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How to have hard conversations – it doesn’t have to be that hard

All of us at some point in our lives will need to have a difficult conversation with someone.  It can feel very scary in advance of these conversations, and as a result people often avoid them.  Sadly, the result of avoidance is almost always worse.  

I was a CEO of a company for 18 years – more than half my adult life – and because of that I’ve had to do hundreds of difficult conversations in that role (as well as quite a few personal ones).  I want to share some practical advice based on what I’ve learned – there really are some things you should do and some things you must never do.  

I’m going to describe some thoughts in three separate areas:- How to approach the conversation- What to say at the start- How to end.

But the main thing to have in the back of your mind is that the conversation needs to be had with dignity, for both you and the other person.  These ideas are about how to do that.

How to approach the conversation

By far the most important thing here is to ask yourself “what do I want to achieve?”.  If the conversation went exactly as you wanted it, what is the best outcome you could hope for?  If you don’t know this, then don’t have the conversation until you do.  

Not doing this is the biggest mistake I’ve seen people make over the years.  What they want to do is “express themselves” which really means they have a bunch of negative things to say to the other person.  This is pointless and juvenile – if you would prefer not to be shouted at or insulted then don’t do it to someone else.  In all my years, of all the disagreements I’ve seen the vast majority of them are just poor communication, rather than a conspiracy (someone deliberately trying to be harmful or hurtful).  It is by far the best policy to assume the person you need to have the conversation has the best intentions, however much you may think this is not the case.  I am constantly surprised by the very different conclusions others can come to based on the same information – and therefore it is more likely that any worry you have about the conversation is just because better communication is needed.  

The second thing you must do, once you know what you want to achieve, is ask yourself whether what you want is fair.  Let me give you an example of unfair to illustrate the point.  My wife, whom I love very dearly, has the highest standards of cleanliness in the home of anyone I know.  I am not naturally as concerned about this as she is, and therefore I have, once or twice, been on the wrong side of a conversation about cleanliness with her over the years.  Now, if that was to annoy me, I might conclude I need to have a conversation with her about her cleanliness standards!  But that is completely unfair.  It is who she is – asking her to be different requires her to deny that.  As importantly, I married her in full knowledge of this, so having an issue with it is completely unreasonable.

For the record, I have no issue…!  But the point is, if what you want is to deny someone’s nature, or more generally is just unreasonable, you need to re-think and work out something that you would be happy with that is reasonable and fair.  

The key is, before you even start a conversation, know what you want and that it is fair to ask it.  If you aren’t sure, think some more.  Then when you get into the conversation, do not deviate from that.  More on that next.  Equally, if you can’t work out what you want, maybe the issue is yours and you should just forget about the issue and move on.  Sometimes that is the best policy, depending on the situation – if dealing with the issue requires you to hurt someone badly, is it worth it?  The price of addressing your issue may be high – it is worth considering whether you think it’s worth paying.

What to say to start

This is a lot easier if you know what you want, but still the hardest part.  

First things first – never have a hard conversation when you’re angry or upset, unless it’s absolutely unavoidable.  It is much less likely to go well than if you’re calm.  

Next – what you actually say to address the issue depends a lot on what you’re trying to do, and sometimes the hardest issue is just getting into the conversation.  Here are a number ofexamples with suggestions:- The simplest is where you want to share some information and you know it might not be well received. The easiest way is to say something like “I’d really appreciate it if I could share something with you.  This will be difficult for me to say, but here goes…”  Then say it.  In this instance your objective is just to get the information out there.  – Someone is behaving oddly, or wrongly and you need to address it but you aren’t clear why.  I find the easiest way to start these is to ask “is something wrong?  Because I’m seeing some behaviours that don’t seem like you, and if I can I’d like to help”.  Hear them out and maybe you’ll find out something is wrong.  Maybe you won’t, and then you just need to make it clear that the behaviours aren’t working for you and you need to find a way to have them end. – Someone is doing something that really annoys you. Assuming you’ve decided it’s fair that you address this, then I would suggest you address it in the following way; “Can I ask you something – when you do [insert the behaviour/action], are you aware of the effect it’s having on others?”  And then stop and leave some silence.  See what happens.  Because of the way this question is asked, you are forcing the person, albeit gently, to confront the fact that the action does have a consequence.  They can say “yes, but I like doing it anyway”.  You will need to decide how you feel about this.  I might be inclined to say “ok – but you need to know it doesn’t work for me at all, and I’m going to need to think about how to react to your response as a result, because I wasn’t expecting you to answer that way”.  More likely than not they will answer the opposite way, which gives you a way of addressing the issue in a more straightforward way, by describing the effect on you.  – You know someone has a problem or an issue and you want to help them deal with it.  In this case, your objective is the help, not the confrontation.  This is probably the toughest of all.  In my experience the best strategy here is to have a normal conversation and work out whether you have the opportunity to have the conversation.  You may not, and therefore you will need to wait.  The critical issue here is that people who need help have the right to decide not to take it.  They therefore have to want it, for you to be able to give it.  I remember a conversation with a friend some time ago where I knew he had an issue, but it became clear he believed he had a different one.  I could therefore see why he was ignoring the problem I thought he had and focusing on the one at hand, because the latter one was bigger and more important to him.  Conversations bring new information, and your job in this situation is encouragement and support, rather than telling people that they need help to do something better.    

But whatever you do, don’t ever deviate from what you are trying to achieve.  Equally, people may come back at you with alternative problems they may have with things you are doing– something like “well I’m only doing this because you do that…”.  What you need to do is to avoid them being linked.  Say something like “ok, I hadn’t realised you had that issue and I want to talk some more about it with you.  But obviously having an issue with something I’m doing doesn’t give anyone the right to behave however they want in return, so let’s keep the issues separate”.  I would probably offer to deal with their issue first in the spirit of generosity, but the key thing is that they aren’t linked.  People need to be clear that one issue doesn’t justify the creation of another. 

How to end

You may wonder why I’ve made ending a section!  The reason for this is hard conversations need to finish well.  This is critically because the main thing you are trying to avoid is the conversation turning into mudslinging or insults, which they so easily can if you’re not careful.  

In my experience there are three broad ways in which the conversation will go.  I explain these below and how to finish in each case.1. The conversation goes well.  The person is very appreciative of what you have to say, and receives well what you have to say.  You might think this is easy – it certainly is the easiest (!) – but you must take the opportunity in ending the conversation to thanks for being so understanding.  Something like “I’m really grateful for how you listened to me – it’s been hugely valuable for me to have this conversation and you’ve made me feel so much better.  Thanks you so much”.  It’s simple but important – leave the other person the dignity of feeling the positive effect their behaviour has had on you.2. The person engages well with you, and shares something that seems like a fair argument against what you’re saying. The best way to deal with that is like this – “that’s a very interesting perspective – thank you for sharing it with me and I think I’m going to need some time to reflect.  May I do that and then come back and continue?”  What has happened is you’ve found out something you probably didn’t know, that may put a different complexion on the subject.  You therefore need to give yourself some time to think about it.  3. The person reacts badly and possibly angrily.  It becomes clear the conversation isn’t going well.  There are threeways this might happen.  One is mid conversation – they explode early before you have a chance to get out your point.  At this point you need to remove yourself from the conversation, using something like “I’ve obviously upset you and I’m sorry – perhaps we should have this conversation another time when you’re ready”.  Do not lose it, under any circumstance – it never helps.  The secondsituation is where the conversation happens, but the result is you are still in disagreement.  In this situation you are best to acknowledge that you aren’t agreeing and suggest you both go away and think about how to find some common ground.  Third, in some situations there can’t be common ground and you just need to get the information out there.  In this instance your best bet is to say something like “I understand what I’ve said isn’t easy to hear, and that you don’t necessarily agree – but as difficult as it is to hear I didneed to tell it to you, and I’m grateful for you hearing me out”.  In all these situations, time is the healer, and that’s why dealing appreciatively and supportively is so important – the fact that you did won’t generally in the long term be ignored by people (and even if it is, you dealt with the issue constructively and it is at least out there).  

In the either of 2 or 3, take the opportunity to get some advice from someone you trust once you understand where the other person is coming from.  And remember, as much as you may not like it, they are as entitled to their views as you are to yours, however much you disagree.  

Concluding thoughts…

I hope that this has helped, at least in some small way, with how to have difficult conversations.  Trust me, they get easier with time the more you have them – the older you get the more it will become clear that being direct with dignity can just become part of your normal behaviour.  Fewer conversations will seem hard with time.  

They key to it is this – dignity is being clear about what you want and believing it’s reasonable, being prepared to listen to an alternative point of view, and never losing you calm.  And be grateful for the time that people spend with you!  Even if you are their boss or parent…gratitude is never wrong. 

Good luck!

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