Leadership for introverts.

Reach your potential by embracing your personality and plotting a new course. Join our free newsletter to take the Leadership for Introverts Test and start building your skills.

  • This field is for validation purposes and should be left unchanged.

My Coffee Date with a Fortune 500 CEO: The 5-Email Challenge for Intelligent Introverts


Last year, I wrote an article titled 13 Rules for Being Alone and Being Happy About It. I questioned the conventional wisdom that we all have to be outgoing extroverts to get anywhere in life.

That piece has quietly become the most popular article on Riskology.co with many thousands of views.

Wow, so many of us are introverts! We’re a quiet bunch that mostly keep to ourselves, so I’m glad to know you’re all here with me.

On that note: Today, I’d like to invite you to join myself and some friends in a very simple challenge that, quite frankly, could change all of our lives.

But first, I’d like to tell you the story behind it all.

My Coffee Date with a Fortune 500 CEO

“You did what?”

That was the sentiment around the office when I told everyone I emailed the CEO to ask if he wanted to go for lunch.

“You’re fired. That’s what Johan is going to write back when he sees an email from some intern.” That’s what they all joked. We had a laugh about how he might respond—if he responded at all.

I played along, pretending I was a little nervous. Actually, though, I had a hunch back then about what has only been proven to me over and over these last few years:

No matter how popular you are, how much money you have, or how much power you yield, at the end of the day, we’re all pretty similar and it’s nice to get an email from someone who likes you.

That’s why—despite being painfully shy in large groups of people (I am an extreme introvert at heart)—I wasn’t worried about the email I’d just sent.

It was 2008, and I was finishing up my internship with Skanska, one of the largest construction companies in the world. I’d been hired on full-time, but had negotiated a 3-month break so that my girlfriend and I could go explore Europe a bit before settling down for what I thought would be the next 40 years as a construction manager.

The first stop of the trip was Stockholm—Skanska Headquarters—and I thought to myself, “Johan (CEO) always sends me these nice newsletters every month. I should really send him something!”

So I did. The email, while I don’t remember it exactly, went something like this:

Hi Johan,

It’s Tyler; remember me? Just kidding. You don’t know me, but I’m an intern for you in The U.S.

I’m coming to visit Stockholm in a few weeks and I thought it would be great to have lunch if you can make the time. I’d really like your job some day, so maybe you can tell me how to run the company.

Hope you’re well and finding plenty of time to ride your bike (he always talked about biking). The weather here is incredible; I’ve been out for a ride almost every day.

Tyler the Intern

My co-workers teased me endlessly about this. It spread around the office and, pretty soon, I was known office-wide as “That Guy.” It was a little embarassing—I wished I hadn’t told anyone—but the odds were actually quite good for me.

In reality, what’s the worst that would happen? He just wouldn’t write back and I’d forever be “that one guy that sent a stupid email to the CEO.”

Of course, a few days later Johan did write back. And while he didn’t have time for lunch, he invited me to his office for coffee. When I arrived in Sweden, I took him up on it.

Best cup of coffee I ever had.

The Power of Networking for Intelligent Introverts

Why bother with networking? Especially when you’re an introvert who’d rather be doing anything else (I feel ya’…)? Simple: because it will change your life for the better, and there are lots of very “feel good” ways to do it that can enrich your life as an introvert instead of cause you stress.

Until recently, I hated the word “networking.” I could only think of it as something smarmy people did. The picture in my head was of a slimy salesman going to networking event after networking event filled with other slimy salesmen handing out business cards to people they don’t care about hoping to sell more garbage they don’t believe in.

But when I was hired at Skanska, I had a realization. I noticed that, despite my sometimes painful introversion, every job I had ever gotten in my entire life depended a lot more on who I knew than on what I knew or could do.

  • I got my very first job in middle school at a car lot because my dad had built a relationship with the guy who owned it (Admittedly, I get no credit for this. Thanks, Dad!).
  • In high school, I got lots of jobs doing yard and farm work because I’d built friendships with other kids at school who had parents with a lot of property to maintain. I never even got a callback the times I dropped off a résumé at local stores.
  • My first job in college came through a connection I’d made with the school’s wrestling coach.
  • Later, I became a resident assistant thanks to a recommendation from my own resident assistant, Matt, who I’d made friends with. Hundreds of people applied and I had no previous experience to set me apart. Matt and I are still friends today. I even climbed Mt. Kilimanjaro with him a couple of years ago.
  • As an architecture student, I made it a point to get to know the campus housing director because he had money to dole out for small projects. I wanted a shot at designing some of them. I never did design anything for him, but he was the one who recommended me to Skanska, the job that paid me more than any 23-year-old should have made and gave me an opportunity to send that email to meet Johan.
  • Today, running Riskology.co, I can attribute most of the success its experienced to simply getting to know the right people—the people I looked up to and wanted to connect with anyway.

I hated “networking” until I realized I’d been doing it all along. I just wasn’t doing it the way I thought it was meant to be done. But I had been successful, so apparently I was doing something right.

Opportunities to make great connections abound even for the painfully shy and introverted like me. And developing them has made a world of difference.

Introducing the 5-Email Challenge<–Scanners, this is your cue to start reading again

I was having a beer the other day while catching up with my friend Mike Pacchione. He’s a speaking coach who works with the über-famous Nancy Duarte. I hang out around him when I want to feel self-conscious about how often I say “um” and “like” when I talk.

Over a drink, he told me how his entire career started with one ridiculous email to Nancy—who he’d never met or talked to before—a few years ago. I told him about my Johan story.

We both said, “Wow, I haven’t done anything like that in a while.” I said, “We should have a challenge.” He said, “Definitely!” I said, “I’m going to invite the Riskology.co community to join us.”

And here we are. Today, I’m challenging you to send some emails just like Mike and I did. If you accept the challenge, here’s how it works:

  1. Make a list of people you respect or admire and would like to get to know.
  2. Send each of them an email like Mike and I did.
  3. Collect 5 meaningful responses. No simple “yes/no” answers or form letters from assistants.
  4. Bask in your improved social abilities.


A Few Tips on Writing Successful Emails

You don’t have to be a rocket doctor to take part in this. Sending an email is pretty darn simple. But, there are a few things you can do to lower your risk of rejection/being ignored. Consider each carefully as you begin your campaign:

  • You don’t have to go after über-celebrities. Just think of people who you look up to and would like to get to know. Starting with this makes things a lot easier.
  • Finding someone’s email address when it’s not publicly displayed is easy. Think about all the common variations you see on a daily basis, try them out, and you’ll probably strike gold with one of them.
  • Your email should be short. People are busy and don’t have time or energy for a life story. Keep it under five sentences if you want a reply.
  • The P.S. always gets read. This is an old copywriting trick. Even if the rest of your email gets ignored, everyone reads the P.S. line, so always include one and make it the catchy. Questions work best.
  • Don’t ask for anything in your first email. Much better is to just express your gratitude and ask for advice or a question you’re pondering. If you do ask for something more significant, though, you’d better make it extremely easy for them to say yes to. Nothing they have to think about or work too hard to provide or you’ll just get ignored.
  • Offering help of some kind is a good relationship builder, but never ask “Is there anything I can help you with.” The answer will always be, “Umm, I don’t know,” and it will be expressed in the form of ignoring you.
  • It’s going to take more than 5 emails. Unless you’re the greatest email writer in the history of the universe or you’re not stretching yourself, you’ll have to write more than 5 emails to more than 5 different people to get 5 responses back.