Business GrowthPersonal Growth

Asking Hard Questions and Having Difficult Conversations

By March 15, 2015 4 Comments

Planning for Difficult Conversations

My Mom recently had knee surgery. She was nervous about it, understandably so as she is 85 years old. My 2+ decades of experience as a physical therapist gave her some comfort, but it was my skills as a life coach that made the biggest impact.

My new(er) career has allowed me to hone the skill of asking great questions – challenging questions – that evoke deep insight and open possibilities and avenues for healing. It has made me understand the value of having courageous conversations that lead to greater clarity, understanding, compassion and ultimately, more joy, connection and inner peace.

I sat with my Mom and asked questions like:

  • Do you have an updated will?
  • What are your wishes if something happens to you and you can’t make decisions for yourself?
  • What is the state of your finances?
  • Where do you want to live when you can no longer live here?

She did not have a will or a health care proxy document so we spent a few hours before she went in for surgery downloading and completing these important documents (you can purchase them online from

It was a difficult conversation to have. Pointing out where she was not able to manage as she used to. Talking about who should get what after she’s gone. Tears quietly rolled down my cheeks as I wrote down her final wishes. It was painful imagining how I will feel when she is no longer here.

Memories came bubbling up to the surface of challenging times and joyful times. We recalled the time I was having surgery when I was in college and how she moved mountains to be at my bedside before I went into surgery, showing up at the airport despite being told the flight was full. Buying another ticket for one segment of a flight because they told her they couldn’t let her start the journey on the other ticket because there was no seat available for the second leg of the flight. How when they saw her determination to get to me that the pilots let her ride in the jump seat of the cockpit on that second leg! (ahh, the innocence of life pre 9/11)

There was a beautiful gift that came with the process… A deep gratitude and appreciation for the time we have now. The opportunity to serve her, support her and love her – the way she has for me so many times in my life – and to express these things while she’s here. (Too often we wait till the funeral to talk about what someone meant to us).

Asking hard questions and having difficult conversations is all about facing your fears. We tend to avoid them because we are afraid of how it will make us feel (that’s too painful/upsetting) or the other person feel (I don’t want to upset them!). We worry about what they might think, or how they will react (Will they still love me/ talk to me, if I bring this up?).

There is always a gift that comes when we are able to face fear and move through it. The love, connection, money, joy, etc that we desire is on the other side of the fear and pain. We benefit from learning to lean into the things and places that scare us and turning towards that which we resist. That is where the greatest potential for personal as spiritual growth lies.

Too often we allow our fear to shut us down or derail effective communication. We swallow or censor what we really want to say or how we feel, believing the voice in our head that tells us it doesn’t really matter, that it’s not worth it. We ignore the little things until they grow into big things… Or until it’s too late.

What difficult conversations are you avoiding? I encourage you to take a deep breath, lean in and find a way to have them.

Communication is an art. It can be messy at times. Like any skill, it gets better with practice.

Here are a few tips for more effective communication:

  • It’s not so much what you say as how you say it that will determine the effectiveness of your communication.
  • Set yourself up for success! Whenever possible, choose a less busy, less stressful time and place to have a courageous conversation. Choose a place and time when you are less likely to have interruptions and can have some privacy.
  • Come from love, not fear. Take the time to assess what you are feeling (and why) before you engage the other person. When you are clear about what you are thinking or feeling, you will communicate more effectively.
  • When you speak your truth, people respond differently, so ask yourself: “what are my intentions for having this conversation?”, “What is this really about?”, “What’s the outcome I’m looking for?”.
  • If you attack the natural response for the other person is to defend. Blame is always perceived as an attack. Make it about you, not them. For example: “when you did/said ______, I felt/thought ______.”
  • When something triggers anger, sadness, frustration or disappointment in you, get to the bottom of it by saying: “I’m angry/sad/frustrated because I’m afraid that______”.

I  love hearing from you! Let me know if you find this information useful and how these tips work for you by leaving a comment below!

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