Sometimes unpopular decisions must be made for the greater good.
Sometimes you must deliver news that you know is going to be devastating to the recipient.
Sometimes you have no choice but to bring something to someone’s attention that may be slightly awkward or embarrassing.
Difficult conversations need to be had, and although we have no choice about the information we’re delivering, we can choose how we deliver that information.
The sad truth is, many of us are terrible at having difficult conversations and delivering bad news. The reasons for this are many and varied but I’ll focus on a few here and how we can all do better.
It’s just… so…Urgh!
The obvious reason is that it’s just so bloody awkward! Whether it’s a conversation with your reports about potential redundancies or a convo with your mate about their poor personal hygiene, it just feels so wrong.
Firstly, you don’t want to hurt their feelings or have them think that you think badly of them. Secondly, you don’t want to destroy their confidence – particularly if you know their confidence is already so low it’s shaking hands with Satan. Then there’s the worry of not knowing how the person will react. This might not be so much of a problem if you already know the person well, but if it’s someone you have little to no relationship with or someone who is known to be quite volatile, you may have a situation on your hands.
The fact is, the awkwardness is a temporary state, it will pass. As for not wanting to hurt people, if you are sincere in your approach and delivery, people will, for the most part, understand, even if they’re not happy about it. As for the potential emotional outburst of the person or people involved, allow them to experience their feelings – within reason of course! Physical violence and/or personal verbal insults – absolutely not! Raised voices, anger, tears…Yes. Depending on the information you’ve shared the latter may be understandable. You may not be comfortable with certain (non-violent) expressions of emotions, but in that moment, it’s not about you, so allow the person or people to feel how they feel.
You’ve brought into the ‘You’ve gotta be cruel to be kind’ myth
I think that we can all agree that being cruel to be kind is nonsense. Being kind to be kind makes much more sense. That said, some people prefer the ‘give it to me straight Doc’ approach, and if this is true of the person/people you’re breaking bad news to, then have at it! When breaking bad news to entire organisations however, or with someone you don’t know very well, you may want to be a little softer in your approach just to be on the safe side.
Remember what the late, great Maya Angelou said – Or was it Frank A Patterson Jr? Or Jerry Johnson? Or Carole Buchner…? I dunno but someone said:
“They may forget what you said, but they will never forget how you made them feel”.
-Someone
You find emotions icky
Back in 2021 while I was in hospital, with a potentially life-threatening illness, during the pandemic, all alone because visitors weren’t allowed, I was talking to someone on the phone and I started to cry. Their response? ‘Don’t be sad’ So I stopped being sad and we all lived happily ever after.
Eyeroll
Some people are not good at dealing with emotions – be it their own or anyone else’s. I know people who will literally walk away if the person they’re interacting with starts to cry. I also know people who genuinely believe that depression is a choice.
While the coach in me might suggest that such people do deep dive into why they are so, um, emotio-phobic, the realist in me knows that many people won’t – and they don’t have to if they don’t want to. However, when delivering bad news, this, er, emotio-phobia will cause problems.
If empathy doesn’t come naturally to you then prepare and practice what you’re going to say in the lead-up to the conversation in the same way you would prepare a speech leading up to an event. You may also want to run through what you’re going to say, and discuss your approach with someone who hasn’t undergone an emotion-ectomy to make sure that you’re approaching the conversation in the right way.
Likeability takes centre stage
By far, the most annoying group of the ‘bad at having difficult conversations crew’ is the ‘I desperately need to be liked’ people.
Obviously, most people want to be liked (others are indifferent – or as I like to call them, my heroes!) but when your need to be liked overshadows your ability to speak and act honestly and authentically, you may have a problem. Worse, you may be causing problems for others.
As a coach, I’ve sometimes had to raise things with clients that were…sensitive shall we say. It’s a necessary part of what I do – I ask questions and challenge people – not in a confrontational manner, but more as a way of helping them to explore unexplored areas in their development journey. If I didn’t do this, I wouldn’t be a very good coach.
To put it another way, if your doctor only gave you good news because she didn’t want to run the risk of being disliked by you, would you trust that she had your best interests at heart?
The fact is the most likeable people are honest in their relationships with others. They’re likeable because we can rely on them to both congratulate and challenge us in equal measure. They also have the confidence to say what needs to be said, and the emotional intelligence to say it with tact and care.
Hiding from difficult conversations doesn’t make you likeable, it makes you dangerous because if faced with the option of doing what’s right or currying favour, you will always choose the latter.
You don’t acknowledge the person/people
Sometimes decisions have to be made quickly. You don’t always have the time to do everything and involve everyone that you normally would. In situations like this, it’s imperative that you communicate clearly, often, and most importantly, effectively with those who are going to be affected.
Aside from this being basic common decency, at best, the people most likely to be affected by the decision(s) made may be able to offer insights they have from personal experience that could possibly change the outcome of the decision. At worst, nothing changes, the decision still stands but those affected have had the opportunity to be heard and have their concerns and ideas taken into consideration prior to the decision being made.
Having things done to you as opposed to being involved in the decisions that affect you is a very unpleasant experience – particularly if you are already part of a marginalised group or community who are often disenfranchised, ignored, and forced to bear the brunt of the poor decisions made by others, both historically and in the present day.
Let’s say, for example, your elderly relative has been living with you for a number of years but it’s now becoming more difficult for you to meet the demands of their care. Simply sitting them down and telling them that you have decided to relocate them to residential care and that they leave next Friday, is horrific!
This person is already vulnerable by being an elder (a very ignored and dismissed group in society) and unwell. They are already prone to having people speak about them instead of with them and here you are doing the same thing.
Instead, a better approach would be to (if possible) share your concerns with them. Be honest about the situation and ask if they have any ideas about how to resolve the issue. Explain that relocation is one idea but that you’re open to any other suggestions or ideas.
They may suggest living with another relative. That other relative may be very happy to have them and that’s that. Or there may be no other options and you all have no choice but to go forward with the relocation, in which case, at least your relative was involved in the decision. There is dignity in this, and everyone deserves dignity.
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Look, as the name suggests, difficult conversations are…Difficult. Very few people – if any – know instinctively how to handle them. It takes time, practice, and most of all a good sense of care, empathy, and respect for others. You can read about and attend courses about difficult conversations but ultimately in its simplest form, your role in leading these conversations is to verbally usher someone through a challenging experience.
If in doubt, think of it this way: If a building you were in was on fire, would you want the fireperson to throw you head-first out of the 3rd floor window, with no life net to break your fall? Or would you want them to follow a careful exit plan that ensures minimal additional damage to you?









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