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


Fellow Riskologist,

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 nearly 200 comments and 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.

I’ll be doing this right along side you, and I can’t wait to share my results. (I’ll also be coercing Mike to share his.)

For Mike and I, the challenge will end in a month on Sunday, July 7th, but you’re welcome to keep doing it for as long as you like—even the rest of your life!

At the end of the challenge, I’ll write a follow-up article with results from myself as well as stories from those of you who participated. Get on my email list if you don’t want to miss it.

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.

Will you join us? If so, leave a comment letting us know you’re in.

I can’t wait to share more stories and updates throughout the challenge.

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What smart people are saying about this...

  1. I’m in!

    I actually have done this once is the past as well. I wrote an author last year who I really admire. I wanted to let her know how much her book had challenged me and encouraged me but I had a feeling that if I sent a letter to her publisher she would never see it. So I poked around online until I found the FB page for a one woman show she was doing and sent the letter there. Two days later a got a long and thoughtful response back from her.

    And I had broken one of your rules, my letter was over a page long, maybe closer to two!

    Time to try a few more (shorter) notes.

    • Hey Anna. This is great to hear. Thanks for participating.

      The rules I have are pretty general. In your case, it sounds like you already knew what kind of email the author would like, and it worked. In that case, disregard my rules!

  2. Tyler:

    Two tweaks to my intro emails have increased my response rate by 50%, and I think they would be applicable to readers.

    1. Offer to buy the coffee/meal. Everyone, even Warren Buffet, loves free stuff. 95% of the time they’ll pay anyways.
    2. Propose a specific day/time. It makes it easier for the other person to respond to.

    Love this challenge.

  3. I can’t think of five people right now but as an introvert in the midsts of improving his sociability this is pretty much perfect.

    I’m super down.

    • Hey Cotey. Thanks so much for participating. I think once you start making a list, you’ll actually find there are quite a few more than 5 people you can think of.

      That’s how every list works for me: I have no idea what to write down then, 3 bullet points later, I can’t stop it.

  4. I’m in… Question: would you recommend that we list people we admire, only if we’ve never met them before?
    I realised while making this list, I included people I just hadn’t seen in 10 years. I don’t know if that’s risky enough.

    I’m in either way.

    • Hey Francesca! So glad to have you as part of the challenge!

      As for your question:

      I guess it’s up to you. The idea is simply to push yourself to build relationships with people you think are out of your league. If it doesn’t feel risky, you might not be getting the full benefit of the challenge.

  5. Love the challenge – even though it scares the bejeezus out of me – I’ll be shrieking every time I hit Send!

  6. My 15 year old daughter Hannah and I had an experience like that a couple of weeks ago. She is in Senior High School and has to do a week of work experience later this year. She wants to become a photographer so she was keen to seek a placement in a photographic studio. Lots of naysayers told us she would be unlikely to get someone to take her and that her best bet would be one of the generic commercial studios. I didn’t think she would learn much about the kind of photography she wants to do by that route, so we went out on a limb. She does many hours of gymnastics training after school, so between that and homework, she really didn’t have the spare time to make lots of phone calls only to be rejected, so I offered to send enquiring e-mails to sound out which companies were willing to take work experience students so she only had to phone the ones that would. Most e-mailed me back with the expected response. But one studio with a really creative slant and heaps of awards said they were willing. Hannah was very nervous about making the phone call, but when she finally plucked up the courage, the lady she spoke to was very friendly and welcoming and spoke to her for about 10 minutes even though she was in the middle of trying to organise her son’s birthday party. Now Hannah has a great placement that lots of her friends, who made do with boring placements because they were easy to get, are thoroughly jealous of. (And yes, we are both introverts!!)

    • Great story, Kathy. And it perfectly underscores one of the major lessons to be learned with a challenge like this:

      In life, you rarely get what you don’t ask for.

      • Bit of an update on this story: It was about 6 weeks later before the school released the contracts for the students to take to their mentor employers to sign. When Hannah got hers she contacted the woman to arrange a time to bring it round only to be told that the business had closed down. So we were back to square 1 with only 3 weeks to arrange an alternative. We went through the same process as before but with no luck.

        Then I had a brainwave. Why not follow her other passion – Gymnastics. We sent off an email to our State Gymnastics office and then waited. Almost 2 weeks went by and we heard nothing. So, even though he was off duty at the time, we decided to ask for information from one of the students in Hannah’s Aerial Silks class, who also works at the State office, if our contact was out of town. Turns out he had heard about our predicament and told us another person to contact. Within 24 hours we had a response saying yes they could take her. And the great thing is, this will be even better than the first placement we arranged. In addition to learning about the business management side of things, Hannah will also get to do some assistant coaching. And, last but not least, they were looking to do a promotional brochure for their schools gym program and would like Hannah to bring her camera and do a photo shoot. If the results are to their liking, she may also get to be involved in designing the brochure. So she’s getting to do even more than she would have at the photographic studio.

        In addition to all this, I recently made contact with the head coaches of another club that is a lot more successful than the one I work at to ask if I could visit their club to see how they operate in the hope of picking up some tips. I wasn’t sure what their reaction would be as some clubs can be quite secretive about their recipe for success. Not only were they more than happy for me to do so but they have extended an open invitation for the coaches & gymnasts from our club to come and do a 2 day camp training with their gymnasts. All because I decided to stick my neck out and take a few risks.

  7. Oh gosh. This is exactly the kind of thing I know I need to do (and also really really want to do), but I freeze up and get stuck in my head when it comes to finding the “right” words to say…

      • Oooh boy I’m a little nervous right now, but that was really exciting. I just sent an email to a professor of mine that I really admire for his character.

        Thanks for what you do Tyler. I really do appreciate it, and probably would have just kept waiting forever without this friendly push.

  8. I am ready to do something new in my career, so this is a great way to network with people influential in the new area of lifestyle changes for improved health.

    I have 7 names in less than 5 minutes, will start with that and see where it goes. Great idea!

    • Nice job, Van! Thanks for being a part of our community here and participating in the challenge.

      I hope everyone else reads your comment and gets inspired to make their own list.

  9. Once upon a time I was reading a book review on Amazon & the reveiwer wanted some clarification about some points in the book he was reviewing. He went on to explain that he contacted the author and met him for a cup of coffee. My brain just stopped short…do people really so casually just contact well-known strangers and invite them out? The reviewer made it sound so normal, like it was no big thing. I was floored. I’m not exactly an introvert but up to that point it had never occurred to me that one can reach out on a personal level to someone who is well-known and accomplished. And that someone might actually respond positively to a genuine request.

    I can think of 5 people easily that I would like to contact. Will I chicken out? Maybe. But I do have a list! Thanks for the challenge.

    • Don’t chicken out! You have all these examples in front of you now that show just how open and inviting people really hard.

      Honestly, the worst that’s going to happen is someone just won’t respond. I think you can handle it! :)

  10. I am in, game and down, all at once!

    I have a bit of a head start. While developing my startup, a friend referred me to three people who would be able to help me, and I emailed them out of the blue. I would end up having a long, drawn out email convo with two of them!

    I will not count them, though, since they occurred before the contest officially started.

  11. Awesome story–sounds like your initiative more than paid off. I had a similar experience, except I accidentally mistook an exec for someone else but ended up having a great conversation.

  12. I’ve cold emailed people before and had amazing results! I emailed film and TV people in my industry here in Vancouver and got the chance to work on some pretty big budget films with NO experience. Just goes to show you what putting yourself out there can do! And all because of a single email!

  13. Tyler,

    This is really inspirational. I’m definitely in and will give this a go! A friend recently inspired me to do at least 2 audacious things a week, and these emails should be one of them! He said I’ll be surprised with the results and connections made. :-)

  14. I have a recurring dream where one of my favorite writers/actors tells me I’m boring, so this idea scares me to DEATH!

    Which is why I think I’ll give it a try.

  15. Awesome challenge-I’m in! As a new small business owner I need all the advice and encouragement I can get. Hoping the 5 emails gets the ball rolling…

  16. Yes! I just did this for the first time last week and talked with the founder of a nonprofit I was interested in supporting. And I just subscribed to your newsletter for more gems like this : )

  17. Tyler ,
    Hey there just wanted to you know am thankful for what you are doing.i don’t know if its talent or what but your posts it’s like one is having a conversation with you one in one.keep up the good work.

  18. I like to say that showing up is 90% of the game. In this case it was just asking. Actually doing it. 90% of the game. Good work.

    I remember asking the owner of a company (only like 50 employees) that I worked for during college to lunch. After a few weeks he stopped by and asked me if it was a good time. It was a great lunch! I don’t remember any nuggets that he dropped for me (I guess I was expecting the keys to life or something?) but it was a great experience!

    [side note: the company was in little Auburn, AL and was called CoachComm and they make the majority of the headsets that you see football coaches wearing on the sidelines during the games]

  19. Oh awesome haha. You got me at “Scanners, this is your cue to start reading again.” And again at “Bask in your improved social abilities.”

    I will try this.

    -closet introvert

  20. Hi Tyler,

    I’m so stoked that I came across your site – I’m in my final year studying media, and one of our final assignments involves networking+conducting interviews with people already working in the media industry. It’s scary stuff, trying to find contact details and then writing up the perfect email, but after reading this I’m feeling really inspired. I love the email you sent to Johan! :)

    I was wondering what your thoughts were on subject lines…? How do you write one that encourages your email to be read? I’m finding that to be the toughest thing at the moment!

    Thanks so much for the awesome post. :)

    • Hey Thao. Subject lines are a bit tricky with people you haven’t corresponded with before. If I know the person’s personality a bit, I’ll try to tailor it to that. For instance, if I know they’re a joker, I’ll try to make it funny. Really depends on the person, though. Maybe this is something I can write more about in an upcoming article.

  21. Hi Tyler,
    I’m really excited about this challenge and so much interested. Only that in this part of the world( Nigeria ),people don’t really use mails that much. Anyway if you don’t mind,maybe I gotta include your mail in my list:-). Remember you are very much out of my league!

Founded with love by Tyler Tervooren

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