The Cringiest Coaching Conversation I Ever Had

A few years back I had the worst coaching-not-coaching conversation of my life.  A friend and colleague of mine had gotten into a heated discussion on a team project call.  Our issues simmered-under-the-surface, but never boiled over.  Leaving the call, we were in an unstated disagreement.  I was silently fuming.  She was aware something was wrong but perplexed by what exactly was going on.

Three days later she bravely raised the issue of what was happening between us.  As we navigated the troubled waters of those moments, I sensed her going into “coach mode.”  Not be to outdone, I decided to flex my coaching skills.  What ensued was the most awkward three minute conversation as we battled with brilliantly opened ended questions.  “I’m curious why you say that?” “What would it look like if we were aligned?”  When she countered with, “What does success look like?” I must confess, I thought, “It looks like getting off this call and running far away.”  

Instead, I stopped and named what was going on.   “You do realize we are both trying to coach each other right now and doing a terrible job at it?”  She started laughing, as relieved as I, to stop the spiral of questions. What happened next?  We got real.  We laughed at ourselves.  We relived some of the worst moments of the cringey conversation.  We remembered our shared friendship.  We behaved like human beings.  

While there is a process to coaching, it’s important, regardless of the circumstances, to be a person, not a coach, first.  The best coaching conversations are those where you don’t have to try so hard to be supportive, ask good questions, and establish mutual accountability.  More so than process focused, good coaching needs to be:

  • Authentic – Authenticity in coaching means showing up in a way that is consistent with who you are and what you are feeling.  Don’t pretend to be overly supportive or coddle if it’s a challenge that’s required.  Express your emotions in a sincere way – “fake positive” coaching  rarely results in a motivated coachee.
  • Natural – Remember when you are coaching you are, fundamentally, having a conversation – with some guardrails.  Don’t go through your toolbox or job aid of questions with reckless abandon.  Relax into the conversation and it will likely flow more naturally and effectively.
  • Trusting – Assume positive intent and express positive intent.  Your objective should be obvious – not under-the-surface as was the case in my cringey coaching conversation.  As a coach, you don’t want subtext – you want main message.  Let folks know you will keep the conversation in confidence.  Help them feel you are on their side and fully supportive of them even when you are delivering tough messages.
  • Focused – One of the biggest gifts we can give each other in any conversation, including coaching conversations, is not only to be listened to, but to feel heard.  Focusing completely on what the other person is saying in that moment is key.  Put aside distractions, be mindful of thinking traps including planning what your response or next brilliant question will be.
  • Human centered – You are coaching a thinking and feeling human being, not a robot, adjust accordingly.

To be clear, coaching is more than a good conversation between friends.  And it’s not giving advice.  Leadership coaching is a process of appreciative inquiry in which the coach, helps someone uncover their own answers and determine their path to success.  

The cringiest coaching conversation I had probably shouldn’t have been a coaching moment at all.  We would have been better served by having a direct conversation about our disagreement – a disagreement so unimportant I can’t remember the precise issue a few years later.  What I can remember is that our friendship endured – and a friendship that can survive the cringiest coaching conversation ever, is one worth keeping.