How And Why We Should All Get Better At Having Difficult Conversations

Let’s face it: it’s a tough world out there right now. If you don’t have a different opinion on some important topic from at least one immediate family member or friend, consider yourself lucky. Inevitably, we are likely all faced with the possibility of having difficult conversations on a consistent, if not daily, basis. In a time where this is the sad norm, wouldn’t it benefit everyone to get at least a little better at having difficult conversations?

This topic is especially on my mind right now because last week, I accepted a job offer with another company. Inevitably, I had to give my resignation notice where I currently work. Therefore, I’ve been having what feels like a lot of difficult conversations lately.

Today on the blog, I’m sharing some tips from my and others’ experience on ways we can get better at having difficult conversations, no matter the topic.

It’s my least favorite time in the process of switching jobs. You’ve made it to the end of the interview process, the company makes you an offer, and it’s a really good offer. You just want to be excited and let yourself bask in the awesomeness of the moment, but then the dread sets in. The realization that before you can go begin that new job, before you can start making that new salary, you have to break the news to your current company.

The same dread settles in when having difficult conversations about money. With 35% of people blaming finances for relationship stress and 54% considering a partner with debt a major reason to get a divorce, it’s no wonder conversations about money with a partner can be difficult. Disagreements on how to spend money, conversations about financial infidelity or secrecy, and feelings of shame and resentment are just a few of the reasons that make talking about money with others difficult.

There are SO MANY REASONS people shy away from having difficult conversations, no matter the topic. Kwame Christian, author of How to Have Difficult Conversations about Race and founder of the American Negotiation Institute, a global consulting firm that provides training on the concepts of negotiation in the context of difficult conversations, was a guest on the Hello Monday podcast recently.

In the context of difficult conversations, he said that we often want to avoid offending people, and that we’re afraid of awkwardness and discomfort.

I felt like he was speaking right to me. These are, for sure, my top reasons for not wanting to have difficult conversations.

But Christian goes on to tell us their slogan at the American Negotiation Institute: “We believe that the best things in life are on the other side of difficult conversations.”

And I truly believe that he is absolutely right. In my experience, the best things have resulted from having difficult conversations, if they are approached with respect, kindness, trust, and good intentions.

So how do we do this? How do we have difficult conversations that are more likely to lead to better outcomes?

Don’t take things so personally

Ok, I’ll admit, this one is really really hard. But I’m putting it first because I think it’s one of the more important ones. Although I have gotten much better at it over time, it’s by far the hardest for me. If you’re that person who is really good at not taking things personally, congratulations. I bet you are a fabulous negotiator. No really, you should know that (at least in my opinion) you’ve won at life.

But if you’re like me, not taking things so personally will take practice. It’ll take strengthening of your not-taking-it-personal muscles. But I promise that it gets easier over time.

When I had to give my first real resignation notice, I was at Emory University in Atlanta doing a postdoctoral fellowship. I was working in a lab, and taking teaching courses on the side. I had a boss for my laboratory work, in addition to the program I was taking for teaching. After 7 months of being there, I got my dream: a big fancy professor job back in Vermont, and I was leaving. It was a 3-year program, and I was leaving after 7 months. Because I had finally landed the job, the one I had always wanted.

I decided to tell my boss in person, in her office, before I sent in my official resignation letter. She was furious. I didn’t know what to expect, but I didn’t expect that. I watched in horror as she started yelling at me, her face turning bright red right before my eyes. She told me I was making a huge mistake. She told me how much I was letting her down, letting our team down. And she told the words that everyone dreads hearing…that she was disappointed in me.

I was devastated. It was the first time I had given notice, because I was excited about the next phase of my life, and it didn’t turn out at all how I expected. And now I had to spend the next two weeks in awkward misery with a boss who hated my guts.

I took her reaction personally. I questioned myself. Maybe I was making a mistake.

But she asked to meet with me a few days before my departure. Sitting at her desk, in the same chair where I’d been reprimanded and talked down to 2 weeks earlier, I listened to her tell me she was sorry. That she’d taken my resignation personally. That she worried my leaving would look bad for her, would indicate her weakness as a boss, and she took it out on me. She’d let her emotions get the best of her in the moment.

I don’t know how it looked on the outside, but my jaw felt like it was on the floor. I was just as stunned as I had been 2 weeks ago. I was in awe of her courage (not so much so that I changed my mind, of course). But I continue to think of her apology as a gift. She exemplified many a lesson that day. That we’re all human, and we all have emotions. That sometimes we don’t bring our best selves to a situation where we have to act in the moment. And that it’s ok to apologize. She showed me the power of vulnerability. We were able to leave on good terms rather than be bitter and resentful after a difficult conversation.

I believe that the initial resignation conversation we had, where she let her emotions get the best of her, would have gone a lot differently if we hadn’t taken things personally, both me and her.

Through many a difficult conversation with Mr. Dink over the years of our relationship, I know now that it’s in my nature to take things personally. But this awareness has actually made me better at having difficult conversations. My taking things personally used to derail the conversation such that I couldn’t focus on anything else. Now, I can identify that aspect, accept it, and move on toward a solution.

I think this strategy of not taking things personally works really well for a lot of difficult conversations. I think it may be harder with trickier topics such as politics and core beliefs. These days, there are so many differing opinions when it comes to politics and the way our country (the United States) is run, it can be really difficult not to take things personally when someone else’s opinion feels like an attack on the way we choose to live our lives. In this case, I think it may be more helpful to flip this trick and say it another way, especially when it comes to friends and family, people we care deeply about: assume good intentions.

At least for me, assuming good intentions has helped me have really uncomfortable conversations with family I care deeply about who have a very different political stance from me. It’s never perfect, but I think it helps with some of the tension, and the outcome is typically that we want the same things, even if we don’t agree on how to get there.

Which leads me to my next tip:

Practice compassionate curiosity

This is one of my favorites, but I can’t take credit for it. This one is from Kwame Christian that he talked about on the podcast.

It comprises 3 main steps: acknowledge and validate emotions, get curious with compassion, and joint problem solving.

I’ll admit, I have never been able to achieve this compassionate curiosity with a difficult conversation at work. Have any of you?

However, Mr. Dink and I have gotten pretty good at these steps when we have difficult conversations.

When we first started having difficult conversation, we had trouble figuring out and understanding each other’s emotions. We were always confused why the other was reacting a certain way (we didn’t react that way, so why would they?). The truth is, everyone has had different experiences, different upbringings, that shape who they are and how they respond to certain situations. Of course we’re not going to react the same way, to have the same emotions, because we aren’t the same person.

Once we figured this out, we could make a ground rule that each person is allowed to react the way they’re going to react, is allowed to have the emotions they are going to have, and it doesn’t have to get in the way of the outcome. We can separate the emotions, the reaction, from the problem and the solution.

In the same way, we can get curious with compassion instead of judging and shaming. We try to understand why the other person had the reaction they had, and that can help us get to a solution faster than if we get derailed focusing on the fact that one person had a reaction the other couldn’t identify with.

Validating emotions and getting curious with compassion helps us get to the problem solving part much faster. We don’t waste time blaming and shaming. Instead, we validate each other’s feelings and get right along to the problem solving.

The coolest part about these 3 components (acknowledging/validating emotions, getting curious with compassion, and joint problem solving) is that you can use them interchangeably, shift between them. For example, if you’re in the middle of problem solving with a partner but notice that things are getting heated (maybe they weren’t at the beginning of the conversation but it’s starting to bubble up), you can shift toward acknowledging and validating emotions and then go back to the problem solving.

And the best part about this strategy is that you can do this on your own too! Utilizing these components don’t require a second person. When you’re dealing with something difficult, you can acknowledge your own emotions, get curious with compassion (talk to yourself like you would a partner or a friend), and problem solve on your own. I’ve started doing this for myself when I find that I’m getting really worked up over something. I can feel the emotion bubbling up. Normally, I would end up snapping or saying something I didn’t mean. Now, I can pause, check in with my emotions, get curious about where they’re coming from, and problem solve on my own before snapping. We can do a lot of things on our own if we set our minds to them!

Think of the conversation as an experiment

Another tip for getting better at having difficult conversations is to treat them like an experiment.

To continue on the resignation example, I have now had to give notice several times throughout my career. Each time, I learn something new that helps me experiment with the next instance.

With this most recent resignation experience, I hadn’t known my boss all that long before giving notice (I had recently switched teams and thus bosses). Remembering how the situation went from my example above, I decided not to let my boss know in person/over the phone. I decided to send her a Teams chat, letting her know I planned to give notice, why, and offer to chat about it if she wanted.

It was still awkward as hell, and I still didn’t know how it would go, but it took some of the pressure off, took some of my stress away, to think of it like an experiment. I tried telling myself the following. Let’s see how this goes, and it’ll be helpful for the next time and Try it out, see what works/doesn’t work, and do something different the next time around.

The same could be helpful in thinking about awkward money conversations. Haven’t had the money talk yet with your partner? Wondering if they have any debt before getting married? Dreading that conversation about whether to combine finances or not? Wanting to talk to a friend about finances but not sure how to approach the topic? Think of it as an experiment. With some preparation, try out one method, and depending on how it goes, adjust and try something the next time.

Which leads me to…

Rehearse, rehearse, rehearse!

Whenever I’m going to have difficult conversations, especially when it comes to work, I always practice. Even if I’m not saying it out loud, I’m going over and over it in my head.

Some may argue that it can be dangerous to over-rehearse. While I agree with this in some situations, I feel different about difficult conversations. While I find over-rehearsing for presentations to be detrimental (mostly because it can take away authenticity), I find it paramount with difficult conversation. It sort of even goes beyond rehearsing: we should be playing out possible scenarios of how things might go.

Often, we don’t know exactly what we’re going to say when it comes to difficult conversations. We have emotions about a topic that need to be put into words, which is hard in and of itself. Often times, the first thing that comes to mind is not the best way to say something. Like how people often say “don’t send that email when you’re still upset.”

Rehearsing can help you figure out the best way to go about initiating the difficult conversation. Or maybe not the best (is there even such a thing with difficult conversations?), but the one most likely to produce the best possible outcome.

With the example of giving my notice this most recent time around, I had 2 things to consider: 1) whether I wanted to give my current company the opportunity to make me a counter-offer and 2) whether I wanted to initiate the conversation in person/on the phone or in writing.

Rehearsing was key for me here. As I went over and over the potential conversation in my head, I realized that there was no part of me that wanted to stay at the company. I played out the scenario and pictured how I would feel if they actually did make me a counter offer, and the light bulb went off. I did not even want to be in that situation, because I no longer saw myself working there. It was worth taking the risk on this new job at this new company because I had reached the end of the road where I was. Decision #1 made.

The decision of whether to talk to my boss over the phone or in writing was trickier. I had a lot of previous experience to draw on. I had the negative experience of talking to a boss in person, which I shared above. At a more recent job where I gave notice, I did it over video because my relationship with my manager was much healthier, and she knew I had been unhappy. I didn’t think she’d be surprised to hear that I was resigning.

In my current situation, thanks to rehearsing all possible scenarios in my head, I decided this was too close to that first, negative example. I didn’t know my boss all that well, and I knew she was going to be blindsided. I decided it would be better to give her the news over a Teams chat, and then she could react however she was going to react, and she could decide if she wanted to talk to me about it in person/over the phone. It ended up working really well, and I’m happy with the outcome (but let’s be honest…mostly I’m just glad to have the conversation over with).

Rehearsing is also helpful with difficult conversations about money. If you’re regular readers of the blog, you know that Mr. Dink and I keep our finances separate. However, this works for us because we have full transparency about what both of us our spending, how much money is coming in and going out. We still run large purchases by each other.

One of the larger purchases Mr. Dink has made in our relationship was a tractor to help maintain our property. I will never forget the day he approached me about the purchase. He asked if he could talk to me about something important (he got my attention with that), and he proceeded to tell me in great detail and with immense patience why he wanted to buy this tractor.

I could tell he had practiced, whether out loud or in his head, what he was going to say to me. I was instantly impressed. To me, him rehearsing showed me with more than his words how important this purchase was to him. Also, by rehearsing, he could think about what he knew was important to me, and make sure that he included these things in his pitch (how he would maintain it, all the cost breakdowns, how he would pay for it, what account it would come out of, etc.).

He also told me later that rehearsing it had made him really think about and consider the purchase. Mrs. Frugalwoods, my favorite money blogger, has a 72-hour rule her family instigates with any purchase. We’re not that specific, but we do have a joint understanding that we won’t just make big purchases on a whim. Rehearsing helped Mr. Dink really see all the value in his purchase and evaluate whether it was the best thing for our family at the time.

Keep the end goal in mind

Last but certainly not least. This is a big one, and one that I find is maybe most helpful with the stress and/or anxiety that comes from a difficult conversation.

No one (I think) likes having difficult conversations, but they are important, and many times they need to happen in order to move forward (eg, I need to give notice before I can move on to the next job).

For me, this really helped with my anxiety around giving notice. I really didn’t want to do it. It’s my least favorite part of any job transition. But I knew it had to happen.

When I got nervous, I reminded myself of my end goal. I wanted a job where I could grow my salary before going to part time. I wanted a job with better resources, a more supportive team. There may be plenty of unknowns with the new job, but I did my best to ask all the right questions during my interview, and I knew these things were significantly lacking at my current job. For me, it was worth the risk. The possibilities were too good to pass up.

The same goes for difficult conversations about money. Maybe there’s a purchase you’ve been looking forward to, but you need buy-in from your partner or spouse. Maybe you’re looking for a relationship based on trust and honesty, but you haven’t shared your debt history yet. Maybe you want to instill your good money habits to your kids, but you disagree with how your partner manages their finances. No matter the topic, having an end goal will help lessen the stress of having a difficult conversation. Nothing will take the stress away, but being crystal clear on your why and your end goal will help.

Think of it this way. Sometimes not having the difficult conversation, or avoiding having the difficult conversation, gets in the way of you living your best life. Whatever that life may be that you’ve chosen for yourself: a race to full FIRE (financial independence, retire early) or a slower journey along the way. Sometimes we need to have the difficult conversation to get to where we want to go. And no one, I mean no one my friends, gets to live your life but you. You are in the driver’s seat. It’s time to take the wheel and live your best life. And if that means having a difficult conversation or two along the way, so be it. You have the tools you need, so use them. And don’t worry about being perfect or doing it just right: no one is, and no one does.

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What difficult conversations have you had lately? What would you add to this list of tips? I’d love to hear from you!