possible and avoid holding a difficult conversation by written message. Give notice of the time in advance, and choose a slot when cameras are on and there will be no interruptions. Sharing the agreed steps in a short written summary after the conversation reduces misunderstandings in remote working.
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Eda Erkan Alapala
Klinik Psikolog. İstanbul Kent Üniversitesi Klinik Psikoloji Tezli Yüksek Lisans mezunu; bilişsel davranışçı terapi, çocuk merkezli oyun terapisi ve çocuk-ergen psikoterapisi alanlarında eğitimlerini tamamlamıştır.
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