You are Who You Grab Coffee With — 3 Steps to Get Expert Advice on Any Topic

Do you know one of the biggest mistakes I see people make when they’re trying to learn something new? They try to do it alone. Take a look at any successful person. Chances are, they relied on the expert advice and mentorship of someone else.

  • Plato had Socrates
  • Mike Tyson had Cus D’Amato
  • I have Jay Abraham

And despite the fact that it’s been proven to help you find success, I still see people try and tackle learning a new skill by themselves.

Why? Why don’t people just reach out and get the help they need?

The reason: Many just don’t know how.

That’s why, if you want to truly get better at a skill, you need to talk to actual experts — people who have been there before and can help us when it comes to achieving our goals.

Warning: This isn’t for the lazy. These systems are for Top Performers. I’m going to show you exactly how to find and talk to these experts AND how to not waste their time while looking like someone who doesn’t know what they’re doing. So be prepared to put in the work.

Table of Contents

Why expert advice works

A former Find Your Dream Job test student once told me that she wanted to become a business developer in Silicon Valley. The problem was, she was just 22 years old and fresh out of college, so she had no experience in business development at all. It was just something that sounded appealing.

So I told her, “You should definitely do your research on what biz dev is and what the role requires. When you’re done, I want you to go out and talk to 10 business developers or people very familiar with the role.”

After talking to 10 people, she later told me sheepishly, “Yeah, I don’t think biz dev is right for me.” Turns out, she didn’t realize you had to be a fairly senior member of a company AND have a strong Rolodex, a strong network, and have helped sell a company before.

She would never have known that had she not talked to those 10 experts.

Sure, 10 conversations with people you don’t know sound overwhelming, but which sounds more difficult: conversations with 10 strangers, or going down the wrong path for years before realizing you HATE your career?

So, as with classic IWT-style, I’m going to break down the exact systems you can use to reach out to ask an expert for guidance on ANY subject. The steps are:

  1. Find out WHO you want to learn from
  2. Invite them out to coffee — with an EXACT email script
  3. Ask them thought-provoking questions that produce great answers

Step 1: Find out who you want to learn from

When you want expert advice, you have to find the experts. That’s why you’re going to want to spend time and come up with a list of people you admire and want to learn from.

BUT before you shoot off a bunch of emails to complete strangers, you need to do your research on the topic you want to learn first. This research will come into play later when you reach out to them and start coming up with questions you want to ask.

So think: What are you trying to learn? Do you want to wake up earlier or maybe cook awesome meals? Start with a simple Google search on the topic.

Let’s go back to that programming example. When researching, take a look at:

  • YouTube videos on programming
  • Blog posts from noted programmers like Scott Hanselman
  • How-to guides
  • Articles from coding websites like Codementor

Write down key takeaways like how to get started, what you need to begin, and possible resources like online courses. This will take some time — typically a few days — but it helps you when finding who you want to learn from.

Once you have a basic understanding of the subject, you’re ready to compile a list of people you want to learn from. So, who’s really good at what you want to do? Who are the people you can glean the most knowledge from AND can help support you in learning a new skill? Here are some suggestions of who you can ask:

  • Teachers/professors
  • Authors
  • Bloggers
  • Friends
  • ANYONE you admire

NOTE: You want to be realistic about who you want to ask. If you want to learn computer programming, don’t email Bill Gates. He’s WAY too advanced. Email your buddy who’s been a programmer for years and can help you out.

If you want to start going to the gym more, don’t try to contact Dwayne “The Rock” Johnson. Call up your friend who is really good at consistently going to the gym. It doesn’t have to be crazy. Your friend can give you great advice on how to get started.

Action Step: Write down 10-20 experts you want to learn from

A lot of people get nervous when I say talk to 10-20 people — and I get it. It seems daunting and really overwhelming, but remember: All these meetings might seem like a lot, but what if my friend who wanted be going into biz dev had NOT taken them? She would have been stuck down the wrong path for years. The knowledge you can learn from these experts is priceless.

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Step 2: Invite them out to coffee (or Zoom meeting)

When it comes to inviting people out for coffee or a web meetup, you need to be able to send the perfect email introduction and NOT be someone who…

  • Asks worthless questions. Example: “Dear Ramit, what should I do with my money?” Uh….read the last 12 years of my site or my New York Times best-selling book?

  • Rambles. Example: “Hi I’m blah blah and I’m really interested in blah blah and once when I was a kid we went to the park and blah blah and…well I guess this got really long, so…yeah. Thanks for reading.”

  • Only talk about themselves. Example: “Hi Mr. Senior Exec at a Fortune 100 company, let me tell you about my background, what I studied in school, what I’m interested in….”

Instead, you’re going to draft an email that is short, concise, and gets to the heart of the matter: You want to learn from them.

This is a simple thing that signals to your expert that you are competent, won’t waste their time, and are capable of actually USING the advice they give.

Here’s a template you can use to meet just about anyone along with an analysis of why it works. Delete the bold text before you send it – unless you want to make a super-awkward first impression.

To: Jane

From: Samantha

Subject: Michigan State grad — would love to chat about your work at Deloitte

Hi Jane,

My name is Samantha Kerritt. I’m an ’04 grad from Michigan State and I came across your name on our alumni site. [TELL THEM HOW YOU CAME ACROSS THEIR NAME SO YOU DON’T SEEM LIKE A CREEP.]

I’d love to get your career advice for 15-20 minutes. I’m currently working at Acme Tech Company, but many of my friends work in consulting and each time they tell me how much they love their job, I get more interested. [THE FIRST SENTENCE SAYS WHAT SHE WANTS. MOST PEOPLE ARE FLATTERED THAT PEOPLE WANT/VALUE THEIR ADVICE.]

Most of them have told me that if I’m interested in consulting, I have to talk to someone at Deloitte. Do you think I could ask you about your job and what motivated you to choose Deloitte? I’d especially love to know how you made your choices after graduating from Michigan State. [“MICHIGAN STATE” REINFORCES SHARED BOND.]

I can meet you for coffee or at your office…or wherever it’s convenient. I can work around you! [THE BUSY PERSON IS MORE IMPORTANT THAN YOU. TREAT THEM ACCORDINGLY.]




One of the best things about this email is its brevity. There’s zero fat in the message and it just tells the recipient what she needs to know.

Action step: Use the template to invite your experts out to coffee

If you don’t already know the person’s contact information, there are plenty of resources online that will help you find it — but the BEST way is through a mutual contact.

You’re going to see a MUCH higher response rate if you spend some time finding a mutual contact between you and the person you’re emailing.

Even if you don’t think you have one, I HIGHLY suggest you search anyways. The results might surprise you.

Some good resources to check for mutual contacts:

  • Facebook (Use the site’s mutual friends tool to see who you know in common)
  • Twitter (Check out who they follow. Do they follow and engage with anyone you know?)
  • LinkedIn (Leverage the site’s mutual connections tool to see who you both know, or a common university/school you share)
  • Their blog posts
  • If they wrote a book, check the “Acknowledgements” page

Over the years, people have found mutual contact with me through ALL of these resources.

Of course, you’re also going to want to “massage” the email depending on who you send it to. After all, you don’t want to send this email to your best friend since kindergarten who’s fluent in the language you want to learn, unless you’re willing to get a reply like, “Dude, what have you been smoking?” back.

When you’ve nailed down a time to meet them, you’re ready to jump into the last step…

Step 3: Ask incredibly specific questions

Years ago, whenever I was able to grab a coffee or just talk to someone I admired, I used to ask these REALLY generic questions like:

  • “What are the top three things that made you successful?”
  • “How did you become an XYZ?”
  • “What’s the most important skill you have?”


So instead, I want you to reframe those questions. Instead of asking something like, “What are the top three things that made you successful?” ask something like, “What SURPRISED you about your current job?”

Imagine their answers. All of a sudden, they become better. It might be something like, “You know, I was told that it was mostly behind-the-scenes work on Excel, but what I didn’t realize was that there are so many interpersonal skills I needed to develop to be successful.”

Is that interesting? Yes.

Do you want to know more? Definitely.

Why is that? Because you asked an interesting question.

One thing that will help you with crafting perfect questions is doing your research beforehand. Say you’re meeting with a buddy of yours who is a social media manager for a big company. Look into his background and his work. What sort of questions can you extrapolate from everything that’s available about him and his social media prowess?

You might end up asking questions like:

  • “How has social media differed from X company to Y company?”
  • “What has been the most important factor in coming up with a good social media campaign?”
  • “What’s been your favorite part about your career/working at X company?”

Action Step: Craft a question toolbox tailored for the person you’re talking to

Throughout the week leading up to your coffee meeting, research and come up with questions to ask the person you’re meeting. Aim to come up with at LEAST 10 good, solid questions to ask them. Remember, the more specific the better.

BONUS: If you really want to exercise your social muscle, check out my video on improving your social skills. It’s less than 30 minutes.

Final Thoughts on Getting Expert Advice

If there’s one thing I can’t stress enough, it’s the importance of finding a mentor.

It doesn’t matter if you’re just starting out on your career path, or if you’ve been working for years and are ready to take the next step. Finding someone who has already been where you want to go will help you avoid heartache and the costly mistakes made out of naivety.

A mentor, or coach, can help guide you through the process of starting a business or developing an idea. They can also offer important insights into how to deal with setbacks and failures along the way. A mentor can give you confidence by knowing that someone else has been where you are now and has come through it successfully. This can help build your own courage and determination as well as inspire others around you to achieve their goals!

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