6 Steps for Successful Difficult Conversations

Are there conversations you want to have but you avoid because it’s too uncomfortable for you to have them? In this blog, I’ll share 6 steps to conducting successful difficult conversations.

 
Many of us avoid scary conversations because it seems dangerous. We feel poorly equipped to have them.

You may also see the consequences of your inaction. Things might continue to fester and it can contaminate other areas of your life.

I would like to offer 6 steps to initiating and conducting successful conversations—no matter how scary or difficult. 

First I’ll share a list of the 6 steps. Then I’ll illustrate each step with examples.

Here are the six steps,

Step #1: Know Your Why. Identify the reason you’re having this conversations, and how you’ll measure success.

Step #2: Get to Calm. Avoid conversations when your nervous system is dysregulated.

Step #3 Do Your Homework

Step #4: Map It Out 

Step #5: Do it

Step #6: Debrief. Do some Monday Morning Quarterbacking

Let’s dive into the 6 steps.

Step #1: Know Your Why. 

 Ask yourself, “What am I hoping to accomplish with this conversation, and how will I know if I’m successful?”

 And let’s take a specific example. For Melissa, the words “that’s so OCD” are like fingernails on a chalkboard. While the words “That’s so OCD” are often meant as a compliment, Melissa knows  there’s nothing attractive or desirable about OCD. She has witnessed in her own home that unmanaged OCD erodes lives.

Mellissa decides that she does not want to remain silent anymore.  She’ll speak up with the next person who says, “That’s so OCD.”

Here are a few reasons to engage in a difficult conversation:

To Educate. Maybe Melissa is having lunch with a co-worker who pulls out her phone and shows her a picture of an organized kitchen and says, “How OCD.” Melissa could say, “Wow, it would be great to have that level of organization of my kitchen. You also know there’s a difference between someone who is organized and someone with OCD. Some people with OCD don’t even have organized spaces. The statement ”That’s so OCD” disrespects the true struggles of someone with OCD.

To Clear the Air. Maybe Melissa finds herself withdrawing from a friend who says, “That’s so OCD.” She wants to reconnect with her friend, but to move forward she can no longer remain silent about her friend’s clumsy insensitive comments about OCD. 

To Understand. Maybe Melissa is genuinely curious about her employee’s understanding of OCD really is. 

To Make a Request. Maybe Melissa has a conversation with her employee and says, “I notice that at the Zoom meeting you saw Sam’s organized office and commented, “That’s so OCD.” I understand that you intended this as a compliment; however, there’s a difference between organization and OCD. OCD is a debilitating disorder. Out of respect for those with OCD, please refrain from using that language, “That’s so OCD.” 

To Set Boundaries. Let’s say Melissa makes the request which her employee ignores. <elissa could inform this employee that if she continues to use the phrase “That’s so oCd”, she runs the risk of probation. Just to point out, you cannot control the actions of others—like the words they use; however, you can set personal boundaries between what you can accept and what you cannot. You also lay out what YOU will do differently if a boundary is violated.  You will leave the room. You will end the friendship. You will terminate an employee.

To show someone you care about what’s in their blind spot. This is the “spinach in the teeth” goal. This is the kind of things you would want to know if the shoe were on the other foot. You might remember having a personal hygiene talk with your teenagers.  I remember being in New York on a windy Fall evening. I was wearing a dress and a hip-length coat.  A police officer took me aside and let me know that my dress was hoisted up in the back. That’s something I would want to know. 

You’re having a difficult conversation for YOU.  You want to be the person who tells their truth, is willing to be vulnerable and has a commitment to fostering intimacy.

That’s the way to have a clean conversation.

Sometimes the motivation is not so clean. 

You may be having the conversation to feel better. And you believe that your conversation partner needs to say or do something for you to feel better. 

Brian told me, “I need this person to apologize before I can move on. And I really want to move on.”

While Brian can certainly make a request for an apology, the truth is that Brian can move forward by making the choice to forgive, regardless of whether the other person  offers him an apology. Forgiveness is the process of accepting the past as it was, without an urge to go back and make it different. Forgiveness is an inside job.

By understanding that your thoughts create your feelings, and that you are in control of your thoughts is empowering. The ides that your feelings depend on your circumstances or the actions of others is disempowering. 

Last, our human brains find the idea of revenge attractive. Some people engage in conversations to punish a person you think inflicted pain on you. “You hurt me and now I’m going to hurt you.” This is downright dirty, and I recommend against it. 

Once you have clarity about your goal, you have a way of determining how successful the conversations was. 

The best reason to initiate a conversation is this: you’re being the kind of person or parent or partner or friend or employer you want to be. “I’m the kind of friend who tells someone if they have spinach in their teeth. I’d want my friend to do that same thing for me.”  You’re doing it for YOU. You want to be the person who tells their truth, is willing to be vulnerable and has a commitment to fostering intimacy.

That’s the way to have a clean conversation.

As you go through this step, you may discover that you don’t need to have this conversation at all. Maybe you need to do your own self coaching to consider what thoughts will create the feelings that inspire the action that help you get your desired result. 

Step #2 Get to Calm

You will be tempted to jump in have difficult conversations right there and right then in the heat of the moment. This is usually a bad idea. Avoid conversations when your nervous system is dysregulated, 

Let me give you an example. 

A few weeks ago my son flew out to spend some time with me. He was excited about a job he had taken on—cutting down 2 70-year-old pines on my property that had died. We had purchased a chain saw at his last visit, but time ran out. 

I offered to pay for my son’s airplane ticket, and he accepted. I gave him my credit card information and suggested he book flights that worked for him. Then he let me know that he booked the tickets and told me the travel days. I asked him to forward his itinerary.

When he forwarded the flight information several days later, I saw red. I do a fair amount of flying for business and I knew this flight should be in the $300 range. He paid almost $600 for this flight.  

I wanted to have two conversations with my son. 

The first was urgent. What were our options for this ticket? Could we cancel this reservation and rebook?

Second, how in the world did he research flights and chose this one? It takes a bit of talent to identify a flight that’s twice as expensive.

Unfortunately for me, I rolled both of these conversations into the same call I impulsively made while the full arsenal of anger chemicals coursed through my veins. 

 
The conversation did not go well. My son recognized he made a mistake; however, he also felt attacked. Now we had a rupture in our relationship that needed to be repaired.

I wish I got to calm before I picked up the phone. 

Had I been calm, I would have read the the terms of the ticket and seen that this was nonrefundable after the first 24 hours. There was no urgency to act; that window had closed. 

Had I been calm, I would have taken responsibility for my own contributions to this situation. I could have said to my son before he booked the flight, “I’ve booked this flight lots of times, and the fare should be about $280. Check with Sun Country. They have good fares and it’s easier to get in and out of Terminal 2 with their smaller volume and shorter lines. ”  

Had I been calm, I would have reminded myself that my son has lots of options about what to do with his vacation days, and he chose to spend it with me. 

Had I been calm, I could have compared this extra $300 to the cost of hiring someone to cut down the trees.
 

Had I been calm, I would have asked myself, “What is the true cost of repeatedly requesting that my son make reservations early to avoid higher air fares? What is the true cost of nagging my son to get the reservations to me within 24 hours.” It’s much higher than $300.

Had I been calm, I would have had perspective. In the scheme of life, $300 is a fair tuition to pay for the important life lesson about how to make smart purchasing choices.  

Get to calm before you initiate difficult conversations.

If someone invites you into a difficult conversation and you’re still angry, say, “I’m so glad you brought this up. I’m interested in having this conversation with you, but this is not a good tome. How about tomorrow or next week.” You have a sense of how long it will take you to get to calm.

Step #3: Do Your Homework 

You prepare for important conversations, like job interviews or requests for a raise or presentations you deliver. You can prepare for difficult conversations, too. Here’s how.

Arm yourself with the facts. 

What was actually said and done? What would a video camera capture? 

Distinguish between what really happened and your interpretation of what happened. This helps you avoid generalizations that often inflame rather than calm strong feelings.

Melissa could say, “You’ve used the phrase ‘That’s so OCD’ three times in the past week.”

I could have said to my son, “You paid $600 for a flight I generally book for  $300.”

Get curious about your own strong feelings

Melissa and I did some coaching around her response to hearing the words, “That’s so OCD.” 

I asked her, “Why do those three word, ‘That’s so OCD’ leave you feeling irate?”

She discovered that she’s angry that it took 5 years before her daughter was diagnosed with OCD. She’s angry at the health care professionals who steered her to treatments that made things worse rather than better. She’s angry that her child with OCD suffered so much because of a general lack of education about what it means to have OCD within the medical community. 

The though that triggers the anger is this: health care professionals should make a timely diagnosis of OCD just like they make a timely diagnosis of say breast cancer. She says, “I have a friend who sued her doctor because of the delay in making the diagnosis of her breast cancer. How is OCD different than breast cancer?” In general arguing with your circumstances is an exercise in futility.

Melissa is- annoyed that so many people know so little about OCD, but that’s not the true source of the anger,. Lashing out at a friend or stranger or co-worker who says “That’s so OCD” is like coming home from a hard day at work and kicking the dog.

Melissa started practicing the thought from Maya Angelou, “When people know better, they do better.” This helped her get to calm, and put another person’s casual comment into perspective.   

Plan for another person’s strong feelings. 

 As you run through the ideal conversation in your head, here’s the common fantasy. Your conversation part says in gratitude, “You are so right about everything you brought up in the conversation. I’m going to change what I say and do based on your wise insights.” 

That may happen once in a while.

However, chances are good that the other person will express anger or sadness or guilt or shame or remorse. You might avoid difficult conversations because you want to avoid circumstances that elicit another person’s strong feelings. 

You can practice the thought, “This person is allowed to have any feelings they have. I’m safe.” Return to your reason for having this conversation. You’re doing this because you care about the other person.

Plan for another person to go on the defensive. 

As you share your ideas, the other person may go on the offense and attack you. Practice staying calm and not goin on the defense.

Someone might say to Melissa,. “Saying ‘That’s so OCD’ is no big deal. Everyone says it. Stop being so sensitive.”

If there’s a part of Melissa that believes she is too sensitive, those words could hurt.

She could say, “You’re right; I am sensitive. However, the reason I’m bringing this up is that I know how much suffering is caused when people don’t really understand what OCD is. There’s a difference between an organized kitchen and OCD.”

Think of the Fourth of July fireworks. They make a big splash for a few seconds, and then they’re gone. You can receive attacks with, “You’re right. I’m very particular about language for a reason. Words are powerful.” 

Decide how vulnerable you want to be. 

If you really want to change the way someone thinks or acts, stories make a big difference.  

The best way to help someone understand the impact of OCD is to tell stories. 

You could tell someone about how OCD has impacted your own life—with permission from the person with OCD first. 

You will have a different conversation with a partner or a friend or a co-worker. You might be willing to disclose different things to different people.

Let’s say one of your employees who is managing OCD complains about the person saying, “That’s so OCD.” If this employee is open to the idea, you might invite her to share what it’s like to live with OCD with other members of the team.

Think about timing. 

Be sensitive to the best time to initiate a conversation.

do your own thought work so can communicate cleanly. Let’s say you want to set a new boundary about your role in your child’s compulsions. Your child might have told you, “If you loved me, you would help me.” And what they mean is that if you loved them, you would help complete the compulsions so their life would be easier. If there’s even a tiny part of you that believes this is true, you might not be ready yet. You have to get clear on what a loving parent does.

When you do your homework, you may decide that not saying anything is the best choices. You don’t need to comment on every social post that says, “that’s so OCD.” Or maybe you have a response like, “Perfectionism is different than OCD. People with OCD suffer. Please do not make OCD a punchline. Here’s where you can go to learn more about this debilitating condition.”

Step #4: Map Out the Conversation 

Here’s a great way to begin a conversation. Say, “I want to have a conversation with you. My message is hard for me to say and may be hard for you to hear. Is this a good time?”

Then give a one-sentence summary. “I would like discuss your understanding of OCD.” 

Then deliver the facts. “Three time you said, “That’s so OCD in meetings.”

Express curiosity. “I am curious. Do you think someone with an organized kitchen has OCD?” 

Express confusion. Juxtapose the actions of the ideal self with the real self. Say, ”I’m confused. You are so caring. You want to help other people. How is it that you could say something that could potentially hurt someone already struggling with OCD?” I’m confused about how and why you act out of alignment when it comes to people struggling with OCD. Can you help me understand?”

Step #5: Do It

There may have been good reasons you avoided difficult conversations in the past. It’s usually because you fear what will happen.

The best way to get better at  difficult conversations is just to do it.

Step #6: Debrief

There’s a reason professional athletes review their performances. It’s a way of getting better.

You can get better at difficult conversations. Monday morning quarterbacking will help you get there. Are there phrases that you want to use next time? Are there different things that you could tweak next time.

 The longer you wait to have difficult conversations, the harder the conversation will be. 

Conversely, with the right tools, you don’t need to fear uncomfortable conversations. Remind yourself that you are doing this is the spirit of helping and building relationships.

You may say, “But Dr. Vicki, I want to address something that’s much more serious that than a stranger saying, ‘That’s so OCD.’ I want to let my child know that I’m no longer going to help complete their compulsions. That’s a much bigger deal. I fear it will break may relationship with my adult child.” 

You go through the same 6 steps. 

Remind yourself why you are having the conversation. It’s usually because you want your actions to align with the best version of yourself. You can  practice the thought, “I’m doing everything I can to help my child be freed from OCD. That is how I’m choosing to express my love. ”  

Get support. Get practice. Adopt new empowering thoughts. Every difficult conversation you have makes it easier to have the next conversation. 

With these six steps, you no longer have to fear having difficult conversations. You have the best chance of success if you show up with a calm open heart, regulated emotions and a spirit of curiosity. 

And if no one has told you yet today, I admire your courage. Managing OCD may be the hardest job I’ve taken on. Whether you’re an OCD Warrior or and OCD Champion, you’re not alone. There’s hope for a better tomorrow. You got this!