The More I Prepare for a Session, The Worse I Do

When I started out offering philosophical life coaching, I was all-around nervous.

I was nervous to announce my new endeavor. After all, everyone and their mom is a "coach" now, and it sounds cheesy as hell.

But social media announcement-type nerves are nothing compared to the anxiety associated with actually getting on a call with someone.

When I put up my coaching website and people started to pay me for intro sessions, I was delighted! But it also put a rock in my stomach and a lump in my throat.

After all, what coaching clients pay for is a chunk of time in which to talk to me. So, there is a palpable pressure to squeeze productivity out of the session time.

Unfortunately, philosophical "productivity" is not straightforward. It can take a lot of flopping around in the weeds of an issue to identify its core, brainstorm new ways of thinking, and try them on.

Not wanting to look or feel like a fraud, I decided to prepare extensively for every call. So I'd pull up all my notes, pore over them, and make jot down lots of brilliant things to say.

I basically invented to coaching labor theory of value: if I worked hard for each session, then it'd have to be valuable to the client. Right?!

The problem is that this coaching labor theory of value isn't true. I quickly observed that the more I prepare for a session, the worse it goes.

Why do coaching sessions go worse if I prepare heavily for them?

• When I already know what I want to say, I become a much worse listener.
• Preparations put me into teaching or even lecturing mode, when that's not primarily the goal of coaching.
• Preparations make coaching feel more like practicing for performing in a music recital or studying for an exam than relating to someone one-on-one.
• Preparing doesn't even work very well to make me less nervous! it actually reinforces the idea that coaching people is extremely difficult for me, and that I'll only do well with continuous application of extreme effort.

Is there an upside? Preparing for a session does keep you from encountering completely dead silences. But it isn't worth the tradeoff.

Pauses in the conversation are normal. If they don't occur in a coaching context, it probably means that the coach is talking too much and rushing to fill every gap.

All you really need to keep a conversation flowing is to feel genuine curiosity and benevolence towards your conversation partner.

(If you have hired me or are thinking of doing so: please know that I am committed to adding value to your life through philosophical conversation, but preparing extensively for each session isn't the way.)

Instead, I am constantly learning things and reflecting. Then, I can bring my whole self to bear on our sessions in a present, real-time way.

Experience and expertise matter, but they don't accrete into a pile of propositions you can reference - they mature into a faculty you can deploy.