How do I get comfortable with the "scaries" of hard conversations?
- drmariecdumas
- May 22
- 5 min read

Firstly, let's call it assertiveness, and flip the script from something negative and scary to something positive! I often tell clients that when you're anxious and have a case of the "scaries" before a conversation, it's a good sign that you're on the right track for assertiveness.
Revealing your thoughts and exposing your feelings can feel risky, and imagined worst-case scenarios resulting in conflict avoidance can serve as a road-block to progress. Read on to learn some key tips for how to prepare for such conversations. With them, you are sure to satisfy your need to express how you feel, while increasing the likelihood that it will be a positive experience.
Understanding Assertiveness and Common Blocks
Being assertive means expressing your thoughts, feelings, and needs directly and honestly while respecting others. It seeks a balance between being aggressive and being passive. Assertiveness is needed to maintain healthy relationships and to manage expectations going forward. It's needed in all settings in which you operate, from family, friends, to career, in community, recreational activities, partnerships and more.
Recent surveys conducted in America showed 9 out of 10 of individuals reported that they struggle with assertiveness due to fear of confrontation. Covid and contentious global political climates have made people even more fearful of self-expression in recent years. The social phenomenons of "taking the easy text-it," unexpected quitting, and cancel culture has added to the acceptability of avoidance, instead of voicing and attempting to work through differences.
The fear of hard conversations often stems from past experiences where being assertive led to negative outcomes, or perhaps in the past you received messages about emotional repression being preferable to confrontation. Over time, this can create a cycle of avoidance, often leading to resentment and unresolved issues. Cognitive distortions and core beliefs from our pasts that are often deep-seated, serve as barriers to transparency. It's important that you challenge yourself to grow and improve in assertiveness over the course of your lifetime by examining your blocks, so that you gain competence in overcoming them. If you are consistently struggling with pushing past your reluctance, a therapist's assistance can be very helpful.
Preparing mentally for the listener's reaction is an important part of your preparation. You're not seeking to mind-read or fortune-tell, rather to emotionally divest yourself from the other person's responsibility for their feelings, and to help you prepare for your own possible reactions by anticipating possible outcomes. The familiar adage you've heard is good advice: "You're only responsible for yourself," and it's true, but it helps to mentally rehearse possible responses in advance.
A neutral approach is desired, one in which you're not focused on convincing. It is not reasonable to expect that your desires will be embraced or your outcome adopted. Perhaps the result will be compromise. Perhaps your initial effort to describe your feelings will take time to sink-in for the listener. It's probable that you will also need to do some listening to the other parties' perspective, and curiosity about their point of view will help. Your view might be outright rejected, or it might be validated and understood completely. Perhaps you'll have a listener who will try to deflect or change the subject, and you might need to use the broken record technique to bring back the conversation to topic a few times. However, the experience of having respectfully represented your thoughts and feelings is critical for your mental health, and can bring a comfort in knowing where the issue stands for both parties. It is likely to result in clarity in your future exchanges, and help you know what to expect in the future.
The Importance of Assertive Communication
Assertive communication does more than just state your opinions; it fosters understanding and respect. It allows you to express your needs, set boundaries, and address uncomfortable situations. By practicing assertiveness, you can: enhance relationships, grow closer, boost your self-esteem, reduce your anxiety, and create healthy boundaries that protect you against feelings of overwhelm or being taken advantage of in various contexts.
The DESO Script Key
The most effective tool for practicing assertiveness is the DESO script, the benefits are that it keeps you on topic, and is very clear for the listener. It's an easy tool to recall. DESO stands for Describe, Express, Specify, and Outcome. This framework gives you a clear structure for communicating your message assertively and effectively and ends your statement on a positive note. Choose a time to use it when the party you are confronting is rested, has time to listen, and can focus on what you are saying. For example, choose a time when your listener is prepared/willing to have a conversation by asking first if they have a moment to talk and are comfortable with minimal distractions.
Describe
Start by describing the situation objectively. Then, explain how your feel without accusations; use statements that talk about your inner perspective, while focusing on the facts for a neutral tone.
Example: "On Thursday evening you cancelled our plans to meet without much notice, I feel disappointed and let down because I really look forward to being together."
Express
Next, express your feelings regarding the situation. Be honest yet constructive. This helps the other individual understand your emotions.
Example: "When plans are cancelled with short notice, I end up feeling hurt because I value our time together, and feel less important to you when it's a last-minute cancellation."
Specify
Then, specify what you need or want from the other person going forward. Clarity is key.
Example: "I'd like to feel like our time together is a priority and something I can depend on. I would appreciate it if you could let me know at least a day in advance if you can’t make it, so that I can better organize my time."
Outcome
Finally, discuss the outcome you hope to achieve and invite dialogue for resolution.
Example: "I hope we can find a better way to plan our future meetings so we both feel respected and can increase our trust in each other."
Overcoming the Fear of Assertiveness
Using the DESO script can ease the fears around assertiveness by providing a clear path to follow. Here are some strategies to help you successfully implement assertiveness:
Start Small: Begin with low-stakes situations where the consequences of assertiveness are manageable. As you build confidence, you can approach more important issues with greater ease
Practice Makes Perfect: Rehearse the DESO script in front of a mirror or with a trusted person. Familiarity reduces fear. In fact, practicing in low-pressure situations can boost your confidence by 30%..
Identify Triggers: Knowing which situations create anxiety can help you prepare for assertive conversations. Keeping a journal can reveal patterns, leading to an improvement in your preparation.
Reflect on Outcomes: After having an assertive conversation, take a moment to reflect on the experience. This will reinforce positive outcomes and encourage you for the future.
Embracing Assertiveness for Growth
While assertiveness may feel intimidating, it is a critical skill that opens the door to more fulfilling and respectful relationships. Getting good at bringing up subjects for conflict resolution will develop stronger connections and give you a sense of greater control over your emotions and reactions, leading to empowerment in all areas of your life. The DESO script provides a structured method to approach challenging conversations, helping you express yourself confidently and effectively.
Remember, becoming more assertive is a gradual journey. Your allies are practice and reflection. Embrace the discomfort; each assertive conversation is a step toward empowerment, clarity, and healthier boundaries in your life.
Be well, get help if you need it.