October 27 2013

Having Helpful Hard Conversations (Rules 1-5)


For many years I have been interested in learning how to have hard conversations that are productive, respectful and helpful.

When a topic of conversation is “hard” it is usually very important to one or both parties and it is often emotionally charged. Because of this, it is easy for hard conversations to descend into a yelling match or a hurtful attack or one person just shutting down completely. A hard conversation can end with one or both parties feeling even more distant and upset and unheard. Is that your experience? Well, if it is, know that there are a few simple rules that you can follow to help you and your friend, colleague, housemate, partner or family member have helpful hard conversations in the future.

These rules are not psychological theories. They are tried and true practical steps that my wife Cat & I employ with great deliberateness every time we have a hard conversation. They are the reason that we have almost never had a fight. Sure we’ve had lots and lots of hard conversations (in fact our year long dating relationship seemed to be one big boot camp of hard conversations), and we’ve also had the occasional heated argument – some that didn’t go very well. But as we learnt and applied the rules outlined below, we got better and better at having hard conversations and now, nearly two years into our marriage, I would have to say it’s possibly the aspect of our relationship that we do best incommunicating-love

The best thing about knowing how to have helpful hard conversations is that it has a wonderful “snowball” effect. Every time you have a hard conversation that leaves you feeling closer and more intimate and positive about what was just discussed, your trust in the other person grows. You develop a confidence that you can share anything with them and that they could share anything with you, and even when you hit something really difficult (like talking about an issue of sin or something very personal) you can go into the conversation knowing that however hard it is going through it, you will get through it and be better off for it.

If you’d like to see that sort of trust and confidence grow in your relationships, then read on and try to start employing the following rules.

(Note: I have presently come up with 13 rules for having hard conversations. I will post them over three blogs to make each post easier to read and reflect on)


RULE #1: Love

If you need to bring up a hard conversation, check your heart and your motives. If you are a Christian, you know that you are commanded by Jesus to even love your enemies, so there is no excuse for bringing up something hard with the motive of hurting, shaming or condemning the other person.

20131027-134508.jpgConsider Paul’s words in 1 Corinthians 13:4-6… “Love is patient, love is kind. It does not envy, it does not boast, it is not proud. It does not dishonour others, it is not self-seeking, it is not easily angered, it keeps no record of wrongs. Love does not delight in evil but rejoices with the truth.” Loving someone doesn’t mean you avoid hard conversations, after all, love rejoices with the truth! What love means is that you do so in a way that is marked by humility and selflessness. If you are just trying to pick a fight or get something off your chest, you will not be able to follow any of the other rules outlined below. As the first verse of 1 Corinthians 13 says, “If I speak in the tongues of men or of angels, but do not have love, I am only a resounding gong or a clanging cymbal.” That definitely describes what a loveless hard conversation can end up sounding like! Selfless love must guide all of our hard conversations, so before you bring something up, make sure you search your heart, test your motives and ask God to give you genuine love for the person you need to talk to.

Note: If, in the end, you can’t control your emotions or the topic of the hard conversation is so painful you just can’t think about acting lovingly, then consider bringing in a neutral third party (be it a mutual friend, pastor, or counsellor) to mediate the hard conversation. This in itself may be the most loving thing to do.


RULE #2: Choose the time and the place

There is no perfect time or place to have a hard conversation. By definition, hard conversations are… hard. In fact, in an effort to follow this rule, you can put off having a hard conversation almost indefinitely.
Having said that, in following the number #1 rule of Love, you will think about when and where it is most loving to have a hard conversation. In general, here are a few times or places that may not be the wisest to have a hard conversations:

  • When it’s late: This is a hard one to avoid, as you may have developed a habit of having deep and meaningful conversations ONLY late at night, but hard conversations during the day usually give both parties more time, energy and headspace.
  • When one or both of you are tired, unwell, stressed, angry or emotionally drained: Again, you may never be able to avoid these factors, but keep them in mind and see if waiting a day or two might be the best thing.willens_girlsfight_post
  • In public: Having a hard conversation when you’re out a a restaurant or when you’ve got friends over is just unfair. It creates opportunities for shaming and embarrassing that may feel satisfying, but do not come from a motivation of love. Also, if the hard conversation is stirring up emotions, the public setting will not allow either party to freely express themselves.
  • When you have limited time: It is unwise to start a hard conversation on the drive to an event or just before someone has to go to work. The pressure created by the limited time may easily make the conversation descend into an argument.
  • When you one or both of you needs time to think: You or the other person may not be great at having long conversations or articulating what you are feeling or thinking. It may be worth just flagging the conversation and it’s topic and asking if it can be thought about and talked about at another designated time. Yes, that may mean you say something like, “Darling, I want us to discuss how you spend your money. I know it may be a hard conversation, so I was wondering if we could talk about it tomorrow night.” Now, naturally the other person may have a few questions, and it may be fair and loving to clarify what you mean, but it still maybe good to suggest that the full conversation take place after you’ve both had time and space to reflect. If you start a hard conversation and you then realise the other person needs more time to think before they can properly respond, you would be loving to ask if they wanted to postpone the conversation til a later date. Putting the conversation on pause will take a lot of selflessness, as you probably needed a lot of courage just to bring up the hard conversation, but if may be vital for your conversation to be truly helpful.

TRY THIS: When there doesn’t need to be a hard conversation, ask your partner, friend or family member, this question: “If I ever had to bring up a hard issue with you, what would be the best way to do it? What sort of time and environment do you need to be able to hear me out and respond well?” Different people like different things. Some like physical space, some like their hand to be held. Some like it while relaxing at home, some like it while going for a walk. Now, of course, even this conversation may be a hard one for you to have if your relationship with the person is distant or strained, but when it is possible, learning the best time and place to have hard conversations may save you both a lot of grief.


RULE #3: “This is not going to come out right…”

When addressing a hard topic of conversation, one of the best ways of communicating properly is to “talk it out”. This means you have to just say whatever you can and then refine your words and your thoughts in discussion with the person listening. The problem is, the first few things we say may sound a lot harsher than we intend them to be. But the damage is done. The words are out there, and the other person has already begun defending themselves or attacking you back.

DemersOne of the main reasons we avoid hard conversations is we don’t know how best to explain what we are feeling and thinking. We worry that the person we want to talk to will not hear us out or hear us properly. We worry about communicating the wrong thing and hurting the other person unintentionally.

My solution to this is Rule #3. Before bringing up a hard conversation, you simply say, “This is not going to come out right…” and then you just keep going. What that opening statement does is give you permission to say what is on your mind before you have fully processed it. It allows you to get it off your chest. It opens up the discussion without an expectation that the words are going to be perfect or even completely accurate! It just gets the ball rolling.

It is very useful for the person being approached as well. It asks them to be patient and to not react straight away. It allows them to put down their defences a bit and just listen and allow the person to talk it out for a bit.

Now, it may feel a bit fake or artificial to start every hard conversation with the same 8 words, but if you both are aware of Rule #3, then it will remind you both of its purpose. Nowadays, my wife and I rarely use this rule as explicitly. For us now, it is often our “unspoken rule” where we both know when we begin a hard conversation that “this is not going to come out right”. But for the first year or two of our relationship we followed this rule, word for word. It served us very well and allowed us to have many helpful hard conversations. If you still feel like your working out how to have hard conversations with someone, I recommend allowing this opening sentence to be part of your agreed vocabulary.


RULE #4: Actively Listen

This rule is particularly relevant for the person who is approached, rather than the person initiating the hard conversation. If someone has asked, “Can we talk?” you’re probably a little nervous. If they then start by saying, “This is not going to come out right…” then you really will be worried. But hopefully you will also be patient and willing to let them talk it out. Your goal, before responding, before apologising, before defending, before correcting, before speaking… is to listen. As James (the brother of Jesus) writes: “My dear brothers and sisters, take note of this: Everyone should be quick to listen, slow to speak and slow to become angry, because human anger does not produce the righteousness that God desires.” (James 1:19-20) That’s great counsel – quick to listen and slow to speak.

Listening-nowThis is primarily what most people want when they are bringing up a hard conversation. We all want to be heard and understood. Even more than we want people to change, even more than we want people to apologise, we want them to first simply acknowledge what we are feeling. We want to be known and we want to know that the other person “gets us”. During a hard conversation, both parties must put listening as the primary goal of the conversation. If both parties are just trying to fight for their own voice to be heard then the conversation will descend into a battle of words.

There are many techniques for what the communication books call “active listening“. The most common and most helpful is repeating back to the person what you have heard them say. Even if you simply repeat word for word what they just said to you, it can be helpful to make sure they know that you have heard them. Other times, the person will find it more helpful if you put it in your own words, so that it shows that you have not only heard them, but you understand what they mean. The danger of this, is when people get too interpretative or when they filter what the person actually said through their own insecurities or wrong perceptions. For example: Mel says “I think it’s time we started going to the gym together.” Then Sam says, “So… you’re saying I’m fat and you find me repulsive?” This is bad active listening.

Basically, you never want the other person to have to say, “No, that’s not what I said!” Make sure you listen – carefully, intentionally, actively. To me, active listening is not so much a technique, but an attitude. It is an expression of love for the other person. Even if they are saying something that sounds harsh or unfair or ridiculous, you want to hear them out without judgement. You want to listen and you want them to feel heard.

REFLECT: One of the main reasons why people don’t bring up hard conversations is because they don’t feel like the other person will really listen. Are you that person? Think of your loved ones, your family members, your work colleagues. Do they possibly avoid talking to you about hard issues because you are prone to being quick to speak and slow to listen? Maybe ask someone if that’s true of you.


RULE #5: Be grateful that something hard was brought up

Try this next time someone brings up something hard with you… Thank them. Thank them that they told you about your bad breath. Thank them that they want to discuss your porn use. Thank them that they brought up the issue of your inappropriate parents. Before you respond, even if the hard topic has pushed all your buttons, make sure you take a breath… and thank them.

Why? Well, think about it. Bringing up the hard conversation with you would have been quite nerve-wracking. They would be worried about how you’ll react, worried if it’s worth bringing up, worried if they should just let it go, worried that you’ll misunderstand them. They may even be worried that bringing up this hard topic, whatever it is, might jeopardise your relationship with them. They faced all those worries and in the end decided that honesty was the best policy. They decided that you were worth it. And they also decided that you could take it. They put a lot of trust in you to bring this topic up. In fact, you could see their efforts to have this hard conversation as an incredible compliment! That’s right! Telling you that your breath stinks could actually be a compliment!


I keep bring up the “bad breath” example, because that is actually a hard conversation that Cat & I had a few months into our dating relationship. I’d like to say I wasn’t the one with the bad breath, but unfortunately that’s not true. Cat was terrified about bringing it up, but it was a real issue for her and so she awkwardly, nervously and bravely started the hard conversation. Now, of course, I was embarrassed and in the moment I would have preferred for Cat to simply endure my face-melting halitosis rather than to have to talk about it, but even back then, I knew the principle of Rule #5. Very quickly I said, “Thank you Cat. That would have taken a lot of courage to bring that up. Bad breath is one of those taboo topics that no one talks about, so it really shows that you value this relationship to want to talk to me about it. It also shows that you trusted that I wouldn’t fly off the handle. Thank you.” Immediately, Cat let out a sigh of relief and we began a conversation that was a little less hard and much more helpful.


Now, that’s all I’ll give you to think about for now. I will leave the other rules for another blog post.

But if you’re curious as to what they are, I have put them below.

RULE #6: Trust their motives

RULE #7: Stick to the topic

RULE #8: Avoid absolute language

RULE #9: Allow absolute language

RULE #10: Be ok with ending the conversation unresolved

RULE #11: Respond with what you both understand and what you will both do

RULE #12: Pray

RULE #13: You both have to be more committed to the rules than the conversation


Try putting them into practise. Read through this blog with your partner or friend and discuss, how you can implement them. That itself may be a hard conversation!

If any of them are helpful, please post a comment (I always appreciate them) and feel free to share this blog with others.

Finally, here’s something, just for a laugh!



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Posted October 27, 2013 by Simon in category "Life", "Relationships


  1. By Rebecca John on

    Thanks Simon! Some great insights and helpful tips. We also have been putting many of these things into place for years, and it really makes our home a more peaceful place, even when the hard conversations need to happen.

  2. By Jane Knowles on

    Thanks for taking the time, Simon. These are really helpful and who wouldn’t want the rewards that adopting these rules bring into a relationship!

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