The problem
I know a lot of people. Twenty years of running businesses, communities, and partnerships means my contact list is deep. My memory isn’t.
I’d walk into a meeting and blank on whether we’d talked last month or last year. I’d mean to follow up with someone after a conference and forget by Tuesday. I’d promise to introduce two people and then never make the connection.
The relationships were real. My systems for maintaining them were not.
What I tried
CRMs felt like I was managing customers, not humans. Spreadsheets lasted a week. “Reach out to 5 people a day” routines burned out by day three - because I was spending all my energy deciding who to reach out to instead of actually reaching out.
How Andy handles it
Every person I interact with gets a relationship dossier - automatically. When I email someone, Andy captures context. When I have a meeting, the prep brief pulls from the dossier. When someone goes quiet for too long, Andy surfaces it before I forget.
What a dossier tracks:
- Last interaction and what we talked about
- Promises I made (and whether I kept them)
- How we met and who connected us
- Shared projects, interests, and context
- Communication patterns: how often we talk, which medium they prefer
What Andy does with it:
- Pre-meeting briefs with full relationship history
- Warming alerts when a relationship is going cold
- Follow-up drafts that reference our actual conversation
- Introduction suggestions based on shared context
The result
597 relationship dossiers. Always current. I don’t maintain any of them manually.
The people I care about hear from me at the right time - not because I set a reminder, but because the system understands the rhythm of each relationship and surfaces what matters.
The most common response I get: “Wow, I can’t believe you remembered that.”
I didn’t. Andy did.