Dealing with Difficult Conversations

What makes a conversation difficult and how does one deal with it?

How does one engage someone in difficult conversation

What makes a conversation difficult varies from conversation to conversation

There are any number of ways that we find ourselves faced with what we perceive as a difficult conversation. I am sure you have at some point in time experienced lost sleep, sweaty palms, and procrastination in anticipation of an impending difficult conversation.

But what makes a conversation a difficult conversation?

It really varies from conversation to conversation. It may be a cold call to a senior executive, having to make a team member redundant or confronting a relationship issue.

Difficult conversations makes people stressed

Difficult conversations impact our health and our productivity

Not only have difficult conversations the potential to impact on our health; increasing our heart rate, contributing to loss of sleep, increasing stress and anxiety – they also have a major impact on personal productivity as we perpetually run the story in our head as to how this difficult conversation is going to be conducted and played out, procrastinating over it for hours, days or even weeks - finding ourselves unable to focus on the job in hand.

What is going on in our minds when we perceive a conversation is going to be difficult

The value in being able to handle difficult conversations

Researching for this article alerted me to just how much of a direct cost there potentially can be when handling difficult conversations inappropriately.

Last Financial Year Psychological Injury Claims accounted for $100 million of Workers Compensation Claims

The Australian in April stated "The cost of psychological injuries to the federal government’s workers’ compensation scheme has soared nearly 50 per cent in the past four years, forcing a further review of the system to cut costs and improve treatment".

Maybe then there is value in being able to minimise and handle difficult conversations more effectively?

So what is going on?

A good place to start is to understand what is going on in our minds when we perceive or feel a conversation is going to be, or is, difficult.

In my own experience, particularly during my early sales career, I was often frustrated at how worried I'd become about how a conversation might go, and its potential to be difficult. I would procrastinate for days before picking up the phone or initiating the conversation. Only to then discover, on having the conversation, that the other party was delightful and it all went very easily and smoothly. ‘Difficult’ was just in my head, not in theirs at all. So why might this be so?

The Harvard Negotiation Project has distilled it down to three key things

Fifteen years of research by the Harvard Negotiation Project has distilled it down to three key things that we are processing in our thoughts:

What happened or didn't happen?

Conversations become difficult when there is a different recollection of what actually happened.

This one particularly resonates for me in my role as a father. With children, adults often find themselves in a frustrating conversational loop where we disagree on the facts.

I have had to ask you three times to go to do your homework and you are still not listening.

Frustrated Parent

Frustrated Parent

I heard you, Dad. I am going to be doing my homework soon.

Frustrated Child

Frustrated Child

The fact for them is that they have heard me, they are just choosing not to do. The fact for me is that they did not hear me because they are not doing it.

How we feel

Subject to our personality, we can get so caught up in our feelings and how the other party may be feeling that it becomes increasingly difficult to simply state what we need to happen. An internal dialogue goes around in our head about what we/they are feeling:

  • Are my feelings valid?
  • Is it OK to express my feelings?
  • What about the other party, have I hurt their feelings?
  • Am I going to hurt their feelings with my words?

The irony is that if we prefer to avoid conflicts. For example, our effort to not upset someone can actually create situations whereby we do just that - we upset them.

Your internal dialogue struggles with identity

Your internal dialogue struggles with identity and the perceptions about what you might lose or gain:

  • The impact the conversation may have on your relationship, career or reputation.
  • Whether you are seen as competent or incompetent.

This may show up at quite innocuous times. For example, have you ever been reticent to contribute during a team meeting or to put up your hand amongst a large audience to ask a question? Fear of how your question may be perceived by others stops you wanting to "expose" yourself.

So what might help?

Well, getting conscious as to how our own internal conversations can create the perception that a conversation is going to be difficult will certainly help. That said, some conversations will genuinely be difficult. What then?

At Hugh Gyton & Associates we recommend you apply the I.N.P.U.T. formula within a positive ‘conversation climate’. By that I mean, create an environment for success in terms of time and place for both parties then apply I.N.P.U.T. in how you have the conversation:


How might I have contributed, be contributing, to the problem. For example, an inability to say "no" can result in becoming overloaded with work and suddenly having a "performance" conversation with the boss.

What can I offer to help resolve things?

Remembering that someone disagreeing with you may not be wrong - now there's a thought.


Now is better than later. The longer you leave a difficult conversation the harder it becomes. The more you allow for things to be unsaid, the more emotional, more resentful, and potentially irrational it can become.


Talk in terms of Proof. Be objective not subjective, provide evidence of what's happening compared to what should be happening.


Allow yourself to Understand their positioning/reasoning. Adopt empathic listening and "seek first to understand, before being understood".

Recognise, though, that "understanding" is different to "accepting".


Take Time to mutually agree on a solution. What might we both do/say moving forward to minimise recurrence of a similar difficulty.

Remember the words of Mahatma Ghandi

Finally, some difficult conversations may be of our own choosing and some may be foisted upon you. To help yourself create a conversation climate that shines more than it rains remember the wise words of Mahatma Ghandi.

Happiness is when what you think, what you say, and what you do are in harmony

Mahatma Ghandi

Lawyer, politician, social activist, and writer

Wishing you more harmonious conversations than difficult ones.


Hugh - these are great tips. No matter how old I get , is still don't like a difficult conversation. However it helps me to ask myself what are the consequences, for me, for the other person or for the organization if I don' t have the conversation. What is the purpose of the conversation. Is it to benefit the system/ organization as a whole? Use my role, rather than me as a person. Eg say " In my role as XXXX I need to address an issue."

Annie Crawford

26-Jul-2017 03:25 PM

Thanks Annie, you and me both as far as difficult conversations go.

Love your question 'what are the consequences?' Specifically around NOT having the conversation. Of course can go both ways, sometimes we need to check-in with the consequences of having too. Are our intentions sound, are we trying to make things better or simply wanting to 'win'.

Congratulations on your continuing good work with CanToo, amazing stuff. See there are some significant changes ahead coming down the pipe. Good luck on finding another passionate, capable person to continue the great work already done. Sure there wont be any shortage of people who would wish to work with you and your wonderful organisation in a leadership role.

Hugh Gyton

Hugh Gyton

26-Jul-2017 06:54 PM

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