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Having Difficult Conversations

By Deacon Michael Ross, Service Chaplain


Having difficult conversations is a necessary part of adult life. It is also that part of adult life that we are likely to put off where possible, or avoid altogether. Sometimes, we may fear that talking about a difficult issue may only make matters worse or we might have tried to broach a difficult conversation and may feel that we have failed in the process. Either way, we may find ourselves stuck and this often leads to a difficult situation remaining unresolved and, worse, leads to a lot of wasted energy. There are dozens of books and articles dealing with difficult conversations (some of what is written here is based on work by judyringer.com) but what I want to do here is to provide some basic thoughts and suggestions, perhaps even a breakdown of best practice strategies for getting on with that experience most of us will do anything to get out of.

Before I begin, however, I want to stress that it is important to remember that best practice strategies or ‘technique’ will only ever take you so far. We all know that feeling of being ‘managed’, of being tolerated, perhaps, in a discussion but not being really engaged. It’s like being ‘half listened’ to! The most important aspect of handling a difficult conversation is to genuinely enter into the process with a positive sense of seeking a resolution. Anything else will read as insincere and is unlikely to move things forward at all.

Before taking any kind of action, it is important to think about that action. When thinking about difficult conversations and prior to tackling one, a useful starting point might be useful to ask yourself some challenging questions:

  • What is the purpose of the difficult conversation? What is the outcome you are hoping for? Is there any hidden sub-text? Sometimes we delude ourselves into believing that our intentions in having a difficult conversation are entirely honourable. A little reflection might indicate that what we consider supportive is actually punishing and harshly unhelpful. It might be useful to consider how you can enter into the conversation in the most supportive way possible.

  • Are you making unhelpful assumptions about the behaviour of the person to whom you plan to have the conversation? While the impact of their behaviour may appear belittling or disrespectful, was this actually the intent of their behaviour?

  • Are your ‘buttons being pushed’? Is the person you plan to tackle about an issue triggering something in you, or about something of your past? It may be that some of the emotional ‘heat’ you are experiencing in a given situation is more about you than the person you perceive to be problematic. Again, a little reflection on the issue might be useful in balancing whatever it is you plan to say.

  • What is your underlying attitude to the conversation you are planning and is that attitude influencing your perception of the conversation? We often reap ‘what we sow’: if you believe that the conversation will be extremely demanding and unlikely to be of any positive value, in fact, that the conversation might be a waste of time, that is fairly likely to be the case. Adjusting your attitude might allow you to reframe the challenge to consider more positive outcomes.

  • Think about the person you plan to confront. Are they aware of the problem you perceive? What solutions might they suggest? Trying to get on to the same side of the table, with both of you looking at the issue together, instead of facing each other in opposition, might make the whole experience more manageable.

  • Probably the most difficult question to think about is what your own role might have been/continues to be in the on-going conflict. Is there some way in which you might be inadvertently making things worse? Thinking about your own contribution to the problem might provide you with some helpful ideas in resolving it.

Moving Toward a Successful Outcome

There are some fundamental skills that can be invaluable in reaching a positive outcome in a difficult conversation, but underlying these techniques is the crucial importance for you in remaining responsible for yourself and your own emotional energy. The best way to achieve that goal is to remain centred and calm. By breathing easily and deeply, you are more likely to remain centred and, in doing so, you are also more likely to encourage the same behaviour in the other person with whom you are engaged. Notice when you go ‘off-centre’ and ensure that you return to centre again as soon as possible.

That said, here are some possible steps to success in difficult conversations.

  • Step One: In as far as you can, try to develop a sense of enquiry and curiosity in the situation. Let the other person talk without interrupting and try to learn as much as possible about them and how about how they view the circumstances under discussion. There will be ample opportunity for you to state your understanding of things and there is no need to rush.

  • Step Two: Make every effort to ensure that the other person feels acknowledged and understood. Listen carefully and repeat back what the other person says as often as necessary to indicate that you are listening, hearing and, importantly, understanding their point of view. What you want to try and do is to honour the other person’s position. That doesn’t mean you are in agreement with everything being said, but it does mean that you are respecting the other person’s perspective.

  • Step Three: Once the other person has finished saying everything they have to say, it’s your turn to put your position forward. It’s important to clarify your ‘take’ on the situation without minimising the perspective of the other person. You might use this opportunity to add to some of what the other person has said, considering parts of the situation that he/she might have missed.

  • Step Four: Once all the information is on the table, it’s time to begin problem-solving. What is the solution to the issue you are both facing? Ask the other person what their potential solutions are and find something useful in their suggestions to build on. Genuinely asking the other person for their solutions can go a long way toward establishing a feeling of safety for both of you and a renewed sense of engagement.

Practice and Skills Building


Like any other skill, holding difficult conversations takes practice, and, in order to practice the skills involved in difficult conversations, it is crucial that you stop avoiding having these conversations. Attempting to openly seek to resolve thorny issues in a calm and confident manner can have excellent effects on team morale. By taking things out into the open, the likelihood of further dispute reduces.

There are some other suggestions that might prove useful:

  • The successful outcome to a difficult conversation depends on what you say and how you say it. By being centred, supportive, enquiring and solution focused you increase the possibility of a positive outcome.

  • If the conversation becomes heated, be prepared to re-centre and redirect that emotional energy to a more beneficial purpose. Try to avoid personalising things that are said and don’t automatically assume that the other person will always see things clearly from your perspective.

  • In preparation for a difficult conversation, it might be useful to mentally prepare and to visualise the conversation before entering into it. It might also be useful to practice the conversation with a colleague or friend.

Finally, difficult conversations are generally unavoidable. We will all be required to enter into this arena at some point. Acquiring some skills in this area is essential to achieving an outcome that is positive and meaningful and like any other skill, practice is essential. Good luck!

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