When I first started working on my own, I would find a coffee shop that had an open table--hard to do sometimes in Chicago--and cross my fingers that there was a nearby outlet to plug in my laptop.  

Coffee meetings are where some of the best business magic happens.  

They are where new employees are hired, old friends are coerced into leaving their stable companies to jump ship and join a startup, and it's where I would find ways to try and learn more about my friends, colleagues, and potential new business partners.

As I'd wait, I'd prepare my notes for each of my meetings, and make sure that I had a few key questions and ideas to pitch in my back pocket.  Yet, one thing that I never needed to remember were the first three questions that I asked each of my hundreds of coffee meetings.

Each time someone new joined me at the table, I'd make sure that I asked him or her three questions, right out of the gate. Because, yes, they are that important. This is where you first seek to understand, then only after absorbing their answers, can you effectively seek to be understood.

Here are three questions to ask at every coffee meeting.

1. How is life?

This question is so important to fostering good business relationships.  

This is a time where you can hear about their new marriage or their baby who was just born. If you pay attention to what they tell you, they will say more than what they speak out loud.

Their eyes and facial expressions will tell you why they haven't been responding to your emails, or why they've rescheduled this meeting twice already.  

When you take an interest in their personal lives, you get to experience them as people first, business leaders second.

2. Tell me more about this. How is it going?

When I do research before a meeting, I like to find at least one thing that they're working on, that I figure they would like talking about.

I'm also a little bit nosy, so this works for both of us.

Just as equally important, learning about new projects, exciting new skillsets, or other helpful information will help you to fill in the gaps--and it will help you to frame the conversation in a way that matches their current workload.

If you're asking for mentorship at this meeting, asking about what's on their agenda may be a good call, to find out if now is the best time.

If you are hoping to start a new project, hearing that they have some time freeing up in a couple weeks, may just be the green light you were looking for.  

This also lets you in on hearing the inflection in their voice, and how excited (or not) they are about the projects they are working on.

3. How can I help you?

This is the biggest question of the three because it's where you are able to return the favor.

Presumably, they took time out of their schedule to meet you for coffee, so the least you can do is offer to help them in some way.  

You'd be surprised at some of the responses I've gotten to this question. At first glance, you'd assume it would all be directed towards them.  How can I help you--seems pretty one-sided.

However, I've had many new business opportunities that were dropped on my plate, just by offering to help.

And of course, be prepared to provide help when they do actually need something from you such as advice, mentorship, or a recommendation.

Over the course of my coffee shop meetings I've learned so much about people that I never knew before--anecdotes about their early mistakes, and even a shared mutual connection.  Even people who I've known for years tell me things that I wouldn't have found out without asking these pointed questions.  This advice is virtually guaranteed to help you leave the coffee shop with a lot more than just a latte to-go.

Published on: Apr 23, 2018
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.