First meetings decide the pace of everything that follows, not because you show more charts but because you learn who is in front of you and why today matters to them. When you get that part right, meeting two is easy to book, the plan feels natural, and the relationship starts on trust rather than pressure.
If you would rather watch than read, there is an Andy and Ermos Show episode on this exact topic- Watch it here.
Most first meetings stall for the same reasons. The conversation stays on the surface, the prospect gives safe answers, and you leave without a clear next step. The fix is deeper discovery. People make money decisions for emotional reasons first and financial reasons second. Your job is to uncover both and connect them to a clear next step.
Open with a single invitation, then listen.
Try one of these:
Pick one. Ask it once. Stop talking. Let them answer fully. When they pause, invite more with short prompts like tell me more or what else or how long has that been true. Mirror their language back. If they say overwhelmed, use overwhelmed. If they say stuck, use stuck. Validation builds trust and trust unlocks detail.
Listening tips that actually help
Find the real pain with the Five Whys
Surface answer: I want higher returns.
First why: Why are higher returns important now
Second why: Why does that timeline matter
Third why: Why is that number the number
Fourth why: Why does that outcome matter for your family or future self
Fifth why: Why is this the year to change it
You are not interrogating. You are staying curious. By the third why you usually hear the story behind the money. That is where trust lives.
You want one clear picture of success that includes you. Ask:
If we fast forward a year, what would make you say working with me was the right decision
Let them paint it. Fewer accounts to juggle. A clear tax plan. Breathing room in the monthly budget. Progress toward that lake house. Whatever they say becomes the targets you anchor to later. Repeat their words back to confirm. So a win looks like fewer moving parts, more visibility on taxes, and a realistic path to the lake house. Anything I missed
If they stay vague, add gentle specifics without breaking the mood. What amount in cash would feel safe. What monthly number would make the budget feel breathable. What date would you love to circle for the mortgage payoff. Every concrete answer has an emotional hook. Keep pulling the thread until you feel it.
Micro-moves that change the room
End on clarity, not pressure. A first meeting is a win when both of you know the single next step and when it happens.
Here is a simple close:
Thanks for laying this out. Here is what I will do next. I will take what you shared and build a one-page plan that speaks to the three outcomes you want. We will review it together, tighten anything that feels off, and agree on the moves that matter. Does Tuesday at two or Wednesday at ten work better
That is it. One page, one review, one calendar slot. You are not solving everything in meeting one. You are earning momentum.
What goes into the one-page plan preview
The recap email that earns meeting two
Subject: Next step and one-page plan
Thank you for today. Here is what I heard in your words:
[three short lines in their language]
I will build a one-page plan that focuses on these outcomes and we will review it together.
I have us down for [day, time]. If that changes, send me a time that is easier.
Short. Clear. It proves you listened and sets a professional tone.
Talking more than you listen. Ask one opening question and stay quiet.
Chasing numbers before the story. Run the Five Whys until the real reason shows up.
Leaving without a next step. Always set a one-page plan review on the calendar.
Filling every silence. Count to three after big questions. People think in pauses.
Run this flow in your very next first meeting. Open with one invitation to talk, stay curious with the Five Whys until the real reason shows up, help them picture a year-from-now win with you in the story, then leave with a single next step and a one-page plan review on the calendar.
Quick checklist for your desk
Close your laptop with a next step scheduled and their words captured. That’s a winning first meeting.