The Chartered Management Institute (CMI) defines a difficult conversation as a face to face exchange of information and views between two people. A difficult conversation is one whose primary subject matter is potentially contentious and/or sensitive and may elicit strong, complex emotions that can be hard to predict or control.

While managers usually can predict when a conversation, they need to have is about be difficult and uncomfortable such as addressing a poor performance or serious misconduct, investigating bullying, discussing delicate personal issues.

However, by adopting the right approach, preparing yourself carefully and developing the right skills, mindset and behaviour, you will be able maximise your ability to handle the conversation effectively and steer it to a successful conclusion acceptable to all involved. To help managers deal with difficult conversations in the workplace, CMI has come up with a checklist that can help managers prepare for a difficult conversation beforehand. This checklist is written from the perspective of the manager who is initiating the conversation and provides guidance that can be applied in most contexts. However, it doesn’t attempt to deal with breaking the news of potential redundancy as this is an area that will require a specific checklist on its own.


  1. Determine the purpose of the conversation

To help you to approach a difficult conversation in the most effective manner, you firstly need to consider two key issues:

  • purpose/reason – why you need to have the conversation
  • outcome/resolution – what you hope to achieve.

Whatever the situation, your purpose and the outcome you seek form the basic foundations of the conversation and must be kept in mind before, during and after the exchange. In some cases, the outcome can be non-negotiable – in the context of a disciplinary or grievance procedure for example; in other cases a positive approach will enable you to reach a satisfactory outcome through negotiation and compromise.


  1. Adopt the right approach

Handling contentious issues requires a somewhat different approach from that used in regular everyday conversations. Make it your aim to reach a mutual understanding through a mature, collaborative exchange of views and ideas. You may well find that such encounters require you to move out of your comfort zone by speaking in a more assertive or challenging manner than you usually do. Be prepared to question your own views, assumptions, and feelings as this will help you to reach a satisfactory solution. It isn’t about winning the argument or using your authority to browbeat another person into compliance; it’s about finding a win-win solution, or at the very least, an amicable agreement. Where relevant, check internal organisational policies on matters such as discipline, grievances and bullying, and use these as a guide.


  1. Recognise and manage your emotional state

By their very nature, difficult conversations are stressful for both parties, and often elicit highly complex emotions. It can be difficult to keep an objective view of the situation, but in an emotionally charged atmosphere, setting an example of calm assertiveness will help to temper the reactions of the other party. Self-awareness and self-control are the watch words here. By managing your own emotions, you are effectively encouraging the other person to do the same. In difficult situations, there are three sets of emotions which you need to be aware of and manage:

  1. how you feel about instigating the discussion

It’s natural to feel apprehensive even embarrassed about starting a difficult conversation and nervous or fearful about how the other person may respond. It can be helpful to bear in mind that the conversation isn’t personal – it’s part of your responsibility as a manager. Outbursts of emotion are not necessarily aimed at you personally; the comments may be directed at you as a representative of the organisation or it may be that this is the first opportunity the person has had to express their feelings. In most cases you will not be personally responsible for what has led to the exchange or for how the person feels.

  1. b) how you feel about the issue being discussed

You should not allow the strength of your own feelings on an issue to cloud your professional judgement. If the matter concerns a personal bugbear of your own, such as laziness or lateness, don’t allow your feelings to affect how you deal with it. Conversely, if the issue is something you don’t feel strongly about yourself, don’t approach it in a casual matter or suggest that it’s no big deal. Your approach needs to be fair and consistent, not based upon your own subjective feelings.

  1. c) how you feel about the person involved

This is perhaps the most complex and challenging of the three strands as it is likely to evoke the strongest emotions. If the person is someone you like and respect, you may feel awkward, embarrassed, or even angry that you need to have the conversation with them. You may be tempted to ‘soften the blow’ in order to spare their feelings, or treat them more leniently because of your relationship with them. In the same way, if it is someone you find difficult to get on with or have clashed with in the past, don’t let feelings of dislike, anger or frustration intrude on or distort the conversation and by no means succumb to the temptation to use it as an opportunity for one-upmanship.

Whatever the nature of the issue or your relationship with the person concerned, you need to behave professionally, putting the needs and feelings of others including the individual, the team and the wider organisation before your own needs or preferences. Make an effort to identify your personal biases and don’t allow your prejudices to influence the conversation. Always treat people with respect and fairness and always focus the conversation on the facts.


  1. Challenge you own assumptions and beliefs

Approaching conversations arrogantly, assuming you know everything there is to know about the topic under discussion is a recipe for failure. Don’t pre-judge the situation and go into the meeting having already made up your mind about it. This is likely to provoke antagonism and unwillingness to compromise. It will discourage people from meeting you half way and make it extremely difficult to reach agreement. Take care to distinguish between opinions and facts. Test your own assumptions and be ready for the preconceptions you have already formed to be challenged – your feelings and beliefs may be entirely unfounded. People don’t always see situations in the same light, so try to see the matter from the viewpoint of the other person. Be open to discussion and willing to be enlightened. Be prepared to explore the other person’s viewpoint, feelings and motives through honed questioning skills and techniques.


  1. Plan the exchange

Although it’s impossible to script a difficult conversation fully, it is helpful to plan a basic structure to keep it on track. Think about the elements which need to be included:

  • the purpose of the conversation
  • your view of the issue(s)
  • the other person’s view of the issue(s)
  • sharing of thoughts, feelings and ideas
  • reaching an agreed outcome.

Make sure that you are as well-informed as possible on the topics for discussion. Gather together any relevant reports or information and make a list of the key points you want to make, so that these are not forgotten if the conversation should take a different turn. As well as thinking about what you want to say, consider how you will express it. Your choice of words can make all the difference to the response you receive. To minimise conflict, avoid so-called ‘landmine language’ – words and phrases that are sure to elicit negative responses – for example, phrases such as: ‘That’s just typical of you!’; ‘Calm down!’, ‘You’re being irrational!’, ‘You would say that!’ Don’t make statements which are blaming, accusatory or condemnatory and never employ sarcasm and insults, or pass moral judgement – the aim is to find a positive way forward. Think too about the non-verbal elements of communication such as tone of voice and body language.


  1. Provide an opportunity for preparation

You have prepared yourself for the exchange. You now need to extend the same courtesy to the other party. They may be expecting an issue to be raised or it may come as a complete surprise. Either way, allowing time for preparation will demonstrate respect for their feelings and give them the opportunity to think through their position and gather any relevant supporting evidence. However, if the matter of concern is sensitive, keep the preparation period short to avoid unnecessary worry and anxiety.

Explain the reason for the conversation and give the person concerned a general idea of the issues you wish to discuss but avoid getting into the detail. If they press you for more information, tell them you’ll discuss the matter in detail at the meeting rather than allow yourself to be drawn into an unhelpful exchange at that point in time. Agree a mutually convenient time and place for the conversation.


  1. Open the conversation

It is your responsibility to put your interlocutor as much at ease as possible. To help reduce tension and steady nerves, open the discussion with a simple restatement of its purpose before inviting the other person to respond. Make it clear that they will be given ample time to speak and to express their viewpoint and encourage a collaborative approach right from the start.

Take a positive approach to the situation and emphasise your desire to find a solution. This should encourage the other person to be willing to work with you to reach an agreement on the best way forward rather than feel that they are being blamed or reprimanded.


  1. Present your side of the story

Present your side of the story, explaining what has given rise to concern and stating the facts clearly and concisely as you see them. Highlight any related consequences you have observed or anticipate, should the matter not be resolved. Be upfront and honest. Never hold back information that could be used to trip the person up later. Express how you feel about the situation and make your motives for initiating the discussion transparent. For example, in the case of poor performance:

“I am frustrated because you have repeatedly missed your monthly targets” (emotion)

“Missing targets affects the performance of the whole team and could prevent team members from receiving their annual bonus” (consequence)

“I know you are capable of doing much better and I want to help you realise your full potential” (motivation)

Never allow self-serving motivations to come to the fore. For example:

“I’m upset and angry because your actions are reflecting badly on my managerial skills and adversely affecting my personal performance targets”.

Taking a positive approach as described above will ultimately be to your benefit, as a collaborative approach will help find a win-win solution for everyone.


  1. Listen to their side of the story

Invite the other person to express their own perspective. Don’t assume you know exactly what they are going to say before they’ve even said it. If what they say differs from your assumptions, don’t accuse them of being in some way dishonest. Their viewpoint may well be at odds with yours for a genuine reason. Take time to reflect on what they have said and to assess its implications. They may tell you something of which you had no prior knowledge and which could significantly alter your perspective on the situation. Listen carefully and demonstrate clearly that you are doing so. Adopt an open posture, using body language to convey that you are inviting confidence and are willing to consider their point of view. Refrain from interrupting and allow them to finish what they have to say before responding. The person you are talking with may well feel exposed or vulnerable. Giving them the opportunity to express themselves, in their own words, will help them to feel empowered and gain the confidence to state the facts as they see them.


  1. Handle reactions with care

If you are delivering information which is likely to be unwelcome, be prepared for a spirited reaction to your communication. No one likes to hear bad news, irrespective of its root cause. The person you are talking with may experience a range of emotions: fear, anxiety, guilt, shock, frustration, vulnerability or sadness. Angry outbursts, tears or a stubborn silence are all difficult to deal with and must be handled with the upmost care. When people are upset, the instinct for self-defence kicks in and their reactions are often expressed more strongly than once they have had time to reflect. You may feel that their reactions are extreme, unmerited or irrational, but whatever you feel, must be put aside. Their outburst must be taken seriously. Acknowledge and respond to their feelings rather than react to their behaviour. Never tell someone they are being silly, dramatic, or that they should calm down. Acknowledge the emotions they are experiencing and respond with kindness and empathy. Put yourself in their shoes. What would you need to hear in a similar situation? Outbursts may be short-lived or drawn out. Be patient and allow the person time to recover their composure. They may be embarrassed about their outburst once they have calmed down so reassure them that their feelings are understandable and natural. A difficult conversation can’t be rushed. Give the individual space and time to respond. If they are overly emotional or overwhelmed it may be sensible to call a short ‘time out’ to allow them to recover. If what you say is met with a wall of silence, consider why that may be – anger, shock, fear, for example. Encourage them to respond by starting with a few simple yes/no questions.


  1. Find the middle ground and reach an amicable solution

Once information has been shared and opinions expressed, it is vital to move on to positive steps to address the situation. As far as possible, this stage needs to involve give and take. It’s not a question of either side coercing the other to accept their view of the situation or of either side seeking an easy way out by passively submitting to the demands of the other. It’s about exploring the issues, finding common ground and identifying potential ways forward that work for both parties. Asking open questions will be helpful here. Both sides may need to adjust their previously held assumptions and accept a degree of compromise. Identify shared interests and motivations and use these as a starting point. Share your own ideas and listen to the other party’s suggestions in return. Explore the reasoning and motivation behind all suggested courses of action. Once agreement has been reached, clarify what has been decided, who is responsible for what; and set a workable timescale for agreed actions or changes. Even in cases where the outcome is non-negotiable, it is still important to share thoughts and feelings. Whatever the outcome of the conversation, it’s imperative to offer support to individuals who have received unwelcome news.


Managers should avoid

  • ignoring what the other person has to say
  • disregarding another person’s feelings
  • allowing personal feelings to mar their professional judgement
  • using their position to coerce and manipulate
  • ignoring or belittling another’s response.





To help managers deal with difficult conversations in the workplace, CMI has come up with a mnemonic to help business leaders navigate such meetings with their staff – TALK.

T – Think about framing how you think about the conversation differently. Don’t label it as ‘difficult’. It may be about a tricky subject but, by suggesting solutions or alternatives, you can focus on constructive outcomes

A – Always use clear, simple and neutral language. Refer to specific examples and facts

L – Listen to what the other person is saying and hear their point of view. Show you care about how they see things

K – Keep the focus on the issue, not the person