'How's the company?' gets you the press release. Follow with how they're doing personally, their challenges, and 'What's next?'
The idea
Ask someone how their company is going and, unless you're already close, you'll get the PR-approved version: busy, growing, crushing it. Note it, but assume it's partial. You care more about the person than the org chart, so the real conversation starts when you ask how they're doing inside whatever news they just shared. Then ask about challenges, and then the widest question of all: "What's next?" I've lost count of how many times that question told me the person across the table was job searching.
How to do it
Open with the business question. Expect the polished answer.
Shift to them: "And how are you doing with all that?" The conversation turns 180 degrees.
Ask what's hard right now. Hopefully they know, and know what they'd need to fix it.
Ask "What's next?" and leave room. Stable people talk about where things are headed. People on the move tell you they're moving.
Cover the personal side too: what got them into their line of work, what brought them to their city, weekend or holiday plans, family.
Example
Say you catch up with a past client and ask about the business. "Great, so busy." You ask how she's holding up with all that growth, and she admits she hasn't had a weekend in two months. You ask what's next, and she says she's been taking recruiter calls. Now you know what she actually needs, and the press release never would have told you.
Watch out for
Only do this with people you genuinely care about. Otherwise it's prying.
Small-Talk Conversions: Turn traffic, weather or weekend-plans talk into a real question, like why they live where they live.
CAPITAL: Investigate: The I in CAPITAL. Learn and record what matters about your key people, so you can show them you actually know them.
The Coffee Meeting Questions: Run coffee meetings on two questions: what are you working on, and what's your biggest challenge? Then make a specific offer.
The Four Points of Information: Four places good notes come from: where the relationship stands, where their work stands, next steps, and personal details. Keep only what you'll use.