How to Have Difficult Conversations

One of the most difficult challenges to effective communication in the modern world, especially during any period of enforced lockdown, seems to be having, and in particular, starting a difficult conversation.

Perhaps trying to have a difficult conversation over the phone or via a video conference facility makes it even harder to do. So during the COVID-19 global pandemic, when human interaction was so limited and even impossible, the ‘fear’ of a difficult conversation when there was no physical face-to-face engagement meant that conversations that should have been had or at least started were not.

Below are my top tips on how to have a difficult conversation:


Realising that a difficult conversation is needed does not make it happen. The simple fact is that the problem will only get worse if it is ignored so the earlier a problem is addressed the easier the solution is likely to be. There needs to be the courage to face the demon and get started.

Getting started

Businessman holding clock. Business time management.It is obviously key for a positive outcome that the request for a conversation is inviting rather than threatening. Brief, polite and respectful are three keys to include in the invitation and also factoring in the need for a mutually agreeable day and time and, of course, location. If the meeting is intended to be online then making sure everything is prepared to make sure you are giving every opportunity for a positive outcome and perhaps the most important factor here is time. A difficult conversation will take as long as it takes and it is important that all involved have sufficient time to fully discuss the matter at hand. Trying to ‘crowbar’ a video conference call between two others or at the end of a long day is not creating the safe, constructive and collaborative forum for a positive difficult conversation.

Rehearse, especially the opening

Before going into any difficult conversation, it is always worth rehearsing, especially the first few words, as they will set the scene. If you are aggressive that will result in a defensive response and therefore a negative difficult conversation. To get the best out of the conversation the opening needs to be conciliatory and welcoming and this will help in setting the tone for a positive outcome. Therefore providing adequate time for the call is also an important factor.  After all, a difficult conversation that starts with “We need to make this quick as I’ve got another call in a few minutes” will only promote a negative reaction as that statement clearly signifies that to one person, the difficult conversation is not as important as to what is next. The reaction to such a statement will be negative and potentially unreceptive to whatever is said next and yet a similar statement could still be made but would create a polar opposite reaction “I am expecting another call shortly and apologise for that but I hope that we can make great progress….”.

Saving face (yours and theirs)

‘Face’ is not just a cultural issue; it is an intensely personal one and intertwined with a person’s feeling of self-worth. People need to avoid losing face and this means they can end the difficult conversation with their ‘head held high’ or their reputation or integrity, intact. So, in order for a difficult conversation to be a positive one, there needs to be the acceptance that solutions, which preserve people’s dignity, reputation or integrity, will mean there is no residual resentment or anger and therefore hopefully, no need to repeat the difficult conversation.

Look to the future, not back at the past

Look to the future not the pastYou cannot change the past but that is where a lot of people in disagreement are rooted. You can influence and control the future and there comes a time when looking back at history needs to change to looking ahead towards how this may be resolved for the better. Most people know they have to let go of the past but often they need an excuse to turn and face the future.

Be positive

The best outcome of the conversation is that the people involved feel better informed and that they understand what has driven the need to have this difficult conversation. By being negative or pointing out the mistakes or failings of others is a focus on the negative and could lead to the worst outcome; the conversation backfiring!

The Dispute Avoidance and Resolution Partnership’s guide “Volcano Insurance – the proactive approach to avoid, manage and resolve disputes”, published by Urbane Publications (May 2020), sets out clearly and concisely the benefits of effective communication and how to have difficult conversations.

Volcano Insurance book cover