Six Tips for Managing Difficult Conversations

difficult conversationsGetting started is the hardest part.  It’s getting past that awkward pause before you begin or worse still, explaining why you want to talk. Part of the challenge is that often by asking for the conversation, you end up having the conversation before you’re really ready. That’s something to avoid. No good comes from having the conversation when you’re not prepared. Of course, you could always hijack the other person into a discussion they didn’t anticipate. If that seems unfair, it’s because it is. You are also likely to end up in a defensive and angry discussion when resolving, revealing or relieving the issue  should be your first priority.

Some phrases to consider:

  • I’d like to talk to you about – but first I’d like your point of view.
  • I need your help with something. Can we talk about it soon?
  • I have something to discuss with you that I think will help us work together more effectively.
  • I think we have different perceptions about __ and I’d like to hear your thinking on it.

Pick your location wisely. Where a difficult conversation happens is often as important as how the conversation happens. It will hardly make the process easier for you if the setting is full of distractions. So start by ensuring that you are prepared to speak and that the setting is conducive to clear communication. In an office scenario I ask people out for coffee to avoid any possibility of being overheard. Being the centre of office gossip is only interesting on TV. I’ve sent someone away from their desk because their boss was having a discussion about them within their hearing. I then told the person having the discussion that others, including the subject of their discussion, could hear them and could they keep it down or move. I don’t think much of private discussions held in public.

There are always two people in a discussion. Remember that any discussion is a two-way activity. Although what you have to say may be weighing on your mind, you won’t know what is on the mind of the other person unless you give them room to speak.  Open the floor; ask them what they think about what was said and if they can think of a way for you both to resolve the issue. You may have a great idea, but they may have a better one.

Don’t spend too much time in a negative discussion. Give yourself time to talk but don’t give yourself too much time. What can be accomplished in 30 minutes can be undone in 60. Set another time to meet if you can’t get it all out.  This will give you a chance to cool down, consider the discussion and contemplate new solutions based on what you learned.

Get clarity and acknowledge emotions. One of the most effective ways of breaking down the negative rhetoric that comes from difficult conversations is repeating back to the person what you think you heard them say. A few years back, a colleague of mine was quite angry.  An important document had gotten mixed up with less important pieces and subsequently redirected to our correspondence unit. I answered the phone and was met with yelling. She was shouting at me about how important the document was and how time sensitive and how much trouble it had caused when it went missing, and then repeating.  In the middle of the second go around I said, “I know it was important and urgent, that’s why I sent it to you right away. Are you angry at me because a paper clip from another document in the envelope snagged it and so you mistakenly sent it to correspondence?”

There was a pause as she considered, then a very quiet, ‘“Yes.”

“Would you like me to staple documents in the future?” I asked. Again a pause, then a very calm “yes” followed.  The conversation ended shortly after that. Given our respective positions, the conversation made no sense, being angry, even less, but sometimes anxiety gets the best of you and before you know it, you’re having a difficult conversation.

If you’re thinking that I am naturally a calm person, you would be wrong. The only reason I wasn’t yelling back was because I have interpersonal communications training. What the exchange taught me was that the tactics work.  All my yelling would have done was escalate things and waste time in a pointless finger pointing activity. By keeping my tone even and paraphrasing what I heard, the discussion slowed and stopped.

There is power in being wrong. Perhaps one of the most difficult things about difficult conversations is acknowledging when you are wrong. We all take pride in our opinions and I think most people strive to do the right thing. So when you find yourself in a situation where you are wrong, it can be very challenging to acknowledge and to respond appropriately. The thing is, when you acknowledge you are wrong it can be such a powerful action, particularly as a leader. When you acknowledge you are wrong, it tells people who report to you that they can own up to mistakes too.  It tells colleagues that they can trust you to be fair and it tells bosses that if you don’t back down from an issue, it isn’t because of pride.

On a final note, don’t forget your body is in the conversation with you.  Make sure you are not sending one message with your body and another with your mouth – no arms folded across your chest.

Have you ever had to have a difficult conversation?  How did you handle it? There are many, many tips for managing difficult conversations, what are some of your best practices for dealing with tough discussions?

About Debra Yearwood

Experienced communications and public relations executive who manages challenges with an eye on outcomes and a sense of humour. Learn more about how I think at https://commstorm.com/ Learn more about my experience at ca.linkedin.com/in/debrayearwood/
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39 Responses to Six Tips for Managing Difficult Conversations

  1. Thanks so much for sharing all of the awesome information!
    I’m looking forward to going over more posts!

  2. I think the most important thing when engaging in a difficult conversation is to stay calm. I try to approach the topic, by looking at things from the other person’s point of view before engaging. Sometimes no response is the best response. Silence speaks, but without antagonism. Someone phoned me recently to apologize for events that occurred over a year ago. It took courage and I accepted the apology, but with no intention of resuming contact. During the conversation, he mentioned a few times that we should talk again and stay in touch. I chose not to reply to any of those comments. Since he spoke a lot, I wasn’t sure he heard the silence surrounding his invitation. When silence is experienced during a conversation, it need not be awkward. It’s important to give yourself the time to process what is being said and not to respond when you are angry. Silence is also a powerful statement. It says more than words, though I am not suggesting that you give someone “The silent treatment.” After sticking my foot in my mouth numerous times, I’ve learned to try to think before I speak.

  3. Leora says:

    Ah, yes. Difficult conversations! The hardest are with my daughter, because then I am most likely to lose my temper. I think it’s because she knows how to push my buttons. With just about everyone else, I can remain relatively calm. “I” statements help, as in “I” own the problem, so I’ll talk from that angle. But one has to be calm when one speaks. Easier said than done. And then listen, too!

    • Leora apparently misery does love company because I’m glad to know I’m not the only one who has a hard time with her daughter.🙂 It’s not even that she is argumentative, but when we do argue I find myself forgetting all of the best practices.

      You are so right, you have to be calm. By staying calm, you think things through and increase your ability to hear the issue as the other person see’s it. You’re also better at articulating your own perspective.

  4. Good article Debra.

    It’s amazing how much we can learn when we take the time to listen. And it enables us to have a successful discussion. Only broadcasting what you want to say is a monologue and can easily work against you.

    Learnt a long time ago to admit when I’m wrong, Even if I’m not but some team of mine didn’t show up for an interview when the upset person had confused the date and time. What’s the point in correcting her. Much better to aplogize, which will make him/her feel good and re-schedule the appointment.

    Love how you managed a discussion by stating “Would you like me to staple documents in the future?” I asked.” Excellent example of what to say to angry people.

    • Catarina, you make a great point, ending the conflict. I think there are times when we get caught up in winning an argument and forget that there is a time and place for everything. Most of the time in work settings, bringing an end to the friction is by far more important than winning an argument or being proven right. If the issue is important, you will be better off addressing it when everyone is calm any way.

  5. Good piece, Debra. I especially like this part: “By keeping my tone even and paraphrasing what I heard, the discussion slowed and stopped.” I’ve benefitted from a number of different trainings and books on difficult conversations. I’d say the best has been Marshall Rosenburg’s Non-Violent Communication, a body of thought and practice that he’s developed over several decades. Are you familiar with it? It’s based on owning the fact that you have needs, and so do others. And you dialogue about how you might both get your needs met. One caveat: I’ve learned to not attempt this technique (or any difficult conversation) via email. In person is always best, followed by the telephone as a reasonable second best option. Thanks again for a heartful, practical post, Debra.

    • I’m not familiar with Marshall Rosenburg’s work, but will look into it as this is a topic that never gets old for me. Alison I have to admit to an active mistrust of e-mail as an effective communications device. It has it’s benefits to be sure, but it can create problems, particularly in any conflict situation. It is rarely if ever the mechanism for resolving problems. In fact, I have posted in my blog about the perils of email in a post called E-Mail VS Communications. Thank you for your kind words.

  6. Diana says:

    Nice post, Debra! Gives plenty of food for thought… I don’t like difficult conversations and usually try to “prevent” them from happening… i mean, to foresee where a problem might occur and address it before we even reach the point when we need to have a difficult conversation.

    In any case, to all of your great tips – i would add “Be honest, always”. We shouldn’t be worried about hurting other person’s feelings or something. Honesty is the best policy, ever. This of course doesn’t mean we should be rude or something – but sugar coating isn’t something which would help us in the difficult conversation and certainly not in to resolving the problem (if there is one).

  7. Once again your post has helped me see how much I have gained from being in the classroom. Sometimes I don’t allow myself to see how communication tactics transfer from one arena to another, so thank you for articulating it so well.

    • I’m not at all surprised that managing difficult conversations would be an inherent part of being a teacher. All the fragile and opinionated egos you have to manage, then of course there are the children.🙂 I think the classroom is very much a microcosm of society only without many of the filters that age can bring.

  8. Lorraine Marie Reguly says:

    One other thing to mention is that if you are going to have a confrontation with your child, you should pick a time and date to have it. They will then be expecting it, and so their minds will be open and receptive to what you need to say.

    • Very true Lorraine. It’s funny how the considerations that we put in place for our colleagues are often forgotten for family, yet the same rules apply. Giving them notice, taking their views into consideration, giving them privacy etc. are all going to impact the outcome of the conversation. The formality is less, but the thoughtfulness shouldn’t be.

  9. Arleen says:

    As always Debra a good article and well written.

    I have been in sales so long that I am able to turn something ugly into a happy ending.

    When a customer gets mad and is unhappy with let’s say one of my employees, the first thing I do is get on the phone and call. First thing is that I acknowledge their frustrations. I usually say I understand you had a problem with…… The most important thing you can do is Listen and shut up while the other is venting. Then I will say I am sorry you had a bad experience, …. is our top salesperson and I am surprised about what happen, but I will talk to her. Now tell me what is the problem. Nine times out of ten, they really want someone who will listen. Then I usually will say what can we do to make it right? Immediately the guard comes down and the customer’s whole attitude turns around. Then many times I will hear them admit that the person wasn’t that bad but it was really something that happened to cause them to go off in the first place.

    I have always looked at things in my business is no one is perfect, there will always be mistakes, but at the end of the day, it is how you handle them. If you can diffuse an argument and acknowledge if you are wrong the energy is more powerful

    • Thanks Arleen. It doesn’t surprise me that you tackle the situation head on, you mentioned that the first thing you do is contact the upset customer. This is so much more effective than waiting and trying to avoid the situation. It gives that person faith that you really do want to manage the situation. In fact everything you say to them is about addressing the issue and creating space for them to calm down.

  10. I agree that location is very important when it comes to discussing a hard conversation. Privacy is usually a concern as well as how calming the environment may or may not be.

  11. Glynis Jolly says:

    I usually start out those types of conversations with something like ‘What is your reason for doing it that way?’, or ‘It may be better to do it this other way. What do you think?’ Sometimes the reason something is being done in a way you don’t agree with is valid and sensible, and we just want it done our way because we were not aware of another way. By asking a question, I get the chance to understand that person’s logic and, therefore, have an easier time dealing with the situation.

  12. Kirsten says:

    Great advice…Having these conversations can be very difficult these tips will definitely help.

  13. Debra – What a wonderful post. It is so important to plan out your actions before you get ready to “talk” with someone. I whole heartily agree with you on not focusing on the negative.🙂

    • Thanks Susan. I can’t see the value of going into that kind of conversation negative. Any time I’ve started a difficult conversation while angry it has ended in less understanding. Even if I get what I want, I never like how it came about.

  14. Jason B says:

    I’m not too fond of difficult conversations, but sometimes you have to have them. Sometimes they help you grow as a person.

    • Undoubtedly you grow from having them. Remember that old expression, “what doesn’t kill you will make you stronger”. Having a difficult conversation isn’t quite that severe, but it can feel that way when you know you have to have one.

  15. I was thinking about all the “difficult conversations” I had when I was a sales manager. Yikes. Some of them were down right awful. One particular situation had me caught in the middle with a top salesperson who was regularly berating our admin staff. When one of the women called me about it she said it was the last time she would put up with it. It ended horribly. There actually was one conversation: I told her supervisor he had to talk with her and change needed to happen quickly or else, she had to be let go. Things didn’t change. She was gone.

    We can do all we can do and sometimes that is not enough. Difficult conversations can just be difficult.

    • Good point Patricia, sometimes you just have to accept that no matter how you phrase it, difficult conversations will be difficult. One of the toughest work conversations has got to be laying someone off, no matter how you phrase it, they are still out of a job when the conversation is done.

  16. Joanne says:

    I had to tell someone I couldn’t take their job after I said I would. I found the client to be difficult and I was unable to give them what they wanted. Although I did not say they were difficult, I did say I was unable to give them what they wanted. They were a little upset but found someone new. It all worked out in the end. If I didn’t have that conversation I would have been miserable, probably put out awful work that I think would later bite me in the butt. I find that when you are true to how you feel when having the conversation, it gives you confidence in being able to handle any roadblocks in the conversation, avoiding the making the lie bigger and remembering that you said it

  17. I have had communication training and such but still I am horrible at talking to people in general. I am usually one of them socially awkward people that comes across different than intended. It still amazes me though when I run across people that don’t understand the simply formula, praise in public condemn in private.

    • Jon, I used to think that formula was simple, but that’s not at all clear. Not long ago I was reading a post on Write Speak Sell called, “Is this a new trend ? The public firing of employees” and I was stunned at the examples provided of public firings, notable among them was behaviour from AOL’s CEO. Apparently some things have to be taught, repeatedly.

  18. jacquiegum says:

    You know, this is really a global answer for any difficult conversation…spouse, friend or co-worker. And so much value in minding the body language. I can’t tell you how much I resent a person that has semi-ugly words couched in a huge grin. It’s dishonest. Tell me your mad, lose the passive aggressive and let’s work it out. Body language betrays that every time…hands on hips or arms crossed across chest. It’s an escape hatch, so if the victim calls them out they can say, But I was only kidding!”

    • A smile so sharp it cuts is how I describe that special kind of exchange. The toughest people I have ever had to deal with are those who are passive aggressive. I’ve learned to call them on the behaviour. I do it consistently until eventually, it’s just too awkward for them to keep doing. It saves me and them a lot of grief in the long run and avoids an office full of tension.

  19. No one likes difficult conversations.The approach is different depending on the relationships. The most difficult conversations in business are between manager and subordinate. That’s why managers so often avoid them and then at at the annual performance review unload on the subordinate. It’s important to have the difficult conversation as close as possible to the event causing the discomfort. You’ve got to clear the air and counsel the employee on how to improve. Be very specific about the problem. This isn’t a time, in my view, to sugar coat the issue. But it is essential to be kind but firm, always showing mutual respect.

    • I have never understood the point of dumping on a subordinate at the end of the year. It’s like creating a stew of angry. You are absolutely correct in saying that the time to deal with the problem is as close as possible to the event causing the discomfort. Not only do you both have a clear recollection of the event, but if behaviour needs to be modified, it should be done before it becomes ingrained. I don’t think skirting the issue or sugar coating will help, but I do think remembering that you are dealing with a person and not a problem is key to keeping the tone even.

  20. Laurèl Craib says:

    Good article, thank you. I have learned that there is great benefit from a cooling off period between the two parties in disagreement before any difficult conversations. Firecracker engagement is unfair to the unexpecting recipient, plus the office, or the coffee shop, is not a battle ground. A communication attack of any kind can never end well, and in my experience, it can do enough damage that your working environment and relationships are subsequently ruined. Also, rather than having harsh words when things get sticky with a colleague, I prefer to use what I call a sugar sandwich. In the difficult conversation I make sure to start with stating a good attribute about my colleague, “Hey, did I mention to you that I thought that you handled the presentation with flare and finesse?”. Then I bring up the issue of friction, “I need you to know that I really do not appreciate when you mentioned that my branch did not meet our targets,”, and I finish by messaging about how I value their work/contribution/knowledge, “I sure hope that you get to give the big presentation in Houston, you’d be perfect for that audience.” I sandwich the negative and difficult part of the conversation between two positive and promoting statements, where the recipient usually really hears the compliments, and the difficult issue is a much easy pill to swallow. Now I do not believe that I am playing psychologist here, rather it is a fair and gentle way of getting a difficult message across.

    • Laurel, I love the idea of a sugar sandwich. It’s not about paying false praise, but delivering honest positive comments to the person. I think that in addition to making them more open to the discussion, it also acts to remind you that they are not all bad. Ending on a positive note does the same thing and allows you both to walk away without bitterness.

      Carrying a grudge is no fun in the first place, carrying a grudge at work is like making a little bit of Hell on Earth for yourself and the people around you. It’s not useful emotionally or professionally.

  21. Good advice! I’ve always disliked getting “called out” in front of others, whether it is me or someone else. If there is something to say, privacy is a much more respectful way to do it.

    • Thanks Stacy. The only objective to calling someone out in front of others is to attempt to humiliate them. No good will ever come from that and shows a decided lack of professionalism on the part of the person doing the calling.

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