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Writer's pictureEric Kaufmann

How to Start Difficult Conversations (A Guide for Neurodivergent Adults)

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Hi Friends, 


In this article, I will teach you my four-step process for initiating and managing difficult conversations.


Difficult conversations can be on many subjects, such as:


  • Asking for a raise

  • Clarifying a boundary

  • Settling a disagreement


When you have a difficult conversation, something magical happens. You end up feeling:


  • Lighter and less stressed

  • Less anxious about interacting with that person

  • More confident you assertively communicated your needs


Why Do People Avoid Difficult Conversations?

I know how hard it can be to start a difficult conversation with a boss, partner, friend, or family member. Let’s be real—most of us avoid these conversations. 


Why? 


Because they’re...


Uncomfortable.

Unpredictable.

Scary.


We fear making things worse, upsetting the other person, or being misunderstood.


So, we procrastinate.


Side note: fear is one emotion that causes procrastination. It’s natural to avoid difficult conversations.


I also struggle with this skill. Instead of saying what's on my mind, sometimes, I don't say anything.


I avoid the conversation and pretend like everything is fine.


Others ask, " Eric, what's wrong?" They might mean well, but the question feels like I'm being attacked. Instead of vocalizing what's bothering me, I respond, "Nothing. I'm fine."


Can you relate?



When we procrastinate hard conversations, the disagreement or problem festers. While we tiptoe around the topic, stress and frustration build until someone erupts in anger, only making the situation worse.  


I think I can help you avoid that.


What Skills Do You Need to Start Difficult Conversations?

Starting difficult conversations is a skill. One that requires executive function and a framework. When we improve our ability to navigate these moments...


  • Stress levels drop

  • Relationships strengthen

  • Our needs are met in a way that feels authentic.


This framework can help you enter hard conversations with confidence and a plan, ensuring you express yourself while being considerate of the other person.


Let’s dive in. 


Step 1: Prepare

Before diving into a difficult conversation, prepare yourself. Take time to reflect on these questions:


  • When and where do I want to talk?

  • What do I want to share?

  • What are my fears?

  • What outcome am I hoping for?

  • What emotional state do I want to be in during the conversation?

  • If my emotions rise, how will I manage them?


These answers will ground you. You will enter the conversation with clarity on your intentions and emotional boundaries.


Step 2: Ask for Permission

To avoid blindsiding the other person, ask if it’s a good time to talk. 


This shows respect for their mental and emotional well-being and creates a safer environment for both of you. 


The key here is to use “I” statements. This allows you to express yourself without sounding accusatory.


Try these phrases:


  • “I’d like to talk about [state topic]. Is now a good time? If not, when would work for you?”


  • “I’ve been feeling uncomfortable about something recently, and I think it’s important to discuss. Is now a good time?”


  • “I sense something is off. Am I right? If so, would now be a good time to discuss it?”


These openers are powerful! They set a calm tone and invite the other person into the conversation. They also put the ball in their court, giving them the chance to decide if they are ready to talk.


Step 3: Listen From a Place of Curiosity

Imagine you’re exploring a new country, eager to learn about its art, food, and way of life.


How would your mindset be?


  • curious?

  • open-minded?

  • ready to listen?


In a difficult conversation, this is the approach we want to take. Be a curious, open-minded explorer. Approach the conversation with genuine curiosity, even if you think you know their perspective.


Be prepared to listen deeply. If you would like to learn how to become a better listener, check out my recent blog post, "The Power of Silence: Becoming a Better Listener".


 

Want to learn more about executive function coaching for adults?

Holding difficult conversations can be stressful.


Luckily, you can work with an executive function coach so you feel confident and prepared.


Schedule your no-cost inquiry meeting today 👇

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Step 4: Use Your Executive Function Skills

The executive function skills of impulse control and emotional regulation are essential for holding a difficult conversation.


When the other person is speaking, your job is to listen. Resist the urge to interrupt, defend yourself, or correct them. Practice impulse control.


If something they say upsets you, focus on staying calm. You can always come back to it once they’ve had a chance to speak.


Remember to breathe. It is a powerful way to regulate your emotions.


Conversation Starters

Now that you know the steps, you can start a difficult conversation. Remember to ask for permission and find the best time to talk (see step two).


When the time is right, give one of these conversation starters a try:


At Work

“I know you’re trying to help me in my career, but when you say, ‘Why are you late again?’ it feels like my home life isn’t being considered. Can we talk about this?”


“I know you’re trying to [insert positive intention], but when you [describe the behavior], I feel [express how it impacts you].”


“I know you value efficiency, and I want to meet expectations, but when I receive last-minute tasks, it feels overwhelming and makes prioritizing difficult. Can we talk about how to manage these deadlines better?”


Partners, Friends, and Family:

“I know you’re juggling a lot and doing your best to help, but I feel overwhelmed and unsupported when I do most of the cleaning. Can we talk about how we can split up cleaning more evenly?”


“I know you care about me and didn’t mean to hurt my feelings, but when you joke about [something personal], it makes me feel self-conscious. Can we talk about how we can be more mindful of that?”


“I know you’re trying to share your thoughts with me, but when I feel like my opinions are being brushed aside. Could we discuss how we can both feel heard in our conversations?”


Parents Talking to Children:

“I’ve noticed you’ve been quiet lately. Is there something bothering you? I’d love to talk when you’re ready.”


“I know you enjoy playing games and watching shows, but when you spend so much time on your screen, I worry about how it affects your sleep and focus. Can we talk about setting some boundaries that work for both of us?”


“I know you’re feeling frustrated, and that’s okay, but when you yell or slam doors, it makes it hard for me to understand what’s bothering you. Can we talk about what’s going on and find a better way to express it?”


Summary

Starting a difficult conversation with a boss, partner, friend, or family member can be intimidating. We often avoid them because they feel uncomfortable, unpredictable, or scary. However, procrastinating these conversations only increases stress and frustration.


When you find yourself procrastinating an important conversation, try this framework:


  1. Prepare: Know what you want to say, why you’re saying it, and how you’ll manage your emotions.

  2. Ask for Permission: Start with “I” statements and make sure it’s a good time to talk.

  3. Listen with Curiosity: Approach the conversation like a curious traveler, ready to learn.

  4. Use Executive Function Skills: Practice impulse control and emotional regulation while listening.


Here are some ways you can start a difficult conversation:


At Work: “I know you’re trying to help me in my career, but when you say, ‘Why are you late again?’ it feels like my home life isn’t being considered. Can we talk about this?”


With a Partner: “I know you’re juggling a lot, but when I do most of the cleaning, I feel unsupported. Can we talk about how we can divide tasks more evenly?”


With Your Child: “I know you enjoy screen time, but I’m worried it’s affecting your focus. Can we talk about setting some boundaries?”


For more examples and details, scroll up to check out the full list!


You’ll likely find that taking the first step feels less daunting. And, the conversation leads to greater connection. Stay curious and calm. You've got this!



P.S. 

If you want to work on your adult executive function skills, consider joining dozens of others who graduated from our Adult Executive Function Skills 101 course. Through this course, you enhance your time management, personal finances, and more. Learn more.



About the Author

Eric Kaufmann, M.Ed is a Professional Educational Therapist and Certified Executive Function Coach. He is the Co-founder of UpSkill Specialists, an online adult executive function coaching company designed to guide adults in overcoming disorganization, procrastination, and productivity roadblocks so they can unlock their potential. Eric is also the founder of Elevate Learning Solutions, an Educational Therapy practice located in San Clemente, CA, that guides students with neurological differences toward becoming independent and confident students and self-leaders.

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