Six Rules for First Meetings

What I learned from meeting with entrepreneurs, CEOs, and builders.

These are notes for myself. This is how I approach first meetings. Mostly with entrepreneurs, CEOs, builders, but it generalizes.

1. Always start with their passion project

Always start by asking about a passion project.
Something they care about deeply, but also something you can genuinely contribute to in the conversation.

For example, asking what sports someone likes is often a dead end if you do not share those sports. It becomes hard to bridge to another topic and the conversation stalls.

A passion project is different. It is something they are emotionally invested in, something they can talk about in depth, and something where opinions, experiences, and context naturally surface. If you have any relevant opinion, you can contribute immediately and meaningfully. That creates real conversation instead of polite back-and-forth.

2. Be opinionated and spiky, but not rude

If you have an opinion, express it. Do not smooth it out too much.

Strong opinions create signal.
Either:

• they resonate with it, which creates an instant bond and a topic you can return to later, or
• they disagree, which tells you early where their boundaries and personality are.

If someone is very protective of a belief, you want to know that sooner rather than later. If your personalities fundamentally differ, you also want to learn that early. On the flip side, resonance creates not just a good conversation now, but a shared reference point you can revisit in the future.

Neutrality delays useful information.

3. Create checkpoints

A checkpoint is something you can come back to later.
It can be:

• an established fact about you
• an established fact about them
• a topic of conversation that landed well

Checkpoints create a sense of familiarity. When you say "like I said earlier" or "like we said earlier", it feels established rather than newly introduced. The conversation flows more naturally.

If you want to convey something specific, for example that you are running a successful startup, do not do it as one big speech or pitch. Instead, leave checkpoints early. Talk about how you make decisions. Talk about trade-offs. Talk about how you think about risk or execution. These tangential ideas quietly convey who you are long before you explicitly state it.

This is far more effective than saying "this is what I do, this is who I am."

4. Do an overlunge

An overlunge is a calculated overstep in manners.

You ask something personal or you resonate strongly with something. Even if they do not react, you immediately and loudly step back and apologize for being forward.

The goal is not to be abrasive. The goal is to be straightforward while signaling awareness of boundaries.

This works because people remember the moment, but they mostly remember the apology. At worst, they remember that you are direct but not rude. Whenever you need something to stick or be remembered, an overlunge followed by a clear step-back is effective.

5. Do not commit

Do not commit to favors, promises, or obligations in a first meeting.

Commitments create burden and friction. Whether they feel they owe you something or you owe them something, it creates discomfort. In my experience, that discomfort quietly degrades the relationship.

There is also a practical issue. You promise to do something, then life happens. You come home, things pile up, and now the relationship is anchored to a missed commitment.

Avoid that entirely. Keep things optional, lightweight, and non-binding.

6. Always reflect after the meeting

After the meeting, always reflect.

You might think it went well or badly, but you need to replay it carefully. Not what was discussed, but how the conversation flowed and how you handled yourself.

I personally talk it through with my wife. She is extremely perceptive, and because of that, I do not want to miss a single detail when recounting the interaction. That forces me to recall everything with maximum precision.

Talking through it helps verbalize impressions and sharpen understanding. Not feelings, but impressions. It makes patterns visible that are easy to miss otherwise.