Difficult Conversations – 5 Takeaways to Help Your Conversations

Difficult Conversation

How do you handle difficult conversations? When I am faced with difficult conversations, I tend to shut down. 

I want to be better at handling those conversations. I meet people who handle them flawlessly. They look like a commander of speech – nothing can make them waver. 

They know the right questions. They know the right responses. They know how to handle objections with a calm voice. 

I enjoy watching them guide people through difficult conversations because it is like a beautiful walk through a very uneven, jagged forest trail. It should be difficult, but it does not feel difficult. 

Money conversations are difficult. There are past histories, current emotions, and different perspectives that shape the conversation, which make it easy to get upset, exit the conversation, and prolong the problem. 

How do you handle those conversations better? 

The BookDifficult Conversations: How to Discuss What Matters Most

I wanted to find out. I researched a few books about handling conversations and Difficult Conversations: How to Discuss What Matters Most by Douglas Stone, Bruce Patton, and Sheila Heen made the top of the list. 

For those wanting to read the book, I gave it grades below based on a few different factors. 

Informative: A

Entertaining: D

Easy to Read: B

Informative: The book has valuable information. The chapters are laid out well with examples and summaries. I feel confident every person could learn at least one thing from this book. It’s the type of book you can read over and over again at different times in life and take away new information or a new way to apply it to your life.

Entertaining: It reads like a textbook. It comes from the Harvard Negotiation Project, so I can’t fault it for reading like a textbook. Just don’t expect to laugh or feel great after reading it. 

Easy to Read: The chapters are short enough that you can read 15-20 minutes here and there, which I appreciate. It makes it easy to fit in while you are busy, but still feel like you are making progress. If it were more entertaining, it would make it easier to read, but because it is dry, I was not excited to pick it up at night. My own curiosity and learning made it easier to read. 

5 Takeaways

If I had to boil down the most meaningful parts of the book that have already impacted my life the most, it would be the following:

  • Don’t get defensive in difficult conversations – I know, easier said than done! 
  • Start the conversation with a learning mindset – have a natural curiosity in discovering how the other person feels and how they see things (i.e. for now, don’t care about your own story or telling it)
  • Facts don’t matter in difficult conversations. What is important is the other person’s values, perceptions, interpretations, past experiences, and feelings. 
  • Don’t blame – understand who contributed to what
  • It’s important to share feelings, even if it is difficult 

Here are a few other tips for difficult conversations.

I encourage you to read the book because it has examples that walk you through how to handle a difficult conversation; however, I am going to highlight a few areas and how I see them applying to difficult money conversations. 

The book talks about how every conversation really has three conversations within it:

  1. What Happened?
  2. Feelings
  3. Identity

In the “what happened?” part of the conversation, each person disagrees about what happened. Usually, there is blame and someone is trying to make the point they are right. 

In the feelings part of the conversation, each person is trying to determine how much to share about what they feel and wondering what the other person is feeling. Did someone feel angry, hurt, sad, slighted, abandoned, etc.? 

In the identity part of the conversation, each person reflects on themselves. Are you competent or incompetent? Are you lovable or insignificant? How do you see yourself moving forward? 

Difficult Money Conversation Example

Let’s create an imaginary couple, Sarah and Tyler, who are arguing about money. Sarah feels that Tyler spends too much money on football tickets every year and that money could be used for them to travel together. 

In most difficult conversations, the conversation may go something as follows:

Sarah: Why do you keep spending so much money on football tickets every year? 

Tyler: I enjoy it. 

Sarah: Don’t you think it costs a lot for not very many games?

Tyler: No, I think it is worth it. 

Sarah: It’s a waste of money and we should figure out how to cut back. 

Tyler: Why do we need to cut back? I feel like we are doing fine, and I enjoy the games. Besides, you get a massage every month. That’s almost just as expensive.

Sarah: I get a massage for my own health. The football game is anything, but healthy. 

And, the conversation likely continues to spiral out of control. Sound familiar? What happened? 

Sarah began the conversation already stating her opinion – football tickets are too expensive. She even framed her opinion as a question, which instantly put Tyler on the defensive. Sarah follows up again about the cost being high even though she already knows the answer. They continue arguing about the high cost of the games and Sarah wants Tyler to cut back without understanding his side of the story. Tyler then tries to even the playing field by identifying something Sarah spends money on that he does not agree with. 

Both think they are right. Both are assigning blame on the other. Neither took the time to learn about why each enjoys spending money on football tickets or massages. Neither are sharing their feelings.

This conversation is going nowhere. 

Fixing the Difficult Conversation – Road Map to Help

What if they used the framework the book uses? 

The roadmap should be as follows:

  1. Explore the other person’s story. How do they see the situation? 
  2. Determine the impact of your actions on them and vice versa. Share the impact you personally feel. 
  3. Identify how each of your actions interacted to lead to this point. 
  4. Vocalize your feelings, learn about their feelings, and acknowledge their feelings. 
  5. Explore your identity and don’t feel like it is the only thing defining you. 

The conversation might look something like:

Sarah: I wanted to talk to you about your football tickets purchase and our overall budget. I have thoughts on how I would like us to spend money, and I’d like to hear your thoughts. 

Tyler: Okay, but I don’t want to give up my football tickets. 

Sarah: Tell me more about the importance of the football tickets. 

Tyler: I enjoy hanging out with my friends, making it an all day event. It feels like my own little community. 

Sarah: It sounds like having a day with friends is really important and football is a good way for you to do that. Are there other reasons? 

Tyler: I think so. Growing up, we never could afford to go to any sporting events. There is a sense of pride every year when I can afford to go. It’s a reminder of where I have been and my hard work. 

Sarah: I appreciate hearing that. I did not realize the games meant so much to you. What I am hearing is that this is your time to bond with friends and it brings you joy being able to afford something that you could not when growing up. It sounds like this is one of the best ways you could spend money each year. I can see why when I bring up how expensive the tickets are, the conversation goes nowhere

Tyler: Yes, I love buying the tickets and looking forward to each game. I just can’t imagine life without them. 

Sarah: One of the reasons I brought it up in the past is because we always talked about traveling, and I always feel there is never room in the budget. I’ve always dreamed of traveling and so when we don’t make it a priority, I feel upset. 

Tyler: I didn’t realize you were upset. I figured you were okay waiting another year. I am sorry. 

Sarah: I appreciate you saying that. This has gone on a few years now, so I was wondering if we could talk about how we can prioritize what we both want to do into our monthly spending. I know I could cut back on how often I eat out for lunch. I wonder if there are areas you would be open to adjusting. 

Tyler: Sure, off the top of my head, I also could cut back on lunch. I’ll take a look at my other spending to see if I can reduce it to make room for more travel. 

Sarah: Thank you. How are you feeling about this?

Tyler: I feel better. We have a good plan.

Sarah: Me too. 

Will every conversation be that perfect? Of course not. 

But you can see how it was approached differently. Sarah started from a place of curiosity. 

She wanted to know more about the importance of the football tickets. She did not bring her own perspective first. She asked more open ended questions. She asked for more information. She repeated her understanding of what he was saying. By approaching the conversation with curiosity, Tyler had the opportunity to feel heard. 

Sarah, in turn, also had her chance to share her own thoughts and feelings. Tyler was much more receptive because he already had a chance to express how he felt. 

Phrases to Help Your Conversations

There are no perfect questions or phrases to continue a conversation, but below are some phrases you can try in your own conversations.

  • Tell me more about…
  • Please share more about why that is important to you. 
  • I wonder if it would make sense if…
  • Can you tell more more about how you see it?
  • How did my actions impact you?
  • How are you feeling about…?
  • What does that mean for you? 
  • How do you see it? 
  • Can you give me an example? 
  • Can we explore that more? 
  • What would that look like? 

Final Thoughts – Summary

I think one of the most challenging parts of a difficult conversation is acknowledging your own emotions while staying calm and learning about the other person’s feelings. Everything seems contradictory if you paint your story as the “right” story, which is why it is really important to approach every conversation from a learning viewpoint. It is equally as important to remember opposite feelings can co-exist in the same situation. 

And that is perfectly okay. 

The book does a great job of acknowledging it. The authors talk about another way you can handle difficult conversations is by adopting an “and stance.” What this means is that the world is complex. There can be two emotions that exist together, even though they are opposite.

For example, the other person can feel angry for what you did and you can feel angry for what they did. You can love someone and feel upset for what they did. They could have made a mistake and you could have still contributed to the issue. The “and stance” gives validation to your own feelings while still acknowledging the other person’s. Both of your stories can make sense because you interpret them differently.  

Money conversations are difficult conversations. Every person grew up with a different relationship to money. Every person views money differently. WIth so many competing stories, there is no correct story. Each story lives together – not always in perfect harmony. 

These tools, with practice, should help you plan and have better conversations. You may want to discuss saving for a home down payment, paying down student debt, saving for retirement, gifting to grandchildren, finding a comfortable amount to give to charity, or simply whether you should buy drinks with dinner. 

Whether it is a smaller conversation or a larger conversation, approach it with curiosity. Truly hear what the other person is saying. Explore how your actions impacted them. Share your perspective. Acknowledge their feelings and your own, even when it is difficult. Find an option that both sides can agree addresses the other’s concerns and the standards moving forward. 

And then if things don’t go well, revisit and communicate again. Difficult conversations are about difficult things that are not solved overnight. 

I know in my own life, I need to use this format. Over the years, I’ve been quick to assign blame, make unhelpful comments in passing, and ask questions as if I am right. I am a frequent user of the inconsiderate questions…”Doesn’t it make sense to do it this way?” Now, I know better. 

I’ve learned I am wrong. Sometimes, very wrong! 

It’s only been two weeks and I am already starting to see the impact when I approach conversations from a learning perspective. The conversations are deeper and more productive. I am excited to continue the momentum. 

What difficult conversation will you have next? 

Disclaimer: This article is for general information and educational purposes only and should not be considered investment, financial, legal, or tax advice. It is not a recommendation for purchase or sale of any security or investment advisory services. Please consult your own legal, financial, and other professionals to determine what may be appropriate for you. Opinions expressed are as of the date of publication, and such opinions are subject to change. Click for Full Disclaimer

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