The Art of Difficult Conversations by Paul Kaye




By Paul Kaye

PSR Contributor


Tuesday April 19th, 2016


It’s Good To Talk: The Art Of Difficult Conversations

We’ve all done it at some point. We have it in common. We have all avoided having a difficult conversation with someone. Conflict isn’t something any of us desire. Many of us see conflict in the same way we view a house that’s on fire; the closer we get the more uneasy and terrifying it can be, and it’s best to get as far away from it as we can. But avoiding conflict – and not having that difficult conversation – is one of the major barriers to our success and happiness.

Somehow we convince ourselves that the unhappiness of not having the difficult conversation is lesser than the unhappiness of having it. That’s simply not true. It’s just our mind playing a trick on us and creating a false sense of security. “It’s best not to poke the bear! There’s less danger by leaving things alone!” our minds tell us. Therefore, we chose to avoid, deny or rationalize the problem or behavior instead of tackling it.

It is fear that prevents us from having these difficult conversations. We dread the outcome of the conversation. We get anxious about what the repercussions could be. We are terrified about what the other person may do. We worry about the unknown that may confront us as we enter into a difficult dialogue. However, when we decide not to shy away from difficult conversation at work and instead face them head on, our confidence, self-awareness and sense of control all increase, all of which contribute to our overall sense of worth and happiness. Having difficult conversations will actually in the long run make us happier!

When you do find yourself being brave enough to deal with the inevitable sweaty palms and tackle a difficult conversation, there are some things you must remember:

Approach the conversation from a place of positivity. If you bring negativity to any activity or conversation you will only see the bad in the situation. You will be expecting the worst and therefore your defenses will be up and you will only be on the lookout for any behavior that may constitute a threat. This state of high alert will make you oblivious to anything other than the unfavorable. If you bring negative energy to a difficult conversation you will be setting the tone for the entire dialogue. Instead think positivity. Consider the outcome that you want and in particular how you want the other person to feel at the end of the conversation. Committing yourself to an emotional intention at the outset will give you the best chance at a successful conversation.

Don’t mirror their reaction. No one likes to be on the receiving end of bad news. We’ve all been there and it is thoroughly unpleasant. Spend time thinking about the likely emotions you will be met with by the other person. Will they be upset? Will they be angry? It’s important that you are prepared for what reactions you may be met with. In the heat of the moment it is easy to mirror the reaction that is extended to you. They get mad, you get a little mad and things start escalating. Be mindful of what you may have to deal with so you can be prepared to stay calm and centered.

Take your time. Don’t rush to get it over with. For many people a difficult conversation is like ripping a band aid off. You know it’s going to hurt. The sticky glue is going to pull at the skin and the hair underneath it. With every gentle tug it’s going to hurt a little more. The best option is to grit your teeth and pull it off as quickly as you can. This approach is dangerous. You will speed through the conversation saying all that you wanted to say delivering each word with purpose. Then when your well-rehearsed monologue comes to a conclusion you can take a sigh of relief and move on. The problem is you haven’t engaged with the other person. You haven’t had the chance to explore whether the message you wanted to convey has been received and understood. You need to take your time and allow space for the other person to respond, seek clarity and ask questions. After all, it is a conversation, and not a monologue, you want to have.

Being prepared but not scripted. We feel comfortable when we have control of a situation, so when we are preparing for a difficult conversation it can be all too easy to script out exactly what you want to say. You want to make sure that every word you utter is the best word you can use. The problem is that a script actually undermines your control of the situation. The other person doesn’t know ‘their lines’ and therefore the conversation will feel stilted and artificial. A better approach is to scribble down a few notes and key points before your conversation. Know what you want to communicate but be flexible to the flow of the conversation.

Watch your language. Keep your language simple. You want to be clear, direct and neutral. Resist the temptation to talk in circles. Don’t try and be clever. Emotions run high when confusion sets in. People need to know exactly what you are saying, how you feel and what you are hoping to achieve with this conversation. Also, be careful to not be judgmental; you are not attacking the person but rather highlighting their actions or behavior and how it has impacted you.

Acknowledge their perspective. Too often we think how we see the world is the only way to see the world. How we experienced something must be the way everyone else experienced it. However, that’s simply not true. We all see things and experience things slightly differently. Our past, along with our beliefs and values, shapes how we interpret our experiences. It would be naïve to approach a conversation assuming that there is only one perspective on the situation. Yours! It’s important that in any conversation you acknowledge that you don’t know the other person’s viewpoint and that you do want to take some time to understand it. There is never a downside to showing others you care about what they think and feel. It is only by inquiring about how they see things that you may find a solution that you hadn’t previously considered.

And finally, be compassionate! You should approach any difficult conversation from a position of empathy. You need to be considerate. What you have to say may be unpleasant so it’s important you deliver it in an honest and fair way. Also remember, when you initiate a difficult conversation you should make sure you don’t make the conversation about you and never play the victim; “This is really hard for me…” or “I feel bad about this…” This is a trap that will never serve you well.

Having difficult conversations is something we shouldn’t run away from screaming in terror. Avoiding these conversations will only lead to greater stress. The pressure will build inside you like a vigorously shaken bottle of pop. You’ll just be uncomfortably waiting to explode. Initiating the difficult conversation is like slowly twisting the cap on the bottle and letting the pressure slowly fizz away. To be successful – in both business and life – you must be willing and able to have difficult conversations. You’ll be happier too.


About Paul Kaye

Born in England, Paul got his first PD role in the early 2000s, making him the youngest programmer in the UK at the time. After nearly a decade programming in the UK Paul moved to Canada in 2012 to work for Newcap. Paul spends his days looking after stations in the CHR, Hot-AC and Classic Hits formats and also holds the role of National Talent Development Director for the company. A role that sees him working with morning shows, on air talent, and programmers across the country to improve performance. Paul lives in Vancouver and can be reached at ka*******@ma**.com

Paul Kaye | National Director – Talent Development | Newcap Radio

Other Puget Sound Radio articles by Paul Kaye HERE

Paul’s LinkedIn




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