Originally published on Substack:
Part of the coaching modules I am currently plugging away at necessitates actually coaching someone. Funny that.
Recently, a colleague rang me to vent about an issue they were experiencing at work. Instead of doing what we might normally do and troubleshooting it together, I asked if she would like to book a coaching session with me. She did.
She arrived with a list of questions and scenarios she wanted to work through. I arrived with my coaching tools, my worksheets and a fairly structured picture in my head of how the session should unfold.
It did not unfold that way.
It was organic, occasionally wonderfully so. There were moments when the conversation felt like we were floating peacefully down a river and others when I felt like I was fighting for my life.
Breathe out. I stopped judging myself, listened, kept asking questions and gently brought us back whenever we disappeared too far down one particular rabbit hole. And somewhere along the way, she began making connections.
How she approached something at work suddenly sounded remarkably similar to how she approached something in her family life. Different situation. Same pattern of thinking.
Aha.
By the end of the session, she had identified some specific things she wanted to try in her next one-on-one with her supervisor. Then she asked when we could meet again.
When I reported the experience back to my coaching group, another coach said “This is a proper coaching session. Not a practice run, a real one and very inspirational for all student coaches, even me”, and used a phrase to describe this very real, slightly untidy kind of coaching … “The messy middle.”
I immediately loved it. Because it describes a place in my life that I can sometimes visit daily.
Between breakfast and dinner.
Between Monday and Friday.
During the weekend.
Life itself.
It is the part where things are moving, but they are not yet clear. Where you have made a decision but are still second-guessing it. Where you know what you should probably do, yet somehow keep putting it off. Where one day you feel completely certain and the next you are wondering what on earth you were thinking.
The messy middle is rarely dramatic. More often, it looks like hesitation. Procrastination. Overthinking. A burst of enthusiasm followed by a complete loss of momentum. (Cough. Writing on Substack.)
Coaching is making me pay much more attention to what happens underneath those moments.
There is usually a stretch between where we started and wherever we eventually land where we are learning, adjusting, resisting, changing our minds, trying again and occasionally wondering whether anything is happening at all.
That is the messy middle.
And perhaps it deserves a little less judgement.
