The Art of the Coffee Chat

Master this subtle art to build productive relationships.

👋 Friends,

I’m currently in Dallas for Tony Robbins’ UPW conference. Over the next few weeks I’ll also be in Vegas, SF, Toronto, and Miami where I’m hosting an event (apply here).

Are there other cities you’d recommend me to host an event in? Hit reply nad let me know.

As we approach the end of year, I’m planning a few exciting things, including a major announce in a few weeks. Please follow my Linkedin to stay tuned.

Meanwhile, enjoy today’s piece!

When I moved the United States in 2020, I had to rebuild my network from scratch.

New York City was not the bustling city I had recalled from my trips many years ago.

For starters, it was August 2020 and the city was a hotbed of COVID, driving a large scale exodus of tech and business talent to other hubs like Miami, LA, and Austin.

The thriving networking scene of conferences and evening happy hours had vanished from sight and the world’s most social city had become the most isolated one.

But over time, we recovered. The in-person coffee chats came back, then the dinners, and eventually, so did the large scale events. But I realized one thing:

We had become stiff, uncomfortable, and, dare I say - antisocial after spending years indoors during the pandemic. A result of two years of sitting in front of a 15-inch monitor. This seems to be the case across the board, from Gen Z new graduates to mid-career managers, and even tenured executives.

Over the past years, I’ve learned a thing or two after doing close to a thousand coffee chats.

Today’s piece is about The Art of the Coffee Chat and how you can master this subtle art to build productive relationships.

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Coffee with Intention

In a professional context, having coffee with someone is an effective entry point to starting a longer-term relationship. But there’s no point in doing it just for the sake of “building a relationship.”

The most productive and sustainable business relationships are formed when people are clear with their intentions.

Reasons to have coffee with someone new:

1. To Learn from them

2. To Understand a topic

3. To Collaborate with them

4. To Influence them

Caveat: a reminder that this is written from the lens of building business relationships.

Let’s dig in:

now that’s a nice looking latte

1. To Learn

You might want to have coffee with someone you admire and respect, so that you can learn from them.

Someone like:

• a tenured, senior executive at your company

• an author or speaker who you admire

• a role model

Maybe they wrote something that intrigued you, or they have a skill you’d like to pick up, or they accomplished something that you hope to do one day,

A coffee chat gives you the opportunity to ask the how’s and why’s of their professional journey.

How to approach it:

Your goal should be to build rapport and acquire knowledge by being authentically curious and inquisitive.

For example - ask:

• How did they pivot from X and Y?

• What have they learned as a result of doing X?

• How do they think about what’s next for their career?

• What advice would they give someone looking to do X?

• Why did they make specific decisions within their career journey?

Thank them at the end of the chat. This sets up the groundwork for a potential mentor / mentor relationship down the road.

The key to building new relationships lies in the follow-up. One way to do this: follow-up in 3-6 months with an update on where you are—and how you’ve incorporated their advice into your journey.

2. To Understand

You might want to meet with a subject matter expert to better understand a domain or subject area.

Someone like:

• an entrepreneur who has built and sold the business you aspire to build

• an expert that has studied a specific niche for a decade

• an operator who has done the job you want to do

When I’m trying to understand a new topic, I prefer to spend time with someone who has spent hundreds—or even thousands of hours putting it into practice firsthand vs reading a book or watching a video. I call this an intellectual sparring partner.

How to approach it:

Your goal should be to ask insightful and targeted questions to help you gain the most comprehensive understanding possible.

For example - ask:

• Why? Why? Why?

• How does this work?

• Why is it done with X vs Y?

• Why did you make this decision?

• How has this decision impacted you?

With the right line of questioning you’ll be able to drive a thoughtful and productive discussion that can 10x your speed and depth of learning.

A coffee chat like this can also set up the foundation for a potential advisor / consultant relationship down the road.

3. To Collaborate

You might want to meet with someone with the intended outcome of collaborating on a future piece of work.

Someone like:

• a potential vendor you are thinking about contracting work out to

• a CEO you are thinking about doing a joint venture with

• a technical consultant you are considering hiring

How to approach it:

Your goal should be to drive a discussion to help you evaluate your compatibility with the other person as a business partner.

For example - ask:

• What are your motivations?

• What is your long term vision for X?

• What are the challenges you’re currently facing?

• What do you enjoy doing most? What do you do best?

• What are your goals? What does the roadmap look like?

Optimal outcome: leave with a list of ideas on how you can help each other and work together.

4. To Influence

You might want to meet someone with the intention of influencing them to make a specific decision.

Someone like:

• a hiring manager that is hiring for a role you’re interested in

• a potential customer that you want to convert

• an investor who writes checks in your space

How to approach it:

You have two goals here:

1. To ask effective questions to understand the problem they want to solve

2. To sell yourself as the solution to their problems

1 is important. You want to understand exactly what they are looking for. I call this Getting Answers to the Test. Then position yourself as the solution to the problem (if you truly are.)

For example - ask:

• What are your goals for the next 3-6 months?

• What is currently blocking you from getting there?

• What challenges are you currently facing?

• What would an ideal solution to your problem look like?

• What have you tried that has worked (or not worked?)

Most people get influence wrong. The most effective way to influence someone is to not to talk, but listen.

I don’t mean to overcomplicate The Art of the Coffee Chat. I promise it’s not as complex as this article may make it seem.

It all comes down to 3 principles:

1. Understand your intentions (why do you want to meet this person?)

2. Ask the right questions (do your homework)

3. Follow-up with purpose (why should you stay connected?)

When in doubt, look to build long term relationships. Approach every coffee chat, every meeting, and every new encounter with the assumption that you will know this person for decades.

You can’t go wrong with that approach.

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📌 Andrew’s Picks

Fascinating internet things I’ve come across:

• Runnin’ Down a Dream: How to succeed and Thrive in a Career You Love — A speech on careers delivered by legendary investor, Bill Gurley.

• When You’ve Got Nothing To Say — This blew my mind. There is a lot of power in using intonation to convey your message.

• Do You Want a Happy Life or a Memorable Life? — The art of balancing the art of sitting still and enjoying the breeze on your face vs. doing memorable and impactful thing. Read this if you’re an ambitious person.

Bonus: My friend launched an app!

Launching in 2024, Favs is an app for close friends. Unlike most other apps which help you meet friends, Favs is focused on purely helping you strengthening your existing friendships.

Join the waitlist at favshq.com or if you want earlier access join the VIP program and mention me on the secret code at favshq.com/vip.

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🖼️ Behind the Scenes

One thing I’m grateful for: The amount of fascinating builders I meet at my tech events.

For example, Jacob Klug - a 20 year old who started a 7-figure company while in high school.

So I’ve started a video series where I interview them and share their story with the world, including their advice for how you can build something extraordinary for yourself.

Want to be featured? Reply to this email explaining why you’re remarkable for a chance to be featured.

(NYC only)

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