Trust Skills Audit: Too Much About Me, Sir

Fifty-two minutes into a patio catch-up with an old friend, I heard myself say it: "Anyways, too much about me, sir."

Three of my stories had just run back to back. My career leap. My divorce. An old friend we both knew and what became of her. We hadn't sat across a table in years, and I was hosting a retrospective of my own life.

I know all this. I teach it. And I still get caught by too much "about me."

The catch, when it finally came, wasn't a triumph of self-awareness. It was self-awareness showing up 52 minutes late.

I'm only thinking about this because of a tool I built to check on myself. Here are my results:

Do Your Own Trust Skills Audit

It's called the Trust Audit. Three text files you feed to the AI assistant you already use, along with a transcript of one real conversation. It counts how much of the call was you. It sorts your questions into ones asked to learn and ones asked to create an opening for your own material. Then it hands you one pattern, one verbatim quote as evidence, and one thing to try on your next call. No flattery. The first version I built was honest to the point of abuse, and I had to soften it before anyone else could use it.

I have been testing it on my own calls before letting it out of the house as a beta.

One of the calls was with someone earlier in their career who wanted to talk about their next move. They opened with some good personal news. The audit shows my response arriving within one turn: "I didn't know if you did or you didn't, but I did that five years ago after swearing I would never do it again." Their news. My story. On a call that existed to be about them, the audit clocked me at more than half the airtime.

Same pattern in too many of my calls. Someone shares something real, and within a breath I'm telling the matching story from my own life. From the inside it feels like connection. Me too. I've been there. From the other chair it's a conversation that keeps ending up somewhere else.

Shrink your lag

What I took from the reports wasn't shame. It was a number. Fifty-two minutes is how long it took me to notice. That's the skill, I think, and I'm still working out how to say this in the second edition of my new book, From Asshole to Ally. Not never making it about you. Nobody clears that bar. The skill is shrinking the lag between doing it and catching it. My lag is currently 52 minutes. I'd like it under one story.

Beta test the Trust Audit

The audit is now in beta. Version 0.6, rough edges, free. Here is everything you need to know to run it.

Request the kit. Fill in the short form here: Request the Trust Audit Kit. You'll get an email with three small files: a Read Me, the coach instructions, and a vocabulary file. That email is the whole transaction. No software, nothing to install. Just upload the files into your AI.

Get a transcript. One real conversation: a client call, a prospect meeting, a catch-up with a colleague. Zoom, Teams, Otter, and Google Meet can all export one. The messier the back-and-forth, the thinner the read, and the audit will say so rather than guess.

Run it. Start a new chat with the AI assistant you already use (Claude and ChatGPT both work). Attach the coach instructions, the vocabulary file, and your transcript. Paste the audit prompt from the Read Me, put your name in it, and send. The report comes back in under a minute: your airtime, your question split, one pattern, the quote that proves it, and one thing to try on your next call.

About your transcript. It never comes to me. The audit runs entirely inside your own AI account, under that provider's privacy policies. I never see your calls.

And in return

What I'm asking for is the findings. Run it on one conversation, then reply to this or email me at scott@winthequestion.com with two things: what it got right, and what it got wrong. Both answers make version 0.7 better.

One warning from the field: one conversation is one data point. A pattern that shows up once is worth watching. Mine showed up on both calls, which is why I'm telling you about it.

My next client call is on the calendar. Otter already does notes for all my meetings. I'm ready to get better.