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How to stop avoiding difficult conversations - today

  • Lin
  • Feb 26, 2024
  • 4 min read



Having conversations around differences or sensitive topics can be daunting. But sweeping things under the rug can lead to 😤 resentment, ā˜ƒļø snowballing and perhaps, šŸ™…šŸ»ā€ā™€ļø self-deception.


More honest, constructive relationships at work and in life are possible, and if nothing else, it’s helpful for our own growth to be able to have these.

I’ll share how to identify necessary difficult conversations and 4 ways to overcome the impulse to avoid these.



I grew up in a pretty authoritarian household. We had to get good grades, sometimes had individual obedience scoresheets (5 āŒĀ in a month = 1 ā˜ ļø ), and weren’t allowed to cry.

We also had lots of opportunities to travel and try things, and knew we were loved and cared for.


This made it impossible to have honest discussions about topics like money or differing opinions, because when there was peace, we didn’t want to be ā€œdisobedientā€ and disrupt it - a mindset I took into friendships and personal relationships.


It was only in my mid-30s that I could write (not even say!) something honest but difficult to my Dad, which transformed our relationship. Around the same time, I was navigating some challenging negotiations at work which I could not avoid. It wasn’t a coincidence that the same shift in mindset happened at work and at home.



Avoidance or discretion?

Just because a conversation is difficult, doesn’t mean you need to have it.Ā Five things we can ask ourselves to clarify if it’s avoidance or discretion:

  • Is there an underlying issue that will snowball if unaddressed?

  • Even if I’m not at fault for this, is it my responsibility to improve the situation?

  • Will I feel resentful if I don’t address this?

  • Is this preventing me from being honest (with myself or others) about my needs, goals and who I am?

  • Is the main reason I’m not having this conversation because I’m afraid of the outcome?

If the answer is ā€œyesā€, then it’s worth exploring:

  • Our assumptions about what will happen

  • Our assumptions about our ability to handle what will happen

  • The costs of not having that conversation

  • What our inaction tells others about us

(Side note: Procrastination is a form of avoidance, and also a symptom not a cause).



4 immediate steps to overcome avoidance

If it is indeed avoidance, here’s three ways I started opening that door to difficult conversations for myself:


1) Checking my own expectations and assumptions

Conversations were often difficult because of the fear of rejection or ā€œfailureā€. At the same time, putting in the thought and emotional effort to actually raise a difficult topic somehow led me to expect perfect outcomes.

This doubled the pressure: expecting perfection while fearing rejection made it even harder to overcome avoidance.Ā To overcome this, I found it helpful to:

  • Dissociate the notions of ā€œfailureā€ or ā€œsuccessā€ from the outcomes

  • Recognize that I could put my best foot forward, but couldn’t control others’ reactions

  • Recognize that I didn’t really know the others’ perspectives

  • Return to my values and determine how to act in line with them

2) Simply state / share my feelings without asking for anything

I often held back because I predicted pushback or saw disagreements as confrontation. This immediately led to a defensive mindset.

Instead, a trick I now use is to simply think of it as sharing my experience. It’s not about persuading someone (yet). It’s just putting an alternative perspective out there.


3) Write a letter assuming the best case response (you don’t have to send it yet)

Once when it was too daunting to speak to someone, I wrote a letter to them acknowledging their perspective, putting my concerns forward, and suggesting how I hoped we could move forward.

Writing it out helped me clarify my thoughts and desired outcomes. Imagining the best case response helped me to get out of fight or flight mode, because in-person engagement was too intimidating.

It’s also possible to write this, and then decide later on whether to actually give them the letter. But just having that letter removes a huge mental block, because it’s now real and not just in your head.


4) Lay the ground to confine immediate reactions

If it’s appropriate, prepare or pre-agree on space to decompress and process differences. This could be openly discussed and agreed on, or it could be communicating in a way that gives that space.

For instance, agreeing that each person will take 5-10minutes to express themselves without being interrupted, then coming together again later that day to continue the conversation

Or, sending a text message and then saying ā€œThere’s no need to reply now, but I’d love to discuss this at some point next weekā€.


Remember that we often assume we know others’ perspectives. What seems clear and obvious to us, is often not so for others.


As difficult as it may seem, the onus is on ourselves to learn to have tough conversations, and communicate what is important to us. Otherwise, others will decide forĀ us.



Application

  • What’s the one difficult conversation you haven’t had yet, that would most improve your current situation?


Whenever you’re ready, there are 2 ways I can help you:

Ā 
Ā 

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© 2025 by Lin Chin.

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