Braving Tough Conversations

One of the hardest things we must to do in life is to have difficult conversations.  In this day of immediacy and high touch, I am always amazed at how things suddenly go radio silent when the stakes are high and something really NEEDS to be said.

In my last blog Surviving the “NO!” I discussed being on the receiving end of a “hard NO”. But, I believe there is just as much, if not more vulnerability and discombobulation in delivering the “hard NO”  It takes major courage and bravery to have a face-to-face discussion with another person for the purpose of delivering information that you are sure won’t be received well…but doing it anyway!

“You can choose courage or you can choose comfort.  You can not have both.”

– Brené Brown

laptop computer macbook apple
Photo by Startup Stock Photos on

To be clear… I am not talking about a DM, an email, a text or a letter!  In fact, texting, emailing, etc when things really matter is a real chicken shit move and can be even more damaging than to have never brought it up in the first place.  The tone is often misinterpreted in writing.  Whether you are e-communicating and things become tense or argumentative, immediately (and politely) discontinue the conversation with a statement like “Let’s talk live” or “Let’s meet for coffee tomorrow… my treat.”

group of people in conference room
Photo by Christina Morillo on

When does a conversation really matter?  Well, I can’t speak for everyone but for me, a conversation is critical when the message might be perceived as negative, hurtful, or even unexpected.  It is also critical when I care deeply for a person and feel the vulnerability of a potentially lost or strained relationship.  I know the stakes are high professionally when the receiver(s) is/are clients and/or groups of people that have a significant impact on my personal/team credibility, on the reputation of the company or if t carries legal risk.

It is important to think it through before having a conversation.

Here are a few suggestions;

  1. Think carefully about the discussion.
    • What is the purpose of this conversation?
    • Why is the message important?
    • What do you want them to hear you say or take-away?
    • What are the potential vulnerabilities i.e. what is at stake?
    • How might they react?
    • How would you feel if the roles were reversed?
  2.  Plan and practice the conversation.
    • Jot down your top (3 to a max of 5) key points.  Do not write a speech!  Bullet points are best for keeping the conversation as natural and as fluid as possible.
    • Practice what you will say with someone you trust and/or out loud.  We tend to hear more when we speak out loud than we do if we practice in our heads.  Rehearsing in a mirror is even better.
  3. Ask for and dedicate uninterrupted time for the conversation.
    • Turn off ALL communication devices!  There is nothing worse than a ringing or buzzing phone during an important interaction.
    • Allow time for them to ask questions and/or respond.  Delivering a message then removing yourself promptly in “drop the mic” fashion may negate your original purpose and intensify the anticipated reaction.
    • Do your best to keep to the time allotted.  Allowing a one-hour conversation to become a 4-hour meeting is fine if it makes sense to the topic/situation (i.e. a couple attempting to talk through marital difficulties).  Schedule a follow-up meeting if you need to.
  4. Allow and accept their response.
    • If your message causes anger, allow them to vent.  Anger can be productive.  That said, name calling, violence or threats of violence should be handled accordingly.  This is why you should think carefully through the vulnerabilities.  If the fear of threats or violence exists, you may want to have the discussion in a very public place or bring along an uninvolved 3rd party to sit close by.
    • If you think they might cry, bring a small pack of tissue or make sure tissues or napkins are available.
    • Saying “Don’t cry.” or asking “Why are you so angry?” Can come across as condescending.  Give the person time in silence to process your message.
    • Check for understanding by asking questions like “am I being clear?” “do you understand what I am saying?”  “What do you hear me saying right now?”
  5. Shut-up and listen.  Need I type more?
    • Ask questions.
  6. Always open with thanking them for their time.
    • ‘Thank you for your time today.  I know you’ve got a lot on your plate right now.”
    • Never start with… “I’m sorry to have to tell you….”
  7. Be upfront with the vulnerabilities (careful not to make it all about you).
    • “I was so nervous driving over because I care about you and our friendship deeply.
  8. Avoid ultimatums.  Telling someone to do something… “or else” is a strategy that almost never works.
    • There may well be consequences, but the key is not to use those consequences to force the person to do things your way.
    • Ultimatums can be viewed as manipulative, and cause the person to shut down.

The above advice will help you tee-up the conversation in the best way possible.  The key is to put yourself in their shoes remembering that this is a person who deserves to be treated with kindness and understanding.

Remember that you can NOT change another person.  You can only change yourself and your perception of the situation.  If you find that you keep having the same conversation with the same person over and over, maybe it is time to make a hard decision about the relationship or circumstance.

Difficult conversations are just that.   But, be brave and have the discussion ANYWAY!  In all actuality despite the result or their reaction, it can be the most loving thing to do for yourself AND them!

Let’s talk more and e-message less!

Love, light, and Real Conversation!




© 2019 All Rights Reserved


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.

tonysbologna : Honest. Satirical. Observations

Funny Blogs With A Hint Of Personal Development

Bones To Bulk

From Skinny to Buff

Rock For Disability

Emma Purcell's disability life on a music tour

Me, Myself and Disability

Because it's more complicated than that...

Travellers With Disabilities

Inspired words that CreativelyAble Us To Live Life Enthusiastically With Courage, Gratitude, Love, Truth & Authenticity.... CreativelyFIT, CreativelyWELL, CreativelyYOU!

Diary of a Disabled Person.

Disability Doesn't Mean I Can't

The Life Quadriplegic

Adventures of a Powerchair user

Dr. Eric Perry’s Blog

Motivate | Inspire | Uplift


Inspired words that CreativelyAble Us To Live Life Enthusiastically With Courage, Gratitude, Love, Truth & Authenticity.... CreativelyFIT, CreativelyWELL, CreativelyYOU!

Discover WordPress

A daily selection of the best content published on WordPress, collected for you by humans who love to read.

Life Without Lines

Breaking Free from Boundaries and Living Without Fear

Business Casual

What they didn't teach you in business school

Travel Itineraries

Travel the World 4 Less

Heels&wheels ♿️👠

lifestyle -fashion-wheelies - food

%d bloggers like this:
search previous next tag category expand menu location phone mail time cart zoom edit close