A friend called recently after initiating a tough talk with his boss. He confided that he was shaking during the talk, had a knot in his stomach from the time he decided he needed to have the exchange and was somewhat relieved but was quite unsure of the outcome. He had a difficult conversation.

The only thing he knew for sure was it was something he needed to do for some time, that he was pleased he had mustered up the courage to have the hard talk and that it had been really challenging.

The term “difficult conversations” has been rebranded recently by authors and coaches as “courageous,” “impossible,” “uncomfortable,” “dreaded,” “avoidant” or “discomfort zone” conversations, among others.

'These are conversations where we will raise things that people may not like to hear, have the potential to offend or embarrass or, when improperly conducted, may have an air of confrontation to them.'

Such euphemisms convey that these are conversations where we will raise things that people may not like to hear, have the potential to offend or embarrass or, when improperly conducted, may have an air of confrontation to them.

Many have commented to me that any workplace conversation that makes you uncomfortable is potentially a difficult conversation and what is difficult for one may well not make the grade as difficult for another.

For many, the risk of damaging a relationship is what defines difficult while for others, it’s the chance of rejection, the flaring of emotions or any conversation in the workplace you would rather put off.

What I know for sure is that exercising leadership, regardless of one’s role or title, requires the courage and ability to have difficult conversations and do them well.

Harvard’s Douglas Stone, Bruce Patton, and Sheila Heen in their 1999 definitive book on the topic entitled Difficult Conversations: How to Discuss What Matters Most urged readers to “sort out the three conversations” contained in any one difficult conversation.

They contend that any one difficult conversation contains a “What Happened” portion that uncovers the situation, a “Feelings Conversation” where charged emotions may be exposed and constitute why most people feel the conversation is difficult in the first place.

And lastly, an “Identity Conversation” where we feel threatened by the situation because we don’t know how it will impact the relationship.

The book goes on to explore the notions of “Disentangling Intent from Impact” and the very helpful “Shift from Certainty to Curiosity."

The authors’ Triad Consulting Group offers very helpful free resources by way of a Difficult Conversation Preparation Worksheet.

'The overriding advice from many sources regarding difficult conversations centers around making them happen in the first place because they can create meaningful learning opportunities.'

The overriding advice from many sources regarding difficult conversations centres around making them happen in the first place because they can create meaningful learning opportunities.

In her book The Discomfort Zone – How Leaders Turn Difficult Conversations into Breakthroughsauthor and coach Marci Reynolds claims “the discomfort zone is the moment of uncertainty when people are most open to learning.” 

She argues that difficult conversations present unmatched opportunities to break through barriers and focus on improvement as well as exploring better outcomes in the future.

Admittedly not all difficult conversations have a coaching or development angle.

At times, they are just the challenging talks that we need to have at work. Termination interviews, a disciplinary discussion or other painful exchanges come to mind.

However, some of the same advice holds true from difficult coaching type conversations.

Namely, having clarity and potentially some data about why the chat is happening in the first place, using inquiry, asking respectful and insightful questions and curiosity, as well as being mindful of time, place and openings and closings.

Empathy through lots (and lots) of listening is also the order of the day.

Having a difficult conversation does not guarantee progress.

However, as my friend commented after the tough talk he initiated with his boss, “not having the conversation probably guarantees that no progress would be made.”